Coaching from Essence, Creating from the Future

Today, I sit down for a conversation with *my coach* Robert Ellis, about his new book, Coaching From Essence.

Robert has been described as “one of Silicon Valley’s best-kept secrets” and has been coaching leaders at startups, mid-stage companies, Fortune 500 giants, and nonprofits for over 30 years. Robert has taught leadership and coached entrepreneurs at Singularity University and developed Level UP, the leadership curriculum for the Global Startup Program, and taught leadership courses at Stanford University. We met through radical serendipity and I’m grateful for the generosity and grace Robert has coached me with. All of his teaching materials are now publicly available on his free circle community and on youtube.

Robert’s book is like sitting in a fireside chat with Robert, absorbing his profoundly wise and profoundly simple approaches to coaching. Sometimes, a new idea can feel so true that it lands like common sense - all the pieces fitting together so seamlessly and effortlessly. Roberts’ metaphors, stories and models hit like that - like powerful truths you knew all along.

Robert’s visual models help ground a coaching conversation, make it easy to follow along, and make the conversation incredibly sticky. And literally every time I’ve drawn one of these diagrams for a client, it lands with them and becomes a new metaphor for thinking about their challenge and their path forward.

This book isn’t just for coaches who want a more effortless and human approach to doing this work, it’s for anyone who wants to be deeply helpful to their clients, their teams, their organization, and to lead conversations in a more impactful way.

Coaching from Essence is based on the radical idea that everyone has an essence, and that, when we work from it, we can effortlessly create value and impact. Coaching from essence works both ways - the coach coaches from *their* essence, their natural approach…and the coachee is coached to work from their *own* essence - their own natural approach. We’re not telling people how to be. We are here to help them remove the obstacles that get in the way of them finding their own way.

According to Bill Gates, everyone needs a coach. 

I would flip this suggestion on its head and say that at some point in everyone’s lives, accessing a Coaching from Essence mindset can be a generous, powerful and transformative way to help someone in our lives.

Some of us choose to make coaching our life's work, but Coaching from Essence is a powerful, generous and transformative approach to helping people that everyone can (and should?) access at the right moment for the right person. 

Robert Ellis is the embodiment of what he teaches - he is a generous, powerful and transformative coach who I’ve had the pleasure of working under for several years. I’m so glad this book is finally out in the world so that everyone can have the experience of working with him.

Links, Quotes, Notes, and Resources

https://coachingfromessence.com/

https://www.futurosity.com/

Coaching from Essence, by Robert Ellis

Minute 1

Daniel Stillman:

I love that you quote Dolly Parton, I think she's under-quoted, and there's this beautiful quote about, "Find out who you are, and do it on purpose." And I'm curious, if you can put that in context for you. Who are you, and what is it that you do on purpose?

Robert Ellis:

What I do on purpose, is I help people create things. So the book is called Coaching from Essence, and briefly, the idea behind that is, I believe that everyone has an essence, which I think of as, everyone has a way of being valuable in the world without any real thought or effort on their part.

Or another way of thinking of it, a shorter way of thinking of it, is just that everyone has a way of being good.

And so I think, what Dolly Parton is talking about is find out who you are, find out what your essence is, find out why you're here, and what you can contribute naturally, and do that on purpose.

And what most of us do, is we do something else. I know I spent the first 60 years of my life doing something else, trying to be someone I wasn't, because I thought that would earn me more money, or get people to love me, or help me survive, or get status, or something like that.

And so what Coaching from Essence is really about, and what that quote means to me, is find out who you are naturally, what do you naturally good at? Well, what do you naturally have to offer the world? And trust that if you create a life out of that, you'll actually create a, not only be more successful in all of the usual terms, but you'll be happier and more fulfilled.

Minute 3

Robert Ellis:

I have a particular way of thinking about leadership, as you know, but kind of the short version of it is, that a leader is someone who can help people navigate through the unknown, to something better than they can imagine when they leave, wherever they start. And one of the best ways to help people navigate the unknown, is to coach them.

And coaching is really just a way of helping someone find out what their essence is, and begin to create from that, but also how to go on a quest, or how to navigate the unknown to create some something, to create more possibilities than they would otherwise have available.

Minute 17

Robert Ellis:

Leadership is, if you really want to live an adventurous life, you open yourself up to the possibility that the universe knows better than you what you could create, what's possible, and so you go on a quest to find out what's possible. You aim for B, but in this case, B is the best thing that you can imagine, and you conduct experiments, you try different things, and that's how you learn and grow.

Minute 18

Robert Ellis:

Growth to me is also not necessarily bigger. It's better, more congruent, more resonant, more authentic, more aligned with who I am. The more I create a life that is more resonant, congruent, and aligned, the more fulfilled I am, the happier I am.

Minute 41

So the futurosity continuum, and the reason it's called the futurosity continuum, is that, basically, what we're trying to describe is, what is your stance toward time? Are you creating from the past, or are you creating from the future?

Okay, so the continuum goes from the past to the future, and it starts with reactive. Reactive, meaning, something happened already and now you're just reacting to it, and you're putting out fires, or you're just in problem-solving mode. You're just reacting. You're not in control. You're just reacting to things that have already happened, so that it's very much, you're trying to manage the past.

Daniel Stillman:

Which is a really hard thing to do, by the way, given that it's already happened.

Robert Ellis:

It's a hard thing to do, right? Exactly.

So now, you're trying to fix the past, okay? You're a fixer, if you're reacting, or you're proactive.

Proactive is just, so something has happened often enough that you finally catch onto it, and you say, "Okay, let me see if I can avoid that happening again." That's proactive, but if you're reactive or proactive, you're still responding to the past, so you're what I call a fixer. That's a fixer.

After proactive is opportunistic. Once you start to create from the future, in other words, once you start to move towards something you think you want, once you start creating, you will create all kinds of possibilities. Some of which, will be aligned with your quest. They'll be directionally appropriate for what it is you're pursuing, and others that are shiny objects, they're distractions. And this is one of the problems that leaders and entrepreneurs, especially, can fall right to. So, opportunistic, but at least now you're moving toward the future. You're creating possibilities, that didn't exist before, that might lead to something good.

Strategic. The way I define strategic, is you're intentionally setting about creating a future of your own choosing. So you have an idea of what you want, and now you're taking action to create what it is you think you want.

And again, if you're on a quest, you don't know it's possible, but you have an idea of the best thing that you can imagine, so being strategic, is intentionally taking steps to create something, the best thing that you can imagine. Okay.

Then beyond strategic, is emergent, which is, now, you're in conversation with the universe. In other words, you're paying attention to what results you're getting, what response you're getting, and so you have to pay attention to weak signals. You're noticing just what's showing up for you, and you're seeing whether or not some of these things, whether or not you're creating possibilities now, that are potentially better than you might have entertained before.

So the difference between emergent and opportunistic, is that opportunistic is kind of random, and emergent is things are responding to what you're putting out. You're more intentional.

Summary

(6:49) - Robert explains that he helps people create things from their essence and discusses the importance of coaching for leaders in navigating uncertainty and creating more possibilities

(23:51) - Robert defines growth as becoming more resonant, congruent, authentic, and aligned with who you are, rather than just getting bigger

(32:13) - Robert talks about the balance between path-like and quest-like approaches in organizations, and the need for experimentation and learning to avoid being outpaced by competitors

(34:28) - Robert discusses the antidote to self-interest, status-seeking, scarcity, and survival, which he sees as essence, abundance, service, and trust. He emphasizes the importance of giving oneself away and trusting in one's natural abilities and creativity.

(45:40) - Daniel introduces the Futurosity Continuum as a model for navigating uncertainty and creating from the future

(47:36) - Robert discusses the ideal curve of spending more time on strategic and emergent thinking, with most organizations and startups spending more time on reactive and proactive thinking.

(1:00:13) - Robert explains that the purpose of his work is to help individuals and organizations express their essence and create something meaningful that improves the world

More About Robert

Robert is an executive coach and the founder of Futurosity and the Coaching From Essence training program for executive coaches.

Robert has over 30 years of experience working with global companies—spanning startups, mid-stage, Fortune 500 giants, and non-profits— guiding leaders to take their impact to the next level at any stage of growth. His proven strength in coaching entrepreneurs and CEOs to become better leaders, think more strategically, create high-performing teams, foster future-friendly cultures, and deliver compelling presentations—including several high-profile IPO roadshows—has earned him praise from one client as “one of Silicon Valley’s best-kept secrets.”

He’s taught leadership and coached entrepreneurs at Singularity University, and developed Level UP, the leadership curriculum for the Global Startup Program.

He was one of the original coaches for the Nasdaq Milestone Maker program, helping late-early to mid-stage entrepreneurs grow their businesses to the next level.

He also taught Facing Challenge, Navigating Change: Leadership and The Hero’s Journey, an 8-week course at Stanford University using Joseph Campbell’s Hero’s Journey as a framework to explore mindsets and skillsets for leading yourself and others on a heroic journey in business and in life.

Full Transcript

Daniel Stillman:

I will welcome you, officially, to the Conversation Factory.

Robert Ellis:

Thank you.

Daniel Stillman:

Robert, thanks for being here.

Robert Ellis:

I'm thrilled to be here, Daniel. It's always nice to have a conversation with you.

Daniel Stillman:

So where shall we begin? I feel like I was leafing through the early copy of Coaching from Essence, and I love that you quote Dolly Parton, I think she's under-quoted, and there's this beautiful quote about, "Find out who you are, and do it on purpose." And I'm curious, if you can put that in context for you. Who are you, and what is it that you do on purpose?

Robert Ellis:

What I do on purpose, is I help people create things. So the book is called Coaching from Essence, and briefly, the idea behind that is, I believe that everyone has an essence, which I think of as, everyone has a way of being valuable in the world without any real thought or effort on their part.

Or another way of thinking of it, a shorter way of thinking of it, is just that everyone has a way of being good.

And so I think, what Dolly Parton is talking about is find out who you are, find out what your essence is, find out why you're here, and what you can contribute naturally, and do that on purpose.

And what most of us do, is we do something else. I know I spent the first 60 years of my life doing something else, trying to be someone I wasn't, because I thought that would earn me more money, or get people to love me, or help me survive, or get status, or something like that.

And so what Coaching from Essence is really about, and what that quote means to me, is find out who you are naturally, what do you naturally good at? Well, what do you naturally have to offer the world? And trust that if you create a life out of that, you'll actually create a, not only be more successful in all of the usual terms, but you'll be happier and more fulfilled.

Daniel Stillman:

Yeah. Why is coaching a useful modality? Both for leaders to utilize for themselves, but also to use for their teams, and their organizations? Like why coaching, rather than other ways of helping in a conversation, for lack of a better word?

Robert Ellis:

Well, I think that coaching is one of the most important skills for any leader. I have a particular way of thinking about leadership, as you know, but kind of the short version of it is, that a leader is someone who can help people navigate through the unknown, to something better than they can imagine when they leave, wherever they start. And one of the best ways to help people navigate the unknown, is to coach them.

And coaching is really just a way of helping someone find out what their essence is, and begin to create from that, but also how to go on a quest, or how to navigate the unknown to create some something, to create more possibilities than they would otherwise have available. And so coaching is a way of being, which creates more possibilities.

So it's important for leaders, it's the reason I love it, is because it's a form or a context. People can enter into a conversation with me, as a coach, and there's an understanding that we're in conversation in order to create something different than what they already know or have, so it opens up tremendous possibilities, and that's exciting for me.

Daniel Stillman:

So navigating uncertainty.

Robert Ellis:

Yes.

Daniel Stillman:

How does coaching someone help them navigate through uncertainty, rather than, I think, what many people want when they're in uncertainty is, tell me how to be, tell me to think, tell me what to do. We all have a feeling of wanting a playbook, a handbook, a path when we're in uncertainty. There is a tendency, and you could point it to patriarchy, or fear. I mean, I don't know what you would pin it to, but there is a move in many of us to say, to grab for the handrail of certainty, in uncertainty.

Robert Ellis:

Yes. Yes. Well, the way I think about it is, first of all, we're all taught, what I think of as, the unconscious curriculum, we're all taught what will make us happy, is self-interest, status seeking, scarcity, and survival. And so if you're creating from self-interest, status seeking, scarcity, and survival, there's a lot of fear there.

And so, the way I think of it, sometimes, I'll draw this out for a client. I'll say, "All you're trying to do is get from A to B," and I put a dot under A, and a dot under B.

And when you're looking at a piece of paper with A and B, with these big bold dots underneath them, they look kind of like planets.

Daniel Stillman:

Yes.

Robert Ellis:

And so A is a little bit like earth, and B might be like the moon. Well, the earth has a lot more gravity than the moon, if you're on earth, and so, one of the things that keeps us wanting to be in a place where we know, is that it's safer.

So I agree with you, part of it is this sort of curriculum we've been taught about what will make us happy, is we cling to self-interest, we cling to what we think will help us survive.

And then there's fear. And there are some specific fears, that tend to come up when someone tries to navigate uncertainty. There's, what I call, thresholds, silliness, trust, sanity. The most important threshold is the love threshold, which is that we're all afraid that if we really pursue what we want, we'll discover that we're not worthy, not lovable, there's something, we don't deserve it.

Daniel Stillman:

Yeah.

Robert Ellis:

So to navigate the unknown, we have to be willing to go on that journey, and go through those thresholds, and escape the earth's gravity. We have to escape from our comfort zones, and be willing to go where it might be a little bit uncomfortable.

And so, part of coaching, is to support that. People usually come to me and most coaches, I think, with a problem, looking for a solution. And so we start there. We create some value, we help relieve some of the tension. We find some strategies for making the current situation more tolerable, but that's not a very big payoff.

And so when someone experiences some movement from where they've felt stuck, or where they've felt burdened in some way, then the invitation of coaching is, "Well, now let's see what you really want to create, and let's go on an adventure."

What could be possible for you? What do you really dream of? What's your longing?

And so that's the invitation of coaching.

Daniel Stillman:

In a way, I love that you're removing all the next questions I was going to ask, but bleeding into them, which is perfect.

This is one of the reasons why, I think one of your quotes that is one of my favorites is that, "All life coaches aren't executive coaches, but all executive coaches are life coaches."

And the idea that if we're going to create something that we really, really want to bring into the world, if we're going to go into uncertainty, if we're going off the beaten path, if there's really an adventure, we're going to hit some roadblocks.

Robert Ellis:

Yes.

Daniel Stillman:

And the deepest of those roadblocks is, who the hell am I to do this? And that often comes up. So then what is the boundary, because you and I are not therapists?

Robert Ellis:

Right.

Daniel Stillman:

Right. When we are in a coaching relationship, what do you feel like is the right way to approach things like the love threshold, which is always there?

Robert Ellis:

Yes. Well, so the first thing to understand is that, we talked briefly about essence, everyone has a natural way of being in the world that's valuable, without any thought or effort on their part. That's essence.

But we live in a world of form. All of the material things around us, my desk, my computer, it's surrounded by forms, right?

Thoughts are forms too. They're thought forms, our beliefs, our identity, our values, those are also all forms. Coaching is a form. By form, I mean that, we have a certain idea of what coaching is.

It's a kind of conversation that's different from other conversations. It's different, for example, from therapy. Coaching can be therapeutic, but it's not therapy. Therapy is a different form. They're different. There are different boundaries, different agreements about what happens in a conversation with your therapist.

But for me, the only criteria for whether or not I can talk about something with a client, is really two things. Number one is do I have permission? And two, is it helpful?

So the quote that you mentioned, "Not all life coaching is executive coaching, but all executive coaching is life coaching." What that means is I believe that we can't separate who we are personally from who we are professionally, so just because you're an executive, and just because you're coaching someone-

Daniel Stillman:

You can, but there are costs to doing it. Let's speak. Let's speak.

Robert Ellis:

Exactly. There are people who try to do that, but it doesn't work very well, and it's an illusion, I think.

Daniel Stillman:

Why not? Why doesn't it?

Robert Ellis:

You always bring yourself.

Daniel Stillman:

Why is it an illusion? Can you peel back to a little earlier on then?

Robert Ellis:

Oh, it's an illusion, because we're not ChatGPT, we're not robots, we're people. We have feelings, we have blind spots, we have history, we have background, we have beliefs, we have identity, we have values. We are human beings, and we bring that to work whether we believe that or not.

Daniel Stillman:

Yes.

Robert Ellis:

And I think it's actually disastrous if we don't acknowledge that, and don't honor it. And the evidence is, we're surrounded by the evidence of that. If you look at the world, and you see all the problems that we're facing, I think many of them are caused by the fact that we try to separate our humanity from our activity, what we're creating.

So we bring all of us to work, and that's why, if you are an executive coach, and I'm an executive coach, I'm not a life coach, meaning that I don't just work with people who are trying to improve their lives. I work with people who are trying to create things, that have the potential to impact many people.

And so my work is to help them personally.

I work with people who are trying to create something that's so aspirational, it requires a personal transformation. In other words, they're trying to create something that, as they are now, they won't succeed. They need to grow into the possibility of what they're trying to create. So that's how I think about it.

Therapy is different. I'm not a therapist, and if I feel like someone needs therapy, I'll refer them to a therapist, but in the meantime, I may have a conversation with them that may be very therapeutic, and that it can be helpful on a personal level, as well as a professional level.

Daniel Stillman:

Yeah. I'm wondering if we can, this is something that I've, I myself have, I would say, have worked to navigate, to thread the needle in my own coaching between the idea that essence, that everyone has a way of being that is natural and good, that if they can release all the barriers they have, that something will be unleashed, with the growing into.

There is this idea of growing into something more. And I feel like there can be this fundamental tension from, I need to be more, I need to be bigger than, I need to be less than I currently am, I need to tone it down, or be more than I am, with how I am is enough. How do you put those...? Those two things feel intention to me.

Robert Ellis:

So are you asking, how do you navigate when someone comes to you with something that feels too big, or where they're playing too small?

Daniel Stillman:

I think I'm more asking, maybe, more on a meta level of the idea that somebody has an essence, and that means that they are enough. There's also a sense that they want to create something that requires a personal transformation, that they have to grow into something.

Robert Ellis:

Yes. So yes, your essence is enough, but that doesn't mean you can't get better at it. It just means that you, you're good at something, you have something valuable to contribute, and the more you create from that, the easier it is, and the happier you'll be, because you'll be more fulfilled.

Most of us don't think about essence. We tend to discount the things that we're naturally good at. First of all, we're not aware of it, because it comes so easily. We don't pay attention to that.

But yes, if we aspire to something, we may have to grow. A part of growth is becoming more congruent with your essence.

Daniel Stillman:

Yes.

Robert Ellis:

Because, you see, most of us are living and creating from a false persona, which is, I like to think of it as, we're all the solutions to problems that no longer exist. And what I mean by that, is we all have adopted strategies to, again, to navigate life, and to get the attention, and love, and in order to survive. We've adopted strategies that are not authentic, or not congruent with our essence. We've become, to some degree, greater or lesser degree, something that we're not, in order to survive.

So part of growth, is letting go of some of that, and becoming more and more who you are, finding out who you are, and doing that on purpose, creating from that place. But it also is about learning and growing, so we can get better at things that we're already naturally good at, and we may need to learn other things, and we learn and grow as we go on a quest.

Like you said earlier, you can be on a path, or a quest. If you're on a path, you're doing something that you already know how to do. It's fairly predictable, it's not very aspirational or complicated, doesn't require a lot of resource or cooperation.

And so if you're trying to get from A to B, you can just start at B, and reverse engineer it, and it's a project management challenge.

Daniel Stillman:

Yeah.

Robert Ellis:

That's a path.

Leadership is, if you really want to live an adventurous life, you open yourself up to the possibility that the universe knows better than you what you could create, what's possible, and so you go on a quest to find out what's possible. You aim for B, but in this case, B is the best thing that you can imagine, and you conduct experiments, you try different things, and that's how you learn and grow.

Daniel Stillman:

Yeah.

Robert Ellis:

So.

Daniel Stillman:

So.

Robert Ellis:

So.

Daniel Stillman:

Dot, dot, dot.

Robert Ellis:

Does that...?

So that's how I think about it. Growth is, part of growth, is letting go of what doesn't serve you anymore. That's also growth. Part of growth, is learning, and gaining things that you don't already have. That's growth.

And we mostly think of growth in terms of that. How are we going to get bigger? Growth to me is also not necessarily bigger. It's better, more congruent, more resonant, more authentic, more aligned with who I am. The more I create a life that is more resonant, congruent, and aligned, the more fulfilled I am, the happier I am.

Daniel Stillman:

I think that does scratch the surface. So there are a few other layers I want to pull back, and one of them is, how this modality of Coaching from Essence, how you feel it applies throughout an organization.

Because one of the things that comes up in a lot of my coaching work, is an eventual realization of, wow, this is a fundamentally different way of interacting with someone in a conversation to accomplish more than we can imagine, something that's better than can imagine, and many leaders are exhausted from micromanaging, and are not getting the results they want to be getting from their teams.

So I'm curious how you feel, somebody, who isn't a coach, would read Coaching from Essence, and what parts they should be thinking about bringing back to their teams.

Robert Ellis:

So until I write the Book for Leaders, which is the next book that I'm working on, now that Coaching from Essence is published. In fact, I should be getting the proof of the, so the ebook is available now. I think I'm getting the proof of the paperback today, and assuming that it all looks good, I'll hit publish, and it'll be available by the time you post this.

But everything in Coaching from Essence, applies to leaders, or really anyone who wants to create a life they love. Coaching from Essence, is really a loosely connected network of ideas and models, and language for how to create things. That's really all that it is. And everything in the book, with the possible exception of, there's a section called The Red Paperclip, which is about practice building, that will be more of interest to coaches, or consultants, or anyone who is in a service business, and works with clients, but everything else is applicable to leadership.

So we talk about essence. Organizations have essence too. Organizations have, they have a natural way of creating value. Organizations get into trouble when they depart too much from their natural way of creating value, when they try to be something they're not, and that's one of the reasons that most mergers and acquisitions fail, because when you are just motivated by self-interest, status seeking, scarcity, and survival, meaning that you're just trying to make money without any sense of purpose, it's very easy to try to create business, or look for opportunities that have nothing to do with who you are, your core competencies, or anything like that.

So organizations have essence too, and leaders, if Coaching from Essence is a language for creating, what leaders do, is they help people to create things. And like you say, if you don't want to be a micromanager, one of the best things you can do is teach people how to create things.

Another way of thinking about it, this isn't in the Coaching from Essence book, this is what I'm working on in the Leadership Book, is I think of leadership as, most people think of leadership, or entrepreneurship, as sort of climbing the mountain.

Daniel Stillman:

Yeah.

Robert Ellis:

You're constantly overcoming obstacles, and you're climbing the mountain, and eventually you get to the peak where you're going to get to, whatever success it is that you envision.

But really, leadership is about building the mountain underneath you. It's about making, if you're a leader, one of your primary tasks is to make everyone that you work with more valuable. And if you want to grow as a leader, then wherever you are in an organization, and by the way, anyone can be a leader wherever they sit, simply by doing everything they can to make everybody around them more valuable, including themselves.

And so then you think, well, what are the most valuable things that leaders do? What's at the top of the mountain as you move up the mountain, what are you doing more and more and more of?

Well, it really, I think, it boils down to just a handful of things. It's how you think about the future, how you think about impact, systems, strategy, culture, and leadership. And leadership being, how do you do that, how do you help people become more valuable? How do you help people navigate the unknown, on the way to something better than they can imagine?

So that's how I think of leadership, and that's how these ideas can be applied in organizations.

Daniel Stillman:

It's so interesting, because at the core, something my dad used to say, was that, or one of my dad's teachers in truth, but everybody's living their lives according to the precepts of a defunct economist, and every economist has a model of how a person is.

There's this idea of like, oh, we act through self-interest, right? And Adam Smith would say, "Yeah, the whole economy just runs, because it's just all seeking profit, and self-interest." And the idea of how change really happens, and what a person really is, I think is one of the things that's really fundamentally different about your approach, Robert.

Because the idea that everyone has an essence, and it's my job to evoke it, and maybe even provoke it, is very different than the idea that I have to download the correct instructions into everybody in my organization, and build the right matrix, and program them, and it'll just be perfect, and run, if a mechanistic approach, or a computing approach, this is an essence based approach, is a very human approach, and really resonates with one of my perspectives, which is that invitation is the best way to create a change. Not through force, but through somebody wanting to step forward, and that is a very different model for change.

Robert Ellis:

Yes.

Daniel Stillman:

I really haven't thought about, I feel like you've talked about this before in some of our conversations, that organizations can have essence, but it's a profound shift to think, what is the essence here, and how can I evoke it?

Robert Ellis:

Yes, it is a different way of thinking about it. And again, most organizations are very path-like. And by the way, I should, just to be clear here, there's no judgment about this. We are all, both path-like and quest-like. Much of your life is path-like. There should be some parts of your life that are more quest-like, more adventurous, where you're trying new things and learning new things and taking risks. And the same is true for organizations.

Daniel Stillman:

And sometimes, you just want to make tea, and there's a very clear path to making tea.

Robert Ellis:

You just want to make tea, that's great, but then sometimes you want to try something different.

And actually for an organization, organizations, startups are very quest-like, because they don't yet know what works. They're trying experiments. I mean, Lean Startup is a very similar idea. They're trying lots of experiments in order to turn their quest into a path. As you learn, you start turning more and more of your business into a path, so that you can replicate it, and scale it.

But then if you don't continue to have something quest-like, if you're not learning and growing and innovating and disrupting yourself, then eventually, you will lose, because someone will come along, who is more quest-like, and they will improve on whatever it is you're doing, or the market will change, and so you can't rest on your laurels if you're trying to be a successful organization, unless you're doing something that's very much commoditized.

Daniel Stillman:

Who wants to live in that quadrant for very long?

Robert Ellis:

I mean that, it's fine if you do, but I don't think that's very satisfying for most people.

But what you're talking about, yes, many organizations are bureaucratic, they're rigid, there are lots of rules, and policies, and so forth, and as an organization grows, it does need to have a certain amount of that. But that's sort of like, overhead. That kind of overhead, prevents you from being as creative as you can be, so you want to, with all of that, the way I think of it is, you want to have the minimum effective dose. You know, don't want to introduce any more bureaucracy, or policy, or rules than you need to, in order to just prevent chaos.

What you want, is to encourage learning, and growing, and experimentation, and as a leader, nurturing the essence of the people who work with you, so that they're creating the most value with the least amount of effort. And your organization is creating the most value with the least amount of overhead, and distraction.

The other thing, is that we talked about the hidden curriculum, the self-interest, status seeking, scarcity, and survival. Well, what is the antidote to that? I think the anti antidote to that, is essence, abundance, service, and trust.

If you start living your life from essence, what you discover is that you actually have more to offer than you thought. You actually have something of value. You're here to create something that will be helpful.

And really, to me, a meaningful life is, you give yourself away. We're all here to give ourselves away, to express as much of our best selves as we can. And so the more you get in touch with your essence, and the more you're creating from who you are, and again, that's individual, or as an organization, the more you realize how abundant you are, and the more you want to give yourself away, which means you want to serve, you want to create things that are actually meaningful and valuable.

And the trust, is really about trusting that if you do that, the universe will support you. And when I say the universe, I just mean that things will work out, because most of us are afraid to be ourselves, because we're afraid that things won't work out if we don't trust ourselves, or our intuitions, or our natural abilities, or creativity. There's so much pressure to become something we're not. We're being told what we're supposed to do, and if you are trying to create from that, it's very difficult.

Daniel Stillman:

Yes. And I think, one thing that people who are listening to this should, another reason to read the book, trust is one of the thresholds.

Robert Ellis:

That's right.

Daniel Stillman:

Literally, just in a conversation with this morning with one of my clients, laying out the thresholds, and being clear what isn't in the way, and what is still in the way, is really powerful, because I've seen clients get caught at the silliness threshold, or the sanity threshold.

But trust and love are very easy hook points, but not always. Sometimes it is actually, I don't actually know how to do it, and that's fine.

Robert Ellis:

So you're talking about the threshold. Since we're talking about it, just briefly to explain what we mean by that.

The silliness threshold is often the first one that comes up. When I'm talking to someone, and I'm asking them, so when someone comes to me, the first thing that I try to do, is create some value around whatever presenting problem they have.

But then I ask them, "Great, so what would you like to create? So let's say, this wasn't a problem, and you could create anything you wanted. Let's stream together. What would be possible for you? What would you want to create? What are you longing for?" And they'll often tell me some version of, some smaller version of their dream. I think of it as sort of like a bonsai dream.

And nothing against bonsais. I think bonsais are beautiful, but they're beautiful miniature versions of big trees.

Daniel Stillman:

It's just not a redwood.

Robert Ellis:

What's that?

Daniel Stillman:

It's just not, they're not redwoods.

Robert Ellis:

So I want to know, what's the redwood, what's the real dream the person has? Not the dream that their spouse wants, or their parents want for them, or their friends, or their colleagues, or their bosses, or whatever, but what did they actually long for?

Daniel Stillman:

Yeah.

Robert Ellis:

And I often know when I'm getting to the real dream, because they'll tend to laugh, and discount it. That's the silliness threshold.

Daniel Stillman:

Yeah.

Robert Ellis:

It's the fear of embarrassing themselves, or they'll get laughed at, or rejected, or they have a dream that, because it's real, it's a little bit tender. It's something they actually care about, and so they feel a little vulnerable, the more they talk about it. That's the silliness threshold.

So a lot of times, we stop ourselves from doing what we need to do, because we're just afraid to be embarrassed, or what if somebody judges us, or rejects us, or whatever it is.

But then there's the trust threshold... Then there's the knowledge threshold. By the way, these can happen in any order, but often they happen in this order. Then the knowledge threshold, I don't know enough, or I know too much. I can give you all the reasons why something won't work.

Daniel Stillman:

I have to know X, in order to get started with Y.

Robert Ellis:

Everything. And you know my philosophy is, begin before you're ready.

Daniel Stillman:

Yes.

Robert Ellis:

You don't have to know. If you wait until you know everything, you'll never start, because it's impossible to know everything.

Daniel Stillman:

Well, so this is just, if we do do a parenthetical offsite, I wanted to talk about evocation and provocation, probably because I see those as universally applicable leadership skills, not just coaching skills, and that is a provocation to propose to someone, that they can begin before they're ready, is a provocative question.

Robert Ellis:

Yes.

Daniel Stillman:

Right? The questions you're asking when you say, "Well, what's your real dream?" You're trying to evoke a bigger dream from them.

Robert Ellis:

Yes.

Daniel Stillman:

Telling somebody that, that's a bonsai dream, is provocative.

Robert Ellis:

Yes.

Daniel Stillman:

It's a provocation. This is maybe where we go back to, use of self, in the coaching conversation. I'm looking at these two dials of evocation and provocation, and I think it's possible to turn them to 11, and maybe get some noise, some feedback.

Robert Ellis:

Yes.

Daniel Stillman:

That you're pushing someone a little harder, or as our friend Vanessa would say, taking them to your edge, not to their edge.

Robert Ellis:

That's right?

Daniel Stillman:

Which may be your ethos as well.

Robert Ellis:

You want to be careful about, when you're provoking somebody, you want to be careful that you're not doing it out of your need, and you're really being sensitive to where the client is.

So provocation, I'll talk about provocation in a minute, but the way I think of it is, I never push anybody. What I tell people is, "Listen, I'm going to be right with you right here. I'm right behind you. I'm supporting you, and if you stop, I'll bump into you." That's a provocation.

So there are degrees of it. If you think of it as a continuum, one end of the continuum, is what I think of as a disturbing question. I just ask a question that might be a little uncomfortable for somebody. And then a provocation is there's a continuum where it gets a little bit hotter.

And then if you were to graph how much heat you apply, and there's kind of a curve, a disturbing question is low heat, and a real provocation is higher heat, the Y axis is trust.

Daniel Stillman:

Yes.

Robert Ellis:

So if I don't know someone very Well, I won't be very provocative, usually. I might ask a disturbing question.

Daniel Stillman:

High trust, high heat, is, you're still in the safe zone.

Robert Ellis:

High trust, high heat.

Daniel Stillman:

Low trust, high trust.

Robert Ellis:

So when I have trust, that can be a recipe for disaster.

But one of my very intentional aims is to create high trust with my clients. That's critical to doing deep, powerful work as a coach. So I do everything I can to let my clients know that they can trust me, and once I've built trust, then I can be more provocative.

So let's just talk about what we mean by evocation and provocation. Much of coaching, or much of the way that many coaches think of what coaching is, is that it's evocation, right? It's asking good, open-ended questions, using your curiosity, doing active listening, and so forth, and drawing the client out.

Daniel Stillman:

Tell me more about that.

Robert Ellis:

Yeah, tell me more about that.

And based on the idea that the client already is, I forget the phrase, full, and complete, and has all the answers and everything, but I don't really subscribe to that philosophy.

But yes, we're all whole, but you know something I don't know, and I know something you don't know, and so, there's nothing wrong with me giving you some things to think about that you wouldn't, would not otherwise occur to you, and I do that as a coach. Some people call that advice. I don't really think of it as advice, because I can't tell anyone what to do, but I can offer many things, often, valuable and helpful things that someone can think about, and then they can make their own decision.

So a provocation is an invitation. It might be a challenge for someone. It might be a statement of belief, that I believe they're capable of something that they're maybe not sure they're capable of, and so I encourage them to conduct an experiment.

When someone comes to me, and they tell me their dream, my role as a coach is to believe them, and to remember. And so when they forget, I remind them, "Hey, you have this dream, and I believe you. You told me you had this dream, and I believed you. And furthermore, I believe that you're capable of creating, if not that, something better than you can imagine. And so I encourage you to go on that quest, and I encourage you, here's some experiments you could try."

So that's a provocation.

Daniel Stillman:

Yeah.

Robert Ellis:

It's a challenge. It might be a challenge to their beliefs, or their identity, their values, or their idea of what they're capable of.

Daniel Stillman:

Yeah.

Robert Ellis:

Yeah.

Daniel Stillman:

Well, that was a long parenthesis. I think we may have covered the basics of the thresholds, and people, they should just buy the book, and they should just read it.

So I don't want you to have to-

Robert Ellis:

They're all in the book.

Daniel Stillman:

I know you're in the mood to give everything away, Robert.

Robert Ellis:

I do. I never sandbag. I never hold back.

Daniel Stillman:

I think, one thing, that's... Another one of your favorite models that I want to bring into the conversation, because it's connected to the idea of navigating uncertainty, way back in the two beats ago, three beats ago in our conversation when you were talking about leadership as creating something better than we can imagine, and paths versus quests, and getting caught in productization versus trying to create something truly unique.

I feel like this goes to one of your models that I find perennially useful, which is the futurosity continuum. And I was hoping you could sketch, we can sketch it a little bit, but where I find it generally very useful for leaders, owners of businesses, is just the realization of the difference between reactive and proactive, and the difference between strategic and emergent. I feel like reactive to proactive, is maybe the basic practice of realizing like, "Oh, wow, there's more." Of course, when people see the continuum, they go, "God, I'm caught here, and I want to be here," and then realizing that there's more layers to creating what they really want to create.

I'm wondering if we can peel back some layers on why it's important to make time for strategic thinking, and emergent thinking, and how we can never get that time if we're caught up just in reactive and proactive thinking.

Robert Ellis:

Yes, I will try to sketch it out. I mean, the futurosity continuum is a visual model.

Daniel Stillman:

And I'll put an image of it in the...

Robert Ellis:

Okay. Okay.

So, again, if you think of a continuum, right? So the futurosity continuum, and the reason it's called the futurosity continuum, is that, basically, what we're trying to describe is, what is your stance toward time? Are you creating from the past, or are you creating from the future?

Okay, so the continuum goes from the past to the future, and it starts with reactive. Reactive, meaning, something happened already and now you're just reacting to it, and you're putting out fires, or you're just in problem-solving mode. You're just reacting. You're not in control. You're just reacting to things that have already happened, so that it's very much, you're trying to manage the past.

Daniel Stillman:

Which is a really hard thing to do, by the way, given that it's already happened.

Robert Ellis:

It's a hard thing to do, right? Exactly.

So now, you're trying to fix the past, okay? You're a fixer, if you're reacting, or you're proactive.

Proactive is just, so something has happened often enough that you finally catch onto it, and you say, "Okay, let me see if I can avoid that happening again." That's proactive, but if you're reactive or proactive, you're still responding to the past, so you're what I call a fixer. That's a fixer.

After proactive is opportunistic. Once you start to create from the future, in other words, once you start to move towards something you think you want, once you start creating, you will create all kinds of possibilities. Some of which, will be aligned with your quest. They'll be directionally appropriate for what it is you're pursuing, and others that are shiny objects, they're distractions. And this is one of the problems that leaders and entrepreneurs, especially, can fall right to. So, opportunistic, but at least now you're moving toward the future. You're creating possibilities, that didn't exist before, that might lead to something good.

Strategic. The way I define strategic, is you're intentionally setting about creating a future of your own choosing. So you have an idea of what you want, and now you're taking action to create what it is you think you want.

And again, if you're on a quest, you don't know it's possible, but you have an idea of the best thing that you can imagine, so being strategic, is intentionally taking steps to create something, the best thing that you can imagine. Okay.

Then beyond strategic, is emergent, which is, now, you're in conversation with the universe. In other words, you're paying attention to what results you're getting, what response you're getting, and so you have to pay attention to weak signals. You're noticing just what's showing up for you, and you're seeing whether or not some of these things, whether or not you're creating possibilities now, that are potentially better than you might have entertained before.

Daniel Stillman:

Yeah.

Robert Ellis:

So the difference between emergent and opportunistic, is that opportunistic is kind of random, and emergent is things are responding to what you're putting out. You're more intentional.

I'll give you an example of that. Coaching from Essence. For me to train coaches was entirely an emergent phenomenon. I never had any intention of training coaches.

I was very happy as an executive coach, and I was very much working on creating myself as a powerful executive coach, and what happened was, I was meeting with some success, and I had a lot of friends who were coaches, and so word got out, and people started asking to meet me for coffee, or lunch, or whatever, because they were either thinking about becoming coaches, or they were coaches, and they weren't very happy with the work they were doing, or they weren't creating the success in their practices that they wanted, and so they wanted to pick my brain.

And so after a few people did that, I thought, "Wow, this is really interesting. This just sort of happened out of nowhere. Maybe I should offer something for coaches."

And I had no idea what that offer would be, but I just posted something on Facebook, and within two days, 21 people signed up for training that didn't exist. See, I began before I was ready.

Daniel Stillman:

You did, and I think there was also some essence there, too, right? There was a hunger to connect.

Robert Ellis:

Yeah.

Daniel Stillman:

You weren't just blindly following signals. It wasn't just opportunistic.

Robert Ellis:

No, no.

Daniel Stillman:

This is-

Yeah, sorry, go ahead.

Robert Ellis:

Well, yes, I mean, I had an idea of my essence, and I had an idea of all the things that I was learning, and I had been developing some of those ideas, and teaching many of these ideas to leaders at Singularity University. I developed and led the leadership track for the Global Startup Program at Singularity University, and some of these ideas were sort of road tested there, but I never had any idea of teaching coaches.

So that was very much emergent.

Now, if you can visualize that continuum, again, that's the X axis, the Y axis is time, energy, and resources. So most people, and most organizations, if you were to plot the curve, it's very high on the reactive, end of the continuum, and very low on the emergent end of the continuum. In other words, most of us, and most organizations, are devoting a lot of their time, energy, and resources being either reactive or proactive.

Daniel Stillman:

Yeah.

Robert Ellis:

They're firefighting, putting out fires, solving problems, and relatively less and less time being opportunistic, strategic, or emergent.

The ideal curve, is probably the reverse. You will always be spending some time being reactive, because we can't always predict the future. There will be problems that we didn't anticipate, and we'll have to respond to those, but ideally, the curve would go the other way, where you're spending more of your time and energy being strategic and emergent. You're intentionally, creating possibilities for yourself.

Most startups, it looks probably more like a bell curve, because they're nothing to react to, since they're just starting. Things aren't emerging yet, because they haven't created anything, so they're being proactive and strategic. They have ideas, and they're conducting experiments, and so most of their time, energy, and resources, goes into just conducting experiments.

Daniel Stillman:

I'll put a sketch of this in the show notes for people to look at while we're talking about this.

Robert Ellis:

Sure.

Daniel Stillman:

I feel like there's never been a time when I haven't drawn the futurosity continuum for somebody, where I don't feel like anybody has the optimal distribution, generally speaking.

Robert Ellis:

Sure, and it's changing all the time. It's always changing.

One of the universal challenges as an executive coach, is that if you're working with leaders, one of the things they're always having to negotiate, is how much their time, energy, and resources being sucked toward the fixer-end of the continuum.

They have a vision for the future, and they're trying to create it, but they're often being pulled for the other end of the continuum, and they're starved for the time, and energy, and resources for creating.

Daniel Stillman:

Yeah.

Robert Ellis:

And so, that is something that we do problem solve around.

Daniel Stillman:

So this is, to go back to one thing you said, and I can't believe we're... The time goes really fast, it's crazy.

The idea that strategic intent, is speaking to the universe, and the emergent space, and the continuum, is listening to what's really going on.

Robert Ellis:

Yes.

Daniel Stillman:

And I think people, the first version of this diagram that you made, didn't have emergent, because strategic, for many executives, feels like this is the pen, this is the ultimate goal, is to be strategic.

Robert Ellis:

That's right.

Daniel Stillman:

But of course, being strategic, means also finding out whether or not the strategy is working, and what the universe really wants of us.

Robert Ellis:

That's right.

Daniel Stillman:

So this idea of speaking to the universe, and listening to the universe, is just, I would love for you to stay a little bit more about that.

Robert Ellis:

Well, yeah. I mean, think about strategy, and strategic planning, the idea of strategic planning is just an interesting one. Let's just say, right?

Daniel Stillman:

Do you want to have one more word? What's the word you really want to use, Robert?

Robert Ellis:

You have an idea of what you want to create, and you're saying what you want to create, so it's a monologue, in a way.

You're saying, "Look, here's the plan, here's what we want it, and here's the plan, here's how we're going to create it." And that's very path thinking.

Now, it can be strategic to do premortem, right? To say, "Okay, we're aiming for this." By the way, I'm not a big believer in OKRs, or things like that, because in my experience, every client I know who uses OKRs, they're so prone to, first of all, to identifying the wrong OKRs, for example, common one might be, how many customers we're going to get.

My point of view is you should just optimize for one customer, or you identify who your customers are, and optimize for each of those different kinds of customers, or those personas.

How many you get, you don't know. You don't know what's possible, so it's not very meaningful to think that, picking a number out of a hat, is going to really inform your action.

So you aim for something, you have a strategy, you have an idea of what you want to create, and you put that out, you ask for that, in a way, but then you have to listen, and learn, and see what response you get, and that's emergent.

So when you are moving toward emergent, you're entering into a conversation, which means that, yes, you have an idea of what you want to create, and you take action based on what you think is possible, but you're very much open to learning, and listening, and observing, and seeing what you get in response, so that you might discover something else that's possible.

That's how you get to something better than you can imagine. That's one of the ways.

Daniel Stillman:

Yeah.

Robert Ellis:

My favorite way is to optimize for serendipity, but-

Daniel Stillman:

That's another conversation.

Speaking of which, I've used up all of the time we have allotted to this conversation.

Robert Ellis:

Oh, no.

Daniel Stillman:

What haven't I... If you can go one more moment, because we're literally on the wire, and I want to respect your calendar, Robert.

Robert Ellis:

Sure.

Daniel Stillman:

What haven't we talked about, that we should talk about. What is the question that I have not asked you, that I ought to have asked?

Robert Ellis:

You haven't asked me, why? Well, we did touch on it. The why. Why is this important? What is this about? Is it about just being more successful, or making more money, or something like that? And we did touch on it.

Obviously, we don't have time to, say, go into the Hero's Journey, but that's such a popular model that so many people talk about, in terms of leadership, and so forth, and I think many people misunderstand what the Hero's Journey is really all about.

The Hero's Journey, is not an individual journey of overcoming obstacles in order to get some boon to elevate yourself. It's not about self aggrandizement. The whole reason for the Hero's Journey, is to get something that is of benefit to the community.

And that's really how I think about essence. Essence is not about becoming yourself, so that you can just entertain yourself and be content. The journey to getting in touch with your essence, and creating a life from your essence, is so that you're giving yourself away. You're sharing your best self with the world, and think about how different the world would be if everybody did that.

So that's really what this work is about. That's what it's about as a leader, and building the mountain, how can you elevate everyone else around you? How can you create a venture that creates value for the world, so that you're doing something meaningful that actually improves the world? That's what interests me.

Daniel Stillman:

Yeah. I think a world where everyone can express their essence, building organizations where people can express their essence, designing meetings, gatherings, spaces where that can happen, is a transformative, that's not a path, that's definitely a quest, and I think it's a worthwhile transformation.

Robert Ellis:

that's right. And as you know, connection is so important, and you're so good at creating connection, facilitating connection, and connection happens through conversations. When we can talk about things that matter, then we can connect at a different level, and we have an opportunity to express more of our best selves, and so, that's why conversations, and facilitation, and coaching, I think, are so important.

Daniel Stillman:

Well, Robert, where should people go to learn about all things, Robert Ellis, to find more about your work, and to find copies of not just this book, but-

Robert Ellis:

Yes.

Daniel Stillman:

The sequels.

Robert Ellis:

Coaching from Essence is now available on Amazon. It was written for coaches, but really, if you're a leader, or an entrepreneur, or you just want to create a life you love, there will be something in the book that will speak to you.

I am working on the Book for Leaders. That'll be next. I'm hoping to have that out by the end of this year.

If you want to know more about my work as an executive coach, you can go to futurosity.com. If you want to learn more about Coaching from Essence, if you're a coach, go to coachingfromessence.com.

And by the way, I should mention that, giving myself away, I have given the entire Coaching from Essence Program away. In fact, I've given three complete programs away that were recorded on Zoom. You can go to Coaching from Essence, and join the Coaching from Essence community, completely free, and you can watch over 100 hours of videos of the entire course, masterclass, client creations, sprints, and connect with a community of over, I think it's around, 400 extraordinary coaches now, so it's all completely free.

Daniel Stillman:

Yeah, you could spend weeks absorbing it, or you could just read the book, which is very handily dandily packaged up.

Robert Ellis:

Or you could read the book.

Daniel Stillman:

Yeah, it's like spending a really nice afternoon with you.

Robert Ellis:

Yeah, I wrote the book, so that you could have it in your hand, but the entire course is available for free. I think the world needs more coaches. I'm trying to facilitate that.

Daniel Stillman:

Well, at every level, in every organization.

Robert Ellis:

Yeah, yes.

Daniel Stillman:

I think.

Robert, you've been exceedingly generous to me with your time today. I love the book. Reading the book, was obviously like taking a warm bath, because I've been exposed to your thinking, and I've been in conversation with you for several years now, but I still loved and enjoyed the book, so I'm really grateful that you made it real. Thank you.

Robert Ellis:

Thank you. I appreciate that.

Daniel Stillman:

Well, I will call scene.

How to Think Strategically about Funding for Founders and Investors

I first met Avantika Daing, a General Partner & Managing Partner at Plum Alley Investments (and Tedx Speaker!) while she was onstage at an Entrepreneurs Roundtable Accelerator event. She was there to share a bit about Plum Alley’s Investment thesis as well as unpack six pitches live from early-stage companies.

Let’s level set a bit so you understand Avantika’s and Plum Alley’s mission, which revolves around an important number that hasn’t moved much in years, despite a lot of effort - 2%. 

According to Pitchbook, in 2022, companies founded solely by women garnered just 2% of the total capital invested in VC-backed startups in the United States. Plum Alley only funds gender-diverse companies and works to create an ecosystem to help them not just get funded, but to grow and succeed. That’s one of the reasons I wanted to bring Avantika on, to share some of her ways of thinking strategically about funding as an investor, how Plum Alley is working to create a more sustainable funding ecosystem for diverse founding teams, and how she coaches founders to be more strategic about funding, too.

Watching Avantika on stage peel back the layers of the onion (one of her favorite metaphors!) on a company’s story in conversation with a founder and work to understand the company’s potential was fascinating - it’s a tremendous act of intellectual rigor and curiosity. Her questions also reminded me that founders can make an investor’s job a lot easier through more powerful and intentional storytelling.

Another powerful metaphor that Avantika came back to in a number of pitches was the idea of a Basecamp.

In other words, Avantika, as a funder, wants to know: Is your company building a core technology or defensible market position (a basecamp) that will provide you with multiple paths to success? 

Avantika acknowledged that a “single story” about how your company will “win” or “summit the mountain” is powerful, but she was clear that she prefers companies that are creating a powerful “basecamp”...why? Because:

🏒A “many shots on goal” strategy can help create longevity and increase options for success.

I’m so grateful that she was willing to have a longer conversation with me on the record to explain her ideals about storytelling and the basecamp-summit metaphor.

She also helped peel back some layers on another idea she loves to coach founders on: “Dressing their cap table” for sustainable success from seed to IPO and well beyond - since capital needs don’t stop at IPO.

I love how Avantika’s metaphors shift, refocus and redesign the conversation about pitching, funding and sustainable success for startups.

Enjoy this conversation as much as I did!

Links, Quotes, Notes, and Resources

Plum Alley

Avantika's Tedx Talk: There is No Balance. There is Juggling

Daniel’s LI post on Avantika’s Entrepreur’s Roundtable Session, highlighting key questions and perspectives from Avantika, including the “base camp/summit” metaphor.

Summary

4:10 Data shows that less than 2% of companies that went public over the last five years were female founded

7:02 Plum Alley’s Venture platform will provide portfolio support, plug into investment world, and move the needle for diverse entrepreneurs, investors, and institutions

19:36 Avantika explains her concept of "Dressing the Captable" which involves strategically thinking through who to give equity to and who not to give it to, in order to set up a company for success

25:26 Thinking about the long-term arc of a conversation when it comes to venture capital

29:35 Avantika proposes a platform approach where the best investments stay within the platform and create the highest level of investor returns

Key Quotes

Minute 2

Avantika Daing:

So the number that's been existing in the VC world is about the percent of venture capital funding that goes to female founders. That is the 2% number that has been historically referred to. What we did at Plum Alley, and this is partly leaning on my two-and-a-half plus years of operating experience, plus having taken a company public, directly being responsible for two IPOs, indirectly being responsible for another IPO. What we're looking to do is look at the IPO landscape, and work backwards. And the why behind that is about disrupting wealth realization. It's a word we made up, and what wealth realization really means is wealth creation, and then distribution. Wealth is often created by generational wealth, so you're born into it.

Or the other alternative is to have a technology company take placement in the IPO market. So those two are usually the trajectories. Not the only, but usually the trajectories for wealth creation. What we are looking at is taking that further, into wealth realization, and really changing the face of IPOs. So the 2% number you mentioned is important, but it's a new narrative, and that 2% number to be very specific reflects the 1100 plus new IPOs over the last five years that occurred on New York Stock Exchange and Nasdaq, where only 2% of that, female founded IPOs.

So if you look at it from moving backwards in what needs to be done, we realize very quickly that the needle hasn't been moved, and there's some very ingrained systemic biases that exist that need to be changed from the perspective of wealth realization, to really move the needle on redistribution of capital on any aspect or spectrum of diversity.

Minute 18

Avantika Daing:

I'll just quickly plug in. About 70% to 80% of female founded companies, specifically, exit through an M&A route over an IPO. And I have a whole theory about that which is, look, none of it's easy. So, anyone, congratulations to anyone who can take it to an M&A stage. But the stakes and the motivations are not aligned. And so, bankers and founders are motivated to take the nearest, quickest exit, versus having the right mental capital infrastructure, platform support for taking it further for a handful more of years. Somewhere between two, five and 10. It's not easy to staying on that IPO route, and that's the needle we need to move

Minute 52

Avantika Daing:

I would probably say the two things are learn to say no to your customers, as well as investors, to be hardball on your strategy.

And there are two different types of strategy when you're ... One is focused on revenue. If you are a multi-year SaaS contract with a hardware component build in, and you've got customers saying, "Well, I'm not sure I want to pay for three years. I want to do a pilot for six months, and I don't want to pay you, and then I'll scale up, and then I'll do a contract for one year." You got to walk away from that. There are ways in which you can accommodate that, but you cannot be creating exceptions, especially early on. It's a flip of mindset, and it's nerve wrecking to think ... Most people think early on, "Oh yes, I've got a great enterprise. Logo, top 500 public company coming, why would I want to keel over?" Well, you need to set precedents, and you need to set the right precedents. You have to be a bit strategic.

I'm not saying you shouldn't accommodate for those asks, but be strategic in how you create that construct. So, for a pilot, you build a pilot in. If they like the word, "Pilot," you give them pilot, but you make it monetizable. If they want to backhand, you have to understand, again, peeling the onion back, understanding where their motivation is. And the motivation there is, large enterprises like to say, "We want to first test you, and then backend payment." How do you build that into a construct of establishing your contract, and the nuances that go into the contract that set you up for monetization.

There's a component of learning to say, "No," with a creative element of accommodation. And then the second part of, "No," is to your investors. Early investors ask for side letters. They ask for preferences. You want to set yourself up for success for later rounds, and you want to be conscious of what construct and precedents you're setting with your investors now. And having conviction and motivation on yourself in not reducing your valuation, or not wanting to give up too much ownership, whatever it might be for you as a founder or founding team, sticking with your narrative is extremely important.

Minute 56

Avantika Daing:

And then, the last thing I'll say is very important. It's not done enough, and it's completely underestimated, which is think two steps ahead. Also, a different version of peeling back the onion. But if you're raising seed, think about Series As and Bs. If you're raising As, think about Bs and Cs, and why? Look at the market today.

Some of our portfolios that we've worked very closely with when they were raising the Series A, we very quickly came in and we said, "Now is the time to bring in non-dilutive capital. Meet, they're friends of ours, X, Y, and Z that are interested in funding you. Giving you a line of credit, giving you a debt vehicle if you're a Series B," bring that in. Unfortunately, you're not thinking that, because you don't have a need for it. [inaudible 00:56:58] Founders would say, "Well, I have a runway of 18 to 24 months, why do I need to think about that? I've got to runway for 36 months. Why do I have to think about it?"

"Yeah, great. I'll take the introduction, but I'm really not going to lean in. I'm too busy now trying to close my [inaudible 00:57:14] later." Well, later becomes too late, because you cannot time a situational market. And a situational market for us is a COVID. A [inaudible 00:57:25] for us is consideration towards a down market. And so, to manage situational markets, when you are doing your equity round at the back of it is the time to come in and put creative financing vehicles in place. You may never need it. You may end up paying a bit, which could be the downside. But frankly, you're never going to lose out on using, and having that as a backup in creating financial health. And really, frankly, drawing that back to your own mental health in using it as a tapping mechanism.

More About Avantika

Avantika Daing spearheads Plum Alley’s strategy and investments towards deep tech and novel science companies with gender diverse founding teams. Plum Alley has raised over $60 million across 30 companies including Mammoth Biosciences, Einride, Air Protein, AiFi, Diligent Robotics, One Concern, Shine and Biobot Analytics. The Portfolio boasts of two unicorns and one exit. Plum Alley offers LPs and individual investors the opportunity to invest in diverse early stage private companies that are transforming the world.

Avantika brings proven leadership across business functions, operations, and executive management for both start-ups and Fortune 1000 companies. She has a unique combination of an institutional grade reputation with a grassroots approach to building enterprise software, customer focused GTM, and platform businesses.

Avantika’s experience in private and public companies covers the healthcare and technology sectors. Her professional experience spans nearly 30 years, as both an executive and a founder, with responsibility in management, product development, business development, operations, M&A and IPO. Prior to PA, she was the Chief Revenue Officer at Jopwell, Andreessen-Horowitz backed. She served as the Chief Growth Officer at Zomato/UrbanSpoon, Temasek, Sequoia, and ANT Financial funded, which grew to $1.3 Billion in valuation during her leadership. She also founded a venture-backed, international SaaS marketplace. Avantika was the first commercial employee at Eyetech Pharmaceuticals, where she helped grow the company to IPO (NASDAQ) at a $735M market capitalization in 3 years.

Avantika is a TedX speaker and speaks on Venture Growth and Entrepreneurship, Investing in Female Founders, IPO, and Intentional Investing. Avantika currently is on the Board of TiE, New York.

FUll Transcript

Daniel: Well, welcome to the Conversation Factory. I hope we can have a good talk as the title of my book goes. Listen, I was really excited to host this conversation with you. Partly because that experience at the ERA Round Table when they did that process for the final pitch, where everyone stood up who wanted to pitch a company, and you could ask a question of any of the group to sort of filter out. No crypto exchanges. And the statement you said is, "If you do not have a diverse founding team, if you do not have a female on your team, sit down."

I got goosebumps. I still get goosebumps thinking about it, because it's such a powerful statement. I want to just start there, because of the number 2%. It's a really important number, 2% of female founders of all of ... In the VC IPO exits, and regardless of all of the efforts that people have been putting in over the last years, that number hasn't moved a lot. Can we just start there, and say why is it important to move that number, what's been done and what aren't we doing that we ought to be doing to shift that number?

Avantika Daing:

Well, let me start by first saying thank you Daniel for having me here, and giving me the time and the airspace, if you will, for having this conversation with you. I will say my engagements with you are very exemplifying of your topic, of your book, of a good talk. I'm really looking forward to-

Daniel Stillman:

Thank you.

Avantika Daing:

... the hour here. I'm sure we're going to be jumping around on many different topics, but excited to at least bring to the surface some of the questions that the world at large should be asking, but more specifically certain industries, such as the venture capital industry, the entrepreneurship industry, the ecosystem at large, towards supporting entrepreneurs. Thank you for picking that up. That wasn't orchestrated. It just kind of came out, and it came out very naturally, and I didn't overthink it because of what we do. And so I'm going to start there.

I'm one of two founding partners of Plum Alley Growth Venture, where we focus on investing in frontier technology. More specifically deep tech and novel science. So far our stage focus has been Series As and some Bs, and I'll get into why we've been conscious about coming in at Series A, versus either before or after. Our investment thesis, in addition to being focused on sector and stage, is wrapped in a gender mandate. I say wrapped in a gender mandate, because we don't start there. We look for gender diverse teams after we've identified that there's a sector, an industry, a company we want to invest in, a founder we want to invest in. And after we've done our diligence for a Series A company where we can see the line of sight of initial revenues having a trajectory towards scale and growth. And so, our thesis is very specific in our thesis of investing in frontier tech, supporting gender diverse founders.

We also do ourselves a favor as pickers, as VCs, investing in early stage companies in cutting out the noise. And by [inaudible 00:04:55] I mean cutting out, seeing too many investment opportunities, trying to find that needle in a haystack. But also, cutting out the noise if you will, with complete due respect to all my friends who've participated in elevating the narrative around diversity at large. Be it driven through ethnicity or gender, is cutting out the noise of where the rubber meets the road. And if I can take another quick minute to just explain what I mean about that?

Daniel Stillman:

Yeah, totally.

Avantika Daing:

We've been, and being very analytical in my upbringing and in my career of 25 years prior as an operator, plus converting into venture for the last six years in a professional manner, we've seen a lot of support and narrative. More now in the last three, four years, than ever before on diversity at large.

And that narrative comes from a complete shift in our society, supported by COVID, BLM, MeToo, a handful of other, I would refer to them as platelet shifts in our societal thinking. The new generation, I've got two kids that sit in it. They completely challenge traditional thinking, but it's also been supported by capital. You've got large banks, you've got large institutions who are putting somewhere between half a billion to a billion at work on a diversity thesis. You've got folks like us in VC at Plum Alley. But also others that have different ranges, and sort of USPs, their uniqueness in why they support gender, or diversity, or ethnic diversity at large for investing. So, a lot of capital, a lot of support, a lot of social fabric reconstitution happening in our society. However, when you look at the data over the last 10 years, and we slice the data over a 100-year period, over a five-year period, and then over a two-year period to understand if there are any sort of blips, peaks and troughs that would also tell a separate story.

And if we look at the data over the last 10 years, it's really sad to say that we haven't been able to move the needle. And I'm saying the collective, "We," right?

Daniel Stillman:

Yeah.

Avantika Daing:

And so, it begs the question which is, well, what's been happening? Because there's been a lot of energy, a lot of support, a lot of capital. And I think on the capital front it's easier to talk to, because data is data, is very binary. We're seeing that there is a good amount of distribution. At least in the venture space, of capital in early stage. And by early stage, I mean pre-seed and seed, going to gender diverse founders. So about roughly 23% of venture over the last two years goes to gender diverse founders. We've got data over five years and 10 years, two years is the best looking data, which is why I'm sharing it here.

But unfortunately, as you look up the value chain, as they say in VC, which means Series A, Bs, and later stage getting to liquidity and IPO, where wealth realization, wealth creation really happens, we see that number being halved and further reduced, right. So, in that 2% number you mentioned, it's important to clarify that there's a narrative that's been existing in the VC world for a long time now, which they do refer to the 2% number, but it's a different 2% number.

So the number that's been existing in the VC world is about the percent of venture capital funding that goes to female founders. That is the 2% number that has been historically referred to. What we did at Plum Alley, and this is partly leaning on my two-and-a-half plus years of operating experience, plus having taken a company public, directly being responsible for two IPOs, indirectly being responsible for another IPO. What we're looking to do is look at the IPO landscape, and work backwards. And the why behind that is about disrupting wealth realization. It's a word we made up, and what wealth realization really means is wealth creation, and then distribution. Wealth is often created by generational wealth, so you're born into it.

Or the other alternative is to have a technology company take placement in the IPO market. So those two are usually the trajectories. Not the only, but usually the trajectories for wealth creation. What we are looking at is taking that further, into wealth realization, and really changing the face of IPOs. So the 2% number you mentioned is important, but it's a new narrative, and that 2% number to be very specific reflects the 1100 plus new IPOs over the last five years that occurred on New York Stock Exchange and Nasdaq, where only 2% of that, female founded IPOs.

So if you look at it from moving backwards in what needs to be done, we realize very quickly that the needle hasn't been moved, and there's some very ingrained systemic biases that exist that need to be changed from the perspective of wealth realization, to really move the needle on redistribution of capital on any aspect or spectrum of diversity. Sorry, that was more than you asked for, but I just-

Daniel Stillman:

No, that's the big picture, and I want to go into the leaky bucket. So two things that I was thinking about is, one is, is the falloff rate from seed to IPO higher for females? Or in diverse teams, are they not accessing capital later on in their cycle at a worser rate than male founders? Is that what you're also saying, is that the decay rate from seed to IPO is faster. And so, this is why when you talk about intentional investing, and thinking about a platform approach so that the bucket isn't leaky, that we're actually getting people from seed to IPO successfully across the whole lifecycle. Is that right?

Avantika Daing:

You're absolutely right, and I've heard the argument now in my current role as a VC over the six years, but also in my role of being an entrepreneur, and also in my role of being an early [inaudible 00:12:44] of a very large biotech and technology startup that IPOed each for a billion, and then double-digit billions. Where it's the wrong question to be asking, and the wrong question to be asking is, is there enough supply? Do we have enough high quality, diverse founded teams to be investing in at late stage? For private equity to be involved, for venture capital to be involved, for investors that look for a higher liquidity profile Series B and beyond to be involved?

And I think it's the wrong question, because I don't believe that, that is the stopgap, or the bottleneck. If you look at, and I don't want to spend too much time because that could be a topic by itself, but if you look at where the talent pipeline begins, the talent pipeline begins, especially in frontier tech investing, which is a sliver of all of tech.

It begins at the education level. It begins in undergrad, in masters. If you look at the percentage of students that have female students, excuse me, going into STEM. Be it medical fields, bio-engineering fields, genetic fields, pure engineering, new age, new materials, applied materials, and kind of new age degrees, if you will, that are relatively new opportunities that didn't exist about 10 years ago. We're seeing an influx of talent, and that talent [inaudible 00:14:23] ranges from 30, 35%, all the way up to 50%, right?

If the talent pool is strong, and the startup community is strong, then rethink the question you're asking. They're inherent biases. Private equity looks like a certain type. Venture capital that does late-stage venture capital looks like a certain type. They sure don't look like me. They short on sound like me, right?

Daniel Stillman:

Yes.

Avantika Daing:

And I would encourage everyone to look at my LinkedIn to see what I look like. But I'm a woman of color, that is a first generation immigrant, that had to earn my stripes, was not fortunate to go to tier one ivy-league schools, at least for undergrad. Got the opportunity to do it for postgrad. And so, my story is not very linear. And [inaudible 00:15:16] speak for the best founders out there. It doesn't have to be ... We've invested in MIT startup founders. We've invested in Nobel Laureate founders. We run the gamut, right? The point to be made is that where we come from, we're not born with the systemic biases by default, of me and my partner looking very different, coming from different continents, having different experience.

She's a Wall Street queen, having spent three decades there. I'm an operator, so we bring diverse experiences to the table, and we don't bring those systemic biases. Our thought process is different, which means that our [inaudible 00:16:11] is going to be different. Now, one can argue that we bring different sets of biases.

Daniel Stillman:

Sure.

Avantika Daing:

And yes, that's true. You need those to balance out the systemic biases that exist. When you talk about the leaky bucket syndrome, you are absolutely right. I think we're seeing a good amount of energized funding in venture, supporting diverse founders at early stage. Even at Series A, [inaudible 00:16:35] we see a very marked decline when it comes to Series B. And then, we continue to see that decline to half its rate and beyond as we look at Series C, and later stage.

We really, it's not just we need to, we have to, because if you think about it from an economic viability perspective, as an economist would, the economy is not set up at a fundamental level for sustainability. You mentioned platform, and I'm going to come to that. And what we mean by that is that there is no product out there, AKA, a platform, that can support the lifecycle needs of diversity at scale as diverse founders go through the different lifecycle needs of capital from early to late. [inaudible 00:17:34] beyond capital, finding the right partners for support pre-IPO. It doesn't matter, we kind of refer to it as a ecosystem support.

It varies. The type of services, consultation, business development, capital that you need from stage one, to stage two, to stage three [inaudible 00:17:55] vary. And so, the idea is to create a product, a platform that supports that, that eliminates and prevents the leaky bucket syndrome that happens in venture. But in that, also creates a fabric for setting up economic viability, because if you play the platform forward, and you provide the right kind of capital construct, but also ecosystem support construct, then these founders, diverse founders that actually are able to IPO and prevent the shortcut into M&A, are able to create wealth and then pump that back into the platform. Thereby, creating a cyclical cycle of wealth realization.

I'll just quickly plug in. About 70% to 80% of female founded companies, specifically, exit through an M&A route over an IPO. And I have a whole theory about that which is, look, none of it's easy. So, anyone, congratulations to anyone who can take it to an M&A stage. But the stakes and the motivations are not aligned. And so, bankers and founders are motivated to take the nearest, quickest exit, versus having the right mental capital infrastructure, platform support for taking it further for a handful more of years. Somewhere between two, five and 10. It's not easy to staying on that IPO route, and that's the needle we need to move-

Daniel Stillman:

But the payoff is huge, if they can-

Avantika Daing:

Payoff is huge.

Daniel Stillman:

If they can strap in for a little bit more of that. There's so many layers here that I want to peel back, and I want to think about what messages founders need to hear at what time. I want to put this all in the context of conversation, because that's my ax to grind. Certain VCs only want to be having certain types of conversations. "When you're at this stage, come talk to us. When you have this, come talk to us." And after that stage, or before that stage, there's no conversation to be had. What you're talking about is pulling back and saying, "We want to be able to continuously be in dialogue with you across the whole process, to the finish line." But then also beyond. That's in our last conversation we talked about. Even after IPO, how do they learn to grow their company?

That's what I'm thinking about is what a founding team needs to know to learn to be hearing what's easy or hard for them to hear at each one of those stages. That a platform would be saying in their ear, "Now you're ready for this. Now you're ready for that." Where do you feel like the dips are in that process that a platform can deliver the right messages to them? One I just heard is, "Wait a little longer. We can get you through this period to the next stage," and that sounds like a really powerful message. What else do they need to hear that they are not getting as without a coherent platform set of messages?

Avantika Daing:

Before, Daniel, I answer your question, I just want to say two things on the topic of conversations. All good VCs have conversations. They actually start having conversations with potential ... With entrepreneurs and potential investments early. All good VCs are in the business of having conversations early. The second thing I'll say, it's actually a good thing for VCs to have an investment thesis that's specific, right, because you really need to focus on portfolio construction to drive portfolio returns, to then focus on investor returns. All of that is very important, because your track record in terms of investor returns, it gives you the power and the stage to stand on to keep doing it over and over again. And more of what you need to do. Whether it's venture straight up, or to disrupt venture in some shape or form. So I think-

Daniel Stillman:

Actually, can we hold back to that one for one second? Because when you talked about the conversational skill of an investor, I was floored, and I'm continued to be floored. I went to ... The month before you went my friend Sim Blaustein from Bertelsmann-

Avantika Daing:

[inaudible 00:22:55].

Daniel Stillman:

So standing on stage ... We're sitting on stage, which I know you didn't want to do, and having a series of pitches, of varying quality. And then, asking really, really insightful questions to peel back the onion, and to get what's really going on, I think is a phenomenal conversational skill. I don't know how you ... I mean, that was an-hour-and-a-half of ... It's like watching a symphony. Really, the ability to consistently find the nugget, to ask the right question. I mean, I don't know if there's even a question. It's more of a-

Avantika Daing:

I had a ... Thank you.

Daniel Stillman:

Bravo.

Avantika Daing:

Thank you for that compliment, I appreciate it. I had, and I say this to kind of show my own naivety of not having grown up here, which is as I came off that stage, I had a wonderful gentleman present himself to me, to congratulate. He made the comment that I presented as an oracle. In my head I was thinking, "Is that a compliment, or what is an oracle?"

Daniel Stillman:

Yeah, it is.

Avantika Daing:

And so, I called Deborah, my partner, and I said, "Deborah, I just got called an Oracle. What does that mean?" And she's like, "It's a good thing, please don't be worried." And she mentioned the notion in this culture being called the Oracle of Omaha, and I was like, "Wow, if even one person could appreciate what we bring to the table in the jobs we do, in that manner ..." I was very touched, and very humbled. You mentioned peeling back the onion. I say that to my team. I say that to founders. I'm constantly throwing that cliche, and jargon, and maybe it's a cultural thing, and I need to come up with a better-

Daniel Stillman:

Onions are a very important-

Avantika Daing:

Visual, right? Being Indian, it's a core thing, and everything we eat and do along with turmeric. But peeling back the onion is very important. Now the reason, going back to your point about having [inaudible 00:25:05]-

Daniel Stillman:

What is important about peeling back the onion for you? What is it? Because it's not just jargon, it actually means something to you, right?

Avantika Daing:

It does. I think what it means for us is two things. One is that we can actually have conversations for four years before we come in and we invest. We don't have a thesis that we have to know you like some other institutions out there, for a period of 18 months or two years. We don't have a rule book, or rules towards that. But it so happens, if I can just deviate real quick.

In our portfolio, now 30 companies having deployed over 85 million with a portion of our fund of 25 million, we're coming in relatively soon to having putting a hundred million plus in the market towards our investment thesis. And a portfolio of 30 plus companies, majority of our investments it's just so happened pure serendipity, not orchestrated or planned, that we've known the founders, the co-founding team for a period of 18 months, I think, is the shortest. To about four years is the longest. And the reasons why we've held those relationships, a lot of it has been working very closely.

Some of it has been fairly superficial. Kind of waiting, knowing we needed to come in, but waiting for the right moment so that the portfolio construction ... To your point about, "Come speak to us when you're ready to fit our mandate over a certain stage," being Series A as a starter investor. Part of peeling back the onion is really giving us the ability and the platform in a different way. Not the way that we referred to earlier, to constantly have these conversations with founders, and technologies, and products that we'd like to support via capital.

And so, over time, part of peeling back the onion means you start with a very early conversation, but then as you go through time, or as you go through the depth of your investment analysis, your diligence process, you should go deeper and deeper. That's one part of the meaning of peeling back the onion. The other part of peeling back the onion really goes to something that our investment committee looks at, which is as the founder, the entrepreneur peels back the onion towards their technology, and what they're solving for, how does that go from base camp to summit, right?

Daniel Stillman:

I'm so glad getting to this. I definitely wanted to connect these two ideas. This is perfect. I think it's such an amazing analogy, because you need that when you're talking about a core technology. Because that's part of your thesis, right? Is that you want to find what is at the center of the onion.

Avantika Daing:

Right, and the center of the onion could be the base camp. Could be something very binary that may not excite venture capital at large, but still has a multi-billion dollar TAM. But as you go from the base camp to the summit, and you layer in all the additional value-adds as you expand either horizontally across multiple markets or areas, or you expand deeper, and deeper in a horizontal play, you're rising up the summit, right? You're rising up to the summit rather. And so, those are these extra layers that come in. Peeling back the onion I kind of use in different ways, but more in a very binary perspective.

It's often to encourage our IC, but also our entrepreneurs and founders to say, "Anchor me on something simple. Let me first understand where the monetization opportunity is, as you first go-to market, and then layer in the other monetization opportunities that expand your go-to market. Taking you to the craziest idea. Such as, for example, we've got the founder of Open Water coming in and presenting to our investors, and unfortunately you're not here on Friday at [inaudible 00:29:42] in New York at 12:00.

And she, Dr. Mary Lou Jepsen came from, the professor from MIT Lab. Former Oculus, Googler. Worked with Sergey, deep tech, disruptor. All power and mighty to Mary Lou for having done many firsts in her career. Her base camp at Open Water is pretty simple, which is to create a portable, affordable, accurate, highly sensitive diagnostics towards stroke detection. The reason why is the first four minutes of detecting stroke is extremely important. It's the number two cost in a healthcare system. She's really trying to address it from an economic perspective, but also from a humanity perspective.

But as we look at base camp to summit, this company and Mary Lou has the skillset to drive this technology into being a non-invasive brainwave therapy communication platform. Simply said, disrupting Neuralink at its own game.

Daniel Stillman:

Wow.

Avantika Daing:

I'm not drilling a hole in your brain. It's a ways to go, and there are many steps on the way. Neurodegeneration included. But understanding your first step in, versus how you scale and grow, and having a methodology to that madness is important for us as investors, and especially for growth investors as they come in to support.

And so, when we bring it home, and we put it on a platform, I think coming back to your earlier question about is this what the platform is, does it allow for a continuation of a conversation? Yes, of course it does. But the platform is actually much more than that. The platform is a grouping of products that exist today in the marketplace. It's not that it's so novel that it doesn't exist, but where the novelty comes, in is that it doesn't exist on a single platform. And what I mean by that is that we have direct investment products out there, multiple syndicates. Some Known, some unknown as syndicate leaders. That's a product that sits on the platform to provide direct investment opportunities. We have sidecar products that exist in the market. A sidecar co-investment vehicle will sit on the platform. We have funds, and funds of funds that sit in the market.

Some funds do operate on a platform where they manage lifecycle from early stage funds, to opportunity funds, to secondary funds. And so, we're going to have multiple funds that sit on the platform. And then, we have the ecosystem support about bringing in the right consulting partners, the banking partners to provide creative non-dilutive vehicles to support different stage growths of capital needs, but also supports in non-capital relationships and engagement. The platform is not just about taking the conversation forward, but also making sure there's a product that meets your needs as you grow and scale. And then, the last plug I'll give in terms of the why for a need of a platform that really sets up the economic future, is that the inherent element of a platform is that your performers rise.

So by investing early into a company that's continuing to perform and provide the track record needed, that investment opportunity specifically will continue to move from one product to another, albeit on the same platform. You are actually creating a multiplier effect on investor returns by continuing to support on a single platform your risers. Similarly, it's equally important to recognize that the non-performers get eliminated very quickly because they don't have the ability to rise within the platform.

And so, there in itself, you are providing capital protection for investors while alongside providing diverse products with different liquidity profiles. Tell me an investor is not going to be interested in a platform that's able to do all of that.

Daniel Stillman:

And that's diversification at its core. In our conversation earlier this week when I asked you what are some of your favorite ways to design a conversation, you talked about dressing the cap table, and it seems to me like this is a way you coach founders to build their own platform. I see this engine in you that is thinking soup to nuts, that tends to think end to end. Has that always been your lens? How did you learn to value that type of broad end to end thinking in your work?

Avantika Daing:

Mileage. On Friday, I was one of the speakers for NYU's PE VC annual summit, and Micah from Founder Collective was there as well. Him and I were having a little chat in the corner as he was closing out the conference as a closing keynote speaker, and one of the things we were talking about is the mileage that folks like him, and me, and my partner Deborah, and others have accrued.

That gives rise to a sense of what's perceived as judgment, but it's judgment that comes with decades of experience. For me in particular, while I didn't appreciate it when I was going through my various twists and turns in my career, switching industries, switching functions, switching roles from P&L to innovation, putting out a corporate, to an entrepreneurial journey, back to corporate, back to entrepreneurial journey, I appreciate it now. Because that diversity of an operator's experience, and that mileage of 25, 28 years allows individuals that have that construct ... And I want to take it away from it being a singular conversation on me, that are able to very quickly join the dots, and venture is known as joining the dots. And the quicker you're able to join the dots, and the further the dots go to the top right-hand corner, you want to jump in with a sense of eagerness from a capital investment opportunity. But the ability to understand where things are now, and then how do you dress around it. And in specific, I think you mentioned dressing the cap table.

Daniel Stillman:

Yeah, because I'd love a good recipe. We should definitely talk about that.

Avantika Daing:

Right, I think I focus more on the cap table because of our gender mandate investment approach. It's not an investment thesis, but it's a mandate we have. And we look at the cap table early on, even when we're looking at seed companies, to understand where does the founder sit now? What access do they have from a network perspective? What's driving their thinking, for example. And I'm just taking this as super high level. If a founder is bringing their friends, and family, and they've got a network of really well known family offices that can carry them through later stage of capital needs, that's wonderful. But that doesn't allow them to diversify, to truly become attractive to venture investors, especially at later stage.

You want to think through dressing the cap table at the right time. Now, not all of it's going to happen at seed or Series A and Series B. There's a right time and a right place to do this, but it's a conversation we have with our founders early on, and we like to give them the sort of direction, and at least instill some amount of conversation to your point, about putting the bugs out there, in their head. Which is think through who is your deep pocketed investor that's going to take you through early stage to mid-stage?

Who is the growth stage deep pocketed investor that you'd like to see come in? Who is your strategic investor that is your customer, and will also be interested in taking an equity stake on your cap table? Who is your venture, early seed investor that has the right reputation to potentially bring in their network and attract some of these other caliber of investors or categories of investors that I've mentioned? And then one in particular, which is my favorite is investors that haven't had an IPO experience, often think that finding the investors that take them to IPO is their last capital need, and that's not true. Companies that go public or post IPO still have need to raise capital.

And so, you need to think through based on where you are for Series A and a Series B company, who is that type of investor. And often enough it's not VC. It can be, but it's often enough not. Who is that investor that's going to take you to IPO, but will also support you post IPO for your capital raising needs post [inaudible 00:40:41]. And those [inaudible 00:40:43]. We have great relationships. So part of it is making sure that the dressing of the cap table, the thought process starts early. We come into Series A. Part of the reason we come into Series A is because dressing the cap table is extremely important. Sometimes we look at the cap table, and even if it's a technical Series A company, we'll say, "Sorry, your lead investor coming in is a family office that's highly motivated by impact, and we love that, but it is not the right lead to be taking you from Series A and B, and beyond.

We will actually request a reconstruction of the cap table into a co-lead coming in, that will have the right construction in place to take them. And a lot of setting up the cap table at Series A prevents kind of preventative maintenance management, if you will. A lot of problems that act as bottlenecks when you reach a Series B or beyond growth stage. And some of that is you need a different mindset of [inaudible 00:41:53].

If you are a water analytical company, which we have, and one of my favorite founders out there, the company's called Ketos, K-E-T-O-S. Amazing investors that have been supportive, but the cap table needs to be constructed, now moving forward in a different way to really bring in the investors that have the ability to think through growth capital and monetization for a company that gave roots in impact. [inaudible 00:42:29] talking about water, and water quality, and quantity, right. So as a company grows, and as the personality of the companies change, and as the technology rises up the value chain into enterprise monetization, how do you evolve the cap table and the investor mindset behind it?

Daniel Stillman:

I feel like I need to quote my mother in every podcast, because she listens to most of them, so I get to say, "Hi mom." She always says, "Start as you mean to-"

Avantika Daing:

[inaudible 00:42:58].

Daniel Stillman:

Hi mom, "Start as you mean to continue," and this is a really fundamental mindset. The idea that, Oh, I will get that investor to take me to IPO and beyond when I am at a later stage versus thinking about the end at the beginning, and setting yourself up for success seems like a really valuable subject to coach your companies on. I could see why that's one of your favorite ... It's a recipe to say like, "Are we dressing this cap table well?"

Avantika Daing:

[inaudible 00:43:34].

Daniel Stillman:

And just stepping back and saying, "Is it designed with that in mind?"

Avantika Daing:

Can I interject with-

Daniel Stillman:

Yeah, please.

Avantika Daing:

... one [inaudible 00:43:40] real fun example that actually-

Daniel Stillman:

Please, of course.

Avantika Daing:

... [inaudible 00:43:43] unintended on your point about a recipe. My comment earlier about knowing and working with a founder for four years is a company, the parent original company's called Kiverdi, K-I-V-E-R-D-I, I think. The company we invested in is Air Protein, Dr. Lisa Dyson, look her up, fascinating. Grabs carbon from the air, so helps with a lot of carbon climate tech, ESG oriented problems. Not problems, solutions. But takes that carbon capture, reproduces it into protein. Chicken protein, fresh protein, and others to make it edible. Taste, smell, look, feel starting with chicken.

Daniel Stillman:

That is dressed, that's crazy.

Avantika Daing:

Now the story, and I'll give you the nutshell, because I think it's interesting, so I'm stealing a little bit of interrupting your airtime here, so apologies there.

Daniel Stillman:

No it's your airtime.

Avantika Daing:

Deborah Jackson, my partner got introduced to Lisa. Lisa leaned on Deborah in the early years to help guide her. She was looking for venture capital. When I got involved, we looked at Kiverdi. Deborah continuously worked with Lisa for the years leading into her becoming what we call Venturable, which is also a version of dressing the cap table to getting there. And Kiverdi continues to exist as a separate company in a licensing structure. We knew while it had many shots to go, and it had a lovely licensing application across industries, gas and oil, fishery, like important industries that needed disruption while creating a further longevity towards limited renewable resources, so, huge. But we knew venture would not touch it, because of its go-to-market monetization towards licensing, but also towards the setup of the industry.

And so, over the years of chipping away with what would be the right strategy, Lisa, Dr. Dyson, finally landed on creating a separate company called Air Protein with a very specific go-to market. Two words, focusing on edible, consumable protein to the end consumer. We could create a monetization as they have done with enterprise partners. They've got EDM, which is the largest ingredient provider and distributor, as a strategic investor both on the equity side but also on the customer side.

They've got enterprises on the cap table, so they're able to expand into a B2B monetization, and they've got the right engagement with retailers. Think large FMCG type distributors to end customers, but also retailers as in shopping retailers-

Daniel Stillman:

That's fascinating.

Avantika Daing:

... that are lined up and ready to come in at the right time. I mentioned that because I wanted to be tongue-in-cheek on your pun about the right recipe, because here she really had to think through putting the right recipe, pun intended, but also she had to think through the right construct of the creation of a new company, and then dressing her investor cap table, which is very different in look and feel to cover her original company.

Daniel Stillman:

It's interesting. Going back to the base camp and summit metaphor, is this a summiting opportunity for her? She has the base camp technology, and she is thinking what is a real path to growth and success given the technology. Is that a fair reuse of that analogy?

Avantika Daing:

Yes. I think her base camp for Air Protein is chicken, to be specific. There's a horizontal and a vertical play as she rises and climbs the summit. The closest in sort of going deeper into our vertical play, is expanding from chicken, to fish, to meat. And there's a reason why she chose to do meat later, or last. The market already has some options out there, but for other reasons as well. I would encourage you and the listeners to take a look at some of her TED talks, but also she speaks at different VC summits, and she explains that.

I don't want to take that away from her. The other part of her rising from base camp to summit is expanding her customer stakeholder. So from being an ingredient player, to being a distributor, end product, to enterprise such as retailers like Whole Foods and others, Krogers. Also, to FMCGs distributors, but also ... Think Burger King or health foods like [inaudible 00:49:10], that meet the customer with the end product.

And then, finally, being a brand direct to the end consumer. And these could be all scale opportunities for her. And then, frankly, if you want to expand it even further as you look at all the different magic that can happen at summit, is taking a technology just Kiverdi did, and expanding it beyond food. Into beverages, into lifestyle. And then, if one needed to take it all the way into oil and gas, you could, but you've already got a company that's doing that at a licensing basis.

Daniel Stillman:

Yeah, it's so interesting to think about all of the different ways in which you can take that core idea, the core technology and the founder's desire to make something from it. And you and Deborah just sort of chipped away that old Michelangelo and David metaphor just to find that core value proposition that was investible and attractive to bring multiple stakeholders together. I mean, that's crafting the core. You peeled the onion all the way back, and you found a core value proposition that could really start a whole new conversation, which is tremendous.

We're sadly running towards the end of our time. One question we haven't asked that I want to ask is around the different types of coaching and mentorship that founders need to be hearing as they grow their companies. When we think about this platform, when they're getting past their cap table being dressed, when they're starting to go towards growing their company, what non-monetary advice, coaching, mentorship do these founders need to hear most at those critical junctures as they grow in your experience?

Avantika Daing:

That's a loaded question.

Daniel Stillman:

Fair.

Avantika Daing:

I say that because I think female founders, diverse founding teams have a different set of considerations to be transparent. That they may not have a natural place to bring up, to ask without having a sense of a label being put on them, or a taboo being put on them. There's a very open and, well, I don't know how open it is, but there seems to be a conversation happening on founders' mental health at large. It doesn't matter what type of founder you are. White male or otherwise. I just don't know how authentic it is, but I'm glad it's happening. What we deal with is addressing a lot of that at an authentic level, but I'm not sure that, that's what I want to end this conversation on. I would probably say the two things are learn to say no to your customers, as well as investors, to be hardball on your strategy.

And there are two different types of strategy when you're ... One is focused on revenue. If you are a multi-year SaaS contract with a hardware component build in, and you've got customers saying, "Well, I'm not sure I want to pay for three years. I want to do a pilot for six months, and I don't want to pay you, and then I'll scale up, and then I'll do a contract for one year." You got to walk away from that. There are ways in which you can accommodate that, but you cannot be creating exceptions, especially early on. It's a flip of mindset, and it's nerve wrecking to think ... Most people think early on, "Oh yes, I've got a great enterprise. Logo, top 500 public company coming, why would I want to keel over?" Well, you need to set precedents, and you need to set the right precedents. You have to be a bit strategic.

I'm not saying you shouldn't accommodate for those asks, but be strategic in how you create that construct. So, for a pilot, you build a pilot in. If they like the word, "Pilot," you give them pilot, but you make it monetizable. If they want to backhand, you have to understand, again, peeling the onion back, understanding where their motivation is. And the motivation there is, large enterprises like to say, "We want to first test you, and then backend payment." How do you build that into a construct of establishing your contract, and the nuances that go into the contract that set you up for monetization.

There's a component of learning to say, "No," with a creative element of accommodation. And then the second part of, "No," is to your investors. Early investors ask for side letters. They ask for preferences. You want to set yourself up for success for later rounds, and you want to be conscious of what construct and precedents you're setting with your investors now. And having conviction and motivation on yourself in not reducing your valuation, or not wanting to give up too much ownership, whatever it might be for you as a founder or founding team, sticking with your narrative is extremely important.

It's important because it's not a one-time engagement that an investor or VC has with a founder. To your own point, Daniel, about a conversation. This is a conversation that's going to go on for months and years. Good VCs like to engage with their entrepreneurs for a period of 18 months and beyond. Smart founders like to begin that engagement earlier. And so, we want to make sure that you're not flipping from right to left and accommodating just because you're desperate on a capital need. And then, the last thing I'll say is very important. It's not done enough, and it's completely underestimated, which is think two steps ahead. Also, a different version of peeling back the onion. But if you're raising seed, think about Series As and Bs. If you're raising As, think about Bs and Cs, and why? Look at the market today.

Some of our portfolios that we've worked very closely with when they were raising the Series A, we very quickly came in and we said, "Now is the time to bring in non-dilutive capital. Meet, they're friends of ours, X, Y, and Z that are interested in funding you. Giving you a line of credit, giving you a debt vehicle if you're a Series B," bring that in. Unfortunately, you're not thinking that, because you don't have a need for it. [inaudible 00:56:58] Founders would say, "Well, I have a runway of 18 to 24 months, why do I need to think about that? I've got to runway for 36 months. Why do I have to think about it?"

"Yeah, great. I'll take the introduction, but I'm really not going to lean in. I'm too busy now trying to close my [inaudible 00:57:14] later." Well, later becomes too late, because you cannot time a situational market. And a situational market for us is a COVID. A situational market for us is consideration towards a down market. And so, to manage situational markets, when you are doing your equity round at the back of it is the time to come in and put creative financing vehicles in place. You may never need it. You may end up paying a bit, which could be the downside. But frankly, you're never going to lose out on using, and having that as a backup in creating financial health. And really, frankly, drawing that back to your own mental health in using it as a tapping mechanism.

Daniel Stillman:

That is tremendously powerful advice, a month ago. So with our literally one minute left, is there one question I have not asked you that I should have asked you?

Avantika Daing:

It'll be a question, but we won't have time to answer it, which is-

Daniel Stillman:

Well, for the next conversation.

Avantika Daing:

... are motivations aligned in the VC industry?

Daniel Stillman:

Well, it sounds like the question is posing that it's maybe not.

Avantika Daing:

You're right, it's not. And that's why there is a inherent need for a platform product presentation to be existing in VC to bring those motivations together.

Daniel Stillman:

Well, I mean-

Avantika Daing:

VC industry, if you don't mind.

Daniel Stillman:

No, no, no.

Avantika Daing:

VC is an [inaudible 00:59:14], your point about the leaky bucket. We create the leaky bucket syndrome. We're in the business of creating the leaky bucket phenomenon. And what I mean by that is as VCs we come in for two touchpoints. Some of us come in for maybe more because we've got the capital power through a dry powder, and we really like how the growth of a company's happening, and we found the needle in the haystack.

But by construct of how venture invests, and because we're thematic, and because we're stage driven, or driven through various constructs of our investment pieces, we only come in to touch an investment between one to two points, sometimes three and beyond. And by default of that, we are creating a leaky bucket. Where we're letting loose, and letting go of our investments that we've made, and we're unable to support it because of lack of capital power, or because of lack of the right platform that will allow for the growth engagement to happen.

Daniel Stillman:

And that's intentional investing at the core. Changing the conversation. This is tremendous. Thank you so much. I want to make sure you have plenty of time to get to lunch. I'm really grateful we made time for this conversation today. Is there any place that people should go on the internet to learn more about all things Avantika, and all things Plum Alley, besides the power of Google? Any place you'd like to send people?

Avantika Daing:

Thank you for asking. I have a horrible social profile. So I am unfortunately not on Instagram. I am on Twitter. My Twitter handle is @AvantikaVC. I'll spell that. It's A-V-A-N-T-I-K-A-V-C. I am on LinkedIn, and I'm fairly active, so if somebody sends me a message or inboxes me, I will respond in some shape or form. And then, our website is plumalley.co. So not com, but co. Plumalley.co. We are putting a new website up, so that should be up in the next two months. And we hope that the conversation that we've had here today would be reflected in that manifestation of plumalley.co.

Daniel Stillman:

That is so exciting. Thank you so much for this time. This has been a beautiful conversation. I appreciate your generosity, and I look forward to the next conversation.

Avantika Daing:

Yes, and safe travels to you. Thank you for allowing for a very natural, authentic conversation to happen, and look forward to engaging further.

Daniel Stillman:

Awesome. End scene.

A Recipe for Team Agility: One Page, One Hour

Today my conversation partner is Matt LeMay! Matt is an internationally recognized product leader, author, and consultant. He is the author of Agile for Everybody (O’Reilly Media, 2018) and Product Management in Practice (Second Edition O'Reilly Media, 2022), and has helped build and scale product management practices at companies ranging from early-stage startups to Fortune 500 enterprises. 

Matt and I met at UX Lisbon last year where he gave a talk that included him describing his extremely actionable recipe for team agility: the One Page / One Hour Pledge, a powerful commitment to minimize busywork and maximize collaboration that has been adopted by individuals and teams at Amazon, Walmart, CNN, and more. 

I was excited to bring Matt into a conversation about this pledge, because I know how easy it is to get caught in a rabbit-hole of perfectionism before sharing my work with others. Teams can work more fluidly if we reduce the cycle time between solo work and team work.

Matt is an advocate for the power of focus, subtraction and feedback loops over perfection - I mean, would you rather ride a bike you can only aim once or one that you get to steer continuously?

I never dreamed I’d get to have a podcast conversation that includes references to Alan Watts and the power of Ego Death to accelerate your team’s success and ultimately, one’s own success…but glad that we are! 

Matt and I unpack how TIMEBOXING (ie, Tight-and-almost-thoughtless constraints ) helps shift the relationship between thought and action in teams and organizations…and can help move the conversation forward.

Links, Quotes, Notes, and Resources

Matt's website

Product Management in Practice

https://www.onepageonehour.com/

Matt’s talk at UX Brighton on “You Don’t Get anyone to do Anything”

“When we attempt to exercise power or control over someone else, we cannot avoid giving that person the very same power or control over us” Alan Watts

Alan Watts “The wisdom of Insecurity

Summary

6:22 Matt and Daniel discuss the power of constraints, focus, and subtraction in product development

18:06 Coaching teams to use the one page, 1 hour pledge and how it shifted his perspective on what is considered impressive documentation

35:21 The role of product leaders in applying constraints, bringing focus, encouraging subtraction, and managing complexity

37:45 Matt emphasizes the importance of celebrating subtraction and user-centricity in product development

40:26 The value of continuous discovery and learning from customers regularly

44:11 Matt suggests finding a half hour every week for research with executives and focusing on tactics rather than philosophy

51:45 Matt LeMay shares a story about understanding why a decision was made, even if it's not the answer you hoped for, and the importance of asking questions to get a better understanding of the decision-making criteria
57:36 Matt emphasizes the importance of ego death in good product work and cross-functional collaboration, and the need to focus on team success rather than personal rewards or recognition

Key Quotes

Minute 10

Matt LeMay:

I used to work with a company that did these really long retrospectives after workshops. They were brutal. These were three hours. Everybody would say what they felt they had done well and what they could have done better. Everybody would go around and tell them what they had done wrong or what they could have done better. Sometimes the retrospectives would last longer than the workshops themselves. And I love retrospectives, but this was just excruciating.

Daniel Stillman:

That sounds like a ratio is off there.

Matt LeMay:

Yes. So I said, "How about we timebox this to an hour?" [inaudible 00:10:15] said, "Yeah, sure, whatever." So everyone starts going around and talking. I'm sitting there quietly. I don't say anything. And everybody talks, an hour goes off. And I say, "All right, it's been great." And they say, "Wait, no, well, we haven't finished yet." I say, "Well, clock says we're finished. We time blocked this for an hour." Everybody got really uncomfortable. But in order to change the way you think, I think you need something to force you into a state of reflection. You need something which will shake up that system between thought and action in a way that compels you to look at it and say, okay, what is the relationship between thought and action? What is driving this behavior? What is the reward I'm getting? What is compelling me to spend this time talking in this way? What is the value I'm getting out of this? Which is part of why I am such a big believer in really tight and almost thoughtless constraints.

Minute 24

Matt LeMay:

So many of these things all come back to user centricity, customer centricity. I saw Matt Cutts who had been at Google for a long time, and was working for the US government, talk a couple years ago. And somebody asked him, "How do you break through the bureaucracy of an organization as complex as the US government?" And he said, "Oh, that's a really easy one. Bring decision-makers closer to customers." No hesitation about that. And I feel like when I've seen product leaders and product managers effectively navigate that complexity, part of how you do so is by demonstrating that... I talk about this a little bit in Agile for Everybody, but there are dependencies which are felt by the customer and dependencies that are not felt by the customer. And if a dependency is felt by the customer, it should probably be felt by the organization as well.

In other words, if you have siloed folks into a bunch of teams, but a user's journey is jumping around through the thing built by those teams, then those teams should feel some pain too. If they don't, they're never actually going to make things better. Because they're going to sit within their silo and they're going to say, "Look, I'm working on my future. I'm making this area better. That's my job. There's no reason for me to talk to these other people and deal with getting outside of my comfort zone, deal with situations where what's important to me might not be important to somebody else. Deal with situations where the thing I've been working so hard on might come under a different scrutiny, or might be revealed as actually not being that valuable to the sum total user experience."

But when you see a user struggling, when you feel that sense of, oh, the complexity I'm adding is bad complexity, the dependencies we've created are harmful dependencies that are felt by the user. It's a very different thing.

Minute 35

Matt LeMay:

So if you're trying to get a room full of people to make a decision, see how each person in the room is going to make the decision, and then figure out what they're basing that information on. Then you'll probably figure out what information you need to consolidate or answer or resolve in order for the room to make a decision. But I rarely ever now spend much time thinking or talking in the abstract before asking participants in a room, how would you make this decision right now? If you have these three options, which one would you choose and why? Because that will help me understand what decision-making criteria are necessary, and it'll help me understand if I'm thinking about options the right way.

More About Matt

Matt LeMay is an internationally recognized product leader, author, and consultant. He is the  author of Agile for Everybody (O’Reilly Media, 2018) and Product Management in Practice (Second Edition O'Reilly Media, 2022), and has helped build and scale product management practices at companies ranging from early-stage startups to Fortune 500 enterprises. Matt is the creator of the One Page / One Hour Pledge, a commitment to minimize busywork and maximize collaboration that has been adopted by over 100 individuals and teams at Amazon, Walmart, CNN, BBVA, and more.

Matt is co-founder and partner at Sudden Compass, a consultancy that has helped organizations like Spotify, Google, Clorox, and Procter & Gamble put customer centricity into practice. In his work as a technology communicator, Matt has developed and led digital transformation and data strategy workshops for companies like Audible, GE, American Express, Pfizer, McCann, and Johnson & Johnson.

Previously, Matt worked as Senior Product Manager at music startup Songza (acquired by Google), and Head of Consumer Product at Bitly. Matt is also amusician,recording engineer, and the author of a book about singer-songwriter Elliott Smith. He lives in London, England.

Full Transcript

Daniel Stillman:

Okay, Matt, thank you for making me time for being...

Matt LeMay:

Thank you for having me.

Daniel Stillman:

I want to start at the beginning of me knowing you. Just, actually, I think sitting down to dinner in someplace in Lisbon.

Matt LeMay:

I believe it was.

Daniel Stillman:

I really enjoyed your talk at UX Lisbon, and partly because it is about constraints, and partly because your talk is funny. And also because while I think I seem to recall... I was looking for my notes, I couldn't find my original sketch notes from your talk. Because I was feverishly sketching during your talk. Was that like, oh, my slides aren't fancy, but your talk is funny. You are a very entertaining speaker. You entertain while you educate, and I really appreciate that.

Matt LeMay:

Thank you. I do not have the skillset to make my slides fancy. So funny is about the best I can do.

Daniel Stillman:

I want to start with the one page, one hour pledge, because I think it is a blockbuster talking about constraints and the art of focus. It is so easy to let a communication or document just bloat.

Matt LeMay:

Yes.

Daniel Stillman:

I wonder when the seed first took root in you.

Matt LeMay:

Yeah. I have always been a verbose person, and I have been the nightmare friend or colleague or romantic partner who will send you the 20-page email with all of my thoughts meticulously composed. And then say, "Well, I've done my part." But there's no way anyone could misconstrue my position, I've made it abundantly clear. And then gotten bitter and resentful when it turns out not everybody wants to read my 20-page treatise on whatever it happens to be. I am as guilty of over long, overstuffed documentation as anyone, if not more so. And I found myself working as a consultant with an organization. And frankly, just that my approach wasn't working. I was both creating a lot of big heavy documents and facilitating the creation of many big heavy documents. People weren't reading them, people were busy. I had a unshakeable sense that I was wasting people's time in order to gratify my own sense of a job well done or having done something well.

I remember the conversation very clearly. I was working with a product manager who said... Another product manager just came to me and said that they want to see what my team is working on right now. "I don't have anything." "Can you help me put together a deck?" And I said, "Well look, why don't you try just spending one page and one hour on it, and we'll see how that works out." This product manager said, "Wow, it's kind of catchy. One page, one hour." One page, one hour. A week later I said, "Well, how did that go?" This product manager said, "It was really interesting, I gave product manager who asked for it this really rough one pager and I said, 'Look, don't think less of me for this. This is a really rough document. It's just a brain dump of what my team's doing.' And they wound up coming back to me and saying, 'Gosh, that one pager was so useful. It was just exactly what I needed and nothing else. So I'm going to try making one that captures what my team's working on.'"

Daniel Stillman:

Yes.

Matt LeMay:

I said, "Oh, there seems to be something here." So I started coaching more teams I've worked with, try this one page, one hour thing. And then I was in a conversation with my business partners in the States. I live in London now, which is why I qualify that we're in the States. And I told them about this work I was doing, one page, one hour, and they both smirked at me. I said, "What's so funny about this?" They said, "We love you, but when you work with us, you give us the most comprehensive documentation." I said, "Well, yeah, but you two are geniuses and I want to impress you and I want you to think I'm smart."

And they said, "Yeah, why do you think everyone else isn't doing one pagers? They feel the same way." Oh. So it started to shift. I had seen the utility of this in terms of applying a constraint to documentation, but I hadn't seen the utility of it until that moment, and shifting incentives. I told my business partner, "Okay, look, I'm going to write up a little pledge. I'm going to pledge to you that I will spend no more than one page in one hour on anything before I share it with you. And if I break this pledge, I want you to hold me accountable. I want you to say, Matt, you may be turning in something which is very intrinsically impressive, but in the context of our working agreement, you have actually done something bad. You have actually not excelled at this. You have broken a commitment you made."

And it was really interesting having that in place because I did break that commitment several times. Either because I thought, oh, we have enough shared context, I'll just finish the document. Or because I was having a rough day and wanted that dopamine hit of having turned in something impressive. But in all those cases it didn't work. Either we realized that there were enough assumptions baked into my document that it would require rework, or my business partner said, "This is a lot, and we feel excluded by the fact that you sought to finish this thing without our input."

Daniel Stillman:

It's so interesting.

Matt LeMay:

To me, the most interesting part of the one page, one hour pledge is not so much the constraint itself, but the idea that you can explicitly shift the goalposts for what is considered a successful or impressive document. Because I'm pretty convinced at this point that if you don't shift them explicitly, they won't shift.

Daniel Stillman:

Right. And so it doesn't really matter if it's one page or two page, or if it's three slides or-

Matt LeMay:

Exactly.

Daniel Stillman:

It's really about having the conversation. And I guess I'm wondering... These are the things I'm wondering. I'm going to share one. There are several things I'm wondering and I'd like you to respond to any and all of those things.

Matt LeMay:

Absolutely.

Daniel Stillman:

One, I know you wrote a book called Agile for Everybody. And I was also reading about your perspective that there is no product mindset, there are product action sets. And so the idea that doing things differently is more important than thinking differently is a really interesting one. There's a third point, I apologize for my bloviation.

Matt LeMay:

No, it's all good.

Daniel Stillman:

There's a balance always between... There's a concept called triple loop learning, where doing the right things can get us the right actions, thinking things differently can help us notice when we're not getting the right things done to get what we want. It's impossible to shift what we're doing unless we shift how we're thinking. And it's very hard to shift our thinking unless there's a shift at the level of being. Our goal, our aspirations. And so I feel like on one hand the actions are clearly the most juicy. Like oh, we can start doing things differently, but it requires a shift of I do not need to feel impressive. I will not feel ashamed of incomplete work. I will show incomplete work. I feel like we have to work at both ends in order to have a transformation.

Matt LeMay:

Absolutely. For me, a lot of this comes from my experiences in cognitive behavioral therapy, which was really helpful for me. I remember the first time I went to see a cognitive behavioral therapist in New York, I had been in a lot of talk therapy previously. And I showed up ready to, it all started with my family. And my therapist said, "Look, that's great, but what are you doing? You have anxiety issues." And I said, "Well, I'm drinking coffee all day, and I'm never exercising. And I sit around and scroll." And she said, "Okay, well, work on those things. If you can't start modifying some behavior, I don't think we're going to have a starting point where changing your thinking is going to stick. We need to basically just create an inroad before we can start reflecting and becoming more aware of the way that you think."

And I hated this. I was so mad. I was like, oh, this is my special feelings time. How dare you ask me to change my behavior and do things differently in my life? But I found that in some cases, I think behavior and what you do is the most accessible lever. And I think that sometimes when you change what people do, especially when you apply constraints, it forces some openness. It forces people out of their comfort zone. I remember the first time... I used to work with a company that did these really long retrospectives after workshops. They were brutal. These were three hours. Everybody would say what they felt they had done well and what they could have done better. Everybody would go around and tell them what they had done wrong or what they could have done better. Sometimes the retrospectives would last longer than the workshops themselves. And I love retrospectives, but this was just excruciating.

Daniel Stillman:

That sounds like a ratio is off there.

Matt LeMay:

Yes. So I said, "How about we timebox this to an hour?" [inaudible 00:10:15] said, "Yeah, sure, whatever." So everyone starts going around and talking. I'm sitting there quietly. I don't say anything. And everybody talks, an hour goes off. And I say, "All right, it's been great." And they say, "Wait, no, well, we haven't finished yet." I say, "Well, clock says we're finished. We time blocked this for an hour." Everybody got really uncomfortable. But in order to change the way you think, I think you need something to force you into a state of reflection. You need something which will shake up that system between thought and action in a way that compels you to look at it and say, okay, what is the relationship between thought and action? What is driving this behavior? What is the reward I'm getting? What is compelling me to spend this time talking in this way? What is the value I'm getting out of this? Which is part of why I am such a big believer in really tight and almost thoughtless constraints. I love [inaudible 00:11:14]-

Daniel Stillman:

Like the one page, one hour is a thoughtless constraint.

Matt LeMay:

When you talk about 5, 10, 20 sketch storming, the idea of having five minutes to draw a diagram of something on a sheet of paper. I love that. And I've used that approach in some of the roadmap mapping exercises that I do, what I call generative road mapping. Which is, rather than trying to figure out what's the right framework for roadmapping? Just sketch what you think captures visually the story you're trying to tell about the thing you're building. I worked with an organization a while ago where we did 10 minutes of prototyping a strategy document. What would a one pager of our strategy look like? Everybody took 10 minutes, then we synthesized it. And a five hour session of talking and walking through decks and asking a lot of really important sounding, but ultimately not that immediately relevant questions wound up getting wrapped up pretty definitively when we looked at these prototypes and said, "Oh, everyone's actually thinking about the same thing, more or less."

There's a clear enough through line through this that we can subtract, we can converge, we can make this happen. I think that the last example I'll share, I've worked with a lot of teams that are really interested in this notion of psychological safety. Who say, "We don't have psychological safety, we don't have trust. This is a low trust team. What should our decision rights be?" And the first question I usually ask them now is, "When somebody on your team emails you, how quickly do they expect a response?" And they often say, "I don't know, an hour a day. Not at all." In so many cases, these things that feel like big emotional issues for a team, like a lack of trust or a lack of psychological safety, come down to very simple, straightforward, tactical misalignments.

The first step I take with any team I work with now is to create a comms manual that just says, how quickly do you expect a response over these channels? What are working hours? How do you communicate urgency? How do you involve stakeholders from outside the team? These things that might seem fairly quotidian and not big product mindset, thought experiment-y. But it's been really interesting to me how often these bigger issues are ascribed things which are really just a matter of, we have not taken the time to explicitly discuss how we communicate with each other. And some of those really simple behavioral levers have had more of an immediate and meaningful effect on how teams communicate with each other than multi here transformation initiatives, et cetera.

Daniel Stillman:

I would call that conversation design. Literally designing an email is the beginning of a conversation.

Matt LeMay:

Yeah. [inaudible 00:14:21].

Daniel Stillman:

It's weird. When we're talking in person, 200 milliseconds is about what I would expect any person to respond to me before I start to feel like there's too much silence. Or they're overthinking things. And that's just in the cultural air. For whatever reason, if you wait too long when we're talking in person, it feels like dead air. And we presumably both feel some anxiety, right? I start to be like, wow, did my question not land? Does Matt hate me? He's thinking really hard about this. And so it is not surprising that an email conversation, when I'm not getting an immediate response, would create an equal amount of anxiety, A, in the sender. And B, we all know that feeling of an email sitting in our inbox [inaudible 00:15:16] glaring at us. The analogy I always use, and nobody ever gets it, but I still use it anyway, is from Pee-wee's Great Adventure. I don't know if you-

Matt LeMay:

Oh, yes.

Daniel Stillman:

There's a scene where Pee-wee is rescuing all these animals from this pet shop that's on fire. And every time he goes into the pet shop... Well, the first thing he does is he rescues the monkeys, and the monkeys help him rescue all the other animals. Leverage. This is genius. But he looks at the snakes every time and he's like, "Ugh, snakes. Not going to rescue the snakes." And finally he rescues the snakes last. And it's like, ah, the snakes, he's got handfuls of snakes. I feel like we all have those feelings about, ugh, this email. If I could just say to somebody, I haven't responded to this email because I feel anxiety about this email, or I don't know how to respond, or I feel like I have to have a perfect response. I wish there was a comms manual for that of, hey, this email is, it's been in my inbox for a month and I don't know what to do about it. Can we have a two-minute conversation?

Matt LeMay:

Well, my business partners and I had a email subject style guide that we use for internal communications, where every email had to say, in brackets in the email subject, response required by date/time, response requested by date/time or FYI. And that was really good. Because you could look at that and if it said FYI, then you could just let it sit there. And if it said response required by date/time, you'd prioritize it. And if it said response requested by date/time, then it falls to a second tier priority because you knew you weren't in a block around something. Again, I think some of these fairly routinized, structured approaches to team communication, especially asynchronous communication. Which, as you said, if you're in a person face-to-face conversation with somebody and they start to get anxious, you see them start to get anxious and you kind of, oh, [inaudible 00:17:06] this natural dance we do. Whereas if people are sitting at their desks just stressing out about an email, they never see that and they often wind up making assumptions about the other person.

Daniel Stillman:

Yes. Well, [inaudible 00:17:19] there's a whole narrative we tell.

Matt LeMay:

Exactly. I think having those agreements in place explicitly is so important.

Daniel Stillman:

This also speaks to the point that a conversation, where the conversation happens affects the conversation. Email is not designed for this.

Matt LeMay:

No.

Daniel Stillman:

Slack is not designed for this. I wouldn't want everyone to just have all of their conversations in a sauna, but that's kind of what you're saying here. It's like, this can be embedded in every communication if we're putting it in a place that has that information as part of the communication.

Matt LeMay:

Yeah. It was really interesting, when we wrote the comms manual, my business partners and I for the first time, we started with cadence and then we went into a channel. So it was like, for I want a response ASAP, let's use WhatsApp. For, I want a response by end of workday, let's use Slack. And for, hey, 24 to 48 hours, or 72 hours max, use email. And within two weeks we had stopped using Slack. Not because Slack is a bad tool by any means, I love Slack. But because there were just very few communications that fit that cadence. It was very much either like, oh, I need an answer to this right now, or take your time. It was interesting to see what happens when you actually think through the purpose of a communication channel before you retrofit the channel itself. Because I've certainly worked with a lot of teams that go from email to Slack or from email to Teams and recreate all the same communication problems, except now they have two or three or five different channels to recreate those problems, and everything just gets exponentially worse very quickly.

Daniel Stillman:

That gives me hives. I feel like I want to talk about the evolution of product at a company. Because I feel like every company is a product company, depending on how you like to look at things. My friends who are service designers may say, but everything, every product is really a service. And that may be true, but I would say a service is a product because you buy it. And almost every product or every service is digitally mediated. At some point everybody is going to say to themselves, God, we need to get better at product. And I'm wondering, in the evolution of a company... It's like, when does a bill become a law? Or how does a caterpillar become a butterfly? I imagine in your mind there are some set points where from zero to one, from not having a product to the minimum viable or the minimum lovable, or the whatever the fastest time to value product, they don't need necessarily a fractional product leader or a head of product because everyone's the head of product, or the CEO's the head of product.

At some point it sounds like there's a moment of reorganization, focus, subtraction, and constraints forming that is hard to do on your own. Because whatever reason, because behaviors or patterns have become entrained, and there is some value in bringing someone else in. And maybe that's on a temporary basis or on an ongoing basis. And then there's another set point where they're like, we need a chief product officer or a head of product.

Matt LeMay:

Yeah.

Daniel Stillman:

What do you find that people are doing? What do you wish people knew about how to manage those transitions?

Matt LeMay:

What I wish people understood is that you bring in those roles to, as you said, apply constraints, bring focus, encourage subtraction, and manage complexity. I think the challenge I see when I've interviewed for those roles, in a lot of cases they've been seen as very additive roles. We need you to hire more people, we need you to add more people. We need to expand. And honestly, nine times out of 10, that is not the biggest problem that a growing company is facing. We can't scale and grow and hire fast enough is a real problem for some organizations. But I think as you see these wild accordion shaped expansions and contractions of companies over the last year, it's not the biggest problem.

The biggest problem is, are we focused on the right thing? Are we actually connecting all of these pieces in a way that creates a compelling experience? Are we actually focusing on the right customers right now? Are we managing our bets in such a way that if we invest in something and it fails, we can acknowledge that it is a failure, learn from it, and move on? In a lot of cases, what a product leader is empowered to do is to look at that, look across the organization, and make those calls and facilitate those decisions. And establish the criteria for making those decisions in a way that individual product managers wouldn't be able to or comfortable doing.

That is such critically important work, but it's not the work that people usually ask me about when I'm applying for an interview for these roles. Which I think is really too bad, because I've worked with a lot of companies in my day. And the challenges, the great product leaders-

Daniel Stillman:

Your day isn't over, Matt. I don't know if you're allowed to use... I'm still a young [inaudible 00:23:15] man, everyone.

Matt LeMay:

But the best product leaders I've worked with are the ones who can get a complex team to make subtractive steps. Like Natalia William, who I worked with at Mailchimp, who was their chief product officer [inaudible 00:23:30] Hootsuite, really was able to get in there and say, "What if we take a step out of this thing? What if we streamline these things? What if a way to increase conversions is not to add features, but to remove steps?" That's how I think great product leaders think. And you can tell immediately how challenging that is, because somebody built those steps. Somebody's job is to maintain those features that are going to be deprecated, and those people are going to feel a certain way about it. And of course they are. Most companies celebrate the launch of new features. They celebrate, look, we did a thing, we built a thing, we shipped a thing. And celebrating subtraction and celebrating...

So many of these things all come back to user centricity, customer centricity. I saw Matt Cutts who had been at Google for a long time, and was working for the US government, talk a couple years ago. And somebody asked him, "How do you break through the bureaucracy of an organization as complex as the US government?" And he said, "Oh, that's a really easy one. Bring decision-makers closer to customers." No hesitation about that. And I feel like when I've seen product leaders and product managers effectively navigate that complexity, part of how you do so is by demonstrating that... I talk about this a little bit in Agile for Everybody, but there are dependencies which are felt by the customer and dependencies that are not felt by the customer. And if a dependency is felt by the customer, it should probably be felt by the organization as well.

In other words, if you have siloed folks into a bunch of teams, but a user's journey is jumping around through the thing built by those teams, then those teams should feel some pain too. If they don't, they're never actually going to make things better. Because they're going to sit within their silo and they're going to say, "Look, I'm working on my future. I'm making this area better. That's my job. There's no reason for me to talk to these other people and deal with getting outside of my comfort zone, deal with situations where what's important to me might not be important to somebody else. Deal with situations where the thing I've been working so hard on might come under a different scrutiny, or might be revealed as actually not being that valuable to the sum total user experience."

But when you see a user struggling, when you feel that sense of, oh, the complexity I'm adding is bad complexity, the dependencies we've created are harmful dependencies that are felt by the user. It's a very different thing. Again, I think a lot of where I've seen really great product leadership... And I love Teresa Torres's book, Continuous Discovery Habits, is always the first book I recommend to people. And of all the things she talks about, my very favorite thing Teresa Torres has added to the discourse is the idea that continuous discovery is the team learns from customers once a week. And I love it because it's so simple. It's the most straightforward thing. It's like, you don't have to use this framework or do this complicated thing. It's like, are you just connected in that way?

Daniel Stillman:

Yeah. That is the best way to get the "product mindset" in the company, is to talk to customers more regularly. How high up should that go? And what can that look like? What is the light... If there's somebody in the C-suite who's like, that's not my job, right?

Matt LeMay:

Yeah. This is an interesting one, because this is one of the conversations that I thoroughly see both sides of. Because I have been in situations where the CEO of a company overhears something, one customer reaches out, and then suddenly that's the only thing that matters. The whole team is scrambling because-

Daniel Stillman:

He's super customer-centric now, which is great.

Matt LeMay:

Exactly. Exactly. On the other hand, I've seen situations where C-suite is super removed from customer. And every time I'd work with companies, it was like, uh-oh, executive's going off to a conference in Silicon Valley and they'd come back and be like, "What's our augmented reality strategy? I saw a talk about it." And it's like, "We're a bank. We don't have an augmented reality strategy. We have a, let's be good at being a bank strategy." But I think in a lot of ways, part of why I think Teresa Torres's definition is so valuable is that it speaks to cadence, it speaks to regularity. If you're doing this on a regular basis, then the odds of any one thing being cataclysmic actually get smaller. I think one of the big challenges, and I've talked to a lot of folks I know in user research about this, is that it is very hard to get to a place where customer research is happening well, without it happening poorly along the way.

Daniel Stillman:

Yes.

Matt LeMay:

If your goal is to avoid a situation where an executive overreacts the customer feedback, if your goal is to avoid a situation where product managers ask leading questions and do the things that product managers aren't supposed to do, you're never going to get there. You have to be ready to manage those situations and navigate them, and have those conversations. And say, yeah, here's what's happening. We're on a path. Let's manage our expectations. Let's look at this. Let's let this happen and manage it, rather than trying to over-engineer a situation where no bad research ever happens. In which case, design or UX or whatever, whoever is managing research will remain a gatekeeper forever, and you will never get in that position where the entire organization is actually participating in a healthy, unproductive way. I think you need to hit some [inaudible 00:29:22] along the way if you're ever going to get anywhere meaningful that-

Daniel Stillman:

I agree. I definitely could see resistance to a weekly cadence as you "go up in an organization". What would you tell a C-suite that says we can't do it once a week? And maybe being on the other side of the glass, once a quarter is something we can do.

Matt LeMay:

Oftentimes, I've sat down and said, "Craig, mind if we look at your calendar and see if we can find a half hour every week?"

Daniel Stillman:

Yeah.

Matt LeMay:

Just a half hour. This is, again, where I find that getting down to the level of tactics can be so valuable here. Because I understand philosophically, I understand emotionally that reaction. Look, I'm so busy. I'm like, okay, let's find one half hour a week.

Daniel Stillman:

Yeah. This is great, because now we're getting towards two other things that we haven't talked about that we should talk about. And one is, we should go back to how do you facilitate large groups of people to come to a decision? But the other piece of that is, you can't get anyone to do anything.

Matt LeMay:

Yes.

Daniel Stillman:

So this comes to, I love the word... This is just, again, I'm a chef who looks at everything like food. When I think about conversations, I think about invitation. An invitation is what insights or initiates a conversation. And cadence is the pace of the conversation, the rate of return of the conversation. And these are two things that are so critical. You cannot force anyone to have a real... You can't force somebody to fall in love. You can put somebody in the context where maybe they'll be open to it. You can't get anyone to do anything. What you were just doing with the CEO is saying, we can do it for 30 minutes on a Friday, or here's another option. You're giving them options instead of saying, hey, it's really important. Because that's resisting resistance.

Matt LeMay:

Yeah. And that fails every time, especially when you're working executives. Yeah. It's interesting, because some of the you can't get anyone to do anything talk started at that conference in Lisbon. Where during the workshop I did so many of the questions I got, well, how do we get product managers to value research? How do we get them [inaudible 00:31:48] work we do? And I felt like I was a dog chasing my own tail trying to answer that, I just couldn't get to an answer. And then I spoke at a conference remotely, unfortunately, in Athens, Greece.

Daniel Stillman:

Because it would've been great to be in Athens, I presume.

Matt LeMay:

A while ago. And it was about this Agile conference, and the first question I got was, how do we get executives to be agile? And it just came to me. I just said, "You don't get anyone to do anything." And the reaction I got was just resentful silence. Just, the room went dead. No follow up questions. That was it. And I said to myself, interesting. There's something there. I've touched a nerve. I wrote a talk that I gave at UX Brighton last year called, You Don't Get Anyone To Do Anything. And I prefaced it with my whole take on Alan Watson, Zen Buddhism, and the idea of you can't capture flowing water in a paper bag. And all that great, it goes through a lot of wisdom tradition stuff across different cultures and different religious traditions. But when I came to, you can't get anyone to do anything. Again, I got this resentful silence.

I was like, no, no, no, no. Okay, we're going to walk through this together, because this is actually the path to freedom. When you convince yourself that you can control other people and get them to do something, or that your success and your "influence" hinges on somebody else doing something, you are setting yourself up for a life of disappointment and misery. You can't get anyone to do anything. That's the path to freedom. You can state your case and try to help people make the best decisions they can. But there's been this great thread running through product management discourse in the last couple months. Michelle Cutler's talked about this, my friend [inaudible 00:33:49] talked about this a lot. That really you're creating the conditions for good decision-making when you're a product lead. You're not making the decision and you're not getting anyone to make a decision.

You're trying to just really align the criteria for decision-making and give people options, and then you help them understand the trade-offs. And if there's a disagreement, then that's in that case constructive. Because you can say, all right, are the options wrong? Are the decision-making criteria wrong? I think one of the things I learned, I remember so clearly being in a workshop about product strategy, the team I was coaching. We were two hours into this and everybody was debating, well, what should be a product strategy? And people were going up whiteboarding things, and having all these very intense academic theoretical conversations. And I said, "All right, can I try something real quick? What are 10 things this team is thinking about building?" And they listed them. I said, "All right, everybody just prioritized them yourself in two minutes, one to 10." Two very different orders emerged.

There were two very clear clusters. And I said, "All right, break into your cluster, spend five minutes preparing your verbal argument. Why is this the right order?" So everyone goes, they're getting excited. The first team goes, "Look, this team is really focused on acquiring new users. So we..." Somebody on the other team goes, "Wait, wait, wait, wait, wait. I thought we were focused on retaining existing users." And there you have it. It wasn't that there was something in page 1,000 of how to write a product strategy that was missing, but was something really simple and really straightforward. We didn't know who we were building for. And in a lot of cases, again, things like product strategy, any of these things that are designed to help us make decisions I find are better to reverse engineer from the decision you are actually trying to make than to try to generate in the abstract.

So if you're trying to get a room full of people to make a decision, see how each person in the room is going to make the decision, and then figure out what they're basing that information on. Then you'll probably figure out what information you need to consolidate or answer or resolve in order for the room to make a decision. But I rarely ever now spend much time thinking or talking in the abstract before asking participants in a room, how would you make this decision right now? If you have these three options, which one would you choose and why? Because that will help me understand what decision-making criteria are necessary, and it'll help me understand if I'm thinking about options the right way.

Daniel Stillman:

It almost seems like prototyping the decision, right?

Matt LeMay:

Yeah. I think that's a great way of putting it.

Daniel Stillman:

You can over facilitate or design a "perfect" agenda for how to architect a decision. Or you can get some people in a room and say, how would we know if this was a good decision? And what are some things you're thinking about would be a good decision for this? And just to mock it up.

Matt LeMay:

Yeah.

Daniel Stillman:

And then in a way, it's iterating.

Matt LeMay:

Exactly.

Daniel Stillman:

Is this a good decision? How do we know? What would make it better? Oh, we're not aligned on it. Okay, well great. So how can we all get aligned on it? And then you can address each component of it one by one.

Matt LeMay:

And sometimes you'll ask people, and everybody just has the same answer immediately. And then whatever the free hours you would've spent on a strategy session might have been a waste of time. Like there are times-

Daniel Stillman:

Well, there's another issue there of, is everyone aligned? Is that good or...

Matt LeMay:

Right. And one of the other things I've learned also, I'll tell another story from a workshop. I was doing the workshop with a bunch of product managers, and I talk about how part of your job is to understand why a decision was made. If your team is given something to do, it's really important for you to understand why. And not to just storm off and say, well, fine, we'll do it. We're like, no, we won't do it. Understand why. And somebody made a noise. And I'm like, huh. "Oh, hello, you made a noise." She goes, "Yeah, I don't agree on it." "Great. Tell me why. Is there a particular experience?" She said, "Yeah, I was told to build something. I kept asking and I kept asking, and I kept asking. And eventually I was told, look, somebody promised this to the board, so you just have to build it. Okay? So now I don't bother asking anymore."

And I said, "Oh, congratulations/I'm sorry you did your job. You got the answer. And getting an answer doesn't mean getting an answer you like." And that's one of the hardest things to accept in life and in product management, is that there will be times where you go and you get an answer, and it's not a good answer. It's not the answer you hoped for. It's not the answer that leaves you feeling awesome, and let you understand exactly why something was done. But if that's the real answer, there are times in real world organizations where you say, okay, great. What exactly was promised? What exactly is the wiggle room in this? [inaudible 00:39:03]-

Daniel Stillman:

Well, why does the board want what it wants is not an unreasonable question. Somebody would say, oh, well... See, this goes back to cognitive behavioral therapy, and our own relationship to power, authority, and optionality. That person heard that and said, well, there's just no point in me asking anymore. And there was somebody who would say, oh, why does the board want that? Why do they think it's important for the organization to be doing this? What is their vision for this organization as opposed to the C-Suite's view for what this needs? Why is the chief of product officer and the board not aligned on this?

Matt LeMay:

Yeah. And I do think there comes a certain point where you might just need to throw your hands up and say, I've asked as much as I can.

Daniel Stillman:

Fair. No, no, totally.

Matt LeMay:

As an IC product manager, I'm probably not going to be able to get much time with the board. But if I know that this is at a certain altitude, and I have a sense... I deal with this a lot with companies that say, "We're a marketing driven organization. Marketing told us to build this thing." Well, then I go to marketing and I say, "What'd you tell them?" "No, this is the story we need to be able to tell, but I don't care what they build. I don't care where the pixels are." And I go back to product and I'm like, "Well, what do you think they meant by this?" "Well, I don't know. They told us to build this."

I'm like, "Yeah, when marketing tells you we're going to build a portal or a platform or whatever, there's so much wiggle room within that." There's so much opportunity to say, all right, not only to ask what does that mean, but to say, okay, when you work in that collaborative, iterative way, it breaks down a lot of the silos naturally. And again, I feel like simple time constraints are such a massive enabling factor.

Daniel Stillman:

Well, and we have a time constraint that sadly we're coming up against. I usually ask, is there anything I haven't asked you that I should ask you? And I do want to ask that question. This thing you're just talking about, I know someone who has this challenge where, I know you said there's no such thing as a product mindset. But if sales are the people who have the most contact with the customer in a particular venture backed startup that shall remain nameless, how might we help them frame conversations so that they are promising stories and not features?

Matt LeMay:

Yeah, here's the thing.

Daniel Stillman:

Is that a-

Matt LeMay:

I think that's a great question. And I think the first thing to acknowledge is that if you work at a sales-driven organization, show some respect to the sales team. I'm a bad salesperson. I'm terrible at sales. And I have so much respect for people who are good at sales. I often say that you can reframe a, how do I get question as a, how do I help question. If the question is, how do I get sales to stop selling things that we have to build? You're going to lose. How do I help sales sell more? How do I help them be more successful?

Daniel Stillman:

Oh, my God, did I do that? How can I get... After all that we just talked about, that you still use a how do I get?

Matt LeMay:

No, no, no, you didn't. You didn't. I'm paraphrasing. I'm conveniently paraphrasing. But I think that at the heart of most questions coming from one function about the behavior or intentions of another function or another person, is this idea that I know how they should be behaving or what they should be doing.

Daniel Stillman:

Oh, God.

Matt LeMay:

And they're not doing it the way I would want.

Daniel Stillman:

My God, you have read too much Alan Watts. This is [inaudible 00:42:32].

Matt LeMay:

I wish I had Alan Watt’s voice. [inaudible 00:42:35]-

Daniel Stillman:

This is the game of black and white. This is the game of black and white versus this is a both and, this is a curiosity mindset.

Matt LeMay:

Yeah. If I go to sales and I'm like, "Hey, I want you to sell more. I want you to make more money. I want to understand how you sell. What can product do to help you make more money for this company?" That's a very different conversation. And-

Daniel Stillman:

Then stop selling features that we have to build.

Matt LeMay:

Right. Because, I'm sure sales is frustrated too that they have to... [inaudible 00:43:08]-

Daniel Stillman:

Why haven't you built this yet already?

Matt LeMay:

Exactly. It can be a win-win when you go in trying to understand what somebody wants to achieve and help them achieve it. And the good news is, in most organizations if you zoom up to a high enough altitude, you do want the same thing. You want the company to make money. Make a lot of money. You want to be successful. Once you get out of your own silo and your own sense of... One of the things I tell product managers all the time is that the things you do to seek personal rewards and recognition will almost always be harmful to your team. The things you do that you feel that are increasing your personal status, your personal visibility, are intrinsically antithetical to how product work plays out. Which is to say, that the group efforts, the team efforts are always the most impactful things. I think once you can really accept that your team's success is your success, your company's success is your success, there's a degree of ego death that goes into good product work. And I think good cross-functional work in general.

Daniel Stillman:

Which is why everyone should be in some therapy so that they can work on preparing for that ego death, which was Socrates' whole perspective. With zero minutes left. I feel like they do always do this on NPR. So with the last 30 seconds, Senator, would you please... If you had a billboard, what would we put on it? We're going to put this, you can see this from space, everyone can read this. What's Matt LeMay's message to all people, especially the C-Suite of developing product organizations?

Matt LeMay:

Yeah. I would say for that audience, I would say focus is a bigger risk than scale. Not having focus is actually a much bigger material risk to your organization than not having scale. And to everyone else I'd say, you don't get anyone to do anything. And I'd tell them to go read The Wisdom Insecurity by Alan Watson.

Daniel Stillman:

Yes, it's a good one. Aside from reading your books, Agile For Everybody, and Product Management And Practice. And going to your website at mattlemay.com. Where else would you like people on the internet to go to learn more about all things Matt LeMay and to stay in connection with you?

Matt LeMay:

I'm more active on LinkedIn than I am on Twitter these days, so you can find me there.

Daniel Stillman:

I saw your conflict about Twitter.

Matt LeMay:

Yeah. It remains a profound conflict in speaking with... And keeping with the idea of decision-making happens, I'm creating the conditions for good decision-making. Yeah. And mattlemay.com. I'd say the second edition of Product Management And Practice came out this year. I'm very proud of it. Or last year. It's a new year, I keep forgetting that.

Daniel Stillman:

Happy New Year.

Matt LeMay:

Real proud of that one. And otherwise, yeah, I think that just about covers it.

Daniel Stillman:

Matt, thank you for making the time for this conversation. This is really great stuff.

Matt LeMay:

Thank you. Yeah, this was really fun. Appreciate it.

Daniel Stillman:

Yay. We'll call scene. 

The Surprising Power of Two Hour Mid-week Cocktail Parties

In 2019 My friend Philip invited me to a 2-hour cocktail party at his tiny apartment in the Lower East side. True to his word, the gathering, which was on a Tuesday night, started at 7 PM sharp, and at 9 PM he kicked us out onto Orchard Street to enjoy the rest of our night and/or to get to bed on time (since it was a weeknight, after all!)

I met a whole bunch of awesome people, and if I’m honest, I thought Phil was super cool for bringing such a lovely group of people together. The food and drinks were nothing to write home about, but no one cared. Phil stopped the party two or three times to get us to circle up and introduce ourselves and respond to an icebreaker prompt. It was pretty fun.

He mentioned during the party that he was following an early draft agenda, a recipe if you will, for such gatherings, that was being developed by his friend Nick Gray, who I knew of through other friends. Nick had started a company called Museum Hack that had blown up - in the good sense. They were leading creative tours in Museums around the city, so I guessed this guy Nick knew a thing or two about getting people together.

Cut to 2022 when Nick Gray’s book “The 2-Hour Cocktail Party: How to Build Big Relationships with Small Gatherings” came out. Here it was, four years later! I was fascinated to talk to Nick because I thought “How much could there be to this? Isn’t it all in the title!?” How much could the form have evolved over 4 years of prototyping and testing?! 

I’ll tell you folks…this is a polished gem of a book.

If you’ve followed my work, you know that I’m a bit of a nerd when it comes to gathering/facilitation/conversation design. I love card decks about it, books, diagrams, narrative metaphors to fuel creative innovation in gathering science for skilled facilitators to bring diverse stakeholders together to tackle wicked problems. I have coached leaders on this skill, all over the world. I hosted many, many cohorts of my 3-month Masterclass on Facilitation that people lovingly described as “drinking from a firehose” of facilitation while somehow being spacious and deeply mindful of how we gather. Managing complex gatherings is a crucial skill!

Companies that can’t come together to discuss and decide on actions for their biggest challenges will not survive! And I love these types of gatherings - they are never the same, they have to be absolutely customized, and deeply considered. 

Nick, on the other hand, has designed the “CheckList Manifesto”, the “Design Sprint” or the “Joy of Cooking”...not for any and all types of gatherings - but for one, single, Life-changing, surprisingly powerful gathering - a 2-hour, midweek cocktail party.

Nick’s book is designed with absolute beginners, or those hesitant or nervous to lead gatherings in mind…but masters of gathering will be pulled in too…I was.

Nick designed this insanely in-depth book to cover everything from snacks to drinks to how to write an invitation to…everything. Where to put name tags. How big those tags should be. You get the idea.

While I am a nerd in the sense of being an omnivorous gathering nerd, Nick is an obsessive compulsive nerd of this one form…and for good reason.

Nick believes, and I now do, too, that if more people felt more comfortable with having more gatherings we would all be more connected. The midweek 2-hour cocktail party just might save the world.

You can get the gist of the form from this conversation (I mean, even from the title!), but if you’re a gathering nerd like me, you'll absolutely enjoy Nick’s insanely thorough guide, which I found myself flipping through regularly as my wife and I prototyped our own first midweek,  2-hour cocktail party, which we titled a “Serendipity Salon”. 

I think we all need more serendipity in our lives, and that’s why I loved the opening quote I pulled from my conversation with Nick - the ability to take a short conversation with someone and turn it into a deeper one, to create a space where your old and new friends can connect with each other…only good things can happen from creating more of that type of serendipity in our lives. My wife and I have hosted two parties like this already and, as Nick has advised, we have our next one in the books! I hope you will, too.

Links, Quotes, Notes, and Resources

How to Host a Party Website

The 2-Hour Cocktail Party: Book info

The 2-Hour Cocktail Party: Amazon

Nick Gray's personal website

3 Tips on How to Plan a Networking Event

Clothing Swap: How to Plan the Party 

How to Host a Happy Hour: Tips, Tricks, and Best Practices

Minute 8

Nick Gray:

Now, one of the key elements of the Nick Party Formula, which is N-I-C-K, name tags, icebreakers, cocktails only, and K stands for kick them out at the end. The N, which is name tags, has become something so natural to me that I don't even think twice about it. But your question made me think, "Gosh, what was it like the first time I used name tags? Why did I use name tags?" And I tell you, I meet so many people, I host so many events that, maybe this has happened to you, people know your name and you... I'm very bad with names or I'm someone who is bad with names at times. And so I said, "I'm just going to start to use name tags from my own need and want, that I don't remember them." And then I saw how much it helped other people. Constant experimentation and then reflection afterwards of who were the best guests? What were the best activities? How did that go? How do I think about that? That's something I'm very, very intentional about.

Minute 15

Daniel Stillman:

So it's very interesting because sometimes new ways of doing help us think and be differently. There can be that transformation of, "Here's how to do it." And I think it will open up things for people. I want to really zoom in on this idea that... So, you mentioned serendipity and serendipity has been one of these words that has been lighting up and expanding for me. Specifically, this term about building serendipity engines in our lives. And so, because doing a party once will not be the engine you're talking about. So, a minimum viable party is not doing a party. In a way, what is the viable party habit in order for it to become an engine of serendipity in someone's life, do you think?

Nick Gray:

Well, and how you can take it to turn it into an engine of serendipity is by always having your next party scheduled on the calendar. Why is that helpful? Because today's Tuesday, as we record this, you go out tonight, you meet somebody interesting either at the line in the grocery store, on the subway, at a party, at a friend's house. What is your next step of action if you think somebody's interesting? I got to be honest, these days it's very rare that, besides me inviting them to a party, that I would say, "Hey, we should really have dinner sometime." That is a reach for me and, I think, for many other people. It requires a large level of commitment, vulnerability, scheduling is difficult.

But what I found from living in New York for 13 years and meeting thousands of people, was that I could invite them to my party and it was a very easy invitation. By the way, that's why I call these cocktail parties. It's not about the drinks. I don't drink alcohol myself. I don't know how to make a cocktail. But the phrase cocktail party encapsulates a social construct of a lightweight gathering where you'll have a lot of little conversations with minimal commitment, where you can bounce. You don't have to be there like a dinner party, you're trapped, you're stuck, that's three hours.

Minute 33

Daniel Stillman:

If you're doing this monthly, what is the cadence that you would recommend to somebody, and how do you create variety of the list from party to party?

Nick Gray:

For myself, generally the advice I tell people is every six weeks or so, you should be hosting something. And I like to invite about half regular people and half new people. And that helps mix it up. Using those words as well, there's always new people. Using that phrase when you explain it to somebody, number one, makes them feel more welcome. They're not walking into a party with established cliques. And number two, makes them not feel left out if they don't get invited again. The idea that there's always new people is something that will make these parties a success.

Minute 37

Daniel Stillman:

Why do the first icebreaker so early in the party? Because I know in your agenda, it's almost right out of the gate, right? It's pretty early in. Everyone is not necessarily even going to be at the party yet. And as an experienced facilitator, I still felt awkward breaking the frame of the traditional party. Which is, things are just kind of happening and everyone's kind of on their own. And to bring in structure early in the party, breaks the pattern and shows people a different sort of thing is happening here. I actually think it takes guts. Even as an experienced facilitator, I'm like, "Oh my God, this is not the place for me to be doing this." So, why do it? And, why do it so early?

Nick Gray:

So as an experienced facilitator, you may appreciate my reasoning on this. Many of my readers have never hosted an icebreaker before. In fact, they're terrified about the idea of leading an icebreaker. And so that first icebreaker, number one, is meant to get them out of the awkward zone. But number two, is to show them that icebreakers work and to make it easier to stop a party with fewer people, to know that when they have to stop it 20 minutes later when everybody's there, that it's going to work.

So it's for the purpose of the facilitator just as much as it is to get out of the awkward zone. The awkward zone is the zone that I describe as the first 10 or 20 minutes of a party when you haven't reached critical mass. Sometimes the people that you don't know the best have shown up early and it just is what it is. It's awkward. We do an icebreaker there to just get the conversations broken up and add a little momentum, create some excitement.

But I really do it for the hosts. I used to hear from so many people, before adding this first icebreaker, they'd say, "Oh, I did the party and then I never did the icebreaker. Everybody was having fun, I didn't want to interrupt it." And what they're really saying is, "I was too nervous. I was a little scared."

More About Nick

Nick Gray moved to New York City with very few friends and less-than-stellar social skills. But Nick craved new relationships and exciting opportunities. He started hosting non-traditional parties—a move that opened doors he never could have imagined.

Today, after hosting hundreds of 2-hour parties, he counts business owners, artists, and inspiring teachers among a circle of friends that helped him launch a multimillion-dollar company, Museum Hack. Featured in The New York Times and The Wall Street Journal, Nick has been called a host of “culturally significant parties” by New York Magazine.

Full Transcript

Daniel Stillman:

Well then I will officially welcome you to the Conversation Factory. Nick Gray, thanks for making time to talk with me about talking.

Nick Gray:

I'm excited to talk about talking, and parties and networking and all those things.

Daniel Stillman:

Well, yeah, because isn't a party just a bunch of people... I mean, I suppose talking is one of the things that's supposed to happen at a party.

Nick Gray:

Yeah, yeah. Parties are a lot of talking. Although now that I think about it, what would it be? Yeah. And so parties are a lot of talking and I've written a book that just helps add a little bit of structure to that talking. What do you think about structured talking? Do you ever show up to a friend hangout with a list of topics to talk about?

Daniel Stillman:

Are you trying to reverse interview me Nick Gray?

Nick Gray:

Yes. Yes. You're the pro. I want to know the expert. What does he do?

Daniel Stillman:

Well, clearly you value structured dialogue. Right?

Nick Gray:

Yeah, yeah.

Daniel Stillman:

Well, I really want to start way back, which is, why did you want to undergo, undertake this project? Because I don't know if you know this, I feel like we talked about this over email, but I went to an early prototype of this formula, our friend Phil Van Nostrand invited me to a two-hour cocktail party in 2019. So, you've been working on this for a really long time.

Nick Gray:

Yes. I've been working on this for a long time.

Daniel Stillman:

Yeah. When did you first start having the conversation with yourself about, this is something I would like to do?

Nick Gray:

Literally, it was over five years ago that I had built a Google doc for my friends that was the outline of this book. And I never planned to make a book, but it was just something I did for fun, for free, for my friends to use when they moved to a new town or want to make friends. And about five years ago, I started to think, "Huh, maybe I'll make this into a book." So I've been thinking about it a lot. And I suffer from the disease of perfectionism, which is to say that, I just wanted to make the book perfect and beta tested and get it into a thousand people's hands before I came out with it. So that's why you went to a test with Philip, which is really proof, I think, if you want to tell your listeners, that is a small apartment and it is proof that you can be successful even in a small apartment.

Daniel Stillman:

It's true. And he didn't have fancy snacks or fancy drinks. He did, at the time, have an outdoor space which was pretty prime, and he was on Orchard Street. So it was a very cool apartment, which I presume you've been to at some point. So I want to go further back then, because why did you write this guide for your friends about how to have parties? Because that's-

Nick Gray:

I got so much-

Daniel Stillman:

... that's not normal, Nick. I don't know if you know this, not everyone does that. Right?

Nick Gray:

Yeah, to do that, I guess. So yeah, I've been writing and sharing on the internet for over 25 years and I got so many benefits myself, from hosting parties. I saw other people get benefits from hosting parties that I think, just like you know the benefit of conversations, I know the benefit of building a network of acquaintances. And I found that I was able to launch my business, have success through those relationships I built up in hosting these parties. And after I sold my business, I was like, "All right, this is my next thing. I want to give back. I want to share that with others."

Daniel Stillman:

It's such an interesting journey to undergo. Why that? You're like, "This is going to be my windmill. I will tilt at this windmill. This is the horizon." I'm sure you could have done many things and you do other things. This is the thing that's so fascinating to me, because recently I wrote an article about what we should do when we think about taking on a new project, because this is something that we are all faced with all the time. And, what made this light up for you?

Nick Gray:

So for me, I think about how much value I can give. What will have the maximum amount of value? And I have found that hosting a party, when I can actually get somebody to host a party, I get to talk to people afterwards. And the level of satisfaction and success and how proud they are and the sense of accomplishment from leveling up in a life skill. Something fun that I like to do is I like to teach people how to juggle. And about 50% of people I can teach how to juggle in less than five minutes. The other 50% will take me hours and I'm not able to help them because I'm not that patient. But about 50%, based on how I see them throw two balls, I can know, "Oh, you can immediately learn how to juggle." And I love teaching people how to juggle because they get that sense, that feeling of accomplishment.

Similarly, with writing this book and with making this my mission, I said, "Wow, this is truly something that, number one, I'm an expert at. I've taught hundreds of people how to host a party and I personally have probably hosted a thousand parties now, and I've learned a specific formula that can make a gathering very, very successful." And I just said, "Yeah. I think if I'm going to write a book, if I'm actually going to share a detailed set of instructions and knowledge and lessons learned, that really is the only thing that I could truly write about that gives massive amount of value." That is my why of why I chose this topic and why I'm obsessed with this goal and, gosh, why I'm spending so much time on it, which is kind of ridiculous.

Daniel Stillman:

It is amazing. Well, so I want to talk about this pursuit of perfection and go back to structured dialogue because it's interesting. You've been interested in structured dialogue for a really long time. Do you have a sense of when you started to be aware of, to understand, to be interested in structuring how people get together?

Nick Gray:

In hosting my parties... So I lived in Williamsburg, Brooklyn when I first moved to New York, and I didn't have a lot of friends. When I first moved to the city, it was for the express purpose of building friendships. I worked in the majority of my 20's in a family business, helping my dad grow a company from the basement of our house into a much larger organization. And I'm so thankful for that time but also, I literally lived and worked with my parents every single day of the week. A fun Sunday for me would be to wake up early, go to Waffle House, and then go to the office where I had the whole office to myself and get work done. Right? It wasn't healthy from a social perspective.

So I moved to New York, I think maybe I was 26 or 27, and I said, "I'm really going to work on making friends." And this is what helped, was a little challenge. My roommates in college had moved to New York and they were very successful. And I sort of felt a sense of rivalry or a feeling that I didn't want to live in their coattails, that I didn't just want to ride and mooch off of their success. And I said, "I'm going to make my own friends. I'm going to learn how to meet people." And I'd go to things like networking events and I just wasn't successful at those events. So I said, instead of going to bad parties, I'm going to bring the party to me. And I learned, through a series of experiments, that by adding a little bit of structure to those parties, I could make them much better for other people, which would then help me make more friends.

Daniel Stillman:

Yeah. Well, let's talk about minimum viable structure. What kind of experiments did you start with? When you think about your early experiments in partying, what was the spark for you to say, "Oh, let me do, blank." What was an early prototype that you ran?

Nick Gray:

Now, one of the key elements of the Nick Party Formula, which is N-I-C-K, name tags, icebreakers, cocktails only, and K stands for kick them out at the end. The N, which is name tags, has become something so natural to me that I don't even think twice about it. But your question made me think, "Gosh, what was it like the first time I used name tags? Why did I use name tags?" And I tell you, I meet so many people, I host so many events that, maybe this has happened to you, people know your name and you... I'm very bad with names or I'm someone who is bad with names at times. And so I said, "I'm just going to start to use name tags from my own need and want, that I don't remember them." And then I saw how much it helped other people. Constant experimentation and then reflection afterwards of who were the best guests? What were the best activities? How did that go? How do I think about that? That's something I'm very, very intentional about.

Daniel Stillman:

So what's so interesting to me about your book, and it is a really, really interesting book, is that-

Nick Gray:

Thanks for saying that.

Daniel Stillman:

So I don't know if you're aware of her work, I've had my friend Kat Vellos on the show, she has written a book called We Should Get Together. And it's about the friendship epidemic, or the lack of friendship epidemic. And you probably know, and many of our listeners probably know some of the statistics, actually Casper ter Kuile talked about this too. He wrote a book called The Power of Ritual, and he talks about how Americans, as a whole, lost one friend on average. Most people, if you asked them, "How many people can you talk to?" And I think you read about this in your book too. Everyone just has fewer people to go to.

And there's this idea, Casper's book is more general, it's like, "Hey, ritual is important and here's the power of ritual and creating ritual. And we lack it, and religion used to provide it and it doesn't anymore." Similar, I think, Kat does have recommendations, but they paint a palette of problems and options and opportunities. And what's fascinating about yours is that it's a bullet. I think it's a really good silver bullet, but it's such a specific, well-polished, well-honed bullet to solve some of these challenges of loneliness and disconnection. And you've stripped so much complexity out of it, you've made it so streamlined. It's such a different approach.

Nick Gray:

So, I like that you said that. And I don't feel that that's an insult, that it's one bullet-

Daniel Stillman:

It's not.

Nick Gray:

Right. It's not, right?

Daniel Stillman:

No.

Nick Gray:

Because my book is very targeted. And one of the biggest things I worry about is people like yourself or people like Kat, who you said, reading my book, which may seem like very elementary-level advice. "Here are the supplies to buy. Remind people to take their shoes off. Put a candle in your bathroom." Right? These are very, very elementary pieces of advice. But what I've learned in talking to hundreds of people, is that nobody teaches the basic skill of hosting. And there's a lot of books, I'm sure you've read Priya Parker's, The Art of Gathering, an absolute classic, that in my mind is written for experienced hosts. It is a very theoretical book that talks about the theory of why we gather.

I wanted to write the book for someone who's never hosted a party before. I want to write a book to take someone from zero to one, to encourage a whole new generation of hosts. And I'm hoping that that's what I'm doing. Turbo hosts, people who host already, yes, they can absolutely learn some interesting things from this book. They'll blaze through it in half an hour. But I also love hearing from people that are like, "Dude, I read your book three times. I highlighted it. My party is in six weeks, I've made all these notes." I literally had a guy who read my book... Yes, thank you. I see on the video, Daniel's holding up a book with a bunch of notes in it. I heard from some-

Daniel Stillman:

Well, because I am a highly experienced gatherer and I still read it being like, "Huh, that is in the weeds. Those are some interesting choices. I don't agree with all them, but those are interesting specific points of view." And I think there is something useful about, as you say, Priya's book is way up in the abstraction level of the why. And yours is...

So sometimes I talk about this, there's a classic thinking tool called the abstraction ladder where you talk about why, intention, with how. And you say, "What are we here to talk about? Gathering. Why do we gather? What are all the reasons why it is important to gather?" And then it is also important to talk about the how, and why is not more important than how. And people need to be specific at some point and concrete about, well how do we gather? Let us actually talk about the nuts and bolts of it. And putting sticky notes into bowls so that you don't forget to put certain things out is a great hack. It's a great reminder. I read it, I was like, "I do do that sometimes and I'm going to do that more often." And good hosts do that, because then you don't forget to put the cheese out.

Nick Gray:

So a lot of my book is about trying to create the MVP, the minimum viable party. Because I believe that the biggest benefits come to those who can make hosting a habit. Now I could have written a book about how to throw the craziest party and a step-by-step guide and, "Do this party to blow your friend's minds." But the reality is that people would read that book and they'd host that party exactly once. Because afterwards, they'd be stressed, they'd be frazzled, their home would be a mess and they'd be hungover the next day. I have found that if you can make hosting a habit, it will truly change your life. And I tried to break it down into the process. I'm looking at that ladder of abstraction and at the very bottom, the bottom tier says process level. That is what my book is 95% process. You're exactly right.

Daniel Stillman:

So it's very interesting because sometimes new ways of doing help us think and be differently. There can be that transformation of, "Here's how to do it." And I think it will open up things for people. I want to really zoom in on this idea that... So, you mentioned serendipity and serendipity has been one of these words that has been lighting up and expanding for me. Specifically, this term about building serendipity engines in our lives. And so, because doing a party once will not be the engine you're talking about. So, a minimum viable party is not doing a party. In a way, what is the viable party habit in order for it to become an engine of serendipity in someone's life, do you think?

Nick Gray:

Well, and how you can take it to turn it into an engine of serendipity is by always having your next party scheduled on the calendar. Why is that helpful? Because today's Tuesday, as we record this, you go out tonight, you meet somebody interesting either at the line in the grocery store, on the subway, at a party, at a friend's house. What is your next step of action if you think somebody's interesting? I got to be honest, these days it's very rare that, besides me inviting them to a party, that I would say, "Hey, we should really have dinner sometime." That is a reach for me and, I think, for many other people. It requires a large level of commitment, vulnerability, scheduling is difficult.

But what I found from living in New York for 13 years and meeting thousands of people, was that I could invite them to my party and it was a very easy invitation. By the way, that's why I call these cocktail parties. It's not about the drinks. I don't drink alcohol myself. I don't know how to make a cocktail. But the phrase cocktail party encapsulates a social construct of a lightweight gathering where you'll have a lot of little conversations with minimal commitment, where you can bounce. You don't have to be there like a dinner party, you're trapped, you're stuck, that's three hours.

Daniel Stillman:

It is much harder to get the check early if it's not working or if it's awkward. It's a high commitment space. So I love this idea, and I agree with you, that having your next party in the calendar is a way to continuously invite people into your circle if you want to. Do you have other intentional engines of serendipity in your life that you could identify?

Nick Gray:

For sure. I send a friends newsletter irregularly that began as just a simple BCC email to my friends. Maybe I send it quarterly or once a year. And I got that from my parents, who grew up in the Air Force, and their friends would move and get stationed at new bases. So they'd send these annual cards with life updates to all their friends that they had met. And I started doing my own version of that to my friends, maybe quarterly, maybe yearly, just what I'm up to, some cool books I read. I tried to add value. But that friends newsletter for me is definitely a serendipity engine.

And it's different. Because now, these days people are like, "Oh, you should start a newsletter." The problem with that is you start it around a topic and ultimately you get bored with that topic. It becomes a responsibility, not an opportunity. When I keep mine to a friends newsletter... I think everybody should have a friends newsletter. When I keep it to that idea of what I am interested in, for people that I know, yes, the audience is smaller, but I maintain the consistency. So I think that's one that I'm excited about.

Daniel Stillman:

That's awesome. Any others that come to mind?

Nick Gray:

I've been experimenting with using social media more, short form video on certain platforms, tweets on Twitter. I haven't seen the benefits that some of my friends share, that once they go viral. I'm probably seeing stuff, but at the moment it feels more like a waste of time.

Daniel Stillman:

Really? Because you are really active and super intentional about creating stuff on Instagram. I look at your posts and your stories a lot.

Nick Gray:

Yeah, I'm trying. I love doing my stories. I love doing my stories. I was reflecting on this with a friend and they said, "Oh, is there any downsides to sharing as much as you do?" And I said... Well, let's take you here for an example, Daniel. I don't know if you've commented on any of my recent posts. You might look at them but if you don't comment, I don't see them. And so many of my friends, I believe, have a relationship with me as a viewer. And so that would be something that's a little different. Yes, I get recognized when I go out. I actually, oddly, get recognized on the street sometimes. It's great and it's flattering, but also it's like, I don't feel that it's a two-way street and sometimes I wish it was more two-way.

Daniel Stillman:

Yeah. Yeah. So I mean, then this becomes a question of how do you get somebody from the sidelines of your life into the center? Because the parties are just the beginning presumably, right?

Nick Gray:

Yeah. Yeah. The parties are the beginning, but they're also better than social media. I do feel really strongly on the power of gatherings. I believe that the purpose of these parties is almost like you're auditioning your friends, and you're auditioning who you want to spend more time with. A party is a chance for you to gather 15 to 20 people and to afterwards be able to say, "Oh my God, I forgot how much I love Dan. Dan is hilarious." I'm going to follow up and say, "Dan, what are you doing this weekend? I want to hang out. Let's try to do something." Right?

Daniel Stillman:

Yes.

Nick Gray:

And so I love parties for that opportunity to reconnect with acquaintances, to look at new people in our lives and to think about who we want to surround ourselves with.

Daniel Stillman:

Yeah. It is like taking that serendipity and just pushing that flywheel and getting it revved up and going again.

Nick Gray:

The serendipity flywheel. That could be a good article.

Daniel Stillman:

Totally. Well, so one thing that I really thought was so interesting in the granular level, the super how level of your book, that is connected to this idea of serendipity, was the language around growing your guest list. And being really specific around, you can bring a friend versus invite a friend.

Nick Gray:

Yes.

Daniel Stillman:

Can you talk a little bit about experimenting around that language? Because it was intentional.

Nick Gray:

Yeah. So many people who read my book want to grow their network. They want a new set of friends, they want to meet new people. Maybe they have the same friends that they do the same things with, but they wonder how their life could be different if they had more entrepreneurs, more writers, more podcast hosts in their life.

Daniel Stillman:

Let me tell you, having more podcast hosts in your life, definitely an improvement.

Nick Gray:

Game changer.

Daniel Stillman:

Game changer. Invite us to your parties.

Nick Gray:

Absolutely. They come with agendas for one, and you know there'll be show notes afterwards.

Daniel Stillman:

We may make a visual map, there may be stickies. Yeah, it's possible.

Nick Gray:

Right? There could be stickies, a visual map, which was awesome by the way. So, thinking about how you really meet new people. And one of the things that I'll hear from people is, "Look, you say in your book you need to have 15 to 20 people. I know about eight people. I know enough for a dinner party but not for a cocktail party this big. How do I get more people to come?" And one of the easiest ways is to ask all of your people, or some of your close friends, to bring a guest. Now I found through experimentation, that that is a very different ask than ask them to invite a guest. Inviting a guest is a simple act of, "Hey, yeah, I'll share the link to it." Bringing a guest expresses intent and action and results. Bring someone with you. Success is that you show up with someone. Inviting a guest, they could say yes or no.

Even in my own experience from hosting hundreds of parties and knowing thousands of people, I still only have at most a 50% success rate with inviting someone and them actually showing up, and that's like on a good week. Why is that? It's not because my parties are bad or they don't like me, well maybe it is, but people are busy. People have things going on. And so I tell people, make sure that you tell them to bring a guest. Ask them, "Who are you going to bring? I'd like to get a head count." And doing that, I think, is very helpful way to grow your guest list and start to meet more interesting people. I have one other master pro tip that I've never shared before that I can share with you because you're into this stuff.

Daniel Stillman:

Oh, I am.

Nick Gray:

So I have a Facebook group for people that have read my book and then hosted their second, third, and fourth parties. And I keep track of everyone who hosts one party, but then if someone actually builds this into a habit, I create a free group on Facebook just to share ideas. And someone was asking, "Hey, I'm really struggling with how do I get more people, more new people to come?" And I remembered the most successful thing I ever did. I said, "Look, I've experimented with a lot. Sending surveys afterwards, asking them to bring a guest. The number one thing I've ever done was the most aggressive thing." And it was the following. I stopped the party after I'd ran one or two rounds of icebreakers, so people knew that I'm a good host and I host a good event, when there was good momentum...

Actually I think I did this towards the end of the party. So everybody was having a great time, they knew that this was a good event. I stopped the party, I turned down the music, I said, "Hey everybody, I need five minutes of your time to help me. I'm trying to meet new people. The reason I host this party is to meet new people. So I'm going to ask you to write down someone's name, write down your own name and someone else's name." Then I passed out index cards and pens. I said, "Write down your name at the top and write down the name of two interesting people who I might be able to invite to one of my next parties." You don't have to write their contact info or anything. I'll follow up with you with an email that you can forward to them and if they're interested, then maybe they can reach out to me.

I passed those note cards out to everybody, they wrote down two names. I got so many referrals because the next day I sent them a nice message. I said, "Hey Daniel, thanks for coming to the party last night. Here's the group photo. You mentioned that I could maybe reach out to John Smith and invite them to the party. Would you mind forwarding them this blurb?" "Hey, my name's Nick. I live in New York. I host parties where I get together interesting people. We have name tags and icebreakers and it's two hours long near Washington Square Park. Write me back if you want to come." It was an easy message with the group photo that they could forward onto somebody. And doing that, in the moment at the end of the party to get the names, was the single most effective thing I've ever done to absolutely amplify all the invitations to my parties.

Daniel Stillman:

Yes. Now, I'm assuming that you didn't put that in the book for reasons.

Nick Gray:

Yes, yes, yes. It's advanced. It's an advanced level thing and my goal with the book is simply to get somebody from zero to one.

Daniel Stillman:

And I think that's so interesting that everything we make is our choices. There's choices inherent in everything we make. And I love that you were really clear and intentional on the zero to one, that you want everyone who feels like they want more connection in their life, that this is one clear action that they can take, which is making a party happen in their lives. And I want to just talk about something that we haven't been specific about, which is the fact that the name of your book, I'll say it in the introduction and this will seem repetitive now that I'm saying it now, and this is a weird meta moment, but it is a two-hour cocktail party. It starts at 7:00 and goes till 9:00, or starts at 6:00 and goes till 8:00. Or I suppose it could go from 8:00 till 10:00 if you're nuts and you hate your friends. And it's in the middle of the week because that's a day when people can actually, you can get people's time. Nobody has anything to do on a Tuesday or a Wednesday.

And the power of... And I think I sent you this on Instagram. Somebody had a sign, it was a cartoon where it was like, "Please leave at 9:00 PM." Knowing that there's a clear ending, where did that inspiration come from for you? Saying, "Look, it's not 90 minutes. That's too short. It's not two and a half hours, it's not three hours." You're like, "Here it is, two hours." What are you optimizing for and what are you sacrificing in that choice?

Nick Gray:

I'm optimizing, first and foremost, the number one thing that I've found that will guarantee the success of a party is simply the number of people. If I can get someone to have between 15 and 20 people to show up and they follow my rules and foundations, I almost know that their party will be a success. Why is that? Because the number one thing that will make a party a dud is if they don't meet the critical mass. A cocktail party works when you have the energy in the room that is exciting to walk around. That gives you the opportunity to meet new people and also a little bit of FOMO that you know you won't be able to talk to everybody. When you have a two-hour party, it's easier to say yes to, first and foremost.

Second, we host the parties only on Monday, Tuesday, Wednesday nights because those are non red level days that aren't socially competitive. A two-hour party also almost guarantees that you'll end it when things are going well. And what I found was that when I end it going well, people are ready to come back. They want to come back. They can't believe that it's being ended early, in their mind, and yet they thank me for it afterwards. "Oh my god, thank you so much." I'm seen as a host who brings leadership to the scheduling. So those types of things for me make it easier for people to say yes, they're happy when they leave, they thank me for it. And also frankly, I like my sleep. I don't want to go to bed at midnight when my house is a mess. I want to go on with life. I don't know, it's a very type A way of hosting parties.

Daniel Stillman:

It's very interesting. One of my favorite Shakespeare quotes... And this is from Romeo and Juliet and it goes by really fast. Most people don't remember this quote because it's not, "What light through yonder window breaks? It is the east and Juliet is the sun," which... Or "Goodnight, goodnight. Parting is such sweet sorrow," blah blah blah, all that shit. It's the scene when they're leaving the party after Romeo and Juliet have met and they've realized, "Oh shit, we're in love with someone who's from the other side." Mercutio comes up to Romeo and says, "Away. The sport is at its best."

Nick Gray:

Wait, that's a great line. Wait, that's incredible.

Daniel Stillman:

Yes. Now he's going to Google it and find out that I'm misquoting it slightly, I'm sure. But Mercutio says this to Romeo, he's like, "Look, we got to go. It's good. The party's good and we're going to leave at the peak."

Nick Gray:

Yes, that's the best.

Daniel Stillman:

Because this is peak end theory, right? Disney talks about this. People can Google peak end theory. So, ending a party at the peak is bold and it's a risky move to say, "You know what? There's more juice here, but guess what? Come back next month."

Nick Gray:

Is the peak end theory the same idea that they say that you should finish a vacation with a high note.

Daniel Stillman:

Well, so you remember the peak experience and then the last thing that happened. So this is one of the reasons why my wife and I talk about this, sometimes changing your location... Like, you stay someplace for 10 days. If you stay in two places, it's almost like you've been on two vacations because you remember, "Oh you remember we were in Athens, that was amazing, that meal in Athens." You're like, "Oh, and when we were in Heraklion in Crete, that was amazing." So you've made two peaks and you remember those two peaks and you remember both ends. And so yes, you want to end on a high note. "Away. The sport is at its best," because that's where people remember it.

Nick Gray:

I love that. In my book I talk about, briefly, how to end your party on a high note. And I talk about ending with a little bit of a cheer. And I do this often at my parties. It seems silly, it seems like summer camp, and yet it adds some finality to that moment. It adds an ending that's distinct, that's definitive and that's, frankly, so different from what most parties do. What do most parties do? Oh, people just start to trickle out, and eventually some people are the last to leave. Or the host makes some thing or some people make, "Oh, let's all go to this bar," or something like that to keep the night going. When you end it definitively, distinctly with some sort of fun activity, she talks about this in the art gathering as well, it really just sets your party apart. And I'm trying to give people a formula to host successful events. That, by adding a little bit of structure, you can set your party apart from a lot of different people.

Daniel Stillman:

You really can. And I can imagine now, your vision of the minimum viable party. We do not have so many of the institutions and organizations that allowed for gathering to be happening more regularly. I can imagine a world where everyone is just like, "Yeah, I throw cocktail parties once a month. I get everybody together." I think that's a better world.

Nick Gray:

I want that world. I want to live in that world.

Daniel Stillman:

Well, you do live in that world, Nick.

Nick Gray:

That's true. That's true. I do spend all day.

Daniel Stillman:

The rest of us are trying to get into that world with you. So one question I have for myself, personally, is do you ever find that 15 to 20 is the optimal number and if you get to more than that it's a different type of party? Do people want to always come back? How do you create variety in your list? If you're doing this monthly, what is the cadence that you would recommend to somebody, and how do you create variety of the list from party to party?

Nick Gray:

So it's a sliding scale of how often you want to host a party. I think you could host once a quarter, you could host once a year. For some people they never host and once a year may be enough for them. I talked to a guy last night at dinner who recently got out of a divorce and sold his business. He has more time and money than he knows what to do with and, for him, I said you could probably host every two weeks. You have a support staff to really do this, you know so many people.

For myself, generally the advice I tell people is every six weeks or so, you should be hosting something. And I like to invite about half regular people and half new people. And that helps mix it up. Using those words as well, there's always new people. Using that phrase when you explain it to somebody, number one, makes them feel more welcome. They're not walking into a party with established cliques. And number two, makes them not feel left out if they don't get invited again. The idea that there's always new people is something that will make these parties a success.

Daniel Stillman:

And so it's being really intentional about the fluidity and acceleration of this serendipity flywheel that you're running and communicating to people. You're not necessarily going to come back every time, but that's great for you. Right? Because I'll invite you to the one that's going to be happening in June and it'll be a different party then.

Nick Gray:

So my worst fear is that someone coming to one of my parties listens to this podcast in advance of showing up to my party, and they show up to the party and say, "Hey I know this is an audition, how do I ace it?" I'm just like, "Oh gosh."

Daniel Stillman:

Well then, I'm sure you have an answer for them. "Just have a good time."

Nick Gray:

Yeah, something like that.

Daniel Stillman:

Well, so I want to talk about icebreakers because it's so important and I feel like they're such a divisive concept. Because there are obviously people in the world who loathe the icebreakers in all forms, and there's some people who value them and crave them. And I imagine that icebreakers had a role in your first business... Maybe not your first business, in the Museum Hack. I imagine you had to gather people and move people around and connect them. How did you get into icebreakers? What was your philosophy of and how has it evolved, of icebreakers? Because I presume early parties, maybe you weren't as adept or adroit and you'd tried some that didn't work. Like before you said, "Here it is. Here's my unified field theory of icebreakers. At 7:10, 7:40, 8:20, these are what to ask. Go." Like you didn't hatch out of an egg with that complete.

Nick Gray:

About 12 years ago, I started to lead tours at the Metropolitan Museum of Art and it was a hobby project that later turned into a big business called Museum Hack. I realized in leading those tours, which again was something I did for fun for free, that I needed to get people talking. And so just like the number one metric for a house party is how many people show up, the number one metric for success for a museum tour was, are people asking me questions? Is this an interactive tour or am I just the sage on the stage who's performing? And I knew, or at least from my own experience I found, I needed people to talk and ask me questions. That massively made the tour that much better for me and everyone else involved.

To do that, I needed to get them comfortable talking in an art museum, which can be an intimidating space. And so very quickly in the first 10 minutes of a tour, I would lead a round of icebreakers that I found were very helpful simply to get people talking. The answers, I didn't care about. What I needed was for them to break the ice and start talking in the sacred space of the museum. That theory and that learnings and lessons came into all this party planning.

Daniel Stillman:

Yeah. Why do the first icebreaker so early in the party? Because I know in your agenda, it's almost right out of the gate, right? It's pretty early in. Everyone is not necessarily even going to be at the party yet. And as an experienced facilitator, I still felt awkward breaking the frame of the traditional party. Which is, things are just kind of happening and everyone's kind of on their own. And to bring in structure early in the party, breaks the pattern and shows people a different sort of thing is happening here. I actually think it takes guts. Even as an experienced facilitator, I'm like, "Oh my God, this is not the place for me to be doing this." So, why do it? And, why do it so early?

Nick Gray:

So as an experienced facilitator, you may appreciate my reasoning on this. Many of my readers have never hosted an icebreaker before. In fact, they're terrified about the idea of leading an icebreaker. And so that first icebreaker, number one, is meant to get them out of the awkward zone. But number two, is to show them that icebreakers work and to make it easier to stop a party with fewer people, to know that when they have to stop it 20 minutes later when everybody's there, that it's going to work.

So it's for the purpose of the facilitator just as much as it is to get out of the awkward zone. The awkward zone is the zone that I describe as the first 10 or 20 minutes of a party when you haven't reached critical mass. Sometimes the people that you don't know the best have shown up early and it just is what it is. It's awkward. We do an icebreaker there to just get the conversations broken up and add a little momentum, create some excitement.

But I really do it for the hosts. I used to hear from so many people, before adding this first icebreaker, they'd say, "Oh, I did the party and then I never did the icebreaker. Everybody was having fun, I didn't want to interrupt it." And what they're really saying is, "I was too nervous. I was a little scared."

Daniel Stillman:

Have you tried-?

Nick Gray:

And so, that's-

Daniel Stillman:

One of the things I struggled with was doing an icebreaker in the round, where everyone gets to hear everyone, versus a paired or small group icebreaker. And I'm wondering if you experimented with multiple rounds of small breakouts versus circling up and having everyone go round the horn. Because it's a very fundamental tension in pushing the conversation out to the edges, versus keeping it in the circle.

Nick Gray:

Yeah. I think you're exactly onto something special, which is that breaking into small groups is a little better. People are more engaged when they can talk more. Some people don't like to talk, but they probably like that more than the anxiety of going around the whole room. The short answer to your question is, you are thinking again as an advanced facilitator.

Daniel Stillman:

I know.

Nick Gray:

You have to remember that this book was written for the zero to one and for them to manage small groups and breakouts... What I find when I break people into pairs, you lose control of the room. You absolutely lose control of the room. And so I lead this activity, it's a module I've written about, I'll include it in the show notes, called Speed Ice Breakers. It's where you pair the entire room up, you split them into two lines, have them face off and you give them all one minute per question and then one line steps down and the other steps back. And you do about 10 minutes, 10 questions. And it's actually very hard. As soon as you release the group, everybody explodes in 10 different conversations. And to get their attention, to get them quiet 10 different times is really a lot of work. And for the purpose of this introductory beginner's book, it just didn't make sense.

Daniel Stillman:

No, it makes a lot of sense. It's about creating a frame that's not hard to explain. And reclaiming the attention of the group is non-trivial.

Nick Gray:

Oh my God, it's so hard. It's so hard.

Daniel Stillman:

So, also so hard, is to finish this conversation because we've just scratched the surface. It is a universe in this grain of sand, Nick. We are coming to the end of our time though. What have I not asked you that I should have asked you? What is important for us to talk about, to touch on that we have not touched on?

Nick Gray:

Well, we don't have the time for it but I would be curious, maybe we could sort of collaborate together on an article for my blog or something. But it's exciting for me to talk about the theory and the advanced facilitation strategies. So things, like you mentioned, that I was writing down, the peak end rule. No one's ever mentioned to me about the theory and the science behind these things. That, for me, I'm just in the weeds, "Put a candle in your bathroom and remove your bath towels." And you're like, "Oh, this is this. And this is this." I'm like, "Oh man, I should hang out with you more to sound smarter." Because I'm just like-

Daniel Stillman:

You're very kind. Well, so the question I want to... And I would be so happy to have a, we call it the 202 level two-hour cocktail party. What is the biggest difference between somebody who reads this book and does nothing and somebody who reads this book and takes action? Because that is your key metric and I think it is the key to transforming, to living in the world that you want to see, which is people are more connected to the people they want to be connected to. So what is the difference between somebody who doesn't throw a party and somebody who does? And what's the difference between someone who throws a party and somebody who develops a minimum viable party habit?

Nick Gray:

So, I would encourage your listeners to think about how their lives would be different if they had a full social calendar, if people invited them out to things, if you had new friends who encourage and inspire you. And know that all of that can happen. In the time it takes you to watch a Netflix movie, you could host a cocktail party for 15 or 20 of your friends. I've written a book that lists a formula of exactly how to do it for under a hundred dollars in supplies in even the smallest of apartments.

If you see on video here, I live in basically a studio apartment. I've hosted many parties in small apartments myself. That is my goal is to reach 500 people to read my book and host a party. There is a loneliness epidemic. We're in a friendship recession, so to speak. And I know that your parties will be successful because you'll help your friends meet other friends. And bringing those people together, I found that everybody wants to know someone who brings people together. All that it takes is a little party.

Daniel Stillman:

Aw. So can I actually just tell you with the one minute we have left, my wife and I ran a two-hour cocktail party in October in preparation for this and because I wanted to gather more. I also run an annual eggnog party. This year's the ninth year I've done it, although we had to skip a couple for the pandemic for reasons that'll be obvious to some people. And this year at the Eggnog party, which was a very welcome return, my friends, my longtime friends, the ones who I have been to eight of the nine or seven of the nine eggnog parties, said, "I met some new people." And that's because we invited several people from, what we called, the Serendipity Salon in October.

Nick Gray:

Nice.

Daniel Stillman:

And for one of my old friends to say, "You really helped me meet some... I love my friends and I love my friend's friends." And if it wasn't for the two-hour cocktail party, my eggnog party, my annual bash of boozy eggnog that I make from scratch in large quantities would not be as rich and interesting. So, thank you for that.

Nick Gray:

Really cool. I want to come to your eggnog party.

Daniel Stillman:

Sure. Well, I have some leftover eggnog, so if you're in New York in the next month or so, you can just drink some of the leftovers. It's good for several months longer.

Nick Gray:

It sounds like a party. Thank you so much for having me. This has been great.

Daniel Stillman:

Nick, thank you so much for making the time. It's been a really great conversation.

Launching a Remote, Asynchronous Venture Studio

Today I sit down with my friend Barry O'Reilly, who’s a co-author of the bestselling book “Lean Enterprise” and author of “Unlearn: How to Let go of past success to achieve extraordinary results”. He’s also the host of the Unlearn podcast. He’s also the co-founder of Nobody Studios, a global and asynchronous Venture Studio in the middle of raising a crowd-funding round (500K so far!) on Republic where anyone (including me!) can be part of their mission to fund 100 companies in five years.

As part of my ongoing series about co-founder relationships, I wanted to bring Barry on to unpack how he and his co-founder connected and decided to make this project happen, how they cross-pollinate insights from venture to venture and how they use a platform-centric approach to create synergies among their portfolio companies.

Along the way, we explore how Barry has learned to leverage serendipity and intentional connection to build his ideal life and lots of insights about how to run remote-first!

Links, Quote, Notes, and Resources

Back Nobody Studios on Republic

Learn about all things Barry here

Minute 10

I always think half, again, to your serendipity piece, half of the fun about people getting to know you is artifacts and finding resonance in different things that you're interested in. I always think it's fun, especially when we're on these, so much of our time is spent on these remote calls that when you have a couple of small artifacts, things that you're interested in, pictures, books or photos. I have my guitar here as well, which I sometimes play people with, which is always super fun. Some people in our team actually, we get on a jam. It's real fun.

Minute 18

What do you feel like you've had to unlearn the most in order to get to where you are now?

Barry O'Reilly:

I think just not being so hard on myself is probably the first thing. When I was in university-

Daniel Stillman:

Do you have a secret for that, for everyone listening? I don't think it's just me and Barry who are hard on ourselves.

Barry O'Reilly:

Yeah, no. It's crazy. I had some experiences where I put myself in very bad positions because I almost had unrealistic expectations for myself. First example was when I was in university, I got into my mind that I had to do well. I had to get a first or an A1 or whatever the equivalent is in the educational system. I put so much pressure on myself to say, "If I don't get that, I've wasted the last four years. I still remember our final exams had eight exams to do and we were on the fourth exam, or the first three had gone really well. But in the middle of the fourth exam, my mind just went totally blank. I mean I couldn't even remember my own name. I sat there for I'd say most of the actual exam period, just staring at a blank page and I couldn't write words. It was one of these sort of first moments where I'd actually realized I'd put so much pressure on myself that I'd sort of flipped, if you will. I had frozen.

Daniel Stillman:

Yeah, you'd basically choked out enough blood to your brain through stress that you couldn't think anymore.

Barry O'Reilly:

Nothing. It was just one of these moments where it's like, what am I doing to myself? It was really interesting and I still remember leaving the exam hall and walking home, whatever. I spent the rest of that day almost sort of totally removed from myself. That was sort of one moment where I really got a glimpse into, "I need to find ways to manage myself." That was probably one of, at the time very difficult, but also a great learning moment for me. Over time, I think all of us and a lot of people like yourself and others who we've big ambitions, we're trying to do bold things. We like to all get outside our comfort zone and do well. What I remembered is that it's not about perfection, it's about excellence and just how can you show up and give your best rather than have to be the best.

Minute 35

Barry O'Reilly:

It's been really fascinating to bring all these people into a collaborative portfolio. This is probably a little bit of a difference from a superpower if you will, that a venture studio has. It's because all the companies in our portfolio are essentially, everybody in each individual company earns equity in the company they're working in, but they also earn equity in the studio as well. So they're collaborative. In many, many respects, and that's very different from a typical venture capital portfolio because they might have three analytics platforms or two food delivery products, so there's competition, if you will.

But in a studio it's collaborative. Also we have this notion of building blocks. So there's companies that are in our portfolio that we use to build companies on top of. A simple example is Thought Format, it's a serverless, no-code platform. We build another one of our products ovations, which is a virtual events platform for speakers and emerging talent on top of that no-code platform. So these businesses sort of first customers if you will, were each other. So they can learn faster, hire trust, iterate quicker, and they have really good conversations at one another to improve both of their products.

Minute 41

Barry O'Reilly:

I always remember one of my, so two of my family are chefs and one of my friends always says, "The sign of a great dinner party is that when you arrive and the person is still cooking and they're cleaning the kitchen as they go." That's the ultimate chef.

Minute 47

Barry O'Reilly:

In the earliest stages of starting companies is a huge lift. It's all the energy to turn the flywheel is manually created by just you showing up, trying to do as much as you can. Push the boulder up the hill if you will. It will always want you to be pushing it.

You have to learn how to self-regulate. This is again, another really strong lesson I learned even going back to this, your point about when I sitting there in university thinking, "Oh, I've got to work the most," or, "I've got to show up the most." Or, "I can't miss a meeting," or. It's easy for people sometimes to fall into that trap. I see it in myself, our team and our founders, but we're also one of our other values is people first in the studio. We constantly, you see the team check in with it one another and go, how are you doing? How's your energy?

Did you have a meeting last night that finished at 10 o'clock and now you're on a call at 4:00 AM? What's going on? Are you okay to do that? There's empathy there. That is because we are irrationally global, the sun does not set on the studio. There is somebody up working at high velocity somewhere all the time pinging you on asynchronous communications if they're blocked. So one of these notions of setting boundaries and having systems is imperative. One of the things I've made an intentional investment about is exercise.

So I literally book time in my diary, just like a meeting, where I go and train. Some of that training is I enjoy mixed martial arts, so I get a trainer to come to my house and we train in the house. Or else if I play sports rugby, I love playing rugby, I play that. These things are systematically built into my schedule that forced me to do them.

More About Barry

I work with business leaders and teams that seek to invent the future—not fear it.

I've been an entrepreneur, employee, and consultant. After several startups, my focus shifted towards venture company creation, and advising entrepreneurs and executive teams where I've pioneered the intersection of business model innovation, product development, organizational design, and culture transformation.

I'm the author of two international best sellers, Unlearn: Let Go of Past Success to Achieve Extraordinary Results, and Lean Enterprise: How High Performance Organizations Innovate at Scale—included in the Eric Ries series, and a Harvard Business Review must read for CEOs and business leaders. I'm an internationally sought-after keynote speaker, frequent writer and contributor to The Economist, Strategy+Business, and MIT Sloan Management Review.

I'm faculty at Singularity University, advising and contributing to Singularity’s executive and accelerator programs based in San Francisco, and throughout the globe.

I'm a cofounder of Nobody Studios, a venture studio with the mission to create 100 compelling companies over the next 5 years.

Founder ExecCamp, the entrepreneurial experience for executives, and management consultancy Barry O'Reilly LLC.

My mission is to help purposeful, technology-led businesses innovate at scale.

Reach out via barryoreilly.com/contact

Full Transcript

Daniel Stillman:

Barry O'Reilly, welcome to the Conversation Factory. This is your first time here.

Barry O'Reilly:

Oh yeah, it is. Well-

Daniel Stillman:

It's crazy.

Barry O'Reilly:

... I wonder what's taken us so long to do this, man?

Daniel Stillman:

I don't know.

Barry O'Reilly:

Well, I'm a huge fan of your work.

Daniel Stillman:

You have a podcast, I've got a podcast.

Barry O'Reilly:

Yeah. No, it's great to catch up and get to do this show together. I have obviously, been a huge fan of your work. I was very lucky to attend one of your short workshops many years ago when, I think, Google were holding their Design Sprint Conference and kicking that off.

Daniel Stillman:

Yeah.

Barry O'Reilly:

And Kai is a mutual friend of ours and I just loved your facilitation class, one of the best classes I've done on that. It's been a pleasure getting to know you then and continuing to know you now, so thanks for having me on the show.

Daniel Stillman:

Thank you, brother. It is, if this is a nice context. How did you know Kai and come to be at the... For those listening, this was a secret conference that was very cool.

Barry O'Reilly:

Yeah, so Kai Haley...

Daniel Stillman:

And I was like how did know these, because there was internal Google people and then there were consultanty, thought-leadery folk like you and me. And it's like I felt lucky to be there with a friend of a friend. So how did you find yourself?

Barry O'Reilly:

Yes. So Kai Haley's a fascinating lady. She actually ran the Design Sprint community for Google inside of Google. So most people probably know Jake Knapp as sort of the advocate. He wrote the book, "Design Sprints," but Kai was basically the lady that trained everybody inside Google how to do them.

Daniel Stillman:

Yeah.

Barry O'Reilly:

So there was a group of people that were trying to advocate for design thinking in UX inside Google. Herself and Jake being just a few of them. But yeah, Jake obviously left Google and went on to Google Ventures, but Kai stayed within Google, ran design relations and started these conferences. I actually met her through a mutual friend, would you believe?

One of the things I used to do when we lived in San Francisco is we would have these dinners where three people would go out for dinner and every other dinner you would give up a seat and introduce another person to come along. So it was a really interesting way to network and meet new people in the city. And the guy who introduced me to Kai, his name is Bruno. He was actually looking after, sort of partnerships for Visa at the time. And yeah, he was like, "You got to meet this friend of mine, Kai." Yeah, that's how we became friends. And me and Kai speak regularly. She's at Coinbase now setting up their international design work. Fantastic lady and I'd highly recommend people check her out and follow her.

Daniel Stillman:

Yeah, I had Kai on the podcast a long time ago. I admired the work that she did inside of Google greatly. [inaudible 00:02:38] Because people do have, there's this story about sprints and like, "Oh, this is how Google works." And it's like, well, it's because Kai and a few other people built a really, really thoughtful train the trainer program, and-

Barry O'Reilly:

Yeah.

Daniel Stillman:

... that did not happen by accident.

Barry O'Reilly:

No, not at all, like you know. And I've worked in companies where it's a very strong engineering culture. My sort of last definitive real job, if you could call it that, was working at a company called ThoughtWorks, which was one of the early pioneers of the agile software movement. And a lot of people, continuous delivery, continuous integration. These types of techniques were born out of there. But it was a really strong engineering culture. I still remember when I joined, it was still a small company, maybe a couple hundred people at the time. And everyone kept asking me like, "Do you write code?" And I'm like, "No." And then the next question was, "Well, what do you do then?" "Oh, you are a manager?" And I was like, "Well, no, I'm kind of interested in building products."

I remember as we brought designers into ThoughtWorks, there was always this sort of reticence against anyone who wasn't writing code. And I know Kai felt a lot of that as well inside Google-

Daniel Stillman:

Yeah.

Barry O'Reilly:

... where it's just a strong engineering culture and trying to bring design thinking, getting people to spend time with customers, doing actual good UX, was the transition the company had to make. And herself, Jake and a bunch of other people I think, should instrumental in that happening.

Daniel Stillman:

Yeah. Yeah, the classic going slow to go fast. Making sure we're having all the right conversations, which as you know is one of my favorite-

Barry O'Reilly:

Yeah.

Daniel Stillman:

... axes to grind, rows to hoe. You mentioned something though that I think is totally worth diving into and was not on the docket at all. One of my most passionate curiosities these days is this idea of having serendipity engines in our life. And I feel like we used to have many serendipity engines. The office was a serendipity engine, coworking spaces, conferences were serendipity engines. Bars. I used to have a Sunday night gathering at a fairly well frequented neighborhood bar for many years. And that's how I made a lot of friends. Now that group of friends has migrated from bar to bar and we still meet together on Sunday nights. It's been 10 years, but it's not the same serendipity engine. It's now more an intimacy engine.

Barry O'Reilly:

Yeah, totally. Yeah.

Daniel Stillman:

The idea of a three person, who started this, or is it just lost in the mists of time? Who started this format and does it still exist?

Barry O'Reilly:

No. [inaudible 00:05:19].

Daniel Stillman:

Is the dinner still happening someplace?

Barry O'Reilly:

Yeah.

Daniel Stillman:

Well it's still happening in the Bay.

Barry O'Reilly:

Yes. Someplace. Yeah. Well, it really started because one of my colleagues at ThoughtWorks, Steve Ambosh, he's a great guy and he was sort of ran a lot of business development in sales and these types of things. But he says someone who's great, at like joining dots. I'm sure those people in your network. He's very kind and liberal with his time, his connections and his network. But he was like, "When I moved to San Francisco," he was like, "Hey man, we should catch up for dinner. Let's you and me, and why don't I just bring someone along that I think you should meet?"

He actually brought Bruno along to this first dinner and they had met at a Salesforce convention. He went up and talked to him because I don't know, he liked the jacket he was wearing or something. Anyway, those two became friends. So we had that dinner and then Dean said at the end, "Well you guys should stay in touch and why don't you invite somebody different onto the next time? That's literally how it started. I met Kai and then at the next dinner I didn't go and I suggested that David Bland, who wrote "Testing Business Ideas," he should go and meet Kai and Bruno. They all hit it off. That was just a little way that we started to network. At different times I'd go out for dinner with Kai and she would bring someone along or vice versa. It was just a great way, especially as I was new in the city when I just first moved there. It was just a fantastic way to meet some great people who've now become great friends.

Daniel Stillman:

This is wonderful. I did an interview last year with a guy Nick Gray, who wrote a book called, "The Two Hour Cocktail Party."

Barry O'Reilly:

Oh yeah?

Daniel Stillman:

So my recent experiment, I love the philosophy of gathering. As you know, you've been in a MasterClass around facilitation with me. I'm a nerd about it. And I think it's great to nerd about.

Barry O'Reilly:

Yeah, you're good at it.

Daniel Stillman:

Gathering in general, but it was, it's so interesting to talk to somebody like you or with Nick who's like, "Here's one recipe," it is the sprint. There is a power to giving somebody a recipe that says, "Here, this will help."

Honestly, I've been running, I ran one in October and I said to my wife, I was like, "Can we do this every month?" She was like, "No, but we can do it every couple of months." We gather 15 or so people, and it's just seven to 9:00 PM on a weeknight. It's like, "Oh, this is a recipe for creating serendipity. It's a recipe." I've been calling it a serendipity salon. It's a recipe for getting people together and a three person mystery swap dinner. Like fascinating. Maybe that should be your next book. The secret to a great career is a mystery, a three person rotating dinner, but we needs a better name. We don't have, what did you call it?

Barry O'Reilly:

I can't even remember what we call it. Was it, "Dinner with Stranger," or something? I can't even remember. But as you say, you can design serendipity and it's such a huge part. I definitely, I would say in retrospect, thinking about my own journey about how I've met people. You have to put yourself in situations for those things to happen, if you will.

Daniel Stillman:

Yes.

Barry O'Reilly:

Even today, I lived in San Francisco for six years and we moved to Manila 12 months ago. Actually, I'm celebrating one year living in Manila today.

Daniel Stillman:

Holy... Has it been a year?

Barry O'Reilly:

Been a whole year. Yeah. Time flies as well.

Daniel Stillman:

I just feel like so recently you were just like, "Ah, my container's not here yet. Oh, it got here, I'm sitting at my desk."

Barry O'Reilly:

Yeah, no. That was eight months. Thank you, COVID and the supply chain damages. Yeah, my container sat in the port in Oakland with oh, 75 ships sat outside the Bay of Oakland for four months.

Daniel Stillman:

Oh dude.

Barry O'Reilly:

[inaudible 00:09:29].

Daniel Stillman:

I feel that that happened to my books during my book launched during COVID and they got stuck in the container someplace as well. So you can stay, but it's not the same thing as, so we're not going to have this video up, but behind you is an Optimus Prime, a really nice one.

Barry O'Reilly:

I got that for... Yeah, my wife got me that. I'm a Lego nut. She got me it for the holidays. Yeah.

Daniel Stillman:

Is that a Lego Optimus Prime? Because I was thinking, "Wow, did he bring this all the way from San Francisco," your Stay Puft Marshmallow Man, the Optimus and the mask. Tell me about the things behind you and how they help you through your day. I'm really curious.

Barry O'Reilly:

Yeah, well, it's super fun. So yeah, I'm a Lego junkie. You might be able to see here. I also have the "Yellow Submarine" Lego.

Daniel Stillman:

Oh.

Barry O'Reilly:

Which is-

Daniel Stillman:

But it's still in its box.

Barry O'Reilly:

Still in its box. The piece de resistance is, I've actually got the original Death Star logo or a Lego down on the bar here. It has to remain covered because my kids, when they see it, will want to tear it apart. So that's one thing, but.

Yeah. I always think half, again, to your serendipity piece, half of the fun about people getting to know you is artifacts and finding resonance in different things that you're interested in. I always think it's fun, especially when we're on these, so much of our time is spent on these remote calls that when you have a couple of small artifacts, things that you're interested in, pictures, books or photos. I have my guitar here as well, which I sometimes play people with, which is always super fun. Some people in our team actually, we get on a jam. It's real fun. But the Stay Puft Marshmallow Man always gets a shout out. I think he's the childs of the eighties. It's the state, they shout it out.

Daniel Stillman:

Yeah, I'm definitely dating myself. Is he a Lego as well?

Barry O'Reilly:

No, he's not.

Daniel Stillman:

No, I was going to say.

Barry O'Reilly:

He's actually a savings. He's pretty cool.

Daniel Stillman:

Oh, nice.

Barry O'Reilly:

Yeah, people love it. Then I've obviously got a, "V for Vendetta," mask because there's something that's quite subsurface about everything I do and contrary. I think if you know anyone who's watched, "V for Vendetta," it, there's a certain type of person it speaks to and I guess I'm one of those people.

Daniel Stillman:

Okay, okay.

Barry O'Reilly:

I kind of love it.

Daniel Stillman:

This is the one of great check-ins that I've done in some of the men's work that I do is the question, "If you really know me, you would know. If you really knew me, you would know." I'm one of those people that, "V for Vendetta," resonates with.

Barry O'Reilly:

Yeah, totally. That's why I've got bee's mask and it reminds me that counterculture taking this sort of path less traveled, all those things that resonate with me in terms of going against the systems, trying to shake them up and innovate them and do something better.

Daniel Stillman:

Yes.

Barry O'Reilly:

That's sort of a lot of the inspiration that I take from the philosophy, if you will, from those types of ed books, films and so forth.

Daniel Stillman:

That's wonderful. So this is actually interesting. You started to tee this up earlier, and this is I think a great place to circle back around. One of my other favorite ways to think about things is the conversation between our past self, our present self and our future self. In the coaching work that I do. I think it's really awesome to hold that space. You started talking about in the beginning of your journey and how you started to... I'm a product person in a technology field. How do you feel like your journey in that started? I'll put this in context. What would that person who at the beginning of his journey, looking at Barry today, how would he understand where you are now? Would he understand where you are? Looking from the beginning to now, would he get it?

Barry O'Reilly:

Yeah. Well, the story is always twists and turns, right? But I think I'm a person who's generally had a clear idea of what sort of vision I wanted to move towards. In some respects, each experience along the way has helped me refine that and get more conviction about it. I started as an engineer, that's what I studied in university. I was a software engineer, I just sucked at it. I would do it for five days a week and one day I would have a flow day, if you will, where I really enjoyed it. But four days of the week, I hated it. I was just banging my head against the wall. I guess at the time, this is 20 years ago, there wasn't really this notion of product management, if you will. But there was the people who came up with what to build and then the people who figured out how to build it.

And I just naturally, because I was in a startup, we were building a mobile games development company at the time. I just started to get this exposure to figuring out actually what were we trying to build, what would the product look like? What were the features? Who would use it? I just actually started to draw towards a natural affinity in that area rather than actually coding it up. That's how it started for me, to be honest. I didn't really call myself a product manager. I was probably more project manager really in that day because somebody sort of had to get the team organized about what they were going to do. I guess that's more what it was called in those days.

From there it really just moved on to working in the startup was great fun. We built this Tamagotchi-esque type cute pet game called, "Wireless Pets." It was the first game to be where you could, phones were had just got connected to WAP, so you could play distributed mobile games and it just exploded. Then that got the business up and running. Next thing we had Sony, Sega and Disney ringing us up to build computer games for them. I built a, "Lilo & Stitch," game in sort of 2002. It was pretty crazy and it just, when we were just a couple of people outside of Edinburgh and Scotland building these things.

Then from there, it really was just a case of each experience I've had more opportunity to either boat work in early stage building companies right through the working and consulting companies to doing my own advisory around that. I always knew over time that I liked the creation process, figuring out ideas, how they can turn into businesses and how you can build teams to get those things created. So I always love travel. So I've lived now in I think maybe nine countries, and this is my first time living in Asia full-time. I've traveled a lot around Asia, but never had it as my postal address, if you will.

Daniel Stillman:

Yeah.

Barry O'Reilly:

This is such a fascinating place at the moment. The Philippines even in itself is, it's the youngest population under 25s, huge percentage to the country is that. It's got the highest percentage of Crypto wallets in any country in the planet. So there's-

Daniel Stillman:

Wow.

Barry O'Reilly:

Yeah, there's so many unique aspects to this whole region as well as the amazing innovation that's happening in places like Indonesia. 400 million people were onboarded it into the internet in the last nine months in Southeast Asia, which is just phenomenal. So there is just some very unique aspects of what's happening in this region. I'd lived in San Francisco for six years before that. It was a great experience. London for five years before that. So yeah, I guess there's parts of me that's not surprised and there's parts of me that is, but I know I like traveling the world and I know I building things. So here we are having fun trying to do it.

Daniel Stillman:

In a way it sounds, what I'm hearing you say is as we look to where we are now, from where we started, it actually sounds like, dare I say, an unlearning of things or letting go of things that you knew you didn't resonate with, that you didn't like. What do you feel like-

Barry O'Reilly:

That's pretty fair.

Daniel Stillman:

What do you feel like you've had to unlearn the most in order to get to where you are now?

Barry O'Reilly:

I think just not being so hard on myself is probably the first thing. When I was in university-

Daniel Stillman:

Do you have a secret for that, for everyone listening? I don't think it's just me and Barry who are hard on ourselves.

Barry O'Reilly:

Yeah, no. It's crazy. I had some experiences where I put myself in very bad positions because I almost had unrealistic expectations for myself. First example was when I was in university, I got into my mind that I had to do well. I had to get a first or an A1 or whatever the equivalent is in the educational system. I put so much pressure on myself to say, "If I don't get that, I've wasted the last four years. I still remember our final exams had eight exams to do and we were on the fourth exam, or the first three had gone really well. But in the middle of the fourth exam, my mind just went totally blank. I mean I couldn't even remember my own name. I sat there for I'd say most of the actual exam period, just staring at a blank page and I couldn't write words. It was one of these sort of first moments where I'd actually realized I'd put so much pressure on myself that I'd sort of flipped, if you will. I had frozen.

Daniel Stillman:

Yeah, you'd basically choked out enough blood to your brain through stress that you couldn't think anymore.

Barry O'Reilly:

Nothing. It was just one of these moments where it's like, what am I doing to myself? It was really interesting and I still remember leaving the exam hall and walking home, whatever. I spent the rest of that day almost sort of totally removed from myself. That was sort of one moment where I really got a glimpse into, "I need to find ways to manage myself." That was probably one of, at the time very difficult, but also a great learning moment for me. Over time, I think all of us and a lot of people like yourself and others who we've big ambitions, we're trying to do bold things. We like to all get outside our comfort zone and do well. What I remembered is that it's not about perfection, it's about excellence and just how can you show up and give your best rather than have to be the best.

Really the thing you're just trying to improve is with yourself. It's not anybody else.

Daniel Stillman:

No.

Barry O'Reilly:

Just how you can get better every day. That was a huge sort of, at the time I would never have called it "unlearning," but it was these things where I was like, "Right, this is a lesson I've got to really take about myself." I see that a lot even today with whether I'm helping startups, working with advisories or working in our venture studio where there's lots of entrepreneurs trying to be successful and build companies. And they're hard on themselves. There's no two ways about it. So I think that's one of the things that I suppose really stands out to me is just it's about the pursuit of excellence rather than perfection. And recognizing that and giving myself a little bit of not so hard on myself as you shouldn't be either, Daniel.

Daniel Stillman:

Thank you. Well, the phrase, giving your best versus being the best is a really interesting and subtle difference because it is the process versus the achievement. It's being rather than becoming, which people have been talking about that since Socrates and Plato. There's a huge difference. I've been actually reading an essay somebody was writing about a book actually, this idea of mimetic desire. There's a French philosopher whose theory is, I think his name is Gerard, that most of the things we want, we want because other people want them. So we see something and we say, "I want that, or I want to be that." Or the way I think of it is, we're living someone else's story. We want to get that A-level because that means-

Barry O'Reilly:

Yeah, yeah, yeah.

Daniel Stillman:

... that we are something that is good. Where do you feel like you got that from? Was that just general society? Was that your folks? Was that something, where do you think that narrative came from for you?

Barry O'Reilly:

Yeah, no. It's really fascinating. I like to get the best out of myself. Well, and that's something that I've always felt in a strange way, I feel that Judy, both to the opportunities that my parents and family created for me and that I've just been given in this world compared to other people. I was lucky to be born into a situation where I was fed, I was clothed, I was highly educated relative to most of the population of the planet. So I feel like there's a... I've always felt even at that level, there was something that I, either you're meant to do and give back. I also played sports at a really high level growing up. So rugby was my favorite sport. I played it at a really high level and I learned a lot about teams and the values that go into creating something great is as a system, it's a group of components of people working together to achieve more.

It's just such a very unique, I found, or took away from those types of experiences. So I just always felt, for me, that's what it was more about. It wasn't necessarily about trying to beat the person beside me, it's just get better myself. I remember even quite recently watching a great podcast with Kevin Hart and he was talking about this idea too as well. For as a comic and a standup, every night he goes out there and he's just trying to make that show a bit better and gauge the reaction.

And so much of comedy in a way is very like a product. You're testing features of the conversation to your point and seeing what resonates, what doesn't. What gets traction, what makes people laugh, what makes people cry is that what your intended response to your action. So there's a lot of things like that that I just enjoy the process, if you will, of improvement, but in a directed way. And so I think that's something that's always been interesting for me. I generally like things where I have to get outside my comfort zone. If the helicopter is leaving in five minutes, there's a 5% chance of survival and most people aren't going to come back. I kind of grab in the bag and jumping on the chopper. That's my jam.

Daniel Stillman:

Is that a movie? Is that a specific movie reference? Is there a specific scene?

Barry O'Reilly:

I'm in the Philippines, so I feel like it's some sort of-

Daniel Stillman:

On the chopper.

Barry O'Reilly:

... Francis Ford Coppola.

Daniel Stillman:

Get down.

Barry O'Reilly:

A platoon or whatever it might be.

Daniel Stillman:

Probably in our, I'm thinking there's got to be a Schwarzenegger movie or maybe it's, "Alien." It's possible. So now I feel circle around. One of the things that always stumps me, I think when we have something big that we've created is the, "Well, how did that get started?" I think about, "What was the first conversation between Steve Jobs and Steve Wozniak?" They had a conversation. They, this is of course my trope, it's they had a conversation and that conversation grew is it's a meet cute in a rom-com.

They had a conversation, then it became another conversation and then somehow they were making a company. You mentioned before we got started that Nobody Studios, the venture group that you're launching, creating is LaunchED. You have not met these, a lot of these people in person. It's like how does that conversation get started to, I think of it as the old movies where it's like, "Hey everybody, let's put on a show."

Barry O'Reilly:

Yeah, yeah.

Daniel Stillman:

You're putting on a big show. Somebody's doing the props, somebody's got the lights, we've got costumes, there's a script, we're selling tickets. It's a whole show.

Barry O'Reilly:

Yeah, no.

Daniel Stillman:

It's like, "The Muppets Take Manhattan." That's my eighties reference.

Barry O'Reilly:

Yeah, no. It definitely feels like, "The Muppets Take Manhattan." I think that's definitely what the startups can feel like.

Daniel Stillman:

Who's Kermit in this? Who's Kermit in this analogy?

Barry O'Reilly:

I'm trying to remember. I definitely had Kermit as a child, but actually my favorite was Fozzy Bear. So because I like the gags. So that's always there, the one that resonated for me. But yeah, as you say, at the end of I guess 2019, I was living in San Francisco, I'd been doing advising at for probably, I don't know, it felt like independently for maybe seven years. I'd just been working with a few startups and done some advisory seats and it just really reminded me how much I loved building. I was missing building. One of my friends who was with me on one of the companies I worked on, Agile Craft, which we sold to Atlassian, it's like Jira Line now. His name's Lee Degal. Lee was sort of, yeah, he sort of reached out to me and was like, "Hey, I've met this guy, Mark McNally, who I think you should have a chat with him.

He introduced me to Mark and Mark was, literally, I'd never met him before in my entire life. He lived in Orange County, he's done 14 startups and was trying to create this thing called, "Adventure Studio," which the idea being, "Could we create an entity where you raise capital, you have a bunch of ideas, and then you build teams to go after those ideas and try and build these early stage or pre-seed stage companies." Incubate them, fund them, incubate them, support them, and then try and grow them and get them acquired. One of the things that I enjoyed about my time at ThoughtWorks is that you would work on lots of different projects and lots of domains. And one of the things I liked about advising was that you'd be helping teams as they build businesses. So I just felt like this was the perfect crucible for me to bring all my skills to bear and actually create equity in something.

Beyond that though, to the, "V for Vendetta," we sort of had this idea that venture is so locked up. It's a place that most people don't really get access to. Often, you have to be a high net worth individual to even invest in early stage companies. So one of the other things that Mark had mentioned is this notion that he was going to try and crowdfund the financing of this startup in a way where anybody, whether they were retail investor, which means everyone from a bus driver to a nurse, a restaurateur would be able to own a piece of this company. So we would, if you will, give access to more people to bring their talent, their influence and their capital to an entity where they could help build startups that are going to have a massive impact on their future. So the mission was fascinating.

The constructs was perfect. I did a call with Mark's when he's sitting in his garage and he had a really sort of to your point about what's in the back of your phone calls, he had this really perspective sign that just said, "Nobody Studios," on it. I was like, "Man, I love this name first of all. He's like, "Yeah, because, "Nobody," we park your egos at the door just people might have done lots of things, but we're trying to create something together." I just had a huge amount of resonance with one another. Yeah, we spent the next three or four weeks talking to each other and really just talking about the vision for what, "Nobody," could be and the values that it would have to represent that started the conversation where Mark had been in his own journey to reflect on his career and figure out what he wanted to do in the second half of his career, if you will.

I was just looking to start putting my energy into something that would create something much longer and lasting than me, create equity for myself and for putting energy in. Then something that could have a real impact, social and economic impact for people that were involved. So it just ticked all the boxes. Here we are two years later, we're on a mission to do 100 companies in five years. We've got 11 in development, four in the market. We've just launched our crowdfunding, which very kindly you are an investor as well. So welcome to the Nobody.

Daniel Stillman:

I think of myself as a symbolic investor, but I wanted to be part of the-

Barry O'Reilly:

No man.

Daniel Stillman:

Part of the journey.

Barry O'Reilly:

No, you are. Yeah. That's what, you're a nobody, that's what it's all about.

Daniel Stillman:

I've always wanted to be a nobody. Now I am.

Barry O'Reilly:

Now you feel the counter-culture when you say that.

Daniel Stillman:

Yeah.

Barry O'Reilly:

That's why we love it. It's like people joke, they spend so much time trying to be somebody to become a nobody and here we are. It's [inaudible 00:32:28].

Daniel Stillman:

I just want to give my best versus be the best.

Barry O'Reilly:

You know it, brother. That's it. That's exactly it. Yeah, it's just been super fun. Here we are now, the campaign is live. We're ticking over raising half a million dollars. We've got a couple of hundred investors from people all over the world. It's been amazing and we're only getting started. So it's super fun times and hopefully there's like people listening here who might be interested and go and look at thinking about what they want to become a nobody too.

Daniel Stillman:

Yeah.

Barry O'Reilly:

I'm nobody. Who are you? Maybe you're a nobody too.

Daniel Stillman:

What do you feel? So we're in this moment where I'm hearing the weird Al Yankovic song, "Dare to be Stupid." You have to put all your eggs in one basket, but that is what you're taking the things you know and instead of advising seven or so companies disparately, it seems like the concept of a venture studio is trying to achieve some sort of nuclear fusion. That there is some sort of sustaining heart of innovation, that there is a way that... Because I'm new to the concept of a venture studio. You and I had a conversation offline where you're like, "Anybody can start one. You could just be two guys in a garage." But if it's a good venture studio, I presume there is some knowledge, resources and approaches shared amongst companies. What-

Barry O'Reilly:

Yeah, no.

Daniel Stillman:

... do you feel like that beating heart is of a venture studio?

Barry O'Reilly:

Yeah. So it is very much an emerging asset class. A lot of people have felt, if you will, that especially over the last few years, the valuations of startups have just gone crazy. These friends of mine, even in San Francisco were getting funded millions of dollars with just a pitch deck and not even a prototype. It was blowing my mind that a lot of the checks and balances have just disappeared from the system in some respects. And VCs have a lot of capital that they need to deploy, are paying high prices for startups that have not really sort of if you've validated or proven that they've got traction. So one of the ideas really was, "How do we get back to doing things a little bit more frugally about creating companies?" So at Nobody, we invested about a quarter of a million dollars to incubate companies over 12 months.

The idea is that we're taking it, something from a post-it note to a prototype to a working product. That when it sees sort of traction in the market, then we would go to get an external capital and funded. So it's sort of a part of the ecosystem we believe that has lost it, maybe a little bit of its natural built in checks and balances. So we think that we can create very high quality early stage startups that have to go through a sort of a quality bar, if you will, to make sure that they're performing before we either keep investing in them or we look for external folks to invest in them. So it's real fund that we have our own ideas that we work on, we've identified or met some early stage founders who might have ideas or early prototypes and have come into the studio.

It's been really fascinating to bring all these people into a collaborative portfolio. This is probably a little bit of a difference from a superpower if you will, that a venture studio has. It's because all the companies in our portfolio are essentially, everybody in each individual company earns equity in the company they're working in, but they also earn equity in the studio as well. So they're collaborative. In many, many respects, and that's very different from a typical venture capital portfolio because they might have three analytics platforms or two food delivery products, so there's competition, if you will.

Daniel Stillman:

I see, yeah.

Barry O'Reilly:

But in a studio it's collaborative. Also we have this notion of building blocks. So there's companies that are in our portfolio that we use to build companies on top of. A simple example is Thought Format, it's a serverless, no-code platform. We build another one of our products ovations, which is a virtual events platform for speakers and emerging talent on top of that no-code platform. So these businesses sort of first customers if you will, were each other. So they can learn faster, hire trust, iterate quicker, and they have really good conversations at one another to improve both of their products. So there's some natural little superpowers that we have in the studio that aren't necessarily available to typical venture capital portfolios, incubators or accelerators like Y Combinator where it's basically a competition, right?

Daniel Stillman:

Yeah.

Barry O'Reilly:

All great, all great picks, three companies to win. So it's not collaborative. So that's why we've tried to bring our mix to having raising capital that we can invest in ideas, people bringing their talent that they can help build ideas, and then us bringing our capabilities to help those founders build faster and be more successful quickly.

Daniel Stillman:

So given that everybody's remote, going back to the beginning of our conversation around three person dinners and serendipity salons. In the same way that Google Sprint, the Google Sprint style that lived inside of Google evolved and grew over time as part of many conversations, collaborations and people committed to growing that community effort. What are the mechanics for creating that collaboration? If we were to look under the hood?

Barry O'Reilly:

Yeah, it's hard.

Daniel Stillman:

How do we structure it? Yeah.

Barry O'Reilly:

One of the things I probably have learned along the way is that asynchronous communication is a skill. It's a skill that even pre-pandemic most people didn't have. Even through the pandemic, I don't think a lot of people learned good practice of it. I think everybody was waiting for it to end. So one of the things I think we learned very early when we were starting to build this business is that the discipline of writing things down, of having a clarity and almost standard operating procedures about how you run meetings, how you capture notes, how you communicate afterwards, where do you put content that you want for discussion and feedback? How do you make sure that people are engaged? How do you reach folks? Some people like to be on Slack, some people like to be on WhatsApp, some people like to read emails still. There's so much coordination about conversation design, which actually made me think a lot about the work we did in your workshop to be honest.

These simple things like readmes. I remember we did this and your workshop too, you made us draw shield to represent different parts of us. These sorts of and techniques are so powerful when new people join a company that if I've like a read me file, it's like, "Read me. I'm Barry. I live in Manila. These are the hours I like to work. This is the best way to communicate with me. Here's if you need any documents. This is the style of my meeting deed, here's my phone number."" All of these small little things have such a huge impact when you're working remotely and asynchronously because it's not like you bump into people in the hallway and go, Hey, oh, you're in my department too? Cool. We all sit together. We'll go for lunch." So you have to create the signposts and you have to create the content to help people collaborate successfully. That's been one big aha. I think that, yeah, I'd be curious for your thoughts on what you've seen through that time.

Daniel Stillman:

I mean we're talking about in a way hygiene.

Barry O'Reilly:

Man. We talk about tidying up all the time. Tidy as you go. Every so often it's like we got to clean the he. It's like, but it's really, it's like honestly.

Daniel Stillman:

That's what great chefs do. Great chefs tidy as they go.

Barry O'Reilly:

Damn right. I always remember one of my, so two of my family are chefs and one of my friends always says, "The sign of a great dinner party is that when you arrive and the person is still cooking and they're cleaning the kitchen as they go." That's the ultimate chef. I was like, "Yeah, okay. Cool." But it's so true because this stuff can get un-wielding very, very quickly. And I think that's one of the things that's certainly learned along the way is every so often we have to clean up all the Slack channels. All the orphan channels that have got the same, Nobody town hall, Nobody hall town, Nobody water cooler, Nobody, Nobody. You're like, "What are these things?" Because people come to the company, people go from the company and when they join and there's confusion about where to go, these are always good signals that you don't have good information architecture if you will. And you're not moving information around.

Daniel Stillman:

So that's like, that's platform. I guess one of the things I'm thinking about is structures or mechanics of connection versus a person or people who are those connectors?

Barry O'Reilly:

Yeah. Well, so I think the third person we hired in the company was Thacha Thacker is the Chief Culture Officer. She was actually an employment attorney who got so frustrated with having to defend people in courtrooms that she was like, "I need to go upstream if you will and see if I can address this problem further in the value stream if there is that thing." She was one of these things that we talk a lot about because one of our values is irrationally global and the team are from-

Daniel Stillman:

Irrationally global?

Barry O'Reilly:

Global. Yeah. The team is everywhere. I'm in the Philippines, we've got people in Hong Kong, Singapore, Israel, Dubai. We got people in Italy, Dublin. We got London and all the Americas. We don't have anyone in Africa and Antarctica yet. That's our goal is to get a team set up there, but already we've got a hundred plus Nobody's all over the world, which means our meetings are instantly global. So this morning we were doing our portfolio review and I had to get up at 4:30 AM or it was at 4:30 AM my time. So I had to get up at 4:00 AM and that is the way to try and get a portfolio review where you can cover Asia, Europe, the Americas and Africa. People have to flex. So it's fascinating as well just recognizing how to work both remotely, across different geographies and cultures because what works in downtown New York in your neighborhood is very different from how people respond in London and [inaudible 00:44:20].

Daniel Stillman:

You know how we do downtown as we said.

Barry O'Reilly:

Yes. Yeah, exactly. Right? It's been fascinating again to see that sort of culture emerge and find ways to communicate. Yeah, no. It's a work in progress as always. But I think that and the advent of video, we use a lot of video.

Daniel Stillman:

You mean like asynchronous video?

Barry O'Reilly:

Yeah. So we do a lot of everything from live streams to tools like Loom where you can record five minutes and send it to people.

Daniel Stillman:

Loom is amazing.

Barry O'Reilly:

So it's really fascinating that how important the gesture goes with the commentary if you will. Because especially when there's a lot of feedback on prototypes, mock-ups or the ability to put video with sound is really quite fascinating. Even in our hiring process as well, we ask people to create a video and talk a bit about their inspiration. Why they found the studio, what inspires them about it? Because it's a huge part of how we communicate with one another. Yeah, so it's fascinating just trying these little experiments as you go along.

Daniel Stillman:

So one other thing I'm curious about is I've been doing a series around co-founder relationships and similarly to you and your relationship with your co-founders at Nobody Studios, each company is got their own conversation of, "Oh, this is what we're doing, this is why we're doing it." They have their internal conflicts as you're saying, "Going up the value change to understand how do we build the company that each one of those people has their own opinion about, the type of company that they want to build."

Barry O'Reilly:

Oh yeah, for sure.

Daniel Stillman:

One message I heard that I'm wondering how you communicate to each of your founders is this balance between giving your best versus being your best, versus running on fumes and creating systems. Because it's not sustainable to.

Barry O'Reilly:

No, not at all. Right. The fascinating thing about Nobody is, so I'm a co-founder of Nobody Studios, but we're also co-founders of all the companies we create. We're not an overlord looking over these portfolio companies with judging them. We're actually co-founders of them with them. So there are kids too. We want them to be successful. So even that dynamic between, if you will, the CEOs of the NewCos and us as co-founders of those businesses is fascinating to consider. But to your point about managing expectations and just energy, because that is what I have found is so important. In the earliest stages of starting companies is a huge lift. It's all the energy to turn the flywheel is manually created by just you showing up, trying to do as much as you can. Push the boulder up the hill if you will. It will always want you to be pushing it.

You have to learn how to self-regulate. This is again, another really strong lesson I learned even going back to this, your point about when I sitting there in university thinking, "Oh, I've got to work the most," or, "I've got to show up the most." Or, "I can't miss a meeting," or. It's easy for people sometimes to fall into that trap. I see it in myself, our team and our founders, but we're also one of our other values is people first in the studio. We constantly, you see the team check in with it one another and go, how are you doing? How's your energy?

Did you have a meeting last night that finished at 10 o'clock and now you're on a call at 4:00 AM? What's going on? Are you okay to do that? There's empathy there. That is because we are irrationally global, the sun does not set on the studio. There is somebody up working at high velocity somewhere all the time pinging you on asynchronous communications if they're blocked. So one of these notions of setting boundaries and having systems is imperative. One of the things I've made an intentional investment about is exercise.

So I literally book time in my diary, just like a meeting, where I go and train. Some of that training is I enjoy mixed martial arts, so I get a trainer to come to my house and we train in the house. Or else if I play sports rugby, I love playing rugby, I play that. These things are systematically built into my schedule that forced me to do them.

Daniel Stillman:

Yes.

Barry O'Reilly:

I actually invest in paying for a trainer because it makes me do it. If I just had a meeting in there saying, "Exercise," nine out of 10 times I'll take another meeting. Because it's just the exercise time.

Daniel Stillman:

Right. The system, the accountability to another person like the change of context. This is really, really true.

Barry O'Reilly:

It's amazing. Right?

Daniel Stillman:

Yeah. What other systemic approaches would you suggest to co-founders getting started to make sure that the Boulder pushing part and the next phase, which is running after the boulder, I presume on the other side of the hill.

Barry O'Reilly:

Yeah, we're getting there.

Daniel Stillman:

Because there is that part where you're running after the boulder and you're like, "Oh, we have to hire people and we have to suddenly be more capable of in things that we never thought we had to be capable of.

Barry O'Reilly:

Yeah, no. We're there. We're there right now at the moment. Yeah, because again, it is relentless. The demand for energy never goes away. It's all there. So I have to really be intentional about managing my energy, setting those boundaries, putting systems in place like exercise and what I eat, when I eat. One of the companies we're building is actually with Dr. Gina Poe. She's one of the leading researchers on sleep and dreams in the world. She runs the sleep lab at UCLA, previously at Harvard. This is one of the fun things about working in a studio, Daniel, because health and wellness is a big part of the studio. We've loads of ex UFC fighters and all these what I would call, "High performance bio-hackers." It's just hanging out with these people. You suddenly are like, "What?" So Gina Poe has been teaching me about sleep and it's, I am now, I will not for hell or high water sacrifice not getting a minimum of seven hours sleep every day.

So just as for men, especially if you're getting six hours or less sleep of hours a day when I'm in my early forties now, I would have the equivalent testosterone rate of a man in his mid fifties. Which is, and this is huge because in order to the two leading indicators for longevity and high quality of lice, what the muscle mass is one of them, your ability to actually maintain your strength if you will. The other is the qualities of sleep that you get. So I'll just sit there going, "These are the leading researchers in the world who have been studying this for 20 years and they're telling me these things. So if I don't design them into my approach to getting better and managing myself, if you will, and I'm not listening to the lecture, if you will." And-

Daniel Stillman:

Yes.

Barry O'Reilly:

So it's all a design to me. I know you enjoy this too as well. It's a design problem.

Daniel Stillman:

It is a design problem.

Barry O'Reilly:

Then if so, I can experiment. I can, all these simple things that I have become quite focused around. Because if you want can put on biometrics like a whoop or aura ring and you can see the difference when you get less sleep, when you eat, aren't exercising when you aren't. So those have become real core tenants of me managing my energy so I can give that energy both to myself and the teams that we're working with. So we're all our best. Sure there's times where you stretch and you flex, but that cannot be sustained. I think we're good as co-founders recognizing that in one another and saying, "You should take a week off, you should not take those calls in the afternoon."

You should... You're wedded to these people because you're trying to do something totally irrational. Like a startup is totally irrational. You have an idea that to try and build something from nothing, does anybody want to join me in doing that? It's, there's a 5% success rate actually lower than that. So I think we've really become friends though you go way past colleagues because you live in people's lives together to create this. It takes that much energy and I think that's one of the things we've been really good is taking care of one another.

Daniel Stillman:

That's beautiful. I love the idea that earlier you were talking about the synergistic effects of companies within the portfolio utilizing platforms and it sounds like sleep quality is going to be a new foundational component of-

Barry O'Reilly:

Yeah, SleepCloud. Check it out. It's coming to an app store near you soon.

Daniel Stillman:

Well, and if anybody's listening, so my hack, by the way, Barry has been at many people suggested keeping my phone plugged in another room. Because reading the phone before bed does not help you go to bed.

Barry O'Reilly:

Nope.

Daniel Stillman:

I have a brown light e-Ink tablet that I read fiction on before bed and-

Barry O'Reilly:

Nice.

Daniel Stillman:

... and blackout curtains. They're the best.

Barry O'Reilly:

There you go.

Daniel Stillman:

Those are my hacks.

Barry O'Reilly:

Yeah, well that's it. But it's all part of the design and I, like that. That is, if you asked me these questions 10 years ago, I would've been like, "No, the way I relax is I have a glass of wine, I do these things. I stay out late or I unwind my friends." But as I've evolved both physically myself and as I get older, but also just being more in tune with, these are the things that help me be at my best. I get frustrated if I don't show up as I know I can.

I think that's being, again, a learning part. I wouldn't tell myself 10 years ago not to go out, have fun and have a white, red wine. That has shaped me to who I am today. Absolutely. I think it's just, I've learned that for the tasks that I'm trying to do today, there's the way they help me be my best requires changes. Those things like exercise, sleep, diet, and also this idea of, to your point about serendipitous conversations, I work from home. So every two weeks I go out and meet someone new for lunch.

So I go and experience like being with people here that I've never met before, whether it was in the Philippines or in San Francisco. I do those things because they give me a change of mode. They give me a different way to look at the world and meet new people. So I try to be as intentional as I can thinking about the things that have helped me, both systematically and serendipitously and work them in. Yeah, hopefully I keep persisting with that and it's working for me as far as I can tell. I think it is.

Daniel Stillman:

Well, this is continuous improvement. We have to notice.

Barry O'Reilly:

Right on.

Daniel Stillman:

We have to be intentional experiments and intentionally noticing. "Oh yeah, that works." I mean there was a guy who hilariously tried to do the sleep pattern that I think it was like Leonardo da Vinci did this thing where he would sleep for 90 minutes every... Or he'd spread out his sleep schedule and he did something. He totally, he was maybe the original biohacker and it worked for him and a guy tried it and he was like, "I don't actually, turns out I don't have enough creativity to fill all the time that Leonardo da Vinci did." So I'm going to go back to it.

Barry O'Reilly:

Well, here's a tip for you man, that as Gina Poe has discovered that there is a rhythm to sleep cycles and surprise, surprise, guess what the time is?

Daniel Stillman:

What? I couldn't...

Barry O'Reilly:

It's 90 minutes.

Daniel Stillman:

Is it really? Wow. Leonardo. Biohacking to the truth. Well listen, I, it's very late where you are. You've had a long day. Is there anything I have not asked you that I should ask you. What haven't we talked about that we should talk about?

Barry O'Reilly:

No, I just, I've enjoyed catching up as much as sharing some of what I've been trying to do and hearing more of what you've been up to as well. So yeah, thank you very much for having me on the show. It's always a pleasure to spend time with you and I welcome as well to the Nobody Network. I'm looking forward to again, to you come and talk to all our portfolios about designing great conversations. I think one of the great parts of building these companies is every nobody can bring their talent, their influence and their capital, and you've abundance to bring in all of those things. So I appreciate you very much and thank you very much for supporting us and being part of the Nobody journey. I think it's going to be a pretty fun adventure.

Daniel Stillman:

So where should people go to learn more about being part of, because there's just one month left. When this comes out, it'll be less than a month.

Barry O'Reilly:

Oh, great. Yeah, right.

Daniel Stillman:

To be part of the crowdfunding part of things. Yeah, well after that what can they do?

Barry O'Reilly:

We may never raise funds again, so this might be the only time we ever do it. So yeah, please go to republic.com/nobodystudios and there's lots of information. You are buying securities, so don't be surprised. We have to go through the same level of, if you will, sort of rigor as a SEC regulated IPO in some respects. So yeah, be, go have a look at what we've shared. If you've any questions we're constantly doing live streams. Ask me anything open, Q and A, so you can find that on at Nobody crowd, pretty much everywhere in all your favorite social platforms. Thanks again for having us.

Daniel Stillman:

Thanks for making this time, Barry. I know your system was like, "Daniel, none of the times on your podcast schedule match Manila time." I'm like, "Good point." That is a solid, solid point because my working hours are usually, I know that I'm not usually my best at 7:30 in the morning. That's my a [inaudible 01:00:34] experiments.

Barry O'Reilly:

Well you have been today experiment. Thank you very much for that.

Daniel Stillman:

Well, when you texted me and you're like, "Can I have 10 more minutes?" I'm like, "Yes, I will enjoy my shower now." Because I was about to run in and run out. So thank you for giving me an extra 10 minutes. I really appreciate it, Barry.

Barry O'Reilly:

Thank you. Appreciate you too. Thank you very much.

Daniel Stillman:

Well then we'll call scene. I think we can successfully do that.

Barry O'Reilly:

Nice.

Conscious Collaboration: Co-founder Conversations

In this conversation, I sat down with Beth Bayouth and Mario Fedelin, the COO and CEO (respectively) of Changeist, a non-profit organization dedicated to youth empowerment. They are building a community of young people that utilize their personal agency to create a more just society. 

Changeist’s programs help 11-26 year olds learn a common civic language, engage in dialogue, and build community to investigate local and global social justice issues. Participants also work with other local community-based organizations to implement local solutions to local problems.

Together, Mario and Beth explore how they met, built a relationship and decided to work on this project together…and how they continue to manage themselves and each other in the entrepreneurship journey.

A few insights we’ll unpack about conscious co-founder relationships:

  • The key to a great co-founder relationship is that both of you do not fall apart at the same time!

  • Fighting Well and how Cofounder Intimacy can help: With cofounder intimacy, there is an understanding that often there’s something else behind a conflict or a mood. Because when you're close, you tend to know about what’s going on or that it’s safe to ask.

  • Knowing yourself and your skills

  • The Power of working with someone with a Different Skill Set but Similar Values 

On Knowing yourself and your skills, and finding compliments on your core team: 

A great leadership team requires Comfort with yourself and your skills and Respect for the skills of others... and it takes Balance - but Balance of what?!

On a leadership team you need:

+ Architects and Visionaries

+ Multipliers - someone who brings something you do not have to the table, who is also committed to the vision and the journey

Another way to think about this is that you need:

+ A Balance of Openers and Closers on the team.

This is the essence of conscious collaboration - knowing if you are more comfortable in a generative or divergent mode, ie, opening, or are more natural in the “Synthesizer” role - organizing, closing, or planning towards action. Mario owns his limitations as a “closer” and intentionally chose Beth as a COO for her natural “shark” skills - her ability to move things forward with clarity.

Mario and Beth also talked about their balanced styles in “Speeding up”  and “Slowing Down” creative conversations - Beth will pump the brakes and ground ideas in reality when the time is right. Feeling that balance between creativity and clarity, speed and thoughtfully slowing things down, is the essence of conscious creativity and conscious collaboration…being comfortable with both opening and closing modes is critical, but collaborating with others who complement your natural approaches is powerful.

Be sure to check out my other co-founder conversations. I discussed building an Integrity Culture with the co-founders of Huddle, Michale Saloio and Stephanie Golik, and investigated prototyping partnerships with Jane Portman and Benedikt Deicke, co-founders of Userlist. (Which Mario and Beth absolutely did, as well!) 

I also sat down with Jennifer Dennard and Dan Pupius, the co-founders of Range to unpack Healthy Conflict in Cofounder relationships. Conflict and collisions will inevitably happen in relationships, so you might as well learn to lean into it!

You may also enjoy my interview with Carolyn Gregoire and Scott Barry Kaufman, the co-authors of the 2015 bestseller, Wired to Create, where we unpack how they managed their working relationship and discuss Paired creativity, which is totally a thing!

And if you really want to dive deep into the idea of being a conscious co-founder, make sure to check out my conversation with my friend Doug Erwin, the Senior Vice President of Entrepreneurial Development at EDAWN, the Economic Development Authority of Western Nevada.

Links, Quotes, Notes, and Resources

Changeist

On Healthy Conflict: https://theconversationfactory.com/podcast/managing-healthy-conflict-co-founder-conversations

Minute 19

Daniel Stillman:

And I'm wondering how, in those early days, the first week you decided to draw a boundary around this is what we're going to do, this is how we're going to work together. What was it like establishing your roles, your boundaries, your relationship in the early days? If you can remember back that far.

Beth Bayouth, COO:

I know, I am trying to remember back, it felt like it was more about... I think at that point we knew who we were as individuals and what our skills were. The boundary of who does what sort of naturally formed.

In the first month, I wrote our business plan obviously with the help of Mario who had already ideated a lot of... Understood who our competitors were, understood all of that. We applied for fiscal sponsorship through community partners. I think that stuff came easy and then it was just so much work. I don't know that we were super intentional about the relationship side of things right away because it was like, let's get the business plan, let's get fiscal sponsorship. As soon as we got fiscal sponsorship, we launched a crowdfunding campaign. That's just a lot of work. We wanted to show bigger institutional funders that we had this backing of individual supporters that really wanted this thing to happen. We raised in the first two months, then we raised 25,000 in a crowdfunding campaign just from friends and family and folks who had experienced the program that this had jumped off from.

Minute 21

Daniel Stillman:

I'm curious, what's your relationship like now? What is it? How do you work on your relationship these days?

Mario Fedelin, CEO:

I mean, I talk to her more than anyone. I talk to Beth more than any other person. If we rewind, there was this vulnerability, maybe there was... I'm going to say when we go back to that first conversation. I was very scared and I felt like I had put myself in a position to where I needed to find a way forward or else I was going to have to eat a lot of shit. I was going to have to go back on my word or I was going to have to tell people because I was just in a really tough place and I had no idea how to move forward. I think you're giving it too much time Beth that conversation, I feel like I asked you in the first 10 to 15 minutes, I was like, would you be interested? One, there was this built-in comfortability.

We've been friends prior. I have a lot of respect for Beth in the work that she had done and where she was at in her career. I knew that I was in safe hands and I trusted that and I had to be really vulnerable of saying, I don't know how to move forward and I really need help.

Minute 27

Daniel Stillman:

Tell me about that Mario. What does it mean to fight well for you?

Mario Fedelin, CEO:

I mean, we disagree on things. We'll get heated and we're both very... We have very strong opinions and...

Beth Bayouth, COO:

Passionate.

Mario Fedelin, CEO:

... We're very passionate about the things we're passionate about and so we'll fight. It's so funny too, sometimes it spills out into in front of our staff members or we'll just go back and forth and oftentimes it's one of us apologizing after we got done like, sorry, did I go too far? Look, we could figure this out. Or we apologize quickly. It's not hard to know when we're like... Also, we know each other's ticks so I know when Beth is really hurt personally or really upset about something and that trigger like I'll stop or we'll close it and then I'll be like, okay, I think I'll apologize. Then, we'll move past it pretty quickly. We're not afraid to confront that. We were arguing about something or we disagreed about something, let's sort it out. It's never personal. [inaudible 00:28:00].

Beth Bayouth, COO:

No, and it's interesting because we had mentioned all the personal side of things and I remember when I first entered the working world, you hear these things from your elders or whatever, don't share too much with your boss. Don't bring your personal life into work. It feels like that stuff isn't very effective. I think lots of times if one of us is overly affected by something that happens at work, it's largely there's something personal happening in our lives that I just can't handle this today. The fact that we're able to talk about all of that very honestly, it just makes for a better working relationship. We try to encourage our entire teams to... We try to make sure that people know that there aren't boundaries like that within our organization because I think we just know it's more effective for everybody to understand each other.

Minute 35

Beth Bayouth, COO:

I also though think to your other part of the question of what has happened to create that space for us, I think it's not just the personal side of things. I think we over the years have also just built trust, working trust in each other. I think we have both displayed that we are doing what we need to do for the other person to feel comfortable. I think along with Mario's vulnerability in the beginning of being able to say where he had shortcomings and moving this thing forward, he also had to really lay his trust in me that I was going to hold his vision dear and work as hard as he needed somebody to, to help make it happen. I know that that took some time.

I had to prove that I was there and I probably had to even take some time to really get there myself too. I think that just over the years we've been able to do that. That's why if I'm freaking out about something, I also know Mario's got it. It's time and time again, we've pulled through and it maybe was the last minute, but I think that we've built that working trust as well.

More about Beth and Mario

About Beth

In her role as Chief Operating Officer, Beth oversees the fundraising, operations, systems, and strategic planning for the organization. Prior to her work with Changeist, Beth received a MBA from Boston University with a focus on social impact. She then moved to Los Angeles to take on Local Control Funding Formula (LCFF) at Los Angeles Unified School District, helping to create new ways for teachers, staff, and stakeholders to better understand the complicated financial policies affecting LAUSD students and communities. Beth is committed to strengthening communities and empowering young people. She is a proud AmeriCorps alumna of City Year Chicago and in July 2017 was honored with City Year’s highest alumni recognition, the Comcast NBCUniversal Leadership Award.

About Mario

Mario spent over a decade in the national service movement with City Year. There developed and oversaw civic leadership programs for youth in three different markets. In 2014 he conceived of, designed, and launched Changeist.

Mario is currently a Board Member and Advisor to multiple community organizations in Los Angeles, a graduate of SCLN’s Leadership LA, recognized by the LA Empowerment Congress as a top 40 under 40 Civic Leader, and serves as a Senior Fellow for USC Marshal School of Business, Brittingham Social Enterprise Lab. In 2019, he was chosen out of thousands of applicants from over 160 countries to be an Obama Foundation Fellow. The Obama Fellowship supports outstanding civic innovators from around the world to amplify the impact of their work and inspire a wave of civic innovation.

Full Transcript

Daniel Stillman:

I am so grateful, Mario, Beth, that you are here to have this conversation about what it means to be a conscious partner in running a business together. I'm so excited you're here. Welcome aboard to the Conversation factory.

Beth Bayouth, COO:

Thanks for having us.

Mario Fedelin, CEO:

Thanks for having us.

Daniel Stillman:

Thank you very much. So Beth, I'm going to start with you. What's the origin story? How did you two come to work together in this big, crazy, topsy-turvy mixed up world? How did you two find each other and start working together?

Beth Bayouth, COO:

Sure. Mario and I met way back in 2005. We both started our careers as AmeriCorps members, happened to be working for the same organization but in different cities. I was in Chicago, he was in Philly. We both became staff members and were leading Saturday civic leadership development programs for middle school and high school youth. The organization brought us together. There was about a team of 10 of us nationwide who were all working on these programs and they wanted us to think through really what the overall learning outcomes were, how we could make sure that we were learning from each other and making each of those programs in the cities as best as they could be. We met then and that's sort of where our friendship and professional relationship started.

Daniel Stillman:

2005?

Mario Fedelin, CEO:

I also [inaudible 00:01:42] those times.

Beth Bayouth, COO:

You were young.

Mario Fedelin, CEO:

I was like this younger kid too who totally undereducated. I feel like I was a little bit in over my head in Philadelphia, how I landed there. At least that's how I felt. Beth, along with a couple other folks who had their degrees and they had been working on these programs, I was kind of trying to figure out how to navigate those dynamics of someone who's undereducated and someone who's educated and trying to do something together. It was an interesting start to the relationship.

Daniel Stillman:

So Mario, what brought you to AmeriCorps?

Mario Fedelin, CEO:

I found, again, it was a little bit of an accident. I guess the way that it starts is I grew up on the east side of San Jose. Had an opportunity for... And that's in the California suburb some people, it's called the South Bay. I had a teacher who, my brother had some challenges in high school, but everyone really liked him. As I came into that high school, people were like, oh, that's what's-his-name's little brother and so I think people kind of wrapped their arms around me a little bit. I got sent to a camp. Camp happened [inaudible 00:02:56] Santa Cruz Mountains and I had this really amazing camp counselor who was a brown kid that looked like me, but was very different than the other brown kids I ever met. Now, his name was John and we just had a blast for a week and that was a week in the Santa Cruz Mountains where we talked about, at that point they called the tolerance.

It was really diversity and racial justice and all those sorts of things. Anyways, fast forward, I graduated from high school, I had this adventure out, not going to college. When I came back to San Jose when I was 20 years old, I was transferring a expensive coffee shop chain. I was transferring from San Diego up into San Jose. Randomly as I was walking down, one of the alleyways [inaudible 00:03:42] San Antonio in downtown San Jose. I saw these random people walking that had these jackets on, these yellow jackets and it instantly, it was like, oh, my homeboy John used to work for that company. Maybe I could work with kids. That seems pretty cool because I didn't really have a plan. I walked into that recruiter's office and just so happens that they were hiring AmeriCorps members and at that moment, so it was a real quick start turnaround and I interviewed and I got placed on this diverse team working on civic leadership programs on Saturdays in my neighborhood. That's how it all kind of happened.

Daniel Stillman:

That's amazing. John's jacket was like...

Mario Fedelin, CEO:

The jacket, the symbol. It was a symbol.

Daniel Stillman:

That's amazing. The power of a symbol, the power of a properly chosen color.

Mario Fedelin, CEO:

It was less about... The color wasn't the indicator, it was a personal relationship that flagged it. I think that's the important thing to remember is we have our brands and our powerful brand narratives [inaudible 00:04:45] it would've never had the same meaning if John wasn't compassionate and the way that we exchanged ideas together and made me feel like I was a whole person in those moments. I mean, I had never spoken to him since and now it's been... We're looking at more than 27... 25 years later. I can still tell you his name. It's the person.

Daniel Stillman:

That's amazing. That connection. Beth, what brought you to AmeriCorps?

Mario Fedelin, CEO:

That's the power of youth workers.

Daniel Stillman:

Yeah.

Mario Fedelin, CEO:

That's the power of youth workers and the power of connection to people.

Daniel Stillman:

Yeah. Yeah. Sorry for cutting off there. But yeah Beth, I'm curious, what was your turning to AmeriCorps as well?

Beth Bayouth, COO:

Very different. I kind of had a very traditional path. I was supposed to go to college after high school. I did that in a pretty misguided way. I had no idea what I was doing there. What I wanted to do. Ended up majoring in business because it was practical. That was the only thing I could really think about getting out of the college experience other than I was a leader in clubs and the social aspect and living on my own and that kind of thing. When I graduated I didn't see myself doing anything business related. I didn't understand what I could really do with that degree that was going to appeal to my passions and what I had been doing thus far with volunteer work and everything. I had a friend who'd done an AmeriCorps program and was like, I think you'd really like this. I thought, well that sounds good. I've always worked with young people.

I was planning on moving to Chicago and it was a really good opportunity. It lined up with my timeline. I got in there and I was working in Chicago public schools and my whole family are public school teachers and I think I had been fighting whether that was supposed to be my reality. I was like, well this will be a good test run. I'm in the schools every day getting to see what it's like. Very quickly decided that that was... Definitely, I was right. That was not going to be my path, but I loved working with young people outside of school. I loved having that... The real relationships that you could build and thinking about how you supplement the school day and the academics with things that young people are really curious about.

Daniel Stillman:

That makes a lot of sense. I can really understand loving the content of education, but changing the context is really beautiful. 2005 to 2014, how did you get the band back together? What was the spark getting... I mean, because Changeist was 2014, but although I imagine it may have started a little bit earlier in your brain, Mario. Do you want to talk a little bit about the origin story of Changeist and then how you two wound up together and in the roles that you have in the company?

Mario Fedelin, CEO:

Yeah, so I was still working for that agency. That same organization, it's called City Year, but we had... I started in 2003, four we met in 2005. I became one of the guys who was working on the Saturday leadership programs for high school students. Beth and I worked even closer when we were working on the high school program because she actually had me come out to Chicago and work with her and a group of practitioners to thinking about starting a Chicago-based high school program. The organization had an opening in Los Angeles and so they brought me out in 2007 to launch their civic leadership programs down here and so that's how I landed in LA. It was really just as I was hitting the 10-year mark at that agency, I was tired.

I think I had a really tough year with just a little bit of burnout. I ended up having to close those civic leadership programs in 2011 because the organization wanted to focus, which ultimately was the right decision for that organization, but I had to help close down those nationwide and that all of our work that we had done together felt like it just got put on the shelf and benched when it was really the first program that agency had really put into standardization, which Beth and I were a part of. It felt like a little bit of waste, but I ended up retooling and just going straight into the education space with the organization and working on school campuses with principals. Then, I just wasn't that into it. I was organizing on school campus. That was the fun part where I was trying to raise money through school budgets and it wasn't exciting.

Looking at math scores and English scores for individuals just wasn't really what I had ever signed up for. Again, because I didn't go to college, I had these really big holes and gaps in knowledge and practice. Through those years when I was in LA I was volunteering for other agencies and boards and trying to develop my acumen. One of the organizations that I was working in was a program in South Central and mixed with this kind of itchiness to move on to something new and being with my partner watching this culminating event through one of the organizations that I volunteered for really part-time on the operational side, I just was like, you know what? I could do that. I could do that on my own and I could probably do it very differently and do something bigger. I just had that kind of itch.

It was that moment, at that culminating event on a college campus and then me and my partner went to go watch a movie and we got on one of the trains and I was seeing these kind of rec centers off the train that were beautifully kind of... Had art and graffiti on it. I was just like, I could do something bigger and different than what I'm doing now. Had some mimosas and I started Spouting off what I wanted to do because I had recently also had a bunch of young people come back. After those program closed, about three years ahead of that they started coming back in their senior years and saying, "Hey Mario, I'm running this thing for my school. Do you have any tips on how I could run this service project?" There was about three or four of them that came back that year also so now you have my own discount or my kind of burnout with these old students that were coming back for tooling up. And so they needed me for something and then me figuring out what the self-discovery looks like and seeing a gap in the youth workspace and my life partner when we're having a conversation, I was kind of throwing out this big picture idea of consulting for kids. I think it was the original version of it. She was like, "Yeah, you should do that." I was like, "I should do that."

Daniel Stillman:

That does sound like a mimosa. Talking a little bit.

Mario Fedelin, CEO:

Yeah, it was definitely mimosa. Got all very excited about it.

Daniel Stillman:

But supportive, which is really good.

Mario Fedelin, CEO:

Yeah, right. Then she told me, she was like, and we can live with my mom if you want, we could figure this out together. I was like yeah, we should do that. Then, on Monday it still sounded like a good idea. That Monday I told my boss at that point and I was like, I'm going to leave here. I'm going to give you some time. I can't leave now, but this is going to be my last round and I want to start a non-profit. To their credit, that agency City Year and the people there were just like, hell yeah, we'll help you do it however we can help.

Then, I started down the journey of figuring out, well what kind of team can I put together? And I got all of my favorite people that I'd worked with in the past in LA together and started taking one day a week off at City Year to think about big picture stuff and think about what this program would be. And I started these meetings with folks and just started to build. And Beth wasn't part of that yet, but that was the early days of 2013 I'm assuming that I started putting the stuff together.

Daniel Stillman:

That's amazing. And so Beth, what was your experience like coming into Changeist? What did things look like when you stepped in?

Beth Bayouth, COO:

Yeah, so after leaving City Year as a staff member, I took a couple years and then I went back to school and ended up getting a master's in business so business was the right choice, happenstance. That experience brought me out to... That was in Boston and I ended up doing a fellowship that brought me out to LA for a summer. Working with LA Unified and... First, it started my love for Los Angeles and I was really excited to try and come back once I finished my master's and I was able to. In summer of 2011 I moved out to LA permanently and was continuing the project that I got that fellowship with. I was working with Los Angeles Unified School District on what's now their local control funding formula and was working in the district office. I did that for a couple of years and just felt a bit disconnected.

I was really missing the vibrancy of that feeling that you would get with organizations like City Year and working on something. I definitely am a behind the scenes type of worker, but also I like being able to be close to the young people that we engage with. I was looking for something new. Mario got sort of stuck where he was at, I would say, is that fair?

Mario Fedelin, CEO:

Very Fair.

Beth Bayouth, COO:

And a lot of folks... We had people in common, we had friends in common and it got into Mario's ear that I was looking for something new. He was like, can we go get some coffee? I think it was like 45 minutes into reconnecting and he was like, you want to help me start this small nonprofit? And I was like, yeah, let's do this, let's do this again. I took a few weeks and talked to my husband about it and thankfully he's in tech startups, so was kind of like, yeah, this is your turn to do a startup. Let's see how it goes. Talked to a couple of our mutual friends and was just like, yeah, Mario's been working on this. I've been working on it with him. This is legit.

Mario Fedelin, CEO:

I mean, also she really was more like, "Sure, that sounds cool." I don't know if it was as optimistic conversation because that was like, "Oh shit, is she really going to do this?" And then she goes back to all of our friends. I also hear, and so she's talking to everyone to make sure I wasn't full of crap and make sure that we actually had some foundation of thought put into it. Then she committed and she's like, I'll do it. I'm in until October. It's like, I could do this until October. This was a meeting in what? Was it in April? We had this conversation?

Beth Bayouth, COO:

Yeah, March or April.

Mario Fedelin, CEO:

Maybe March.

Beth Bayouth, COO:

I think I said, I'll give you six months and see if we can raise some money.

Mario Fedelin, CEO:

I was like, all right. Technically, Beth was the first person to work on Changeist full-time.

Daniel Stillman:

Wow.

Mario Fedelin, CEO:

Free. I mean, also what we got... Where we had gotten was we had worked with this group. I had called them our architects and they had really helped put shape to this thing. At the point when I was in probably February, I thought that we had some pretty cool stuff lined up. This seems like we could do this. I could actually right now go get some young people, we could launch this. But my job was ending at City Year. I had no personal money, I was crap at saving money personally. We weren't able to get that together and I had no way to raise money because we had no 501 C3 and no financial back, no kind of infrastructure. That was the stump point. This is where we like to say that... People were in my ear about Beth being on a job hunt, but also her LinkedIn spammed me. I was like, oh Beth. I got this random email from LinkedIn and I was like, oh yeah. I was like, of course. It's a sign because someone just said Beth's name and now her LinkedIn is... Said add me to your network. That's kind of how we reconnected.

Daniel Stillman:

This is the moment inside the moment and I want to zoom in because this is the first conversation. There's coffee and there's an agreement to a limited experiment to see where things could go. And I'm wondering how, in those early days, the first week you decided to draw a boundary around this is what we're going to do, this is how we're going to work together. What was it like establishing your roles, your boundaries, your relationship in the early days? If you can remember back that far.

Beth Bayouth, COO:

I know, I am trying to remember back, it felt like it was more about... I think at that point we knew who we were as individuals and what our skills were. The boundary of who does what sort of naturally formed.

In the first month, I wrote our business plan obviously with the help of Mario who had already ideated a lot of... Understood who our competitors were, understood all of that. We applied for fiscal sponsorship through community partners. I think that stuff came easy and then it was just so much work. I don't know that we were super intentional about the relationship side of things right away because it was like, let's get the business plan, let's get fiscal sponsorship. As soon as we got fiscal sponsorship, we launched a crowdfunding campaign. That's just a lot of work. We wanted to show bigger institutional funders that we had this backing of individual supporters that really wanted this thing to happen. We raised in the first two months, then we raised 25,000 in a crowdfunding campaign just from friends and family and folks who had experienced the program that this had jumped off from.

Daniel Stillman:

I'm curious, what's your relationship like now? What is it? How do you work on your relationship these days?

Mario Fedelin, CEO:

I mean, I talk to her more than anyone. I talk to Beth more than any other person. If we rewind, there was this vulnerability, maybe there was... I'm going to say when we go back to that first conversation. I was very scared and I felt like I had put myself in a position to where I needed to find a way forward or else I was going to have to eat a lot of shit. I was going to have to go back on my word or I was going to have to tell people because I was just in a really tough place and I had no idea how to move forward. I think you're giving it too much time Beth that conversation, I feel like I asked you in the first 10 to 15 minutes, I was like, would you be interested? One, there was this built in comfortability.

We've been friends prior. I have a lot of respect for Beth in the work that she had done and where she was at in her career. I knew that I was in safe hand and I trusted that and I had to be really vulnerable of saying, I don't know how to move forward and I really need help. I think when Beth says that we knew who we were, it was like I knew what I was really good at and I knew that Beth was in a much different place and there was overlap in some of that stuff. In a lot of ways I didn't hire some... I didn't hire or we didn't sign onto something where we were both going to be having the same type of skill sets. It was like Beth is... Beth is a little shark and I needed someone to help push the ideas forward because I was the one who was throwing everything out on the wall and Beth was able to ground it and plant it. That is still the case in our relationships is I'm the one that comes with the ridiculous idea and Beth's like, that's dumb. And I'm like, you're right. That is dumb.

Or I give the idea and she's like, yeah, that's a good one. Then [inaudible 00:23:11] gives it life and brings it to life. We talk all the time. I mean, we've been through a lot together in the last nine years. It's like family deaths, a pandemic, to emotional [inaudible 00:23:27] relationships, childbirths. We have two kids that were born including one that was the very first four months. Let me tell you this story. I think we're in office [inaudible 00:23:38] in the first three months of this happening. I think we just got our money, maybe. So we're going to a presentation or something [inaudible 00:23:47] and she was like, I have something to tell you. I'm pregnant. I'm like, okay. And I'm like, oh man, is she going to walk away? Then, it was fine because we were like, yes, we're building this to be a family thing, so of course we'll figure this all out.

Then, the real pain came in is when six months hit. It was October, November and we still had no other money except for that 25,000. I'm like, how did I walk this friend into a shit storm who is about to have a baby and we have no financial security and this is going to fall apart. I was really scared. I remember sitting on my bed crying to my... Actually, physically sitting there crying on the bed after having a conversation with Beth where Beth was not upset about anything at all, but I was just so scared that I wouldn't be able to get us on payroll. She wouldn't be able to have things she needs to support her family as she gets started on that journey. There was no prospects, but Beth was steady. She was like, it's fine, we're going to get through this. Then, a month later we had $200,000 show up and a bunch of things that we had talked about with friends out and then just all just showed up and came together.

Daniel Stillman:

I'm sitting here and I'm pulling these threads together in my mind from an appreciative inquiry lens. What I'm hearing that is alive and powerfully functional in the way you two relate. One is just a human foundation, having known each other, having worked together there is the ability to be vulnerable with each other, which doesn't come... Is nontrivial. That doesn't come for free. That's something that's earned. The other thing that I'm hearing, the fourth thing is that you both have a sense of who you are, you know what you are good at, and you also know and respect what the other person is good at. There's that space to have the other person step in and the two things that I'm hearing, this is something in the design world, we talk about opening and closing or divergent and convergent. Sometimes people are divergers and convergers. Mario, you're a really good diverger, and Beth, you're a really great converger. The fact that you have, if both of you were divergers, it would be really, really hard. You need a closer, everybody needs a closer. Then, underneath all of that seems to be a very strong undercurrent of respect, which is all really powerful. Is there anything else that you feel like is alive in your relationship that I missed or that we haven't talked about yet?

Mario Fedelin, CEO:

We fight really well.

Daniel Stillman:

Tell me about that Mario. What does it mean to fight well for you?

Mario Fedelin, CEO:

I mean, we disagree on things. We'll get heated and we're both very... We have very strong opinions and...

Beth Bayouth, COO:

Passionate.

Mario Fedelin, CEO:

... We're very passionate about the things we're passionate about and so we'll fight. It's so funny too, sometimes it spills out into in front of our staff members or we'll just go back and forth and oftentimes it's one of us apologizing after we got done like, sorry, did I go too far? Look, we could figure this out. Or we apologize quickly. It's not hard to know when we're like... Also, we know each other's ticks so I know when Beth is really hurt personally or really upset about something and that trigger like I'll stop or we'll close it and then I'll be like, okay, I think I'll apologize. Then, we'll move past it pretty quickly. We're not afraid to confront that. We were arguing about something or we disagreed about something, let's sort it out. It's never personal. [inaudible 00:28:00].

Beth Bayouth, COO:

No, and it's interesting because we had mentioned all the personal side of things and I remember when I first entered the working world, you hear these things from your elders or whatever, don't share too much with your boss. Don't bring your personal life into work. It feels like that stuff isn't very effective. I think lots of times if one of us is overly affected by something that happens at work, it's largely there's something personal happening in our lives that I just can't handle this today. The fact that we're able to talk about all of that very honestly, it just makes for a better working relationship. We try to encourage our entire teams to... We try to make sure that people know that there aren't boundaries like that within our organization because I think we just know it's more effective for everybody to understand each other.

Daniel Stillman:

That's really interesting. In a way, so there's two things I'm hearing. Mario fighting well means recognizing when you've crossed a line, knowing how you're affecting the other person, apologizing quickly if need be. I think there's another piece of this, Beth, which is knowing that if you are getting under each other's skin, it's because there might be... There's often something else outside of the work sphere that is affecting things. Because you're close, you tend to know about that or that you can ask about that. We're not going to be watching this so they're both nodding right now in sync even though they're in two different places, which is amazing.

Beth Bayouth, COO:

Yeah. I can recognize, oh I am feeling really strongly about this, but you know what, it's because my daughter's sick or it's been stressful at home or something and I can take a step back and be like, Mario, let's... Can we just table this conversation? And it's welcomed. It's understood.

Daniel Stillman:

Yeah.

Mario Fedelin, CEO:

I also point out too, I think it's... We've rarely both been in a place of instability at the same time or we both handle things... Whenever I'm like, we're not going to finish in the black and I'm freaking out over something, there's always this sense of calm. Whether it's intentional, or unintentional from Beth to be like, look, there's an out here. And vice versa. Beth is on the verge of freaking out about something that's happening. I'm like, I'm not that worried about it. Look, we're going to be fine. We've been in lock sync. I think that's been kind of one of the things where it's been... Whenever it all feels like it's falling apart, Beth never believes it is. That has helped us get through this. That's really hard to find, I think in a collaborator.

Beth Bayouth, COO:

Yeah, we're definitely able to balance each other.

Daniel Stillman:

I've heard...

Mario Fedelin, CEO:

How many times has this organization fall... How many times has this organization felt like it was about to fall apart completely? And one of us is just like, look, we'll get through this.

Daniel Stillman:

So the key is both of you not fall apart at the same time and somehow it just doesn't happen?

Beth Bayouth, COO:

It has not happened yet.

Mario Fedelin, CEO:

And we've gone through a global pandemic, so who knows what the threshold's going to be. If it wasn't for Beth, this would never have happened. There's no way.

Beth Bayouth, COO:

I mean, you had the idea.

Mario Fedelin, CEO:

Yeah, but it was nothing without having some grounding and some [inaudible 00:32:17] and that came through what you brought to the table. And I don't know that... I don't know that I would've had a different collaborator. I don't know that a different collaborator would've helped me weather all this stuff.

Daniel Stillman:

Beth, good job on taking a compliment. I know for myself it's a skill that I under-utilize. I'm much better at batting them away.

Beth Bayouth, COO:

Yeah, it's hard, but I'm working on it.

Daniel Stillman:

It's a thing. Well, speaking of working on things, what do you feel are some of the challenging parts of your relationship that you've had to work through? What comes to your mind when you say Hmm Beth?

Beth Bayouth, COO:

It doesn't ever feel challenging.

Daniel Stillman:

Yeah.

Beth Bayouth, COO:

I'm sure there are. I'm sure I'm just missing something here, but nothing ever feels like we can't talk about or we really overstepped.

Daniel Stillman:

Yeah. What do you feel... So there's this phrase that I've heard some folks use, which is that everything is workable. There's this container here in your relationship where things can be discussed. I guess what I'm curious about is what has enabled you two to create a space where you feel safe to work through what you need to work through?

Mario Fedelin, CEO:

History. I don't know, context.

Daniel Stillman:

History and Context.

Mario Fedelin, CEO:

Friendship.

Our partners know each other. Our kids play together. How I live down the street from her for a year in that same complex. I think maybe if I'm picking at what's hard, at least... There hasn't been a problem yet, but I do wonder what does our future look like, and how long can we do this for? And what happens when one of us is ready to walk away? Being able to allow the other person grace to do that. I think that's something I'm thinking about in terms of our relationship is like, it's going to be tough because life is changing, it's almost going to be a decade. We got to be able to allow ourselves to grow. Although, I keep trying to pull Beth into other collaborations. I want to start another business with her. I'm like, how about we do this? How about we do that?

Daniel Stillman:

That's interesting.

Beth Bayouth, COO:

Again, I slow it down.

Mario Fedelin, CEO:

That's something to think about. How does it end? Beth is not my life partner, so we're not married. That means that this is... At one point, this relationship is going to come to an end because I can't imagine us running Changeist forever together. That has to be a concern or a thoughtful because we have so much mutual respect for one another and a deep friendship. I can imagine how it would be much harder to say goodbye or to say I got to go. I mean we, I don't know. Beth's probably like, "Nah, it's cool." She'll tell me. When do we say now it's time and not have resentment for the other person walking away?

Beth Bayouth, COO:

Yeah, I agree with that. I also though think to your other part of the question of what has happened to create that space for us, I think it's not just the personal side of things. I think we over the years have also just built trust, working trust in each other. I think we have both displayed that we are doing what we need to do for the other person to feel comfortable. I think along with Mario's vulnerability in the beginning of being able to say where he had shortcomings and moving this thing forward, he also had to really lay his trust in me that I was going to hold his vision dear and work as hard as he needed somebody to, to help make it happen. I know that that took some time.

I had to prove that I was there and I probably had to even take some time to really get there myself too. I think that just over the years we've been able to do that. That's why if I'm freaking out about something, I also know Mario's got it. It's time and time again, we've pulled through and it maybe was the last minute, but I think that we've built that working trust as well.

Daniel Stillman:

If you were talking to young entrepreneurs at the beginning of their journey now, what kind of advice would you be offering them to build the kind of relationship, the kind of longevity that you two have had?

Mario Fedelin, CEO:

I think with entrepreneurs, at least the stuff I've heard or read is always [inaudible 00:37:59] the only ship that sinks the partnership. I don't know if you've heard that, is don't do things together with another person.

Daniel Stillman:

I have never heard that.

Mario Fedelin, CEO:

I don't know if maybe I'm being the wrong things... There is a school of thought that's like, you go alone and then bring people in. I would take the advice of someone... The founder that City Year told me it was just find a partner. Someone that could vouch for you and someone you trust and someone that will always say that you're doing well to another person when they ask about you. So that you could weather some of the tough storms through the entrepreneurial journey. Because it's tough. Again, all the hard stuff is always about personal fear. I feel like all the things that we've ever had... Weather that have been seemingly dire or real consequential were personal ego or self insecurity and of being at the table or knowing what to say. Everything else is learnable and manageable. Being able to have another person help you, whether that stuff personally, I think that's made this thing float. Finding that other person, and it can't just be anyone, it's got to be someone that has a different skill set, similar values that's willing to go through it with you.

Beth Bayouth, COO:

And you have to be able to admit that you have to have enough trust in them that you can admit when you don't know what you're doing or you're wrong or you're scared because otherwise it's not a relationship worth having.

Daniel Stillman:

Well and it's also to what you were just saying, Mario, if these things are learnable, if we aren't willing to say that we don't know them, it's hard to learn them.

Mario Fedelin, CEO:

Yeah, [inaudible 00:40:01].

Daniel Stillman:

Uh oh, did I freeze or did Mario freeze?

Beth Bayouth, COO:

Mario froze.

Mario Fedelin, CEO:

Oh no, I froze.

Daniel Stillman:

Oh, you're back.

Mario Fedelin, CEO:

Oh no, I froze.

Daniel Stillman:

Just say whatever... Just say whatever you said exactly the same way.

Mario Fedelin, CEO:

I was just saying the myth... I think the myth around the entrepreneur side of stuff is like, it's not the technical stuff that's hard. That's the easy part. You could always figure out the technical stuff. There's always someone you could bring in. There's always someone to talk to, to help you through this thing, this finance report or raising money or building this. That stuff is easy. You find anyone could do that. The hard part I think is having the strength to endure and that's where a friend comes in.

Daniel Stillman:

So we're amazingly getting very close to the end of our time. Beth, what haven't I asked you about having a powerful relationship as two folks running the core of a business? What haven't we talked about that we should have talked about?

Beth Bayouth, COO:

Sometimes, I wonder how does our partnership come across to the rest of our team?

Do they think we have each other's backs, even if we're totally wrong? That kind of thing. I'm curious, and I don't think we've ever really talked to anybody on our team about it, but I wonder how it affects everybody as a whole. We've never explored it. I don't know how... We'd probably have to do some sort of external consulting to find out, but I would like to think that it's helpful. I would like to think we're modeling how we want everybody to operate or how they support their own teammates, but we don't know.

Daniel Stillman:

That's a really interesting question. And hearing the two of you talk about the quality of fighting well and I was like, oh, I wonder if that trickles down. I'm curious about that too. And that would be really interesting to learn about for sure.

Mario Fedelin, CEO:

Especially, because we're the bosses, so you're the boss in those spaces. Then, when we both start going at it, I imagine people are like, oh, this is awkward.

Beth Bayouth, COO:

I mean, let's be fair, we're not fighting, we're just disagreeing.

Daniel Stillman:

Yeah, yeah.

Beth Bayouth, COO:

But we're both very blunt. When we're delivering a disagreement to each other, we know we don't have to sugarcoat it. If other people are present, maybe that feels uncomfortable. I've never received that feedback, but I can imagine that that could be.

Mario Fedelin, CEO:

I could imagine.

Daniel Stillman:

Well, for the two of you, with the folks that you manage, do you feel like you conduct yourself in a similar way that the quality of your conversations are similar?

Beth Bayouth, COO:

I think we both are very clear that we are open for feedback and discussion and really want to understand how people are feeling, but there's still the dynamic of supervisor and employee, especially with folks who might be newly entering a career and really figuring out what can they really do and say, I think, you see different levels of what that looks like with other relationships.

Daniel Stillman:

Yeah. And it seems like the two of you really relate to each other as equals, which is really powerful.

Mario Fedelin, CEO:

Yeah.

Daniel Stillman:

Well, I really appreciate you two taking the time to be so reflective and vulnerable and real. These are such wonderful qualities to notice in a high quality partnership. I'm glad that you two have been able to create that for each other and especially in service of the mission that you two are serving. That's awesome.

Mario Fedelin, CEO:

I couldn't ask for a better partner.

Beth Bayouth, COO:

Same.

Daniel Stillman:

Well, that seems like a great place to call scene.

Managing Healthy Conflict: Co-founder Conversations

In this conversation I talk with Jennifer Dennard and Dan Pupius, the co-founders of Range, software that helps teams be more connected, focused, and productive no matter where they’re working. Global teams at Twitter, New Relic, CircleCI, and more keep their teams in sync and connected with Range.

Jen is the co-founder and COO. Prior to founding Range, Jen led Medium’s organizational development team. Jen has partnered and consulted with startups and multinational corporations on empowering autonomous and distributed teamwork. She lives in Colorado with her two cats and husband.

Dan is co-founder and CEO of Range. Prior to Range, Dan was Head of Engineering at the publishing platform Medium. And before that he was a Staff Software engineer at Google, where he worked on Gmail, Google+, and a variety of frontend infrastructure.

He has an MA in Industrial Design from Sheffield Hallam University and a BSc in Artificial Intelligence from the University of Manchester. In past lives he raced snowboards, jumped out of planes, and lived in the jungle.

This is a fairly meta conversation (in the old sense of the word!) since we talked about how Dan and Jen structure their relationship and how they built their company…which is a company that builds software that structures relationships - specifically, effective teams.

As Dan outlines, “Human behavior requires structure to facilitate it…in an organization, software provides a lot of architecture, which shapes our behavior, but we're (often) not intentional about that software. The whole theory of Range was… how can we build software that acts as architecture that shapes the behaviors that we believe to be present in effective teams?”

My book Good Talk is built around the idea of a Conversation OS, or Operating System. 

One element of the Conversation Operating System is error and repair. As Jen says in the opening quote, conflict and collisions will inevitably happen in relationships.

Dan suggests that “if you have productive conflict or if you encourage productive conflict, there will be times when you step over the boundary and it's what you do then that is the important thing, in how you recover.” In other words, how you repair the error or breach in the relationship is often more important than the error itself.

Many folks shy away from conflict, or hope it never happens. Planning for it and knowing it will happen is a fundamentally different stance, a more effective Error and Repair Operating System.

I also love the “reasonable person principle” that Jen and Dan use in their relationship, as long as it never slides into gaslighting.

We unpack a lot more great stuff, from uninstalling Holacracy at Medium to the importance of being journey-focused in entrepreneurship relationships, and the power of crafting explicit processes ahead of needing to use them.

Dan and Jen are also big believers, like me, in the power of the “check-in''. For example, in my men’s group we share in 30 seconds how we're doing emotionally and physically at the start of every group. At Range, it can be as simple as a “green, yellow, red” check-in or as deep as going straight to the question “how are you…really?” 

They suggest that baking human connection into each and every meeting is much much more effective than trying to isolate connection into one “vibes” meeting.

As with many of my co-founder conversations, there is a common thread of clear roles along with an awareness of and respect for the Venn diagram of skills between the co-founders.

Another common thread, as Dan says at the end of our conversation: looking after yourself and attending to yourself is key, because “if you're not in a good state, you can't be a good teammate and you definitely can't be a good leader.”

Be sure to check out my other co-founder conversations. I discussed building an Integrity Culture with the co-founders of Huddle, Michale Saloio and Stephanie Golik, and investigated prototyping partnerships with Jane Portman and Benedikt Deicke, co-founders of Userlist. 

You may also enjoy my interview with Carolyn Gregoire and Scott Barry Kaufman, the co-authors of the 2015 bestseller, Wired to Create, where we unpack how they managed their working relationship. Paired creativity is a thing!

And if you really want to dive deep into the idea of being a conscious co-founder, make sure to check out my conversation with my friend Doug Erwin, the Senior Vice President of Entrepreneurial Development at EDAWN, the Economic Development Authority of Western Nevada.

Links, Quotes, Notes, and Resources

Range

Lawrence Lessig’s Pathetic Dot theory

Daniel Coyle’s Belonging Cues: Belonging cues are non-verbal signals that humans use to create safe connections in groups. The three basic qualities of belonging cues are 1) the energy invested in the exchange, 2) valuing individuals, and 3) signaling that the relationship will sustain in the future.

Kegan’s Levels, specifically, Stage 4 — Self-Authoring mind

Lead Time Chats

Minute 8

Jennifer Dennard:

Part of why we chose to do a company was thinking about the journey and not the outcome, so startups are very unlikely to succeed, statistically. And so I think it can be similar when thinking about a conversation. Instead of going into it saying like, "This is what I want this person to say or do at the end of it," it's more like, "How do I want to feel during it?" And like, "How do I want the experience to be for both people?" And I think that's kind of how we think about conversations, but also more broadly, as a company, like, "What's the experience? Cool. Are we still having fun? Are we enjoying the adventure?" Certainly there are downs amongst that, but I think part of what has made us successful as a founding duo is that we are in it for the journey versus any specific moment or specific outcome, which I think can be really hard to then deal with the journey, which is quite long.

Minute 9

Daniel Stillman:

Well, so now we get into the point of the story where the beginning can seem organic and emergent, and then at some point, you do start to have that question of, as you said, Jen, values versus tactics alignment, right? And how are we going to do things around here, right? Building the culture and the process of how we're going to do things. How do you feel like you have managed that conversation of aligning on how to align?

Dan Pupius:

Yeah, to some extent, this aligns with the whole purpose of Range in the first place, which is that I think human behavior requires structure to facilitate it. Part of the inspiration for Range is from Lawrence Lessig's pathetic dot theory, that human behavior is manipulated by the forces of laws, markets, norms, and architecture. And in an organization, software provides a lot of architecture, which shapes our behavior, but we're not intentional about that software. So the whole theory of Range was about, how can we build software that acts as architecture that shapes the behaviors that we believe to be present in effective teams? So we kind of like thought about the processes ahead of the problems, so what's our cadence of work? How do we communicate? How do we run meetings? How do we talk about things? And just really thinking about the architecture of which we set things up.

And I think we're not super dogmatic and we're flexible, but I think it's something to fall back on.

Minute 17

Daniel Stillman:

I've heard this before, that some clarity around roles and division of labor is really helpful. Otherwise, there can be unclarity, for lack of a better word, but it seems like the other side to the coin is also true, which is flexibility to pass things back and forth and to shift and alter who's doing what is also really powerful. I'm curious how you navigate that conversation.

Dan Pupius:

Well, I think, we have a Venn diagram, so there's the stuff that's clearly mine and clearly Jen's, and then the middle bit is the messy bit. And luckily, there's not too much there, though that's probably the most critical part of the business for the last 18 months or so, so lots of back and forth on marketing and sales, for example, but it means that we still have these areas, where's it's just very clearly our areas of expertise, where we get to have mastery and complete autonomy. And then it's really the messy middle where we go back and forth. I think if it was all messy, that would be really difficult, or if only one of us had areas of specialization, that would be really difficult as well and probably really disempowering.

Jennifer Dennard:

Yeah. A lot of the decision of who takes something usually relates to bandwidth, and that's both time available but also energy. Sometimes Dan or I will take something just because other person's like, "Oh, I cannot keep doing that," or I don't quite have capacity. And I think that's maybe another thing that we haven't talked about yet in this conversation, is we have invested in through process and tried to cultivate a sense of, I think, safety and belonging on our calls, on how we work together. And that allows me, for instance, to say something like, "I just had hip surgery two weeks ago," and to be like, "Hey, my pain level before or after that is really high. I'm just not able to be what you might consider a normal capacity for me." And Dan [inaudible 00:19:21] hear that and, at least my experience of it, to not feel blamed at all, just to be like, "This is a fact about the bandwidth that we have as a collective system." And I think that allows that kind of handing off of responsibilities in a way that doesn't feel contentious.

Minute 27

Dan Pupius:

But, yeah, if I'm sleep deprived, I will be a bit sharp and I will step over the boundary of what is safe conflict, right? And that could be a catastrophic event if we didn't have that foundation. So I think that's kind of what's interesting, is that if you have productive conflict or if you encourage productive conflict, there will be times when you step over the boundary and it's what you do then that is the important thing in how you recover.

Daniel Stillman:

Jen, what do you do when Dan gets a little sharp?

Jennifer Dennard:

Usually, I pause. Like Dan kind of knows as well, I'll be like... I look away and I'll be like, "Okay, let me..." And then I usually try to pull out what it is underneath, like what is he trying to say or what's the best interpretation? I think something Dan maybe came up with at Medium or we started using there was the reasonable person principle and the idea that whatever the person's sharing, there's a reasonable explanation. And so I think I probably... Took me some time, probably... So Dan at Medium was more my mentor, I would say, and so to come into a co-founding, peer relationship, as a woman who's also younger, I think it took me probably the first few years to really step more into like, "We are peers." And I distinctly remember Dan going out on a very abbreviated paternity leave, unfortunately, at the start of the pandemic. And I was like, "Oh, Dan doesn't know what he is doing either. He just comes up with an answer when I ask, and I can do that."

And I think feeling like a peer in those conversations, to the point we were talking about earlier with power dynamics and stuff, really changes how sharpness lands. It doesn't feel personal. It feels like Dan didn't get enough sleep last night. I think, if it ever starts to feel personal, I also feel comfortable being like, "I'm going to step away from this call. I don't think we're being productive." And we've done that here and there and instead come back together. And I think knowing that, just like any relationship that when you have conflict, even if it does go into a space you're not comfortable, that you have the ability to repair, in my mind, matters because you're never... Whether it's your founding partner or a friend or a spouse, you're never going to not have conflict, unfortunately. And so [inaudible 00:29:24] that you can, typically make it productive, and then when it's not, that you can repair and talk through whatever underlying issue, that feels important to me. And I think we have that really shared understanding

More about Jennifer and Dan

About Jennifer

Jennifer Dennard is the Founder and COO of workplace collaboration software company, Range. Global teams at Twitter, New Relic, CircleCI, and more keep their teams in sync and connected with Range. Prior to founding Range, Jen led Medium’s organizational development team. Jen has partnered and consulted with startups and multinational corporations on empowering autonomous and distributed teamwork. She lives in Colorado with her two cats and husband.

About Dan

I'm Dan, an English software engineer and entrepreneur who lives and works in San Francisco.

I am co-founder and CEO of Range, where we believe that healthy companies aren’t simply better places to work, but do better work. We build software that helps teams be more connected, focused, and productive no matter where they’re working.

Prior to Range, I was Head of Engineering at the publishing platform Medium. And before that a Staff Software engineer at Google, where I worked on Gmail, Google+, and a variety of frontend infrastructure.

I have MA in Industrial Design from Sheffield Hallam University and a BSc in Artificial Intelligence from the University of Manchester. In past lives I raced snowboards, jumped out of planes, and lived in the jungle.

Full Transcript

Daniel Stillman:

Jennifer, Dan, I'm so excited you're here to join me on The Conversation Factory. Thanks for making the time in your day.

Dan Pupius:

Yeah, thanks for having us. Excited to be here.

Jennifer Dennard:

Yeah, thank you.

Daniel Stillman:

So, all right, Jennifer, you made a very, very reasonable request. When I think about conversations, turn taking is one of the most fundamental and easily identifiable ways to manipulate a conversation for good. And it actually turns out that if women speak first, it's actually best for groups in general, according to my experience, for whatever reason. I'm not sure why that is, but it is, in fact, the case. So-

Jennifer Dennard:

We've heard-

Daniel Stillman:

What's that? I'm sorry.

Jennifer Dennard:

We've heard similar things, that encouraging certain people to speak first helps create a more equal and inclusive conversation.

Daniel Stillman:

Yeah. So Jennifer, I'm wondering if you can kick us off with the question of how you and Dan met and decided to start working together on this company. I'm curious what your version of the story is.

Jennifer Dennard:

And do they match?

Daniel Stillman:

And do they match, right? We should have had this as a double blind interview, really. That would be...

Jennifer Dennard:

So Dan and I met when we were both working at Medium, the blogging company. Dan was leading engineering and his team had actually set up a regular set of meetups or talks, a way of engaging with the community, and I ended up being a guest speaker at one of the events. And so a bit later, I actually ended up joining Medium full-time on the people operations team. And Dan and I ended up partnering a lot on organizational design. So Medium had been using something called Holacracy, which is a specific way of operating that I'd say Dan and I are pretty values aligned with, maybe less tactically aligned with the implementation of. And so Dan and I were partnered with designing a new system as it had been... Medium was moving off of Holacracy. And so we worked a lot together on a tool, internally, to really help the company operate, to showcase what people were working on, and it's, in many ways, a precursor to what we do today, but like company, Medium had ups and downs. And Dan and I were often supporting one another during those ups and downs.

Jennifer Dennard:

And so during one of those downs, I would say we were talking and Dan came in and he was excited. And I was like, "It's a hard week. It's not really an exciting time." And he was like, "Okay, but do you think, generally, we could build better tools to support companies beyond just Medium," and taking what we were learning with the tool that we were building there, and the things we were seeing about how companies operate, and where things broke down to really help other companies? And from there, we just went back to work, but a little bit after that, Dan and I had both left Medium at that point. And Dan was starting to think about starting a company and ended up chatting with me about whether there'd be interest in starting something, like Range, around building tools to support teams and companies and being more effective in their operations. And yeah, it really stemmed from our experience working together at Medium and seeing some of the problems that different companies faced.

Daniel Stillman:

Dan, what would you add to that story? What's missing, from your perspective?

Dan Pupius:

Yeah, I think that's accurate. Yeah, I think, basically, as I was looking around things to do next, leading other teams, bigger challenges, I just couldn't imagine working in a traditional company again and using the traditional tool sets, so I was like, "Well, if I'm going to staff a team to build tools to help us actually work better together, maybe I should actually evaluate whether that's a real opportunity." So I met with investors and then met with Jen and it kind of just... I don't know. It wasn't a decision point. It almost felt like it just gradually happened, and before we knew it, we had a company we'd incorporated and then raised some money and built a team, and it just kind of... I don't know. It felt natural and there wasn't a discreet moment where we were like, "Okay, let's do it." Maybe Jen remembers differently, but I don't really remember the specific decision point.

Jennifer Dennard:

Well, I remember you were actually very specific and intentional on like, "This doesn't have to be a specific decision moment. You can take time and think about whether you'd be interested in starting a company. It's a big decision," which I think was a precursor to some of the ways that we work together now, but it felt very egoless and felt very, like, "I'm not going to be offended if you don't want to do this crazy thing called a startup." I think that level made the conversation much easier and much more of a natural progression, where we got to keep talking more deeply, and then eventually do the official parts around it.

Daniel Stillman:

What was that word that you said, equalist? I couldn't-

Jennifer Dennard:

I don't know if it's an actual word, egoless, like [inaudible 00:05:09].

Daniel Stillman:

Oh, egoless. Yeah.

Jennifer Dennard:

I haven't been subject to too many of these conversations, but I think sometimes when people pitch you their company idea and wanting to work together, if you say no, it can feel very like an attack on them personally, which I get it. It's their company. And Dan approached that very differently of like, "Say yes. Say no. Do what you think is right. Here's some fun stuff to think about." I think he either knows me well or approached it kindly, but the giving me an [inaudible 00:05:37] to think about is certainly a way to get me intrigued about a space.

Daniel Stillman:

It's so interesting because, Dan, I saw you nodding your head. Is there anything else that what Jen said evokes for you?

Dan Pupius:

Yeah. It wasn't intentional. I wasn't scheming of, like, "Okay, how do I get Jen to sign onto this?"

Daniel Stillman:

Well, if you were, you wouldn't admit to it at this point, but fair enough.

Dan Pupius:

Yeah. Yeah, I do have Machiavellian tendencies sometimes, but, no, I think it was just that it is a big decision and I didn't know if there was a there there. And I figured that I needed a team to help me explore that, so started putting the team together. It's like getting the band back together almost because we'd been doing a bunch of this exploration work at Medium. And then we started doing customer conversations, product development, and exploration, and talking to investors and, yeah, it just kind of snowballed.

Daniel Stillman:

It's very interesting because the idea of an invitation begins a new conversation, and there was this in invitational... There was conversations that sort of emerged while you were at Medium, but then there was this moment where you reached out and said, "I'm thinking about this. What do you think?" And it incited another arc of conversations for you all. And it sounds like... It's really funny to think about. This is stuff when I first started thinking about, "What does it mean to design a conversation?" This idea of it can feel like manipulation if you're doing things too intentionally, but you did bring a certain essence, a certain approach to the invitation, which said, "I'd like you to be involved and let's think about it." So I think that's a very interesting moment to look at in the story arc of, "This is a liminal space and it's a generous question." And it sounds like it created a very spacious opportunity for you, Jen, to really step into it intentionally.

Jennifer Dennard:

Yeah, and I think like when Dan says he didn't know if there was a there there... I at least speak for myself and I think this is probably true for Dan as well. Part of why we chose to do a company was thinking about the journey and not the outcome, so startups are very unlikely to succeed, statistically. And so I think it can be similar when thinking about a conversation. Instead of going into it saying like, "This is what I want this person to say or do at the end of it," it's more like, "How do I want to feel during it?" And like, "How do I want the experience to be for both people?" And I think that's kind of how we think about conversations, but also more broadly, as a company, like, "What's the experience? Cool. Are we still having fun? Are we enjoying the adventure?" Certainly there are downs amongst that, but I think part of what has made us successful as a founding duo is that we are in it for the journey versus any specific moment or specific outcome, which I think can be really hard to then deal with the journey, which is quite long.

Dan Pupius:

Yeah, I think we've seen a lot of the power of intention at Medium. So when things worked well and how we laid intentional, explicit processes down ahead of needing to use them, we saw the value in that, and then also we saw when it broke down. So from very early on there, we talked about, how do we prioritize decision making, prioritize ourselves, our families, the founders, et cetera? And then we were very clear about how we want to communicate, our values. And I think some people would probably say that's a waste of time, but I think that sets the foundation and just makes everything easy down the line.

Daniel Stillman:

Well, so now we get into the point of the story where the beginning can seem organic and emergent, and then at some point, you do start to have that question of, as you said, Jen, values versus tactics alignment, right? And how are we going to do things around here, right? Building the culture and the process of how we're going to do things. How do you feel like you have managed that conversation of aligning on how to align?

Dan Pupius:

Yeah, to some extent, this aligns with the whole purpose of Range in the first place, which is that I think human behavior requires structure to facilitate it. Part of the inspiration for Range is from Lawrence Lessig's pathetic dot theory, that human behavior is manipulated by the forces of laws, markets, norms, and architecture. And in an organization, software provides a lot of architecture, which shapes our behavior, but we're not intentional about that software. So the whole theory of Range was about, how can we build software that acts as architecture that shapes the behaviors that we believe to be present in effective teams? So we kind of like thought about the processes ahead of the problems, so what's our cadence of work? How do we communicate? How do we run meetings? How do we talk about things? And just really thinking about the architecture of which we set things up.

Dan Pupius:

And I think we're not super dogmatic and we're flexible, but I think it's something to fall back on. In [inaudible 00:11:09] and everyone culture, they talk about it being the groove. So high performing teams need a home where you feel supported and safe, a groove where these processes you fall back on, and then if you have those two, then you can push people to the edge of their ability. And having a startup and trying all these new... We're doing things we've never done before. We need that to fall back on so we can be at our edge without getting burnt out, and touching against burnout, I guess, instead of going over the edge.

Daniel Stillman:

So Jen, is there more you wanted to "yes, and" on that?

Jennifer Dennard:

Oh, I was just going to say a very simple example of that is, very early on, we set a cadence of meetings of a time for us to kind of connect, a time for the whole team to connect, which at that point was two or three more people, not a huge group, but even just having that simple amount of process or structure of like, "This is when we are going to talk," is really helpful, because then it didn't feel like... It wasn't as hard to raise a conversation or to figure out when we were going to speak about something that we were disagreeing on and you get to resolve. I think those two... "Process" can sound really heavyweight, but for us it started as just like, "When are we going to meet?"

Daniel Stillman:

Yeah, just [inaudible 00:12:26].

Dan Pupius:

[inaudible 00:12:26]. And then names are important as well, so what we're going to meet about. So when Jen and I have our one-on-one, we have a tactical one on one, and then we have a strategic one-on-one and many times we'll talk about tactical things at the so-called strategy meeting, but it keeps us on track, more often than not, to just like, "What are we talking about here?" And then our team meetings, we have an operations meeting with our VP [inaudible 00:12:51], so we're only talking about operations. We're not talking about product strategy or things like that. And then we have an alignment meeting with the leads of all the teams. So the names of these meetings actually set the context and help us keep it on topic and it does deviate, but it is easier to bring back to the core topic.

Daniel Stillman:

Yeah, those names are invitations, right? They set the tone for the-

Dan Pupius:

And the purpose.

Daniel Stillman:

Yeah, the tone and the purpose for those conversations. So you're meeting, the two of you, twice a week?

Jennifer Dennard:

Mm-hmm.

Dan Pupius:

Most times, yeah. We sometimes take a [inaudible 00:13:27], like we'll... If we're exhausted on Friday or one of us is out, we'll, of course, skip, but I think we have, yeah, these two one-on-one touch points.

Daniel Stillman:

Yeah. One thing I'm kind of curious about is I was looking over your website before I came on the call with you all and one-on-ones are one of these things that people sometimes step into these conversations with no plan or with the inkling of a plan, but I think a lot of one-on-ones, there's a clear power differential, right? It's a manager having a one-on-one with somebody who they manage, and you two are co-founders. So I'm curious, in your one-on-ones, how do you... What's that like, right? It's a one-on-one of equals,

Dan Pupius:

I think, before I even talk about our one-on-ones, I think, in general, it's the person with the implicit authority or explicit authority, in some cases... It's incumbent on them to make the space safe, and I will always start the... When I have one-on-ones with people who report to me, it's like, "This is your time. This is where I support you. I am here in service of you, so this is your meeting. It's not my meeting. I get my needs satisfied elsewhere, ideally in a team environment." So that's never going to negate all of the power dynamic, but it does help set the context for that conversation. And I think that's pretty important because if managers use those one-on-ones in a way to have the person report to them, like, "I report to this person," that sets up the tone of the conversation and the purpose of the meeting, whereas if it's actually oriented much more, "This is where I support you," that's how you help people achieve... That's where they're honest with you and when they're open and vulnerable and where you're most likely to learn more things, so I think that's some framing, but I don't know about our one-on-one, Jen, how you feel about that.

Jennifer Dennard:

I think one of the things that we do is we typically have pretty clear areas of ownership, so I don't know. Just like a, I guess, regular one-on-one, we usually have an agenda. We have the topics we want to talk through. It's usually like either of us sharing updates on whichever area we're owning for the time being, and sometimes that ownership gets passed and handed off, sometimes week by week, depending on what's happening, but that is something that I have found upon reflection but upon talking to other founders about sometimes the harder areas when they work with one another. That's been really powerful for us because it lets us have, I think, one, some mind space, because each of us aren't owning everything and, two, the autonomy to go figure things out and then come back together. So I find that often the best analogy, I would say, is someone that you've worked closely with, who you're doing a one-on-one collab with, where you're just working through a problem. I feel like that's often how our one-on-ones feel to me and we just have more problems to work through than the average one-on-one collab.

Dan Pupius:

Yeah, it sometimes feels like a relay race to me, where we're handing off the baton, and sometimes we're like... I guess the analogy doesn't fit perfectly because we have a quick discussion of whether we should hand off the baton, but we do have explicit owners and I do think one of the cool things about the way Jen and I work is we pass ownership back and forth more dynamically than I've seen other people and other people I've worked with.

Daniel Stillman:

Yeah, because that's one of the things that I was wondering, is the... I've heard this before, that some clarity around roles and division of labor is really helpful. Otherwise, there can be unclarity, for lack of a better word, but it seems like the other side to the coin is also true, which is flexibility to pass things back and forth and to shift and alter who's doing what is also really powerful. I'm curious how you navigate that conversation.

Dan Pupius:

Well, I think, we have a Venn diagram, so there's the stuff that's clearly mine and clearly Jen's, and then the middle bit is the messy bit. And luckily, there's not too much there, though that's probably the most critical part of the business for the last 18 months or so, so lots of back and forth on marketing and sales, for example, but it means that we still have these areas, where's it's just very clearly our areas of expertise, where we get to have mastery and complete autonomy. And then it's really the messy middle where we go back and forth. I think if it was all messy, that would be really difficult, or if only one of us had areas of specialization, that would be really difficult as well and probably really disempowering.

Jennifer Dennard:

Yeah. A lot of the decision of who takes something usually relates to bandwidth, and that's both time available but also energy. Sometimes Dan or I will take something just because other person's like, "Oh, I cannot keep doing that," or I don't quite have capacity. And I think that's maybe another thing that we haven't talked about yet in this conversation, is we have invested in through process and tried to cultivate a sense of, I think, safety and belonging on our calls, on how we work together. And that allows me, for instance, to say something like, "I just had hip surgery two weeks ago," and to be like, "Hey, my pain level before or after that is really high. I'm just not able to be what you might consider a normal capacity for me." And Dan [inaudible 00:19:21] hear that and, at least my experience of it, to not feel blamed at all, just to be like, "This is a fact about the bandwidth that we have as a collective system." And I think that allows that kind of handing off of responsibilities in a way that doesn't feel contentious.

Daniel Stillman:

Dan, what more would you say about that?

Dan Pupius:

Yeah, I think Jen has to have a lot of bravery to bring those things up, so I think a lot of the credit goes to her in having boundaries and sharing what she needs in this situation. I do think our history really helps and we've been working together for so long now, and then some of the structure as well, but I think it also takes bravery.

Daniel Stillman:

Yeah. What's some of the structure that you feel makes that possible? You mentioned the architecture is one of the components that guides human behavior. What kind of intentional architecture do you feel like makes that safety possible?

Dan Pupius:

Yeah, so I think one of the key things is... One of the foundational things, and again, this relates to what we're doing as a company, is visibility. Daniel Coyle talks about this in terms of belonging cues, and belonging cues being these micro-interactions that remind you that you're on the same team, but I also think that if there's a lack of visibility into what you're working on and what you're doing, trust just naturally degrades over time. So making sure that we are in sync and seeing what each other are doing and just having a general pulse is super valuable as setting the foundation. And then as a company, we've just been really careful about building these moments for connection, which might, to some people, seem like a waste of time, but I think is really valuable as a way of building that trust and vulnerability, which is the only way that you can have those conversations. So giving gratitude is hard. I find it difficult, but creating structure where people are nudged to give gratitude is really powerful or receive gratitude to reflect and celebrate all these little things of what build up and create the foundation.

Daniel Stillman:

Yeah, I noticed that you mentioned a tactical and a strategic meeting, but I didn't hear a catch up or a vibes meeting.

Dan Pupius:

A vibes meeting.

Jennifer Dennard:

That's how we start all... So all of our meetings internally start with a check-in round, which is where you kind of... How you're doing, green, yellow, red, and I feel like Dan and I... Our meetings in particular often start with, "How are you really?"

Daniel Stillman:

Yeah, just go straight to the second question. "How are you really?"

Jennifer Dennard:

Yeah. I think we try to both be vulnerable with our team to the extent that we can, but there's also a level of we are the leaders and sharing how difficult things might be at a certain time is not so good for the company. And so I think that it is helpful to be able to share authentically in those meetings, even if sometimes I feel like I have to hold some of that back for the whole company.

Dan Pupius:

Yeah. Yeah. And I think even though we have the tactical and the strategy meetings, I think sometimes we're okay putting the agenda aside and just losing the time, and then we'll just... If we need it, we'll schedule a followup, but I don't know about you, Jen, but I find that also the last two years have just been so crazy that it's sometimes just nice to escape into abstract problems relating to the business instead of having to worry about the world that's collapsing around us, so there is some escapism there.

Jennifer Dennard:

Oh, totally. I think we both have that in our personalities, which is probably why [inaudible 00:23:15] helpful.

Daniel Stillman:

I don't think you two are unique in your desire for escapism, but I'll just say, and this is a really interesting thing to highlight, is there are some people who say like, "Oh, let's have a meeting that's just about human connection." And then there's baking it into all meetings.

Jennifer Dennard:

I don't know. You could kind of put that as a motto of Range, that we think that putting human connection directly next to the work is what makes it effective. And there's research to support that related to off sites that are just about happy hours and things aren't as effective as ones that incorporate aspects of work, but we found that, certainly, culture only meetings... We have game times or [inaudible 00:24:03] audio only. We certainly incorporate that as an aspect of our work, but it really does, I think, a disservice to people to have that always be a separate thing, because it makes it... To the extent that architecture and these structures influence us as humans, it makes it feel like there's work and then there's being a human. That's just not what's true. We are all humans at work, and I think that's something that we incorporate a lot into the software of our meeting tool, of our check-ins, all the different aspects, but also into how we operate as a founding team.

Dan Pupius:

I'm sure most people can resonate with this. You have a happy hour where everyone's chummy and being really friendly with each other, and then the following day, people are being passive aggressive over work email or tickets. And it's like you segment the two personalities. There's like, "We're all a team playing ping pong, and then we're arguing with each other over the work stuff." So bringing that sense of belonging into the work stream is... It's just really valuable at actually building the team aspect.

Daniel Stillman:

Yeah, very much so. One thing I think you mentioned, Dan, was this idea that in a one-on-one where there's a management relationship, it's about inverting and saying, "This is your meeting and I'm here to serve you," and underlining it was this idea of, "I'm getting my needs met elsewhere in self care." And I'm curious, you two can't manage each other without you two learning how to manage yourselves. And I'm curious what you do, Dan, and Jen, I'll ask you next, what'd you do to take care of yourself? Before we started recording, we were talking about how we get more protein into our diets, of course, but really, I'm wondering about how you fill your own cup so that you can come to the meetings with Jen in a place that's helpful.

Dan Pupius:

Well, I think the reality is that most times I probably come to the meeting with my cup three quarters full. And if we didn't have that sense of... If we didn't have that history and the foundation, it would easily overflow, especially in today's world, but because of all the stuff we do, it doesn't overflow. And in terms of self care, I have two small kids, live in the city. I don't have that much time. I just have hot baths and go for a run as my self care. And it is minimally viable, but I do think a lot of the work we've done over the last five years and then some of the coaching we've done outside has been really valuable at helping me have more capacity and helping me rejuvenate more quickly. But, yeah, if I'm sleep deprived, I will be a bit sharp and I will step over the boundary of what is safe conflict, right? And that could be a catastrophic event if we didn't have that foundation. So I think that's kind of what's interesting, is that if you have productive conflict or if you encourage productive conflict, there will be times when you step over the boundary and it's what you do then that is the important thing in how you recover.

Daniel Stillman:

Jen, what do you do when Dan gets a little sharp?

Jennifer Dennard:

Usually, I pause. Like Dan kind of knows as well, I'll be like... I look away and I'll be like, "Okay, let me..." And then I usually try to pull out what it is underneath, like what is he trying to say or what's the best interpretation? I think something Dan maybe came up with at Medium or we started using there was the reasonable person principle and the idea that whatever the person's sharing, there's a reasonable explanation. And so I think I probably... Took me some time, probably... So Dan at Medium was more my mentor, I would say, and so to come into a co-founding, peer relationship, as a woman who's also younger, I think it took me probably the first few years to really step more into like, "We are peers." And I distinctly remember Dan going out on a very abbreviated paternity leave, unfortunately, at the start of the pandemic. And I was like, "Oh, Dan doesn't know what he is doing either. He just comes up with an answer when I ask, and I can do that."

Jennifer Dennard:

And I think feeling like a peer in those conversations, to the point we were talking about earlier with power dynamics and stuff, really changes how sharpness lands. It doesn't feel personal. It feels like Dan didn't get enough sleep last night. I think, if it ever starts to feel personal, I also feel comfortable being like, "I'm going to step away from this call. I don't think we're being productive." And we've done that here and there and instead come back together. And I think knowing that, just like any relationship that when you have conflict, even if it does go into a space you're not comfortable, that you have the ability to repair, in my mind, matters because you're never... Whether it's your founding partner or a friend or a spouse, you're never going to not have conflict, unfortunately. And so [inaudible 00:29:24] that you can, typically make it productive, and then when it's not, that you can repair and talk through whatever underlying issue, that feels important to me. And I think we have that really shared understanding,

Daniel Stillman:

Jen, this is such a powerful point. And I think this is something I learned from the world of couples therapy. The ability to actually pause a difficult conversation can seem like a threat if it's not done correctly, to say, "Hey, look, I'm not comfortable with where this is right now," or, "I don't feel well resourced," or, "Maybe we should just pause this and come back to this." What verbiage do you use in those moments to slow it down, to cool down the conversation and to separate and come back? I know you said it only happens occasionally, so you may have to stretch your memory to go back.

Jennifer Dennard:

I'm trying to give a best case. If we're candid, right, sometimes I'm like, "I'm getting upset." And so I'm like, "I need to take a break." And it's not like fairly said in a nice, calm way that we want to when we're in therapy, where it's like, "Oh, say, I think I should take a moment." Probably doesn't happen exactly that way, but just usually something like, "I don't think this is constructive," like we're kind of talking back and forth or, "Let's take a break. Let's revisit this later," because if we've gotten to that point, we've probably also gone over on time, so there's a clear, like, "Hey, we're not being constructive here."

Daniel Stillman:

Yeah. I call this noticing and naming. You're like, "I am noticing my own situation, naming it, and taking it." And I'm talking over Dan, which is...

Dan Pupius:

No, that's okay. No, I think having a language for it is really important and, yeah, some of the models that we've learned about around psychology. I think it depersonalizes it a little bit. So this is from Kegan, but we might say, like, "We're not in level four anymore," or, "We've got hooked," like we've got hooked by the conversation and it kind of just pulls you out of being hooked. It's almost like if you're angry, just saying, "I feel angry," is enough to calm the amygdala. So there's these really interesting language hacks that can reset things and then stepping away. And I do think the repairing and recovering is really important. You can't just push it under the rug. And then if other people were in the meeting as well, making sure that they see the recovery, which is the same as with parents. You can't have parents argue and then make up in private. They have to make up in front of the kids. Otherwise, they don't learn about conflict resolution, so it's a similar principle.

Daniel Stillman:

You mentioned, "We're not in level four anymore." I'm not sure if I know the framework that you're referring to.

Dan Pupius:

So Robert Kegan's book, Evolving Self, provides this model for adult cognitive development and it's essentially... You have the egocentric self, you have the socialized self, the institutional self, and it's ways that your mind makes meaning given the situation. And we are constantly fluctuating between those levels as adults. And it's [inaudible 00:32:39] useful because if someone attacks you on the street, you want to drop down into a level one egocentric self to save yourself, but in the work context, it's not very... We have similar reactions and our brain drops into a different mode of operation and meaning making, and it's just not helpful because we're not being attacked or anything. It's our brain being tricked. So it just gives us some language. And the egocentric self is very black and white. It's very like, "Me, them." The socialized self is all about the relationship and the connections, and then the institutional stuff is a higher level systems thinking space. And even if the model isn't correct and potentially reductive, models might be wrong, but they're still useful.

Daniel Stillman:

Yes.

Jennifer Dennard:

And I think something we do well at this point in our co-founder relationship is identifying when the other person is dropping down. For example, I think, the counter today in maybe Dan being sharp is I will start to speak... If I'm the one who's less resourced and not doing well, I'll start to speak in shorter sentences. I will just seem more flustered. I will actually sometimes turn slightly red. And I think both of us sometimes will say to each other, like, "What are you worried about?" And/or say like, "Well, here's what this is triggering for me," or, "This is what this is making me think about," and the thread I'm pulling on. And so sometimes that really helps us get out of the conversation where we're talking about a very specific thing. And it's really like, "Oh, this other problem that's triggering for us." And less in the therapeutic sense of triggering childhood trauma and more like triggering like, "Oh, I'm actually really worried about this other thing on the sales team or the marketing team, and that's pulling on this concern, even though it seems to be a [inaudible 00:34:35] question."

Daniel Stillman:

Yeah. Although I get the sense that, just from my own experience and relationships, it's hard to say to someone, "It sounds like you're kind of in level one right now, so let's start this again when you're ready and in level four."

Dan Pupius:

It's definitely an ouch. It can be a bit of an ouch, but it can also be a bit of a shock to system because, again, the label and... I don't know. Yeah, there's definitely like, "Oh, man," like a little bit of embarrassment, but then you know that we're in a safe space. There's a lot of regard and you can come back and there's no judgment, and then we get back into the space. And I think having the ability to actually jump up and down through these mental spaces is actually really valuable, instead of getting stuck in them.

Daniel Stillman:

Yeah. Well, so shockingly, our time is running nigh. I'm wondering what I haven't asked you about managing your relationship, designing your conversation, that I ought to have asked you. And Jen, I'll start with you, to see if anything comes to mind.

Jennifer Dennard:

I think there's often a power dynamic in founder relationships. I think just having been a part of a number of COO and collect-all groups, there's often a power tension with the CEO. There's certainly power dynamics associated with gender and with age, particularly in the tech industry. And so I think it's something that I often encourage people to think about and focus on early on. When we first were designing Range and we started talking about equity division amongst the founders, we were pretty particular in terms of what we decided would impact equity. And I would say I got a much more equitable portion than I would with most male CCO co-founders, and I think that speaks to Dan's values but also helped really set the framework and groundwork for me to feel like a peer.

Jennifer Dennard:

And Dan has put in work for that to feel that way. And I think sometimes there's stuff early on, that the co-founder relationship gets off on the wrong foot, even if it's people who work together for a long time, because that perception and that difficult conflict early on of, "Are we equals in this? How are we approaching this?" doesn't quite happen. And then so that encouraging of conflict in that discussion, I think, is really important in thinking about the different power dynamics that can emerge, even if you consider yourself to be peers. And I'm very grateful that Dan is our CEO. He deals with stuff that I don't, and I appreciate that a lot.

Daniel Stillman:

How about you, Dan? What haven't I asked you that I should ask you?

Dan Pupius:

I don't know. I think you kind of hinted this earlier, but we went a different direction, which is that looking after yourself and attending to yourself is so key, because if you're not in a good state, you can't be a good teammate and you definitely can't be a good leader. And I think many leaders aren't vulnerable about that and they don't focus on their strengths and weaknesses and addressing them and thinking about them, and what are their personality dynamics that may be suboptimal or rub people the wrong way? I'm very aware of how sharp I can be and how scary I can be, and I've worked for 20 years to try and correct that, so I think the personal leadership is so important as a foundation.

Jennifer Dennard:

[inaudible 00:38:20]-

Daniel Stillman:

Again, you mentioned you... Oh, sorry. Go ahead, Jen.

Jennifer Dennard:

Oh, I was going to say, and being aware of one's own mental health. Certainly, in the last five years we've had ups and downs and at a pandemic and all the things that have happened. I think being able to own that versus put it on the other person or the company is really important.

Daniel Stillman:

Yeah. Dan, you mentioned coaching has been part of that for you. Is there anything else, besides running and hot baths, that is part of you sustaining yourself and coming with your cup three quarters full?

Dan Pupius:

Yeah, me and my wife... We talk about this a lot and getting out, and especially when we had a young child, it was really hard to get out of the house, but we'd force ourselves to go out into the wilderness and go hiking, and that can be really valuable. So coaching. We do couples therapy as well, which is really, really helpful, just as a way of building our relationship, making us stronger parents and showing up better for each other. I don't know. Probably too much alcohol, not sleeping enough... All these things are problems. I'm probably not super healthy right now, to be honest, but at least we're surviving.

Daniel Stillman:

At least you're getting enough protein.

Dan Pupius:

Yeah. Well, as of last week.

Daniel Stillman:

As of last week. Well, next week's going to be better. Jen, what do you do to fill your cup?

Jennifer Dennard:

Similar tactics of coaching and therapy, I think. Normally, I run. As I mentioned, I got hip surgery, so I've been... I really like reading. It's my form of escapism, to really go deep into a moderately well written to badly written or poorly written fantasy or sci-fi novel, just to be very separate in a different world. My sister's a fantasy author, so it definitely runs in the family, but... And then, yeah, being out in nature. Right now, I can't go very far, so just sitting in our backyard. We have a garden and taking that space. I think a recent thing I've been trying more is expressive writing, where you just write for 15 minutes, and it doesn't have to be... Not really a journal, per se, of what happened, but more just like, "Here's how I'm feeling." That, I've historically found useful, particularly in moments where I'm keyed up or need to process and don't want to necessarily just ignore how I'm feeling, but want to just help the emotion kind of work through.

Daniel Stillman:

Yes. I went to a workshop years ago with Julia Cameron. It was a writing workshop. I went with my mom. It was super fun. And basically, whenever anybody stood up and said, "I'm having some trouble with this, this, and this," she would say, "Are you doing your morning pages?" That was her... Just the three pages of just long hand, first thing in the morning. And whenever I get below zero, I bring morning pages back in.

Dan Pupius:

I think maybe the lesson there is it's less about the tactics, but the important thing is the ritual, so having these rituals. So rituals for connecting with your partner, connecting with your kid, getting physical health, getting good food, whatever it is, disconnecting, escaping, making sure you have those rituals laid down so that when things get hard, you have something to fall back on.

Daniel Stillman:

Yeah. Well, this has been really lovely. I want to thank you both for your time. If people want to learn about all things Dan and Jen, are there other places they should go, besides Range.co, that you'd like them to go to?

Dan Pupius:

I don't-

Jennifer Dennard:

That's the main thing. Check out our... We have a series of podcasts and interviews with other teams and how they manage some of this, called How Teams Work or Lead Time Chats. Both of those are really great resources, I think. We care a lot about educating the community. It's not just like there's some scholarly paper that has the best practice. It's also like, how do people actually do this? So we try to share a lot of that information on our blog, which we also share out on LinkedIn and things like that. Feel free to connect directly on LinkedIn too.

Daniel Stillman:

Well, sweet. I think I'll call "scene" and just make sure that you two... Well, let's do a checkout and make sure that everything felt awesome.

Building an Integrity Culture: Co-Founder Conversations

In this conversation, I sit down with Huddle Co-Founders Stephanie Golik and Michael Saloio.

Huddle is a platform for designers and builders to invest in startups with their time. 

Stephanie has spent her career building alongside founders at studios and leading design and product at fast-growing tech companies. She was an early design leader at Cruise, building user experiences for self-driving cars. Before that, Steph was Head of Product at Mapfit (acq. by Foursquare). She's a proud Cuban-American born, raised and currently residing in Miami.

Michael is a product and team-focused entrepreneur and investor. He’s spent his career working with technology executives and investors. As an investment analyst at Oppenheimer & Co., he followed some of the biggest names in technology including Cisco, EMC, and Apple. Prior to Oppenheimer, Mike covered special situations at Sidoti & Co.

Over the past five years, Michael reimagined his career to focus on early-stage businesses. He was the first employee at SuperPhone, a messaging application backed by Ben Horowitz, Betaworks, Bessemer, and more. Since 2014 he has consulted with, invested in, or advised more than 35 startups that have raised more than $200M in venture financing.

I met Michael years ago and have tracked his rise…when I saw that his latest venture raised 3.3M and was a co-founded company, I reconnected to include him in my co-founder conversations series.

My question throughout this series has been simple - what does it take to build and sustain a powerful co-founder relationship? 

Michael and Stephanie shared some of the insights and principles that helped them do exactly that.

The biggest aha was the umbrella concept of an Integrity Culture, and how many powerful values fall into place with a focus on Integrity.

As Michael points out, it’s not just “I do what I say I will” it's also about a culture of Coaching and Feedback to help everyone right-size their commitments and to give themselves (and others) feedback along the way when they find themselves falling short.

Stephanie and Michael share a conversation format that they use over the course of each week to keep their team on track and in integrity!

Integrity Culture also implicates one of my favorite words: Interoception, a concept I learned from Food Coach Alissa Rumsey.

Michael and Stephanie’s vision of an integrity culture is one where you commit to a thing because you are intrinsically motivated to do it, not through force or pressure…you self-select the thing you are going to do. And that means you know what you want! Interoception is the ability to feel and know your inner state. 

Some additional keys to a powerful co-founder relationship that line up with the other conversations in this series are the ability to have Healthy Conflict (rather than an unhealthy “peace”) and the regular asking and giving of generous and generative deep feedback.

One other insight that was fresh for me in this conversation was Michael’s idea of a good co-founder relationship as one that is “Energy Producing” vs. energy sucking. A powerful co-founder relationship is like a flywheel - the more energy you invest into it, the more energy it throws off.

Be sure to check out my other co-founder conversations, like this episode with Jane Portman and Benedikt Deicke, co-founders of Userlist, on how they connected through shared communities and learned how each other really worked through real-world, previous projects.

You may also enjoy my interview with Carolyn Gregoire and Scott Barry Kaufman, the co-authors of the 2015 bestseller, Wired to Create, where we unpack how they managed their working relationship.

And if you really want to dive deep into the idea of being a conscious co-founder, make sure to check out my conversation with my friend Doug Erwin, the Senior Vice President of Entrepreneurial Development at EDAWN, the Economic Development Authority of Western Nevada.

Links, Quotes, Notes, and Resources

Huddle website

Minute 16

Michael Saloio:

A lot of my challenges in the early days were, I had to define my own schedule. Sounds like really basic stuff, but going from an investment bank where there's pretty clear structure and a way of doing things, highly professional, and then having to wake up every day and figure it out, was that I had to really plan my week, like really relentlessly. And it came down to just doing what I said I was going to do. I have a much broader definition of what integrity is now. I became really obsessed with the... I still am very obsessed with the idea of integrity, but I wanted to build a culture where instead of it being based on hours and management, it was based on setting really clear values and goals and letting people self... I don't want to say self-identify, but letting them say what's possible for them.

And then kind of challenging whether or not that was possible. And then holding them accountable to doing what they said they were going to do. But more than that, calling themselves out when they weren't going to do it. That seemed like a much better model to me than being scared or making them wrong for not doing something, you know?

Minute 17

Michael Saloio:

The way that we do things is on Monday, we have a meeting. It's a standup where we all say what we're going to do for the week. And then on Thursday we have a check-in where we're really honest about whether or not it's going to get done. And we give ourselves the opportunity to ask for help. And that's it, you know? And so instead of feeling like you have to hide or you have to be wrong for not having done something, it's like, "Hey, look, I said, I was going to do this thing and it's just not going to happen this week because these three things happened." So at least it opens up a conversation to, "Well, what do we have to do to actually get it done?"

Stephanie Golik:

What I really loved about it, within our culture that I've started to see is like, it really is... culture is, you get what you recognize or what you praise, I think is the phrase. And it feels like we just really praise when people step up and say like, "Yeah, I said I was going to do that. And I didn't, and I'm not sure if it's still important." Just that level of honesty. Besides that, it's just like, I think a real bonding and humanizing thing to do for a team. It also just gets us back to performing. We move past the... there's a lot of effort in hiding and feeling crappy about not doing something, right? That's just effort that doesn't... we're just kind of trying to say, like, "It doesn't need to be there. We're all humans and we're all trying to do our best and build this thing together."

Minute 22

Stephanie Golik:

And in that moment of deciding to continue to work together and move to this other venture together and take this risk, I felt like I could give him some feedback and we went for a walk in Soho and I gave him really direct feedback and we had a really great conversation that also was a prompt for Mike to also get into coaching and a couple other things, which was like... being really good at taking feedback is an incredible quality. And I think having that kind of experience early on in a working relationship where it goes okay.

You get feedback. It not just goes okay, but it actually really furthers your ability to work together. I think it set the stage for lots of versions of that conversation that have happened over the years, both ways. But you know, there's lots of working relationships where it's just not as easy to have an honest conversation about something that's, again, not working for you or making you feel a certain way and you end up holding it in, and/or doing other things to skirt around it that just don't get to the core problem because you don't have that level of kind of open dialogue. It feels like we established that open dialogue pretty early on, like long before becoming co-founders. So by the time that we got into this more deeper relationship and engagement, we had a lot of that foundation, which I think has been really helpful.

Minute 42

Michael Saloio:

I wrote a blog post on this, it's called You Don't Need a Co-founder, which is so funny because we're sitting here saying that co-founders are amazing. But what I meant by that, I meant a couple things by that. One is, what you really need is people around you. The relationships can take a lot of different shapes or forms. I had some kind of shotgun co-founder wedding type vibes as well. I would just say go slow. It takes a lot of time to understand whether or not you're going to be able to build a company for... Just think about how much time you spend working.

You're going to go into something with someone that might take seven years or 10 years or longer, if you keep going with it. Right? So it takes a long time to understand whether or not you're going to have healthy conflict resolution or whether your skill sets are matched. Right? Another thing we haven't talked about is like, Stephanie is a designer and builder, I'm an ex finance guy who's kind of good at sales and business development and vision. And we're both actually really, really visionary people. But we have the ability to actually make things together. There's a skill match as well. And also our company works with founders, right? So we see a ton of partnerships. So, I guess two things. If you're going to go into work together on something, you got to make sure that you have complimentary skill sets, which is very basic. But two is like, go slow. Get to know somebody. Go into battle with people that you know how to work with.

More about Stephanie and Michael

About Stephanie:

Stephanie Golik is a founder at Huddle, where designers and builders invest in startups with their time. She's spent her career building alongside founders at studios and leading design and product at fast-growing tech companies. She was an early design leader at Cruise, building user experiences for self-driving cars. Before that, Steph was Head of Product at Mapfit (acq. by Foursquare). She's a proud Cuban-American born, raised and currently residing in Miami.

About Michael:

Michael Saloio is a product and team focused entrepreneur and investor. He’s spent his career working with technology executives and investors. As an investment analyst at Oppenheimer & Co., he followed some of the biggest names in technology including Cisco, EMC, and Apple. Prior to Oppenheimer, Mike covered special situations at Sidoti & Co.

Over the past five years, Michael reimagined his career to focus on early-stage businesses. He was the first employee at SuperPhone, a messaging application backed by Ben Horowitz, Betaworks, Bessemer, and more. Since 2014 he has consulted with, invested in, or advised more than 35 startups that have raised more than $200M in venture financing. Mike is now a founder at Huddle, a platform that lets early-stage startups connect with and hire top fractional talent for cash and sweat equity.

Full Transcript

Daniel Stillman:

We're live. Welcome to the Conversation Factory. Michael, Stephanie, thanks for making the time for this conversation and finding a room where Stephanie, maybe somebody won't bump through, which is all good.

Michael Saloio:

Yeah. Thanks for having us.

Stephanie Golik:

Nice to be here.

Daniel Stillman:

Thank you. So, all right. We need to give some context to the people. Can you explain a little bit just about your company and what it's all about? And then maybe we can talk about the origin story of the two of you behind that.

Michael Saloio:

Sure. Steph, you want to tell Daniel here what Huddle is?

Stephanie Golik:

Sure.

Michael Saloio:

What's a huddle?

Stephanie Golik:

What's a huddle? Well, Huddle is a builder community. We are a community made up of over 250 now independent builders from around the world. And the Huddle platform connects all of those independent builders with startups who need help in the early stages of company building. So, we form teams for them of these builders, make up of product development and marketing talent. Anything to add, Michael?

Michael Saloio:

We are a seed stage company based in Miami, Florida, where we both are currently. Stephanie recruited me down here during the heat of the pandemic to start our company together. And we've been building Huddle officially since October 2020. That's when we launched. I guess we started in the summer of 2020. And Stephanie and I have been working together in different ways since 2015.

Daniel Stillman:

Whoa. How did you two meet all the way back in 2015? What's the meet cute?

Michael Saloio:

The meet cute?

Daniel Stillman:

Yeah. Yeah. That's the phrase, Stephanie, I think you maybe know it. I mean, it's like in a rom com, it's like how the two people stumble upon each other. It's the-

Stephanie Golik:

The moment.

Daniel Stillman:

The moment. The moment of serendipity that brought the two of you in this big, crazy topsy turvy world. How did you two actually meet?

Stephanie Golik:

When our storylines converge?

Daniel Stillman:

Yeah. When did your storylines converge?

Stephanie Golik:

It is a good story. So, I was just starting out in my career in 2015. I had previously been in architecture. I had just moved to New York. I was starting to get into product design, user experience design, working on side projects. And Mike actually hired me at my first full-time job. He was helping to run a product studio at the time. Mike interviewed me and it was like the best interview I've had to date. We just like, had a great convo over some hot mint tea and just immediately had a great rapport. And the two of us just ended up really enjoying working together and ended up leaving that studio, jumping to another studio together. And just over the years, have continually found ways to kind of come back and work together on things.

Daniel Stillman:

Hmm. Michael, do you remember that? You had a laugh.

Michael Saloio:

Yeah.

Daniel Stillman:

You were like, "Mint tea. I remember the mint tea."

Michael Saloio:

Well, I'm laughing because the best interview I've ever... It probably was my best interview too, all things considered, now that we're here building this company together. But the reason I laughed was because I had no idea how to interview a UX designer at all. And I think I just really liked Stephanie and I liked that she was building and designing things just in her spare time and was sort of a self made, self-taught product designer. And we were like a really scrappy bunch at this studio. So, she kind of fit right in. But yeah, it was a really casual conversation at the Crosby Hotel in Soho, which was around the corner from the office we worked at 73 Spring Street.

Daniel Stillman:

Wow.

Stephanie Golik:

Shout out.

Michael Saloio:

Shout out to 73 Spring Street.

Daniel Stillman:

So you were like the spark of... I mean, for the lack of a better word, attraction of the scrappiness, that you admired this quality in her. And the other thing I'm hearing is that the conversation was just really casual, but also engaging and fluid.

Michael Saloio:

It was casual. Well, you said it really well. It was casual, engaging, and fluid. It was also very centered on making things and building things. So, that's actually a cool part of the story too, is upon first meeting, we dove right into our passion for startups and building things.

Stephanie Golik:

Yeah. And I also remembered, besides it just being easy to talk and start riffing and collaborating and all that stuff was that Mike sort of jumped past the job we were even talking about and was asking me bigger questions about the next 10 years and got us into much more interesting conversations than many interviews I've been on. So, that was impressive to me as well.

Daniel Stillman:

That's really interesting. What was the question that zoomed out and started to create that bigger image? That's so interesting.

Stephanie Golik:

I think it was something along the lines of like, "For a second, let's just like, screw this job that we're talking about. Really. Let's keep it real. We're having this conversation about like building stuff, like what do you want to build? What do you want to do?"

Daniel Stillman:

Yeah.

Stephanie Golik:

And so to have that kind of branch in the conversation in our first chat, I think was pretty telling.

Daniel Stillman:

That is interesting.

Michael Saloio:

Wow.

Daniel Stillman:

Yeah. Do you remember this, Michael? And I'm curious if you remember-

Michael Saloio:

I did do that.

Daniel Stillman:

...Stephanie's answer.

Michael Saloio:

I don't remember asking that. Let me rephrase that. I do remember asking that, but I didn't remember until now, like re-remember that I actually asked that question. Do I remember what her answer was? I don't think I do. Do you remember what your answer was?

Stephanie Golik:

I think it was that I want to start my own company. Not a huge surprise.

Daniel Stillman:

She said, "I want to make Huddle, this sort of like, you know, agency that's..." No, sorry. That's a bad joke. You predicted Huddle in 2015. Obviously.

Michael Saloio:

We kind of did. We actually talked about that today in one of our internal meetings, that although we started Huddle really officially in the summer of 2020, we've kind of been working on this since 2015 in some way, shape, or form.

Daniel Stillman:

Say more about that.

Michael Saloio:

I do remember that you said you wanted to start your own company, for sure. I also remember in a later conversation that you wanted to be an empathetic leader. Do you remember that conversation?

Stephanie Golik:

Yeah, I do. I do. I don't remember what the context was, but I remember we had a good chat about what I wanted to be. And somewhere it landed with, like, "I really, really look up to strong leaders that have a really warm, empathetic quality." And that's what I would strive to be.

Daniel Stillman:

That's a really nice tension, like strong and warm at the same time. That's beautiful. It's really interesting, Michael. Because I know that, I guess we were just talking recently. I can't remember now if it was 2018 or 2019, where you were thinking about this, a community based approach, like where did the community element come into the conversation for the two of you?

Michael Saloio:

I can tell you where it came in for me in 2018, 2019. Without going too deep down the rabbit hole, I had worked at a prior startup called Super Phone, which was about owning your audience as an artist or creator. And the founder of that company, Ryan Leslie and I, had many a late night chat on just the power of relationships in general. And we talked about the concept of a thousand true fans and how changing the 20 to 30 people in your text feed every day is life changing. Like if you scroll through your text feed, that's your life. Your life is the communication and conversations and relationships that you build with people. And that led me to start a dinner series about wanting to connect people who might not ordinarily meet. Primarily because Ryan was an artist and had all of these people that I had not really bumped elbows with working in finance in New York, for the first part of my career.

Michael Saloio:

And later on, as it relates to Huddle, I was building what looked like a more traditional product and startup studio and basically realized that the most important thing I could do is put the best people in the room. That was it. I kind of had the epiphany as a first time entrepreneur that I wouldn't be better at company building than anybody else. And it was really the entrepreneur and the people that the entrepreneur surrounded themselves with, that was the most important part. I didn't think that I was going to develop a better sprint process or stage gate process or I didn't have any of that stuff. I just knew that I liked founders and I liked creativity and I liked startups. And people just started organically coming to me and Stephanie, because Stephanie and I were always helping our friends launch companies on the side by helping them with their pitch deck and building their app.

Michael Saloio:

Or building whatever they were building. And people just started organically coming to us and saying like, "Who's the best designer you know? Who's the best developer you know?" And I had organically built this list of people because of the dinner series. And so fast forward to 2020, all that stuff. Talked a little bit more about the community and how we launched. But for me it was like, the epiphany that I kind of needed to get out of the way more than I need to get in the way. So instead of like, coaching and strategizing with the founder, it was better for me to just create a container or a space where I could put people who were really good at what they did in the room. And the magic would happen from there.

Daniel Stillman:

Yes. Yeah. What does that spark for you, Stephanie?

Stephanie Golik:

Yeah. That's super interesting. Yeah. I feel like the way that I kind of arrived at some of these things is like, more through the lens of some of the things I learned in architecture and kind of that just made me think of it, Mike, with creating the container. It's like creating a space for facilitation of a thing to happen is just very interesting and exciting to me. I love designing and building things that become interfaces or tools for people to connect and do things together. And that's really what community building is. It's like, just creating that space and that interface for people to meet and do things, in its simplest form.

Michael Saloio:

And I think we both just wanted to make it easier for people to make things together. Stephanie and I worked inside of a lot of different startup studios and accelerators. And it also always seemed like they did a really good job with mentorship and advisory, but they were always looking for a designer and always looking for an engineer. And so fast forward to the pandemic, everybody's working from home. A lot of our friends and collaborators are starting new things, maybe because they were worried about their income or maybe just because they had more time in their day to work on things that they wanted to work on now because they didn't have to go into an office.

Michael Saloio:

And so at the same time, you had all these people who also had spare time to start freelance, like a lot of the way that people start as entrepreneurs, including us, is just by becoming a freelancer. Becoming a freelancer is a great way to become an entrepreneur because you do things on your own for the first time. You start an LLC. You have to figure out your accounting. You have to meet collaborators. And so the two worlds were just kind of colliding. It felt very much like at the same time, that we were like, "Oh wow, there's going to be a lot more people starting things. And they all need to connect with design and development talent. So maybe instead of a studio, we should be a platform that facilitates that."

Daniel Stillman:

Yeah. And that goes to your point, Stephanie, of like, being the architect of a system of conversation, a space where people can gather. In the last conversation Michael and I had, one of the things that really impressed me was the culture of the company you two are trying to build. I'm wondering if you can say something about what an integrity-based culture means to you? How do you feel like you're doing that on purpose intentionally with the space that you're building for yourselves? Not to put you completely on the spot-

Michael Saloio:

Do you want me to take that first? I hired a leadership coach in 2016 for the first time after a conversation with Stephanie actually, which is a different story. And-

Daniel Stillman:

Did Stephanie give you some feedback?

Michael Saloio:

And one of the things that I realized about myself in trying to become an entrepreneur that I needed to improve upon was just having a plan and sticking to it. A lot of my challenges in the early days were, I had to define my own schedule. Sounds like really basic stuff, but going from an investment bank where there's pretty clear structure and a way of doing things, highly professional, and then having to wake up every day and figure it out, was that I had to really plan my week, like really relentlessly. And it came down to just doing what I said I was going to do. I have a much broader definition of what integrity is now. I became really obsessed with the... I still am very obsessed with the idea of integrity, but I wanted to build a culture where instead of it being based on hours and management, it was based on setting really clear values and goals and letting people self... I don't want to say self-identify, but letting them say what's possible for them.

Michael Saloio:

And then kind of challenging whether or not that was possible. And then holding them accountable to doing what they said they were going to do. But more than that, calling themselves out when they weren't going to do it. That seemed like a much better model to me than being scared or making them wrong for not doing something, you know?

Daniel Stillman:

Yeah.

Michael Saloio:

The way that we do things is on Monday, we have a meeting. It's a standup where we all say what we're going to do for the week. And then on Thursday we have a check-in where we're really honest about whether or not it's going to get done. And we give ourselves the opportunity to ask for help. And that's it, you know? And so instead of feeling like you have to hide or you have to be wrong for not having done something, it's like, "Hey, look, I said, I was going to do this thing and it's just not going to happen this week because these three things happened." So at least it opens up a conversation to, "Well, what do we have to do to actually get it done?"

Daniel Stillman:

Yeah. I'm watching you nod Stephanie. Say more.

Stephanie Golik:

Yeah. What I really loved about it, within our culture that I've started to see is like, it really is... culture is, you get what you recognize or what you praise, I think is the phrase. And it feels like we just really praise when people step up and say like, "Yeah, I said I was going to do that. And I didn't, and I'm not sure if it's still important." Just that level of honesty. Besides that, it's just like, I think a real bonding and humanizing thing to do for a team. It also just gets us back to performing. We move past the... there's a lot of effort in hiding and feeling crappy about not doing something, right? That's just effort that doesn't... we're just kind of trying to say, like, "It doesn't need to be there. We're all humans and we're all trying to do our best and build this thing together."

Michael Saloio:

Yeah. I love how you said it's a bonding experience too. It's a really bonding experience to just be honest about what's happening.

Daniel Stillman:

Mm.

Michael Saloio:

I also love what you said about the, it's like a tire with a slow leak. It's literally not working. I really think about integrity as something working, like a system working. It can be your human working, like being in alignment with which is actually authentic to you or what is actually authentic to you. But at the company level, it's the same thing. Where are the leaks? You know? And if you're always just focusing your attention on plugging the leaks, then the wheel's not turning, it's literally not working.

Daniel Stillman:

Yeah. It's interesting, like that Thursday meeting could feel like being ashamed. So I'm curious how-

Michael Saloio:

It could be.

Daniel Stillman:

Yeah. So like, how do you facilitate that to make sure that as you're saying, Stephanie, people feel... This maybe goes to Michael, your point of like, an energy producing partnership. There's that feeling of like, "Oh, I'm blocked," or, "I don't know if it's important anymore," or, "I need some help." What makes that conversation, that Thursday conversation, possible?

Michael Saloio:

Nothing is wrong. Something's not working.

Daniel Stillman:

Hmm.

Michael Saloio:

Hey, something's not working here. Okay, great. What's not working? Let's problem solve around what's not working and get it working.

Daniel Stillman:

Yeah.

Michael Saloio:

It's the elimination of something being right or wrong. To me, at least.

Daniel Stillman:

Yeah. Stephanie, do you want to say more about your nods?

Stephanie Golik:

I'm actually just agreeing. I was thinking if I had anything to add. I think that really is the core thing, is that it really is that removal of right and wrong in it. And we're all sort of working towards the same thing together, so it's acknowledgement of something that might not be working. I was also thinking of some of the... We actually frame our check-ins through a series of questions that we all sort of answer. And so I was thinking about some of those questions that we ask and whether they kind of also open up more of an opportunity for that.

Stephanie Golik:

We ask at the end of the week, things like, "What did you learn?" And sometimes that becomes an opening for people to also kind of open up about like, "Well, I learned that this wasn't working," or that this thing has changed. It's also that lens of like, we're constantly trying things. We're committing to trying things. And then figuring out what's working and kind of just being as transparent as possible about what we're learning along the way.

Daniel Stillman:

Yeah. Yeah. That's something I'm always curious about because in any good story, there's peaks and valleys, like as you say, like sometimes you hit a wall and something doesn't work. I'm curious how the two of you manage your relationship as co-founders, if you've dealt with friction between the two of you.

Stephanie Golik:

Yeah. I mean, well, I'll tell the story that Mike alluded to. Because I think it's [inaudible 00:21:25] story.

Michael Saloio:

It is.

Stephanie Golik:

So, this is before Mike and I were our co-founders. This is back when we were actually working at the first studio, our first working experience together. And we were considering hopping over to this other studio to continue working together. And I think this all comes back to the rawness, realness of that first conversation. Mike and I, I've already, at that point, I think gotten to the point where we were really honest with each other and I think that's really Mike's doing. Mike is very, very raw, very honest. Very direct. I'm less so, but I think he's taught me a little bit of that. And I felt like I could give him critical feedback.

Stephanie Golik:

And in that moment of deciding to continue to work together and move to this other venture together and take this risk, I felt like I could give him some feedback and we went for a walk in Soho and I gave him really direct feedback and we had a really great conversation that also was a prompt for Mike to also get into coaching and a couple other things, which was like... being really good at taking feedback is an incredible quality. And I think having that kind of experience early on in a working relationship where it goes okay.

Stephanie Golik:

You get feedback. It not just goes okay, but it actually really furthers your ability to work together. I think it set the stage for lots of versions of that conversation that have happened over the years, both ways. But you know, there's lots of working relationships where it's just not as easy to have an honest conversation about something that's, again, not working for you or making you feel a certain way and you end up holding it in, and/or doing other things to skirt around it that just don't get to the core problem because you don't have that level of kind of open dialogue. It feels like we established that open dialogue pretty early on, like long before becoming co-founders. So by the time that we got into this more deeper relationship and engagement, we had a lot of that foundation, which I think has been really helpful.

Daniel Stillman:

Yeah.

Michael Saloio:

Yeah. And yeah, I remember the feedback and it prompted me to enroll in leadership coaching. I wanted to improve. The feedback was very directly... It was basically, "Hey, I like these three things, but here's the one thing that I'm not okay with, and this is what I'm going to need to leave and go with you to this other shop." And I was just like, "Cool. I really appreciated it." And then I went and worked on it. I'm skating around it a little bit maybe, but it was around... I think a prior version of me, and still a little bit today, because it's hard to work past these things. I basically struggled to make choices. And so I wouldn't say my thing confidently or I wouldn't make a decision confidently and then something wouldn't be getting done and I would get angry and resentful that it wasn't getting done.

Michael Saloio:

And I realized that I was really struggling to make powerful choices and have confidence to just make decisions. And I was like, "Man, I really want to be able to make really powerful choices and stick to them even if they're wrong." Because I knew if I wasn't making that choice or if... let's say I wanted someone in the office to do something by a certain time and I wasn't asking for that and then I'd be resentful that it wasn't getting done. And so there wasn't just clear expectation setting. And I totally agree with everything that Steph said, or maybe not agree, but it certainly resonates that by the time we became co-founders, we had a way to have healthy conflict, basically.

Daniel Stillman:

Yeah.

Michael Saloio:

So yeah, there still is friction. I tell Steph this all the time, when we do have friction, I leave the room feeling better than having gone in it, which does lead to this concept of like, energy producing partnerships. You can have a partnership that has friction in it where the friction produces results and performance.

Daniel Stillman:

Yes.

Michael Saloio:

Or you can have a partnership where the friction produces something that I would call energy draining, where you leave the room a little bit confused or not feeling so good. And those are just more challenging. It's like a car that kind of constantly breaks down that you have to take to the shop. You want to be able to leave the shop cruising really fast, windows open, in Miami, wind blowing through your hair. You don't want to be taking the car to the shop all the time. And you know, then you get on the freeway and a tire blows out or something. I don't even have a car yet. I'm recently in the process of moving from New York to Miami, so my car analogies aren't that good. Yeah. You don't want to be in breakdown in the breakdown lane couple times a week. It's just too draining.

Daniel Stillman:

You know, I want to unpack a few layers because Stephanie, the feedback you gave to Michael, there's an implication here. One of my theses about conversations and relationships is, there's a conversation that we're all having with ourselves. And for you to be able to give him that very, very clear feedback of like, and to design the conversation, to say, "These are these things I like. This is what I don't like. And this is a blocker for me." To be able to express yourself clearly in that way does is non trivial, right? And that is the work. So we say it's energy producing, but you did put that energy in so that he could hear you.

Daniel Stillman:

Then he has to put the work in to say, "I'm willing to do something about that." And then what we have here is, there is an energy producing partnership because it becomes a flywheel, as you said, Michael. We're all putting energy in, but the energy creates forward motion, forward momentum. It creates feedback loops, right? It creates results. But not for nothing, doing that work on your own to say, "Here's what I want and what I need," and doing that work on your own, Michael like, "Okay, well I'm going to do something about this feedback." Those are conversations that you each had with yourselves that the other person can't help you with, necessarily. That's time you put in.

Stephanie Golik:

Yeah. I love that. It really is true. It is putting the energy on both sides that can produce that results. Because if it's missing on either end, there's effort that's needed. And I do think, to Mike's point around like, you keep having to take your car back to the shop or you keep going the shop. It can get draining. That's why it gets drained. Right? Because there is effort. And if it keeps happening or if it doesn't feel like you're coming out of it with a well working, like a significantly better working relationship, it is a draining thing. But yeah, it's work. It's work on yourself to receive feedback. It's work on yourself to learn how to give good feedback or to have those, be able to articulate those kinds of things.

Stephanie Golik:

I don't even remember how I originally articulated the feedback, but it was because we were thinking about this larger decision about changing jobs. It was something I was thinking about quite a bit. And felt this little nagging thing and felt like I was willing to put in the energy to figure it out. It felt there was something at the sort of heart level. That you want to make it work. And you're willing to put in that little bit effort to kind of dig in and figure out like, what is that feeling? How could I express it in a way that it might be constructive? And then, Mike of course did a lot of the effort on his end to take it and listen fully in the conversation, which is also hard.

Daniel Stillman:

But you also did that step of listening to yourself first.

Stephanie Golik:

Yeah, absolutely.

Daniel Stillman:

Which is nontrivial work of like, you know-

Stephanie Golik:

An interesting way to put it.

Daniel Stillman:

What am I feeling? You sensed something and you're like, "Wait, this is bothering me. What is it that's bothering me? Can I express it clearly?" I think it's sort of an ongoing joke that we want someone who can read our minds. And it's just obviously not a thing. That work of listening to ourselves and then the work to be able to express ourselves in a way that someone else can hear. And as you said, Michael, any hard conversation, we always feel better afterwards if we put the work in. And I think people, this happens all the time. We're like, "Oh my God, there's this hard conversation. I don't know what to do." It's like, well, if you face it and you sense into yourself and you do the work before the conversation, it's always going to be better after that conversation.

Michael Saloio:

Yeah. And if you express yourself authentically inside of the conversation. I like what you said about the flywheel and about putting energy in that actually creates more momentum on the other side of it. That's a really cool way to look at it.

Daniel Stillman:

Thank you. Yeah. I've been thinking about the... somebody talked about it in a recent interview.I did. I'm not remembering who now. They talked about Jim Collins' flywheel effect in Good to Great. And every company needs to have a flywheel, but I think people need to have flywheels. And clearly partnerships have to have flywheels too.

Stephanie Golik:

Yeah. It reminds me too of something that Mike and I talk a lot about, which is just the understated importance of like, just commitment, which is like, in some places, a dirty word. But truly just committing to the thing together. I think it does. It allows you to kind of push through some of those more energy draining moments or put in the extra energy to figure it out. It's sort of like marriage.

Daniel Stillman:

Yes, totally. Michael, what's coming up for you?

Michael Saloio:

Yeah. Oh, so what's coming up. So, what actually came up for me is, I was listening to different podcast earlier this year called Invest Like the Best, Patrick O'Shaughnessy. And he has an investor's field guide and the founder's field guide. And he has an episode with Mike Maples from Floodgate, who has just epic quotes on startup building. And one of the things he says is, "The future isn't something that happens to us like the weather. The future is what we decide to create." And I just couldn't agree more with that. And that really is a big way that I look at commitment too. There's so much emphasis in the startup ecosystem about testing and ideating and seeing what works and what doesn't work, which is clearly very important.

Michael Saloio:

And also you have to choose to do the thing and really choose it. I think there's too much emphasis on ideating. The way that I look at entrepreneurship is like, I just know what I want to make. And I'm pretty ruthless about making it. In my head, it's already done. Because why not take that lens? Does that mean it's necessarily going to work? No. I don't know it's going to work. Maybe that's where the testing and ideating comes in. But in my head, Huddle is built. It's already done, you know? And like, I don't think that's arrogant. I think it's, I have to choose that lens. I have to choose to be that confident about it. Because I don't know if it's going to work, anyway. Right? Like when you commit to something, you don't know that it's going to work, but you have to commit to it, because then once you commit, we have no idea what's on the other side of our choices and our commitments. We think we do.

Daniel Stillman:

Well, I mean, it obviously works on the team to team, like, project to project basis. Right? It's the question of like, what does it look like at scale? Which is always an interesting question.

Michael Saloio:

Yeah. But my choice to get up every day and just choose that this is what I'm doing, and I see what it looks like in the future and I'm going to take steps today to build it. And I'm really committed to it. The question as to like, what should I do or how should I do it, it kind of melts away. It's just consistent action towards the goal. I hope that lands.

Daniel Stillman:

Yeah, it does. Well, I mean, it also sounds like that's something that you've worked on you. From what Stephanie, you were saying earlier. I think, Michael, you've struggled with what I think a lot of us struggle with, which is optionality. Right? Making a decision and choosing to build one thing and not another is always hard.

Michael Saloio:

Yeah. I've spent a lot of time not committing to things staying on the outside of things.

Daniel Stillman:

Did I read that right?

Michael Saloio:

Yeah. Completely. I spent a lot of time trying to find the "right thing."

Daniel Stillman:

Yeah.

Michael Saloio:

Which is a cop out for taking responsibility for the thing that you really want to do.

Daniel Stillman:

Yeah.

Michael Saloio:

At least for me-

Daniel Stillman:

And that goes back to integrity, basically like, what do I really-

Michael Saloio:

Yeah. Yeah, exactly. I should have said that like from I. I shouldn't have said you.

Daniel Stillman:

But no, it's all good.

Michael Saloio:

I ultimately have to do the thing that I really want to do.

Daniel Stillman:

Yeah. Well, and that's the point of the thing. So, we're coming close to the end of our time together. There was one other topic I did want to make sure that we hit upon, which is failures. Because we're talking about what I like to call a bucket of puppies. Everyone loves a bucket of puppies. If you've ever seen a bucket of puppies, it's adorable. And you two have a positive flywheel and an energy producing partnership and open communication. And I suppose we could just like, everyone could just take this podcast and just listen to it backwards slash inverted and say like, "These are the lessons. If you notice these things, leave the partnership right away, or don't start a company with them." But you know, Michael, you did talk about lessons from failures and you know, when it comes to being a conscious co-founder and intentional, co-founder, I'm wondering if the two of you have any anti patterns from your own experience. Things I did in the past that didn't work include blank.

Michael Saloio:

Oh yeah, I do. So, I-

Daniel Stillman:

Wait, hold a second before that. Because Stephanie, I want to check in with Stephanie first because I think she had something.

Stephanie Golik:

Honestly, the only thing that comes to mind, I mean, there are definitely many, but the one that comes to mind for me, that's definitely very partnership oriented is really that this is a true for me statement that may not be true for everyone. But that going it alone doesn't work for me. Going out and trying... I'm a very... I don't know. I am a builder. I feel like I can go off and kind of build what I want to build or do this idea that I want to do. And in the past, that's led me to just kind of take on a project or an idea solo and try to just be the person that makes it happen on my own.

Stephanie Golik:

There's been a number of little heartbreaks along the way with that, with things that didn't fully, really, really get off the ground, really get a chance. And I think that having a real co-founder partnership has been a real learning for me in why the co-founder route is the route most taken. Because really, that level of partnership, and that level of commitment on both ends, I think it's really, really important to actually getting hard stuff done.

Daniel Stillman:

That's really good advice. I think going it alone is tempting.

Stephanie Golik:

It is tempting for some more than others. For me, it was very tempting and I did it multiple times. And here I am. I probably wouldn't do it again, honestly.

Daniel Stillman:

Yeah. Thank you. Michael, what was on your mind?

Michael Saloio:

Did you say anti patterns?

Daniel Stillman:

Yeah. When we talk about lessons from failures or partnership, Stephanie's giving us a like, "Don't even try to not do a partnership," which is an anti, anti, anti pattern, I think.

Michael Saloio:

Got it. Well, my anti patterns. I think I relate to them more as failures, but positive failures.

Daniel Stillman:

Positive failures.

Michael Saloio:

I had many a partner. They were all super high performing, quality human beings. And many of those partnerships had either mediocre results or were just failures. They didn't work out. And everyone went off to do amazing things afterwards. But what I learned from me is that I would often enter the relationship being really inauthentic about what I wanted. I joined two different businesses as like a minority partner. And what I really wanted was to be the CEO or be the co-founder. And I wasn't super real about that at the time.

Michael Saloio:

I had to go through those things to learn that about me as well. But those are my learning lessons, is that enter the partnership and be like really raw about what you really want out of it. And that's something I think Stephanie and I did really, really well too. Because I was going to go it alone for a hot minute. Because I was like, "Yo, I don't know if I can do this again. I just keep trying out these things and they're just not working out." And so yeah, I was tempted to go it alone too. But we have the ability, based probably stemming from that initial conversation and many conversations like it, where we can just be really super truthful about what what we wanted.

Daniel Stillman:

Yes.

Michael Saloio:

Yeah. Honestly creates a lot of trust. Right? It's pretty simple. It's harder to do in practice, but.

Daniel Stillman:

Yeah.

Michael Saloio:

Yeah. I wouldn't say the fatal flaws of any of these failures was any one particular thing other than just an inauthenticity about... I'll just speak for myself, what I wanted out of that relationship. But I think if you talk to some of my ex partners, they'd say similar things.

Daniel Stillman:

Yeah.

Michael Saloio:

Yeah.

Daniel Stillman:

That's really beautiful. And I forget what it comes down to-

Michael Saloio:

Or who knows what they'd say?

Daniel Stillman:

Well, I mean, it comes down to... in a way, Michael, what you and Stephanie are saying is very similar. It's like, if you want to be in a partnership, you have to know why. You have to know what you want and what you want from the other person. And to be really clear and direct about that, which is pretty much what we've been saying this whole time. We should call scene very soon. What haven't I asked you about partnerships that I should be asking you? What haven't I asked that I ought to have asked?

Michael Saloio:

I don't know if this is something you should ask, and I hate to give advice, but I think generally speaking, and I wrote a blog post on this, it's called You Don't Need a Co-founder, which is so funny because we're sitting here saying that co-founders are amazing. But what I meant by that, I meant a couple things by that. One is, what you really need is people around you. The relationships can take a lot of different shapes or forms. I had some kind of shotgun co-founder wedding type vibes as well. I would just say go slow. It takes a lot of time to understand whether or not you're going to be able to build a company for... Just think about how much time you spend working.

Michael Saloio:

You're going to go into something with someone that might take seven years or 10 years or longer, if you keep going with it. Right? So it takes a long time to understand whether or not you're going to have healthy conflict resolution or whether your skill sets are matched. Right? Another thing we haven't talked about is like, Stephanie is a designer and builder, I'm an ex finance guy who's kind of good at sales and business development and vision. And we're both actually really, really visionary people. But we have the ability to actually make things together. There's a skill match as well. And also our company works with founders, right? So we see a ton of partnerships. So, I guess two things. If you're going to go into work together on something, you got to make sure that you have complimentary skill sets, which is very basic. But two is like, go slow. Get to know somebody. Go into battle with people that you know how to work with.

Daniel Stillman:

Yeah. Totally. Any closing thoughts from you, Stephanie?

Stephanie Golik:

Yeah. I think I agree with all of that. Yeah. My recommendation or thought would be that like, if you can, work with, partner with someone that you've known and you have some of that kind of just normal relationship stuff in place with. Because it's still two human beings that are in a relationship, it just happens to be around co-founding a business together. But there's a lot that's just relationships stuff. So having that, I think you have a little bit of a head start. But at the very least, starting out with those open, as open, raw, and authentic of conversations as possible about things that are sticky and uncomfortable, like commitment. Even if it is that today, the commitment isn't fully this or that, I think is really, really important. A lot of people skirt around that stuff and then someone's committing more and it just starts to become more complicated than it's worth. So, I think the authenticity just happening as early on as possible is really important.

Daniel Stillman:

I love it. Well, you two. Thank you so much for being in a huddle with me today. If people want to know more about Huddle or the two of you, where in the internets should they go to learn more about the things that you all are...

Stephanie Golik:

You should head to huddle.works.

Daniel Stillman:

Especially if you are a early stage founder who needs something really, really powerful built. If I understand correctly.

Stephanie Golik:

Absolutely.

Daniel Stillman:

And Michael, you and I have talked about this, you need more people in the Huddle too, right? Lead designers and creative strategy people and those types of folks as well.

Michael Saloio:

Yeah. Ultimately, we're building a really high end, high quality builder community. So, we have a lot of people who are ex high growth tech company, ex founders, ex product leader at a FANG, or-

Daniel Stillman:

A MANG, I think we call it now.

Michael Saloio:

Ex agency executives, and we're making it really easy for them to build independent careers inside of Huddle by connecting them with really amazing startups that just desperately need their help.

Daniel Stillman:

All right, y'all. Well, I will call scene. Thank you so much, you two. You two are awesome.

Michael Saloio:

Yes. Yeah.

Stephanie Golik:

You're awesome.

Michael Saloio:

Thank you for having us. And thank you. I've told you this many times but you are the best asker of questions I've ever met.

Stephanie Golik:

[inaudible 00:47:11].

Michael Saloio:

It was really a pleasure. It was just a really flowing conversation. I'm like, "Whoa, what just happened? How long have we been doing this?" But that was really fun. So, thanks for having us.

Daniel Stillman:

Oh, it's my pleasure. All right. Now I'm really going to stop recording.

Community Building for Founders through Conversation and Hosting

Today my guest is Yehong Zhu, the founder and CEO of Zette.

We discuss three key layers of conversation design: 

+ The conversation with yourself - even with so many companies founded…why not me?

+ The importance of community, community building and hosting as an integral part of staying sane, informed and productive as a founder.

+ The broader, cultural conversation - how does a founder design the conversation around why does this company matter? Shaping this narrative arc can help you connect your company’s mission to the mission of potential funders and advisors

Prior to starting Zette, she worked as a journalist at Forbes Magazine, where she reported on business, market and technology trends. She also worked as a product manager at Twitter on two consumer teams—the Tweets team in San Francisco and the Events team in London—where she shipped features on desktop, mobile web, iOS, and Android to 330M users globally. She graduated from Harvard College in 2018 with a degree in philosophy and government.

Be sure to check out my conversation with Michael Bervell about his “Conversation Onion” model that we reference in the conversation.

Links, Quotes, Notes, and Resources

Playing Nice with Paywalls

Zette

Minute 1

Yehong Zhu:

I've always believed that there are a lot of problems in the world to be solved. I think that, why not me? Right? Why not be the one to identify some of the issues in the world and work towards solving them, even if they're not previously solved issues, doesn't mean that they're impossible to do so. And so I think that there's a lot in the world that requires vision and creativity and courage to make it better or to at least make it more palatable. Right?

Minute 16

Yehong Zhu:

as nothing that could have prepared me for what was coming next, which was that I had to figure out how to recruit an entire team remotely and build a remote culture from nothing essentially, how to figure out how to fundraise entirely over Zoom. And how to get a network of warm introductions when the city that I had supposedly moved to, because it was at the genesis of Silicon Valley was completely a ghost town at the time. And so my tactic switched from meeting investors for coffee in coffee shops to badgering them on LinkedIn. You know what I mean?

A lot of the adaptations that I was forced to go through, I think ultimately made me a stronger founder, a more flexible, adaptable person, but it was not without tremendous growing pains. I think we all went through those, we can all think back to where we were two years ago when the pandemic first hit. I think it's particularly hard when you're just starting out, because it's not like you have an existing base of resources or an existing set of colleagues or co-workers or a network that you can lean on, because you're just at the beginning of your journey.

And so there's pros and cons of course, but I think one of the pros is perhaps ironically having such a difficult beginning gives you a better sense of preparedness for what's to come after. Right? If the beginning's not a cakewalk, you know that the whole journey itself is going to take a lot more than perhaps you would've thought, but it does prepare you to be a more resilient founder.

Minute 21

Yehong Zhu:

I think that one of the interesting side effects of living with other founders is that it makes you a better founder yourself. Because anytime you have a question around let's say, what's the right business strategy to employ here, or who are the best accounting firms to work with or what do certain investors or firms do for founders versus other investors? These are difficult questions to answer in a vacuum, right? You need information that's both accurate and relevant and recent and all of these things. And the internet is so full of different pieces of information that sometimes it's hard to know what to trust.

If you're struggling with fundraising, for example, you can try to figure out from reading blogs on medium from five years ago, if you're doing the right thing, or you can ask your friend who literally just raised around two months ago, what the actual environment is like right now. And so I think some of these connections and these networks that you meet in-person when you're actually friends with someone and they're able to be honest with their experiences, can help you so much more than if you were just trying to figure it out on your own.

Minute 29

Yehong Zhu:

If you're on a mission to do something that's greater than yourself, you can get a lot of people excited by the mission you're pursuing, because perhaps it's something that's equally important, if not more important to them, a lot of people care about democracy, right? A lot of people believe that reliable information, factual information journalism is the foundation of a strong and healthy democracy.

And so they get excited by people who are working on new ideas in this space, because maybe in another life they would've wanted to work on the same idea. Maybe they even had a similar idea and they're just glad that they're meeting somebody who's actually pursuing it. Right? And so I think there are a lot of ways to establish that connection with somebody. It depends on what they care about.

More About Yehong

Yehong Zhu is the founder and CEO of Zette. Prior to starting Zette, she worked as a journalist at Forbes Magazine, where she reported on business, market and technology trends. She also worked as a product manager at Twitter on two consumer teams—the Tweets team in San Francisco and the Events team in London—where she shipped features on desktop, mobile web, iOS, and Android to 330M users globally. She graduated from Harvard College in 2018 with a degree in philosophy and government.

Full Transcript

Daniel Stillman:

Well, then I will officially welcome you to The Conversation Factory, Yehong Zhu. Thank you for making the time today, working through all of the internet troubles that assail us eternally.

Yehong Zhu:

Yes, indeed.

Daniel Stillman:

Listen, I'm really glad that Michael put us together. I'm excited to peel back the layers of the conversation that you're having with yourself around the building of your company. And I'm wondering for folks who are listening, entrepreneurship is important to you. Why is that a value of yours and what made you want to start the company that you're helming right now?

Yehong Zhu:

I've always believed that there are a lot of problems in the world to be solved. I think that, why not me? Right? Why not be the one to identify some of the issues in the world and work towards solving them, even if they're not previously solved issues, doesn't mean that they're impossible to do so. And so I think that there's a lot in the world that requires vision and creativity and courage to make it better or to at least make it more palatable. Right? In my particular sector, the industry that I happen to care about is journalism.

Yehong Zhu:

My mother was a journalist before me, and I've always found it to be an incredible art form that also informs people, educates people and gets important stories out into the world. But it was an art form that was always struggling ever since the digital age at least with its business model, in terms of getting people to pay for and subscribe to reading online news has been tricky ever since the subscription model changed from being purely a print based one to a digital based one. And paywalls are now kind of abundant and it makes it really hard to decide what you should pay for, maybe inconvenient to remember how many subscriptions you have or hard to cancel, hard to keep track.

Yehong Zhu:

And so a lot of the issues that we face in not reading the news, I think comes from our inability to even access the right information at an affordable price. And so that was the problem that I saw in the market, and ever since I was young I was pretty resourceful, pretty entrepreneurial in a sense. When I didn't see certain clubs in my high school, I wanted to go found it myself. And when I was in college I wanted to start a college admissions consulting company, which I ended up doing to help underprivileged students get into universities.

Yehong Zhu:

And so I had this pattern in my earlier life of just going for the things that I wanted. And in this particular case I started Zette during a time of tremendous misinformation and the fake news crisis that Donald Trump called it. I think that it's a really important value and journey to be on, which is why I'm excited to be an entrepreneur in this space.

Daniel Stillman:

Does Zette take a position on what news people can access? How does curation come to bear on helping people find the things that they want, to eventually subscribe to?

Yehong Zhu:

Our first level of curation is really just figuring out who the paywall properties are. There's almost a self selection process there of, typically some of the higher let's say expense productions require paywalls. So journalistic outlets that employ newsrooms of journalists tend to have a harder paywall on their content in order to fund the journalism that they use. Whereas there's a lot of blogs and content sites and maybe let's say more clickbait websites out there that don't have strong subscriber base, because maybe their content isn't something that you would consistently pay to read, but rather you would find it on the internet as a free site and you would click on it there.

Yehong Zhu:

There's, I would say, firstly, a difference between the journalism that paywalls itself versus the information that doesn't have a paywall to start. And so looking at the journalism that does have paywalls, our next step is figuring out, who would want to work with us, right? How many of these publications can we partner with at a given time? For example, we might want to target an umbrella corporation with many, many titles instead of just a single title that's privately owned, just because it allows to give the scale of reach that we would want for our audience.

Yehong Zhu:

And so that's how we start filtering down to what editorial lenses are we promoting, but it's more so from a logistical perspective rather than through let's say dogmatic perspective.

Daniel Stillman:

Sure, sure. I really loved the three virtues or values, I guess you'd really say, that you outlined of vision, creativity and courage. I'm curious when you started thinking about this challenge, as we were saying before we started recording, I feel everything starts with an internal conversation. How long were you telling yourself this is a thing that needs to exist?

Yehong Zhu:

I think I first started thinking about this problem in 2016. At that time I was a business reporter for Forbes magazine. I noticed that a lot of the articles that I was writing had a lot of advertisements attached to the articles that were being published. Right? I publish an article, there'd be seven or 10 ads on the page. I remember asking my editor at the time, why are there so many ads on the page? Doesn't it make it hard to read the actual content of this article?

Yehong Zhu:

He mentioned that because Forbes was ad based at the time, it made sense to put more and more ads on a single page, just because each ad only brought in a tiny sliver of revenue, right? Pennies on the dollar. And so as a result more ads more revenue. And so I could already see the problem then, which is that more ads or at least filling the page with ads led to not so great of a user experience. And it also didn't lead to that much money, which meant that subscription revenue was an obvious next step, not just for Forbes, but for a lot of national publications at the time.

Yehong Zhu:

But then if you assume that a lot of publications will move towards subscription revenue and paywalls, that meant that everyone would start paywalling their content. Right? And that meant that for the average user, for the average reader, it's going to put them in a tough position because no one can buy everything, right? It's not like you can justify buying subscriptions to a hundred different sites because you're probably not even going to read all of those sites on even a monthly basis.

Yehong Zhu:

It's only the occasional time when you hit a paywall, when you realize I do want to read this article, but I might not actually want a subscription. So it also puts the publishers in a tragedy of the common position where they're fighting almost against each other for the next additional subscriber. When I think if you just put let's say a pay per view model in front of the consumer, what happens then is that you can actually give them more options. Right? It's like opening up an entire economy class of an airplane that previously only sold business class. Right? As a result more people would want to fly aka more people would want to read legitimate journalism.

Yehong Zhu:

I saw the issue a long time ago, but I naturally assumed, and this is a funny thing that I think a lot of entrepreneurs might assume, that if a problem is that obvious someone is probably already doing it or somebody will do it for [inaudible 00:08:06]. Right? And so at the time I remember thinking, oh yeah, well, someone's just going to sound Netflix for news or Spotify for news startup and I'll be the first user of it when it comes out in a couple months or next year. Right?

Yehong Zhu:

The funny thing is that four years passed. And by the time I was ready to jump into entrepreneurship again and rethinking about the problems in the world, this problem had still not been solved and I was still in a state of shock that it hadn't.

Daniel Stillman:

Why do you think that is? I'm curious. Why hasn't anybody else tried to solve this?

Yehong Zhu:

Well, I think that there have been some attempts previously, but I think that timing here is a large factor. Like I mentioned before at the time that I was writing for Forbes, Forbes itself had not gone under paywall yet. Right? It was still reported. And a lot of internet based media companies were free. They were giving out content for free. They were giving out content with apps. And paywalls were starting to become a thing, but they were nowhere near as prevalent as they are now.

Yehong Zhu:

I think the other issue is that increasingly I think media companies and a lot of companies worldwide are realizing that they need to figure out how to get that elusive millennial or gen Z consumer on board. Because if you think about the media industry at least in terms of historical customers, it was usually older generations that would buy print newspapers, who would then sign up to be digital subscribers online. Right?

Daniel Stillman:

Yes.

Yehong Zhu:

But in order to keep the bloodline of your business strong, you need to make sure to appeal to newer generations of users, right? Every single year. I think what newspapers are quickly realizing is that they don't have a good strategy for capturing a digital native audience that might not even know what The Economist is. Right? They might not even have a reading habit up front. And so increasingly it's becoming more and more important to start appealing to let's say the TikTok generation or the social media generation, and really convince an entirely new demographic of users to start paying for news for the first time.

Daniel Stillman:

That's the narrative and it makes sense to me. How does that play with the people that you need to bring on board, your subscriber partners?

Yehong Zhu:

I've been speaking with a lot of media companies, a lot of media executives, and I think that there is an awareness around this exact problem, around reaching new demographics, around figuring out more sustainable business models, but there's also a hesitancy, right? Because if you can recall, technology obliterated the existing models. And so there's sometimes a little bit of hesitancy to try new technological innovations, to worry about the onboarding cost of, is this going to cost me engineering time? Is it going to cost money? Is it going to work? Right?

Yehong Zhu:

So there's a bit of hesitancy there to try bold new ideas. And there's still grappling with changes in the industry. Right? And so a lot of journalists were laid off in the past couple of years, some outlets did tremendously well, like the New York Times, while a lot of local news outlets really struggled with their own business models and retaining their audiences. There's a huge berth in terms of the problems that newsrooms are struggling with. And in addition to that, there are things like the death of the cookie. Google's getting rid of third party data, which means that a lot of the important data elements of advertising are being done away with.

Yehong Zhu:

And so there's a lot that they need to already innovate on that end. Right? In terms of data and data privacy regulations, et cetera. And then with COVID and with newsrooms scrambling to adapt to remote first environments or figuring out what to report on that's super relevant, there's a lot of movement on the editorial side as well. And then finally I would say in the macro environment, a lot of newspapers are being bought up by hedge funds, right? Or ownership is being transferred at lightning speed right now. And so there's a lot of management changes on top of all the other changes that are going on in the industry.

Yehong Zhu:

It's not super straightforward for them to see, hey, we need to shift everything to this new model right now. But I think with time there's going to be increasing recognition that innovation needs to happen and it needs to happen sooner rather than later.

Daniel Stillman:

It's interesting when we were talking, when I did my interview with our mutual friend, Michael, we talked about these three levels of conversation, these concentric circles. I think he thought of it as an onion. And there is that self conversation. We manage ourselves and we coach ourselves and then there's conversations with others, didactic, multiple team conversations, and then further and further out there's conversations with community and culture. What I'm hearing as you're talking about some of the challenges with Zette is, some of these bigger conversations where there's a lot of chaos or uncertainty at the macro level.

Daniel Stillman:

But I'm also curious as you're building this company, what's going on at the you level and also at the team level? I know that you were saying you're a solo founder, but nobody builds anything 100% by themselves. What you talked about in our pre-conversation, talking about trials and tribulations. I'm curious, there's definitely some turbulence at that macro level and I'm wondering what's going on at the micro and the meso level trials and tribulations with building this company?

Yehong Zhu:

I think that there have been a tremendous amount of obstacles and adversity when I was first starting to build Zette. And even now I think that the obstacles don't go away, they just change in form and function. In the beginning I remember I was so optimistic about starting a company, this was in February, 2020, right? Where we were the top of a-

Daniel Stillman:

That's just the punchline, way too many, there's so many stories that start. It was February 2020. Oh boy.

Yehong Zhu:

Imagine how I felt starting a month later. But I was freshly off of quitting my job at Twitter, where I used to be a product manager. I was full of this naive optimism about this startup being the greatest thing and I would move back to San Francisco so I could recruit engineers in-person. And I would attend these media conferences to get to know people. So I had booked all of these flights in advance. On a personal level I was in a long term relationship. So I knew I needed that stability on the personal front to take a huge professional risk.

Yehong Zhu:

And in a sense all of that came crumbling down, because San Francisco was one of the first cities in America to go through a complete lockdown. Right? And so within barely a month of starting to research about the company and figuring out the industry dynamics and starting some of those recruiting conversations, the whole world just flipped upside down on its head and all the playbooks that I had read on how to raise money and how to recruit people, of course were written for pre COVID world.

Yehong Zhu:

And so there was nothing that could have prepared me for what was coming next, which was that I had to figure out how to recruit an entire team remotely and build a remote culture from nothing essentially, how to figure out how to fundraise entirely over Zoom. And how to get a network of warm introductions when the city that I had supposedly moved to, because it was at the genesis of Silicon Valley was completely a ghost town at the time. And so my tactic switched from meeting investors for coffee in coffee shops to badgering them on LinkedIn. You know what I mean?

Yehong Zhu:

A lot of the adaptations that I was forced to go through, I think ultimately made me a stronger founder, a more flexible, adaptable person, but it was not without tremendous growing pains. I think we all went through those, we can all think back to where we were two years ago when the pandemic first hit. I think it's particularly hard when you're just starting out, because it's not like you have an existing base of resources or an existing set of colleagues or co-workers or a network that you can lean on, because you're just at the beginning of your journey.

Yehong Zhu:

And so there's pros and cons of course, but I think one of the pros is perhaps ironically having such a difficult beginning gives you a better sense of preparedness for what's to come after. Right? If the beginning's not a cake walk, you know that the whole journey itself is going to take a lot more than perhaps you would've thought, but it does prepare you to be a more resilient founder. And if you can start a company during a pandemic, you can probably do anything. That's my sense.

Daniel Stillman:

Yeah. Well, let's talk about what that process was like, badgering VCs on LinkedIn doesn't sound like that much fun. Was it effective?

Yehong Zhu:

I think it depends on how you go about it. There's definitely methods to the madness. I think that I learned a lot about the value of form introductions and going through people that I had previously known or worked for. I also tried to make new friends and new connections through unconventional means. For example, I wrote an article about what it was like to start a company during COVID and it went viral. And through that virality, I was able to be connected with other founders and investors who read my work and resonated with what I was building.

Yehong Zhu:

And so that's a way that you can make connections at scale rather than going one by one. And then I would join these other communities that were relevant to me. So for example, I would find networks of female founders, and then I would sign up for these mentorship calls or these listicles where everybody who wanted to connect with other founders would write down their names and put down their social media. And so I would go through one by one and reach out and just ask for a call or ask for a conversation or some advice.

Yehong Zhu:

And I found that, not all these conversations were helpful, but for the ones who were helpful, I ended up making very close friends with other founders who were also struggling to find community, who were also struggling to find their bearings. And then eventually I moved from the online world to the offline world. So having met a lot of interesting, cool people through different means online, I started some founder group houses where I would actually live and work with these founders in different cities.

Yehong Zhu:

I started a female founder house in Maui, and then another one in Mexico. And through these networks I was able to actually start meeting new friends and colleagues in-person, as opposed to only being in the basement of whatever apartment I was renting in San Francisco.

Daniel Stillman:

What I'm hearing you say, these are such universal challenges of how to go from a cool introduction to a warm introduction. And one of the things I'm hearing you say is, start with warm introductions. There's a lot of strength in warm introductions. The other thing that I'm hearing you say, which I agree with wholeheartedly, is that, creating your own opportunities to connect with people at various levels of scale is important.

Daniel Stillman:

As you said, like communities, but also on the smaller scale, these houses where there's not just communities that are diffuse and on the internet, but grounded in a place and a space and being the host of those communities is a really, really powerful approach to building deeper connection.

Yehong Zhu:

Yeah, definitely. Because as much as we can build community online, we are physical creatures that exist in physical spaces. And I think the great tragedy of social distancing is that it's exactly that you're distanced from the social connections and warmth that you need, right? To live on, to build cultures, to build community with. And so as much as the world is now remote, I think that there is an imperative value of being in-person or at least of having the in-person connection with your team, with your family, with your friends, with your colleagues, that you should strive to maintain even as the world is crumbling around you, because that is the thing will keep you sane.

Daniel Stillman:

I'm curious, did these group houses in this community building effort, what's the narrative you tell yourself about the signs and signals you're seeing that it is effective? Because I think there's on one level it's just as you said, it keeps you sane and human connection is just purely essential. But then there's the flip side which is, is it giving you business results that you're looking for?

Yehong Zhu:

I think that one of the interesting side effects of living with other founders is that it makes you a better founder yourself. Because anytime you have a question around let's say, what's the right business strategy to employ here, or who are the best accounting firms to work with or what do certain investors or firms do for founders versus other investors? These are difficult questions to answer in a vacuum, right? You need information that's both accurate and relevant and recent and all of these things. And the internet is so full of different pieces of information that sometimes it's hard to know what to trust.

Yehong Zhu:

If you're struggling with fundraising, for example, you can try to figure out from reading blogs on medium from five years ago, if you're doing the right thing, or you can ask your friend who literally just raised around two months ago, what the actual environment is like right now. And so I think some of these connections and these networks that you meet in-person when you're actually friends with someone and they're able to be honest with their experiences, can help you so much more than if you were just trying to figure it out on your own.

Daniel Stillman:

I think this is so true and so important, and it's a very powerful way to resource yourself. I think my pushback is, creating community with your peers is essential. But the question that I'm sitting with is, you were talking about badgering VCs on LinkedIn, that doesn't seem, I'm guessing that wasn't a super effective strategy. Community building and networking with people outside of our peers or near peers or affinity groups is really challenging.

Daniel Stillman:

I'm curious what you found has been helpful, because you're talking about connecting with people like engineering resources, accounting resources, fundraising. How have you found building your network with those groups that are not your direct peers has worked for you?

Yehong Zhu:

It's a good question. And just a quick caveat, it is surprisingly more effective than you think to badger VCs on LinkedIn because their job is to talk to peers.

Daniel Stillman:

Fair.

Yehong Zhu:

I think depending on why you're badgering them and what the messaging is around speaking with them, they're actually very receptive to taking conversations because that's what they're getting paid for. Right? Their job is to introduce deal flow into their firms. That's just a quick side note. It's an excellent question. I think that there's, when I was at Twitter I learned that there's three types of management. You have to manage up, you have to manage down and then you have to manage around you. Right?

Yehong Zhu:

So comfort talking with superiors and decision makers, comfort talking to the people that you're working with on your team who are more junior than you, maybe even mentoring the folks who are more junior and then comfort with your own peer group, right? And the folks, your equals. I think all three are critically important to your success, because at the end of the day they're all going to be part of who you are as a leader and as a manager.

Yehong Zhu:

And in terms of how that functions, I think on a founder level, your team, right? Is going to be the folks that you work with and work together with and collaborate with and figure out, okay, how do we actually move this enormous problem forward? Whereas other founders from different teams, different industries, they're more of your contemporaries, your peer group, right? That's the folks that you are at a similar stage with, that you can learn from and with and together.

Yehong Zhu:

And then the folks who are ahead of you, or maybe in positions of influence, but maybe tangential to what you do, for example, investors or later stage founders who maybe are in your same industry or in your same vertical, or perhaps can act as mentors, are also extremely important folks to know, to have in your network. And in terms of how you meet them, I think there's a variety of ways, warm intros, cold outreach, going to events and speaking to the speakers afterwards, getting connected to people that you know, asking investors who have invested in you to open up their rolodexes to introduce you to the right folks.

Yehong Zhu:

I think these are all targeted strategic ways to develop a relationship or at least get that first meeting. And then in terms of how you actually develop a relationship, I think to some extent it has to happen organically, right? People are really busy, especially important people, right? And so they're not going to have time to mentor everybody that they need or take every meeting that is asked of them. And so making sure that you explain your relevance or what that relationship is going to get for both of you is often a good sign.

Yehong Zhu:

So for example, if you're starting an advisory board and you want to hire someone as a potential advisor, that could be a beneficial relationship for both sides, both someone looking to be on a board and for you yourself looking for expertise at a higher level. And so I think that's a little bit of, from my experience, building connections with folks that I'm not directly in touch with, but of course there's so much more that I could learn, more from other founders and entrepreneurs who can do this a lot better.

Daniel Stillman:

This is really, what this is bringing up for me is, there's this systemic approach to as you said, diversifying the nodes in your network strategically. Right? So being cognizant, it sounds like you were very intentional about building out as you said the up, down and around components of your network. And it seems like there's still this need at the conversational, the conversation by conversation level to be fully present and the ability to actually connect and invite someone into a deeper conversation.

Daniel Stillman:

There's no substitute for, it's like you've caught the fish, the fish is on the line and now what do you do? Right? And so I'm curious, A, if that resonates for you, and B how you feel you in the moment, in the conversation create that affinity and that desire for them to really go a little bit deeper with you.

Yehong Zhu:

It's a great question. I think that for me, a lot of the times it depends on how you communicate your mission, right? If you're on a mission to do something that's greater than yourself, you can get a lot of people excited by the mission you're pursuing, because perhaps it's something that's equally important, if not more important to them, a lot of people care about democracy, right? A lot of people believe that reliable information, factual information journalism is the foundation of a strong and healthy democracy.

Yehong Zhu:

And so they get excited by people who are working on new ideas in this space, because maybe in another life they would've wanted to work on the same idea. Maybe they even had a similar idea and they're just glad that they're meeting somebody who's actually pursuing it. Right? And so I think there are a lot of ways to establish that connection with somebody. It depends on what they care about. Sometimes in my case, if there's affinity around being a female founder, being an Asian founder, right? Or being a founder who's a solo founder, building a remote team, there's all sorts of ways that you can connect with other entrepreneurs, other investors, other people who will help you on your journey.

Yehong Zhu:

And just finding where your relationship overlaps, the similarities that you can connect to often strengthens that bond. For example, I think alumni networks are a good example of this, where no matter what school you went to, there's probably some really impressive alumni from your university. And if you reach out on a basis of that alumni connection, there's always that connection that you can lean back on. Right? And of course that's only going to open the door for you if they are receptive to that. But after that when they get to know you a little bit more, I think that there's different ways that you can connect further based off of that.

Daniel Stillman:

It's interesting, in a way I'm going back to looking at my visual notes, the seed of entrepreneurship for you is vision, creativity and courage. And it seems like the foundation of being able to connect with someone else can stem from as you say, communicating your mission, but also connecting to their purpose.

Yehong Zhu:

Yup. Definitely.

Daniel Stillman:

I don't think there's any substitute for, as you say, empathy and curiosity for the person on the other side connecting your mission to their mission and their purpose.

Yehong Zhu:

Agreed. I think that connection is so important because you have to ask yourself like, why do we wake up every morning? Right? What is it that we want to do with our lives? Or what is it that we want to do in the world? And I often hear that talking to founders is very inspiring, because these are the people crazy enough to think that they can change a seemingly impossible or immovable problem. Right? That's so big that it feels bigger than ourselves, that it feels like maybe this is just how the world has always been and always will be.

Yehong Zhu:

But I tend to see the world as a changeable thing. Right? The universe is not fixed. It's moveable. It might take a lot of time and effort and money to move some parts of it, but that doesn't mean that every single part of the world wasn't just built by people like us. Right? And can't be [inaudible 00:32:33] to be better and stronger and faster. Right? And so I think maybe that fundamental philosophy is what differentiates founders from everybody else.

Daniel Stillman:

Yeah. I'm always cautious about quoting Steve Jobs because, let's admit it, he was a bit of a jerk. But he did point out and I think rightly so that everything in the world was made by someone. Right? In one sense everything around us is natural and another sense everything is, because we're natural in some sense, but we have created all the systems around us and the people who came before us were just like us, which means we can make new systems if we choose to. There is that reality distortion field, that infamous reality distortion field around Mr. Jobs that made this possible.

Daniel Stillman:

I guess I'm curious, going way back towards the beginning of our conversation, you talked about that enthusiasm and that energy. I feel with every creative conversation, there's energy at the beginning and there's a dip somewhere in the middle. I'm curious, did you experience a dip and how did you pull yourself through your dip?

Yehong Zhu:

Are you talking about a dip in stamina through the startup journey?

Daniel Stillman:

Yeah. When I think about the startup journey, there are, I imagine many dips, from fundraising dips to team building dips, to dips in your own faith, in that reality distortion.

Yehong Zhu:

For sure. I think there's always going to be setbacks and disappointments and people telling you no or people telling you that it's not possible. But I think that what keeps you going, or at least what keeps me going is the sense that this is such an obvious solution, is that if you can just get to market, everything will work. And maybe that's not necessarily true, but it becomes a self-fulfilling prophecy. Right? You start reframing dips as clearing the way for people who are your supporters to find you, right?

Yehong Zhu:

It's almost like if fundraising or hiring even is a numbers game and every 10 people you approach will say no, but that means that one out of the 11 or 10 will say yes, then every no becomes a celebration because you just cleared the way for someone who wouldn't support you anyway, to getting closer to finding somebody who would. I think that mindset is really, really important. And it's gotten me out of more than just a few dips, let's say. Because it ended up coming true.

Yehong Zhu:

I think that after a while, when you stop taking rejection so personally, and when you accept the fact that you're not a multimillion dollar corporation or multi-billion dollar corporation with infinite resources at your fingertips, it's going to be hard to figure out how to do the same things on a faster timeline. But if you're nimble, if you're quick, if you can pick yourself up and dust yourself off faster than your competitors, there's nothing stopping you from just keeping, making progress and continuing to rise.

Daniel Stillman:

I appreciate that. I think that's true. And it's also hard to coach yourself through those dips. Right? Because while it is true that every no gets you closer to the law of large numbers through to the yes. In that moment it can be really just authentically sad to get the no that you were hoping for a yes.

Yehong Zhu:

It's true. I think that there have been many times when I've doubted after getting the 10th no or something like that. Like, wow, is this really an idea worth pursuing? Is my vision really an actually good one to do? Is this is something that I've just made some horrible miscalculation on? But I think the beauty comes because you're never, if you just try, if you honestly try and give it your absolute best shot, it's very rare that you only ever get negative feedback.

Yehong Zhu:

Sometimes it happens because you get unlucky. Sometimes you'll flip a coin 10 times and get 10 tails. Right? Sometimes that just happens, but it's just rare that you're not going to get a single glimmer of positive feedback or hope or somebody helping you or somebody saying, hey, don't worry about that, that's usually how the process works. Let me introduce to somebody else. Right?

Yehong Zhu:

And so I think the intermittent reinforcement of getting that occasional head every few misses and then getting better at tossing a coin, I think that's what really differentiate entrepreneurs who are able to go the distance. They see every sliver of hope as a triumph. And so that's the thing that keeps them going for the next triumph and the next one and the next one after that.

Daniel Stillman:

I think that's really beautiful. It's also clear, going back to the importance of having a community of peers, because when, and I've certainly found this in my own experience, when my own inner coaching fails, right? There's my peers to absorb some of the negative feelings and also to provide positive encouragement, that community is invaluable in those moments of those dips.

Yehong Zhu:

Yeah, definitely. I would say your community is valuable. Your team is just as valuable if not more, because your team, these are the people that chose to give their time, give their energy, give their lives to work on the same mission that drives you, right? Because they resonate with it, because they believe in it and they'll be there for you on the days where you think, oh my gosh, this is the worst day of my life, right? So you can go back to your team and remind yourself why you're doing this and why they're doing this and then move forward together.

Yehong Zhu:

And at the end of the day you only really need one person to believe in you. And fortunately that one person can be yourself, right? If you just have somebody believing that it's going to work out, that's all you need to take yourself up again and then keep going the next day.

Daniel Stillman:

Right. It's one person at one time. So at one moment it could be you and at another moment it can be your mom and in another moment it can be your coach, and another moment it can be your friend.

Yehong Zhu:

Exactly.

Daniel Stillman:

It's just like, I'm envisioning a relay race of reality distortion, that as long as somebody is willing to keep the energy going, we'll keep moving.

Yehong Zhu:

Keep the faith.

Daniel Stillman:

Keep the faith and keep it moving forward.

Yehong Zhu:

Definitely.

Daniel Stillman:

Listen, we're getting close to the end of our time here. I really appreciate us getting to this point in the conversation. What haven't I asked you about that I should be asking you about when it comes to the entrepreneurship journey, and as you say, overcoming managing, writing the wave of these trials and tribulations on the entrepreneurship journey?

Yehong Zhu:

I would say that it's important to ask about your why. I remember I spoke to Biz Stone once, he's one of the co-founders of Twitter, and he told me that everything takes 10 years. Every overnight success you see, it's not really overnight, right? You've got to be able to be in the trenches for 10 years in order to really see the fruits of your labor blossom into something that you would've never previously thought possible. And so you've got to have a really strong why for why you're doing this thing that you're doing and why you're going to be able to go the distance.

Yehong Zhu:

You've got to assume that on the worst days that you have when you're being beaten down by the entire world, why are you going to get back up again? What's that thing that's driving you towards it, or are you even going to get back up? Right? And it's not an easy job, right? If you wanted an easy job you would work as literally anything else besides being a startup founder. Right? And so understanding that upfront and knowing that's the cost of what this journey requires, I think is the most fundamental first step.

Yehong Zhu:

And if you're not willing to pay that price, and if you don't have a strong why, I would not encourage you to start a company. I would say, do something else, do anything else, and don't get into the arena until you're sure that this is the thing that you want to pursue.

Daniel Stillman:

This has really come up at a lot of different aspects. You mentioned vision very early on and the ability to connect with other people outside of your network through communicating your mission. This example with Biz Stone is so interesting. The importance of knowing your why to keep yourself going is really, really profound and very, very helpful, I think for anybody listening.

Yehong Zhu:

Thank you.

Daniel Stillman:

The every overnight success takes 10 years, people really, really forget this. The example I always cite. I remember this is going back a long time. One of my first jobs out of design school was working as a researcher and a strategist in the consumer electronics world. People would come in and they wanted to be the iPod. This is how long ago it was, Yehong. They were like, we want to be the iPod of blank. It's like they were printers, they were a dishwasher company, whatever it was. They were like, we want to be the iPod of blank. Because the iPod was the cash cow of Apple back then.

Daniel Stillman:

This was literally the cusp of the iPhone. I dug up this chart and I'm clearly going to have to dig it up again, that showed the iPod sales year on year. This is exactly what I said to them. I was like, you'd like to be a 10 year overnight success? Because the iPod was not immediately successful. When it first came out people were like, this is useless. It doesn't do half the things that the other MP3 players do, and it doesn't even have iTunes. All of the things in iPod was that made it a blockbuster took years and years and years to do. They plugged away at it for ages and nobody cared in the beginning.

Yehong Zhu:

Yep, definitely.

Daniel Stillman:

I think it's a great reminder. Biz Stone is 100% right, that we really should all be taking a long view and making sure we're anchoring ourselves to our why, and not just our why, but our vision and our mission. Right? Those are all part of the same flavor, but I feel they are slightly different flavors of one thing, which is having a core.

Yehong Zhu:

Definitely. You need to build up your foundation. Because I think the reason why why is a harder answer than how, is because there's an answer for every how, right? You can figure out how to incorporate a company. You can figure out how to hire a marketer. You can figure out how to get the right statistics that you're tracking for your analytics. All of these hows are actually already answered questions, and every big unanswered how is just a series of smaller answers.

Yehong Zhu:

But the why is something that only you can know, right? The reason behind why you would try such a crazy thing is so personal. Right? And that's the thing that actually drives everything else. And so if you can answer that, I think everything else can follow much more easily.

Daniel Stillman:

I think you're in very good company with that sentiment, by the way. Viktor Frankl quotes anicca when he says, and we have to forgive Viktor Frankl because anicca I guess really at the time, because they like many quotes, famous quotes, they just say a man. They meant, I presume I hope they meant all people. We could retranslate and say a person with a why can endure anyhow. The deeper connection we have to our core purpose we're willing to find anyhow, the how that we can find, and we're willing to endure even a difficult how.

Yehong Zhu:

Agreed. I think that quote is so on point and so important to remember, especially in these pandemic times, right? Where sometimes it feels like the whole world is crashing around us. I think it's important to realize that this too will pass. Right? But you need to have a strong core of what you're holding onto in order to survive the most turbulent storms.

Daniel Stillman:

I concur. Yehong, where should people go on the internet to learn more about you and your company, if we can direct them to other places?

Yehong Zhu:

Zette.com. That's zette.com, or they can just Google our name. Fortunately we have some pretty good SEO and hopefully our social media will pop up as well.

Daniel Stillman:

Awesome. That's really helpful. Your mission of letting people find and connect to the things that they really want to read and to create a sustainable financial model for it is a really, really awesome one. I'm grateful for you taking the time to unpack these layers of conversation in your work and life.

Yehong Zhu:

Thank you. Thank you for having me on. I think that you're asking exactly the right questions and I hope that some of our listeners will find this conversation helpful as well.

Daniel Stillman:

Thank you very much. We'll call a scene.

Clarity and Intimacy in Co-Founder Conversations

In this conversation, I dive into the nuances of co-founder relationships with Clarity.so co-founders Richie Bonilla, CEO and Eni Jaupi, CTO.

Clarity.so is a y-combinator funded startup that has built a groundbreaking DAO contribution platform. DAO stands for Decentralized, Autonomous Organization, which you should totally google if you want to know more. 

While Clarity isn’t a DAO, you can see how the radical transparency that is at the heart and spirit of the cryptocurrency movement is also at the core of Richie and Eni’s relationship. I mean, it’s also the name of the company!

Like a few of the other conscious co-founder interviews I’ve been doing, these two co-founders prototyped their working relationship before jumping into their company together, which helped them build a foundation of trust and respect.

They also talked a lot. Like A LOT before even starting the company. Starting with a few times a week, they gradually transitioned to talking for at least an hour, daily, for a year.

What this conversation re-established for me was that it’s important to have agenda-ed conversations, and it’s also very important to have stream-of-consciousness, unagendaed conversations, too. Generally speaking, we’re great at structure, and less good at making space for wondering and wandering. For more on the power of wondering and wandering, make sure to check out my interview with Natalie Nixon.

Be sure to check out my conversation with Jane Portman and Benedikt Deicke, co-founders of Userlist, on how they connected through shared communities and learned how each other really worked through real-world, previous projects.

You may also enjoy my interview with Carolyn Gregoire and Scott Barry Kaufman, the co-authors of the 2015 bestseller, Wired to Create, where we unpack how they managed their working relationship.

And if you really want to dive deep into the idea of being a conscious co-founder, make sure to check out my conversation with my friend Doug Erwin, the Senior Vice President of Entrepreneurial Development at EDAWN, the Economic Development Authority of Western Nevada.

Links, Quotes, Notes, and Resources

Clarity.so

Minute 6

Richie Bonilla:

So basically in our first year working together, we talked a few times a week and we would have very in depth conversations about the work that we were doing. Once we started working on Clarity together, which was sort of a very organic and gradual transition. We talked, we would meet every day to talk. And we would talk about the things that we were doing, which would take maybe 15, 20 minutes.

And then we would spend another 40 minutes every day. So it would be like a total hour every day, talking about what this could become and what this could be. And so we basically spoke every day for an hour for the first year that we worked together. And I think that we're still reaping the benefits of getting on the same page in that way. Whereas, like a lot of my friends who don't work remote thought that was crazy. They're like you sit on the call for an hour a day. What do you even talk about? And I think that was probably one of the best things we ever did. I think we're still, like I said, reaping the benefits of that alignment.

Minute 25

Eni Jaupi:

This may be just, I don't know how to exactly call it, but we always have said this out loud: that our best interest is this company and knowing that full well, that just irons out whatever small conversation that we were having, that did not match, or our opinions did not match completely. So those are mostly just knowing that the other person knows that your intentions are fully aligned with his and at the same time, just putting aside your pride, that sometimes you just need to say, "Okay, let's just do it. And that we can talk about it later again." Try to not say I told you so, if something goes, as you imagine, as the person that said no, or the person that had the objections predicted or said, so just small things like that are part of the growing experience.

Minute 30

Richie Bonilla:

Even though we agree right now, let's still take the time to run through these other scenarios, so that we're make sure that we agree, rather than just taking a surface level agreement and being like, yes. And then running through it later." I look at it as de-risking the project, because if we get into details later, it's actually harder for us to fix this. So yes, we agree at this level, but let's go two or three levels deeper on this and make sure we agree on those levels too. And the way that we end up doing that is by saying, "Well, what happens if you know this or that?,Or the other thing?" And playing through those scenarios.

Minute 32

Richie Bonilla:

And I think that this is representative of how we approach our whole relationship, where in the beginning of starting to work together, we're like, "Oh, we're taking this more seriously." Getting aligned on what kinds of things you're trying to do with your life. Like, "Hey, if this is an opportunity here to make this something really big, are you here on a 10 year mission with me? Or are you looking for a passive income side hustle, SaaS product?" Those are fundamentally different visions. And it's really difficult if one person is like, "I'm sort of happy with like a 10K a month SaaS business. Why are we going through all this trouble to change the world?"

That's a really tough thing to reconcile later. Also, things like, "Hey, if it was right for the company, would you move to the United States? Would you move to New York City and come over here? Is that a deal breaker for you? Or is that something you're open to?" Because, we don't know what the future's going to hold. And that might be the right thing for the business.

So looking at all of those sort of irreconcilable positions really early on and having those conversations really early on, I think is something that we definitely did. And I think that people avoid it, because they're scared that like, "Oh, this person doesn't want to ever move to the US. And is that something that I can live with? And if not, crap, I just lost this opportunity." But I think it's the alternative. It's way harder to have that conversation later, if you're not in agreement.

Minute 36

Richie Bonilla:

I think that the way I see it is like, always talk about the thing that's relevant right now first, right up until the point where we feel like we have a handle on it. So getting through those open questions and then depending on where we're at. So sometimes something's really urgent. It's like, let's get this conversation done. Let's make these decisions. And let's get off the phone as soon as possible. Other times, you finish that conversation. You're like, "I've got this thing in my head, this idea that I can't kick and I want to share it with you. And let's explore that for a minute." And maybe we won't build that feature or encounter that problem for a few months. But by doing this, by the time we do get there, we've already talked about it 2, 3, 4 times, and we've already built up a shared mental model of like what that's going to be

More about Richie and Eni

Richie Bonilla is Co-founder & CEO of Clarity. His background is in product design & software development. He entered web3 by contributing to an early NFT gaming community in 2018. He worked as a remote freelancer for 10 years across various industries. This perspective informs his work at Clarity where he and Eni are building tools for DAO contributors, who experience many of the same problems faced by web2 freelancers.

Eni Jaupi is Co-founder & CTO of Clarity. His background is in software engineering, working as a remote freelancer for 9 years. His first introduction to crypto was in early 2017 while building side projects.

Full Transcript

Daniel Stillman:

I will officially welcome you to the Conversation Factory. Richie, Eni, welcome aboard. Thanks for making time for this. I really appreciate it.

Richie Bonilla:

Thanks for having us.

Eni Jaupi:

Thank you for having us.

Daniel Stillman:

So I think let's start with the big picture, which might be giving folks a sense of who you all are and what you're working on.

Richie Bonilla:

So my name is Richie. My background is in design and product, also technical. And so just like sort of a multidisciplinary founder. I'll let Eni introduce himself, but what we're working on is called Clarity. We believe that... We were freelancers in Web2 and we think that freelancing is great, because you have a lot of independence, freedom. And if you do a good job, you can make some pretty good money, but the downside is that it's very lonely and it's also very risky for a lot of folks, because they don't know where that next project is coming from.

Richie Bonilla:

And we see Web3 and DAO as a way to solve those last two pieces, because we think that community and networks help with that. And so we're building Clarity, which helps these DAOs to become more organized and more legible and more accessible, so that more people can engage with them. And so Clarity takes the form of a collaborative workspace that integrates tokens very seamlessly into the experience.

Richie Bonilla:

It includes both documents and project coordination tools, natively, and some other more social features that help people coordinate together. And so we think this is really important for people to be able to build reputation and be able to go off road and be an independent worker, and be what we call on Web3, a contributor. That's the new version of freelancers in our opinion. And so, that's what we're working on.

Daniel Stillman:

That's cool. Eni, do you want to add yourself?

Eni Jaupi:

Yeah. Just to give a brief background on myself. I'm Eni, I'm from Albania, so pretty far away from Richie. I'm primarily a software engineer. I say primarily, because when you work the remote or in general, in a project by project, you have to wear many hats. But I like to call myself a software engineer, first. I've worked remotely and as a freelancer practically, my whole career.

Eni Jaupi:

I wouldn't be able to say was what are the best things and the worst things, because this is practically all I know. So it would be a bit hard to make a difference, is what I can say though, is what Richie said about it being full of great opportunities, but at the same time being a bit lonely, just because you're not having so many casual conversations with somebody that you meet with the screen, a few times a day or a few times a week. So about Clarity, I think Richie is the voice that I also like to hear, when we talk about Clarity itself. I just give all my opinions away. And that Richie actually say them back to me, because that just feels so much better and sounds so much better than me actually saying it.

Daniel Stillman:

So Eni, are you saying that you use Richie as a sounding board, like you express your ideas and then Richie helps reframe them back to you? They make more sense.

Eni Jaupi:

Yes. That's almost always been the case even in our previous project, because in our previous project I was in the team. So I was a software engineer, but I had no prior relationship to Richie. So our first meeting was practically in a sprint kickoff. So of course, there was that tension of a new developer coming in and the project manager on the other side, having expectations for you, but what we found worked and I think that has always been the case was, what we're talking about a bit earlier, which is, I like to give my opinion. I have a lot of opinions about product in general, but being of an engineering mind is really hard to explain in a human in "Way". And that'-

Daniel Stillman:

Your so called human ways of talking.

Eni Jaupi:

Our so called human way of talking. And Richie has an outstanding ability to really understand what I'm trying to say without me needing to break out of that role, because you either have to do one or the other, if you really want to be good at one. So even when I change hats, practically, my way of speaking actually changes quite a lot, because when I'm trying to say that, "Okay, these things that we are trying to build is really cool, is really important, but technically these are the challenges." It's really hard to do that, if you want to also be able to convey that... Okay. The thing that we are trying to do is going to be done, is just how it's going to be done, that needs some talking through.

Daniel Stillman:

Richie, anything you wanted to add to that? How does that spark for you?

Richie Bonilla:

Yeah. I think that's the unique thing about us was that, I also similarly have been a freelancer for eight years until... Clarity is like our first real job for both of us. And I think that early on in our relationship, especially for the first year that we were working on Clarity together, but I would say... Let me restart that. So basically in our first year working together, we talked a few times a week and we would have very in depth conversations about the work that we were doing. Once we started working on Clarity together, which was sort of a very organic and gradual transition. We talked, we would meet every day to talk. And we would talk about the things that we were doing, which would take maybe 15, 20 minutes.

Richie Bonilla:

And then we would spend another 40 minutes every day. So it would be like a total hour every day, talking about what this could become and what this could be. And so we basically spoke every day for an hour for the first year that we worked together. And I think that we're still reaping the benefits of getting on the same page in that way. Whereas, like a lot of my friends who don't work remote thought that was crazy. They're like you sit on the call for an hour a day. What do you even talk about? And I think that was probably one of the best things we ever did. I think we're still, like I said, reaping the benefits of that alignment.

Eni Jaupi:

I think Richie is talking about the median, because those conversation could go into five or six hours. For me, it was 6:00 in the morning and I was starting to not sound really good, because I was falling asleep. So that's, where the conversation would naturally end. So I think that has always been a cool part. And when we do it now, it sounds... Because it's not that this was, oh, like 10 years ago. But it sounds nostalgic, because when we still do that and we go into deep conversations for hours and hours [inaudible 00:08:02], and this is through the screen, so through a microphone, it just feels organic.

Daniel Stillman:

I think this is an amazing insight in terms of the way you're creating intimacy from far away. And as you said, Richie, before we started recording, the two of you met in person once, and that's all after you had already been working together for some time on this project, on this company, is that right? So you'd built up a lot of connection points and a lot of alignment and a lot of intimacy, intellectual intimacy, all of it from far away.

Richie Bonilla:

Yeah. I think that was because we let conversations go stream of consciousness. So we would have our agendaed conversation and be very disciplined about that. But then we would just like, let things... We still do this. We just allow for stream of consciousness to take over in a conversation. And sometimes we go over time. Sometimes we talk about stuff that probably is not relevant for six months, but I think a lot of the time we, what we're doing is... I think most of the time it's actually very productive in that, it allows us to keep a shared mental model of the entire business. And so we've always done that. And we did build up a lot of... I think I like that word, intellectual intimacy, before meeting in person, because of that.

Daniel Stillman:

One thing that I've heard from a couple of the other co-founders that I've been connecting with is, I find it interesting, just like any other relationship there's a million, there's so many fish in the sea, there's all these people out in the world. There's a lot of makers and people with ideas and people who want to create a company. Of all the... What's that line from Casablanca? Of all the bars in all the world, you walked into a place... How did you, of all the serendipity, what serendipity created, the two of you crossing paths, and then taking that next step into getting closer? What was right before, "Yeah. Let's work on this together?"

Richie Bonilla:

Yeah. So on my end it was bidding for a job on Upwork that I won. And so I was working out. We worked on this project, there was these casting directors in New Orleans. They had this amazing system for casting directors to find extras, because extras casting is very different from main character casting. There's a lot of like bulk casting. It has to be a lot about their appearance and just like a lot 50 different attributes that you can match people on. And so they had this system that had organically grown. It was way more than what they had ever anticipated doing. They needed someone to come in with a product lens and really rethink it. And so they hired me for four months before bringing Eni in. And so I had done a lot of user research and iteration, and then he was brought in to sort of lead the development team and help to start building it. And so that was on my end, what it looked like.

Daniel Stillman:

And so Eni, this is what you're talking about. You're plopped into the middle of this group that's already been together, been working for a while.

Eni Jaupi:

So on the other side, for me, it was actually a lot less intentional. So it started as a conversation with somebody that was part of the team and they were just saying, "Okay, you should jump in. I think this is a really cool app that you could work on." And so I just got there and practically, okay, these are the things that we need. This is the stack. Sounded cool. The app looked cool. So it was a lot more just a nonchalant decision of, "Okay, this is a cool project. Let me just try it out." The guys were already working, I believe at that point. So they had quite a few things built, but when I jumped in the thing that actually connected us more so than anything else was caring about the project. When you're in freelancing, you have projects one after the other.

Eni Jaupi:

So it's kind of hard to care on a deep level, that the thing that you are working on really needs to be something big. And from my side, that has always been the goal. So to be a big part of something big. And so the tendency to care, I think that's just what did draw us, as sometimes we would be the only two people talking in a call and maybe that would be kind of annoying, but that was also organic. It wasn't something as a single case or a single decision that we worked on specifically, and that built our relationship up.

Eni Jaupi:

It was just get on a call and just things flowed from there. We understood each other really well, so that also helped quite a bit. I was also not really shy to say my opinions. So I think that was also something that from Richie's side actually, that stood out as, okay, this guy knows what he is talking about. And at the same time, some of those ideas, if not all, they clicked. So that, probably has something to do with it.

Daniel Stillman:

So in the story now, I'm hearing you're starting to click, you're thrown to the middle of this experience together. How did things accelerate to these long, weekly conversations? What was in the middle between connecting and feeling some similarities, some understanding to, yeah, we're going to work on this thing together and really accelerating into that?

Richie Bonilla:

Yeah. So I think that one of the first things that clicked for me was that Eni would show up to these calls and he would ask me really detailed questions about what we were going, what problems we were solving, and then he wouldn't take any notes. And I was just sort of like, "What's this guy's deal? He asked me these questions, he doesn't take any notes." And he'd also, didn't read off of a list of questions. He would just sit there and ask me. And I was like, "He's not listening. Why are we doing this?" But then every week it would like, that would work and everything we talked about would be implemented or whatever, and then we'd move on to new stuff. And he never dropped anything. And I was like, there's something up with this guy.

Richie Bonilla:

There's a trick or he's just like raw intelligence is really high. He just retains information. That's not how my brain works. And so that was like the first thing that clicked. I was like, okay, this is interesting, a different relationship than I've had before. But I'd say that one of the things that was happening was that I had... Because I had been working remotely for so long and I started my career working remotely. I developed a system for running remote teams, using existing tools in a specific way. And I was prototyping that system on the team and Eni really took to sort of... I think he realized what I was doing, or at least that's my impression of it. And started suggesting improvements to that system and the bigger thing that we were building.

Richie Bonilla:

And so over time, that's the system that became Clarity. That was the thing that we started to then build product around. Especially once we started to contribute to these Web3 communities in like 2019. And so that's how Clarity progressed. And so he was sort of working on Clarity before it had a name, just by helping me to sculpt the system to run the team that we were running together. And so I think that's where we really started to mesh, was like we were having conversations outside of the work that we were doing for the client. We were really working on something else, an art project together. It was like a Meta project. And that took a larger and larger percentage of our mind share over time.

Daniel Stillman:

So Eni, you were aware of the structure and you were giving feedback, not just on the content, but the process, the structure.

Eni Jaupi:

At first, I was not aware specifically that it was a structure. It just seemed to be something that worked. I couldn't give a name to it, because I hadn't talked to Richie specifically. There was something that he was doing, but at some point you start to pick the patterns of, okay, we are doing this, this and this. And every time that we did that, it worked every time that we didn't do it, it worked less well than it could. So that just became a lot more obvious. And of course adding input, of course, I believe the input that I give back then, Richie, must have absolutely crossed his mind. It's just that he was being polite with accepting feedback. But at some point Richie said that he was going to step away and he mentioned that he was going to build a "Ticketing system."

Eni Jaupi:

That's what he called it to practically make it sound as, "Yeah, I'm just going to do this thing probably to not jinx it," but that's when it actually clicked that, oh, okay, he's going to take this thing and make a product out of it. So that's where I messaged him and the message was just, "If you need help as a passion project, I'd be glad to help you." So it didn't start as, "Okay. Let's do this thing together." Started more so, "Oh, I see what you're doing. I see where your head's at, and if you just need help, especially on the technical side, I'd be happy to help with it."

Daniel Stillman:

That's such an interesting... That's a moment where you're like, wait, there's something here and you sent that invitation. Richie, do you remember getting that message from Eni of like, "Yeah. Yeah. Tell me what I can do. Tell me how I can help."

Richie Bonilla:

Yeah. I was sort of conflicted, because I knew that I had heard and believed from my own observation that the best co-founders are people who you worked with on something prior, whether you worked at a company together and were on the same team, or whatnot, or had a previous startup together. And so being a freelancer, I didn't even have a lot of "Colleagues" that I had worked on teams together. And so I really wanted to work with Eni, and I thought that if there was somebody in my life who I could work with on something, it would be Eni, but I also was like, I don't feel comfortable like poaching somebody off of my client.

Richie Bonilla:

I don't know where this thing is going to go. I didn't want to create any bad Juju. And so I was sort of like, "All right, guys, I'm leaving." I broke it to the team. I was like, "Hey guys, I'm leaving. I'm scaling down my freelancing to focus more on this side project." And then when Eni reached out and was like, "No, no, what are you doing? Tell me more." And then was like, "I want to work on that with you." I was like, "This is some universe stuff. I can't just ignore this."

Richie Bonilla:

And so I made it very clear to the client, who's a friend of mine still. And I said, "This is what's happening. Put it in writing, make sure everyone knew what was going on. He's working out with me on some stuff that might increase in the future, who knows." And that was my clean conscience progression through the situation, because I was like, can't really give that up. This is someone who I'm working with, who I've never worked so smoothly with somebody, who's clearly this talented. And so you can't just like pass that up.

Daniel Stillman:

You answered the call, that message. And I think that's really cool that you tried to be really clean about it. And something we were talking about before we got started was, and I appreciate you mentioning universal received best practices. And I think you definitely nailed on one, which is you can't start from zero. You're already building on some knowledge about each other and you're building that intimacy on a foundation. And Richie, you'd mentioned that you'd had some previous experiences that were maybe not so awesome on the co-founder side. Maybe now's a good time to talk about some of the anti patterns that you've experienced in the past.

Richie Bonilla:

Sure. Yeah. We had at my first company, which the funny thing is I've freelanced through that entire company, because it never quite got off the ground in a meaningful way from a revenue standpoint. And so I had to always be a freelancer to make that work as well. So my point is just that working on that company, we dropped out of college to start that company. And I started it with some guys who I had just met and there were four of us. And so there was all these red flags, like in retrospect. Just met, never done this before, four co-founders. You're just compounding the number of things that are red flags for co-founder relationships not working out.

Richie Bonilla:

And that came to bite us. So in the end it ends up being like me and one of the co-founders who's a CEO and we were working on it together for the longest period after the other two folks had left, one didn't want to leave school. So we had to tell him, "Sorry, but that's not the level of commitment that we're looking for." So that, was like a tough situation. And then the other one wanted to go to grad school. And so then he decided to go back to school or he didn't drop out in the first place, he graduated and then went to grad school. And so we were sort of left the two of us. And then unfortunately I had to decide to leave, because just the direction of the company, we were focusing more on like the operations of hospitality properties, rather than like the software part, which is what I was really interested in, where I saw my career going.

Richie Bonilla:

And he was really good at that part. And so that was another tough thing was like, then I had to be the one who left, which was also its own struggle. And there's all the writing on the wall, like in retrospect of like I said, those various criteria that we didn't hit, but then... So with this one I had a mental checklist of things I wanted to see in a co-founder relationship. And I was prepared to basically be a solo founder, if I didn't find that, but that definitely wasn't the preferred situation.

Daniel Stillman:

Yeah. So a lot of that was in your mind, I'm guessing as you were thinking about this next, next idea. Eni, had you had past experiences with the downside of co-founding?

Eni Jaupi:

Not really, I don't want to jinx it, but this is my first co-founder experience.

Daniel Stillman:

You just have to say jinx and then hit something, hit some wood or something.

Eni Jaupi:

Oh, okay. Got it. So on my side, I'm trying to be the exception of not having prior roadmap of failure points. So I hope to never know what those failure points are. I can't say anymore than that, at least. I know my struggles. I know what I could have done better, but I'm not sure if I would've changed that, as opposed to something else, because I think the journey to be where we are now also needed some in between points, that in retrospect are not ideal, but of course it's part of the growth. So I wouldn't say that something is specific to either being successful or not. I think the experience is also growing and into actually becoming two people that can talk about more than the specific task in hand, about things that span multiple years, or multiple decades as we sometimes do.

Daniel Stillman:

Eni, when you think about the time you've been working on this together, you talked about failure points and learning. Do you feel like there have been friction points that you've been able to work through? Well, clearly effectively creatively. And if so, I'd be curious to explore how you manage those. You haven't had an explosion yet. We're still here. You guys seem like you're on good terms, but there's always bumps on the road.

Eni Jaupi:

Of course. I would say that at least nothing has sticked out as, okay. We absolutely need to figure this out before we are able to continue working with each other. This may be just, I don't know how to exactly call it, but we always have said this out loud that our best interest is this company and knowing that full well, that just irons out whatever small conversation that we were having, that did not match, or our opinions did not match completely. So those are mostly just knowing that the other person knows that your intentions are fully aligned with his and at the same time, just putting aside your pride, that sometimes you just need to say, "Okay, let's just do it. And that we can talk about it later again." Try to not say I told you so, if something goes, as you imagine, as the person that said no, or the person that had the objections predicted or said, so just small things like that are part of the growing experience.

Eni Jaupi:

I think those are just things that happen. I think any relationship has those and especially two people that until very recently could not meet each other. Like, "Yeah, okay, let's do it." But if you say that too many times, there are too many things left untold or unsaid. And you don't have conversations, maybe sometimes the time, maybe sometimes just as a... "Okay, we need to do this. You cool with it?" "Yeah. I'm cool with it." Those are just things that compound, so trying to get that out of the way as soon as possible. Or as soon as you see that something is penting up. I think that's part of it. Although full disclosure, we have been so much on the same wavelength, that when we had the discussions about product, one of us would just be the devil's advocate.

Eni Jaupi:

So we would be on the same page and the other person would take the stance of, "Okay, I'm going to take the stance of, let's do this other thing." We are on the same page. We want to do that. But the other person just came up with reasons to knock off the thing that we were both agreeing on. So it sometimes goes to the point that we agree on so many things where we are in the same wave length that we need to take stances of, "Okay, let's do this from the other side. So let's try to knock it down." And one person tries to defend the current position the other person becomes a devil's advocate saying, "Yeah, but there's also this one, or this case, or this case." So I can say about the red herrings, or big things actually.

Daniel Stillman:

And are you setting up that devil's advocacy conversation intentionally, like I'm going to... Or Richie is making a face like yeah, maybe no. Or it just happens organically.

Eni Jaupi:

It happens organically. So it depends on the thing. If it's a technical discussion, or usually the "Disagreement" of opinions are when Richie's designer brain is versus my engineering brain. Those are the ones that we don't need to consciously go into the devil's advocate. Or in the other side, we just try to come up with reasons why the thing that we were both thinking about does not work. So we consciously go into, "Okay, what if this is the case? Does it work or not?"

Daniel Stillman:

Yeah. Richie, what's this been like hearing Eni process these thoughts? I'm curious. What's the all sparking in you?

Richie Bonilla:

Yeah. The funny thing is, I think we do, do that, but we've never... I don't think we've ever used the word devil's advocate in describing it. We never actually said like, "Okay, I'm going to take the devil's advocate position here." We usually say something like, "Well, the counter argument to that is-"

Daniel Stillman:

Yeah.

Richie Bonilla:

And it's sort of like, I think of it as we're programming a system and we need to make sure... We're QA testing the ideas, if you will... Here's an edge case where that doesn't work. And let's present this scenario. Let's run this scenario and see how it plays out. And so I think it is doing exactly what Eni described, but not in a way that I think people think when they hear the term devil's advocate, because that can often just be the person who... I think devil's advocate has a really bad recognition.

Daniel Stillman:

I'm not a fan of that. It's like, "Why would you advocate for the devil? That's a terrible idea."

Richie Bonilla:

Yeah. There's a lot of like, "Oh, you're just masking your actual opinion behind this contrarian thing in order to like say something that is going to upset other people." I think that often is like a misuse of devil's advocate. And so like I said, I don't think we've ever used that, just that terminology. But we do it in the sense of like, "Let's run through these other... Even though we agree right now, let's still take the time to run through these other scenarios, so that we're make sure that we agree, rather than just taking a surface level agreement and being like, yes. And then running through it later." I look at it as de-risking the project, because if we get into details later, it's actually harder for us to fix this. So yes, we agree at this level, but let's go two or three levels deeper on this and make sure we agree on those levels too. And the way that we end up doing that is by saying, "Well, what happens if you know this or that?,Or the other thing?" And playing through those scenarios.

Daniel Stillman:

This is like explicating the positions without taking them.

Eni Jaupi:

Yes. So just to clarify that I've at least [inaudible 00:31:31] we use it as a non bad meaning thing. Surprising. So I just meant doing the... Just take taking the opposite stance of the thing that we're discussing. I didn't notice until right now that I should be more careful with the-

Daniel Stillman:

No, no, there's a-

Eni Jaupi:

Explaining that.

Richie Bonilla:

Yeah. This also happens too. We just have like a cultural... "Oh yeah. So that's, how we use the word here, or like that's how-"

Daniel Stillman:

But I love this idea of QA testing an idea. So what I'm taking away is, and it sounds like you're on the same page of this is, QA testing an idea, looking at the whole problem space, looking many layers down and not necessarily taking a position, but exploring a positions. And I feel like in terms of working through challenges as an important question, this is absolutely best practice. And it's great to see the two of you just willing to dance around in the problem space before you take hold of a solution and run with it.

Richie Bonilla:

Yeah. I think like to your earlier question of what are things we've creatively done about like to do this? And I think that this is representative of how we approach our whole relationship, where in the beginning of starting to work together, we're like, "Oh, we're taking this more seriously." Getting aligned on what kinds of things you're trying to do with your life. Like, "Hey, if there's an opportunity here to make this something really big, are you here on a 10 year mission with me? Or are you looking for a passive income side hustle, SaaS product?" Those are fundamentally different visions. And it's really difficult if one person is like, "I'm sort of happy with like a 10K a month SaaS business. Why are we going through all this trouble to change the world?"

Richie Bonilla:

That's a really tough thing to reconcile later. Also, things like, "Hey, if it was right for the company, would you move to the United States? Would you move to New York City and come over here? Is that a deal breaker for you? Or is that something you're open to?" Because, we don't know what the future's going to hold. And that might be the right thing for the business.

Richie Bonilla:

So looking at all of those sort of irreconcilable positions really early on and having those conversations really early on, I think is something that we definitely did. And I think that people avoid it, because they're scared that like, "Oh, this person doesn't want to ever move to the US. And is that something that I can live with? And if not, crap, I just lost this opportunity." But I think it's the alternative. It's way harder to have that conversation later, if you're not in agreement.

Daniel Stillman:

Eni, how do you feel like you manage the balance? Because, you all are still talking very frequently. Is it still an hour a day, at least, until, or at least until Eni falls asleep? How are you balancing the regularity, but also the talking about now, and also that longer term, because it seems like in every conversation you're circling around all of those levels.

Eni Jaupi:

That's a hard one, because it just boils down to, "Okay. We need to get back to a now level," or if we feel that this conversation is proving to be helpful, then we continue with it. But me and Richie say always that in what we do in startups, you have to know which fires to let burn and just feel the heat and deal with it. I think that's the same mindset as with the conversation. So if you feel that, "Okay, this is something that we can talk about later, we can postpone it." And this is usually something that comes naturally, if you have the shared context of everything going on. As you kind of feel it, "Okay, this conversation is drifting a bit too much for now. We don't really need to have it." So it's about deciding what is that point that, "Okay. We have gotten maximum value from it. No need to go further than that."

Daniel Stillman:

Yeah. Richie, is there something you wanted to yes and from that?

Richie Bonilla:

Yeah. I think that the way I see it is like, always talk about the thing that's relevant right now first, right up until the point where we feel like we have a handle on it. So getting through those open questions and then depending on where we're at. So sometimes something's really urgent. It's like, let's get this conversation done. Let's make these decisions. And let's get off the phone as soon as possible. Other times, you finish that conversation. You're like, "I've got this thing in my head, this idea that I can't kick and I want to share it with you. And let's explore that for a minute." And maybe we won't build that feature or encounter that problem for a few months. But by doing this, by the time we do get there, we've already talked about it 2, 3, 4 times, and we've already built up a shared mental model of like what that's going to be.

Richie Bonilla:

And so what ends up happening is that we have a really tight grasp of the details of the work that we're doing right now. And we also have a really robust mental model of all of the work we're going to be doing for the next three months. And then obviously there's the longer term stuff that we're talking about. "Okay. That's not going to be relevant for five years. Let's just dream a bit. That's a 10 year thing. That's a 100 year thing."

Richie Bonilla:

We have those conversations, but they're obviously a lot less frequent, but these loop, these concentric circles, if you will, evolve by allowing the conversation to go beyond just what is relevant at this moment. And it's the stuff you would talk about over lunch, or dinner, or drinks. Because we don't have that, I think that allowing a conversation to go a bit long is the way that it goes and not fighting it. So not say, "Oh, we should get off right now." If we both got energy for the conversation, let's harness that energy right now. And let's harness that enthusiasm right now, because we can't schedule it in. You can't schedule, "I'm going to have energy for this topic next week." Yeah. You can't do that.

Daniel Stillman:

And yet you can organize your schedule to allow for that space, which I don't think everybody listening to this has a calendar that necessarily allows them to say like, "Well, let's push things off and let's keep going with this." How do you two create this space to make that possible, to make those kinds of continuous conversations possible?

Richie Bonilla:

I would say so we have an international team as... Oh, you know that, but we have a really international team, because I think we have nine people right now. We have three in Asia, three in the US and three in Europe. And so out of necessity, we sort of need to be very disciplined about how we meet and when and for how long. And I think that what we... I know that what we do is we create a meeting time where we meet every day, every weekday we meet at the same time, some of those meetings are scheduled to go long. Some of them are really short, like 30 minutes, but the product team meets every day. We have it all hands every week for everyone who's contributing actively to Clarity.

Richie Bonilla:

And then we have one on ones with each other, like throughout the week. So every week we have one meeting with everyone in the company, we have five meetings, or four meetings with... No, actually five, because there's one right after the all hands. So five meetings with the product team and then one meeting with a one-on-one with everybody. And so throughout all of those conversations, you maintain a mental model of the entire thing. But because that happens at the same time every day, the rest of the day is wide open.

Richie Bonilla:

And so you can actually play with that time. Most of the time it's deep work time, but if we've got something that's running long, let's break off the people we need from this meeting, let everybody else go. And let's just figure this out for as long as it requires. And I think that the whole company basically rests on Eni's ability to have a Eastern schedule instead of an Albanian schedule. Because if he wasn't a night owl, I don't know how this would work.

Daniel Stillman:

What was it like meeting up in person? Where did you meet in person? Was it just the two of you, or was it getting the whole team together?

Richie Bonilla:

It was really strange, brutally strange. We met in Portugal in Lisbon and the first hour was incredibly weird. And I think like the only way I can understand why this was the case is, I think that intellectually, we knew that this was our close friend and co-founder and partner, but our brains didn't recognize that person was that person. [inaudible 00:40:58]. So it had this feeling of, I know that you are you, but I feel like you're a stranger.

Daniel Stillman:

Yeah.

Richie Bonilla:

And that was this really weird thing. And I've met a lot of people, internet friends online, but... I'm sorry, in real life, but I've never had that experience. I think it's just because we had such a robust relationship. And then all of a sudden, after an hour, we went and got dinner with a group of friends and it was still odd. But then after dinner, something clicked and we were a hundred percent normal. It was really strange. And then we were just talking, it was a 100% comfortable, a 100% normal, but that first 45 minutes to an hour was really weird in a way that I still can't get my head around.

Daniel Stillman:

Yeah. What was that like for you, Eni? I can see you're smiling, it's like [inaudible 00:41:51]-

Eni Jaupi:

I have no idea how to explain it, really. So the closest thing is what Richie said in which, "I know you, but I don't know why this feels weird." It was one of those cases that we looked at each other and starts smiling. Okay, what the heck is going on?

Eni Jaupi:

I don't feel like this is the normal way that this should actually work. And so that was... I don't know. I can get that out of my head. I don't know how I would react if we were exactly in the same position. Probably the same. But as Richie said, after an hour, it was as we had talked like that all the time. So it was exactly that. So a switch and I remember exactly where we were, in which we were walking down through some stairs, just clicked and as if that was a norm.

Daniel Stillman:

Wow. I don't think our biology was set up for handling this, so I think you... And I've had this experience myself, where I'm like, "Wow, you're so much taller than I thought you'd be." Because, here we are in this rectangle, we're all pretty much the same size. So it's really interesting to hear about your breaking through that.

Eni Jaupi:

I think the three dimensions actually has something to do with that. So you actually see that this person has a back of his head that you have never seen, like yes, something is wrong here.

Daniel Stillman:

"Wait, Richie's sideburns are so different than I thought they'd be. I could never really make them out." So this is so interesting. I'm really glad you shared this. And I think this is something that's going to be happening more and more, as we live in this fully distributed world and connect with people and do projects remotely. And Richie, you and I have Michael from Huddle and in common.

Daniel Stillman:

They creating teams like this remotely is just the norm. And so more and more people are going to be having the experience that you, Eni, and Richie are talking about, like, "I know you, but I don't know you and I didn't know what you smelled like. That's so weird." And then you just get used to somebody's presence. It's very different. So our time together is growing short. And I want to respect your time, because Richie, you're on a work-cation, which means you at least have a couple of hours or sun left in Mexico and I'd like you to enjoy that. What haven't I asked you when it comes to creating, building, sustaining a powerful, conscious co-founder relationship? What haven't we explored that's important to get on the board?

Eni Jaupi:

I would say a sense of humor.

Daniel Stillman:

Yeah.

Eni Jaupi:

In startup world, you have to be able to take things that are going on and in startup world, everything is going at the same time. So there's definitely something going on at any given point. So having this point that you can look at the other person and say, "Huh, that was kind of tough, wasn't it?" And not be a 100% serious, a 100% of the time. That helps me personally. So that, has been something that I've found to work at least for me.

Daniel Stillman:

Yeah. Totally.

Richie Bonilla:

Yeah. I have a couple of answers to this. I think that the first one is, especially when you're remote, there's not a lot of ways to read body language. So you have to be very clear. An example is yesterday, I opened a conversation with the team that I hadn't set up the conversation properly. And so there was a miscommunication of what my intention was behind the feedback that I was giving. And after the conversation Eni got on the phone with me, he was like, "Hey, I just really didn't agree with you on that." And I thought it was a pretty uncontroversial point and we talked about it, and turned out that just my lack of setup for the conversation made him actually misunderstand what I was trying to get across.

Richie Bonilla:

And so then today I was able to take ownership with the team and be like, "Hey, I realize that was a sloppy conversation, here is what I meant, if we want to talk about it more, we could talk about it now." But getting that direct feedback of like, "Hey, I really didn't agree with you." And then being like, "Why? Let's hash that out." That was the key to then being able to take ownership and correct it with the team. And I wouldn't say it was a big deal, but you stack a bunch of these tiny little things on top of each other and they become a problem later. So that was one of them. And then I would say another thing is, when disagreeing on something and actually being like, "Okay, we've explored this entire topic. We still don't agree on how to proceed. Let's frame it."

Richie Bonilla:

We frame it as like a bet. So you say, "Okay, what are we really doing here?" What we're really doing is we're taking a X $1,000 bet. Here are the parameters. Here's the budget for that bet. And in eight weeks we will know if it plays out and then we can decide how to proceed. So let's take a chunk off of the direction. Let's place that bet. Let's define the parameters for success. And then we'll go from there. And this way, it's not my idea, your idea. It's just like, "Hey, we're going to de-risk this we're frame it that way. We're going to evaluate it later and decide to double down or abandon course." And then the third thing I want to mention is a compliment to both of those, which is, I think that there's this responsibility in a co-founder relationship to not say, "I told you so," like Eni said before.

Richie Bonilla:

But that comes with the paired responsibility is to take ownership proactively over decisions that you made, that didn't go well and to say it before, so no one feels like they have to say, I told you so. So I will err on the side of saying, "Hey, I know I said this last week, that didn't go like I thought it would. I wanted to just take ownership over that. Here's what I think happened. Here's where I think we could do better next time."

Richie Bonilla:

But that was something where I totally miscalculated and I will err on the side of taking more responsibility than it's probably necessary for my mistakes, because at least it clears the air and the team doesn't think like, "Oh, this guy, keeps making mistakes," because you have to make mistakes in order to make progress. If you're doing it right, then most of the ideas you try don't work. If they all work, then you're not trying hard enough, or you're not being creative, or you're not being risky enough, or you're not being ambitious enough. And so you have to create the space for mistakes and for wrong decisions. But also that comes with the responsibility of taking ownership over those decisions and making sure that everyone knows that you know, that didn't go like you said it would.

Daniel Stillman:

Thinking in bets is so powerful and the ability to disagree, but still create forward movement on getting more information is a really, really powerful skill. And so I'm really glad you highlighted that. Also, I want to just acknowledge that we're just about at time and I'm grateful for the time. If people want to learn more about you all and what you're creating, what's the best place to send them?

Richie Bonilla:

Sure. So we have our website for Clarity at www.clarity.so. We have a blog there where we are posting more and more frequently, and we'll continue to do that. If you want the most high speed, high bandwidth version, it would be our Twitter @Clarityteams. Yeah, that's that. And I'm also Richie Bonilla at... I'm sorry @RichieBonilla on Twitter. Eni, is famously not on Twitter, so unfortunately.

Daniel Stillman:

Good for you, man.

Richie Bonilla:

It's the only way to do it. You're stuck with me.

Daniel Stillman:

Are you on Truth Social with [inaudible 00:50:21]? That's a terrible joke. I apologize. And I feel like... We're literally out of time, but if somebody who's listened to this and is like, but I don't run a DAO and looking at, when I looked at what you all were building from the outside, it looked like anybody who's building something collaboratively on the internet could benefit from that. Is that true? Or what kind of teams can benefit from what you all are creating?

Richie Bonilla:

So I would say that it is true that collaborative work can be done on Clarity for most kinds of teams or organizations. I think that we specialize in a type of coordination that is done by people who are not in a hierarchy. And I don't mean that there's no hierarchy. I just mean that they are sort of independent actors who are choosing to work together in a way that is not traditional from like a management perspective. And I think that's different, because we're freelancers. We were freelancers. We've always been that way. We are coming from a sense of not making people feel like second class citizens in the tool by being an independent worker. And that's how we've designed it from the ground up. And I think that there's a lot of that affects the user experience a lot.

Richie Bonilla:

When I think about project management tools in Web2, I think about tools built for project managers, and a project manager's job is to get the most out of their human resources. And that is one way of building an organization. It is not the vibe that I ever resonated with. And so we don't really think that we are building project management software, we're building project coordination software, because it's people who are each choosing to work together on a shared goal from a more equal view, rather than trying to optimize these people's capacity.

Richie Bonilla:

And so that's really the type of coordination that we specialize in. And I think that plays through the user experience, but yes, it is true that you could use it for any kind of team, except, there would be a ton of features for token integrations and crypto native functionalities and sign in with Ethereum, and these other pieces that would probably be totally irrelevant to you. Like bounty payout workflows and stuff like that. So those just wouldn't be that relevant, but if that's the style of coordination that you participate in, regardless of your goals. Yeah, sure. That's relevant. It's just not the type of organization that we typically focus on. We put all of our innovation energy into DAOs and other kinds of DAO like organizations.

Daniel Stillman:

That's really helpful. And I feel like what you're talking about is what a lot of folks talk about as the future of work, more teams that are more networked and horizontal. And so I feel like more and more teams will be more and more appropriate for the things that you're creating.

Richie Bonilla:

Yeah. And we feel that very strongly, because we have always felt this was the most fun, meaningful, interesting way of working. And we've chosen to do that year, after year, after year. And we're just looking to eliminate the downsides, so that more people can engage with that kind of work and not experience the risk, or the loneliness, or other factors that stop you from engaging as an independent worker.

Daniel Stillman:

That is awesome. Thank you so much for really, really putting a fine point on that. I think that'll be super helpful to have it in your voice, so that people understand this stuff. Because, I know it's not in everybody's wheelhouse. Web3 is an edge for a lot of folks out there. I want to respect your time. I really appreciate you two sharing and being so reflective. And I feel like I can safely call scene for the time that we've had together.

Richie Bonilla:

Thank you so much for having us. I'm so grateful for the opportunity to speak about the co-founder relationship and things, because I don't feel like that's a topic that we have a really get asked about. But it's something that's so important to us and that we've treated with a lot of intention and it's been really fun to have a chance to actually speak on that and be asked questions about it. So thank you.

Daniel Stillman:

Yeah. It's my pleasure.

Eni Jaupi:

Thank you, man. Thank you. And also thank you for bringing up a point during our discussions that I hadn't thought about previously, which is, we had talked about me moving to the US, if the company needed it. We haven't talked about Richie moving to Albania, if the company needed it. I thin we have our next conversation setup.

Daniel Stillman:

I hear the food in Albania is pretty good. I'm just saying.

Eni Jaupi:

Oh, it's amazing. I can tell you that.

Daniel Stillman:

You guys may not know this, but in New York City if you ever come, the most popular street for Italian food in the Bronx, Arthur Avenue is all those Italian restaurants are run by Albanians now, Eni. People, all these tourists come... Yeah. You know. Richie knows what I'm talking about.

Richie Bonilla:

Yeah. I used to live over there and I was telling Eni the same thing. I'm like, you won't believe the Albanian food here. You're going to love it.

Daniel Stillman:

People think they're eating Italian food, but it's Albanian food.

Eni Jaupi:

Yeah. But we are really good at talking in Italian. So that's could be the correlation there.

Daniel Stillman:

Yeah. Only if you knew what to look for, would you see all the Albanian flags. You're like, "Wait a minute." All right, guys. Thank you so much. This has been a really energizing conversation. I really appreciate it.

Stories as Medicine

I first met Dr. Paul Browde as part of a multi-month intensive men's work program we were both part of. We were just about to break out into a few parallel sessions about various elements of running men’s groups when Paul raised his hand and said something to the effect of “would it be useful to have a breakout session about our personal narratives and how we use them to lead?”

I watched as the heads of 40+ men swiveled to focus on this one unassuming gentleman and witnessed nearly half of the group switch over from whatever session they were planning on going to and instead, go to sit around Paul to listen to him tell his story and share his wisdom about how to share our own stories. That’s the power of story!

Paul is a doctor of psychiatry and a TedX speaker. He has shared the stage with luminaries like Esther Perel, has taught Narrative Medicine at Columbia University, and co-founded a storytelling company called Narativ.

Paul has some profound wisdom to share about how to become aware of a different type of story - the stories that tell us, as well as the power of sharing our own stories, and examining the stories we tell about ourselves to ourselves and to others. 

As Paul writes on his site:

We are born in connection, we are wired for connection, and it is through connection that we heal and experience our true aliveness.

I have always felt that stories can be the most powerful elements of communication - indeed, they are the thread that holds together each and every conversation. 

Stories are how we connect, heal and come alive.

Listen onward to learn about Paul’s mental models of how to become a space for others to share their stories - to shape your listening as a vessel, a bowl, to receive stories generously.

Narrative is powerful medicine that we can give to ourselves and to the people around us.

Enjoy this conversation as much as I did!

Links, Quotes, Notes, and Resources

Paul Browde: Healing through connection

The Power of Two: How Listening Shapes Storytelling

Two Twosomes, Not a Script in Sight

The Masculinity Paradox: Warmup with Paul Browde - Sessions Live by Ester Perel

Minute 8

Paul Browde:

If you express an opinion and say, "Racism's bad," well, you can be agreed with or not agreed with. But if someone tells you their story about their wife and their child and a little story of life, we can't help but empathize and really understand that person's experience. They become a human being for you.

I'm getting back to narrative medicine, which is that I eventually, with a friend, performed my story as a performance for many, many years in theaters, in churches, in funeral parlors. We performed a story in which I told this HIV story. It was seen by one of the people that was launching the narrative medicine program at Columbia, and she invited us and said, "Could you teach what you do? Because if doctors could learn how to listen to the stories of others and to have some fluency with their own stories, that's going to enhance their empathy." And so we taught a course for many years called Co-constructing Narratives, where people learned how to tell an illness story of their own or someone they loved.

Minute 9

Paul Browde:

Once you've told your own illness story or the story of someone you've loved, it really changes how you listen as a doctor. I believe that strongly. A lot of my work has become that. So this HIV, which was at one point such a terrifying and dismal prospect of a future for me, has become for me, the source of so much, what feels like meaningful work in my life. It's such a paradox, the thing that once felt so unthinkable is now, honestly feels like a gift in many ways to me.

Minute 12

Paul Browde:

I think stories can be a very powerful access to emotion. But I think that, talking about Men's Work, one of the ideas that I think about a lot is that our lives are shaped by the stories in the background. There are these meta narratives or larger stories that we don't even see or know exist that we become part of from a very young age. One of them, I felt it very clearly as a boy, was what is a real boy, and then what is a real man? That was there in the background and it affected how I spoke. It affected how I stood. I don't know if I've ever told you the story, but I was once told by a group of boys that I stood like a girl, because I used to cross my legs as I stood, my one foot went in front of the other. The boys at break at school said, "Oh, you stand like a girl." I became hypervigilant about standing in a different way that didn't feel natural for my body and I believe caused me back pain for many years, but it was an imperative that came from the story about what it is to be a real man or a real boy.

There are these stories that tell us. We don't tell them, they tell us. We are unknowing participants in the story arc. We can become present to them. So if I can become present to, oh, there's a story that says that boys have to stand a certain way, boys have to hold their body in a certain way, then I can start to think, do I choose to live with that story governing me or am I okay with being a different kind of boy who doesn't stand that way and then starts to open up a relationship with myself and what I really want?

Minute 17

Paul Browde:

And it's also about what is the story that you tell as a person interacting with the healthcare profession? People with AIDS changed the narrative. They changed the story of what it is to be a patient, because in the 80s this virus came into being, which nobody knew how to deal with and nobody knew how to treat. And because of what we've spoken about already, no one cared to treat. People didn't mind, or seemed not to mind that people were dying. What happened was that the patients themselves started doing the research and thousands of people sat in libraries and taught themselves virology and taught themselves about these drugs and began to understand what needed to happen. The patients educated the doctors. Patients knew way more about AIDS than doctors did in the late 80s, early 90s. It began to change when doctors took on learning it and eventually it became an incredible specialty with some extraordinary doctors who agreed to learn from their patients and agreed to try folk medicine. Because at that time we just didn't know what worked and so people tried everything.

So being an empowered recipient of healthcare, or being someone who leads your own journey or your tells your own story as someone who uses the healthcare system is also part of narrative medicine, not just for the providers to be better teachers, better communicators. Yeah. So, that's part of it.

Minute 20

Paul Browde:

I think where we find ourselves now is in a situation where we really don't know what's going to happen. We don't know how things are going to unfold, both with viruses, is there going to be another variant, but with climate change and with culture, with the way that we interact with one another, we can all feel that we are in a transition and we don't know where we're going. So I think leadership now requires leaders to be vulnerable and to let it be known that they don't know either. It's rather than saying, "I know where we are going and you're going to follow me," is to be able to say, "I don't know where we're going, but I will lead us in the not knowing and I'm right there alongside you in the not knowing."

Minute 25

Paul Browde:

I know that I think I've talked to you about the listening bowl, but it's something that really informs my thinking and my work, which is if you think of listening as a container, like a bowl, and that the speaking of another person takes the shape of the container of your listening. So as I'm speaking to you, my speaking is taking the shape of the bowl of your listening and your listening is generous and it's open and it's expansive. As a result, I find myself feeling free to speak with you. What happens is what comes out of me is actually shaped by how you listen to me. I think this is very important in all relationships, including with couples who I work with a lot, which is, rather than looking at what someone else is saying, to be able to ask the question, how am I listening so that this is what's coming out of their mouth?

Minute 36:

Paul Browde:

I think it's counterintuitive, the kind of listening that it really requires. I think we are so trained to listen as experts. We listen to help. We listen to fix. We listen to change. I think those kinds of listening get in the way of really allowing something new to emerge. And perhaps the best kind of listening we can do is to bring absolutely nothing, literally bring nothing to what the person is speaking, but that doesn't mean not listening. You're bringing presence.

More about Paul

For the past thirty years, I have worked as a clinician. As a doctor, therapist and couples’ guide, I have been trusted with people’s deeply personal experiences; their despair, their joy and their dreams.

I have performed my own personal life story for diverse audiences across the globe, guiding others in how to listen and tell their own stories.

Full Transcript

Daniel Stillman:

Paul, I'm so excited to have this conversation with you, really. Welcome to the Conversation Factory and thanks for making this space in your life.

Paul Browde:

Thank you, Daniel. It's so great to be with you. I'm really excited about this.

Daniel Stillman:

So for me, the term narrative medicine came across my life because of you, and the putting of those two words together, sort of put my head back, and then the conversation that we had, I guess, a couple of months now to talk about story medicine. It's a really beautiful topic and I want to unpeel as many layers of the onion as we can. So for those folks who don't know anything about narrative medicine and story medicine, can you put it in context? It's a big ask, I know, but I know you're up to the task.

Paul Browde:

I'll try. What's interesting about it is it's a field that is evolving. Anything that I say it is, it won't be tomorrow, because it'll have changed already because it's a new field. People have brought together the field of medicine and the field of narrative and the field of story, and have them talk to one another. I first came across it when I was asked to teach in the Columbia University Narrative Medicine master's program. The intention of the master's program was to teach healthcare professionals how to listen to the people that consult them. You could say to teach doctors how to listen to patients, but it was broader than that, and the idea being that medicine has swung so far into the technical, into checklists.

Paul Browde:

As a doctor, you literally have tens of checklists in your mind as you go through asking questions and you may even have a checklist these days on a computer. So for many people, when you go to your doctor, they sit and look at the computer, ask you questions and then check off yes or no in front of you. While that may be effective in getting to a particular problem, it doesn't really give you a sense of the whole person and the whole person's story and what may be informing the health situation that they're showing up with.

Paul Browde:

So the metaphor of narrative is really, how can we bring, a way we might approach a book, for example. How would we read a book? You read a book with an open mind. You are willing to be taken along on a journey of the teller that takes you to all kinds of different places in the teller's story. Can you bring that kind of listening to a patient?

Daniel Stillman:

Yes.

Paul Browde:

And really be curious about who this person is and what is their story. I had spent many years, I am a doctor, so I'm a psychiatrist and I'm a doctor. For many years I've worked as a doctor, but early in my career, I also discovered myself to be a patient, and at the age of 25 was diagnosed with HIV, much to my absolute horror and shock at the time. This was 1986. At that time it was a death sentence. It was a really terrifying place to live, and in fact, the way that I was treated early on by doctors was very much a checklist, and they didn't know what checklist to use even because AIDS hadn't been treated very much. I felt reduced to this condition that was living in my body and I couldn't talk about it to anyone. So obviously to cut a long story short-

Daniel Stillman:

For people who are listening who do not realize, who were not either alive or part of the conversation back then, it was...

Paul Browde:

Yes.

Daniel Stillman:

... incredibly... there was so much fear around it and fear of the gay men's population. There was revision. So there was a sense of total rejection of this. I heard you talk about this in your TEDx talk, this idea that the patient with this disease is beneath or below us. It's hard for us to imagine. I think it's hard for somebody to imagine now that that was the attitude, but it was not a whole person. You were a disease and that made you... look, I've watched, and we've talked about this before. I've watched two of my great mentors die slowly and terribly of that disease and it was such a scary thing at the time because we knew so little about it.

Paul Browde:

Yeah, absolutely.

Daniel Stillman:

For you to feel like you had to hide that part of you as a professional, I understand. I understand in the sense of empathize with. I can empathize with how hard that was to hide that wholeness of yourself.

Paul Browde:

Yeah, it was very painful and it didn't even occur to me at that time that there was anything unfair about that or wrong about it. It's just the way it was. I think the fact that it was a virus that was transmitted either sexually or through drug use further stigmatized it. And then there were some people who received it through blood transfusions, and that, it was as if those were the people who were considered harmless, or what's the word? They were innocent, whereas the others had somehow done this to themselves and those were actually words spoken. People spoke the words that these people are doing it to themselves. It's God's wrath. Talk about a story shaping how people felt about themselves.

Paul Browde:

But for me and in my personal journey, I came to a point with a lot of support and great privilege actually, that I was never thrown out of my family. I was never thrown out of my friendship group. I was able to speak publicly about it. What that allowed me to do was to talk about, tell my story, just tell my story publicly to people. That became a source of power for me, being able to tell my story, and what I mean by power, was that it allowed me to really use my whole self to make a difference to other people. Once my story had been heard, I was invited to come and speak to people with AIDS, living in Africa, in Senegal and then in South Africa, and to just tell my story. The telling of a story of being a doctor who has HIV and who is alive and here to tell the tale, was really the story that needed to be told because people were feeling so hopeless and many, millions of people have died of this.

Paul Browde:

I began to learn not only the power of my own personal story, but the power of people telling their personal stories. I was very lucky to be able to work with various groups of people who were marginalized by the world. So sex workers, IV drug users, people with AIDS, these are all... and the Roma people, who are otherwise known as the gypsies in Eastern Europe who are very poorly treated and it's still acceptable to be racist about the Roma. We ran workshops with people using storytelling as a way of breaking down that stigma so that through your story you become humanized. If you express an opinion and say, "Racism's bad," well, you can be agreed with or not agreed with. But if someone tells you their story about their wife and their child and a little story of life, we can't help but empathize and really understand that person's experience. They become a human being for you.

Paul Browde:

I'm getting back to narrative medicine, which is that I eventually, with a friend, performed my story as a performance for many, many years in theaters, in churches, in funeral parlors. We performed a story in which I told this HIV story. It was seen by one of the people that was launching the narrative medicine program at Columbia, and she invited us and said, "Could you teach what you do? Because if doctors could learn how to listen to the stories of others and to have some fluency with their own stories, that's going to enhance their empathy." And so we taught a course for many years called Co-constructing Narratives, where people learned how to tell an illness story of their own or someone they loved.

Paul Browde:

Once you've told your own illness story or the story of someone you've loved, it really changes how you listen as a doctor. I believe that strongly. A lot of my work has become that. So this HIV, which was at one point such a terrifying and dismal prospect of a future for me, has become for me, the source of so much, what feels like meaningful work in my life. It's such a paradox, the thing that once felt so unthinkable is now, honestly feels like a gift in many ways to me.

Daniel Stillman:

There's another paradox of the story that I want to unpack, because you and I met through Men's Work where I feel like the ask is to be present with emotion almost without story and the stripping away of story. I feel like with narrative medicine, it seems like story is about humanizing ourselves and empowering ourselves by sharing our story and to enter into other people's stories. In Men's Work, there's this idea that we strip away the story and we come into the present. Then there's a third aspect, which is the stories that run our lives. Not all of the stories that we're telling about ourselves are helpful stories. I don't know if there's a triangle of narrative that I'm seeing in my mind of there's this powerful aspect of story and then there's limiting aspects of story.

Paul Browde:

Interesting. Yeah, I think it's so true. It is a paradox. I think that at different times we need different things. I think there is a way of telling a story in which you are not present for the telling. It becomes habitual and you may as well be reciting it off by heart. I know that for certain stories, particularly when they've been very painful, you can detach from the story and you can hear someone tell a story about the most terrible things that happened to them with absolutely no emotion. It feels really disconcerting to listen. If someone brings emotion to the telling of a story, so they allow themselves to really feel the experience of the telling of the story, sometimes what happens is emotion arises. If emotion arises, you don't just dampen down the emotion and plow through with the telling. Then there's a really good time to stop and allow the emotion to be there.

Paul Browde:

I think stories can be a very powerful access to emotion. But I think that, talking about Men's Work, one of the ideas that I think about a lot is that our lives are shaped by the stories in the background. There are these meta narratives or larger stories that we don't even see or know exist that we become part of from a very young age. One of them, I felt it very clearly as a boy, was what is a real boy, and then what is a real man? That was there in the background and it affected how I spoke. It affected how I stood. I don't know if I've ever told you the story, but I was once told by a group of boys that I stood like a girl, because I used to cross my legs as I stood, my one foot went in front of the other. The boys at break at school said, "Oh, you stand like a girl." I became hypervigilant about standing in a different way that didn't feel natural for my body and I believe caused me back pain for many years, but it was an imperative that came from the story about what it is to be a real man or a real boy.

Paul Browde:

There are these stories that tell us. We don't tell them, they tell us. We are unknowing participants in the story arc. We can become present to them. So if I can become present to, oh, there's a story that says that boys have to stand a certain way, boys have to hold their body in a certain way, then I can start to think, do I choose to live with that story governing me or am I okay with being a different kind of boy who doesn't stand that way and then starts to open up a relationship with myself and what I really want?

Paul Browde:

So those stories, that story of being a real man, a real boy, I think are so present in men's lives and I think shut down a lot of freedom around feeling. When you think about it, the fact that certain human emotions are taboo for men to feel, it's absurd if you think about it. Men are allowed to laugh, but not to cry. They're equally part of our physiology. They're just there. So I think for me, the getting away from the story in the Men's Work that you and I have been together in, has been a wonderful relief as well. It always starts with a bit of a story and then into the emotion and then allowing myself to inhabit my body. I call these physical. There are stories from the body that are not necessarily told in words. They are told in bodily sensations, the way one holds one's body, and the freedom with which one is allowed to move one's body. These are all, I think of them as stories as well.

Daniel Stillman:

Yeah. They're patterns that we live in. And as you say, they're stories that tell us. We're just actors in the stories until we choose and choose a different path. So in a way, if we're building this architecture, narrative medicine has this heritage of being for doctors to become more human and relating with their patients, but story medicine, it seemed in the conversations we've had, feels like it's for everyone.

Paul Browde:

Yes. I think that narrative medicine, there may just be different words to describe a field, which is a very large field. There are narrative medicine programs now all over the world, interestingly enough, that arose at the same time. There seems to have been this simultaneous arising of a field, even though the people who ran those different programs didn't necessarily know each other, because it was a need. It is a need.

Daniel Stillman:

Yes.

Paul Browde:

And it's also about what is the story that you tell as a person interacting with the healthcare profession? People with AIDS changed the narrative. They changed the story of what it is to be a patient, because in the 80s this virus came into being, which nobody knew how to deal with and nobody knew how to treat. And because of what we've spoken about already, no one cared to treat. People didn't mind, or seemed not to mind that people were dying. What happened was that the patients themselves started doing the research and thousands of people sat in libraries and taught themselves virology and taught themselves about these drugs and began to understand what needed to happen. The patients educated the doctors. Patients knew way more about AIDS than doctors did in the late 80s, early 90s. It began to change when doctors took on learning it and eventually it became an incredible specialty with some extraordinary doctors who agreed to learn from their patients and agreed to try folk medicine. Because at that time we just didn't know what worked and so people tried everything.

Paul Browde:

So being an empowered recipient of healthcare, or being someone who leads your own journey or your tells your own story as someone who uses the healthcare system is also part of narrative medicine, not just for the providers to be better teachers, better communicators. Yeah. So, that's part of it.

Daniel Stillman:

The thing we were talking about right before we started recording, this question of what does it mean to take story medicine into the workplace? Because we're talking about like this, narrative medicine is working at a very, very raw juncture. It's life and death and it's people taking responsibility for their healing and doctors becoming more human. I can really see the power of telling your own story and of owning your own transformation seems to me to have myriad applications for leadership development, I think. But I'm curious how it shows up in your work now and as your edge as you're leaning into this.

Paul Browde:

Yeah. It's really interesting. In the last several months from many different sources, I've been approached with people who would like to learn more about story medicine in the workplace. How can we bring this into the workplace? I think part of it is, as the pandemic has happened, first of all, the distinction between work and home has been blurred. People are literally in their homes working. And you couldn't say to people during the pandemic, "That doesn't belong at work, keep that for home." The child is literally running through the room while you're at a work meeting. You can't tell people to not do that. Everybody seemed to understand that during the pandemic. That boundary of work, home began to break down somewhat. While that was challenging, for some people, it was actually very helpful.

Paul Browde:

I think where we find ourselves now is in a situation where we really don't know what's going to happen. We don't know how things are going to unfold, both with viruses, is there going to be another variant, but with climate change and with culture, with the way that we interact with one another, we can all feel that we are in a transition and we don't know where we're going. So I think leadership now requires leaders to be vulnerable and to let it be known that they don't know either. It's rather than saying, "I know where we are going and you're going to follow me," is to be able to say, "I don't know where we're going, but I will lead us in the not knowing and I'm right there alongside you in the not knowing." It's a very different place to speak from, and I think once you start saying that you don't know what, what immediately emerges are emotions. It feels scary to say that. It feels vulnerable. It may feel shameful for a person who leads a larger organization to say, "I'm not sure," or "I don't know," might feel shameful.

Paul Browde:

So to be able to just recognize that and know that even those feelings are valid and acceptable in the workplace, and I don't think people are going to settle for less. People don't want to be treated anymore like objects that get told what to do. They don't want that. They're going to leave and find other jobs. This whole idea of the great resignation, people are leaving because the workplace doesn't work for them anymore.

Paul Browde:

Interestingly enough, I just led a workshop this morning with a group of people in South Africa who run an organization that feeds starving children. We spent four weeks with all the people that work for that organization sharing their own personal stories with one another, stories where they came from and stories as to why they felt moved to work in the sector that feeds starving children. Each person had a personal story to tell that linked them to the work they were doing. Some people had grown up very poor and didn't have food. Some people had grown up on farms and had to milk a cow. These were stories which really showed them aspects of one another that they didn't know. And then today, what we did was have them just tell a story about the future of that organization, how they dreamed it would go. You can also tell a story about the future that is different from the same old story based on the past. The future could be an invention of something new.

Paul Browde:

Given the environment that had been created through the sharing of personal stories, what they came up with for the future of their organization was so beautiful and powerful. And the number one idea that they came up with as a whole group, I said nothing about this, it came from them, was love. We bring love into our workplace and we bring love into our communities, which would've been my hope for them but I could never have told them that. I might have been told that was woo woo. But once the personal story is present in the listening, what starts to happen is people are creative and vulnerable about how they speak the future.

Daniel Stillman:

Say more about that. I feel like there's a little bit more, before I...

Paul Browde:

Yeah. Well, I would like to just, I know that I think I've talked to you about the listening bowl, but it's something that really informs my thinking and my work, which is if you think of listening as a container, like a bowl, and that the speaking of another person takes the shape of the container of your listening. So as I'm speaking to you, my speaking is taking the shape of the bowl of your listening and your listening is generous and it's open and it's expansive. As a result, I find myself feeling free to speak with you. What happens is what comes out of me is actually shaped by how you listen to me. I think this is very important in all relationships, including with couples who I work with a lot, which is, rather than looking at what someone else is saying, to be able to ask the question, how am I listening so that this is what's coming out of their mouth?

Paul Browde:

If something is emerging from their mouth that you don't like, that feels confrontational or aggressive, think how can I shift the way I'm listening? Because that bowl can become obstructed, it can be filled with obstacles. So agreeing or disagreeing, are you listening to agree or disagree, really narrows down the listening. Am I listening to like or not like what the person says? A lot of times we listen waiting to speak. It's really waiting for an appropriate moment to just bat in and start speaking that, we all do that. So when you notice that's what you're doing, you can actually say to yourself, okay, I'm just listening right now. You did it a couple of minutes ago. When you said to me, "I think there's more for me to listen to before I have something to say," and you allowed yourself that space, which then allows me the space to keep speaking. I think it's a useful metaphor. All these are metaphors, but they do help us become better listeners and then help the people around us become better storytellers because we are listening more openly.

Daniel Stillman:

This is so interesting. And by the way, I feel like 90% of the reason why I have this podcast is it puts me on my best behavior to be a better listener and learn more and have a more open space. One of the things I heard in one of your talks, which maybe I want to unpack. You said stories are what happened. And in one sense, I think that is true, that stories are, these are the facts. But the other thing that I'm hearing you say is stories are what we hear, and stories are what we construct from the meta stories that are happening. It's hard to know that another facilitator facilitating that workshop, would they have constructed, well, this is just about love? Would they have gotten there? What would their meta story have been without you there listening for that?

Paul Browde:

I think that's... no, go ahead.

Daniel Stillman:

Well, I guess this becomes what is story based leadership? What are we listening for? How are we shaping the stories that are happening around us?

Paul Browde:

Yeah. It's so complex. I think that when I say stories are what happened, what I'm trying to do is to separate the story from one's interpretation of the story, which of course you could think of as a story in itself. But the idea that something is good or bad, or something is right or wrong, is not a story. It's an opinion, and it's a judgment. Yes, it may be shaped by some meta story that's in the background, but in terms of as you're listening to somebody speaking, if you notice yourself wanting to argue with them, I have found it to be very unlikely that they're telling you a story. Can't really argue with someone's story. I think there are different kinds of narratives, and one of them is the personal story.

Paul Browde:

When you tell me your story, you don't say, "Someone treated me abominably, they were absolutely terrible." We might all agree, but it isn't what your story is. What I'd like rather is to hear you describe in detail what they did, that you came to the conclusion that it was abominable or terrible. In fact, I co-founded a company some years ago and we created a methodology, which we call the what happened method. It tries to keep people very close to describing telling a story with only describing what happened in terms of the senses. What could you see here, smell, taste, or touch, and anything else is interpretation. What's interesting about doing it that way is that people start to feel far more than when they give these sweeping interpretations or tell the moral of the story. They actually start to feel and then the feelings can emerge and be present.

Daniel Stillman:

Because they're skipping so many steps. This feels like two things. One is aspects of nonviolent communication, the ability to distinguish between facts and feelings, and between feelings and needs, and needs and requests. But also, in our Men's Work, I've facilitated several of these. I've been in several of these where you have a charge with someone, and I feel like we're doing the what happened and really getting, well, this is what happened for me, and getting the other person to say what happened for them and holding space for both of those and really putting it all out on the table.

Paul Browde:

Yes, absolutely. It's always about what happened for you or what happened to you. It's not some understanding that something really happened. We know that when there's conflict there's two very different stories that each person might tell. I think the Men's Work that we've done, which is so powerful, is when you've got a group of people supporting the teller, literally standing behind them, holding them if necessary, as they allow their bodies to fully express the emotion that goes along with the story and something transforms when that happens. Then you allow the other person to do the same thing and together come up with some shared space.

Paul Browde:

Another piece of, my mind can go in a million directions, but another piece of another metaphor that I love to work with is that our relationship lives in the space between us. It doesn't live in your experience or in my experience. There is actually a relational space between us that we contend and that we can feed, or that can become polluted and cluttered. Then what we need to do is find a way to clean out that space. I think of the work we see in the men's groups where people have a charge with one another, is in fact a way of de polluting the space, de polluting the relational space between them.

Daniel Stillman:

And that space is filled with stories. If I think about a team and when there's challenges on a team, the challenges, people holding different stories about each other and about themselves and what people think of me and what I can or I can't do.

Paul Browde:

Yeah.

Daniel Stillman:

When it comes to this. Sorry, go ahead, Paul. What did that [inaudible 00:33:13]?

Paul Browde:

No, I was going to say, and I think the hardest thing about that is being willing to accept that another person's story is different from your story, because, and I think this is where the Men's Work tries to get away from story, is that we can identify so much with our story that we think of it as who we are. Then if someone else has a different story, we feel threatened. Our very survival can feel at stake if our story isn't received in the way we want to tell it. I think part of the listening, there's always a process of listening and telling that when we are listening, we are letting go of any attachment that we have to our own stories and how things should turn out.

Paul Browde:

This is really interesting in the health space, so that people, for example, who have illnesses, a particular kind of cancer for which there is a lot of information. There's already a script for how you're supposed to live with an illness. Sometimes I think most people want the script to be that you have a terrible illness, you go through really difficult treatment, and you come out on the other end and you're okay and you learn a really powerful lesson and you're grateful for being alive. That's the story that is expected of people and people feel like failures if they don't adhere to that particular story arc. That's not the usual story art for a lot of people. For a lot of people the story feels utterly chaotic. It feels desperate. It doesn't necessarily have a good ending, and some people really don't want to learn from it at all. They just want it out of their lives and never to think about it again. As the listener, you don't want to impose on a teller a particular narrative arc, a particular outcome, and it's complicated.

Paul Browde:

So when you speak about the workshop that I led this morning, was I listening for love, and that's how someone spoke it? Possibly. It's possible that it was there. I wasn't consciously listening for it. I think it's what I try and listen for everywhere I go. I think it's in the background of how I want to live, but yeah, but I don't want to impose that on a group of people because it doesn't work either, to tell an organization, "You need to love one another, be a loving organization." It's just words and tomorrow it's gone.

Daniel Stillman:

That's just telling.

Paul Browde:

The role of listener and the role of teller, exactly. That's just imposing, and just being aware that everybody has a different way, different story, and it's okay.

Daniel Stillman:

For people listening who want to be able to create more of a space, I feel like when we talk about emergence, this is what we talk about. There's this third body between the two people, this space of relation, which is filled with stories. To create a space where something new can emerge requires maybe a different type of listening than we know how to do right now.

Paul Browde:

I think so. I think so. I think it's counterintuitive, the kind of listening that it really requires. I think we are so trained to listen as experts. We listen to help. We listen to fix. We listen to change. I think those kinds of listening get in the way of really allowing something new to emerge. And perhaps the best kind of listening we can do is to bring absolutely nothing, literally bring nothing to what the person is speaking, but that doesn't mean not listening. You're bringing presence. I'm trained a couple's therapy work, which my teachers taught us about a metaphor, which is that there is a bridge that crosses the relational space. Between you and me, there is a space in which our relationship lives and coming from each of our hearts is a narrow bridge to the other.

Paul Browde:

What we can do is we can walk one at a time, so one is the listener and one is the teller, one at a time we can walk over the bridge and visit one another. The visitor is the one who listens and the host is the teller, and there are certain rules, principles for what it takes to be a good host. So if someone's coming into your world, you want to be slow and careful about how you introduce them to your world. You want to be res respectful, the fact that they're a stranger in your world. You become a very different kind of teller. You have compassion for your listener. Then as a listener, you want to agree to leave your preconceptions behind. You are not coming into another person's world to try and fix or change anything about them. You are just there, full presence with this other person.

Paul Browde:

I think that when you ask what can people think of? I think if you sit and listen to someone and you just imagine that you're visiting, there's nothing to do. You're like a tourist in a foreign land. You don't have to do anything when you walk around Florence. You just observe. You're just in Florence. You see the food, you smell the smells, you see the light, and you experience Florence. We can do that with one another too, and just experience what it's like to be you in your world and there is nothing I have to do.

Daniel Stillman:

This visual of this narrow bridge that maybe is so narrow that I can't bring anything with me, I can only bring myself, I have to leave everything else behind on the other side. Something I often ask people to do is, they have a choice with the next turn. When somebody stops and takes a breath, we can say, oh, and come over to my side of the bridge, or we can stay on their side of the bridge for a little longer and ask for a little bit more.

Daniel Stillman:

I don't think I've ever really thought about the, there's this art of hosting for those people who are listening, who have been exposed to... it's a way of thinking about facilitation and meetings and a gathering, but to think about one conversation at the conversational level, that two people are having a gathering and that when I'm speaking, I'm hosting, is a very, very interesting narrative. It changes the story of what's happening in that moment.

Paul Browde:

Yeah, and it's really helpful to practice it when you're not in a state of conflict with one another, because when you are in a state of conflict it's very difficult to surrender trying to be right, or trying to fix or trying to change the other person. But if you practice just talking about good things, if I wanted to host you into a precious moment of my life that has nothing to do with you, but that happened to me... When I was on safari and saw this incredible troop of elephants walking through the wild, and you just come in and listen, then you can get good at it. You can get good at listening to me in that way. Then when we are having conflict, I can say to you, "Can I host you right now? And let me tell you how you are occurring for me, what's happening for me about the way you've treated me. Then you can come over." It's challenging, but you can actually just listen and get it. And all there is to say when you come over as a visitor with a host is, "Thank you. Thanks for letting me know." That's all there is.

Paul Browde:

I know it's difficult. I would hate anyone to think that when I say this is something that I can just do all the time. It's a practice, just like going to the gym as a practice. Listening is a lifelong practice. I think you can probably become more conscious and maybe better at it, but you never get there. The minute you think you're there, you're not there anymore because now it's not about the unknown. It's about what you now know and that changes it.

Daniel Stillman:

But the flip side, the art of hosting, I feel like there is a, maybe it's your background in performance where you really bring an heightened state of being. I've told you this story many times, like at the end of the program we were in together, when you said, "Oh, and maybe we could talk about our personal narratives," and you talked about the importance of a personal narrative, and everyone just sort of, just settled in and perked up, and not everyone has the capacity to create a dramatic present. I don't know if it has to do with the musicality of your voice or the variance of the tones that you use naturally, or your ability to describe things as they happened with clarity, but there is something in your ability to host a story that I think is really powerful. When you're helping people with story, is it important to do work on that side of the bridge, on the hosting side?

Paul Browde:

Yeah, very much so. You can learn. I appreciate what you're saying about me, and I hear that. At the same time, I believe there are principles that can be taught about what makes a story. Just the idea that you are a host and you're leading someone, it's not just that they're there and you can go wherever you like. If you're going to tell a story, I like to think of you as an airline pilot, who's going to take off and know where you are headed. Most important thing is have a direction that you're going, and even to know you are ending, so that as you start to tell a story, you do know where you're going. Yes, there may be turbulence along the way. You may be pulled by something that arises that takes you into a different direction, but eventually you come back and safely bring your listeners into land.

Paul Browde:

One of the problems I see with stories often is that people end a story too many times, or that people end a story and then give a moral and then give a whole lecture about why the story taught what it taught, which isn't necessary. I think there are some basic principles. Then of course, connection to your own body as you tell, the use of your voice, the use of breath, the use of pause and silence, tone, volume, all these things, they're learnable and can be really helpful for people to use in learning how to really be good hosts. I love that you're seeing this as the art of hosting, because I have I've thought of the art of hosting, but I think the art of hosting is much greater than just being sensitive to your listener. It's also what kind of teller are you.

Daniel Stillman:

Yes. One thing that folks who are listening to this won't be able to see is, when you were bringing the airline pilot's mindset in, you touched the temples of your forehead and you drew the arc from the beginning to the end, the holding in your mind of the whole journey. I think there's something really powerful and profound about holding that whole arc.

Paul Browde:

When I work with people around telling their stories, one of the exercises is to come up with a last line. You don't need to know what the whole story is, but you do need to know your last line. When you speak your last line, that's it. Now that's going to be your last line. Now start and see where we go, but bring us to your last line, bring us there. There's a directionality, there's a vector in telling that really makes it more compelling, makes it more interesting to listen to.

Paul Browde:

But I'll say something more about that is, choosing a last line of a personal story is painful, because it means that you have to accept that the story's going to end and all the other possible last lines are no longer available. They're not yours. Those are different stories. I think there's sadness in that. I actually think there's grief in that, because I think that ending a story is in some ways a rehearsal for our own mortality, that we have to accept that it's going to be over. I think that's why so many of us struggle to choose the last line of the story.

Paul Browde:

I once went through a transcript of me speaking. I transcribed me leading a workshop. I was so shocked that at the end of almost every sentence, every block of speaking, I said, "And." I would speak for a while and then I would go, "and" and then I'd breathe. But the and, I realized, was a way of keeping open the possibility that I would continue. Once I was aware of it, it took a lot to stop saying that.

Daniel Stillman:

Can we tell our personal narrative when we don't know where it is going to be going, when there's so many untold chapters of our lives?

Paul Browde:

Yeah. I think to start off with, we do. We have no idea where we're going and that's where I think the listener just being present, and just the listener can also bring encouragement and just saying, "Tell me more. I'm so interested. Tell me more, tell me more, tell me more." And we start to discover our own personal stories. They don't live always at the level of consciousness. I think I'm talking about finally, when you have a story and you want to craft it and work with it and tell it, then I'm talking about some of these principles. B

Paul Browde:

ut when you're excavating a story, you're actually just trying to see what is this story, what is it about, there are no rules. All there is is just speak. The one thing I would say notice is if you keep saying the same thing over and over again. There may be something deeper if you find yourself doing that. There are phases to telling a story and the first phase is excavation, and then there's construction, and then there's mapping, and then there's delivery.

Daniel Stillman:

Yes. Paul, I'm shocked to look at the time to realize that we're coming up against our time together. I want to be...

Paul Browde:

Wow.

Daniel Stillman:

... I want to be respectful of your time and of all of our mortality. Is there anything I haven't asked you that is important to be said? What remains unsaid?

Paul Browde:

Well, no, I mean, I would love to, if anyone, I'd love to hear from people who listen to this. I'm working at the moment in three areas. The one is what we calling purposeful leadership. I'm really beginning to see that leadership is not about the role of the leader. Leadership is a way of being that is our birthright. Every one of us leads our own lives and we lead other people, and so how we are with ourselves and with other people really is the kind of leader that we are and doesn't mean standing up and being a big, powerful speaker and extrovert. It can be very quiet and it can be very internal. So purposeful leadership.

Paul Browde:

The other is the idea of bringing one's whole self to work. How do you bring your whole self into the workplace? It doesn't mean sharing every single thing that's ever happened to you, but it is about allowing your whole self to enter the door and not having to leave parts of yourself at the door because they've banished. Then the third is this idea of story as medicine.

Daniel Stillman:

Yes.

Paul Browde:

And so if anyone has anything to say, I don't know if you could say my website, but...

Daniel Stillman:

Oh, of course. Yes.

Paul Browde:

... or my email, I'd love to hear from people.

Daniel Stillman:

Where, if people want to find more about you, should they go to?

Paul Browde:

More about me is my website, which is Paul Browde, P-A-U-L B-R-O-W-D-E.com. My email is PBrowde, P-B-R-O-W-D-E @mac.com. I'd love to hear from people.

Daniel Stillman:

Well, I hope at some point we can do a part two. I feel like we literally just scratched the surface of this very vast and important topic. I'm really grateful, Paul. I'm looking forward to finding the hidden threads in this conversation.

Paul Browde:

Well, I thank you and I really appreciate your listening. I really learned something today. So there was something about your listening that allowed me to see and to hear myself in new ways, which I really appreciate very much. Love to be listened to by you more. Thank you.

Daniel Stillman:

That is such a crushingly large compliment coming from you. I really appreciate that. I'll sit with that. We'll call scene. I'll stop recording.

Conscious Co-founders

In this conversation, I sat down with my friend Doug Erwin, the Senior Vice President of Entrepreneurial Development at EDAWN, the Economic Development Authority of Western Nevada.

Doug is a former serial entrepreneur turned economic developer and executive coach, and he’s committed to growing Northern Nevada’s startup and technology ecosystem. His community work has helped change the perception of Reno and lay the foundation for future generations of entrepreneurs to thrive in the region. Doug is proud to support entrepreneurs as they embark upon their own journeys.   

Doug shares, with great clarity, vulnerability and humility, his entrepreneurial journey and some key lessons he’s learned along the way.

I invited Doug to have a conversation with me about what it might mean to be a conscious cofounder, given Doug’s personal work on mindfulness. Towards the end of the conversation, we arrive at the idea that we are our own most important cofounder - the conversations we have with ourselves will either lead us to lean into or turn away from challenging conversations with our cofounders. And with the lens of Triple Loop Learning, we can start to create better cofounder relationships, not just with better contracts and financial structures, but from our way of being.

The basic metaphor is this: Work is a relationship. And relationships are made of conversations.

And you can hear this in Doug's description of a company as a “rebound startup” or talking about startups like a marriage.

And just like in personal relationships, sometimes, as Doug says, people want to turn away from the discomfort of having difficult conversations.

Doug mentioned research about splits among founders and how it related to the future success of the company. I did a bit of digging and... It’s counter-intuitive, that a startup with equal distributions is a red flag to investors, and that such a company is more likely to fail.

Doug suggests that unequal distributions are proof that the founders have had some hard conversations - which is a key skill in work and life.

However, roughly three out of four startups decide to split the business equally when they start up.

One of the main issues with this approach isn’t a question of HOW to make the split, but WHEN. A 2016 HBR article suggests that founders should wait to split shares until later, co-creating rules to determine the value of various contributions. (I recommend the book Slicing the Pie!).

The HBR authors suggest that “teams that negotiate longer are more likely to decide on an unequal split: the harder you look, the more likely you are to discover important differences. More generally, [they] argue that if cofounders haven’t learned something surprising about each other from their dialogue, they probably haven’t engaged in a serious enough discussion yet.”

The HBR article suggests that a hastily created equal split will sour over time - the percentage of founders who are unhappy with their split increases by 2.5x as their startups mature. That discontent can lead to rapid turnover, which can be problematic.

Another study, led by Professor David Noack, Executive Director of the Hall Global Entrepreneurship Center at the Goddard School of Business and Economics at Utah’s Weber State University suggests that an equal split, especially in early-stage companies, has another unexpected effect - making it unclear who’s driving the bus. According to Professor Noack’s research, if no one feels that they have ownership and responsibility, no one takes the wheel, which has a real effect: 

Companies with an unequal split were 21.7% more likely than other firms to be up and running a year later.

And just like in a marriage, having a “pre-nup” conversation can be awkward, even when people know the data about divorce. 

While it’s uncomfortable to do so, hosting a conversation to explore all the negative scenarios that might occur in the future, with corresponding actions to help avoid them, can help founders avoid headaches later on…and increase startups’ chances of success.

This is a conversation worth listening to…And I’m excited to share it with you!

Links, Quotes, Notes, and Resources

EDAWN - Startup Reno

Growth Pioneers Podcast

Minute 2

Daniel Stillman:

So for somebody who is starting down the path to entrepreneurship and is starting something out, what kind of advice would you give to them in terms of hosting a valuable, worthwhile, powerful conversation with somebody that they want to be a co-founder with or a partner with in an endeavor like building a thing?

Doug Erwin:

Yeah. Yeah, no, that's a great question. I think there is a bit of this myth of the solo founder in our world. Hopefully that's being dispelled. I mean, that does exist still, but a lot of people... I heard this flippantly that to create a startup company, you need a hacker, a hipster and a hustler, right?

So you need these three different people that make a startup work. But at a minimum, a lot of these companies are going to have partnerships. The way I look at that honestly, is I look at it as a marriage. You're about to embark on a life journey with someone for a long time and you're going to spend a huge amount of time together. And so, to at least treat at the same level of seriousness that you would a marriage.

Minute 6

Doug Erwin:

But the fact was, the founders that had unequal distributions had those hard conversations. You might go through that whole conversation list and say, "No, actually look, we're all contributing equally." And that's fine, but it was really indicative of like, "Let's actually have the hard conversation up front. It's sort of like, I mean, when is the best time to discuss divorce? When you're getting married, you know? When the things are good. No one wants to talk about divorce, but it's best to talk about the challenging times when things are good, because there's less at stake at that point. And so I think that it's like being very intentional upfront.

Minute 28

Doug Erwin:

But I mean, the reality of it is most startups fail. I mean, that's the truth of the matter, right? And to deny that is to deny just math. And so I think... It doesn't-

Daniel Stillman:

Yeah, not always a good path.

Doug Erwin:

No, not a good path. No reason to be in conflict with reality. The greatest suffering is when you're in conflict with reality. Now again, I know people don't want to jinx it or put some negative energy into it, but just having those, it's almost like how we talk about it when you want to have the money conversation one time. If you can just sit down and lay out, "This is what it looks like. This is how we break up." Now it may not be that way, but at least you've had that. It's there. It's filed. It's in the documents. And you just know that it's there and hopefully you don't have to go through it. I mean, when you buy a new car, you're really excited about a new car. You still buy insurance.

Minute 39

Doug Erwin:

I think so much of that is getting your own alignment around what you really want to create in the world, right? This is creating from an intentional place. And then also linking that with the reality. I think so much of that is those limits. Finding the right capital structure for your company is just aligning what you're trying to create in the world with the right form, right?

If you're going to go create a biotech company and you think you're going to bootstrap it, probably not likely given how much money it costs. Or if you're going to start a boutique in Midtown and you think you're going to get a bunch of angel investors or venture capitalists, that's the wrong form as well. But just aligning that and getting really clear about what your long-term goals are and then fighting the right form to match the essence of what you're trying to create.

More About Doug

Doug Erwin is the Senior VP of Entrepreneurial Development at the Economic Development Authority of Western Nevada (EDAWN), and a former serial entrepreneur turned economic developer and executive coach. Doug is committed to growing Northern Nevada’s startup and technology ecosystem and supporting entrepreneurs as they embark upon their own journeys. Doug’s work in community has helped change the perception of Reno and lay the foundation for future generations of entrepreneurs to thrive in the region.

Full Transcript

Daniel Stillman:

So we're live.

Doug Erwin:

We're live. Okay. Well, let's do it.

Daniel Stillman:

Doug. I want to officially welcome you to The Conversation Factory, and I'm grateful for this time.

Doug Erwin:

Me too, Daniel, I'm really grateful to have some time to chat with you. I really appreciate our friendship and what you're doing in the world.

Daniel Stillman:

And I'm inviting myself to slow down a little bit, because I think that's something that you're really, really good at doing and always reminding me that that has value. And so the reason why I wanted to have this conversation with you is because of your wealth of knowledge and experience around making businesses in both good and bad ways and because of your work at EDAWN. And so I'm hoping. For the folks who don't know who Doug Erwin is, can you give us the being, thinking, and doing of who you are? What's your essence?

Doug Erwin:

Sure. Yeah, no, I'll do my best to put in that context. Now I sort of describe myself as a serial entrepreneur turned community developer. Over the years, I've had a lot of different entrepreneurial experiences, but for the past 10 years, I've dedicated my life to helping develop the Reno startup ecosystem. And so kind of really building on my own challenges as a startup founder, my own experiences growing up in the Silicon Valley ecosystem and then really trying to bring those lessons to bear at a community level through EDAWN, which is the Economic Development Agency of Western Nevada. So for almost 10 years now, my sole focus has been on supporting entrepreneurs and growing a community of support so that entrepreneurs can find success in Northern Nevada. And then of course you and I have known each other. I've sort of built upon that over the last few years. Got really interested in doing more deep personal work, and so we went into doing some executive coaching where I mostly work with entrepreneurs and founders.

Daniel Stillman:

Nobody can do anything on their own. I think this is where the foundation of this conversation comes from me. I think we always have to bring other people into the creative conversation, whether it's enrolling people to our mission and vision, or literally splitting up the work and/or bringing on a co-founder or an employee. And I feel like there's always something gained from bringing someone to the creative conversation. And then there's always tensions because each party in that creative conversation can want to take things in a different direction.

Daniel Stillman:

So for somebody who is starting down the path to entrepreneurship and is starting something out, what kind of advice would you give to them in terms of hosting a valuable, worthwhile, powerful conversation with somebody that they want to be a co-founder with or a partner with in an endeavor like building a thing?

Doug Erwin:

Yeah. Yeah, no, that's a great question. I think there is a bit of this myth of the solo founder in our world. Hopefully that's being dispelled. I mean, that does exist still, but a lot of people... I heard this flippantly that to create a startup company, you need a hacker, a hipster and a hustler, right?

Daniel Stillman:

Right.

Doug Erwin:

So you need these three different people that make a startup work. But at a minimum, a lot of these companies are going to have partnerships. The way I look at that honestly, is I look at it as a marriage. You're about to embark on a life journey with someone for a long time and you're going to spend a huge amount of time together. And so, to at least treat at the same level of seriousness that you would a marriage.

Daniel Stillman:

Yes, totally. I think one of the tensions I've found is when something's new, you don't know what it's going to be. When something's new, it can feel like putting a lot of heavy weight onto those conversations can feel like a burden. So how do you find that balance? How would you suggest to somebody that they find that balance between the sort of robust depth of the conversation and the like, "Let's get it started, let's be agile and let's move quickly."?

Doug Erwin:

Yeah. No, that's a great question. One of the things that was really helpful, I can't remember exactly where the data was but I think it was Kauffman Foundation, looked at the success of companies, startup companies based on the founder share allocation. And so the companies that the founders had equal share distributions performed much worse or worse than the ones where they had uneven distribution. And so this was a little kind of like, why is that true?

Daniel Stillman:

Yeah.

Doug Erwin:

And fundamentally, I think the answer to that question is they had the hard conversations up front that said "My contribution is this. Your contribution is that. How does this work?" Those founders went through and said, "Okay we all are bringing different things to the party. How do we create an equitable distribution for that?" And so what their point about that was those founders already had established the right type of relationship, such that when hard times came, they could already face some of those challenges instead of like, "Oh yeah, yeah. We're all 1/3 partners." And so they didn't really create a structure to have those difficult conversations. And when things happen that are hard, which they always do at a startup, Then they have less resiliency to navigate through that.

Daniel Stillman:

That's so interesting and that is counterintuitive. I would think that if people are equal partners and see themselves as equal partners, that that would create more, more buy-in. But what you're saying is being clearer about who's contributing what and what the value of that is to the success of the company, it may not be equal.

Doug Erwin:

It may not be, and I'm not even sure that the real takeaway point was the share split. But the fact was, the founders that had unequal distributions had those hard conversations. You might go through that whole conversation list and say, "No, actually look, we're all contributing equally." And that's fine, but it was really indicative of like, "Let's actually have the hard conversation up front. It's sort of like, I mean, when is the best time to discuss divorce? When you're getting married, you know? When the things are good. No one wants to talk about divorce, but it's best to talk about the challenging times when things are good, because there's less at stake at that point. And so I think that it's like being very intentional upfront.

Daniel Stillman:

Yeah. So what would you advise or coach someone who's got a co-founder who's like, "I don't want to have all that negative scenario planning"? Because it really is. I mean, I remember going through that, sitting down with a lawyer and being like, "Okay, so if this happens, if this happens, if this happens, if this happens," and you're like, "Wow, this is getting pretty dark pretty fast."

Doug Erwin:

Yeah. Yeah. I mean, it's a difficult one, because I mean most people want to turn away from discomfort. I mean, I don't know that I have brilliant wisdom. I think there was another... I don't know who said it, but it's like contracts keep friendships. I'm not totally sure that's been my experience, but at least if it's laid out. I've had a couple personal experiences where I've had co-founders and it hasn't come together the way that we thought. Both cases I did not have contracts. And so it left a lot for interpretation. It maybe my fantasy about this, but I think there would be reality to it. It would've been much clearer if we had a buy-sell agreement or some other mechanism that said, "Hey, look, if we need to get out for whatever reason, this is what it looks like." Because in the moment there's a lot of emotion which leads, in my experience, to irrationality and lots of hurt feelings and other challenges.

Daniel Stillman:

Yeah. If you feel comfortable, I'd love to unpack, maybe give some more color to that challenge for you.

Doug Erwin:

Yeah. Yeah, for sure. Well, I have two examples where I was a co-founder. The one that was probably the most challenging of the two was my first real startup endeavor, which is a company called Pria Diagnostics. We built an at home male fertility test kit. The co-founder was my brother, which brings in a whole other element of complexity. He brought me into the company. He was a PhD out of Stanford. It was technology that came out of Stanford. I was really the only entrepreneurial guy he knew that he trusted. And so we came together in that. We ran that together for about eight years. We went and raised a bunch of angel money. We set up a bunch of partnerships.

Doug Erwin:

At some point our core product just wasn't going to work in the market, and so it started to unravel. We lost our key partnership. We needed to try and pivot, but it was 2008. Lots of difficult financial situations. And in that situation, basically he, after we'd laid off a big portion of the company, decided to go, leave and start something else. It was supremely challenging for me. I mean, I'll fast forward to it. Thankfully he and I have worked through that and there is a happy story here, which we're close and our kids are close and all of that. But for many years we were estranged. And so much of that honestly, for me, if I think about it was a lot of the expectations I had and these ideas that he and I were going to work together forever, like we were going to work together on these multiple startups. This was the first of that. And the hardest part about that for me was just that shattering of that fantasy.

Daniel Stillman:

That's brutal. And also, I can't imagine. Eight years is an amazing run.

Doug Erwin:

Yeah, it is.

Daniel Stillman:

An amazing amount of intimacy with your brother. And then the business breakup, him wanting to leave must have been really hard to deal with.

Doug Erwin:

It was very difficult. It was a combination of that. And then I was the CEO, but we had got down to like, we went from 27 to four or five people. The COO, in order for him to stay, he needed to become the CEO, but then ultimately I got the deal close. So there was, for me personally, just a lot of status, social status, estrange from brother, and then of course I didn't have any very good coping skills so that led to some personal challenges. I was drinking too much and just... It was not a good situation. Although of course upon reflection, it's the best thing that ever happened, it taught me so much. But in the moment, it was very challenging. And so much of this, I guess for me, was around unspoken expectations.

Daniel Stillman:

Right.

Doug Erwin:

We didn't have a language to discuss it. When he left, I felt abandoned by him.

Daniel Stillman:

You had no allowance for him for an exit for him before you would had sold the thing. That was presumably going to be the exit.

Doug Erwin:

Correct. Yeah.

Daniel Stillman:

So what do you think kept you from having some of that worst case scenario early on?

Doug Erwin:

A naivete. I mean, I think I was 29 when we started that company. He and I had been through a lot together, right? He's my stepbrother. We went to college together. We moved to the Bay Area together. There was just all of this implicit trust. Not once did it ever cross my mind that we needed to even have that conversation.

Daniel Stillman:

Yeah. Yeah. There's this unspoken trust, which is we should take for granted and we assume that it will always be like this.

Doug Erwin:

Yeah.

Daniel Stillman:

And because of that, we just avoid having the difficult conversation because I mean I guess it didn't even occur to you. But then when you get towards the middle of the downward arc, the beginning of the end, the end of the beginning, I don't know, when did you realize there was some trouble that you needed to start having these difficult conversations?

Doug Erwin:

Yeah. Of course we were also living together at the time, so I was living in his spare bedroom because I was in Reno and he was in the Bay Area.

Daniel Stillman:

Oh, my God. Talk about entanglement. Oh my God.

Doug Erwin:

Oh yeah. No, I remember that we were in the couch in his living room one time having a pretty heated argument and his wife was basically saying, "Hey, you guys got to work on some things." But again, it hadn't dawned on me that that was an outcome. I just thought that we were just going through something challenging. And again upon reflection, I think it was the right choice. I mean, it was definitely a difficult one and he needed to go move on. And in many ways, he may have been protecting me because ultimately I was CEO and I probably needed to go, but I had so much of my own identity wrapped up in that. And so I've looked at it from many lenses. There was definitely warning signs, I just wasn't aware and I was in denial.

Doug Erwin:

Just to add insult to injury, one of the things I'm very sensitive to with entrepreneurs is right around 2005 I won the Entrepreneur of the Year Award for the state of Nevada, which was this awesome... I got this great accolades. And at the same time the company was imploding and I knew it. Our partnerships were on the rocks. And so this dissonance between being put up on this pedestal and knowing things are crashing was brutal. So yeah, there was a lot packed up in that one.

Daniel Stillman:

It's interesting to think about like... It sounds like you've done a lot of work on looking at that past version of you. I'm hearing empathy for yourself.

Doug Erwin:

Yeah.

Daniel Stillman:

He wasn't asking... Oh yeah, sorry. Go ahead, Doug.

Doug Erwin:

Well, no, I just think one of the things, I mean for the longest time and our mutual friend Robert really helped me with this is I walked around thinking that was a failure. The most powerful reframe, the thing that it really opened up for me was like, no, it's not a failure, it was a lesson. And then when I really started to dig into the lessons, to create a lot of compassion. And that's why I said I honestly wouldn't have traded it for anything. I mean, I don't prefer not to go through that again.

Daniel Stillman:

Yeah. Fair. Well-

Doug Erwin:

But...

Daniel Stillman:

Yeah?

Doug Erwin:

It was worth it.

Daniel Stillman:

Yeah, because you were willing to learn from it.

Doug Erwin:

Yes.

Daniel Stillman:

What do you feel like when you went into your second big startup? What do you feel were lessons you took forward in the early stages of that one? Did things change for you?

Doug Erwin:

Well, so [inaudible 00:16:03]-

Daniel Stillman:

Did it take you longer to learn things?

Doug Erwin:

Yeah. If I was to summarize that startup, I would say it was a rebound startup. It was kind of I had this... I think my ego was very bruised. It was very difficult time. I think the guiding and thinking in my mind was I've just got to get back on the horse that kicked me. All of my identity was wrapped up in being an entrepreneur. I was in Entrepreneurs' Organization which I think is an amazing organization. But everything around my life was around being an entrepreneur and I just needed a new idea. And so I didn't spend a ton of time looking into the new ideas. And I ended up starting a standup paddleboard company. I co-founded a company called Tahoe SUP. So going from medical devices to consumer sporting goods is kind of a strange transition.

Daniel Stillman:

But also given... What year was this? I mean, I remember standup paddleboarding was exploding at one point.

Doug Erwin:

Oh yeah. We were early. It was like 2009.

Daniel Stillman:

And for people who don't know, I remember meeting this couple who did standup paddleboard stuff in the Rockaways. I did some standup paddleboard yoga, which is super fun. Because I'm really bad with inversions and it's just so fun to know you're just going to fall in. But these people were doing competitive... I was like, "There's competitive standup paddleboarding?" It blew my mind because I think of it as this relaxing sort of endeavor, but no, there's competitions. People take this shit real.

Doug Erwin:

Oh absolutely. And we were so early. I mean, if you ever read the book Blue Ocean Strategy, it was like a perfectly executed blue ocean strategy even though I didn't know that's what we were doing. At that time all the standup paddleboards were coastal and here we are in Tahoe and we created the whole category for touring boards and recreational paddleboarding. So very different board design, totally different messaging. Our tagline was, "We're not in it for three second thrills. We're in it for day long adventures." It was just a completely different way of looking at paddleboarding. And so it was amazing. I mean, we went from nothing to $3 million in sales in like a year and a half and was like a rocket ship. I mean, not a tech rocket ship, but nevertheless, a pretty big rocket ship at that time.

Daniel Stillman:

Yeah. A business is a business as far as I'm concerned.

Doug Erwin:

And in that situation, I joined a co-founder. Again, I didn't really process the learnings. I mean, I think I processed it a little bit, but I didn't really put it into action. I think one of the things was still in this... There's something about being a young entrepreneur where at least for me there's just a lot of youthful exuberance and you can really drive on that and that naivete gets you a long way, but ultimately you have to have some wisdom. And so I just think I was just trying to get right back up on that horse that kicked me off. And so we created a partnership that was really set up for failure probably from the day one. I brought in one of the investors from my other company, lovely woman, but was probably not her industry. And so we had this three way partnership between myself, this woman, and this other gentleman. It just was fraught from problems from day one. It kind of plagued us the entire time of the company.

Daniel Stillman:

Really? Is it okay to say a little bit more about what was off about the way you had partnered?

Doug Erwin:

Sure. I think there was a little bit of unequal power dynamic. The co-founder who really was the person who had the idea didn't have any capital and was sort of first out. So we brought in some capital and some business advice or expertise and he brought in all of these skills. And so there was a... I think he always sort of felt maybe like he wasn't unequal footing. I felt that partnership was... There's a lot of passive aggressive behavior going on. There wasn't a lot of communication. And almost from the very beginning we had to do a lot to try and keep the partnership functioning. It became a lot of work. There was just so much operational overhead that it was very distracting.

Daniel Stillman:

Just to keep the peace between the three of you.

Doug Erwin:

Just to keep the piece. Yeah, between the three of us.

Daniel Stillman:

I mean, I feel like this brings up the question of like, whether or not the people who are in partnership are doing their own work on themselves and are working with their shadows and their denied parts, their feelings of inadequacy or guilt or all of these pieces that we're bringing into a relationship.

Doug Erwin:

Well, I can just say at least for me, because that was in 2009, I hadn't even really started on my own spiritual personal development journey at that point. So I think my strategy for dealing with pain and complexity was drinking. I had started a little bit as a result of-

Daniel Stillman:

Was it an effective strategy at the time?

Doug Erwin:

Of course not.

Daniel Stillman:

No?

Doug Erwin:

I mean, it temporizes things. I was just in the beginning stages. I mean the Pria breakup sent me down a path that I just... I remember I was in Belize. I found this book in the airport of San Francisco called The Secrets to Happiness. It was like a one paragraph on all of the spiritual and philosophical traditions. I'm reading this, licking my wounds in Belize, trying to figure out what I'm going to do, and I was like, "I think Buddhism is the answer." And that's where it all started for me. But I was very early on in that I had no real training or understanding. I was working with my own therapist to unwind all of my own challenges. So I definitely was working through that at the time. But it was very early for me, so still leveraging former strategies. I had the pain and I wanted to try and avoid a few things, but fundamentally I was probably using the same strategies.

Daniel Stillman:

Yeah. I mean, because from what you're telling me about your co-founder who had the idea but not the money, I could really empathize with that position of like, "It's my idea" and the feeling of pride in that and the feeling maybe of shame or embarrassment or weakness that I didn't have the money to make this happen, that I have to rely on these other people. Instead of it feeling like a real partnership, it can feel like an unhealthy dynamic.

Doug Erwin:

Yeah. We were sort of bringing a tech startup approach into really a manufacturing business. I mean, one of my biggest takeaways from that was matching the right capital to the type of business you had. I mean, we were literally looking at this as an angel funded, high growth tech startup, and this is much more of like factory receivables and industrial manufacturing. It was just a different animal. I think there was just some inherent misalignment that. So I think that was definitely challenging. But I'm with you. As I think back on our co-founder's experience, I could imagine... The plus side of that whole thing is he ultimately ended up with the company. It's been sold a few times, but I think as of even last month, the company's still in business, he's running it. It's been a long journey to get him there, but it was ultimately the right fit. That one actually had a very positive outcome for me, meaning I got out without too much damage. The company went through a lot of damage, which is unfortunate, but the product exists and I learned a lot of lessons from that.

Daniel Stillman:

I think we only have a little bit of time left so I feel like one of the most powerful frameworks that I learned from our coach Robert is the very unique application of triple loop learning and that many people think about transformation just from the perspective of doing things better, but not realizing that requires us to think differently in order to do differently. I think a lot of advice out there falls under the do and think categories and ignores the triple loop of how do we be in order to think in these ways. Because the early advice you gave of at the beginning... In sales it's such simple advice. Just at the beginning before things get super hard, have the deep dive conversation about all of the scenarios and then work out the partnership deal in accordance to that conversation.

Daniel Stillman:

Now that's a pretty basic advice. And by basic, I mean basic like, "Yeah, basic." I mean basic like "Yeah, that's it." But unless I'm willing to be a certain way, I can't invite that conversation. And so I think that's maybe where the real transformation comes in. How shall we be in order to be able to invite and host this kind of a conversation in a powerful and effective way from your experience?

Doug Erwin:

What's coming up for me is really turning into what was uncomfortable. Like being okay with sitting with discomfort. There's so much excitement and exuberance when you're starting a company. There's so much potential. And that feels really good. That's such an uplifting energy. And so the idea of talking about what it happens if it doesn't work out is sort of the opposite of that. And so in that beginning phase, you sort of feed on that energy. At least I did.

Daniel Stillman:

Yeah.

Doug Erwin:

But I think it's sort of, again, recognizing that turning towards something that may be dark or uncomfortable is actually warranted, A, and will not diminish the light. There's so much light.

Daniel Stillman:

I think that's the fear, right? Certainly I've read way too many articles about the power of Steve Job's reality distortion field and how impactful that was to getting amazing things done and how entrepreneurs really create the future through this will. I think there is this real fear that if I step back and look at the discomforting possibility of failure and look at everything that could go wrong, that it will erase the light. But you're saying it doesn't have to be that way.

Doug Erwin:

I don't think it has to be that way. I think that's probably why people avoid it.

Daniel Stillman:

Yes.

Doug Erwin:

But I mean, the reality of it is most startups fail. I mean, that's the truth of the matter, right? And to deny that is to deny just math. And so I think... It doesn't-

Daniel Stillman:

Yeah, not always a good path.

Doug Erwin:

No, not a good path. No reason to be in conflict with reality. The greatest suffering is when you're in conflict with reality. Now again, I know people don't want to jinx it or put some negative energy into it, but just having those, it's almost like how we talk about it when you want to have the money conversation one time. If you can just sit down and lay out, "This is what it looks like. This is how we break up." Now it may not be that way, but at least you've had that. It's there. It's filed. It's in the documents. And you just know that it's there and hopefully you don't have to go through it. I mean, when you buy a new car, you're really excited about a new car. You still buy insurance.

Daniel Stillman:

Yes.

Doug Erwin:

You're going to get an accident. It's kind of in that vein.

Daniel Stillman:

I love this mindset of having it one time. I mean, I don't know if that's actually accurate. I feel like we generally have to revisit these conversations, but I like the idea of saying like, "Let's set ourselves up for success by building a platform and a foundation. Let's have this conversation." So I'm thinking of these two ways being of like, "Let's turn into discomfort and the willingness to do that." And the, "Let's really build a platform. Let's have this conversation. Let's have it one time." I mean, I think that's a little idealistic, but I think it's a nice way to... It feels like a very encouraging way to start, like, "Well, let's just have this one time." And it may be enough if you really have it in the right way. Maybe it is enough. Maybe I've just never been doing it right, Doug.

Doug Erwin:

Well, one time again, maybe idealistic, but at least you're getting it out in the beginning and it's being codified in whatever documents and you have an agreement. It's like how do we create an exit plan broadly? I mean, obviously if it comes up, you can never capture everything, but at least you have a framework for it so that everybody's in agreement and they know what it's going to look like. I mean, it's going to be uncomfortable if the founder relationships break up regardless, but I think having the conversation up front can make it less uncomfortable.

Doug Erwin:

Plus not to mention I can't tell you how many times I've seen these deals where people come in. Forget about the breakup, they just don't even have stock purchase agreements and things like that. So I've seen more than a few deals where a co-founder exits with all of their stock, and that pretty much kills the company's ability to go raise a future round of financing. And that scorned founder holds a lot of power over the deal. That is just not a good deal. It's a very novice deal that shouldn't happen, but I've seen it happen more than a few times.

Daniel Stillman:

Well, do you mind? I mean, this sounds like worth getting into the weeds a little bit, because I imagine that founder who wants to leave wants to take their investment and their capital with them. How do you balance the needs of the company as a whole and the future of the company to the desire of somebody to keep what was "theirs"?

Doug Erwin:

This is a great question. I think it really comes back to what type of company you're structuring. So if you're going to build a company that's going to take outside investment, by definition you are going to be selling equity over some period of time, generally speaking if you're building a high growth company. Any of those companies, the founders, the intellectual property, all of that really is property of the company. Any equity you have, generally speaking, would be earned out over a period of time. But you can see sometimes naive founders or people that go through that process end up with like 30% to 40% of the company, but have not agreed to be under a vesting agreement or something like that. When they leave they're fully vested and they can take all those shares. And that just creates... I mean, even worse if they don't have an assignment agreement, they haven't assigned their property. I mean, you would think that wouldn't happen given all of the accelerators and things, but I have seen it more than you know.

Daniel Stillman:

So if you were... Yeah, sorry, go ahead.

Doug Erwin:

Well, and I think that's maybe a little bit different. I mean, it would definitely be different if you're building a brick and mortar store or something like that where maybe you're not necessarily building it for outside investment from day one. But in a lot of cases, people maybe structure something originally, "Hey, we're doing this one thing" and they shift it to another thing and they just keep operating like that. Who likes to spend money on attorneys? Nobody.

Daniel Stillman:

Show of hands in the audience.

Doug Erwin:

However, that would be the other thing, is always get the right attorney in the very beginning and spend the money. No one wants to spend the money on attorneys, but getting those documents done up front save so much money on the back end.

Daniel Stillman:

Oh my God. Oh my God, I don't even think... I mean, this is my own horror story, but I think we spent a lot of time in a company I co-founded putting all those documents together and then I don't think we ever signed them. I was like, "Wait a minute. How did that happen? How did that happen?" I'm so ashamed. Did that bite me in the ass? Yes, it did. Am I ashamed about it? Yes, I am.

Doug Erwin:

It's a good lesson.

Daniel Stillman:

It's a good lesson.

Doug Erwin:

It's a good lesson. Transform that shame into a new learning.

Daniel Stillman:

So there's one other thing that I'm thinking of that sounds like from the level of mental models and being that is helpful in getting to yes in the Harvard program on negotiation they talk about creating more value and increasing the size of the pie. That it's not just splitting up the pie. Actually, I don't know if you've read that book Slicing the Pie.

Doug Erwin:

No.

Daniel Stillman:

It's a great primer on some of the stuff that we're talking about. It helped me back in the day, or at least it would have if I had signed my agreements.

Doug Erwin:

Page 1, sign the agreements.

Daniel Stillman:

Page 1, sign the agreement. Whatever you do, sign it. But I think there's this idea of like breaking up the pie. But what you're talking about, if your hope is to create a larger company over time, then there's this idea of the whole pie should get bigger through whatever it is that we do, right? There's like, "Well, this is my third." It's like, "Well, would you like 1/3 of zero? Or would you like 1/3 of 2X or 3X?" Or sorry. "Or would you like 1/5 of something that's three times as big?" It's like, well, that's a very different conversation to be having.

Doug Erwin:

Yeah, especially for high growth companies. I mean, I guess this is a real challenge with first time founders. This question of would you rather have 100% of nothing or 30% of a billion dollar company? You really have to buy into that mental model if that's the type of company. Now, it's not always done that way. There's a local company here, the founder owns 85% and he's never taken a dollar and he's bootstrapped it. That's great. He's going to be very successful. Most of them don't work that way. And so just that idea of... Well, and really, I mean, if you think about it, I mean, when you create a company, you are creating another entity altogether. And ultimately that entity transcends the founders, right? It becomes its own thing. I mean, we don't even need to get into politics, but I mean, the fact that corporations can be involved in political things, all that is just another example of the fact that they are their own entities. And so what you're really doing is how do I best-

Daniel Stillman:

Yeah. We could talk about whether or not that should be there.

Doug Erwin:

No. Yeah, yeah. That's a [inaudible 00:36:38]-

Daniel Stillman:

We should definitely get less corporate money in politics.

Doug Erwin:

Totally.

Daniel Stillman:

We'll have another podcast about that.

Doug Erwin:

We should make that one longer.

Daniel Stillman:

Yeah.

Doug Erwin:

But I mean, a bit fundamental, you're creating this entity. And so what's in the best interest of this entity that's going to most likely outlast the founders?

Daniel Stillman:

See, that's a very different level of thinking and being, right? It's like, "Well, I want my 1/3" versus, "What's going to create the long term health and wellbeing of this thing that we're creating together?"

Doug Erwin:

But I also think that starts with the intention of what you're trying to create, right?

Daniel Stillman:

Right.

Doug Erwin:

And so we're largely talking about venture funded startups. I mean, there are other companies that are multi-generational. And so I think in that very beginning, what are you trying to create? What do you really want to create and how does that business best align with your desires?

Daniel Stillman:

So when it comes to facilitating, leading, or coaching others or yourself through this conversation, I'm hearing some really powerful questions that we should be asking ourselves, right? What are we really trying to create, right? Am I going to put my needs over the needs of this thing that we're creating together? How might we turn into discomfort? My mom, I quote my mom I feel like in every podcast, partly because I know she's going to listen to the episode. Hi mom. She always says, "Start as you mean to continue," which is a very profound idea.

Doug Erwin:

Wow.

Daniel Stillman:

And it's like do you want to have a relationship where you can't talk about the hard things? I mean, nobody would cop to that. And yet we find ourselves backed into a situation where it's uncomfortable to bring something up. And so if we don't bring it up, it won't be brought up.

Doug Erwin:

Well, first of all, I'd like to meet your mom. She sounds like a wise, wise person.

Daniel Stillman:

Oh, you would love my mom.

Doug Erwin:

A wise person.

Daniel Stillman:

My mom would love you too, 100%. Mainly because she... All the spiritual stuff we talk about, she's the source.

Doug Erwin:

Yeah, I know.

Daniel Stillman:

She's the source of many of theses things.

Doug Erwin:

I appreciate that.

Daniel Stillman:

You should go straight to the source, not through the conduit.

Doug Erwin:

No, I appreciate all that. I think so much of that is getting your own alignment around what you really want to create in the world, right? This is creating from an intentional place. And then also linking that with the reality. I think so much of that is those limits. Finding the right capital structure for your company is just aligning what you're trying to create in the world with the right form, right?

Daniel Stillman:

Yeah.

Doug Erwin:

If you're going to go create a biotech company and you think you're going to bootstrap it, probably not likely given how much money it costs. Or if you're going to start a boutique in Midtown and you think you're going to get a bunch of angel investors or venture capitalists, that's the wrong form as well. But just aligning that and getting really clear about what your long term goals are and then fighting the right form to match the essence of what you're trying to create.

Daniel Stillman:

So you mentioned mindfulness and we're talking about form in essence. And so I'm wondering with literally our last few minutes, because you do a lot of work on mindfulness and you also coach people on essence, where do you feel mindfulness and being aware of our essence comes into this conversation about being a conscious co-founder?

Doug Erwin:

I mean, to me it feels like table stakes. How do you not have mindfulness if you're going to go into something consciously? And knowing what your own motivations are, understanding your having your own relationship to your mind, I mean, I don't know, this sounds a little cheesy, but that's the most important co-founder you need to have a relationship with it, which is your mind.

Daniel Stillman:

Oh, man. Wow. I mean, we were talking about this last weekend, this Carl Jung quote which I will mangle that until you make the unconscious conscious, it will rule your life and you will call it fate. I think that's the...

Doug Erwin:

Yeah, no, I think you're on it.

Daniel Stillman:

I mean, that's what you're talking about. Your mind, what we're working with here, is what we're bringing into the conversation. And we have to have that conversation with ourselves. What do I want? Am I working against myself?

Doug Erwin:

Absolutely. When I think about my own... I remember the first time I recognized mindfulness and it was in the midst of all the trauma of Pria failing. It was just a glimpse, but it was really powerful. But just knowing how my identity and all of my actions were completely unconscious, only upon reflection have I been able to do that. And now that I have a strong practice, I have a much... I mean, I'm not perfect in any regard with regard to this, but I see much more alignment with my actions and my intention and what I'm really trying to create. I think that was the first thing. Again, using Robert's frame, my first company's worked absolutely built based upon status seeking, scarcity and survival. Absolutely. I was fortunate to get an opportunity to go to do community work and create a whole startup community. And it gave me a lived experience of building from a place of abundant service and trust. And of course, and then ultimately understanding my essence and all of that.

Daniel Stillman:

Yeah. Well, we're almost out of time. Is there any parting thoughts, anything I haven't asked you about this topic that I ought to have asked you?

Doug Erwin:

I think that we've covered a lot of ground. Again, I think the most important co-founder is your own mind, like really getting clear with what your intentions are and understanding that. And again, turning towards everything. Again, just taking Robert. It's so much easier to turn towards it in the beginning when things are good and when things are difficult.

Daniel Stillman:

Yes. Well, that's really powerful, man. Thank you so much for making this time. I know you've had a very, very big week and you're about to head on vacation, so I'm not going to keep you here any longer. But I'm really grateful for your time, Doug. It's really great to hang out with you and have this conversation.

Doug Erwin:

I really enjoyed it, Daniel. Thank you so much for having me in your podcast. It's just an honor to be in relationship with you, my friend.

Daniel Stillman:

Thank you. Likewise, brother.

Doug Erwin:

Yeah, [inaudible 00:43:52].

Daniel Stillman:

We'll call scene.

Doug Erwin:

Awesome.

Prototyping Partnerships

How do you make a friend?

How do you become lovers with someone?

How do you become business partners?

In RomComs, there’s a “meet-cute”...the hilarious and unlikely way two people in this topsy-turvy mixed-up world collide and fall madly, rapidly in love. 

In the real world, taking time and gradually testing, trying and yes, prototyping a relationship is ideal. In love, we call it dating. There’s no good word for “friend-dating”, especially when you’re doing it with someone of the same sex. 

And with founding a company…where does the conversation start?

In this conversation, I sit down with Jane Portman and Benedikt Deicke, co-founders of Userlist, on how they connected through shared communities, and learned how each other really worked through real-world, previous projects.

They also share their insights on setting the stage both for a long-term vision for building a company AND for a possible exit from a partnership through thoughtful conversations.

Userlist is a tool for sending behavior-based messages to SaaS customers and recently completed a pre-seed round with 21 angel inventors.

Benedikt is a software engineer from Germany who loves to plan, build, and grow web applications. He co-hosts the Slow And Steady Podcast and organizes the Femto Conference, a tiny conference for self-funded tech companies. Jane is a leading UI/UX consultant specializing in web application design, and has been the host and founder of the  UI Breakfast podcast since 2014 (she kindly invited me to join her show in early 2022).

Enjoy my conversation with these two delightful co-founders as much as I did.

Links, Quotes, Notes, and Resources

UI Breakfast

Userlist

benediktdeicke.com

Better Done than Perfect podcast 

Jane's Story: Turning Thirty: Story of My Life

Culture, Values, Operating Principles & More

Inspire, Not Instruct: How We Do User Onboarding at Userlist

Minute 8

Daniel Stillman:

So at that moment, how did you decide to go all-in? All three of you said, "Yeah, we're going to make this happen." How did you decide to structure your relationship at that beginning stage of this new idea?

Benedikt Deicke:

If I remember correctly, Jane had that proposal and connected all three of us, and I think the first thing we did was have a conversation about what we want from this. And we did an exercise about... I don't remember the name of it, but it was something from Google Ventures about company culture and tone of voice and stuff like that just to get a feeling of we're aligned in terms of values and goals. And that was pretty helpful to get a rough understanding of each of our expectations and where we might differ. And I remember that one of the exercises was, let's plan for, "Where do you see yourself in the next five years, 10 years, 15 years?" And I think one of the learnings from that was that we were pretty well aligned in terms of expectations and goals. And that made it easier in terms of starting just together, because we knew we were on the same path and not heading in different directions with the expectations and where we wanted to take this.

Minute 15

Benedikt Deicke:

I guess one thing that was valuable in entire process of doing that, I think it was the Google design sprint exercise that we did. And having the founder agreement and just talking through all those things aligned expectations from the get-go. And I feel like that's already a good way to minimize disagreement down the road, because I feel like a lot of the fights that founders might have between each other is because they're not on the same page and have slightly different ideas about the future and slightly different expectations. And by just making sure that we're on the same page, for the most part at least, already helps with reducing the conflict.

Minute 17

Jane Portman:

To be entirely honest, all these measures and being aligned and the vesting schedule and everything, this is all great. But the biggest success factor is that we had worked together prior to that. I would not jump into co-founder relationship these days without having worked with the person. And that's the only idea how you can judge their communication, their work ethics, and a lot of other things you can never understand if you don't get involved. We were lucky that, I had not worked with Claire for example, Claire had an amazing track record as a marketer, so I just took the dive. But the relationship that now keeps working is between me and Benedikt, and we had tested it prior to starting. So I consider that the key success factor. Everything else, surely great, allows you to part ways, but at the core of it is maybe bringing somebody for money first, or somehow before trying to bring them on into the shares or something like that.

Minute 28

Daniel Stillman:

What advice would you give to someone else who feels like their co-founder isn't putting in as much as they should? It's a difficult conversation to have.

Benedikt Deicke:

But it's one you should have, right?

Jane Portman:

Even though it must be had. It must be had. This communication principle, I think I saw it in Crucial Conversations. I forgot the author of the book. It's pretty famous. Basically, you have problems with your boss, your spouse knows about it, your colleagues know about it, except for your boss. So if you feel like something is unfair, that is the conversation to have. And these fundamentals of being rewarded for your time, either with salary or with shares and keeping it fair for everybody, this is fundamental so that everybody can perform so that they feel everything is honest. Without that, without the feeling of fairness, without the fundamental of being fair, this is broken. You're feeling like you're trapped or something like that. This is not going to move forward. So it's fundamental.

Minute 34

Jane Portman:

I'd like to touch on how we do planning. And we borrowed this principle from Shape Up by Basecamp. And it says, basically, "Don't worry about your backlog as much as people do." So previously, before adopting this, we would religiously every month meet and reprioritize 60 items in our backlog. And this is just such a ridiculous activity, because in software, everything changes all the time, because you learn, you keep learning the circumstances, change, opportunities arise, things that seemed important, don't seem as important because you've learned something that is crucial to your customers in higher degree. And we just plan out the next, I don't know, let's say two, three big features. Even one, two, I would say. One, two, three, something like that.

That is true for product and for marketing, so we usually have a marketing theme direction for the next, let's say quarter or something. And there is also the things in the product that Benedikt is working on with the technical team. So there is high level roadmap, but there's definitely nothing set in stone, and we are fine with it. And that relates to that level of fluidity that we discussed. We're comfortable with that. There might be some people who are not, but works for us.

More about Jane and Benedikt

About Benedikt

Hi! I’m Benedikt Deicke, a software engineer from Germany. I love to plan, build, and grow web applications. These days, I build my own products, organize a conference, contribute to open source, and co-host a podcast.

About Jane

Jane Portman is a UI/UX consultant specializing in web application design, founder of UI Breakfast and Userlist. At Userlist, Jane's goal is to provide flawless UX and help users be awesome at their customer messaging. Jane has also been running UI Breakfast Podcast since 2014.

Full Transcript

Daniel Stillman:

Oh, my God. We're live. Welcome to the Conversation Factory you two. Thanks for making this happen.

Benedikt Deicke:

Yay.

Daniel Stillman:

Big yay indeed.

Benedikt Deicke:

Thanks for having us.

Daniel Stillman:

Yeah. It only took a couple of tries on calendar.

Jane Portman:

Thank you, Daniel. Thank you, Daniel.

Benedikt Deicke:

True.

Daniel Stillman:

So the basic question, how did you two find each other in this crazy mixed up world? I've been thinking about this idea of serendipity and how extraordinary it is that anything happens at all. So how did you two... Maybe you can introduce yourself a little bit, but I want to put it in the context of, how did you two find each other and decide to do this project, to start this thing that you're doing? That's the big question.

Jane Portman:

So we run Userlist, a software that helps SaaS companies send email automation, send email messages to their customers and leads. That is a fairly complex software product, and I'm really excited that Benedikt, the brilliant technical brain on the other side of the microphone has been on this journey. And we have known each other for 10 years, I think, roughly.

Benedikt Deicke:

Not quite, but it's getting close.

Jane Portman:

We're getting there.

Benedikt Deicke:

Yeah, it's getting close.

Daniel Stillman:

So you've known each other for 10 years, but Benedikt, when did you start thinking about what userlist became?

Benedikt Deicke:

So after meeting each other, I think we met online in a community or so, and I think a couple years after we've met at a conference and basically have been in touch after that on Twitter and social media in general. And at some point Jane was thinking about starting her first software product and was looking for a developer to work on that with her. And it wasn't userlist at the time, but in the end, I joined that project and she hired me as a developer. And in that process, we discovered that there was a tool missing in our stack that was basically userlist. So that's where the original idea came from.

Benedikt Deicke:

But it wasn't for another couple of months where we, I think, figured out that the other project we were working on wasn't quite the right thing or didn't quite work out that I think Jane, you got an inquisition offer, right? That got you thinking about moving on to the next thing. And then I think in the end, it didn't really pan out with the acquisition plan. But suddenly, there was free time and a new idea and Jane was like, "Hey, let's maybe tackle this other thing we discovered along the ride," and that's what we did.

Jane Portman:

Yes. Yes. And there were three of us in the beginning, and the second try, I thought we've got all the bases covered and we are going to skyrocket to 5K MRI in five months or so. And yeah, a lot of things went differently, but ultimately, it was a good start. And maybe today we can talk a bit more about how we can help others find their good co-founders and what's the best way to set it up, right? Because, as you can see, one of us left and we're still friends, which is a rare thing, if you think about it.

Daniel Stillman:

Very much so. I'm wondering though, I want to go back because Benedikt, this is really interesting. I think Jane, maybe you had mentioned this, that you had known each other for a while. So there was a community that you two had connected on and exchanged some messages. You sort of knew who each other were, and then you met IRL.

Jane Portman:

We met a few times at MicroConfs in Europe in person. We hang out in the same, I don't know, Slack community and definitely had a lot of friends in common. And also, my first experimental book in 2013, I think, there was a guy who bought it and I thought, "Hmm, what an interesting guy. Weird name, long hair." And then I saw his picture popping up again and again, and then we met in Prague, I think, eventually. And yeah, we met a few times.

Daniel Stillman:

Well, you wrote your book around 2014, you met-

Jane Portman:

13. 13.

Daniel Stillman:

2013.

Jane Portman:

It's nine years. Yeah.

Daniel Stillman:

Yeah. Wow. And then you had a couple of interactions in real life, and it was just friendly, collegial, I guess you might say.

Benedikt Deicke:

Yeah.

Jane Portman:

There's great spirit in the startup community, around this ecosystem of raw balling startup for the rest of us, MicroConf and now Tiny Seed, a lot of fellow founders, I was a consultant serving them design, Benedikt was a consultant serving them-

Benedikt Deicke:

Development.

Jane Portman:

... engineering. And also, Benedikt had his own product back then. Was this nice vibe going on. But yeah, when I was looking for a developer, another friend of mine said, "Well, if Benedikt suggests his help, go take it. He's the best you can find." So I did.

Daniel Stillman:

That's amazing.

Jane Portman:

And I really took him up on the deal. I really took him up on the deal, because, well, I'm a non-technical founder and I didn't have massive budget back then in 2017, I think, in the fall. Or actually 16. That was the fall of 16, I think.

Benedikt Deicke:

Right. Yeah. Yeah.

Daniel Stillman:

And so you had this moment where you were like, "Okay, this is..." So Benedikt, you were saying that Jane, you had got an offer for that company that wound up not working out, but it got you thinking, "We should start thinking about the next thing," and that seed of that next thing was inside of what you had been building together. Yeah, we can't see video, but she's waving her head, so I didn't get it quite right.

Jane Portman:

We just discovered a gap in the tools that can be used for running a SaaS. Back then, there was, at least in my head, I could only see Intercom that could send both email and in-app notifications based on user behavior. Also, this problem of... When Benedikt helped me launch the product, was a launch day and I realized we don't have a dashboard and building one takes money and time, and how can I see who my customers are? Because I had expected analytics to solve this problem, but analytics don't really solve this problem of CRM-ing your customers to a sense.

Daniel Stillman:

Do you remember the conversation the two of you had about where the gap was and the seed for this next idea?

Jane Portman:

Well, I wrote emails. I wrote emails to Benedikt and to Claire. I thought we will have all the bases covered. Claire was a marketer, Benedikt's an engineer, I can do design and the rest, and we were a killer team. And I can't believe they both said yes, so that was the process.

Daniel Stillman:

So at that moment, how did you decide to go all in? All three of you said, "Yeah, we're going to make this happen." How did you decide to structure your relationship at that beginning stage of this new idea?

Benedikt Deicke:

If I remember correctly, Jane had that proposal and connected all three of us, and I think the first thing we did was have a conversation about what we want from this. And we did an exercise about... I don't remember the name of it, but it was something from Google Ventures about company culture and tone of voice and stuff like that just to get a feeling of we're aligned in terms of values and goals. And that was pretty helpful to get a rough understanding of each of our expectations and where we might differ. And I remember that one of the exercises was, let's plan for, "Where do you see yourself in the next five years, 10 years, 15 years?" And I think one of the learnings from that was that we were pretty well aligned in terms of expectations and goals. And that made it easier in terms of starting just together, because we knew we were on the same path and not heading in different directions with the expectations and where we wanted to take this.

Jane Portman:

Because all three of us had experience consulting other for other SaaS companies, and we've seen different flavors of those SaaS companies, and it could be that, for example, me and Benedikt could go and expect a more calm, bootstrap business, and Claire would see, "Oh, let's raise five million in the next year," and just put fuel there. And we were more or less aligned with the sustainable bootstrap journey where we could take our time to build a sustainable product without burning a lot of money right away. So for example, one of those things.

Daniel Stillman:

Yeah. Yeah. So who facilitated that conversation or who brought the plan for that dialogue? Was that you Jane or was that Claire or?

Jane Portman:

I had an original three pager doc, and then Claire started piling on more questions, and then Claire brought this format for the workshop that we did together, so it was a collaborative effort. There were other resources we used, for example, for the concept of vesting, for the concept of not splitting the shares absolutely equally. We had this point system that we bought somewhere, where you first have equal amount of points and then you score a couple of points to the person who starts, a couple of points to the person who has the audience, a couple of points to the person who can do this and that, and we ended up with a slightly different number so that it's not a 50:50 split, which sounds to many founders, it's an obvious choice, "Yeah, let's do 50:50," but maybe it's not the best choice. Who knows? Well, we do.

Daniel Stillman:

How long did you spend on this conversation? You had your three-page doc, Claire brought in some of these visioning conversations from Google and the points conversation, how much time did you put aside just to facilitate that dialogue?

Jane Portman:

A few weeks. And we also put together a co-founder agreement. That was also part of this dialogue, that we fleshed out a few more details about specific scenarios that could go right or wrong. We even invited... What's the word for it, Benedikt?

Benedikt Deicke:

What was the name?

Jane Portman:

Third-party friend.

Benedikt Deicke:

A mediator basically.

Jane Portman:

And independent friend who could judge... Yes, mediator. A third-party friend who we all know who could help us resolve disputes if we could totally not do it on our own. Well, thankfully, we didn't do that.

Daniel Stillman:

Yeah. Well, just to be clear, this is a fourth-party friend, because there was three of you.

Jane Portman:

Yeah. Well, we all knew the person that we named the mediator. That was the idea, so that-

Daniel Stillman:

Oh, I see. So all three of you knew the mediator, and this was the person who was going to come in if you hit a bump, or were they-

Jane Portman:

It was the plan.

Daniel Stillman:

... also judging your partnership agreement as well?

Jane Portman:

Not much at all. Just for the bump role.

Daniel Stillman:

Yeah. Did you hit some bumps? Did this person have to come in?

Jane Portman:

Not for this person. No.

Daniel Stillman:

That's very interesting.

Benedikt Deicke:

It was basically a safety measure. I guess we were worried that when there's conflict, it would be two against one, and getting into unfair situations, and we wanted another neutral party that was able to put things into perspective and maybe have a neutral outside perspective and be like, "Yeah, you can't do this because it's unfair to that other person," and stuff like that. So we were lucky that we had a mutual, well, not close friend, but acquaintance that we all knew and trusted with this. And they were nice enough to agree. And in the end, luckily, it never came to it, but it was good to have it set up just in case.

Daniel Stillman:

It's so interesting. I feel like in a way almost having that... Or maybe I should ask this as a question instead of a presumption. Do you think having that backstop helped you manage your disagreements or did you just not hit any rough patches in the time that you were together?

Jane Portman:

I think all three of us were not naive, rather mature. Not 19 years old when you just jump in, build something and then figure it out. We're bitter and we've seen different situations in life. It's a lot similar to marriage. And even after you've seen a few couples divorce, you realize that nothing is really forever, and many scenarios may arise. So we wanted to put guard rails in place for potential different scenarios that could arise, that of course we might see eye to eye at the moment, but what if something comes along we don't know about, then what happens?

Daniel Stillman:

Yeah. Sorry, Benedikt. Was there something-

Benedikt Deicke:

No.

Daniel Stillman:

... you wanted to add about that? I just love the idea that you put the guardrails there, and if they're good enough, you don't even need them ideally.

Jane Portman:

Like a prenup.

Daniel Stillman:

Like a prenup, yeah.

Benedikt Deicke:

I guess one thing that was valuable in entire process of doing that, I think it was the Google design sprint exercise that we did. And having the founder agreement and just talking through all those things aligned expectations from the get-go. And I feel like that's already a good way to minimize disagreement down the road, because I feel like a lot of the fights that founders might have between each other is because they're not on the same page and have slightly different ideas about the future and slightly different expectations. And by just making sure that we're on the same page, for the most part at least, already helps with reducing the conflict.

Daniel Stillman:

Yes. Yeah. There's two things that I'm hearing here that are great principles for anybody. One is to spend significant time thinking about the near and longer-term vision, the 3, 5, 7, 15 year, and just align on, "Are we making a fast company or a slow company or something in the middle?" That's a really important decision to be straight on. And the other negotiation theory, there's this idea of interests, options and legitimacy. It's called the circle of value. It's, as we enter into this negotiation and we both have interests, we both feel like we have certain options and we both have our ideas of what legitimacy is. And I love that the three of you picked a person that you all agreed they would be, in a sense, an arbiter of what is legitimate and fair, so that it wouldn't be a two against one conversation. I think that's really amazing.

Jane Portman:

To be entirely honest, all these measures and being aligned and the vesting schedule and everything, this is all great. But the biggest success factor is that we had worked together prior to that. I would not jump into co-founder relationship these days without having worked with the person. And that's the only idea how you can judge their communication, their work ethics, and a lot of other things you can never understand if you don't get involved. We were lucky that, I had not worked with Claire for example, Claire had an amazing track record as a marketer, so I just took the dive. But the relationship that now keeps working is between me and Benedikt, and we had tested it prior to starting. So I consider that the key success factor. Everything else, surely great, allows you to part ways, but at the core of it is maybe bringing somebody for money first, or somehow before trying to bring them on into the shares or something like that.

Daniel Stillman:

Yeah. I mean, I think it's an interesting question of... And this may be a weird way to describe this, but Benedikt, you and Jane now are co-founders, right? So there is a difference in relationship between when you Jane brought Benedikt on as a contractor for hire on an idea that was yours. Now this is an idea that belongs to both of you.

Jane Portman:

I think the consultant relationship, it has different dynamics. And it's good because Benedikt could see that I'm adequate when it comes to money, I can see that Benedict is adequate when it comes to money. If we had only worked on a, let's say, non-for-profit project, it was just fun, might have been different. Who knows? But I just knew that it was fine. I don't know. It just felt fine. Felt secure and nice. And he didn't trick me into big money, even though he could definitely charge the hell out of me for what he did.

Benedikt Deicke:

And I guess what also plays into this is that we had very compatible styles of working. I feel like this is also something that is easily overlooked, is that the amount of planning you need and the amount of stuff you maybe do ad hoc and a spontaneous work stuff, if it that part doesn't align, one of the parties, or maybe both parties might get frustrated really quick. Because you might think, "Ah, this other person always needs two weeks of planning things out and then being able to execute. I want to execute right now." And the other person maybe is like, "Ah, he's always switching focus and making a mess and there's no structure." So I feel like a lot of it is also about matching styles of working on stuff.

Jane Portman:

I'm so glad you brought that up. It's not just the working style, not just the planning, but also the quality standards of what you put out. Because we are both rather fluid in planning, but we are super nitpicky that we need to put out the quality product. It's got to be close to perfect. Of course, it's not possible to achieve complete perfection in real life, but both in engineering and in design, we will strive for the best. And some people like it messy. I couldn't work with somebody like that, I'm pretty sure.

Daniel Stillman:

Fair. Yeah, there are the people who believe that you should put it out when it's at 80%, because of the Pareto principle, but you're like, "No, I want that last 20% before it gets out the door." That's good.

Jane Portman:

Email automation. We're sending bulk email to somebody else's customers. Seriously, 80%?

Daniel Stillman:

No. Well, and I'm glad that you have that shared perspective. Have there been challenges that you've had to manage in your relationship?

Jane Portman:

There have been disagreements.

Benedikt Deicke:

Yeah, it's not always a smooth ride.

Jane Portman:

One co-founder quit. Yeah.

Daniel Stillman:

Well, let's talk about it. I'm curious how you've managed some of the bumps in the road that you've experienced with each other.

Jane Portman:

Benedikt, what do you think? How do you describe that?

Benedikt Deicke:

I was wondering what to talk about. I mean, we should probably touch on Claire leaving the company at some point, because that's probably the most significant one so far, because it made a lasting difference and changes everything-

Jane Portman:

Changes everything.

Benedikt Deicke:

... and changes the dynamic, so.

Daniel Stillman:

Yeah. I mean, it's very interesting because you guys did a lot of upfront work to check on alignment, and then it... Between the start and... When did Claire decide to step down? What was that arc?

Benedikt Deicke:

I think it was one year in-

Jane Portman:

Just one year in.

Benedikt Deicke:

... something like that.

Daniel Stillman:

Just one year in.

Benedikt Deicke:

I mean, we talked about all that planning and the goals and the future and expectations, and what I probably have to say about this is, yeah, we made a plan, and yes, we had visions, but none of this was true. We expect it to be-

Daniel Stillman:

So I hope everyone listened to this point in the podcast.

Jane Portman:

No, the plan was true. We were true to ourselves. It's just, the plan didn't work as expected, as it often happens.

Benedikt Deicke:

I mean, we still had the shared vision and stuff like that, but everything took a lot longer than we expected. So I think one year in, we didn't even have the product done in a way that people were actually using it, so we were not making any money. And all three of us have been doing this on the side, we had still our consulting gigs where we were making the money to pay rent and food and stuff like that. And that of course took away from working on the product and everything was a lot slower. And yeah, about a year in, Claire was like, "Yeah, I have two other businesses I'm running and they are making money and they're taking most of my time and focus, and unfortunately I can't spend more time on userlist, because what's the point? It doesn't make any money, and I'm short on time anyway, so I'll focus my efforts on those other two businesses."

Benedikt Deicke:

And while it was a bummer for us losing our marketing expert, there wasn't a big argument about it because it made sense. In a way, we were in similar positions, just that each of us only had one other side business and not three. So it was sad, but in the end, I mean, because we had those guardrails in place, it was clear what needs to happen to have a transition out of the company. And the way we set it up in our agreement back then was we had to allocate the shares of the company roughly a third each, and we had the vesting schedule, so we'd only gain ownership of our shares over, I think, 50 months, something like that. So every month, we would-

Jane Portman:

Yeah, 50 months.

Daniel Stillman:

Five, zero.

Benedikt Deicke:

Five, zero, yeah. Almost five years, not quite.

Jane Portman:

And we just finished that with Benedikt, by the way, we're fully invested now. Just a few months.

Benedikt Deicke:

Yeah, we're fully vested [crosstalk 00:24:46].

Daniel Stillman:

Congratulations. How does it feel like to finally own your own company?

Jane Portman:

Not much different.

Benedikt Deicke:

It doesn't change much. But the goal was you'd earn 2% of that block of shares per month that you keep working on it. So when Claire was like, "Yeah, I don't have the time to put effort into this anymore," we first reduced her vesting rate from 2% to 1% for a while. And eventually we decided, okay, it doesn't make a lot of sense to keep her on this, and we stopped it at some point. And that overall reduced her amount of shares to whatever she had earned by that date and kept things fair in a way, because now we definitely own larger shares than her because she stopped working on it after a year or so.

Jane Portman:

Technically, going back in time, we should have just stopped vesting altogether. But this was this half measure that we reduced her vesting in half. And it felt nice to do because she was advising, but going back in time, and even if you're a young startup, every month of vesting counts. So if the person is not putting in work, don't vest them shares just because you want to look nice or hope for something, because the company will be worth much more down the road, and every percent becomes a sufficient thing. We don't regret this. It was just for a while, and we're happy that we're friends with Claire, but making difference between being nice and rewarding shares for work, these are different buckets, don't mix that. Don't mix that with friends or-

Daniel Stillman:

This is a very hard thing to do. Last night, I was-

Jane Portman:

Am I phrasing this right, Benedikt? You're just grinning.

Daniel Stillman:

Since you were all at that time working part-time, how did you define what was the right amount to be working on the project? Was it value created or was it hours logged?

Benedikt Deicke:

I think we had an informal agreement that it was 50% of our time sort of, but we didn't track hours or something like that. It was basically, we'd see each other's progress and be fine with it, or when you had the impression that, "Hey, you're not putting in enough work," then we'd call each other out on that. But overall, it was never an issue for the most part. I don't remember having a big conversation about that at any point, so.

Jane Portman:

Up to this point, we don't track hours, because why we're in is for freedom. But there's also pretty serious peer pressure and motivation and accountability that comes from having a co-founder. And if you're not putting in the hours, you're the one who feels guilt and suffers after all.

Daniel Stillman:

What advice would you give to someone else who feels like their co-founder isn't putting in as much as they should? It's a difficult conversation to have.

Benedikt Deicke:

But it's one you should have, right?

Jane Portman:

Even though it must be had. It must be had. This communication principle, I think I saw it in Crucial Conversations. I forgot the author of the book. It's pretty famous. Basically, you have problems with your boss, your spouse knows about it, your colleagues know about it, except for your boss. So if you feel like something is unfair, that is the conversation to have. And these fundamentals of being rewarded for your time, either with salary or with shares and keeping it fair for everybody, this is fundamental so that everybody can perform so that they feel everything is honest. Without that, without the feeling of fairness, without the fundamental of being fair, this is broken. You're feeling like you're trapped or something like that. This is not going to move forward. So it's fundamental.

Daniel Stillman:

Anything you wanted to add to that Benedikt?

Benedikt Deicke:

No, not much. I mean, it's an unpleasant conversation, but it's one you must have, because afterwards, things will feel better, because at least the opinions are on the table and you might fight about it, but maybe you agree. I mean, I remember we had some bumps like this a year or two ago, where I felt like Jane was a little bit distracted with other stuff, and we brought it up, and in the end, we agreed that yeah, maybe we have to restructure things a little bit. And in the end, it worked out and it was definitely better after having that conversation than the couple of weeks before it was like, "What's going on? We're not making enough progress on whatever task was on the to-do list back then." So might be uncomfortable at first-

Daniel Stillman:

Do you remember that conversation, Jane?

Jane Portman:

Hmm?

Daniel Stillman:

Do you remember that time?

Jane Portman:

Oh, sure. Yeah. It's not like everything is clouds, unicorns and roses and stuff. We just switched to full time maybe a year ago, it was a smooth transition. And we had some funding from Tiny Seed, which was good, but not enough to just hire full time, big time, but it already gave us some freedom. So there was this transition from, do everything yourself to get help and where and how and how this looks like. And at that point, I didn't have a clear picture of exactly how to efficiently delegate, let's say, the marketing department was the first we started like delegating out, and there was a series of experiments with hiring generalists, specialists. Not all the experiments were successful. And then there was this fundraising question because we did raise another angel round last year. So we were wondering, "Do you have good enough product market fit to support this fundraise? It doesn't make sense. How do we do this?" and other things, more discussions. But I'm happy we came out of the other side, happy and invigorated in a sense.

Daniel Stillman:

How often have you revisited that conversation you had at the very beginning that Claire helped co-facilitate, where you talked about your vision and your values?

Jane Portman:

Roughly speaking, once a year, we have a bigger planning goal. Maybe a couple times a year. Benedikt, what's your impression of that?

Benedikt Deicke:

Yeah. I feel like it probably wouldn't hurt if we just went back to that exercise from then and do the exact same thing again, because we haven't done that. But of course, at the beginning of every year or-

Jane Portman:

It's be fun to look at the responses. It would be fun to see the responses.

Benedikt Deicke:

Yeah. Right. Let's see how the vision maybe changes and the expectation changes. But overall, I mean, we're having conversations once per week about the short-term roadmap and what we are planning to do and things that are happening in the business and all of that. But I feel like, at least at the beginning of each year, we make a rough plan of like, what are the next big steps? Where do you want to go next and what needs to happen, and what are the problems? So in a way, we're doing it on a regular basis, but I guess it wouldn't hurt to have this deep workshop type of conversation where we try to realign on stuff. I think it wouldn't hurt doing it again.

Jane Portman:

Never hurts. I'd like to touch on how we do planning. And we borrowed this principle from Shape Up by Basecamp. And it says, basically, "Don't worry about your backlog as much as people do." So previously, before adopting this, we would religiously every month meet and reprioritize 60 items in our backlog. And this is just such a ridiculous activity, because in software, everything changes all the time, because you learn, you keep learning the circumstances, change, opportunities arise, things that seemed important, don't seem as important because you've learned something that is crucial to your customers in higher degree. And we just plan out the next, I don't know, let's say two, three big features. Even one, two, I would say. One, two, three, something like that.

Jane Portman:

That is true for product and for marketing, so we usually have a marketing theme direction for the next, let's say quarter or something. And there is also the things in the product that Benedikt is working on with the technical team. So there is high level roadmap, but there's definitely nothing set in stone, and we are fine with it. And that relates to that level of fluidity that we discussed. We're comfortable with that. There might be some people who are not, but works for us.

Daniel Stillman:

Say a little bit more about that. What's important about letting go of being strict about the backlog.

Benedikt Deicke:

I feel like-

Jane Portman:

The thing is, it will never be implemented in the order you put it. What's the sense of ordering 50 items?

Daniel Stillman:

Pair-wise.

Jane Portman:

You can barely make the first five happen in time, and given the fluidity of everything, product, customer, market, anything.

Daniel Stillman:

Yeah. That's fair. Benedikt, what was on your mind?

Benedikt Deicke:

Yeah, basically that. The backlog, they're all good ideas. You look at each one of them, you're like, "Yes, yes, that's a good idea. And we have this one customer asking about it and it makes sense for everyone else." But you only have so much time and you have to pick something and stick for it for a while to make meaningful progress on it. And by the time you're done with it, you can pick one other thing maybe, maybe two, if you're lucky, and you still have 50 other things on the list that are still good ideas, but not necessarily the best thing to work on right now. And therefore, just keeping that list and working through that list. I mean, we did that in the early days, and I remember going through that list every couple of weeks and being like, "Yeah, yeah, we should probably do that at some point, but we just don't have the resources right now. So let's move to the next thing and look at that. And yeah, same thing."

Benedikt Deicke:

And at some point, you just keep looking at the things and being reminded of all the nice things that you potentially could be doing, but you are not because you're working on other stuff or more important stuff. It just becomes in a way, becomes a little bit frustrating because you're always feeling like your product falls short and your product is way from done and way from useful, even though that might not even be the case, because a lot of people are already using it.

Jane Portman:

I there's anything we had learned after these four years of userlist, and we had been consulting prior to that, but I had never realized that it's such a tale of limited resources. It's all about limited opportunities that you can pursue, exactly like Benedikt said. And when you're a consultant, it seems like, "Oh, why don't they do that? That's on the surface. Why don't they do that? Why don't they do this?" And it's so easy to give advice, but when you're inside of it and you only have this much development resource and you have this much time, you have to A, prioritize, and B, somehow live in peace with this. So understanding that you can surely have the vision, but it's not always up to that vision because of resources. And I ask people who are way up in the letter and it's the same for them. It's the same for our big integration partners. It's never that you can make everything happen, so you have to live with it.

Daniel Stillman:

So how do two people choose one thing to focus on as the whole company? What is that conversation like for the two of you? What's easy about that? What's challenging about making that choice? And what do you do instead of having that list of reminders of things you could do, what do you have instead?

Benedikt Deicke:

We still have a list, but it's not super detailed. It's more like gut feeling, broad ideas and not super fleshed out. And our planning process these days are usually... One thing I think we do really well is we have a lot of customer interactions, either in customer support or during demo calls with potential new customers, or just keeping in touch with our audience. And that usually informs the next steps pretty well, because the things you keep hearing over and over again are probably the things we want to tackle next. And that makes the conversation relatively easy. And so far, I feel most of the times, we're on the same page about stuff. We have the same gut feeling that should probably go into this direction and ensure maybe we fight about like, should we do this particular part of it first or that other part of it first? But it's so far working out relatively well. I don't think we had big disagreements on product direction so far.

Jane Portman:

And moreover, there's the marketing department, my kingdom, sort of speaking, and there is the product department, which as a UX designer, I have a word to say, but it's Benedikt's ultimate hand touching the code. And if he doesn't write it, it's not going to happen, so he's the product owner for sure, and I'm totally at peace with that. I'm happy. Basically, we do call the shots to some extent in each of the departments. However, we do consult before pursuing some major directions. That's the key, but on daily basis, it's us ruling two different departments in fact. The marketing machine for this is insane. We did not pick an easy battle. It's always a lot of education and everything we have to do. Education, brand building, everything for such an essential tool, it's very important.

Daniel Stillman:

Yeah. Because not everybody has the mental model of why they need it.

Jane Portman:

And how they should use it once they install it. It's like everybody has an understanding they need email automation, but using it well to the full power, nobody's born an email automator, and we're trying to make up for that.

Daniel Stillman:

That is true. It is not a native capacity for anybody.

Jane Portman:

You can be born a designer, you can be born an engineer, you're hardly ever an email automator really. Let's face it.

Daniel Stillman:

So listen, the two of you, we only have a little bit of more time left and it's been a lovely conversation. Is there anything we have not talked about that we should talk about when it comes to sketching the arc of your co-founder conversation together?

Jane Portman:

There is a great deal of infrastructure that surrounds a software business that it's not talked about much, but it includes co-founder agreements, the legal paperwork, the bank account, postal addresses, cell phone numbers, having all the passwords in place, I don't know, support desk, shared emails. There's so much to do that should be done properly so that if anything happens, first, you pass the bus test, or if somebody decides to leave or I don't know, gives birth to a baby or something-

Daniel Stillman:

The what test? The bus test? I missed that.

Jane Portman:

Yeah. The bus test is like, can your business still survive when one of the founders gets hit by bus? And it's especially true for a solo founder business. I'm not kidding.

Daniel Stillman:

Wow.

Jane Portman:

What are you going to do? And it can happen.

Daniel Stillman:

Okay. And Benedict, what haven't we talked about that's on your mind? I've learned about the bus test. This is a new one.

Benedikt Deicke:

Yeah. I mean, this is a good point. What else? I mean, one thing that we hinted at earlier is the plan and reality don't always overlap. And I think looking back at the last four years, or almost five years, four and a half, something like that, things move a lot slower than you want them to and that you expect. And what I definitely underestimated is the toll that puts on you on a mental level, just the ongoing slog of putting in hours and hours and hours of work and the company just growing slowly, super slowly. And that was hard over the last year or so. It was hard for a while. I feel like there's this valley of despair where the product is used, but it's not making enough money to fully sustain the business, but it's not bad enough to easily call it off as a failure when it's in the state of barely working.

Jane Portman:

Definitely not bad.

Benedikt Deicke:

When it's barely working, it's insane. The stress that puts on you is crazy, and I underestimated that for sure.

Jane Portman:

The startups survive by not dying.

Benedikt Deicke:

Sort of, yeah.

Jane Portman:

You just need to keep going, and it's a slog. It's much more routine and boring than it seems. It seems like, "Yeah, exciting idea. Snap, we're going to make it happen," but-

Daniel Stillman:

Yeah. How do the two of you take care of yourselves given that stress and that slog? What do you do for yourselves to keep sane?

Jane Portman:

Human maintenance stuff; sleep well, eat well, exercise as much as you can. It's the simplest and the hardest thing to do.

Benedikt Deicke:

I mean, I think what we do well, maybe better than others, I don't know, we're very strict about boundaries. For example, we usually don't work on weekends unless a thing is on fire. The weekends are off, evenings are off. We don't have expectations to be on call 24/7 for whatever comes up. And I think that helps in keeping your mental side in check by just having breaks and taking vacation and taking time off and being fine with that, and not expecting the other person to be there and answering emails and answering messages all the time. I think that helps with keeping us sane.

Jane Portman:

There's another angle we do fairly well compared to people I know, is hanging out with other founders, peer support. And all of us have our own mastermind groups when we hang out with other founders just to talk life and to talk business every two weeks let's say or something. And we have great advisors and we have over 20 angel investors who, if we have hit a wall, I just write up a giant notion doc describing the problem and we send it to a couple of most relevant people and we try to brainstorm that. So it's never like we're in a box or alone, there's always some sort of input from peers or mentors.

Daniel Stillman:

One thing I'm taking away from this conversation is you met inside a community, and it seems like community is also helping you stay afloat and stay sane.

Jane Portman:

It's not always the same community, but yeah, it's different levels of community. Many levels of it has evolved. Definitely. But you can't just go alone.

Benedikt Deicke:

Yeah. I mean, if you want to take away one thing from all of this, I guess just building a network is the best thing you can do, in whatever we talked about, either finding a co-founder, finding advisors, finding investors, employees-

Jane Portman:

Employees too.

Benedikt Deicke:

... just get out there and make friends with people, and that will come a long way. It will take a while to build that network and to nurture those relationships, but in the end, a lot of the good things that happen to userlist, we can probably.... Yeah, no, I'm not finding the right word, but at the root, if you follow it back long enough, you find this was based on this one relationship that we had in our network or whatever, that friend and that recommendation or whatever. So I feel like that's one of the key skills to develop, is making friends.

Daniel Stillman:

Yeah. I think it's really beautiful. I mean, I can't imagine that either of you thought when you first logged on to that community, that this is what it would've led to.

Benedikt Deicke:

Definitely not.

Jane Portman:

Yeah.

Daniel Stillman:

Well, I think that's a really great place to close out. I'm really grateful for the time, for the both of you being so reflective and open and honest about your experiences and your insights. I really appreciate it.

Jane Portman:

This was fun to share, going down the memory lane.

Daniel Stillman:

Yeah. There's a lot to be gathered from memory lane. It's awesome.

Benedikt Deicke:

Yeah. We enjoyed that conversation.

Jane Portman:

Thanks so much for having us.

Daniel Stillman:

All right. We'll call scene. Yeah. Well, I really appreciate it guys. Thank you so much.

Jane Portman:

Thanks for having us, Daniel.

Wired to Create Together

Today I host a conversation with Carolyn Gregoire and Scott Barry Kaufman, the co-authors of the 2015 bestseller, Wired to Create. Their working title was “Messy Minds” and one of the core ideas of the book is just that - deeply creative folks can manage messiness, plow through paradox and move calmly through contradiction. 

These capacities are also powerful tools for managing a creative relationship.

I’m doing a series of interviews with co-founders on how they design their conversations (ie, their broader relationship) and manage themselves and each other while building and running a company. 

A book is a mini-company, and so when I met Carolyn through a friend, I thought she and Scott would be amazing folks to unpack how a high tolerance for dissonance, complexity, ambiguity, and chaos can help us make amazing things, together.

Creativity, making something new, isn’t ever a clear linear progression towards the dream, the magical ideal goal. There’s always iteration, recursion, re-invention…and being patient with the process, your creative partner and yourself - that last one is a truly powerful key.

One of my favorite insights was the idea of the importance of sensitivity and awareness of your own inner state and the willingness to take downtime…both to manage yourself, refuel and to trust that stepping back will always help - since constant production isn’t possible!

One thing you’ll hear over and over again is the complementarity and flow in a positive creative relationship: being able to feed back and forth between each other and also give and take, grounded in respect and admiration for each other's skills and contributions. This respect for the other’s skills allows for a dramatic increase in output through parallel work, or relay-race style collaboration.

Make sure to check out Carolyn’s other writing and book doula work at carolyngregoire.com and Scott’s podcast, course, and his recent best-selling book, Transcend, at scottbarrykaufman.com.

Links, Quotes, Notes, and Resources

Carolyn Gregoire's website

Scott Barry Kaufman's website

Wired to Create, by Scott Barry Kaufman and Carolyn Gregoire

Trust the Process, by Shaun McNiff

The Messy Middle, by Scott Belsky

Origami: From Angelfish to Zen

Minute 8

Carolyn Gregoire:

I always think of creativity in terms of birth metaphors, which is a little bit cheesy, but I think they're very apt. I do think you go into a project with these just big dreams and expectations and all of the hopes of what it can be. That's important because I think it gives you the fuel, but then you do confront the challenges and the reality, and I loved working on the book. And of course, though I had my moments where I was like, "Can I really do this? I've never written a book before. I'm going to fail," all of this self-doubt, the moments of stress.

But then, if you can keep the seed of the magical thinking alive, which is I think part of what we're tasked with doing as creative people, it does carry you through to the end. And then, yes, I did have like a postpartum dip afterwards. It's like, you put something out into the world that's been with you for what I think our process was nine months actually, and there's a little bit of a sense of emptiness and you want to fill it up. At least I experienced wanting to fill that immediately with something else, but it's good to sit in that open space after you put something out into the world and just give yourself some breathing room and then let the next thing come in and emerge as opposed to what I sometimes tend to do, which is just reach for something else. So I totally agree with both of those things.

Minute 11

Carolyn Gregoire:

But I think having a collaborator in whatever form really helps you to sustain the commitment and keep the energy flowing. It's not that it can't be done, but it's just not as fun and it's harder to sustain the motivation, I have found, in my own projects, and then helping other people with books, which is part of the work I do now. It's so key to have someone else there in some capacity.

Minute 20:

Carolyn Gregoire:

The creative process, I think, comes from that, the tension and the unknown. There's actually two great books that speak to the point that Scott just made. One is actually called Trust The Process. That's by an art therapist and it's incredible. He really talks about how those moments of attention that we see as an obstacle or something going wrong or getting in the way are actually what push us to be forced to break through it. That's kind of what the breakthrough always comes from, and I think that's absolutely true. And then there's another book called The Messy Middle, which really talks about the stage of the process where things really get convoluted and you just don't want to continue and it all kind of like... You're not feeling good about the project anymore and obstacles arise, et cetera.

Minute 24

Carolyn Gregoire:

That's a great question. I don't know if this is a map that may be a key that would unlock a part of the map, which is something that I've only learned more recently after going through so many creative processes and it helps me now that I understand it for myself, but that when you're stuck with something or something's not working, or there's real doubt or frustration, there's valuable information in that. It's not just like a personal... Usually, at least for me, it's not just my own self-doubt of I'm going to fail or whatever. It's like there's actually something missing here or there's something wrong and I'm feeling that, and if I push into it and if I really investigate, instead of turning away from it, I realize there's something that that's telling me.

Minute 34

Scott Barry Kaufman:

I get the sense that for a lot of creative people, the reward is inherent in the process and it's not so focused on the goal and focused on producing the work and making sure the product gets out there. You have a lot of creative people that enjoy the process so much that it's like, "Oh, now it's out there. Yeah. I forgot." I mean, I'm kind of that way. Once the book's out there, I want to move onto something else.

Minute 35

Scott Barry Kaufman:

to me, creativity mirrors the self-actualization process more generally. It's a never ending process. One goes their whole life continually growing and learning and finding meaning. And to me that's what's enjoyable. That's what's enjoyable about life. It's the continuous nature of the change in the learning and the creating. It's not the doing, at least for me, and I can say a lot of creative people.

Minute 38

Daniel Stillman:

What do you feel like is your brightest key to trusting the process?

Scott Barry Kaufman:

Oh, well, it's also trusting yourself. It's trusting your own capacity to fail and get up again, and being able to be comfortable in the space of trial and error. A lot of people's being is not very comfortable with trial and error. The second they have an error, they're done. They're not trialing again. I mean, look, I got an interesting taste from this. I tried out stand-up comedy recently. It's been a long-term dream of mine, and it's interesting. Some jokes fall flat, and you're like, "Okay, we've got to bring that one to the laboratory and tweak some words and then try it again. See if it gets a laugh." That trial and error process to me is fun. It's something I trust myself that I can learn from my mistakes. I think that's a big key, is that you trust that you can learn from mistakes so you're not so scared of mistakes.

Daniel Stillman:

When I was a younger man, I was much older in the sense, in the Bob Dylan sense. I really wanted to not make mistakes. I thought the only way you learned was by doing things right, and it's a heavy burden to carry. Ironically, I mean, we all know this, that no experiment ever fails. Experiments are information, but there is a lot of fear that comes from looking bad, from falling flat, of our own expectations or expectations that we think others have of us.

More About Carolyn and Scott

About Carolyn

Hi! I’m Carolyn. I am a Brooklyn-based writer exploring the realms of psychology, spirituality and creativity. I’m the co-author of Wired to Create: Unravelling the Mysteries of the Creative Mind (Penguin) and creator of the Webby Award-winning CREATIVE TYPES personality test, which has been taken by over 7 million people worldwide.

My writing has appeared in publications like Scientific American, TIME, Harvard Business Review, The New Republic, Quartz, Yoga Journal, Tricycle: The Buddhist Review and The Huffington Post, where I worked for five years as a Senior Writer. I have written or contributed to nine books on creativity, health and human potential, including Arianna Huffington’s New York Times bestsellers, Thrive and The Sleep Revolution, and the foreword to a new translation of the classic philosophical work, Meditations by Marcus Aurelius.

About Scott

Scott Barry Kaufman is a cognitive scientist and humanistic psychologist exploring the mind, creativity, and the depths of human potential. He is a professor at Columbia University and founder and director of the Center for Human Potential. Dr. Kaufman has taught at Columbia University, Yale, NYU, the University of Pennsylvania, and elsewhere. Dr. Kaufman received a B.S. in psychology and human computer interaction from Carnegie Mellon, an M. Phil in experimental psychology from the University of Cambridge under a Gates Cambridge Scholarship, and a Ph.D. in cognitive psychology from Yale University. He is also an Honorary Principal Fellow at the University of Melbourne’s Centre for Wellbeing Science.

Dr. Kaufman hosts the #1 psychology podcast in the world The Psychology Podcastwhich has received over 20 million downloads and was included in Business Insider’s list of “9 podcasts that will change how you think about human behavior.” Dr. Kaufman is interested in using his research to help all kinds of minds live a creative, fulfilling, and self-actualized life. His early educational experiences made him realize the deep reservoir of untapped potential of students, including bright and creative children who have been diagnosed with a learning disability. In 2015, he was named one of “50 groundbreaking scientists who are changing the way we see the world” by Business Insider.

Full Transcript

Daniel Stillman:

You all are officially welcomed to The Conversation Factory. Scott, Carolyn, welcome aboard. Thanks for being here.

Carolyn Gregoire:

Thanks for having us. Good to be here. Good to talk to you again.

Daniel Stillman:

Yeah, thanks. So, I want to start... I mean, when's the beginning of any story? But I want to start with how you two found each other. The serendipity that maybe brought you together, and, yeah, let's just start there. How did you two find each other in this crazy mixed-up world?

Scott Barry Kaufman:

You bring us way back. I need to, in my head now, have to go back to when I was another person. I feel like we grew up since then, if that makes sense. That person back then feels like a kid in my head and now I feel like an adult to some degree. But, yeah, do you remember the exact origin story? Because I remember sitting down with you at Huffington Post and you're interviewing me for an article about creativity and I loved your work, of course, and I was excited to be interviewed by you. I remember us just having a conversation about creativity, but do you remember how that interview came about?

Carolyn Gregoire:

Yeah, it actually went back a little earlier than that. So I was writing about psychology and personality psychology for The Huffington Post. I was a reporter there for six years, and I have this just personal obsession and fascination with daydreaming. And just because I've always been spacey, but also always dreaming up new ideas and things in my head, it's been something that's been an obstacle in my life and that I've been criticized for, but secretly I felt it was actually really important to me and that good things were coming out of it. And so, anyway, I was thinking that I wanted to write a piece about daydreaming and I found that Scott had done some research and written a paper about the positive qualities of daydreaming and about this trait called positive constructive daydreaming as differentiated from rumination or distraction.

Carolyn Gregoire:

It was just so incredible finding that paper because I finally could see that there was research saying that actually daydreaming is so important for creativity, for empathy, for self-understanding, all of these different positive traits, and I was just beyond thrilled to find it. And so I reached out to Scott and I wrote a piece about his paper on daydreaming and then we collaborated again. I wanted to do a piece about the personalities of creative people, which is something that I was just also fascinated by, and immediately thought of Scott since he had done research on creativity.

Scott Barry Kaufman:

Yeah. I remember you asked me, "What do you think creative people are like?" And I said, "They have really messy minds." I really never know what's going to come out of my mouth, just in general in life, and that was one of those moments where then I heard myself say that and I was like, "Yeah, I like that. Messy minds." And then I just feel like that was just a great encapsulation of creative people that you really resonate with, Carolyn.

Carolyn Gregoire:

Yeah. I think that phrase stayed at the center of our collaboration and all the work we did together. The article that I wrote about creative people went really viral, got five million views or something, much to my surprise, and became the basis of the book that we wrote together. And really at the heart of all of it was this idea of messy minds and paradox and contradiction. That's something we'll probably get into more later in this conversation. But I think that was the reason for the virality, was just people were like, "Yes, this is me," and it's something that there is some literature around, but that is not really talked about a lot. So that idea I think took hold in that moment and took us pretty far together in our collaboration.

Scott Barry Kaufman:

I miss your Huffington Post articles. I would look forward to them every week. You're my favorite science writer, and, yeah, that was just a nice period. That was a nice time period where stars aligned, where I was a really nerdy scientist, I thought you were an excellent science writer, and it was just so much fun to team up with you. Yeah.

Daniel Stillman:

I love the phrase of stars aligning and...

Scott Barry Kaufman:

It felt that way. Yeah.

Carolyn Gregoire:

Yeah. Very, very kismet. It just kind of happened.

Scott Barry Kaufman:

Yeah. Organically.

Daniel Stillman:

It's always interesting to zoom into the moment inside the moment and that feeling of pull, instead of push from the universe, because we all know that feeling of pushing to try and make something happen. And this sounds like pull from the universe where it was like this yes moment. Well, of course, we're going to do this thing.

Carolyn Gregoire:

Yeah. I [inaudible 00:05:06]-

Daniel Stillman:

Do you remember that feeling?

Carolyn Gregoire:

Yeah, this is something I think about and talk about a lot because I always say that the things that come to me are always so much better than the things that I chase after and reach out for and strive for myself. Every job I've had, it's happened its way into my lap, and this project, which is one of the most fun things that I've gotten to do, which has led to other wonderful things, sort of just came to me. I think that when you have that sweet spot of something drops in and then you really run with it and the passion is there, it's always the best. Those are the wonderful opportunities in life.

Scott Barry Kaufman:

Absolutely.

Daniel Stillman:

One of the things I was listening to, a talk you'd both had given at Google. This is a million years ago, and you do look like babies, by the way, Scott. It's amazing.

Scott Barry Kaufman:

I mean, I looked at that video and we... At least I look much younger. Yeah.

Daniel Stillman:

Yeah. I mean, this is going back. This is 2015 y'all wrote the book, so I think this was just maybe a year after that.

Scott Barry Kaufman:

I think Carolyn looks the same.

Carolyn Gregoire:

Yeah, maybe.

Daniel Stillman:

Whatever your moisturizing routine is, stick with it. Good job. So, here's the thing. I think you talked about... I'm going to mispronounce this. It's the positive aspects of... There's negative aspects of schizophrenia and there's these elements in a creative person. I think the term was magical thinking, like the positive aspects of magical thinking. I feel like at the beginning of any project there is some magical thinking. You're like, "This is going to be great. We don't think of the bad sides at all. This is just going to be amazing." And I feel also in every collaboration there's always a dip after that peak, and I'm curious if you experienced that dip and/or the magical thinking flow. I can see Scott's thinking to the side.

Scott Barry Kaufman:

I mean, I've had the blessing to have had two major collaborations with a coauthor. Just wrapped up a new book with a coauthor, Jordyn Feingold, and of course my collaboration with Carolyn, and they were both so magical on my end. I'll be curious to get Carolyn's perspective. I'm just going to start with my perspective. They both... I've been so blessed. They were so magical in that there was flow from start to end, and it almost seems like an incredible, crazy thing to say, but it somehow happened.

Scott Barry Kaufman:

I guess you've picked the right people with the right energy. It just flows from start to end. I felt that way with Carolyn. I felt that way very much as well, equally, with Jordyn with this new book I did. There is a certain kind of complimentary aspect with both of those two coauthors where they're really good at feeding off... Like a there's a give-and-take. I can do something and they can take that and just make magic out of that, and then I take that and refine it, and then we move onto the next thing. That's how it felt to me.

Carolyn Gregoire:

Yeah, I agree with that. And I agree that there was a lot of flow in this project, and I especially appreciate that having gone through other projects, smaller ones, where there's less flow, you really learn to appreciate it in those moments. But to the point about the magical thinking and the dip, I always think of creativity in terms of birth metaphors, which is a little bit cheesy, but I think they're very apt. I do think you go into a project with these just big dreams and expectations and all of the hopes of what it can be. That's important because I think it gives you the fuel, but then you do confront the challenges and the reality, and I loved working on the book. And of course, though I had my moments where I was like, "Can I really do this? I've never written a book before. I'm going to fail," all of this self-doubt, the moments of stress.

Carolyn Gregoire:

But then, if you can keep the seed of the magical thinking alive, which is I think part of what we're tasked with doing as creative people, it does carry you through to the end. And then, yes, I did have like a postpartum dip afterwards. It's like, you put something out into the world that's been with you for what I think our process was nine months actually, and there's a little bit of a sense of emptiness and you want to fill it up. At least I experienced wanting to fill that immediately with something else, but it's good to sit in that open space after you put something out into the world and just give yourself some breathing room and then let the next thing come in and emerge as opposed to what I sometimes tend to do, which is just reach for something else. So I totally agree with both of those things.

Daniel Stillman:

It's so interesting because the idea of magical thinking as a seed to be nourished is a really unexpected way to think of it, right? And I think that's really beautiful. Scott, I was listening to one of your TEDx talks around the four Cs of human intelligence, like capacity, competence, commitment and creativity.

Scott Barry Kaufman:

I'm glad someone watch that talk.

Daniel Stillman:

I think that there's some numbers there. I don't think I'm the only person.

Scott Barry Kaufman:

Thank you.

Daniel Stillman:

But I think there's this idea of commitment, right? Seeing something through. But it sounds like it really kept its own energy, which is amazing.

Carolyn Gregoire:

Yeah. I think that's part of the collaboration, or the magic of the collaboration. Writing, it truly is such a lonely endeavor when you're writing a book on your own. I personally believe that, I think it can be lonelier actually than other forms of solo creative practice, because you're basically talking to yourself. Writing is about communicating and when you don't have someone that you're working with, you're just in your own head, literally, talking to yourself for months on end.

Carolyn Gregoire:

And eventually you're talking to somebody else when the book gets out into the world and you can have conversations about it. But I think having a collaborator in whatever form really helps you to sustain the commitment and keep the energy flowing. It's not that it can't be done, but it's just not as fun and it's harder to sustain the motivation, I have found, in my own projects, and then helping other people with books, which is part of the work I do now. It's so key to have someone else there in some capacity.

Daniel Stillman:

Yeah. So one of the things... Is there more you wanted to elaborate on with that, Scott?

Scott Barry Kaufman:

I said, for show.

Daniel Stillman:

That's all good. So I was looking at some of the aspects of what a creative person is in this messy minds concept, the high tolerance for dissonance, complexity, ambiguity and chaos seemed to me to be the perfect skills to work through what you were talking about, the complementary, the give-and-take, and the flow. I'm curious with what give-and-take looks like keeping ambiguity and complexity and chaos as values in a collaboration.

Scott Barry Kaufman:

Well, I think that this book didn't have a fully-formed... I got the sense they were going kind of chapter by chapter and things kept emerging. I don't think we had the whole thing planned out in our head. Like we would maybe chapter outlines, but we were very open to it going in all sorts of different directions and... Well, this is my recollection.

Carolyn Gregoire:

Yeah, absolutely. And I think what, again, emerged was the play of opposites that became such a central theme in the book. And then I think to your question how that plays out in the collaboration is I think having someone who's more of a writer and someone who is more of a researcher was really helpful to just get into that dance of the idea and then its expression, and to play around with that. Like Scott would bring in really the research and the evidence, and then we would be like, "Okay, how can we play with that, and where does that take us?" And there was always a give-and-take and a dance within that.

Scott Barry Kaufman:

Totally. And I also wasn't always quite sure how Carolyn was going to masterfully integrate a big dump of science. I would give her like a Dropbox dump of like a hundred articles and I never knew exactly how, in a draft of a chapter, she was going to integrate these things. And so she surprised me with like... I mean, new things emerged. I was like, "Huh, I hadn't really see... Connected those dots," and yet she'd connect those dots. So don't count yourself out as a good researcher too there, Carolyn.

Carolyn Gregoire:

[inaudible 00:14:55] I've definitely learned to research, but I think having... It was just a good balance having the science from Scott and then more of the editorial direction on my end.

Scott Barry Kaufman:

Yeah.

Daniel Stillman:

Scott, I'm curious in your recent collaborative projects, there are some people who say that having clear roles and responsibilities, a division of labor or respect and admiration for, as it seems like you two were talking about, the different skills in the collective. Have you found that to be the case? And I mean, I suppose this is a question for both of you and the other collaborations that you've had since then. It seems like the messiness can become stepping on somebody's toes, or it can be, as you say, a dance.

Scott Barry Kaufman:

Well, yeah, for sure. And I think that the benefit is in the Venn diagram. There really wasn't that much overlap of... It's not like Carolyn had this big aspiration to be an amazing research psychologist. I didn't feel there was much stepping on toes. I had and continue to have great admiration for her skill set, and I hope she still has appreciation for my skill set. But that just wasn't too prominent. I could see how it could have been different. I could think in my head about... Some people are coming in my head right now where I was like, "I don't think I'd want to write a book with them," because I feel maybe they would constantly want to kind of battle for minute credit of certain aspects of it, where it's like, we weren't too concerned with that because we did all the book tours together and stuff like that. We're proud of the whole product together.

Carolyn Gregoire:

Yeah. And I think also, maybe breaking it up into phases. I agree that separate roles is valuable and I've been reflecting on that recently. I think with the ideation of the book, which we didn't know at the beginning exactly where we were going, we spent a lot of time hashing it out together, brainstorming, really breaking things down and looking at them from different angles, and then divided the roles. And I think that was helpful. I feel that in most successful collaborations, I think there's a part that you are doing together and then there's a part that's very individual.

Carolyn Gregoire:

I think if we were kind of in drafts writing together, I don't... Maybe people work that way, I don't know, but that feels to me like a very bad idea. I can't really imagine writing a book with someone that way. So having like, "Okay, here's the part where it's Scott," and then he's turning it over to me, and then I'm handing it back to him, and there is a bit of a division of labor, I think it was valuable.

Scott Barry Kaufman:

It's a good point. Yeah.

Daniel Stillman:

One of the things you said, Carolyn, in the conversation that you and I had a while back now, and Scott, you were speaking to this just now, is the evolution and the definition and the clarity of the project happening in an emergent fashion. And I think you had said, Carolyn, that the title of the book and what the book was really about, in a sense, came towards the end or the middle of the end.

Scott Barry Kaufman:

That wasn't our working title.

Carolyn Gregoire:

Yeah. It did come towards the end. I think our working title actually was Messy Minds, and then our publisher thought that it was too negative or that people would be put off by it. So it became Wired To Create, but, yeah, there was definitely an emergence of... Even though we were working with this theme from the beginning about creativity being messy and paradoxical, I don't think it really came through until the end, both how central that actually was, that that was really what all of that was about was these oppositions. And then also the idea that creativity is something completely innate and hardwired, and there are these different sort of ways that we can tap into it a bit more, but it's naturally there. So that was emergent. Absolutely. Yeah.

Scott Barry Kaufman:

Yeah. Agree.

Daniel Stillman:

It's funny. I put a quiz to a group recently, what's more important, the beginning of a story or the ending of a story? And it was really interesting to watch the results on the poll come out pretty much as a dead heat. And I think in a way, when we tell the story of creativity, I know Scott you've talked about our self narrative as a component of psychology, and in a way we're telling the story of creativity while we're doing it. There's something really beautiful about the idea that the story changes by the end, as we're telling it to ourselves.

Scott Barry Kaufman:

Yeah, [inaudible 00:19:59]-

Carolyn Gregoire:

Yeah, I think... Go ahead.

Scott Barry Kaufman:

I mean, there's so many processes that are part of... The whole creative process involves lots of different stages and some of those stages are stages we don't even tend to include as part of the creative process, like the revision stage, [inaudible 00:20:22], or the deliberative stage, like, "Oh, that's not creativity," and we include that as part of the whole process. And so some of these processes or stages can seem incompatible with each other and you have to trust the process is the point. You have to trust that at the end, that it was like... In the middle, but that the end, something great emerges and you got to trust that.

Daniel Stillman:

Carolyn what’s on your mind?

Carolyn Gregoire:

The creative process, I think, comes from that, the tension and the unknown. There's actually two great books that speak to the point that Scott just made. One is actually called Trust The Process. That's by an art therapist and it's incredible. He really talks about how those moments of attention that we see as an obstacle or something going wrong or getting in the way are actually what push us to be forced to break through it. That's kind of what the breakthrough always comes from, and I think that's absolutely true. And then there's another book called The Messy Middle, which really talks about the stage of the process where things really get convoluted and you just don't want to continue and it all kind of like... You're not feeling good about the project anymore and obstacles arise, et cetera.

Carolyn Gregoire:

But the point is, if you don't encounter those things, then you don't reach these new places and these new directions, and I think there's a big difference between production and creation. That's something that I reflect on a lot. I think production is when you know exactly where you're going from the beginning and you just execute and you follow through with that, and creation is something different. It's something that involves struggles that take you on detours, which ultimately contribute to the end product that you come out with, and that's always somewhere that you couldn't have exactly imagined from the beginning.

Scott Barry Kaufman:

Very much agreed with that.

Daniel Stillman:

So from the sense of-

Scott Barry Kaufman:

I didn't know about those two books.

Daniel Stillman:

Neither did I. I'm looking forward to The Messy Middle, and we all know it. It's a good name. When I think about trusting the process, in order to trust the process, we have to know the process, and I feel like many people don't have a strong mental model — no pun intended — of what the creative process is. And I just so happen to have two experts on the call with me. And so I'm wondering, from your perspective, Carolyn, you laid out two fundamental poles, I guess, of a paradox, producing and creation, and that production and creation are not the same and that those are things that we might even iterate through. If you were giving advice to someone at the outset of a creative endeavor, what map would you hand them?

Scott Barry Kaufman:

Wow.

Carolyn Gregoire:

That's a great question. I don't know if this is a map that may be a key that would unlock a part of the map, which is something that I've only learned more recently after going through so many creative processes and it helps me now that I understand it for myself, but that when you're stuck with something or something's not working, or there's real doubt or frustration, there's valuable information in that. It's not just like a personal... Usually, at least for me, it's not just my own self-doubt of I'm going to fail or whatever. It's like there's actually something missing here or there's something wrong and I'm feeling that, and if I push into it and if I really investigate, instead of turning away from it, I realize there's something that that's telling me.

Carolyn Gregoire:

It's like this little devil on my shoulder that's like, "Something is wrong here." By realizing what's wrong or what's missing, something completely opens up. I guess that's what problem-solving is, in a way. There's a problem and you have to go deep into it and not run away in fear, and the going into the problem really opens something up. So, yeah, if that makes sense, that's really been one of the big keys for me, is like, okay, if I'm stuck with something, let's really get into the tension instead of resisting it and running away from it, or feeling like something is wrong, because it doesn't mean that something is wrong at all.

Daniel Stillman:

I think that's beautiful. Scott, when I asked the map question, what sparked for you?

Scott Barry Kaufman:

Well, a big theme in the book... This is amazing. You're bringing us back. It's like we're doing interviews again about Wired To Create. It's bringing back memories.

Daniel Stillman:

It's evergreen.

Scott Barry Kaufman:

But you know... What'd you say?

Daniel Stillman:

It's evergreen.

Scott Barry Kaufman:

It is evergreen. Absolutely. But you have to understand, we haven't done this together in like... It's five years, six years. But anyway, a big theme in the book really is the importance of downtime, and I think in one's model of creativity, they really have to allow themselves time away from the problem and build that into their model because too many people get too stuck in, one, they keep rummaging in one part of their brain network and they can't get out. And then they think, "The more I rummage in it, it'll come to me," as opposed to doing other activities and tangential act projects, like projects that you can make connections and projects which you can really actively force your associate network to go down a different path, and then you return to the problem. So I think that it's a very iterative process of going back and forth between the external world and your internal world. External world, internal world.

Carolyn Gregoire:

Yeah. I actually want to echo that that's really so critical and also observing my own patterns over many projects is that what I naturally tend to do is start something and get the ideas down, and then often step away from it for a while and then really do the writing and bring it through. I've seen that with other people, too. I've learned to actually leave a certain amount of time for projects or to turn down rush projects, because even if you could do it in a shorter period of time, it's like, there's just this certain amount of incubation space that's needed.

Carolyn Gregoire:

So I never do rush projects anymore, even if I could, pretty much, because I like having multiple things at the same time so that I can take some space and shift from one thing to another, instead of like, "Let me just do this really quickly and then stop and then go to something else." It just doesn't work well for me, and I think it doesn't work well for a lot of people.

Daniel Stillman:

Yeah. This is like the old saying, "You can't give nine women one month to make a baby."

Scott Barry Kaufman:

Oh, and where it was going with this.

Carolyn Gregoire:

I never heard that.

Daniel Stillman:

Yeah. It's like, "Well, I know it takes one woman nine months. Can't we just multitask this?" It's just not how that works. It takes nine months. It takes what it takes. And I just want to make sure I understand, Scott, and Carolyn, you were speaking to this too, downtime seems like it comes in several flavors. Like, as you were saying, Carolyn, way before. Like daydreaming can just be like phasing out. And Scott, I know you were saying before we started, you take an afternoon nap. That's just pure downtime? And then there can be taking a shower, which is like just letting your mind wander. And then what you're talking about, Scott, it seems like using your brain but on something that is parallel or tangential that can spark something? I want to make sure I understand that. It seems like there's several flavors of downtime-

Scott Barry Kaufman:

No, that-

Daniel Stillman:

... that we're talking about.

Scott Barry Kaufman:

... [inaudible 00:28:18] nuance. No, I definitely like that nuance. I think that some of the best kind of... Or getting away from the project at hand is, then you work on another project. For instance, if I'm trying to write an article and I want to synthesize lots of ideas, I'll go down one rabbit hole of ideas of an article and those ideas. Then I'll put that aside and I'll go down a completely different one and then I'll go down a completely different one. And then I'll return to the first one.

Scott Barry Kaufman:

Usually you get a full night's sleep as well. You trust your mind at night to do some unconscious synthesizing, which it does, and then you return to it the next day, you find, "Wow, I have ideas now." So it's interesting. So much of what we're seeing really keeps coming back to the idea of trust the process. It just keeps coming back to that. It is a whole process.

Daniel Stillman:

Yeah. But also knowing the process-

Scott Barry Kaufman:

You can't cudgeon it. Or, what's the word?

Daniel Stillman:

Yeah. Bludgeon or-

Scott Barry Kaufman:

Bludgeon.

Daniel Stillman:

... bludgeon I think is the word. There's a quote from... Have either of you read Kahlil Gibran's book, The Prophet? It's a very beautiful... My mom thought there was too many words in it. That was a funny response to this book of poetry. I know my mom will listen to this episode. It's not an insult. I promise, mom. I love that about her.

Scott Barry Kaufman:

Okay.

Daniel Stillman:

There's a phrase where he says... He's talking about love. He says, "Let there be spaces in your togetherness." And I always loved that idea of togetherness, but spaces in the togetherness. And it seems like definitely with a creative partnership, there needs to be time apart, time to work on your own pieces, and where also spaces in your togetherness when you're talking about working on the project where it's pure downtime and also wandering and discovering and trying some other things. It sounds like really having that incubation time is super important to let it just settle in. I will have to find this. There's a book that's quoted one of my... I'm an origami nerd. You talked about being a nerd, Scott. I was an origami nerd in junior high school.

Scott Barry Kaufman:

Wow, that's incredible.

Daniel Stillman:

It did not make me very popular. It was not a-

Scott Barry Kaufman:

I think that's really cool.

Daniel Stillman:

There's a book called Origami: From Angelfish to Zen. The whole first part of the book was about the math and the science behind origami. And there was a story he told that's from this book called The Psychology of Invention in the Mathematical Field. He told the story of these two twin sisters who were banging their heads against a math problem. And during the night, one of them was talking in her sleep and the other one woke up and heard her sister dreaming the solution-

Scott Barry Kaufman:

Oh, wow.

Daniel Stillman:

... to the problem. And what's amazing is that the sister who woke up in the night knew the solution that the sister's subconscious had solved it on some level. It's always been an interesting reminder to me that, yeah, as you say, Scott, sleep is important.

Scott Barry Kaufman:

Oh, definitely.

Daniel Stillman:

Like really, really important.

Scott Barry Kaufman:

Oh, definitely. Definitely. And the sleep process, to a lesser degree, when you're just doing things like meditating or taking a shower, you're letting your prefrontal cortex kind of relax a little bit. Those are good moments, too.

Carolyn Gregoire:

Yeah. I was thinking about meditation actually with just this [inaudible 00:32:10] idea of creating space, because that's kind of a metaphor for this process. There's different types of meditation, and meditation, that's very much about single-pointed focus. It's actually not the best for creativity. Like a more Zen kind of Vipassana approach, whereas something called open monitoring meditation or mantra meditation, where you're having a really wide open focus and you're letting things flow through. The idea is to, instead of focusing on one place to just open and expand the awareness.

Carolyn Gregoire:

That's actually been shown that that really improves people's scores on tests of creative thinking. So it's like being able to switch between a really clear single pointed focus and then to open up and expand is important. And I think in the collaboration, you could say that as well. It's like the time together is like that, focused kind of energy, but then you need to step outside and expand and open up. If you're always in the focused energy, you start to get kind of stuck.

Daniel Stillman:

What's coming up for you, Scott? I'm just watching your face processing.

Scott Barry Kaufman:

I couldn't have said it better than what Carolyn just said.

Daniel Stillman:

That's awesome.

Scott Barry Kaufman:

She nailed it.

Daniel Stillman:

She's a communicator. I'm coming back to these points. The high tolerance for dissonance, ambiguity, like the ability to step away from the work when it's not done seems to me to be what we're pointing to. It's like we're saying that we have to trust the process, which means we have to be focused, and then we need to walk away from it. We have to trust that the work will still be there when we get back, and also we will be different and we will see it differently. Which is not trivial.

Daniel Stillman:

I think for a lot of us, it becomes an itch we have to scratch. And there is this temptation, as you said, Carolyn, or I think Scott used the word, to bludgeon it, to just squeeze out more mind juice, if that was a thing we could do, right? Like, "Well, I'm just going to bang this one out, and I'm just going to produce." But I'm not hearing that that's what creates real sparks, emergence of something new as opposed to something that's conventional or expected.

Scott Barry Kaufman:

I get the sense that for a lot of creative people, the reward is inherent in the process and it's not so focused on the goal and focused on producing the work and making sure the product gets out there. You have a lot of creative people that enjoy the process so much that it's like, "Oh, now it's out there. Yeah. I forgot." I mean, I'm kind of that way. Once the book's out there, I want to move onto something else. I don't particularly love the promotion part of it. I have to be quite frank.

Daniel Stillman:

Yes. I apologize for calling you back so far.

Scott Barry Kaufman:

No, this was special. This was like a really special moment you made happen, so I must thank you for doing that. But I hope you see my point-

Daniel Stillman:

Yeah.

Scott Barry Kaufman:

... that to me, creativity mirrors the self-actualization process more generally. It's a never ending process. One goes their whole life continually growing and learning and finding meaning. And to me that's what's enjoyable. That's what's enjoyable about life. It's the continuous nature of the change in the learning and the creating. It's not the doing, at least for me, and I can say a lot of creative people.

Carolyn Gregoire:

Yeah. And I think learning to manage the tension because there is that joy in the process, but there's also the tension that can feel so overwhelming and unbearable at moments. And that even as creative people who have a higher tolerance for ambiguity and dissonance, it can still be uncomfortable. And so I think part of it is, yeah, how do we find our own ways to manage that tension and that dissonance? And this way it sound kind of weird and silly, but for me, I really like visualization and something I've learned to do. I found that I get overwhelmed in a project when I'm just holding all of this information in my head for a really long period of time and I don't know what I'm going to do with it. And that, it can be really not helpful for me.

Carolyn Gregoire:

That's the part that I don't like. And so I've learned to, like, I take it all at the end of the day and I put it into a cauldron. I visualize that and [inaudible 00:37:10] stir the cauldron and then I leave it to bubble and all mix together. And it actually kind of helps because I'm training myself to let things simmer and not keep it at the front of my mind all the time so I'm trying to figure out the problem. It's like, "Okay, just putting all of these ideas into this melting pot, letting... And I'm giving myself space to step away." But I think we all have to find our own ways to learn how to work with that, with the dissonance and the tension, and to remain in a state of not knowing and of creative percolation, which is while we have the joys of the process, we have the struggles in equal measure.

Daniel Stillman:

Yeah. So I'm glad you looped back to that, Carolyn, because when this question of what's... When I said a map for being able to trust the process, you gave us a key, which is great, and the ability to say that stuck is information. Instead of rejecting uncomfortable feelings, we can become aware of them. We can lean into them and just know that it's information is really important. And I don't know, maybe my notes aren't so good, but Scott, if there was a key you were going to put on our key chain to be able to trust the creative process, is there one more key or a key of, as my dad likes to say, a used key is always bright. What do you feel like is your brightest key to trusting the process?

Scott Barry Kaufman:

Oh, well, it's also trusting yourself. It's trusting your own capacity to fail and get up again, and being able to be comfortable in the space of trial and error. A lot of people's being is not very comfortable with trial and error. The second they have an error, they're done. They're not trialing again. I mean, look, I got an interesting taste from this. I tried out stand-up comedy recently. It's been a long-term dream of mine, and it's interesting. Some jokes fall flat, and you're like, "Okay, we've got to bring that one to the laboratory and tweak some words and then try it again. See if it gets a laugh." That trial and error process to me is fun. It's something I trust myself that I can learn from my mistakes. I think that's a big key, is that you trust that you can learn from mistakes so you're not so scared of mistakes.

Daniel Stillman:

When I was a younger man, I was much older in the sense, in the Bob Dylan sense. I really wanted to not make mistakes. I thought the only way you learned was by doing things right, and it's a heavy burden to carry. Ironically, I mean, we all know this, that no experiment ever fails. Experiments are information, but there is a lot of fear that comes from looking bad, from falling flat, of our own expectations or expectations that we think others have of us. So I think this-

Scott Barry Kaufman:

That's a really brilliant point.

Daniel Stillman:

Well, I mean, I think you're giving us good advice and it's important. It's hard advice, but it's important advice.

Scott Barry Kaufman:

It's brilliant. I never quite thought of it that way. No experiment fails and you're so right. It doesn't make sense to do a psychology scientific study and for it to fail. You're just doing a study. It's, wow. I mean, look, Daniel, I thought that was brilliant.

Daniel Stillman:

Got the price of admission. There you go. We created value.

Scott Barry Kaufman:

I agree with you. I agree with you. Yeah.

Carolyn Gregoire:

Yeah. I agree with that point, too. So many people say that persistence is the most important key, and I think part of that is just that you get to know the terrain and you've realized that the failure which is in your mind, this big, scary thing when you haven't experienced it or haven't experienced it that often, the more you do it, you realize, first of all, it's not that bad and you'll be fine. And on a deeper level, it actually will often redirect you in a really interesting direction. I mean, I started working on a personal writing project right after Wired To Create that I totally abandoned and walked away from, but it actually led me in so many interesting directions and sparked some kind of synchronicities, actually, similar to what I experienced with the book with Scott, that never would've happened if I hadn't had that failed project.

Carolyn Gregoire:

And so while it felt kind of awful at the time, because it was my first major failure, I'm just so grateful for it. It really was a huge part of the path. Someone once told me, the mistakes are the path. I think sometimes we feel like we're messing it up or we're getting off of our path, whether it's your career path or your path of personal growth, but you can't mess up the path because you're the one creating it. So, it's all part of it.

Scott Barry Kaufman:

I love that, too. I love that. You can't mess the path because you created it. Wow. Yeah.

Daniel Stillman:

One of the things that's come up in my research so far is that... I mean, this is really like relationships. We have all had rebounds. You mentioned this way earlier in our conversation. You finish a big creative project and you just want to get cruising on the next one. And sometimes it can be the love of your life and other times it can be a rebound, but you will never know until you get into it.

Carolyn Gregoire:

Yeah. And the rebound serves its own kind of [inaudible 00:43:03] I guess.

Daniel Stillman:

The rebound serves its own... It's information.

Carolyn Gregoire:

It's inferior to the great love, but it still has a particular purpose in the moment.

Daniel Stillman:

So we are just about coming up against time, which means I have to ask you, what have I not asked you that I should have asked you? Scott, what is still unsaid when it comes to this very important topic of Wired To Create together?

Scott Barry Kaufman:

Ask Carolyn if she'll write another book with me someday. I'm joking. I'm joking. I won't put her on the spot, but-

Daniel Stillman:

The jumbotron is on us both.

Carolyn Gregoire:

We have an idea that's been-

Scott Barry Kaufman:

We have an identity.

Carolyn Gregoire:

... [inaudible 00:43:44] for a while. It's all about the timing. So we'll keep you posted on that.

Scott Barry Kaufman:

That's true. That's very true.

Daniel Stillman:

Wow.

Scott Barry Kaufman:

That's correct. That's what it's all about. So is there any questions you didn't ask us? I don't think so. It was nice to talk about the creative process again, after all these years with Carolyn.

Daniel Stillman:

Thanks, Scott. Carolyn, any unsaid...

Carolyn Gregoire:

Anything unsaid? Yeah, I guess it's maybe been said. I'm circling back to the theme of conversation, but it's really just through doing that we learn, I think. I guess I'm just really feeling from this conversation and how that we learn how to trust ourselves and learn how to trust the process and something that... The subtitle of the book was Unraveling The Mysteries of the Creative Mind, and something that we talked about a lot was just how mysterious the process is.

Carolyn Gregoire:

And I still say that all the time, is that creativity is this huge mystery and I know nothing about it because it's all just beyond us in a certain way. You can't boil it down into a formula, but at the same time, yeah, you keep doing it and you start to recognize a path and you start to recognize these trail markers. I think that's how we can start to feel a little bit less scared or overwhelmed or burdened by the challenges and start to enjoy it a little bit more. So, yeah, that's what I'm feeling right now.

Daniel Stillman:

And it goes back to... I've been just sitting with the thing that Scott you said earlier about this journey of self-actualization and growth as a human being, and just increasing our capacity for complexity and self-manifestation, I guess, you might say. I mean, this is what do we take from each experience and what do we bring forward from it?

Scott Barry Kaufman:

Bingo. Bingo.

Daniel Stillman:

Where should people, should they want to learn more about all things y'all, where should they go on the internets to find out more about the things that you all are and do, if you don't mind-

Scott Barry Kaufman:

Check out my podcast. It's called The Psychology podcast and scottbarrykaufman.com, and the Center of Human Potential, humanpotential.co. These sorts of things will get you in roads to the world of SBK, as my friends affectionately call me.

Carolyn Gregoire:

And you can find more of my work on my website, carolyngregoire.com. I have a lot of my personal writing there and I also work as what I call a book doula. That is a mix of being an editor and also a guide in exactly the process that we've been talking about, and something that I've come to really enjoy and love. So, you can learn more about that on the website.

Daniel Stillman:

That's awesome. Well, thank you two very much for taking this walk down memory lane and being so reflective. Being a reflective practitioner is really important, so I appreciate you making time to do this with me.

Scott Barry Kaufman:

Thank you for inviting us, Daniel.

Carolyn Gregoire:

Yes. Thanks for having us.

Scott Barry Kaufman:

A real pleasure.

Daniel Stillman:

Well then I'll call "scene."

Building an Intelligence Engine

I’m excited to share this rambling and wide ranging conversation with Srinivas Rao.

Srini is the host of The Unmistakable Creative Podcast, and has recorded over a thousand episodes with such luminaries as Danielle Laporte, Tim Ferriss, Seth Godin and me! Srini describes his podcast as “If TEDTalks met Oprah”.

Srini has interviewed so many different types of folks, from bank robbers to billionaires. He also has a business degree from UC-Berkeley and an MBA from Pepperdine   University.

We talk about podcast interviewing (meta, I know!) and we unpack a topic that’s close to both of our hearts: creative output.

One of my early podcast episodes was with Sara Holoubek, CEO of Innovation Systems consulting firm Luminary Labs. Sara introduced me to the idea of having what she called an “Intelligence Engine'' - a process by which organizations turn insights into action and action into opportunities, not just every so often, but consistently and regularly. It’s not a dissimilar idea from Jim Collins’ “Flywheel effect” in that, ideally, you tune up your engine often, and even upgrade it when you need to.

One of my core beliefs is that conversations exist at different scales, and that they act in similar ways at these different scales. I also might take the idea of a conversation too far…in that I feel that any iterative, adaptive cycle is, in essence, a conversation.

So, Sara’s Intelligence Engine is essential for a healthy, growing company’s conversation with the world - after all, intelligence at the product and/or organizational innovation level requires a consistent cycle of making or creating new things, testing or trying those things out and reflecting on how it went, ie, harvesting insights. That’s an innovation conversation, at scale.

That cycle is pretty much the same at the level of the individual. We all need to seek new input, make and try new things, and then reflect and inspect the results.

Serendipity Engine vs Intelligence Engines vs Curiosity Engines

As with organizational intelligence, individual intelligence engines need to have a balance of intention and wandering. We need to be actively seeking new insights and ideas that matter to us, while also being open and curious about the unexpected. So, having a curiosity engine, like my guest Glenn Fajardo suggested  in our episode on connecting remote teams, is a powerful way to rev up your intelligence engine, for yourself, your team and your organization.

Managing the flow of input, insight, and output

If there is one key takeaway from this episode, it’s that the open/explore/close // diverge/emerge/converge ARC of our own intelligence conversation is input-insight-output.

Srinivas’ top tips for building your own personal intelligence engine:

  • Limit your Input

  • Diversify your input

  • Read books, not articles (they’ve digested complexity already!)

  • Use a networked tool to capture your smart notes (srivas recommends Mem.ai which I also use!)

  • Reflect and Connect dots regularly

  • Monotask to reduce the cognitive costs of task switching (check out my friends at Caveday and use the code 1STMONTHONE to get month of community-based monotasking support for $1 or use TRYACAVE21 to get your first cave free)

Links, Quotes, Notes, and Resources

The Unmistakable Creative podcast

Sara Holoubek on Human Companies and Solving Problems that Matter

Three Systems Every Creator Needs to Build by Srinivas Rao

You're Not Listening by Kate Murphy

The Life-Changing Science of Detecting Bullshit

Effortless Output in Roam course by Nat Eliason

How to Take Smart Notes by Sönke Ahrens

Maximize Your Output course by Srinivas Rao


Minute 6

Daniel Stillman:

Before we got started you were saying a lot of people are terrible interviewers, and I'm wondering what makes a terrible interview? And then maybe we can backtrack into what makes an amazing one.

Srinivas Rao:

Well, yeah, I think what makes a terrible interview is one where the person is not attuned to the guest or the questions or stilted, you can tell they just have a list of questions that they're going through. That's probably the worst thing is you just feel like you're answering a list of questions. They also don't do the research. I think there's this balancing act with research, people think I do more research than I do, but at most I will read somebody's webpage.

Of course every single person who writes a book, I read their book, that's my default policy, I'll cancel the interview if I haven't finished the book. And nobody ever gets mad about that, because it's, to me, the sign of respect. Plus it gives you a scaffolding to have a conversation. I think there's this also combination of not just the ability to ask good questions and show that you understand your subject, but there's a social component of this, right?

There's an energy exchange that a lot of people I think don't quite get, they think they can just press record and the conversation will be interesting, which it doesn't really work that way. I think the thing that I find is when people basically build questions off of the answers you're giving them, that's what I do, so I think scripting questions in advance is literally probably the worst thing that makes for a bad interview.

And the other, like I said, is that people will ask you questions when they should know all this. I had somebody once email me and say, "Hey, could you send us the questions you want us to ask?" And I was like, no, that's your fucking job, I'm being interviewed. And I'm like, are you serious? You want me to send you the questions that I want to be asked? Isn't that your job?

Minute 10

Daniel Stillman:

But some people do go to the script, and I think the best stuff happens, as you say, when you get off script. So, how do you get people to go off script?

Srinivas Rao:

Ask them things they've never been asked before. So, you've been a guest and you know that when I start a conversation, you're just like, "What the hell does this have to do with my work?" And so I always preface [inaudible 00:10:11], "Look, I'm going to ask you questions that seem like they have nothing to do with your work, but you'll see there's a method to my madness, we'll get there." And the reason for that is that human beings are hardwired to listen to stories.

And the other thing is that you can't answer any of those questions without telling a story. You can't just spout off the same old bullshit that you have on 1,000 other shows, it's part of why we turned down Gary Vaynerchuk as a podcast guest, because I was like, not going to happen unless he agrees to my terms.

Minute 14

Srinivas Rao:

If you have the same guest on every show saying the same things, listening to the same people, you're not really reaching an audience, you're kind of inside of this filter bubble or this sort of echo chamber which that's one of the reasons I constantly go out of my way to find people that you've never heard of because, one, I don't want to be exposed to the same bullshit over and over again, because that makes your worldview myopic and you can't be insightful and you can't have original insight if you have a myopic worldview or your content consumption is just the same old online marketing garbage

Minute 15

Daniel Stillman:

Well, so let's loop it back around because I think my impression is that your podcast is designed potentially to optimize for the same thing that I think I'm optimizing my podcast for, which is my own learning, my own insight and creating more creativity for myself as well. It sparks new ideas and new things for you. Is that a fair perception? From what I'm hearing you say.

Srinivas Rao:

That's spot on, if you think about it, I just told you I choose every guest based on what I'm curious about, so it's kind of like, I'll give you an example, I had a former guest, Amy Chan, who wrote this really great book called Breakup Bootcamp, which was all about the science of recovering from heartbreak. She shared something that she was doing with a friend who was a professional dominatrix. And I'm like, now that sounds fucking interesting. I want to talk to her. And she was amazing, she was wicked smart, and it was great because she shattered so many misperceptions that people might have had about sex work. She was valedictorian at her high school, went to UCLA on a full ride, Berkeley graduate school.

And it's like, what? That's not the path to professional dominatrix that most people would think. So, it was really cool to get to hear that kind of story because I think that that's the other thing, is that one of my goals really is to challenge people's perceptions of what certain people are like, because media is a powerful tool to shape both perception and misperception.

Minute 18

Srinivas Rao:

Well, the fact that people make these blanket statements like everybody should start a podcast or these are the things you should do to become a millionaire. I'm like, yeah, okay, well, no, because the context matters. There's nothing everybody should do.

More About Srinivas

Srinivas Rao is a top branding and creativity keynote speaker, host of the podcast The Unmistakable Creative, and the bestselling author of The Art of Being Unmistakable. He has been the conference keynote speaker for The International Live Events Association, The Healthcare Design Expo, Catersource, and The International Association of Event Planners. He has also worked with corporations like Citibank, Meredith Corporation, and Bayer.

Full Transcript

Daniel Stillman:

Well, then I will officially welcome you to The Conversation Factory, Srinivas Rao, you really need no introduction, but maybe you do. How do you usually introduce yourself?

Srinivas Rao:

It's weird, I think people have this misperception that I'm more well known than I really am. I jokingly say I'm the most connected person that nobody has ever heard of. I think that I'm far more known because of my guests than for my own work, and so to sum it up, I'm the host of The Unmistakable Creative Podcast, where you've been a guest, along with porn stars, bank robbers, drug dealers, performance psychologists, authors, entrepreneurs, artists, just people who I think are interesting. That's my default is to just choose based on whoever I'm curious about.

Srinivas Rao:

These days we have no shortage of people with pitches, but I am pretty adamant about the fact that I don't choose people based on fame or status or any of that, I choose people based on how interesting I think their story is, and it really comes down to everything is always done in service of two things, a listener and a story. Is this a story I want to tell? Is this a story that will benefit our listener in some way?

Daniel Stillman:

So, I think, man, the reason I thought it would be interesting to talk to you, to me the idea of having a creative conversation versus an interview, before we got started you were saying a lot of people are terrible interviewers, and I'm wondering what makes a terrible interview? And then maybe we can backtrack into what makes an amazing one.

Srinivas Rao:

Well, yeah, I think what makes a terrible interview is one where the person is not attuned to the guest or the questions or stilted, you can tell they just have a list of questions that they're going through. That's probably the worst thing is you just feel like you're answering a list of questions. They also don't do the research. I think there's this balancing act with research, people think I do more research than I do, but at most I will read somebody's webpage.

Srinivas Rao:

Of course every single person who writes a book, I read their book, that's my default policy, I'll cancel the interview if I haven't finished the book. And nobody ever gets mad about that, because it's, to me, the sign of respect. Plus it gives you a scaffolding to have a conversation. I think there's this also combination of not just the ability to ask good questions and show that you understand your subject, but there's a social component of this, right?

Srinivas Rao:

There's an energy exchange that a lot of people I think don't quite get, they think they can just press record and the conversation will be interesting, which it doesn't really work that way. I think the thing that I find is when people basically build questions off of the answers you're giving them, that's what I do, so I think scripting questions in advance is literally probably the worst thing that makes for a bad interview.

Srinivas Rao:

And the other, like I said, is that people will ask you questions when they should know all this. I had somebody once email me and say, "Hey, could you send us the questions you want us to ask?" And I was like, no, that's your fucking job, I'm being interviewed. And I'm like, are you serious? You want me to send you the questions that I want to be asked? Isn't that your job?

Daniel Stillman:

Yeah, it's so interesting because on one level, I was on a podcast recently where somebody sent some of the general questions they asked, and they were reflection prompts for me. On the one hand I was like, you want me to do work before I go in to do this interview? On the other hand, it gave me some room to think, but then there's this question of is it spontaneous versus not?

Srinivas Rao:

I never send anybody questions and even if I do, I don't ask them. I'll send them, and I'll be like, "Here's a few for you to think about, I'm probably not going to ask any of them." Because here's the thing, if you ask somebody questions they've answered 1,000 times, then they're going to say the same damn thing they've said every other show, so you basically don't get anything insightful. My goal is always, to me, I know the best compliment you could possibly get when you ask somebody in a question is when somebody says, "Nobody has ever asked me that before."

Srinivas Rao:

So, Kate Murphy wrote that amazing book, You're Not Listening, which I think is probably the bible for podcast hosts as far as I'm concerned. And the funny thing is if I wrote that book it would've been called Nobody Has Ever Asked Me That Before. That would be my title for a book about podcasts, but I have no interest in writing a book about podcasting.

Daniel Stillman:

Fair. Well, two things I heard that I think are really interesting is the list versus being responsive.

Srinivas Rao:

Yeah.

Daniel Stillman:

And so that's basically a huge difference between what I would call a creative conversation or one that is dead.

Srinivas Rao:

Yeah, absolutely. You wouldn't go to a first date with a list of questions on a piece of paper, would you?

Daniel Stillman:

Well, some people do. Some people who get really nervous do, and I don't think they're great dates. But here's the flip side of this is I think that would maybe, I would say, make a creative conversation is when I've definitely interviewed people and certainly heard podcasts where people just go to the script. And so I think one part of it is the questions, and teeing up those softballs, like, "Tell us about your book," which is so general as to not be helpful. But some people do go to the script, and I think the best stuff happens, as you say, when you get off script. So, how do you get people to go off script?

Srinivas Rao:

Ask them things they've never been asked before. So, you've been a guest and you know that when I start a conversation, you're just like, "What the hell does this have to do with my work?" And so I always preface [inaudible 00:10:11], "Look, I'm going to ask you questions that seem like they have nothing to do with your work, but you'll see there's a method to my madness, we'll get there." And the reason for that is that human beings are hardwired to listen to stories.

Srinivas Rao:

And the other thing is that you can't answer any of those questions without telling a story. You can't just spout off the same old bullshit that you have on 1,000 other shows, it's part of why we turned down Gary Vaynerchuk as a podcast guest, because I was like, not going to happen unless he agrees to my terms. And the funny thing is, who the hell are you to dictate terms to Gary? I'm like, I'm Srini Rao, the host of The Unmistakable Creative, this is how we roll. You don't like it then go fuck yourself.

Srinivas Rao:

Honestly, I don't have anything personally against Gary Vaynerchuk, but the thing is he's just one of those people that I feel like says a lot of the same things on all the same shows, and it's like, not going to happen, not on our platform, I just won't allow that. And so I basically, I think somebody on our PR team, [inaudible 00:11:12] team, was like, "Hey, Gary wants to be on your show or he's expressed interest," and I was like, all right, great, here are the three conditions on which we'll have him on the show.

Srinivas Rao:

Every show is an hour, he has to listen to an episode beforehand, and, three, it cannot be about anything social media related, it has to be about his personal story because my audience could care less about anything social or tactics or marketing. And I think that is probably the last time I'll ever hear from Gary Vaynerchuk, which is fine because I don't feel like I'm missing anything. But that's the thing, it really comes down to asking questions that elicit stories.

Srinivas Rao:

Because the thing is, you don't want a question that somebody can give you a bullet point answer to, right? And the problem is that a lot of these professionals are media trained by a publicist, a publicist will be like, "Keep it short and sweet, stick to the talking points." When you've been on my show, my first instruction is do the exact opposite of whatever your publicist has told you. Because the problem is, publicists are trained to prep people for short form, 10 minute interviews on NBC or whatever, but this was a long form conversation.

Srinivas Rao:

And you need that freedom to go to different places. I'll have guests walk out on an interview, it's like an hour of therapy sometimes, what they'll tell me. Mainly, again, I'm asking questions that I genuinely am curious about, and that's the other thing, I think people, they mix up the idea of asking questions that they think are going to be valuable to listeners, and then questions they're genuinely curious about. And those two things are not mutually exclusive, in fact you're better off going with something you're curious about because that's going to come across.

Srinivas Rao:

Whereas if you ask this scripted list of questions, it just doesn't feel very genuine, it feels almost robotic. There are people who literally use the same questions for every show, and I'm like, then why the hell do you even do the interview? Why don't you just have the guest record their answers and you guys don't have the waste the time to be on air together?

Daniel Stillman:

Well, Tim Ferriss does do some shows like that. I find them a little less interesting, I think because there isn't that rhythm of a creative conversation, the energy between two people responding to each other.

Srinivas Rao:

Totally, yeah, that's one thing that I think is lacking from a lot of these conversations. Plus, at this point the interview based format where you just interview entrepreneurs or online personalities, I know this because I was so early to this, it's kind of saturated and that's the reality. People don't think about this from a business standpoint either if they're serious about it, it's like, okay, if you enjoy doing this and you have no outcome in mind then great, that's cool.

Srinivas Rao:

But if you're trying to compete with what is effectively the gigantic circle jerk, then you're really not going to have much traction, because you're not doing anything that is substantially different or unique from whatever else is out there. Because that's the thing, now you're making me think, I just had an article idea, the commoditization of interview based podcasts, because that's what's happened. It really has.

Srinivas Rao:

If you have the same guest on every show saying the same things, listening to the same people, you're not really reaching an audience, you're kind of inside of this filter bubble or this sort of echo chamber which that's one of the reasons I constantly go out of my way to find people that you've never heard of because, one, I don't want to be exposed to the same bullshit over and over again, because that makes your worldview myopic and you can't be insightful and you can't have original insight if you have a myopic worldview or your content consumption is just the same old online marketing garbage that [inaudible 00:14:54].

Srinivas Rao:

I remember people asked me when I grew a blog, the best thing that I ever did, my blog started to grow the day I stopped reading books about how to grow a blog. I stopped reading all online marketing, all social media books. And that was the best, that's when I finally started to have real insight.

Daniel Stillman:

Well, so let's loop it back around because I think my impression is that your podcast is designed potentially to optimize for the same thing that I think I'm optimizing my podcast for, which is my own learning, my own insight and creating more creativity for myself as well. It sparks new ideas and new things for you. Is that a fair perception? From what I'm hearing you say.

Srinivas Rao:

That's spot on, if you think about it, I just told you I choose every guest based on what I'm curious about, so it's kind of like, I'll give you an example, I had a former guest, Amy Chan, who wrote this really great book called Breakup Bootcamp, which was all about the science of recovering from heartbreak. She shared something that she was doing with a friend who was a professional dominatrix. And I'm like, now that sounds fucking interesting. I want to talk to her. And she was amazing, she was wicked smart, and it was great because she shattered so many misperceptions that people might have had about sex work. She was valedictorian at her high school, went to UCLA on a full ride, Berkeley graduate school.

Srinivas Rao:

And it's like, what? That's not the path to professional dominatrix that most people would think. So, it was really cool to get to hear that kind of story because I think that that's the other thing, is that one of my goals really is to challenge people's perceptions of what certain people are like, because media is a powerful tool to shape both perception and misperception. Unfortunately media in our modern day does more to shape misperception than it does to shape truth, with misinformation.

Srinivas Rao:

And we don't really look beyond the surface of what we see. And so the result is copious amounts of bullshit. We literally had a guy who wrote a book called The Life Changing Science Of Detecting Bullshit. And the thing that really struck me as I was writing about this is that on a large enough scale, you can take popular platitudes, cliches, fad diets, and basically mistake bullshit for truth because enough people agree.

Srinivas Rao:

But the thing is that if you don't seek evidence to the contrary and you don't seek evidence that something is overwhelmingly true, then you're kind of just lying to yourself. You're just taking something at face value and that's half the problem with the way we consume content today. We're inside these walled gardens. The other thing is that context is something that really matters, you and I may have talked about this and I feel like I did talk to you about this, I feel like I can't stop talking about it, but it's true.

Srinivas Rao:

Context makes a big difference in terms of the results that you see people get, particularly with self help, context really matters because people leave out the context when they sell things, they leave out the context when they consume things, they leave out the context when they look at their role models. And it's kind of like, well, look, you're not going to get my results. I have certain skills that, honestly, and I also have certain advantages that you can never replicate. I got a 10 year head start on a massive cultural trend. And we don't talk about that stuff. That pisses me off beyond belief. This is why I always joke that my first book, Unmistakable-

Daniel Stillman:

Which pisses you off? I think I missed that.

Srinivas Rao:

Well, the fact that people make these blanket statements like everybody should start a podcast or these are the things you should do to become a millionaire. I'm like, yeah, okay, well, no, because the context matters. There's nothing everybody should do. And the problem is the fact that we believe that. I think that in one way people are like, maybe I'm not as inspiring, I think I've become much more realistic. And, honestly, the thing that one of the iTunes reviews that I was most proud of was like, "There's no fluff here, no feel good fluff." And that was, to me, the ultimate compliment because that's what so much of self improvement has become, is feel good fluff that doesn't actually lead to anything.

Daniel Stillman:

Yeah. Well, so this goes, just to really highlight something for folks who might be listening to this conversation, to me, the ability to have a creative conversation with someone, to learn from them, to get insight from them, is for a purpose. And what is the purpose for you? The things that you are learning, that you're developing and growing, what is the output that you want to do with it?

Srinivas Rao:

Yeah, that's a good question. Well, so the joke I've always said is if I could actually take all the advice of my podcast guests and apply it to my life, I would be a billionaire with six pack abs and a harem of super models.

Daniel Stillman:

I know, you would be a galaxy brain me.

Srinivas Rao:

No, think about it, I have probably the largest encyclopedia of random shit inside my head of probably anybody you know.

Daniel Stillman:

Yeah, and you can't and haven't acted on all of it, which is fascinating to me.

Srinivas Rao:

Well, some of it probably wouldn't make sense to act on, I always joke, if you want to rob a bank, become a porn star, or run for president, I can either tell you how or introduce you to somebody who could teach you.

Daniel Stillman:

Yes. So, then what's it all for? Seriously.

Srinivas Rao:

Well, I think there is this love of learning, but to me more than anything it's to mix up other people's ingredients to diversify my perspective, because it takes us back to that whole myopic viewpoint thing, I think that Robert Greene gave me this metaphor once when we were talking about the concept of mastery. And he said the analogy is biodiversity. The more species that you have in the ecosystem, the richer that ecosystem will become.

Srinivas Rao:

And so the more diverse the set of people I interview is, the more diverse I'm going to be in my thinking, my ability to ask questions, and my ability to find new guests, and that is something I pride myself on is the fact that that's a very common comment is why do people listen to Unmistakable? It's because we have guests that you will honestly never find on any other show, because they're not famous, they don't have huge personal brands.

Srinivas Rao:

Yeah, we have all those people and it's funny because every time somebody introduces me and they kick off my intro by saying, "You've interviewed Seth Godin and Tim Ferriss," and I'm like, listen, those are the least interesting people. Seth is fantastic, I love Seth.

Daniel Stillman:

They are framed behind you, if you're listening at home, I love the...

Srinivas Rao:

Yeah, so that's the thing, it's not that there's anything wrong with Seth, but you ask me, okay, so you see the other picture behind me on the wall, you may not know who that is, but Justine Musk, would I rather talk to Justine or... Everybody knows Elon, Justine is brilliant, there's so much wisdom inside that woman's head. Obviously she's had a front row seat to Elon in a way that none of us ever will, and she herself is absolutely one of the most thoughtful, brilliant and just poetic writers you'll ever come across.

Srinivas Rao:

She has a way of explaining things and understanding things that you're kind of like, wow, she's just wicked smart. And so I think that that's one thing that I look for is really, more than anything, to go out of my way to find these people that I'm curious about. More than anything it's I want a diversity of ideas in my idea ecosystem, so that I'm not just drawing from one well to come up with ideas, because you want what they call I guess in design thinking, this is probably more your forte than mine, but the reason this is fresh on my mind is I was going back through Tim Brown's book, but it's a diversion thinking, right?

Daniel Stillman:

Yeah.

Srinivas Rao:

Where it really is a multidisciplinary way to give yourself an education I guess is the way that I think about it, because you'll pull these random ideas from conversations, and you don't even know how they'll affect you. That's interesting, I should try that. That's part of what drives it, the purpose really more than anything is to satisfy my curiosity, at the end of the day.

Daniel Stillman:

So, I think this is a really interesting segue, because we're zooming in and I always want to zoom out, because it's very clear that you do a lot of preparation for the conversation, and then there's all the stuff that happens during the conversation, the moves you make to make sure that you get somebody off script and don't just ask them a list, et cetera. And then now we're talking about all the stuff that happens after the conversation. And this is where I'm curious about the second brain mindset and the databasing of your insights, the idea that your ideas can start to have sex with each other.

Daniel Stillman:

And this is where I think maybe my pushback, we were talking about the benefit statement, the marketing of your second brain, and is it about keeping track? Is it about maximizing input, or output rather, but I think there's also this question of how they cross fertilize and cross multiply. And to me, I like the maximize output idea, because to me I want to be able to pull threads together and say, I was thinking about writing these three things, and you know what, they're actually just three chapters in one longer essay.

Srinivas Rao:

Right, you just gave me the subheader now.

Daniel Stillman:

So, what's the subheader?

Srinivas Rao:

Well, you gave me the update to the subheader, because somebody had said to me, and I literally took this word for word from our survey data, it was just like, build one trusted source where everything is, where you can basically connect your ideas together, come up with new ones, and manage everything without having to use 50,000 different apps.

Srinivas Rao:

But, yeah, here's the thing, part of the reason that I got into all of this is the very thing that we were just talking about. I wanted to be able to access the knowledge that is inside of my head from interviews, from books, and be able to actually put it into action, which this is great, you're actually giving me so much fodder for the copy now. I was trying to figure out how to explain why this was so important to me, but you just gave it to me, so thanks.

Daniel Stillman:

It's my pleasure, maybe you can explain it to me now.

Srinivas Rao:

Yeah, so the thing that if you look at the consumption habits that I have, one, I probably consume more content than the average person, particularly in terms of books. I don't listen to podcasts, I hardly ever read anything online. Every now and then, I've stopped reading Medium, I think Medium has pretty much just gone down the toilet as far as I'm concerned, there's really nothing good there anymore.

Srinivas Rao:

So, I read two blogs, I read Cal Newport and I read Seth Godin, that's about it. And then every now and then I'll come across an article or two, every now and then I read [inaudible 00:26:11] newsletter, because I'm subscribed to it. But for the most part, I don't consume very much. I do consume books, that's the primary thing that I consume is books. And I like some TV shows, but I don't even listen to podcasts, despite hosting one, I actually don't like them. I don't like listening to them. They're just not my preferred form of media consumption, which is kind of bizarre considering I make a living doing this.

Daniel Stillman:

It's not bizarre, it just makes you a hypocrite, [inaudible 00:26:39].

Srinivas Rao:

No, I honestly think that's been one of my biggest advantages in terms of being able to be insightful and original, because I have no idea what people are doing on their shows so I don't interview people that other people interview, I don't hear the questions they're asking, I remember somebody once told me, "You're interviewing this person, you should listen to the interview he did with this other person." I'm like, why the hell would I do that? I don't want to sound like that other person.

Daniel Stillman:

Well, sometimes I listen to one or two other interviews just so I can not ask those questions, to that point you were asking before.

Srinivas Rao:

Yeah, that is fair, right? And the thing is that I'm not worried about that ever because I know that I won't ask those questions at this point, that's never a concern for me because I already know that people don't ask the questions that I do.

Daniel Stillman:

Yeah. It's really interesting because you don't have the contexts, I'm guessing, in which people consume a podcast vary. It used to be the drive or commute, sometimes I'll listen to one where I'm folding laundry, but it's not everybody's context, some people just want to have silence or music while they're folding their laundry, or have someone else fold their laundry, I don't know how you live your life.

Srinivas Rao:

Ideally, yeah.

Daniel Stillman:

But so I guess the question is, and maybe this is the question of how do you digest a book? You have your second brain, you use Mem, right?

Srinivas Rao:

This is good, yeah, this is actually a good question. So, a lot of this was honestly changed in this year, it wasn't until this year that I got so refined about it, and credit where credit is due. So, first I took Nat Eliason's course called Effortless Output in Roam, because I wanted to understand it, and I hated the user interface of Roam. I was just like, I love this idea conceptually, but it's just clunky, it's ugly, I think it was really meant for academic research.

Daniel Stillman:

And just for people who don't have the context, Roam Research, some people rave about Roam, it's another databasing tool.

Srinivas Rao:

The function is phenomenal, but for me the user interface was a big issue, I just found it clunky and difficult to navigate. Even Cal Newport was like, "I use Roam, I don't think I use it well," and I felt the same way. So I basically took everything that I saw in Nat's course and I just said, all right, let me apply what he's taught me inside of Mem and see if I can replicate this conceptually. And so the thing that changed, the best way to explain this I think is in terms of studying for exams in college, because I think that that's a perfect way to really give you this jump off point for how I started to think about this.

Srinivas Rao:

There's a book called How To Take Smart Notes that a guy named Sönke Ahrens wrote, and that book is kind of a goldmine in terms of your ability to really draw insights from the content that you consume and to actually use it in a way that is useful. So, if you look at the average college student in terms of how they study, how they take notes, what do they do? They basically go to lectures, they try to copy down what the professor says, they do problem sets, they go to office hours, if you go to a gigantic school like Berkeley, you go to discussion sections where the TA explains the same stupid thing you learned in class and maybe you do more problem sets. And then so you kind of delude yourself into thinking you actually understand this idea.

Daniel Stillman:

Yeah, people highlight books, which is not how... You highlight it thinking, I now am letting myself know that this is important, therefore I will remember, but that's not how it works.

Srinivas Rao:

No, not at all. So, you took me to the next point, I remember at Berkeley sometimes you'd get these used textbooks, and somebody highlighted this entire fucking textbook, really? As if they're going to remember everything in the textbook.

Daniel Stillman:

Yes.

Srinivas Rao:

And then I had certain friends who almost never went to class and got straight As, and it was just like, what the hell are these guys doing differently? And what I realized is that... So, if we go back to high school, this is a good [inaudible 00:30:44]. We can't exactly do this linearly, because the funny thing is, once you start to understand how this works, you'll realize it's not linear. So, you go back to high school, and my old roommate, [inaudible 00:30:55], was like, "You were a straight A student in high school." I was like, I'm Indian, of course I was a straight A student in high school, my parents would have disowned me if I wasn't.

Daniel Stillman:

Well, there are some Indians that have parents that just don't like them and make them cry.

Srinivas Rao:

Yeah, the reality is we're conditioned to do that, straight As were not a question around our house. Nobody congratulated you for that, it was like, why the hell did you get a B? That's it. And that was invaluable because...

Daniel Stillman:

Yeah, that's the standing Asian parent joke. It's immigrant parents in general I think.

Srinivas Rao:

Totally, yeah.

Daniel Stillman:

It's like, come on.

Srinivas Rao:

You're Jewish, right? I hear that's pretty standard for Jewish people too.

Daniel Stillman:

Yeah, it's like, come on, you're just going to get an A and you should probably get a Masters degree, or what the hell are you doing with yourself?

Srinivas Rao:

And the A is basically the bare minimum, right? It's like this is the minimum standard of performance.

Daniel Stillman:

Yep.

Srinivas Rao:

And so, but here's the thing, you don't have to be smart to get good grades in high school. Any idiot can get good grades in high school if they're just semi organized, and does what the teacher says. Because all you're doing is largely memorizing and regurgitating, that's part of why we have such a fucked up education system, you don't want to get me started on all that. That rant is another podcast entirely.

Daniel Stillman:

Totally.

Srinivas Rao:

But the thing is that we don't actually learn, we memorize and we regurgitate, which anybody that can do that can get straight As in high school. But then you get to college, especially at a place like Berkeley, and the same thing that made you a straight A student in high school no longer works. Like I said, I only can understand this now 20 years later after being a C student at Berkeley, where you take an economics exam, so we go back to the whole thing of problem sets, highlighting and all that, right?

Srinivas Rao:

So, you think that you understand something, and then you go into an exam and it's presented to you in a context that you've never seen. And so suddenly, because you only understood it in the one context it was presented in, so suddenly, because you didn't elaborate on your understanding, which is critical. That's a big part of how to take notes. So, the premise of smart notes is that unlike your previous notes, people are like, isn't this really tedious and slow? And I'm like, yes, but don't you actually want to retain the knowledge that you've consumed and actually put it to use?

Srinivas Rao:

You'll get more out of doing this with one book than you would from reading 10 books and just underlining a bunch of crap and copying it and pasting it. This is not just copying and pasting books, and that's the thing, I used to do that as well. And so if you look at Ryan Holiday's note card system, that has effectively made him one of the most successful authors of his generation, a big part of it relies on elaboration of what you've consumed, and really looking at how it fits into the context of the work that you're doing.

Srinivas Rao:

And so the fundamental premise of smart notes, which basically [inaudible 00:33:58] Zettelkasten, which is a system that was invented by Niklas Luhmann, this German social scientist who wrote 58 books and published 500 papers in his life, is that instead of just copying what it is, he would make it a point to basically rewrite whatever insight he had in his own words and then link all those things together.

Srinivas Rao:

And now, with a modern day note taking [inaudible 00:34:22], and this is kind of hard to explain verbally because it's one of those things that when you see it visually it makes so much more sense, but inside of a note taking tool like Mem, you have this concept called bidirectional links, and bidirectional links are in a lot of ways, in numerous ways, the more you dive down this rabbit hole, the more you start to discover different ways of describing it. So, in a lot of ways it's kind of like Google's page rank but for your brain.

Srinivas Rao:

It shows you what keeps surfacing over and over again. But the other thing is that it allows you to have insight without taking immediate action on that insight. Sönke Ahrens had a really good way of putting this. He said, insight isn't something that you can plan for.

Srinivas Rao:

So you might be writing something, and while you're writing that one thing, you say, that sounds like a nice idea for a blog. But it's like, one sentence in one article is potentially another article in and of itself. And the thing is that you lose that idea because of the fact that you think I have to stop now and capture that idea. And that's where Mem comes in because you have bidirectional links and networked thinking.

Srinivas Rao:

The funny thing is that this is very counterintuitive. The irony is that we built all these tools to allow us to take notes, to organize information. And the irony of all of it is that they don't actually work the way our brain works. They're all designed to basically facilitate linear thinking. But anybody who has a brain knows that the brain is a network. It's not a hierarchy.

Srinivas Rao:

You have all these different dots that are connected inside, and that's what you do. It's not a coincidence Steve Jobs was like creativity is just connecting dots. Everything is just acting dots. And so what you're able to do as a byproduct of this is you start to connect dots between your ideas and you will quickly start to see that the more that you capture, the more you'll be able to create.

Srinivas Rao:

And so, if I showed you my own database right now, there's probably 5,000 notes in there, all of which are from books and other random thoughts. But the other thing is when you rewrite somebody else's insights in your own words, you'll also start to come up with your own insights that you didn't have before, just randomly, you'll be like, well, I didn't know that was going to happen. So you're basically feeding the ecosystem. There's a metaphor for this I can't quite... You're planting seeds is really what you're right. And you don't know when they'll bear fruit, and that's really why, the people who are prolific plant a lot of seeds.

Daniel Stillman:

So, I want to pull back and look at this arc that you've painted for us. If we're looking at the whole arc of the conversation of ingestion and output, I want to just paint it as it's a larger dialogue. And what I'm seeing is that you actually limit your diet. That's one thing that I heard you say is you're not doom scrolling on the feed. There's something about a book, which is it is a digested, synthesized piece of knowledge. Somebody's already done a lot of work to take all of this and dial it down. But then you're making that as a diversion point for yourself. You're limiting your input.

Srinivas Rao:

Yeah.

Daniel Stillman:

Sorry, go ahead.

Srinivas Rao:

Yeah. Limit your input, diversify whatever content you're consuming and you maximize your output. Yeah. Steven Kotler put it well in his last book, The Art Of Impossible, he ROI on a book is far greater than the ROI on reading some stupid article. And not only that, if you think about retention, I can tell you all sorts of stuff from every book I've read. So, let's say I've been creating content on the internet for 10 years. I can tell you 10 articles off the top of my head and what they're about. So, just think about the amount that I've been exposed to versus my actual references. You want to talk to me about books? We can talk about that until you're blue in the face. That I wouldn't give you endless amounts of...

Daniel Stillman:

I think this might be one of Tim's questions, but I love this question too. What's the book you gift the most? Are there some books that you think, oh my God, everyone should just read these three books.

Srinivas Rao:

Well, it's funny because the book that I gifted the most probably in the last year and a half was The Bullet Journal Method by Ryder Carroll. He did such an amazing job with that book. It's beautifully written. And once you start, it's funny, because every single person I've introduced the bullet journal to wonders how they ever lived without it.

Daniel Stillman:

I don't know if it was my dad who said this or it's just a famous saying, what the hand does the mind remembers.

Srinivas Rao:

Yeah.

Daniel Stillman:

When I was in grad school and I had to study for a test, I made a mind map because I'm a mind mapper. I would just get a big piece of paper out and I would just make a map.

Srinivas Rao:

Well, so here's the other part of that. One of the things that you'll notice, and I've been making a point to do this and honestly it's a pain in the ass and it's not something that everybody has the patience to do, but I've started printing out my blog posts and then going in and then looking at them and then rewriting each section by hand, after I write a first draft, because what you'll find is that because you can type so fast, you might say, okay, I wrote something in three or four sentences and then you can condense it into one and you start to become much more concise and economical with your use of language, because you're forced to.

Daniel Stillman:

Or because the handwriting shifts how you write out the sentences.

Srinivas Rao:

Yeah, absolutely.

Daniel Stillman:

That's so interesting.

Srinivas Rao:

It changes everything. And I have atrocious handwriting, so it's really frustrating, but it makes a world of difference and every single writer I know who is an amazing writer, Ryan Holiday, Dani Shapiro, Amber Rae, all of them, two things, they all read physical books and they write by hand. And I think there's something to be said for that.

Daniel Stillman:

So, the flip side to limiting your input, and this is something I noticed when I was looking at your second brain landing page, is it seems like reflection is an absolute necessity. It's not like Evernote where I just highlight and I clip and it's, quote unquote, "saved and searchable," it is on me to reflect.

Srinivas Rao:

Yeah. That's largely what this whole smart note idea is about, is to reflect on the ideas that you have been exposed to and elaborate on them. So, I just published this article titled The 21 Life Lessons From 2021, which is just 21 things my podcast guests taught me this year. Each one is basically an expansion of some idea that I learned when I interviewed one of my guests. And what does that force me to do?

Srinivas Rao:

It forces me to take one little quote from that interview and basically derive as much insight from that one little nugget as I can, because that's one thing, we don't do that, typically it's like we just have... This is of the things why I think people who think podcast transcripts are useful are idiots. Personally, what are you going to get from that? Because if you're scanning through a transcript, you don't have any context. So, it makes no sense, you don't even know what you're looking for.

Daniel Stillman:

You're saying it's useless for, useless for whom?

Srinivas Rao:

For a person who just wants to, for the most part, for a person who could listen, for somebody who's hearing impaired, that's fair. They can't hear. In my mind, those people are justified in wanting to read a transcript because they can't hear. But for most people, if you're somebody who has perfectly good hearing and you're just going to scan through a transcript, you're not going to really get the gist of what's going on there because you don't have the context, I don't see how that would lead to any insight that's actually useful.

Daniel Stillman:

Well, yeah. That's interesting because I use is the transcript for myself.

Srinivas Rao:

Yeah.

Daniel Stillman:

To redigest the interview.

Srinivas Rao:

Well, see, that's the difference, right? It's different because you did the interview.

Daniel Stillman:

I am different, it's true.

Srinivas Rao:

You know what to look for. Yeah. Well, trust me, I have all my transcripts inside of Mem now because I wanted to make sure that it would be easy to access them when I wrote this life lessons post. And the funny thing is putting together the basis of the article takes 10 minutes. It's really editing and arranging it and elaborating. That's where the real work happens, and that used to take me almost a month and a half. And now if I really wanted to, I could do it a day.

Daniel Stillman:

In what context do you feel like other folks who maybe aren't thought leadery, bloggy people, what is the average adult, the average thought worker, what does this look like for them? How do they judge success of this method, do you think?

Srinivas Rao:

Yeah. So, the average person, it's not like they have any shortage of information they're dealing with either, right? Making notes, projects they're working on all sorts of stuff to move things forward. And so I think it's just a matter of, okay, yeah, you're not a creative, but you're a knowledge worker who works at a company.

Daniel Stillman:

And then you are indeed a creative, yeah.

Srinivas Rao:

Well, you have tasks to manage, there are things that you need to get done. All of which kind of use the same principles. You're just changing the backdrop, but it's not as though the principles don't still apply.

Daniel Stillman:

Yes. And I feel like there was, somebody who I'm coaching took Tiago's goes course on this, I think you talk about this on your page as well. There's a difference between projects and tasks. And I think there's a third container.

Srinivas Rao:

So it's PARA basically, projects, areas, resources, and archives. So, areas are basically the things that are ongoing, so The Unmistakable Creative is not a project, it's an area because it's something I do daily, writing is an area. But if I'm writing a book, that's a project. So, a project is something by definition that has an end, a defined end date.

Daniel Stillman:

Yeah. So, everyone basically needs to be able to define for themselves what their elements of PARA are and then really control their input, be voracious and diverse, but controlled in terms of feeding those components of their PARA.

Srinivas Rao:

Yeah, exactly. So, you want to be deliberate about what you consume, not just sort of let me just... It's the sort of balancing act between being very deliberate, but also allowing your curiosity to guide you, but not in some different directions that you don't go, you go one mile in a thousand directions instead of a thousand in one.

Daniel Stillman:

You know, it's funny, the fear that's sparking in me, which I feel like would spark in everyone else is that this sounds like it takes time.

Srinivas Rao:

Of course it takes time.

Daniel Stillman:

Of course it does, it has value. And I feel like so many people...

Srinivas Rao:

What is worth doing that doesn't take time?

Daniel Stillman:

No, of course. I just feel like many people don't feel like they have control of their time.

Srinivas Rao:

I go back and forth on the time management complaint on the one hand I'm a single guy, I don't have kids who are screaming at me. And at the same time, these same people who bitch about all the things that are not enabling them to get the things they need to do done are also digging around on Facebook all day. So, you can't tell me, "I don't have time to do this thing because I have kids, but I can find an hour and a half a day to just doom scroll." It's like, all right, well then fine, yeah, your kids are a valid excuse, but you're lying to yourself when you... You're using them as a reasonable justification for not doing the thing you actually know you can do.

Srinivas Rao:

To me, when I hear this argument, I'm just like, none of you are are the President of the United States, none of you are Elon Musk. I promise you you're not as busy as you think. And I don't get that, in my mind, that argument is somewhat flawed that you don't have time. Everybody has 24 hours, find one. That's the other thing, you're right. This takes time. You're not going to get anything you want if you're not going to give something else up, in every area of your life, there's a trade off.

Daniel Stillman:

Yeah. Do you feel like an hour a day is a reasonable investment in building a second brain that creates a...

Srinivas Rao:

Yeah. Of course. I spend more time on all this stuff because it's my job, but yeah, an hour a day can potentially give you exponential results in comparison to the way that most people manage things now. I think that if you look, so typically one of the big causes of all these issues is perpetual mid task context shifts. I had to actually hop into my inboxes, I didn't have my link for my conversation with you, otherwise I would not have opened my email again until five o'clock. And again, I'm also a person who's ADD, so for me, this is 10 times worse than the average person. So, I have to go out of my way to do this. This is in a lot of ways out of necessity.

Daniel Stillman:

Yes. Perpetual mid task interruptions. I feel like that is just...

Srinivas Rao:

That's the kiss of death.

Daniel Stillman:

It's the kiss of death. Well, there's a term in Sanskrit, [Sanskrit 00:47:50], the disease of existence. And I think perpetual mid task disruptions is another version of the disease of modern existence.

Srinivas Rao:

Absolutely.

Daniel Stillman:

Which is why monotasking is so powerful and so important.

Srinivas Rao:

Well, and that's one of the things that's really nice about a tool like Mem and this whole idea of a sort of central storehouse without having to ever leave it is that you can work on different types of tasks all within one app and not have to go to 50 different sources to get this thing that you need. Don't get me wrong, there are times when I still have to get out of it. Okay, I'm not saying...

Srinivas Rao:

That is literally what I'm trying to get towards. The founders of Mem and I were talking, I was like, guys, this is what I want. I want to never leave Mem all day if I can. I was like, I'm serious, I literally don't want to think about ever having to open another app for anything that involves writing, creating. And honestly, if I looked at my actual time tracking, you would probably see that I spend probably 80% of my day inside of Mem.

Daniel Stillman:

Which is why, and for anybody who's listening, an inbox is not a to-do list, because there is constant influx of somebody saying, "Hey, Srini, can you do this for me?" And I just started using a CRM for my business development, and I can write emails in it. And it's actually, when you talk about mid task disruptions, the fact that I can just be in a place where no email is coming in, it's just about me being clear about who do I need to talk to?

Srinivas Rao:

Well, you know that all the emails you ever get from me, I don't write any of those, they're all automated scripts on the backend. For you to be a guest on our podcast, the only conversation I ever have, the first time I talk to you, anything I did, the only request I... Now you're reminding me, this is something else I need to add into the automation, I need you to send me the book, but I think that that's actually going to be something... I'm just going to put that on the bottom of the we'd be glad to have you as a guest email now. Because I literally have had publicists forget to send me the book and I'm like, look, I'm not going to do this unless you send me the book, that's the way this goes. And no author gets mad when that happens, but their publicists are idiots. And that pisses me off.

Daniel Stillman:

You want me to give you a free $3 book?

Srinivas Rao:

Yeah. It's like, yes, of course, because we're going to tell 1,000 people about it. And so that's the thing. So, a lot of this is, like I said, it's out of necessity, but yeah, we shouldn't be living in this world where... Cal Newport calls this a hyperactive hive mind workflow, this just ongoing unstructured, conversation about work without actually doing the work.

Daniel Stillman:

Yes. And this is about having a structured, consistent dialogue between the things you want to know and learn about and yourself, to make sure you're learning what you need to know. And then the output of that conversation, whatever it is, hopefully insights for you, an article for someone else, it might be a report. It might be the next conversation. Srinivas, I want to respect your time. We're getting up to time. This went really fast because there's clearly too much to cover.

Srinivas Rao:

Yeah. This is a tough one to articulate. Tiago does such a better job articulating this than I do because he's lived and breathed it. I think it's really difficult to articulate network thinking verbally. Because even when I had Sönke Ahrens as a guest, [inaudible 00:51:22] understand conceptually in terms of taking smart notes was kind of... I struggled because I saw the value because I've experienced it. And that's one thing that is kind of weird about this. So, tools like Mem have what a term that I coined called the utility paradox. I don't know that I coined that term. Maybe somebody else did. And what I mean by that is you can't quite understand why they're useful until you use them enough. So, Twitter is a great example of utility paradox, right? Twitter seemed like the dumbest thing in the world when people first discovered it, it was like, why the hell do I want to hear what people had for lunch?

Srinivas Rao:

And then eventually you start to see that, wow, this is actually cool. And people have used Twitter in the ways the founders probably never envisioned they would. Nobody thought people would be using Twitter to topple democracies or dictatorships, well, maybe that was a Freudian slip, maybe I've said that a few too many times because I live in the United States. I realize I have made that slip three times in multiple conversations and I'm like, oh my God, what have I been reading that is making me say that? But you could use Twitter to topple a democracy too unfortunately.

Daniel Stillman:

Yeah. Not for nothing, it almost happened.

Srinivas Rao:

Yeah.

Daniel Stillman:

Is there anything I haven't asked you that I should ask you? What haven't we talked about that we should talk about in our moments left together?

Srinivas Rao:

I don't know, I don't really know off the top of my head, I think we've covered a lot of interesting ground. I like the fact that this was kind of meandering.

Daniel Stillman:

Yes.

Srinivas Rao:

It was very nice.

Daniel Stillman:

Well, I have resisted the structure that goes into building a second brain, but looking at your page about it, I'm actually really excited to get started. If people want to find you on the interwebs, is there any place particular they should go besides...

Srinivas Rao:

So, Unmistakable Creative is a podcast and then maximizeyouroutput.com is where you can find all my knowledge management work. I also have a YouTube channel for Mem if you just go to, I think it's called The Creative Life or something like that. I don't know what the name is. It's funny because I focus on the videos, I haven't even bothered with the rest of it. I don't spend much time thinking about the semantics other than the content.

Daniel Stillman:

But the course is out there, it's live, people can...

Srinivas Rao:

Yeah. The course is available. People can buy it, [inaudible 00:53:49], it's there.

Daniel Stillman:

Yeah. I'm excited. Mem sounds like a really interesting tool. It sounds like it's an investment to get it, as you said, jump started.

Srinivas Rao:

Yeah, it is, so that's the thing, part of the thing that's challenging is it's very counterintuitive because it goes against the linear way that you're used to organizing things.

Daniel Stillman:

Yeah. Well, I'm grateful for the time, Srinivas, and my mind is expanded and I think it's something everyone needs to be able to manage the flow of input, insight, and output. And I think it's really, really key and crucial.

Srinivas Rao:

Yeah, absolutely.

Daniel Stillman:

Well then I'll call scene.

The Power of Wondering and Wandering

This episode, Dr. Natalie Nixon and I dig into not just what it means to be creative, but also how leaders can create space for creativity and inspire it in their teams by letting in a little chaos.

Dr. Nixon is the author of The Creativity Leap, a creativity strategist, and a highly sought-after keynote speaker. In this conversation, we dive into the ideas behind her book, what makes someone "a creative" (hint: it involves being deeply human), and how important humanity and creativity are to the future of work - Natalie and I agree that we should let our AI overlords do what they do best…and we humans should focus on what we do best - be creative and empathetic!

Natalie and I have three unexpected things in common: Ballroom dancing, an enthusiasm for Chaordic Thinking, and a deep sense that these two things are deeply intertwined!

Dancing looks to regularly resolve the dynamic tension between chaos and order, and find a state of flow between the two.

Chaordic Systems Thinking, if you’re new to it, was first coined by Dee Hock, the founder and former CEO of VISA. He felt an ideal organization would balance order and control with disorder and openness, moving between them as it grew. Chaordic is just a made-up word combining chaos and order. I made a basic diagram of Chaordic systems Thinking for my book, Good Talk.

Total Order (O, on the right) is oppressive and stultifying. It also doesn’t deal well with surprise or adapt to unpredictability. Total chaos (C, on the left) can mean a total collapse of a given system - as Natalie says, without any boundaries, what is it even!?! 

A chaordic system moves between the poles of chaos and order, spiraling outward, growing and expanding as it does. A conversation can be chaordic, too, by the way.

For example, in a workshop, I sometimes feel the noise of collaboration and conversation rise, and I wonder, “Is this the moment to rein things in and move the conversation forward?” After all, sometimes that golden “aha” moment is just around the corner, just past my capacity to enjoy the chaos.

In the chaos and randomness, new patterns are sometimes found. Like in jazz, those new patterns are then played with, firmed up, made more orderly…until they get too controlled, boring or repetitive. Then the chaordic cycle swings back towards chaos. 

This is why, as Natalie points out, good leaders are also good followers: they are open to changing environments, and take the best of what’s emerging, reading their team and adapting to new situations.

Natalie and I also unpack the misunderstandings many folks, leaders included, have around the idea of being creative - one of most damaging being that the word doesn't (or can't) apply to them.

Natalie's ideas on creativity and flow are critical for the future of work, and something that every leader, whether you lead a team of artists or a team of accountants, needs to hear.

Enjoy the conversation!

Links, Quotes, Notes, and Resources

figure8thinking.com

The Creativity Leap by Natalie Nixon

Your "invisible work" is key to your most productive self by Natalie Nixon

The Extended Mind by Annie Murphy Paul

There is Confusion by Jessie Redmon Fauset

How to Get Filthy Rich in Rising Asia by Mohsin Hamid

Bright Lights, Big City by Jay McInerney

Sand Talk by Tyson Yunkaporta

Sand Talk: How Indigenous Thinking Can Save the World, interview with Tyson Yunkaporta

Minute 1

Natalie Nixon: And when I talk about leading with questions, leading with inquiry, what it doesn't look like, is to invite your teams, people who you're working with. Come on guys, ask me your best questions. I'm open to your questions because people have been through a lot of question shaming, either through their educational learning experiences, through work. And so they might be a little gun shy for that. It starts actually with leaders being a bit more transparent about the questions that they have.

Minute 7

Natalie Nixon: because the gift that keeps on giving in terms of life lessons is that the best leaders are actually really good followers. Really good leaders are following in the sense that they are trying to align with. They're trying to adapt to the teams, the markets, the customer. They're listening actively. They're really observing. They're not barreling ahead. It absolutely can play out on the individual team and larger scale levels.

Minute 13

Natalie Nixon: But chaos is not anarchy, chaos is randomness. And order is not control, order is a structure, it's boundaries. The cool thing about chaordic systems, and Chaordic Systems Thinking is what a bunch of academics later called it.

And there's a whole group of scholars who have Chaordic Systems Thinking conferences and all that sort of thing. But once you start learning about chaordic systems, you literally cannot stop seeing them. Everything in the world and nature and our bodies is based on this beautiful ebb and flow between chaos and order. I wrote this down, what you just said, Daniel, polarity management and paradox thinking, it makes complete sense to me because it's another way of talking about chaordicness and chaordic systems. Clearly, I was deeply influenced by that way of thinking and I landed on this definition of creativity being toggling between wonder and rigor to solve problems. In all complex systems, all improvisation requires that ebb and flow between chaos and order. Chaos is the wonder part or wonder is the chaos part and rigor is the order part.

Minute 25

Natalie Nixon: To make room for creativity in our organizations, it's going to require a bit of an upheaval and overhaul in the way we are educating and the way we're invited to learn.

Minute 27

Daniel Stillman: How do you feel like you'd like leaders and teams and organizations to be investing in the creativity of their whole company?

Natalie Nixon: It's so interesting you're asking me this question. Before we started speaking, I just got off of call with a client who's asking me that as a starting place. And the question was, how do we begin to design in more space and time for creativity, so that we could build our creative capacity. And I looked at him and I was like, "We decide to build in more space and time for creativity on that space and continuum." How do you become a better writer? You got to write.

Minute 32

Natalie Nixon: What is something that can start happening weekly or monthly or quarterly that begins to tweak the way people are showing up? And it's important. Remember that starting to make creativity core to the capacity of an organization will not happen overnight. Culture change starts with shifts in our mental models, which leads to shifts in our behaviors, which finally leads to changes in culture.

Minute 36

Natalie Nixon: And what I'm really asking is, what if we start to devise, define, dream up new metrics of productivity. I wrote about how in the industrial age, productivity was measured based on output of widgets. In the information age, it's been about time on task. In this Fourth Industrial Revolution where we're going to have robots and AI mastering the task, what I'm observing is that if you followed the Pareto rule, the 80/20 rule, 80% of our most productive work, I don't know about you Daniel, but it's happening when I am letting myself walk away from the laptop, my desk, taking a walk, reframing a question in my head, wondering, sitting with my intuition, it's all those things that help me to, they're creating the scaffolding for the most productive work.

Which then pushes out and synthesizes in that last 20% time. And I know that's a very scary way to think about productivity when we think about this current way of metrics, metrics, metrics. But what if we shift the metrics? And what if we see a bit more control as manager. This way of thinking about productivity requires a lot more trust.

Minute 43

Natalie Nixon: Just what I want people to leave with is, they have the agency and the ability to build a creative capacity and it takes some rigor. It takes some work. It's not always sexy. It's often very solitary. That's the rigor part. But I have this corollary expression, that I think it's in the book and I have this postcard about it, which is that, wonder is found in the midst of rigor and rigor cannot be sustained with that wonder. So when I say that wonder is found in the midst of rigor, it's in the midst of doing the fundamentals, getting the mastery of skill, the solitary stuff. It's in those moments that an aha moment emerge. That's the wonder. And when I say that rigor cannot be sustained with that wonder, we will burn out if we don't integrate moments and time for the dreaming to ask new and different questions. Both are true and we have the capacity to do that. And it starts with oxygenating our ideas. Giving them light, giving them air, sharing them out.

More About Natalie

Creativity strategist Natalie Nixon is “the creativity whisperer for the C-Suite”. She is a highly sought after keynote speaker, valued for her accessible expertise on creativity, the future of work and innovation.

Natalie advises leaders on transformation- by applying wonder and rigor to amplify growth and business value. She brings an innovative and unique perspective to every keynote, strategic advisory engagement, and leadership coaching session. Her experience living in 5 countries combined with her background in anthropology, fashion, academia, and dance distinguish her as a one-of-a-kind creativity expert.

Natalie has been named among the top women keynote speakers by Real Leaders and BigSpeak; and has been featured in Forbes, Fast Company and INC. She’s the author of the award-winning The Creativity Leap: Unleash Curiosity, Improvisation and Intuition at Work and her firm Figure 8 Thinking, was named among the top women-led innovation firms by Core 77. Marketing guru Seth Godin has said that Natalie “helps you get unstuck and unlock the work you were born to do!”; and Jessi Hempel, host of LinkedIn’s “Hello Monday” podcast called Natalie “a personal trainer for your creativity muscle”.

Natalie received her BA (honors) from Vassar College, and her PhD from the University of Westminster in London. Follow her @natwnixon.

Full Transcript

Daniel Stillman: I'm going to officially welcome you to the Conversation Factory. Natalie Nixon, welcome aboard. Oh, it's all right.

Natalie Nixon:   Thank you, Daniel.

Daniel Stillman: We can just talk over each other the whole time, see if we can keep that going.

Natalie Nixon:   We could do. Thank you, Daniel. Good to be here.

Daniel Stillman: Thank you. And thanks for making the time. Listen, where shall we begin? Actually, I'm wondering, what question you would wish. I was watching a video of yours about problem framing and how often we're solving the wrong challenges. I'm sure you've discovered that's happened from time to time in your work. What question do you wish leaders would ask of themselves more often?

Natalie Nixon:   First of all, I love that you started with, I wonder. Your question to me, very meta, because I think literally, there's nothing bad that follows the utterance, I wonder. Actually, it is that level of self inquiry that I actually don't know that leaders do often enough or if they do, they don't share out more transparently their self inquiry. And when I talk about leading with questions, leading with inquiry, what it doesn't look like, is to invite your teams, people who you're working with. Come on guys, ask me your best questions. I'm open to your questions because people have been through a lot of question shaming, either through their educational learning experiences, through work. And so they might be a little gun shy for that. It starts actually with leaders being a bit more transparent about the questions that they have. It's very situational. It requires context. But good questions for leaders to ask are, I wonder if this tack still makes sense. And speaking of this tack, I mean, that story out of, I actually never sailed before my life. It's one of my [inaudible 00:02:14]. Tacking is a part of sailing.

Daniel Stillman: Yeah, it is.

Natalie Nixon:   When we never go about sailing and like, this is the course we set. We got to keep going in though. All the alarm bells are going off, clouds are rolling in, thunders rumbling. The waves are getting rockier and rockier. You tack and shift and adapt your course accordingly. Even starting with that question to oneself of, I wonder if this approach still makes sense, and sharing that question that you've had, couple your thoughts with asking teams their thoughts as well, is really important.

Daniel Stillman: It's so interesting. The idea that leaders should be more self-reflective and sharing the questions that they're sitting with, with their teams, is a really interesting one. And I'm wondering, the first thing that comes up to my mind is the resistance some people might have to that. It's like, "Oh, well, I need to show ...

Natalie Nixon:   Certainty.

Daniel Stillman: Certainty, and strength and ...

Natalie Nixon:   Clarity.

Daniel Stillman: Clarity. But on the other hand, what are the pluses and the what's the what's the cost and the benefit do you think to that strategy?

Natalie Nixon:   Yeah. On the other hand, who really knows what's going on? One of the slides I like to show in some of my keynotes is a slide that says, plans are fiction. And I love that statement because plans are fiction. And they're fiction because they haven't happened yet.

Daniel Stillman: Wait, wait, wait. You are a professor of strategic design.

Natalie Nixon:   Yes. It doesn't mean that you don't start with a plan. I love my to-do list.

Daniel Stillman: Yes.

Natalie Nixon:   Every single morning, I start with that to-do list. But because I understand that plans are fiction, I can approach it more comfortably, in a much more adaptive way. There's a wonderful artist named Avery Williamson. She has a great Instagram channel. She posted something recently where she ... Her Instagram by the way is aisforavery, you must follow her. She's got outstanding visual art. But one of the things she posted recently was her rules for her studio and said something like, create your to-do list, cut that in half and then cut it off again. Just to be just to be adaptive and actually a bit more focused. That idea of leading with certainty is something that every MBA program worth its salt tries to instill. And yet, once we graduate people out into the ambiguous world of business and commerce and markets, we realize that you've got to be super adaptive. One of the reasons why I love behavioral economics, which didn't really take off until the early eighties is because it reconciled that markets are made up of people.

Daniel Stillman: Yes.

Natalie Nixon:   And therefore markets are imperfect, inconsistent and not predictive, which was a total departure from the way economics had been thought about and taught, which was, and this is something in my previous life, I used to have to read through those academicy journals and older business marketing and finance journal article, scholarly articles to start with hypotheses. They try to be very scientific in their approach. But now we understand that we've got to be a lot more adaptive. And so leaders have to be much more adaptive. And actually, that level of transparency is absolutely terrifying, as a leader. And it opens the door for trust. It opens the door for communication so that you can actually lead in a much more effective way.

Daniel Stillman: It's really interesting. I'm wondering if we can apply this thinking. One of the hypotheses that I've been having about communication and conversations is they exist on these different levels. There's the conversations we have with ourselves, there's team conversations. In an organization, it's just the marketplace of conversations, with loads of conversations. I'm wondering if you feel like that reflective questioning is something that you'd like to see happening at all of those scales in an organization, at the leader level, maybe even at the individual practitioner level, at the team. What does that look like, do you think?

Natalie Nixon:   Well, I shared a post a month or so ago on LinkedIn that got a lot of engagement and I was happy to see it. I actually shared a bit more of a personal part of my life. I shared how I'm a lifelong dancer and I study ballroom dance.

Daniel Stillman: I saw that. I want to talk about dancing with you. But yes, please proceed.

Natalie Nixon:   I was going to kind of go there at this point because, you are right, there's opportunities to be much more transparent, self reflective on the individual team, society level, we can scale it on those three ways. Because one of the things I've learned from ballroom dance, as a student of ballroom dance, because the gift that keeps on giving in terms of life lessons is that the best leaders are actually really good followers. Really good leaders are following in the sense that they are trying to align with. They're trying to adapt to the teams, the markets, the customer. They're listening actively. They're really observing. They're not barreling ahead. It absolutely can play out on the individual team and larger scale levels.

Daniel Stillman: Let's talk about ballroom dancing for a second, because this is important. On Facebook somebody posted, it was a high school gym elective. It was the most popular, I don't know if this is the most popular. It was coveted by some nerds, gym elective in my high school. And so I took ballroom dancing and it wasn't many, many years later that I started swing dancing. Swing is my happy place.

Natalie Nixon:   Nice.

Daniel Stillman: And I think one of the hardest things for people to understand, who are new to this is, is the dynamic tension.

Natalie Nixon:   Yes.

Daniel Stillman: The push and pull. For those of you who are listening at home, Natalie and I are sort of putting our hands together and tugging because there's this feeling, it's like chewy. It's just like it's a very great feeling when at the end of a twirl or there's not a saggy arm. There's tension.

Natalie Nixon:   No. It's not a hard rigid arm.

Daniel Stillman: No.

Natalie Nixon:   It's not a saggy arm, but there is that slide you're there, I feel you, I'm with you, I'm responding to you so that I know what to do next. So that if I'm the leader, I have the confidence that you're going to have clarity about what I'm asking you to do next. If I'm the follower, there's going to be a clear transmission of the direction you want me to go there. There's intuiting at every single moment, but it requires that contact.

Daniel Stillman: Contact, yes.

Natalie Nixon:   It requires that contact, that communication.

Daniel Stillman: And sometimes I think my wife will interpret my signal differently. And she'll be like, "Oh, sorry." And I'm like, "No, that's okay. That's a great idea. Let's go with that."

Natalie Nixon:   We have to go with it.

Daniel Stillman: So this is the thing that I was thinking about. Wonder and rigor as these two poles that you talk about in The Creativity Leap, your book, that's behind you on the shelf. I've been doing a little bit of reading on this idea of paradox thinking and polarity management. And this is not my research. There's tons of research out there. I feel like I want to just zoom in on that set point. If wonder and rigor are on a little infinity loop and we're not supposed to just go all the way onto wonder and all the way onto rigor. We want that dynamic tension right in the middle. What's there at that beautiful set point?

Natalie Nixon:   I believe what's there at that beautiful set point is flow. One of the biggest things that I think people misunderstand about creativity is that, when people think that creativity is woo-woo and that it's only about doing whatever you feel like, which couldn't be further from the truth. That wonderful polarity that you're talking about, I really became equipped with the language of how to think about those dualities, that very dynamic ebb and flow, tension, however you want to call it when I learned about Chaordic Systems Thinking. And I learned about Chaordic Systems Thinking when I naively decided to earn a PhD while working full time, because I thought I was just a big old paper. How hard could that be?

Daniel Stillman: Classic blunder, like a land war in Sicily and whatever else discussed in the Princess Bride.

Natalie Nixon:   Exactly.

Daniel Stillman: For those of us who are listening in the audience, I have a little snippet about chaordic thinking in my book, but do you want to talk about Dee Hock's chaos order hypothesis on a sticky note?

Natalie Nixon:   Yeah. That's when I was introduced to Mr. Dee Hock who was the first president of Visa, the credit card company, most of us have a credit card.

Daniel Stillman: Perhaps you've heard of it, everyone.

Natalie Nixon:   You've heard of Visa. And to his credit, when he was asked to lead this global organization, based on the virtual exchange of currency in the early sixties, late fifties, he was a big naturalist. He's taken a walk through the woods, lots of walks through the woods. And he thought, what if I could lead and organize this company in the ways that I see nature behaving? Where there's some chaos and there's some order. And what Dee Hock was identifying. And these are my words, not his, he was identifying that organizations are organisms. Because they're made of humans because they're made of people. He did a mashup of those two words, chaos in order. And he made up the word chaord. And he has a great book, by the way, it's really a memoir called One from Many, if anyone is interested in reading more on Dee Hock's work. But chaos is not anarchy, chaos is randomness. And order is not control, order is a structure, it's boundaries. The cool thing about chaordic systems, and Chaordic Systems Thinking is what a bunch of academics later called it.

             And there's a whole group of scholars who have Chaordic Systems Thinking conferences and all that sort of thing. But once you start learning about chaordic systems, you literally cannot stop seeing them. Everything in the world and nature and our bodies is based on this beautiful ebb and flow between chaos and order. I wrote this down, what you just said, Daniel, polarity management and paradox thinking, it makes complete sense to me because it's another way of talking about chaordicness and chaordic systems. Clearly, I was deeply influenced by that way of thinking and I landed on this definition of creativity being toggling between wonder and rigor to solve problems. In all complex systems, all improvisation requires that ebb and flow between chaos and order. Chaos is the wonder part or wonder is the chaos part and rigor is the order part.

Daniel Stillman: You used the word toggle. Do you think a switch or is it an equalizer? Are you moving it again? What is the knob you're spinning when you're doing that?

Natalie Nixon:   Well, we rarely listen to AM/FM Radio anymore.

Daniel Stillman: I know.

Natalie Nixon:   But if any of your OGs out there-

Daniel Stillman: I am an OG. We didn't even have the search function on my first radio. We had those push buttons you could program the five stations.

Natalie Nixon:   The five stations and there's a round knob and you hear the static and you got ... Exactly. You start to hear the clarity. And actually, we started our conversation talking references to sailing. I suspect when sailors are out in the middle of nowhere, they're trying to get a signal, it's similar. It's like getting to that signal and doing these small, it's tweaking. That's what I mean by the toggling.

Daniel Stillman: Yeah. It's so interesting. I'm wondering, I'm wondering, there it goes. You just put it in my brain.

Natalie Nixon:   There you go.

Daniel Stillman: You've incepted it in us. Maybe we should take a step back for those of you who are listening who haven't read Natalie's book. It's behind her. You can't see it because you're listening to this. What made you decide to write this book? This idea is so important. I'm going to write a whole furshlugginer that's Yiddish for this pile o' book. You're going to do take all these ideas and just boil it down into this slim volume. What was that journey like for you?

Natalie Nixon:   Well, most things I set out to do in my life, I was very naive about what would be involved. It all starts from passion. It all starts from deep curiosity on my part. What had happened was ...

Daniel Stillman: That is the best beginning of ... I feel like that's a meme, isn't it? So what had happened was ...

Natalie Nixon:   What had happened was, I used to be a professor. I give this talk in 2014 at TEDxPhiladelphia about the future of work is jazz. And here's why and how. After I gave that talk, I get invited into companies to help them figure out how to be more adaptive and improvisational in the way they're designing their own work. And I'm getting so many of these invitations. My husband John, correctly said to me, he's like, "Babe, this is a thing. You should formalize it." I was like, okay. I created Figure 8 Thinking as my side hustle.

             And then I woke up a year later and realized, "Oh my gosh, I'm having more fun with my side hustle." And this is really the cliff notes version. There's a lot more that was evolved in this process. But basically, I decided to leave academia. After 16 years as a professor, I move on and full time, I'm a creativity strategist leading and building Figure 8 Thinking. First couple of years of work at Figure 8 Thinking, a lot of the projects I was getting invited to do were to help these organizations build cultures of innovation. It was all about the, I word.

Daniel Stillman: She's raising her hands up in a rah-rah symbol.

Natalie Nixon:   Yes.

Daniel Stillman: What year was this around?

Natalie Nixon:   This is like 2017, 2016, 17.

Daniel Stillman: Yeah. I mean, it's still a thing. It was definitely a thing then. We all need to be innovative, rah-rah, and let's get everyone rah-ing about it.

Natalie Nixon:   Rah-ing about it. Sometimes that we were talking over and around each other, we were missing each other. What does innovation really mean? What does it mean to us specifically as an organization? And it also would sometimes end up in what a lot of us, who work in this space called innovation theater.

Daniel Stillman: Yes.

Natalie Nixon:   Which is not very sustainable.

Daniel Stillman: Or impactful.

Natalie Nixon:   Or natural. That got me to thinking, and it was really the sense, I was like, "I don't think we're going about this the right way of just landing, we got to innovate." And I started thinking, I knew enough to know, one cannot critique a system without offering up an alternative way to go about doing the work. I was like, "I can't critique some of my clients to start innovation if I can't give them an alternative way of where they might start.

Daniel Stillman: Yes.

Natalie Nixon:   And I thought, I think we should be starting with creativity now. Now here's the challenge, in the how old halls of Corporate America, if you utter the word creativity, people look at you like you've three heads. Creativity is not murmured in the corporate boardroom.

Daniel Stillman: Yes.

Natalie Nixon:   If it is mentioned, it's kind of an afterthought, it's country, like lipstick on a pig.

Daniel Stillman: And it's something that somebody else does. They're like, "Well, I'm not a creative like you all."

Natalie Nixon:   I'm not a creative like you all over there.

Daniel Stillman: Yeah. I mean, you can't see Natalie's glasses, she's clearly creative.

Natalie Nixon:   Exactly. You're right. These very kind of simplistic ways of thinking about creativity.

Daniel Stillman: But they limit people. You walk around with the whole, easily more than half of a company thinking, "I can't access that part of myself."

Natalie Nixon:   No agency. We've cut off agency that's embedded, in my view, in all of us. All of us are hardwired to be creative. That led me down this path of, how can I offer an accessible, simple way for people to think about creativity? And I use my keynotes speaking as a way to prototype ideas. Every time I give keynotes talk I'm landing with what my client, what they need, but I'm also trying to play with new concepts, new ways of framing things. And consistently, people who enjoyed my keynotes would come up to me and say, "That was awesome. Where can I read more about this?" I was getting enough of those questions to realize, I got to put all these ideas in a consolidated fashion, into a book. At the time, I was writing for Inc. Online. And I could send them that but they were kind of one off articles.

Daniel Stillman: Yes.

Natalie Nixon:   So the real impetus for writing the book was what I was hearing from clients. This need that I identified as this need to really be able to explain very tactically, how people could really apply creativity in order to innovate.

Daniel Stillman: Yes. Because they need to. And I guess now's a good time to maybe transition into this idea of the Fourth Industrial Revolution. Anything that can be put into a spreadsheet, eventually an AI or some sort of mechanistic approach can do it better than us. The only things that are left to humans in the future is being human. Being creative is something that only we uniquely can do.

Natalie Nixon:   It's interesting because the engineers and scientists who are playing around with AI, which we've thought of as artificial intelligence have also been playing around with dividend of AI, which they artificial imagination. They actually have been tiptoeing into this realm of how might machines be programmed for that randomness, that randomization. The thing about imagination is that imagination is so multidimensional. It's catalyzed by our past and in many other ways, it's contextualized in the present and what we are seeing around us. And then it's all about our ability to dream. And how one programs that into machine learning, I'm not really sure because I'm not an engineer. Who by the way, are incredibly creative in the ways that they are designing.

Daniel Stillman: Most definitely.

Natalie Nixon:   The sort of AI. But you're absolutely right, in this Fourth Industrial Revolution where tech is ubiquitous, because tasks are going to be taken over, the opportunity is for organizations, companies, associations, to figure out ways to invite our humanness to show up. Our humanity to show up. What only we as people can do. And whoever figures that out on consistent basis, those are the companies that are going to flourish and thrive. Because they're going to be able to attract and retain the best talent. People have been dying a slow death of only being asked to fill in the dots. I mean, we go back to our educational systems.

Daniel Stillman: Sure.

Natalie Nixon:   Where we have a two track system. I came up through the two tracks. I started out in urban public school in Philadelphia, where very clearly, I didn't realize until I was out of that system, we were being educated to fill the dot. To complete the worksheet, to stay in your lane. And then later in high school, I went to an elitist Quaker prep school in Philadelphia from seventh through 12th grade. And it was a culture shock for me on several levels. The main levels was the culture of learning. I was being invited to beg forgiveness, not permission. I was invited to be loud and wrong. I was invited to ask a better frigging question, which was counter. I had gotten so good. I showed up an A student in seventh grade because I gotten so good at knowing what the teacher wanted and really delivering what the teacher wanted.

Daniel Stillman: Playing the system.

Natalie Nixon:   Playing the system. And then all of a sudden, it was a different system. It was about, we don't know. Maybe the questions we've asked weren't quite the right questions. And so it took me two years to really understand that. And then it was around eighth, ninth grade, I thought, "Oh my goodness, my friends back on the block, my friends who are in public school." We were being trained to fill in the dots. And now I'm around people who are being educated to figure out the dots to figure out the lanes. I didn't have that language back then, but I remember the shift in me when I thought, it was like this, you had peeked under the kimono. And I was like, "Oh my God. This is what's happening."

Daniel Stillman: Sure.

Natalie Nixon:   To make room for creativity in our organizations, it's going to require a bit of an upheaval and overhaul in the way we are educating and the way we're invited to learn. Which by the way Daniel, have you noticed how many companies now are in the business of learning? Everyone from Lincoln, the Fast Company, let alone MasterClass, which now has Outlier and Coursera. And it's about learning on people's own time, on their terms, highly produced, high entertainment value from people of street credit. It's just a very interesting shift about how we're even starting to see how we're delivering learning very differently.

Daniel Stillman: I have to say though, I find that people are crunched hard. And their ability to take time out, to even watch a 10 or 15 minute video between one session and another session two weeks later, is limited. Because there's a culture of, we got to do it all. We got to keep going. And I guess what I'm wondering is, I feel like I've used wonder more in this conversation than I have in the others. So thank you Natalie.

Natalie Nixon:   I guess you're more aware of it probably.

Daniel Stillman: Yeah. It's probably true. Dr. Nixon is good at incepting wonder in people. And going back to my first question of what should we be asking ourselves. Back in 2017, my hypothesis about where companies should be spending their, we want to have a culture of innovation dollars was, if I'd known you, I would've said, "Go hire Natalie Nixon to be a speaker and hire me to train everybody on design thinking tools." And I don't know what would create lasting impact and real needle moving today, in today's culture. I would say still call Natalie and hire them to speak to your people. I wouldn't say train everyone on these tools because it's different for everyone. What would will create in their context an ability to be more creative? How do you feel like you'd like leaders and teams and organizations to be investing in the creativity of their whole company?

Natalie Nixon:   It's so interesting you're asking me this question. Before we started speaking, I just got off of call with a client who's asking me that as a starting place. And the question was, how do we begin to design in more space and time for creativity, so that we could build our creative capacity. And I looked at him and I was like, "We decide to build in more space and time for creativity on that space and continuum." How do you become a better writer? You got to write.

Daniel Stillman: Yes.

Natalie Nixon:   You got to read a lot. How do you build your capacity of creativity? You have to decide to design in the time and space for creativity, which look like the-

Daniel Stillman: Intentional practice.

Natalie Nixon:   Number one, I love etymology. I love understanding, what's the root meaning of these words and how they come to be. And the word decide is so beautiful to me because embedded in decide is caesa, which is cut, scissor. When one really makes a decision. You are cutting off what was, and you are embracing and going for it with the new. When you make a decision, it is a cut off from what you used to do. First, the organization has to decide, this is what we want to do. And then doing it does not have to be these radical revolutionary changes. In fact, the best revolutions have been through these small cracks and fissures in the system. It's by doing these small tweaks. You start to change the way you begin and start meetings.

             You don't radically change. We're not going to have XYZ meetings anymore because that would be too much change. Because everyone is already going through change fatigue. But the way we're going to begin and end the meeting is going to shift in this way. The way we're going to start to introduce inquiry and questions could be having quarterly meetings that are just focused on questions that we're collecting from the group, or it could be meetings that we're just focused on generating questions. I mean, your mind can just go wild once you're given the permission to think through what's something that we're going to change that's small, that's tiny, that we're going to tweak. Every organization has a culture, which means that every organization has the icons of culture, which are language artifact, ritual, symbol. We can start with just those four things.

             You can start right there and identify, in each of those categories, which are icons of our culture. What are we going to start to tweak? And I'm going back, I now realized it's funny in this conversation too, the way I learned in my educational history. I just shared earlier, I went to a Quaker prep school in Philadelphia for high school. Philly has a lot of Quaker prep schools. It just the history of Philadelphia.

Daniel Stillman: Yes.

Natalie Nixon:   But you had to go to something called meeting for worship every week.

Daniel Stillman: Yes.

Natalie Nixon:   Whether you were in kindergarten, first grader or an 11th grader. And what that involved was, going into this very plain simple meeting house, just creaky old wooden benches with saggy cushions along the benches. And you sat in silence for the equivalent periods, like 40 minutes.

             And what's fascinating is that to an alum. When you were in high school, you slept through it. You hate it. You're so bored or you would just be ruminating over a test it was going to be later that afternoon, whatever it was. Everyone misses that into adulthood. You miss that space and time that was dedicated to instigating, instituting that icon of Quaker culture. What does that look in your organization? What is something that can start happening weekly or monthly or quarterly that begins to tweak the way people are showing up? And it's important. Remember that starting to make creativity core to the capacity of an organization will not happen overnight. Culture change starts with shifts in our mental models, which leads to shifts in our behaviors, which finally leads to changes in culture.

Daniel Stillman: What is so beautiful about that—So, many people do not know about Quaker meeting.

Natalie Nixon:   That's true.

Daniel Stillman: And I have been to some Quaker meetings and I talk about Quaker meetings when I talk about turn taking in meetings often with people. The idea that, usually what happens in a meeting is one person tends to speak first. And that sets the terms of the debate for everyone else versus having a round Robin where everyone sort of speaks in turn. Versus in a Quaker meeting, it's not a popcorn meeting where everyone pops and you want all the kernels to pop. A Quaker meeting, for my understanding is you only speak when the spirit of God speaks through you.

Natalie Nixon:   Correct.

Daniel Stillman: Literally inspiration or aspiration in this case. The idea of having more Quaker meetings in a business context has always thrilled me.

Natalie Nixon:   It's thrilling. And it also could be painstaking because Quakers also believe in consensus, which can be mad if you're trying to come to a decision, because they really hold fast to consensus.

Daniel Stillman: Yes.

Natalie Nixon:   And actively listening to your point of view and then rehashing it and listening again, and then reconsidering. Consensus is serious for Quakers.

Daniel Stillman: Yes.

Natalie Nixon:   By the way, there are such things in Quakers, it called popcorn meetings, it's a meeting that there's a lot of people.

Daniel Stillman: Yes.

Natalie Nixon:   That's Quaker humor, I guess. The Quakers believe that the light of God shines in each of us. When you feel stirred or they would say quake, that's where they got the name Quaker, one was moved to stand up and speak what was on one's heart.

Daniel Stillman: Yes.

Natalie Nixon:   And sometimes what follows is another point related to that. Other times it's a different point. But that idea of making time to pause for silence, to try to commune to hold the space of another person's thought or energy and let it sit with it and maybe you let it go or maybe you don't. It was phenomenal. It was something that I found that I really would crave at different moments of my life thereafter.

Daniel Stillman: Because our time together is growing nigh. We need to talk about Invisible Work. For a culture that values doing and producing over being and existing and non-production. Dreaming, daydreaming wondering can look lazy. In fact, there's an old joke about this. That when you walk by a mathematician's desk and they've got their feet up and their eyes closed, they're hard at work. Because they're still thinking about math.

Natalie Nixon:   I don't know that. I love that. That's good. I like that.

Daniel Stillman: It's not much of a job, but fair enough.

Natalie Nixon:   I like that. I wrote this article for Fast Company about something I call invisible work. And again, all of my work typically starts with this nudge inside of me, which turns into a provocation, an offering of how I'm inviting people to think through something in maybe a new way, maybe a different way. And what I'm really asking is, what if we start to devise, define, dream up new metrics of productivity. I wrote about how in the industrial age, productivity was measured based on output of widgets. In the information age, it's been about time on task. In this Fourth Industrial Revolution where we're going to have robots and AI mastering the task, what I'm observing is that if you followed the Pareto rule, the 80/20 rule, 80% of our most productive work, I don't know about you Daniel, but it's happening when I am letting myself walk away from the laptop, my desk, taking a walk, reframing a question in my head, wondering, sitting with my intuition, it's all those things that help me to, they're creating the scaffolding for the most productive work.

             Which then pushes out and synthesizes in that last 20% time. And I know that's a very scary way to think about productivity when we think about this current way of metrics, metrics, metrics. But what if we shift the metrics? And what if we see a bit more control as manager. This way of thinking about productivity requires a lot more trust.

Daniel Stillman: Yes.

Natalie Nixon:   I reference a book I used ... When I was a professor and I taught for the first 10 years, I taught the business of fashion and I used to teach a course about apparel sourcing. Apparel sourcing is a lot more interesting to do, than it is to learn and teach. And I was like, "Oh my God, how I'm I going to make this exciting and interesting for these young people." And I found a book, it's a memoir by the founder of Patagonia called Let My People Go Surfing. And it literally is a handbook for sourcing. It's a handbook for sourcing disguised embedded in this memoir. Each chapter is taking you through vendor relationships, through sourcing a fiber and all that thing. And one of the things he shared is that, he had this macro management philosophy that, if members of his team were into surfing and they knew the surf was going to be up between 2:00 and 4:00 later today, they're out of there. They're in the ocean. They're playing in the waves.

Daniel Stillman: Yes.

Natalie Nixon:   And he was okay with that because he had the trust that they go have dinner with the fam and they would come back and grind out the work that needed to be done later that evening, if that met their fancy. And I've never forgotten that because it was so, in my view, Liberal and liberating.

Daniel Stillman: Yes.

Natalie Nixon:   And really ahead of its time. That's the type of invisible work. That allowing people to play, to really be embodied in their work is this other dimension of invisible work. When we believe that work is only when we're at the whiteboard, on the Zoom call, we are only showing up to work from the head up. From the heart up, never from the gut up. And the opportunity now is to show up to work from the gut up, which requires different type of management, different type of leadership. And actually, in this hybrid office setup that we have now, there's more opportunity to allow people to go ahead and do that.

Daniel Stillman: Going back to this question of how teams and orgs and leaders should be investing in this, it looks like they should be investing in doing less instead of doing more. I wrote something recently about how we need to have a meeting about meetings. And the first meeting of that meeting should be, what meetings can we not have. Now let's have meeting about which meetings to not have so that we can give people some time to find their unicorn space, speaking of invisible work.

Natalie Nixon:   Yes.

Daniel Stillman: And our mutual friend, Eve Rodsky's lovely book is on your bookshelf.

Natalie Nixon:   That's right.

Daniel Stillman: The idea that we should be encouraging people actively to be just doing joyful things that nourish them, that have nothing to do a direct economic output so that they will be happier people, so that we can get more out of them.

Natalie Nixon:   And yet they do. Listen, when we allow people to show up to work from the gut up, people will feel seen and heard.

Daniel Stillman: Yes.

Natalie Nixon:   And that fundamentally is the problem. And whether we're talking about a fourth grade class or a multi-billion dollar company, people need to feel seen and heard. And when any of us don't feel seen or heard, I don't know about you, but I start to like, dumb down, pulling back

Daniel Stillman: Yeah. I'll show you only as much of myself is absolutely required.

Natalie Nixon:   You have to absolutely value me. All right. Okay, cool. How authentically productive an organization are you really? You're not really getting the most and the best from people.

Daniel Stillman: No. Listen, our time together ... We don't have too much more time. What have I not asked you that I ought to have asked you? What is really important to make sure that we capture the message you'd everyone listening to grok from your ethos?

Natalie Nixon:   I think you asked a lot of wonderful questions, Daniel.

Daniel Stillman: Thanks.

Natalie Nixon:   And thank you again for inviting me. Just taking the time to dive into my work, I see that you did that and I really appreciate that. I don't know necessarily the question that you haven't asked, but I think that what's always just really important for me that people leave with is, is the opportunities to build their creative capacity and to, what I call oxygenate their ideas. That's how you go from an idea to reality. And oxygenating your idea, I made up that word, it's not really a verb, but to oxygenate your idea-

Daniel Stillman: No, it's totally a word.

Natalie Nixon:   Oh, it is a word?

Daniel Stillman: Yeah.

Natalie Nixon:   Okay, good.

Daniel Stillman: You can oxygenate water. Put more oxygen, take oxygen out.

Natalie Nixon:   I'm going to look out.

Daniel Stillman: It's okay. My first degree is in science.

Natalie Nixon:   You can oxygenate water, interesting.

Daniel Stillman: Oh, you totally can. You can deoxygenate water. And then if you do, a fish will not be able to live in that deoxygenated water.

Natalie Nixon:   Oh, I'm feeling a new metaphor coming up. Nice.

Daniel Stillman: It's a good word and you're allowed to use it. Even if it wasn't a real word, you still could. But anyway, please proceed with the thought that I have disrupted.

Natalie Nixon:   No. Just what I want people to leave with is, they have the agency and the ability to build a creative capacity and it takes some rigor. It takes some work. It's not always sexy. It's often very solitary. That's the rigor part. But I have this corollary expression, that I think it's in the book and I have this postcard about it, which is that, wonder is found in the midst of rigor and rigor cannot be sustained without wonder. So when I say that wonder is found in the midst of rigor, it's in the midst of doing the fundamentals, getting the mastery of skill, the solitary stuff. It's in those moments that an aha moment emerges. That's the wonder. And when I say that rigor cannot be sustained without wonder, we will burn out if we don't integrate moments and time for the awe, for the dreaming to ask new and different questions. Both are true and we have the capacity to do that. And it starts with oxygenating our ideas. Giving them light, giving them air, sharing them out.

Daniel Stillman: Yeah. I remember in grad school people were like, "Oh, I don't want to show people my portfolio without them signing an NDA." And I'm like, "Just show everyone your ideas."

Natalie Nixon:   Yeah. First of all, no one's going to interpret it the same way. There's literally nothing new under the sun. It's all about the remix. What's new is your mashup version of, your juxtaposition of the ideas.

Daniel Stillman: Yes.

Natalie Nixon:   If you live your life in that way, you're never going to grow. You're never going to take your work to the next level based on, we don't get anywhere alone. It's through sharing-

Daniel Stillman: Yes.

Natalie Nixon:   That someone says, "That's interesting. That reminds me of X, Y, Z, or you should talk to someone else about this, or would you to share this at the next [inaudible 00:45:21]." That's how things grow in momentum and energy and capacity.

Daniel Stillman: Yeah. Because you have to recruit other people to be excited about your idea. All right. Very quickly, aside from your book, the Creativity Leap, which everyone should buy and read, what other book do you wish everyone would read? What's your like, God, here's one fiction and one non-fiction book that everyone should just read these two books.

Natalie Nixon:   Well, the non-fiction book that I am crushing on right now it's called The Extended Mind.

Daniel Stillman: Yes.

Natalie Nixon:   By Annie Murphy Paul. I love this book.

Daniel Stillman: You mentioned it in your Fast Company book.

Natalie Nixon:   Yes. Because she's really uncovered and shares out so much research about new ways we should be thinking about the brain. The brain is embodied.

Daniel Stillman: Yes.

Natalie Nixon:   The brain is not disembodied from the neck up. I'm learning a lot more myself, teaching myself a lot more about the neuroscience and creativity and that's a lot of what she's getting into in that book. And I was loving this new model of the brain and the mind that she's talking about.

Daniel Stillman: I also want to give a shout out to Tyson Yunkaporta wrote a book called Sand Talk. He's an Aboriginal, I guess philosopher you might say. Sand Talk is writing on the ground as you think and talk and yarn with other people. I think embodied cognition, thinking rooted in land and spaces is ancient.

Natalie Nixon:   It is.

Daniel Stillman: It's very ancient. I think people should read both books. Because I want that new brain, people need to see that rigor. But talking to Tyson, you're like, "Oh my God, this is as old as people."

Natalie Nixon:   Thank you for that. And that's also what she's talking about in Extended Mind, is the role of gesturing, the role of moving.

Daniel Stillman: Yes.

Natalie Nixon:   While you're trying to remember things. And I think back to the way I used to memorize things and prepare for things in college, I would move. And if eventually you have to synthesize information in the seated position, there is that kinesthetic movement.

Daniel Stillman: Yes.

Natalie Nixon:   Our brains are taking cues from the body. This idea of embodied work is just thrilling. I'm going to read Sand Talk. Thank you for that. I just it wrote down.

Daniel Stillman: It's super awesome.

Natalie Nixon:   The work of fiction, two, one is an oldie but goodie for me. J. California Cooper, African American writer, my favorite novels of hers is There Is Confusion. I'm going to reread that book this spring because it's just a beautifully well told story. Sometimes from the perspective of this little spider. It's kind of, what is that form of literature from South America? It's a bit of natural-

Daniel Stillman: Magical realism.

Natalie Nixon:   There's a bit of magical realism in it.

Daniel Stillman: Yes.

Natalie Nixon:   It's also a beautiful love story as well.

Daniel Stillman: I think fiction is so important for that wonder part of our brains to get us back into human stories. I'm putting that on my bookshelf.

Natalie Nixon:   Fiction is important for building curiosity and curiosity is a precursor to empathy. If you actually want to emphasize more better, you need to read more fiction.

Daniel Stillman: Yes.

Natalie Nixon:   And the other work of fiction, again, this is not a new book, but he's a really prolific wonderful writer. A British Pakistani writer named, I think it's Mohsin Hamid, How to Get Filthy Rich in Rising Asia. I love that book.

Daniel Stillman: I remember that.

Natalie Nixon:   Is that he wrote it in the second person. Most books are written in the first person, I, we, or the third person. He wrote it in the second person. You sit there and you wonder, dah, dah, dah. There was something so brilliant about, oh my God, I'm there. I love of that.

Daniel Stillman: Yeah. The only other book I know that does that is Bright Lights, Big City by James McInerney, which is so weird to read a book in second person. And if you haven't read, I mean, to anybody listening, I remember when that came out and it's such a catchy title. I'm going to put that on my list too. With the one minute we have left because Natalie probably has another meeting to go to because that's 2022 you all. If people want to learn more about all things, Dr. Natalie Nixon, PhD, where should they find you?

Natalie Nixon:   They can simply go to figure 8, the number eight, thinking.com. So figure 8, like ice skating, figure8thinking.com. And they'll learn all about my speaking and advisory work and a lot of cool downloads if they want to download some cool stuff too.

Daniel Stillman: There you go. I think we'll leave it right there. We'll call scene.

Natalie Nixon:   Scene. Thank you, Daniel. This was so much fun. I really appreciate your time.

Daniel Stillman: Thank you. I really appreciate it. This was fun. I learned a lot.

Turning a Challenge into an Agenda

How do you turn a question, a problem, or just a list of needs, into an agenda?

At the close of a recent cohort of the facilitation masterclass, the participants were still sitting with some big questions. Which is good, because that's what the closing session is for! But I felt that some of these questions were too big for one conversation. So, I invited four alums of the facilitation masterclass to come together and share some thoughts on a fundamental challenge: turning a question into a conversation, an agenda and an arc. 

I’m joined by 

Erica O’Donnell, a hybrid professional working at the intersection of design thinking, strategy, facilitation, and innovation,

Kyle Pearce, a leader in collaborative change with an extensive background in the health and social services sector.

Frankie Iturbe, a Program Manager at Newsela, a K12 EdTech company

And Kate Farnady, Director, Chief of Staff, Strategic Technologies at Autodesk, and also the community coordinator for the Conversation Factory Insiders’s Group!

We only scratched the surface, but there's lots of goodness in here.

Just a few of the things we discussed:

  • How stated goals may not always have the whole group aligned with them, and what to do about it.

  • Sharing responsibility for the agenda and outcome with stakeholders and session attendees

  • How good insights can sometimes arise even in spite of (or perhaps because of) chaos

  • Different approaches to facilitating agendas around messy goals and questions

If you want to dive deeper, check out my course on the 9Ps of meeting planning. I'd also recommend signing up for the conversation factory insiders group...we ran another deep dive on this question, reflecting on the question "why do I need an agenda?" and sharing our responses together. You can join here and check out that session as a subscriber here.

Links, Quotes, Notes and Resources

Frankie on LinkedIn

Erica on LinkedIn

Good Seed Digital

Think: Act Consulting

Minute 11

Erica O'Donnell:

I think this really leads into one of the things that I wanted to talk about which is, I think a lot of times particularly maybe internally, I don't know. I don't have as much experience but we assume that we know that the clients or the people that we're engaging with know what the problem is, or the goal. They've defined something and we assume everyone's aligned.

I think that's actually before we even start talking about process or designing an arc, we really need to make sure or that we spend time making sure that everyone is aligned. And one of the ways we might do that is actually having some pre sessions to the session where we encourage divergent thinking before we try to align and converge. And so, we can with those key stakeholders who are maybe responsible or for defining a goal, helping them get to what the true goal is.

Minute 14

Kyle Pearce:

Well, I think what happened is exactly what Erica was saying is, the group had never had the courage to walk into that conversation because it's a deep and difficult conversation. These are the conversations that many people avoid. And so, I think what had happened was there is critical mass of people on the board who had assumed that it is like you say, I love the way you framed it which is, "We want to recruit indigenous people to the board." That is true. But the pathway to that is not simply finding people who will come and sit on the board.

My point to them, and the next stage of this work with the group is the pathway to having people on the board successfully who bring diverse perspectives, is creating a sense of belonging among the people who are already there. If you can't create that sense of belonging then those people, the people you want to be on the board are not going to last and it's not going to be successful.

Minute 19:

Daniel Stillman:

But I think that's one of the powerful things a facilitator does is to push back to say, "Well, this is your goal and this is what you say you want. And your current plan will get you there, which is why we need this other way of doing things." I think that to me, that purpose and product were those first two Ps that made so much sense to me. It's like well, this is what we want. And this is what we want to have in hand by whatever. Next week, next month, next year, whatever it is. That is concretizing, not just this lofty purpose but the real changed reality.

Minute 36

Frankie Iturbe:

But I think very simply it was all about once I had these topics, taking time to gather the input from those stakeholders to have them shape the agenda. I think yes, I had a set of topics but digging in with them to understand what they wanted to achieve was really important.

I think the other point I want to make on this portion is we'll often get told, we need this product, we need this deliverable done. Sometimes it has a tendency to overlook the real problem or what they really want. I think that's why that one-on-one either again pre-workshop, or during the workshop to unpack what we're really trying to solve for, what's the real challenge is important.

Minute 38

Frankie Iturbe:

It was my first time in front of this group of VPs and sales directors, so I was a little nervous and I was again, adding a lot of pressure on myself. In working with Daniel, I was thinking through well, how can I change that? How can I not feel so anxious or nervous and excited about this? I realized it was about sharing the responsibility with my workshop attendees, with my meeting attendants.

I realized I was seeking liberation. I didn't want to feel so like a massive weight on my shoulders over needing to crush it for this group. And so, I think I was able to open that workshop with saying, "Hey, I'm really excited what we can accomplish today. I put a lot of work into helping us get here, but I can only do so much."

It's your responsibility as well if something's not working for you to raise your hand and share a suggestion as to "Hey, how might we tweak this agenda so that we achieve the objective that you wanted?" I just, I wanted to share that piece because I've really been taking that into my work lately that, look if not, I don't need to put it all on my shoulders. Shaping this agenda, shaping this workshop is about sharing with others and letting others help shape it as well.

More About the Guests

Kate Farnady

I'm a generalist experienced working with senior executives and leadership as well as management and individual contributors to identify priorities and cross-functional process, provide clear and effective communication, remove obstacles, and make things happen.

I specialize in identifying and bridging communication gaps to help understand the big picture, facilitating prioritization and alignment, getting the best ideas on the table, and driving execution. I identify the audience, articulate the mission, clarify objectives, determine goals and metrics, draw up strategy and process, and oversee implementation. I've worked closely with finance partners and budget analysts to ensure financial alignment towards execution targets.

I've managed a wide variety of projects, working with diverse subject-area experts. I consider myself a strategic problem solver and I thrive in rapidly changing environments. I am resourceful and flexible, comfortable with ambiguity and easily adapt to new challenges.

People are my passion. I'm a thoughtful listener and facilitator with high EQ. I have worked closely with HR and people ops departments on many people-focused initiatives. I am deeply invested in empowering people through effective communication and feedback, collaboration and including diverse perspectives.

Frankie Iturbe is a Program Manager at Newsela, a K12 EdTech company. He considers his role part strategist, part designer, anchored on delivering a world-class sales experience for customers and sellers. This work keeps him entrenched in the exciting worlds of sales and facilitation. Outside of his 9-5, he publishes content on LinkedIn for job-seekers pivoting their career to more purposeful work. Reach out to him on LinkedIn to connect further. https://www.linkedin.com/in/francisco-iturbe

Erica O'Donnell (she/her) is a hybrid professional working at the intersection of design thinking, strategy, facilitation, and innovation. Her practice focuses on guiding collaborative teams to co-create products, services, and experiences that drive business and social impact. This human-centred approach helps to drive alignment across multi-faceted teams, break down silos, and encourages team ownership of the outcomes. Erica is a firm believer in leveraging a team's collective wisdom layered in with real user data to drive design decisions, whether designing employee experiences, customer experiences, or digital products. Her superpower is guiding teams to translate various inputs into actionable insights and strategic roadmaps. Erica created Good Seed Digital and hopes to make a difference in her community, one good seed at a time.

Kyle Pearce (he/him) is a leader in collaborative change with an extensive background in the health and social services sector. Kyle has worked in the field for over twenty-five years, as a program lead, community developer, social entrepreneur, executive director and funder.  He is the principal of think: act consulting.

think: act consulting inc. is an incorporated strategic consulting firm based on the traditional, unceded territories of the Squamish, Musqueam and Tsleil Waututh First Nations. Think: act’s focus is improving services and access to services for vulnerable populations, working with service providers and citizens, managers, leaders and executives to take stock of a situation, assess how to move an ambitious agenda forward, and implement a path of action that will achieve their vision. 

think: act consulting. We bring expertise in community action, health and social services, business planning, project management, funding and organizational systems, as well as skills in facilitation, communication, community engagement, research and analysis, and executive coaching. Our goal is to improve the world for the benefit of future generations.

Full Transcript

Daniel Stillman:

What I'm going to do is, I'm going to record on this computer and... Oh, I'm so nervous. I'm excited. I'm going to officially welcome you all to the Conversation Factory. Yay. We are here to potentially unpack deeply this question of how to turn a purpose and goals of a stakeholder into a powerful agenda, and an experience arc? Did I get that? Kyle, what was the question that you... Because we were discussing before we started the different ways of framing this question.

Kyle Pearce:

Well, I can work with that. I think the original question that I was coming with, which isn't too far off from what you said was. How do you turn a question or a purpose, a client's question or problem into an agenda?

Daniel Stillman:

Yeah.

Kyle Pearce:

The reason we get involved with clients is because they have problems and questions.

Daniel Stillman:

Yes.

Kyle Pearce:

So I'm not going to answer or whatever else you're throwing at me.

Daniel Stillman:

Another reason why I've gathered you all here today is we said before we started recording, is some of us work internally inside of organizations where the client is a key stakeholder or multiple stakeholders. Some of us do this externally as a consultant. And some of us have done both. And so, I thought it would be interesting to have you all come here.

Daniel Stillman:

This was sort of a big question that even after 12 weeks of the last facilitation master class people were like, "Well, how do you really do it?" How do you really take a big, hairy, messy question and turn it into as Rudyard Kipling said "The unforgiving minute into 60 seconds worth of distance run." I think what my hypothesis was is if we could just say hello and who we are, and then we can all share a story. And then just have a deeper dive on anything that's come up. And so, I will say ladies first. Erica, would you like to say hello and tell a little bit about who you are?

Erica O'Donnell:

Yeah, absolutely. Hi Daniel. Nice to be here with you. I'm Erica O'Donnell. I work as a consultant, one of those external people that you were just talking about. I really work at the intersection of strategy, facilitation, design thinking and innovation. I help organizations, really guiding their cross-function teams to design innovative products and experiences using collaborative methods.

Daniel Stillman:

And so, you have solved this question many times, which is why you-

Erica O'Donnell:

Yeah. Absolutely. Yeah. I have.

Daniel Stillman:

Kate, I'm so glad you came. Welcome on board. Tell the folks a little bit about you.

Kate Farnady:

Thank you. I as always, I'm so glad to be here. I am a chief of staff and I have been a chief of staff in various different engineering orgs for much of my career. And that lands me in squarely at the intersection of organizational strategy operations, and complicated diplomatic cat herding.

Daniel Stillman:

Yeah. And you've done this internally and externally?

Kate Farnady:

Yeah. Mostly I've done it internally. But I have done some pretty hefty consulting projects with engineering, and really different kinds of engineering operations around strategic planning especially. But also executive coaching.

Daniel Stillman:

Frankie. I just noticed that you have a believe sign behind you. Now that I've been watching Ted Lasso, I know what it means.

Frankie Iturbe:

That I do Daniel. I know you just recently became a big Ted Lasso fan. I'm with you there.

Daniel Stillman:

Well, the challenges my wife, God love her, has a hard time with media that has a lot of characters. Somehow Ted Lasso was inspirational enough that even though there are indeed a lot of characters in Ted Lasso, she was able to strap in and get involved. I'm really excited because it's a great show.

Frankie Iturbe:

I'm happy she's able enjoy the beauty of Ted Lasso that it is.

Daniel Stillman:

Hey, thanks for coming. I'm glad you're here too. Tell the people a little bit about you because some of these people are new to you as well.

Frankie Iturbe:

Daniel, let me start by saying it's an honor to be on the Conversation Factory. I thought many years back when I met you, "It'd be cool to be on his podcast one day." And here we are with a great group of facilitators. It really is an honor. I'm super excited for this conversation today. Let's see about me and my background. I spent about seven years in consulting almost, just wrapped that up earlier this year of doing technology and management consulting. While they're, worked a lot with helping clients apply design thinking within their sales organizations. How do you take photo market strategy, make it real across systems process, all that good stuff.

Frankie Iturbe:

Then I recently transitioned to a company named Newsela, where Newsela is a K-12 education technology company. And still within the sales org, similar to the work I was doing before. But again, helping us, how do we take our go to market strategy and really use it to again, design the systems and process that are going to help us achieve our sales targets.

Daniel Stillman:

Thank you Frankie. Thanks for being here again. Kyle, what is up? I'm so glad you're here. Tell the people.

Kyle Pearce:

Me too. And glad to see Kate and Erica. Glad to see you too again. Nice to meet you Frankie. Looking forward to this conversation.

Daniel Stillman:

Also, nice winter beard. Can I say? I don't feel like I've seen you with this before.

Kyle Pearce:

You know what? I actually started growing this on the hottest a time of the summer. And I've discovered that the magic of trimmers male hygiene apparently is a thing. And-

Daniel Stillman:

It is. We can have a whole other conversation about that.

Kyle Pearce:

Yeah. Thank you very much for that.

Daniel Stillman:

Well. That means we haven't seen each other in way too long if this is my first introduction to your beard.

Kyle Pearce:

Yeah. Well that's okay. We're getting to know each other all over again today. A really brief introduction Kyle. I use he and him pronouns. I'm in Vancouver, BC or the traditional territory of Squamish and Tsleil-Waututh nations. I have a consulting firm called Think:Act Consulting. And the focus of my company is on improving services or access to services for marginalized populations.

Kyle Pearce:

I love this conversation because I'm also straddling two other new areas, one of which is environmental sustainability. I've been moving into doing more and more mindful work in the field of anti-racism, specifically with people who have privilege. So this is a great opportunity to share a story that's right at the intersection of almost all those things.

Daniel Stillman:

That is awesome. Well, Kyle, since you're currently holding the mic. Do you want to tell a story about how you had this challenge and maybe succeeded at this challenge, or as Kate set up struggled mightily with this challenge and achieved a lesson?

Kyle Pearce:

Well, I think the challenge that I can talk about or the situation I can talk about is more about how we catalyze something from a problem that a client has. I'm still in the middle of figuring out how do we make a complete agenda, but maybe I'll just situate it. I do a bunch of work, mostly with healthcare organizations but I also work with community agencies. I've been work working with a community center here in Vancouver doing a strategic plan, pretty straightforward.

Kyle Pearce:

I've my bells and whistles and my process for doing this kind of work, a beautiful group. A group who like many community agencies has really been touched and inspired by Black Lives Matter movement. And also by this push that's happening up here in Canada around, this terrible problem of anti indigenous racism.

Kyle Pearce:

And so, as part of the strategic plan from the very first meeting, the group was really clear. Or at least most of them were really clear that they wanted to do anti-racism work and they wanted to do decolonizing work. We call it reconciliation as well. This movement went straight through first, second, third, fourth and we're in our fifth meeting, we're kind of looking at our draft strategic plan.

Kyle Pearce:

When the small groups are breaking out, I overhear that in one group there's one of the board members is really having an adverse reaction to anti-racism, the term anti-racism and decolonizing. And framing it is, this is so negative. This word anti, it sounds like so aggressive and negative. When that group came up to share what they had talked about, in fact they had watered down this very, very significant initiative and presented it to the board. I could feel in the room, there was a great tension and anxiety as this group was talking.

Kyle Pearce:

I guess one of the participants in that group said, "You know there's this term here, decolonizing. What does that even mean?" I paused and I asked the group to pause and just take a deep breath because we were at a pretty crucial spot in the conversation. I asked them to close their eyes and to think about everything that they had ever learned about indigenous people as a child, and to reflect on what they'd been taught.

Kyle Pearce:

Then I asked them if anybody was taught positive things about an indigenous people, please share that now. And there was nothing that could be shared in the room. And so, we talked, we launched into this conversation about what decolonizing means. It's just a word but at the end of the day, it's about touching us at a very deep interior level. And going back to our own history and how we shape the world through the opinions and ideas that we get as children.

Kyle Pearce:

We're at the point now where I'm talking with the board chair about how, if you want to, if this organization wants to recruit indigenous people to the board, they have a toxic board by virtue of the fact that they're not really ready to have these conversations. I don't know how the agenda's going to shape up but it shapes up with a question like that with a challenge, with a big problem that is a challenge that that board is sharing. The only way I can think of doing it is going deep.

Daniel Stillman:

When you think about... Oh sorry, was there some else-

Erica O'Donnell:

Oh, sorry. I was just going to say, I think that's so interesting Kyle. I think this really leads into one of the things that I wanted to talk about which is, I think a lot of times particularly maybe internally, I don't know. I don't have as much experience but we assume that we know that the clients or the people that we're engaging with know what the problem is, or the goal. They've defined something and we assume everyone's aligned.

Erica O'Donnell:

I think that's actually before we even start talking about process or designing an arc, we really need to make sure or that we spend time making sure that everyone is aligned. And one of the ways we might do that is actually having some pre sessions to the session where we encourage divergent thinking before we try to align and converge. And so, we can with those key stakeholders who are maybe responsible or for defining a goal, helping them get to what the true goal is. Because actually what I'm hearing you say is the goal they stated and the actual goal is a little bit different.

Erica O'Donnell:

They wanted to do some work in this area, but in fact one of their goals is to recruit indigenous board members. How do those ladder up? How do we align to those? Then we can start to talk about designing arcs of sessions or multiple sessions, convenings. I think sometimes that's about problem framing, sometimes if it's a larger system like you're talking about maybe there are ways to get to more clear and powerful, shared intent. Where you're really digging deep into what the intention is of the session or of the group, and not just taking that face value goal.

Daniel Stillman:

I think that's a really interesting lesson to take Erica. I'm curious Kyle, clarifying and aligning to purpose it's a really good point. We assume in the founding question is we've got there. Was that the lesson you took from that?

Kyle Pearce:

Well, I think what happened is exactly what Erica was saying is, the group had never had the courage to walk into that conversation because it's a deep and difficult conversation. These are the conversations that many people avoid. And so, I think what had happened was there is critical mass of people on the board who had assumed that it is like you say, I love the way you framed it which is, "We want to recruit indigenous people to the board." That is true. But the pathway to that is not simply finding people who will come and sit on the board.

Kyle Pearce:

My point to them, and the next stage of this work with the group is the pathway to having people on the board successfully who bring diverse perspectives, is creating a sense of belonging among the people who are already there. If you can't create that sense of belonging then those people, the people you want to be on the board are not going to last and it's not going to be successful. Daniel, your mic is on mute.

Daniel Stillman:

It's bound to happen at some point. I was typing and therefore I did not want to click it clack into the microphone. Just to unpack this one more level as Erica was saying, pushing back against somebody's purpose and making sure that the purpose is clarified and saying that they're not going to get there with the current pathway, is actually a really powerful thing to say to a stakeholder. Then I think that's profound.

Kyle Pearce:

It is-

Erica O'Donnell:

Yeah.

Kyle Pearce:

Sorry. Go ahead Erica.

Erica O'Donnell:

Yeah. I was going to say, I think it's really interesting because obviously you're talking about a very highly emotional topic. But actually we see this even if we're just talking about designing products. Because the engineering stakeholder, the head of product has a different desire for what they're looking for to get out of potentially the head of design.

Erica O'Donnell:

My point is it's not even really necessarily always about the topic and being fraught with emotion. It can just be a matter of misalignment and making sure that we understand what those key blockers or barriers that the group might be seeing to feeling accountable to achieving this collective work, and working through those before we ever start designing an agenda.

Daniel Stillman:

I'll [crosstalk 00:16:40]. Oh, sorry. Go ahead Kate. Yeah, jump away.

Kate Farnady:

I'm going to jump in and just make trouble. Which is that one of the things I've experienced is that, sometimes you can't even have visibility into the lack of alignment or the depth or extent of the lack of alignment until you get into conversation. And so, I think there is also a case for the diving in and revealing, and exploring. I think it really depends on what your topic is. And there's like for sure, sensitivity and around topics. Sometimes the diving in is what gives you the real story that you need to be productive, and you might not see it, might not even be able to access it to dive in.

Daniel Stillman:

Frankie, you had your hand up.

Frankie Iturbe:

Yeah. Something I want to jump here and mention, it's gotten mentioned a bit and Kate brought it up here in referencing alignment. And then Erica briefly mentions problem framing. I want to double stitch that here for a sec so. I think you can approach this problem framing either in co-planning, which Erica alluded to leading up to the workshop or your meeting.

Frankie Iturbe:

There's time to go one on one with your stakeholders and start to understand what their view of their problem statement is. Or I think you can work that into your agenda. Where you can use something like the abstraction ladder to look at the why and the how of your problem statement and do it in your workshop. You're driving that alignment in the workshop. I think I've approached it both ways. Both forms where you're doing it ahead of the workshop or meeting with co-planning or during the workshop. But ultimately what you're doing is you're reframing the problem and you're driving that alignment.

Daniel Stillman:

Yeah. I think either way, there's always a risk that as you say Kate, people may not actually know that they disagree until they get into the room and getting into the conversation. When I think about the nine Ps of planning, this purpose, we started with purpose and the pushback which maybe is another P hilariously is, do we in fact, are we truly aligned to purpose? And do we do that in a pre-conversation or not?

Daniel Stillman:

But something else I heard from Kyle, I think is interesting. And then I think we should shift to someone else, sharing another story is. I always find that clarifying the product, and Erica your sense that the product is a product. But in your sense, Kyle the product is a different reality, a different changed experience. And if somebody says, "This is our result, we'd like blank." Then you can say, "Well, we're not going to get that with our current approach. Therefore I have this other approach it's called realizing that anti-racism exists."

Daniel Stillman:

But I think that's one of the powerful things a facilitator does is to push back to say, "Well, this is your goal and this is what you say you want. And your current plan won't get you there, which is why we need this other way of doing things." I think that to me, that purpose and product were those first two Ps that made so much sense to me. It's like well, this is what we want. And this is what we want to have in hand by whatever. Next week, next month, next year, whatever it is. That is concretizing, not just this lofty purpose but the real changed reality.

Daniel Stillman:

We're going to know this is working when our board is blank percent. And if they can align on that like, well, yeah. Okay. That's how we'll know who's successful. Then we can go back and say, "Okay, well, how do we get us there?" Sorry, Kyle, is there one more thing you wanted to say to [crosstalk 00:20:35]-

Kyle Pearce:

No, I just love that. And this is why I like this group. We all come from different... My work is mostly in fuzzy areas, but the bottom line is there is no direct path to the outcome. There's a whole E circuit of conversation, there's external conversation, there's internal dialogue, there's transformative work that has to be done. Sometimes there's simply change on the board of the organization. It surfaces on things that really need to be worked through at a deeper level so.

Daniel Stillman:

Well, it's really funny Kyle because in a way in the implied in the question that the group was asking, is the assumption that there is a perfect arc that will guaranteed get me to the thing I want. And what you're saying again is questioning that it's, if it's in complexity it will be wrong in ways you can't even imagine until you get started.

Kate Farnady:

Well, actually Daniel I would add to that if it involves human beings [inaudible 00:21:34].

Daniel Stillman:

Or technology, which is made by human beings.

Kate Farnady:

Yeah. It is true. I reflect on the notion of a board that wants more diversity, but doesn't believe in the concept of anti-racism or can't talk about it is not a safe board for anyone who-

Daniel Stillman:

Yeah.

Kate Farnady:

So there you go.

Daniel Stillman:

But they're working on it.

Kate Farnady:

Yeah. Totally. And good luck with that. I mean that genuinely.

Daniel Stillman:

Yeah. Yeah. Yeah.

Kate Farnady:

It's important work. We got to do it even though it's really painful and hard.

Kyle Pearce:

They're clearly not the only board that has this issue.

Daniel Stillman:

No. Who else has a story of an amazing winner or a terrible failure, or as Kyle did the middle, the messy middle? Kate is not only raising her hand, she's wiggling her fingers.

Kate Farnady:

I know. I'm just feeling it. And this conversation is going in such a beautiful direction to fit my messy story. Which is in engineering organizations, it's a perennial challenge as budgets, urban flow, and as people come and go, there's always this question of overworked teams and prioritization. Like how do we build capacity? Or what is the problem we're trying to solve here? How are we getting in our way?

Kate Farnady:

I've had the experience with engineering leadership teams of like okay, let's solve this. And the experience where we like, okay. We have our problem statement, we build a mural, we've got four stages. We're going to do a discovery stage, we're going to surface all the ideas, and then we're going to cluster them and figure out what the big themes are. Then we're going to vote on them, and then we'll come up with our number one big theme. Then we'll go and-

Daniel Stillman:

Very rational design thinking-driven approach.

Kate Farnady:

And it was like, it made so much sense and it became clear to me. We took it, and actually I wasn't even driving the mural, I was kind of co-facilitating. I had someone else who was kind of driving this concept of these stages in the mural, and this is how we'd come to the answer and I let them run their course. But actually it was within the first like 10 minutes of the, we hadn't even gotten to the clustering. We were doing the thinking of all the issues, and coming up with the kind of wild brainstorm.

Kate Farnady:

It just became so clear that we had opened Pandora's box. In a way that even in the time we had, I think we had a 90 minutes. That I could already see as the box was opening, and the things were starting to fly out that the idea of actually like going through this process and voting on one, that was going to be the one we'd focus on was just absurd, completely absurd. And so, we had some chaos and then we had a chaotic experience of clustering.

Kate Farnady:

Then we had this mural that was poorly clustered because there's so many arguments for how you could categorize things. And people were kind of disagreeing and saying like, "Oh, I need to add one more thing. Or actually I think we need a different category." Then our process person, bless their hearts, was pushing to a vote. And so, we were kind of before it. We were in chaos about the ideas, the clustering was off and this person was really pushing a vote.

Kate Farnady:

And so, we did this vote and then we ended the session because we didn't have time. It was just amazing. And I had decided to go ahead with it because I thought, we could just wait, we could try to make it perfect. We could try to think it through more, we could try to get buy-in ahead of time. I just said, "What the heck? Let's just see what happens. What's the worst thing that could happen?"

Kate Farnady:

And so, one of the other things that happens is two people got in a fight. And they got a fight and they couldn't figure it out, they couldn't see each other's perspectives. We ended the meeting and I felt like a facilitation failure. I just sat on that for a while and was like "Oh, this is hard." Then I went back to the mural and I took it and I wrote it into bulleted points and I looked at it and looked at it, and all of a sudden I saw a bunch of themes. It turns out that everybody else went away from the meeting and were thinking and thinking.

Kate Farnady:

The two people who got in a fight came back together and unpacked the fight separately. And was like, "I think I misunderstood you and I want to make sure we under... So that piece happened on the side. That was interesting. Another person came back and said, "You know what? In that conversation I got a new understanding of what was going on with my team, and I wouldn't have had that. I'm coming up with an idea of something I want to tackle because of it."

Kate Farnady:

Then I went back to my boss and I gave my boss the downloaded words of the mural. They started looking at it and we started to identify a really big theme. And so, what happened was this unleashing of the chaos was something that actually allowed us to get visibility into the lay of the land in a way we really didn't have before. And we're like, the next step was really to pull out a few threads. Look at the themes, pull out a few threads and decide as an organization where we could really make some impact. And it came in different places.

Kate Farnady:

It came in this like relationship that evolved because of a fight and coming back and oh, there's a good word for it but my old brain is forgetting it. It was just like this reconciliation process was a big learning experience for them. The one person who came out of it with a pilot project and then coming back at a meta level on the leadership team and having a picture of how our team operates, how they think [crosstalk 00:28:03]-

Daniel Stillman:

So Kate can-

Kate Farnady:

... to do as leaders to get traction.

Daniel Stillman:

Sorry to... Well-

Kate Farnady:

No-

Daniel Stillman:

I'm jumping in because of time. But also I'm wondering, I think this is a really great story of... And also Eric, I see you have your hand up too. I'll loop you in just a second. This sounds to me like a story of creating success out of complexity. But in terms of the question that we're posing, when you think about, I wasn't actually clear from the story, whether you or the process person was the person who designed this flow. And where you feel like if we were going back to the beginning, what you would've done differently in terms of designing the arc. Or if we're just accepting that oh, messiness and complexity is the way that this will always happen. I mean, the way Kyle is sort of proposing.

Kate Farnady:

I would say there's a million other ways to do it, for sure. And in this case I was happy that we dove in. And it was the ownership of the plan was unclear, we didn't really know. I think there was a way in which going into it with chaos really helped us identify what problem we needed to solve. And so, I think that's-

Daniel Stillman:

It's interesting. Because when we look at the question, how do you turn a question into a process and an agenda? It sounds like you loosely did that.

Kate Farnady:

We turned a process into a question I think. Now we're applying a process to it.

Daniel Stillman:

Yeah. It's interesting. Erica, what's this sparking for you?

Erica O'Donnell:

Well, I love it. I love how Kate just embraces that messiness. I so much more, want everything buttoned up and know exactly what I'm going into you as anyone of you that have worked with me know, I do sort of more linear thinking. And so, one of the things that sparked for me was this idea of the maybe unintended consequences, which were about connection between her team members for example.

Erica O'Donnell:

I really like this framework that was developed by a group called CoCreative out of Washington DC. And they have what they call Four Agendas in Collaborative Innovation. And one of them just really spoke to me with what Kate was talking about, which is their connecting agenda. So they use the heart as an example for that. And really, that's focused on developing relationships within a network or a team.

Erica O'Donnell:

It's interesting, a lot of these aligned to some of the meeting OS that we looked at in the last facilitation, or two facilitation Fridays a go with Trisha Conners too with types of meetings. They have a connecting one. They have one called aligning which is really, they use the spirit as the icon for that. That's really about defining intent and best worst case scenarios, that kind of thing.

Erica O'Donnell:

They have a learning agenda, symbolized by the head and they have a making agenda. This is the space that I usually play in is in the making, when we're talking about products and experiences. And so, I'm really comfortable there. And this is prototyping and testing and all of the stuff that any of us who have worked in digital or in product are really familiar with.

Erica O'Donnell:

But some of the other agendas, those frameworks I think are really important to dive into and understand. Even if you're in a making process, there are always the edges of all of those other things that are happening. People are learning, they're connecting, they're aligning.

Erica O'Donnell:

And so, how you create an agenda and include or an arc of a session or multiple sessions needs to have the core primary purpose. But you always need to also be thinking about those edges of the secondary or tertiary ways that people are working together, and what they're producing. Isn't always just a prototype might be a better relationship between two people that need to work together, right?

Daniel Stillman:

Yeah. That's so interesting. I love the idea that there are these multiple agendas. We always know that people have multiple agendas in group work, but the idea that a facilitator needs to be aware of these multiple layers. And that it's not simply about, what are we going to do when during this time we have together? It's these other layers, which is really awesome. How has that changed how you work? Sorry. Frankie. Was there something you wanted to "yes and" on that?

Frankie Iturbe:

All I was going to add there to Erica's point was I'm a huge fan of, after you align on that objective, that outcome, finding those recipes. Those agendas you mentioned from CoCreative that are there. I think I'm a big fan of it's a proven recipe or a combination for a reason, big fan of LUMA Workplace as well obviously. Yes. It's important to take those and break them where it makes sense, but those recipes often are tried and tested. And that very often will start my planning process working around those because I know those work. Those have been used for years and years.

Erica O'Donnell:

Yeah. I would agree Frankie. I go to those and then the double diamond, like divergence convergence is always right at the core. And whether that's to define, the space that we're working in. Are we working in the problem space or the solution space? At a macro level but also in the more micro level in each session, you're probably going through that arc of problem solution, problem solution across either one or multiple sessions. So using those models that we have and those recipes, I like that language like pulling the recipe. We can tweak a recipe but there's a reason, the basic ingredients work and it's been tested so I like that language a lot.

Frankie Iturbe:

I think Daniel encourages us to be... I think you've written about this somewhere Daniel for us to use recipes, but to also be chefs and make our own, correct? Something like that. I've heard you mention.

Daniel Stillman:

Sure. Well, it's funny my friend Patty who's an amazing chef, there's this idea of like you're tasting it as you go. That's where sensing and responding and deciding like oh, this is going horribly wrong but continuing to work with it. And trusting that something interesting can come out of it is I think in a way what... I think Kate, what I'm taking from your story is yeah, things might be messy in the middle but something good might be on the other side.

Daniel Stillman:

And Erica's point that unless we address these three other agendas intelligently or thoughtfully, they're going to manifest themselves regardless. We have like about 15 minutes left, which means I'd like to make sure that we hear a story from Erica and Frankie as well as some unpacking together. Who wants to go next? Who's got a story to share?

Frankie Iturbe:

I can jump in Daniel.

Daniel Stillman:

Sweet.

Frankie Iturbe:

All right. Well, let's see. So I'm take us back to a recent experience in my new job. Well, I've been here about six months and not so new now, facilitating a workshop on the inside internal. Quick bit of context. I think actually going back to the prompt Daniel you said, how do you take a question turn that into a process or an agenda? Something I realized as you said that was well in this scenario that I'm going to walk through, is I wasn't given a question. I was given a set of topics.

Frankie Iturbe:

Hey, Frankie. We need to put together a sales territory map, a org structure, and a set of guidelines for a working relationship between our employees. And so, I think that's where it's a little different. You're not given a question, you're given a set of topics. How did I approach that? I think something I'll see, hopefully you'll you throughout the story is leaning on my stakeholders. What, for example in a workshop, I think Daniel, we call that lazy facilitation. We'll elaborate more on that in a second. But you can also apply that leading up to.

Frankie Iturbe:

I think it's easy, at least for myself in the midst of this workshop. I put a lot of pressure and self-induced stress on myself in getting ready for it. But I think very simply it was all about once I had these topics, taking time to gather the input from those stakeholders to have them shape the agenda. I think yes, I had a set of topics but digging in with them to understand what they wanted to achieve was really important.

Frankie Iturbe:

I think the other point I want to make on this portion is we'll often get told, we need this product, we need this deliverable done. Sometimes it has a tendency to overlook the real problem or what they really want. I think that's why that one-on-one either again pre-workshop, or during the workshop to unpack what we're really trying to solve for, what's the real challenge is important.

Frankie Iturbe:

Then the last part I want to jump through. Two more quick points I'll hit on the story is. So after I spent a lot of time with my stakeholders and whatnot, it was group of five that I was working with to develop these sales assets. I had a ton of notes, a lot of complexity. And I realized actually, through working with you Daniel through one of our sessions together, I had to just simplify it.

Frankie Iturbe:

I had all this information and I really needed to just take it to a clean agenda. I have two days that means I have two halves in each day, the morning and afternoon. And I probably got two segments in each of those halves. From there, I was able to take it down to a really simple agenda where I then started taking that around to my stakeholders, and sharing it with them to gather the feedback on that. So really simplifying it I think, was really key in my process there and just listing out a simple agenda.

Frankie Iturbe:

The last I want to close on with this story is I mentioned earlier, I went into this workshop. It was my first time in front of this group of VPs and sales directors, so I was a little nervous and I was again, adding a lot of pressure on myself. In working with Daniel, I was thinking through well, how can I change that? How can I not feel so anxious or nervous and excited about this? I realized it was about sharing the responsibility with my workshop attendees, with my meeting attendants.

Frankie Iturbe:

I realized I was seeking liberation. I didn't want to feel so like a massive weight on my shoulders over needing to crush it for this group. And so, I think I was able to open that workshop with saying, "Hey, I'm really excited what we can accomplish today. I put a lot of work into helping us get here, but I can only do so much."

Frankie Iturbe:

It's your responsibility as well if something's not working for you to raise your hand and share a suggestion as to "Hey, how might we tweak this agenda so that we achieve the objective that you wanted?" I just, I wanted to share that piece because I've really been taking that into my work lately that, look if not, I don't need to put it all on my shoulders. Shaping this agenda, shaping this workshop is about sharing with others and letting others help shape it as well.

Kyle Pearce:

I love that Frankie. You're speaking to the core piece, which is something that I learned from Daniel, and with Kate, and Erica. Which is that we often as facilitators believe that the problem is ours, question is ours. Our responsible is to answer it and to come up like when we're having these great discussions about when it falls apart. But at the end of the day our job is really to help our participants both identify the problem and the solution.

Erica O'Donnell:

Yeah. I love that. I use Daniel's words a lot, which is to create the conditions for transformative conversation rather than forcing the transformative conversation is very different, or being responsible for the outcome of that conversation. It's about creating those conditions. That's what we're accountable as facilitators. It's a bit of a mind shift and I really think it aligns with what you're talking about Frankie.

Kate Farnady:

That all really resonates for me in thinking about what my experience of the chaos was, was that the path really emerged from the chaos in a really productive of way. But it needed that space for people to be able to contribute and expose the ideas and participate in that way.

Kyle Pearce:

Can I reframe that, Kate? I love it because the question that your group ultimately had was, how can we work through these complex problems? Instead of providing a process for them, you actually engaged them in an experiential learning process of how they did it. Then they use their own resources. This is the other thing is, we often take these responsibilities on because we underestimate the resources of the people in the room. I love the fact that that messy, messy processing ended up helping those people emerge, emerge their own strengths.

Kate Farnady:

I'll add one thing. I think that's a great reframing. It was a group that was really in the forming, in the forming storming norming phases. And so, and it was an internal group. And so, there's a way in which that really was part of the formative storming phase and it helped move the team forward in that respect as well. It's kind of back to Erica's point.

Daniel Stillman:

Speaking of Erica, we need to get to you. There's just one thing I want to make sure I say, so I don't forget it myself is. One thing that Frankie said that I think is really powerful is you just think about the time you have. And I'm working with a company where I didn't realize how many time zones they were across. The only time synchronously they have is totally absurd time slot, it's like eight to 10:00 AM Eastern time, which is crappy for Singapore and awful for the West Coast people but tolerable for everyone.

Daniel Stillman:

It's hard because I don't know if we can get the best work out of everybody synchronously in those two hours, given everybody's condition. Frankie was in person, so he was able to do a different thing. The question of how many questions we can actually address in these more collaborative, complexity minded ways is... This is not a 30 minute standup where you're like, "Okay, here are these five things, bang, bang, bang, how are you doing with that Kate? How are you doing with that Kyle? Okay. Good, great. Next, next, next."

Daniel Stillman:

In 90 minutes Kate, you got to the beginning. I think a lot of times this is where I think the law of subtraction is always a helpful thing with your agendas to say, like take something out. Because while we underestimate people's capacity to deal with complexity, I think we overestimate sometimes our ability to get them through an extraordinary amount of stuff in a very short period of time.

Kate Farnady:

Totally. I will say that meeting was across four GOS.

Erica O'Donnell:

Yeah. I think that's a huge consideration is the amount of time you have and then number of people. And I think this is something I really learned in the masterclass with all of you was, the more attendees the less time each person gets to speak. And so, there's this, we're talking about the arc but also we're talking about how many people, how much time? Those constraints are very real and they really impact what you can do with that middle part of the agenda.

Erica O'Donnell:

Sometimes you have infinite time, if you're talking about large systems thinking, network type level stuff, and other times you really have big constraints and those can make a big difference. I don't have a great anecdote for you guys that's easy to jump into, mine's a little complex. I was just going to get super tactical as is my want and talk about how for me, when I'm designing an agenda, it's really easy to start from the beginning and go to the end. Like what are we going to do first? What are we going to do second? I really try to not do that.

Erica O'Donnell:

I often start at the end, I think about what is it that we're trying to achieve? I ask self questions like, what decisions are we going to make next? How is the product of this going to be used? What questions do we need to answer? Then I can kind of work back. Maybe it's not even the back but it's that messy middle is where I start, and then I layer in a close talking about that. How are we moving this into the next thing? What ever that's another session or something else.

Erica O'Donnell:

Then I think about a warmup or an activator, or an eye opener which a lot of times we might start there. But why I do that is because then I can say, what part of my everyone's brain are we trying to activate? What types of collaborative conversations are we having? If it's a connecting agenda where we're really trying to establish relationships, maybe we start with some appreciative inquiry, where two people are talking to each other about a positive experience and they're creating that dynamic.

Erica O'Donnell:

If it's a creating agenda, maybe it will do a quick draw me a picture just to get people in this idea of like a sketch doesn't have to be perfect, and you have 10 seconds to draw a picture. That's super tactical but just a way to bookend to say, we spent a lot of time talking about that middle, but there's always those really important open that set the stage and the close of moving this conversation forward.

Daniel Stillman:

Well, just to like really, really double stitch for you the close isn't just, what do we want to end? What's the product we want to have in our hand? It's how the close becomes a springboard for the open,-

Erica O'Donnell:

Yes.

Daniel Stillman:

... right?

Erica O'Donnell:

Yes.

Daniel Stillman:

How will that get me momentum on this much bigger arc that I'm holding in my mind? And this is where the big arc, little arc method for me. It's not this open and close, it's like the next open and close and it's part of a much bigger, you're in service of a much bigger vision for them. Also I want acknowledge, it's the limit of the time we said we... I obviously have no place else to go but hang out with you guys. But I will ask people to check out. If you can stay a little longer, we'll wrap up whatever threads. Erica, I appreciate you going super tactical. And-

Kyle Pearce:

Yes.

Daniel Stillman:

... as far as secret sauce, years later when people have come to a facilitation workshop of mine, open exploring close, it's like the only thing they remember. Because it's everything, it's the whole thing. And I love this idea of what the close really means. Like you have a very, very deep understanding of why the close is important. And I love that. That's my checkout.

Erica O'Donnell:

Thank you-

Daniel Stillman:

I will pass them out. Erica, if there's anything extra you wanted to say. Also Kate, I know you had to go on time as well. But thank you. Thank you everyone for this conversation.

Erica O'Donnell:

Yeah. Thank you Daniel. I, I think I definitely took a few things away from the conversation. I love Frankie's idea of leaning on other collaborators to own the outcome and own even in the process. That's a great takeaway. And for me, embracing messiness is always a struggle, a difficult thing for me so Kate's story gave me anxiety. But in a good way to remember that these things are messy. That humans are not linear and perfectly structured. So appreciate the conversation as always.

Daniel Stillman:

Erica, I'll just say humans are the definition of nonlinear. When I try to explain nonlinearity to people in complexity. If you tell someone to calm down and they get more angry, that is the definition of nonlinear.

Erica O'Donnell:

Yeah. Absolutely.

Daniel Stillman:

Like, "Hey, calm down." And they become 20 times more angry. That is a non-linear response to stimulus.

Erica O'Donnell:

Oh yes. I have a six-year-old. I'm very familiar with that reaction.

Daniel Stillman:

Amazing. Who else has something they're checking out with?

Kyle Pearce:

I'll go. There's so much to, to grasp on to here. But one of the things I'm going away with is a little drawing in my notebook where we had talked about these different types of meetings, the different levels of benefit that a meeting can bring. And I was just reflecting on how my meetings, I'm usually bouncing up and down from the spiritual to the learning too et cetera, et cetera. This has made me think in a much more zen-like way about really there's four lines or five lines that are going through. And what we really need to do is touch on all of them, and give an opportunity for all of them to be expressed. So gratitude to all of you for this conversation. Thank you.

Daniel Stillman:

Thank you Kyle. Frankie, Kate.

Frankie Iturbe:

Yeah. [crosstalk 00:49:56]. Did you want [crosstalk 00:49:57] to go Kate? Go ahead.

Kate Farnady:

Yeah. I'll just be quick because I do have to go and I'm cheating on my other meeting for you guys [inaudible 00:50:06] fight about. One of the things I love about these sessions with you Daniel is it always, always illustrates the wild diversity of the facilitation program and the different approaches. I loved hearing Erica's approach. I learned from everybody. And it just reminds me about what a challenge it is to do this work and how we bring such different approaches. I don't know. It fills me up to see and hear about other people's approaches. I love it. So thank you.

Daniel Stillman:

Thank you Kate. I really appreciate you bringing in the norming, storming performing. It's like I'm these three layers of the four types of agendas, opening, exploring and closing. And then where they are in their evolution as a team are three things that I'm holding in as a really interesting takeaways.

Kate Farnady:

I have to say like one last little a bit is that this actually the chaos approach was really right on. I had a gut instinct about it when I went into it, but it was right on for where this team was in its formation. I think it helped progress that in its open endedness. That was not really by design for the start.

Daniel Stillman:

But it can be next time. Kate, don't cheat on your meeting for too much longer. And Frankie, let's give the mic over to you. Then obviously I know people have other places to be. I'm so grateful for this conversation. Frankie, what are you taking away from this conversation?

Frankie Iturbe:

The item I want to check out with Daniel, Kate, Erica, and Kyle here is an expansion of a mental model I use for my workshop. Often I try to think about my workshops or meetings and outcomes, inputs and outputs. I think Erica helped me build on that as what she was sharing. I think outputs, we typically think, especially in the product world, you think of that as a working prototype or a product.

Frankie Iturbe:

But I like that Erica mentioned you could end at, what questions will we have at the end of this meeting or this workshop, or this sprint, whatever we're doing, right? I think it's just really important, I'm taking that away to be at peace and be okay with hey, my output again doesn't need to be a working prototype. It can be a set of questions that we're then going to go tackle next time we meet, next time we gather.

Daniel Stillman:

That's awesome. The inputs and outputs is like such a powerful question but then the question is like and then what are the outputs for, right? But that is the outcomes. Tell me more about this insight. How does this evolve your model for you?

Frankie Iturbe:

I just feel like one growth that for me was realizing so again, working in a space where it's not within sales org, it's not always so product driven. We're not delivering a specific product. It took me a while to adopt like, okay. An output can be a useful value, output can be this new org structure. It doesn't need to be something tangible in our systems yet. But the way that it evolved for me with Erica's comments was, what did I write down exactly in my notes?

Frankie Iturbe:

I also wrote, what decisions are we going to make next? Like we finished this work and then what decisions will we be able to make with this? It kind of goes back, actually, it's getting very meta here Daniel. It becomes an input to your point. I think that might have been what you were saying when you asked me the questions. Sorry if I misunderstood. But those set of questions, those decisions you can now go make become your inputs for the next iterations that you're going through.

Daniel Stillman:

Yeah. That's awesome and really powerful. Thanks for that Frankie. And thanks to everyone for being so open and generous with your process and your wisdom. Kate had to hop and it's time for everyone to hop. But I appreciate you making time for this conversation. This is great.

Erica O'Donnell:

Well, thanks so much for including me down and Frankie, Kyle, Kate. It was a real pleasure to chat with you and to meet you Frankie for the first time. So I'll, hopefully will see you again at another Conversation Factory, conversation.

Daniel Stillman:

Frankie doesn't know this, but I want to rope him into a facilitation Friday. He did an amazing session during the last master class where he facilitated something boring and on purpose. It's something that, we're talking about powerful agendas and deep transformation and he was trying to answer the question. How do I motivate a group of people to just get through some boring shit that we got to talk about?

Erica O'Donnell:

To go through a spreadsheet? How do you get through that? How do you power people through that? That was a fun one. [crosstalk 00:55:12]-

Daniel Stillman:

It is. It was a great prompt. I think it was a really fun exercise too. And so, no spoilers. But I think it's an inverse and maybe a more common challenge of like okay, everyone gathering tasks and assigning tasks.

Erica O'Donnell:

Yeah. Like building product backlogs or something collaboratively, it's just painful writing collaboratively writing user stories and everyone just wants to not be there. I hear you. These are challenges that are... I love it. I want to come to that session and Frankie.

Daniel Stillman:

Well, maybe afterwards.

Kyle Pearce:

I'm up for Daniel. I'm up for it.

Daniel Stillman:

Maybe after the session Erica, you and Frankie and I can debrief what wisdom you derived from it. Because I think there's a lot to be said about how to take the everyday stuff we do, and somehow still make it deeply engaging.

Frankie Iturbe:

Indeed, indeed. I just want to echo back Erica's comments back to her as well, and to Kyle and to Kate pleasure, meeting you all as well. Learned so much in an hour probably saw me taking, I'm an avid, taking copious notes and just learned a lot from you all. Definitely look forward to learning more from you all in the future.

Daniel Stillman:

Awesome. Thank you. Kyle, you had one more thing on the tip of your tongue.

Kyle Pearce:

It just all bounces around. Beautiful. Nice to meet you Frank. Daniel, thanks for looping me in on this one. Glad to participate. And Erica, great to see you again.

Daniel Stillman:

Frankie I want your notes. They may make it into my show notes.

Frankie Iturbe:

They're not as cool as like, I'm sure the sketches that you have Daniel but-

Daniel Stillman:

They'll make it into OneNote and then they'll be much, much better. All right, I'm going to call scene and stop recording and release you all from...

Communities are Conversations

I'm thrilled to be able to share this conversation with Carrie Melissa Jones with you! Carrie is the co-author of Building Brand Communities, with Charles Vogl, and she's kind of a big deal in the community-building world. She's also an alum of the facilitation masterclass and a friend. 

In this wide-ranging conversation, we dig deep on the subject of community as a conversation. As Carrie says, every community starts with a conversation, and conversations are what sustain communities and hold them together.

Some of what we cover in this 3-part episode:

  • What community really is, and how organizations get it wrong

  • The power of online relationships and how they can help us

  • How the community-builder affects the community

  • The inner work that goes along with community building, and how that affects brand communities

  • The conversation that launched a book - the story of Building Brand Communities

  • The difference between meaningful engagement and empty engagement

  • Why brand communities? What role do they play in rebuilding our social fabric?

  • How modern community-building efforts are still being shaped by outdated ideas

Part 1:

Part 2:

Part 3:

Links, Quotes, Notes, and Resources

Carrie's Website

Podcast episode: Being a Beginner is Often the Key We Need for Empathy and Creativity

Building Brand Communities, by Carrie Melissa Jones and Charles H. Vogl

The Power of Ritual with Casper ter Kuile

Minute 5

So I know that is possible to create long-lasting lifelong friendships through the internet. And that's basically what my drive to do this all day every day is, I know we can create meaningful relationships that sustain us that actually regenerate much of what's been lost of our social fabric and you know, through disconnection and technology and all that, we can regenerate it, but it's going to take massive culture level change. So right now I do that for organization. I hope to be able to expand that out and really be part of this culture level change over the long term as well.

Minute 9

And this is an evolving answer but I actually think that a lot of the reason for our disconnection and alienation and isolation from one another is economically created and was accelerated during the industrial revolution. So I work with organizations specifically because I see them as one of the root problems in our society causing this disconnection. And so if organizations are continually going out using the word community, which many of them are just using it, willy nilly, and then not backing it up with actions. What that does is it creates, it just wipes out what actually I've heard Casper say, community washing is what a lot of organizations do.

And at the organizational level, it means that they're not actually following up on what they're doing, or what they're saying with actions, because they're not working in integrity.

Minute 17

Organizations to me are one of the top culprits of like doing this wrong and creating some major, major issues. And I've worked with a variety of organizations, some of which are completely humble about this fact. And they say, "we want to do better." And then I've worked with really large organizations who one time a VP at the end of a four hour workshop said to me, "this is really nice and all but we're not going to do anything with this."

So she came to me in my program and said, "Carrie, unfortunately, I lost my job in the pandemic, but this is something I really want to build up my skills around online community building. I don't want you to give it to me for free. I want to be an investment. And what do you think about work study?" And I thought about the times when I used to do yoga in person, and there was always work study opportunities at my yoga studio. Anyone could come in and offer their services for free yoga classes. And so I thought, yeah we'll do that. I'll just make like a little yoga studio

Out of this. And with her, it was an organic process of, figuring out what do you want to do? Like what do you want to do with your life, your work, and how can I give things away for you to take on, to build up your skills? And now I have four different work study students. So I actually made it part of the process. And I think it's really important that I put that work study out there. Just like you put your scholarships out there because it's an issue of equity if we just keep it secret, like oh yeah if you ask me, I might give you a discount.

Minute 26

Daniel Stillman:

I was thinking about the places and spaces and the mechanics, but I really like that you went to the inner move or the inner move of being open. Being present and being aware of reciprocity. Which is, you can go to all the places and spaces, but if you don't have the inner move, then you're not going to be able to take advantage of it.

Carrie Melissa Jones:

Yeah. I think that's something I realized too, in the last few years. Because, in the past I might have said, "Yeah, well you go to Facebook groups." And then you go and here's all these tactical things. I can tell you, none of that matters. In fact, none of it matters. I think it surprises my clients because they realize that they must change in order to build community. And that's pretty huge.

Minute 36

Daniel Stillman:

but I think what's interesting here is, the question I was sitting with was, well, what's the most important conversation that the brand community isn't having and that you want to invite? And it seems like I'm wondering what the shadow is. And I'm seeing that that is of great interest to you. What aren't we talking about? What aren't we looking at is really important.

Carrie Melissa Jones:

I think that's what people aren't talking about is the inner work that it requires and the fact that it... Whatever issues you have around being in relationship with others, if you plan to build a community that issue is going to come up. So who you are is going to either accelerate or inhibit the community that you're able to build.

More About Carrie Melissa

Online community has helped me through some of the most challenging times in my life.

As a lonely, depressed and awkward teen, I discovered online communities as one of the only places where I could be seen, appreciated, and cared for by total strangers — who then became my friends. It was in virtual spaces that I first found confidence and acceptance. Over time, I was able to bridge the gap and bring that confidence into my “offline world.”

Online community started it all.

I credit these early experiences for laying the foundation for my skills leading communities. Every day, I see online spaces tearing people apart. I know we can do better, and I know the difference between genuine, meaningful community and community with no soul and center.

As the founder of Gather Community Consulting, I consult with brands and community leaders to build successful online communities. I am also a speaker and educator on the topic of online communities, community-based movements, and community leadership.

Prior to founding Gather, I was the Founding Partner and COO for CMX Media (acquired by Bevy Labs), a unique “community of community builders” that provided training, events, and programs for community builders around the world. I got my professional start in community management in roles with Socratic (AI-based education app), Scribd (online library), and Chegg (online book rentals).

In 2016, I was named by Salesforce as one of three experts to follow in community management, and my writing on communities has appeared in Venture Beat, Convince and Convert, The Next Web, First Round Review, and Creator by WeWork.

In addition to being passionate about helping organizations build communities, I’m a passionate advocate for community leaders.

I’m a graduate of UCLA and have done volunteer work for Young Women Empowered, Indivisible Washington, Emerge America, and Feeding America. I am currently an M.A. student at the University of Wisconsin-Milwaukee, studying online communities and well-being.

Full Transcript

Daniel Stillman:

Well, then I'll officially welcome you to the conversation factory. Oh my God. It's really happening. It's you it's me.

Carrie Melissa Jones:

I'm so excited.

Daniel Stillman:

We're breaking the sixth wall, Carrie. You are. I love that you actually go for walks with a podcast. Where do you walk when you walk?

Carrie Melissa Jones:

I walk in Milwaukee. So I, Milwaukee. Yeah, I had to. Yeah, so I live about two blocks from Lake Michigan and I walk not, the exact same path every day, but close to it. And so I walk along, it's called Lake Park. It's actually where I got married last year. And so I look at that almost every day, like where we got married in the park and walk across the couple bridges, walk by a country club, walk under like, yeah. It's really beautiful and cold right now. Freezing.

Daniel Stillman:

Congratulations. I don't think I knew that you got married last year.

Carrie Melissa Jones:

Yeah, yeah.

Daniel Stillman:

I should have, I should have you were asking me about my honeymoon, which apparently I dropped lots of mentions of apparently.

Carrie Melissa Jones:

No, I was just, I knew you did something fun in 2021, which we all needed to do something fun, but yeah, I got married with three different ceremonies last year, so yeah.

Daniel Stillman:

What were the three ceremonies for?

Carrie Melissa Jones:

Well, pandemic related. I never would've. We never would've done that prior. The first one was legally. I didn't realize that getting married, you had to legally sign paperwork sometimes before, sometimes after the ceremony. Yeah. So because the courthouse was shut down in Milwaukee, you couldn't go and just get a judge to sign it. So we said, if we have to get this done, like we have to get someone to officiate for us. Like we might as well just make it a thing and let's just have a ton of fun. So we got married in the park and then went to our favorite restaurant and it was like, we just had a little private area. Then we did our vows and stuff in Colorado on the top of a mountain at sunrise. And then we did.

Daniel Stillman:

I do remember you talking about that. That sounds, so fun.

Carrie Melissa Jones:

Yeah, it was amazing with some of our best friends from childhood and his from way back and then had a party with family. So my parents were not, and his parents were not involved in either previous ceremonies, which they brought up many times. Yeah. So we did a giant party at my parents' home in east Tennessee and my dad and my family formed a family band. And they were like the music for the event.

Daniel Stillman:

That is so nice.

Carrie Melissa Jones:

Yeah. Yeah. It was very cute.

Daniel Stillman:

And you get to, when you go on your walk, there's this touchstone that just brings it all back for you.

Carrie Melissa Jones:

Mm-hmm (affirmative). You see it change throughout the year, which I think is one of the most amazing things. If, you go to the same place in nature.

Daniel Stillman:

Yes.

Carrie Melissa Jones:

Every day you see it through summer and winter it's just very humbling to see that happen, that change.

Daniel Stillman:

For me. I always, when I go for a hike and I see like a waterfall, I think to myself, this is always here.

Carrie Melissa Jones:

Yeah.

Daniel Stillman:

Even though I'm in my house, I can't hear or see the waterfall. It's just there.

Carrie Melissa Jones:

Absolutely. Absolutely. I backpack a lot and went on a week-long trip in the Sierra's a few years ago with my dad, my brother and my partner. And we went to Thousand lakes in California. I think you can drive up near it, and I've had the exact same thought we saw it and it was just the most beautiful thing I'd ever seen. It took us seven days to get there and I just thought this is available to me at any time. But I stare at computers a lot and this is always here.

Daniel Stillman:

Yeah. Well that's, this is, this is a fine transition. You know, when you say, what do you do to someone and you're like, well, I look at computers all day long and that would be very nonspecific because like, and I write emails. I look at things.

Carrie Melissa Jones:

Yeah.

Daniel Stillman:

I, my friend Carl once sent me a mockup of a children's book. I think it's Richard Scarry, there are these little like anthropomorphic animals just going and the title of the book was remade to say "Documents". That's all we do now is "Documents". It just people, "Documents". So the better question, and this was actually the first question I had on my list was I wanted to try this one out, which is why do you do what you do?

Carrie Melissa Jones:

Hmm. Yeah. Why do I spend all that time? Staring at computers versus yeah. Staring at lakes. So why do I do what I do? So I build online communities with organizations and I didn't know that was a job, frankly. It wasn't a job actually for most of history. And I actually grew up being a super awkward, extremely shy kid. I had friends, but I was just very closed off. There was like a pane of glass between us. Right. And I really just didn't feel known or seen by anyone in my life. And when I was about, 14, 15, my dad gave me, I grew up in Silicon Valley, and my dad gave me this hand-me-down computer. That was like third, the one last in line that was like falling apart. And he said you can have this one. And I discovered forums.

Carrie Melissa Jones:

I discovered music forums primarily and found that I could create all kinds of incredible relationships with people. I could explore my identity, explore who I was, explore what mattered to me. And I really finally opened up to people on the internet before I ever did in real life.

Daniel Stillman:

Yeah.

Carrie Melissa Jones:

So I know that is possible to create long-lasting lifelong friendships through the internet. And that's basically what my drive to do this all day every day is, I know we can create meaningful relationships that sustain us that actually regenerate much of what's been lost of our social fabric and you know, through disconnection and technology and all that, we can regenerate it, but it's going to take massive culture level change. So right now I do that for organization. I hope to be able to expand that out and really be part of this culture level change over the long term as well.

Daniel Stillman:

And for people who don't know, I think I actually learned this statistic from Casper ter Kuile and his book about ritual. I think it was like, if you ask the average American, how many friends they have, or how many people they can call on when there's something going poorly in their lives, it's like three people and, or, or I think it's like two and it was three in 1980, whatever. And, and our conversation together, I was like, oh my God, everybody in America just like lost a friend in the last decade, like we had very few and now we have like barely any.

Carrie Melissa Jones:

Yeah. And it's two in five Americans, specifically, don't have anyone to go to in times of need. And I think about that all the time, because that statistic feels like really abstract and far away from me.

Daniel Stillman:

Yeah.

Carrie Melissa Jones:

Because I now have very close friends and family people who I can go to in my times of need and I have gone to in my times of need. And so it is personally hard for me to imagine, that, but I know it's all around me. And in fact, I did a research study in graduate school last year. And we asked people about their connections during the pandemic and the statistic held true even among, it was a convenient sample, of most of my friends who are community builders. In aggregate about 20% of them had no one to go to in their times of need. And it just, I think about that, I actually know those people.

Daniel Stillman:

Yeah.

Carrie Melissa Jones:

It just breaks my heart,

Daniel Stillman:

It's insane. So, but here's the thing. And so the first big chunk I wanted to look at is, so this is why you do what you do.

Carrie Melissa Jones:

Mm-hmm (affirmative).

Daniel Stillman:

In the broadest sense, but you could go do this for a brand. Right. But instead you are. I mean, for people who don't know, who are listening in Carries kind of a big deal, right, in this thing that you do. But you are, and you don't just do it for one company. You do it for lots of companies and that's a choice that you've made. And so I'm really curious because I make that choice too. I'm like, why do I do what I do? So if you take the same question and reframe it as a bewilderment.

Carrie Melissa Jones:

Yeah.

Daniel Stillman:

You know, I'm really curious about like why you're a, whatever you'd call it a Paladin, a consultant.

Carrie Melissa Jones:

Yeah. Yeah. I call myself a strategist or consultant. That's a such a good question. And one that frankly, I have wrestled with my entire career. It's like, why don't I just go and like teach people the skills individually, like how to be a better person on the internet. Cause I definitely can.

Daniel Stillman:

Just one at a time, don't be a troll, but you also teach cohorts of people how to do what you do and not everybody wants to do. So you were driven to have a whole business where you educate people and you work with many different types of companies instead of just, I don't know, going to build community at, fill in the blank, tech company.

Carrie Melissa Jones:

Yeah. Which, I did I started my career doing it in tech companies actually. And this is what I've kind of landed on for now. And this is an evolving answer but I actually think that a lot of the reason for our disconnection and alienation and isolation from one another is economically created and was accelerated during the industrial revolution. So I work with organizations specifically because I see them as one of the root problems in our society causing this disconnection. And so if organizations are continually going out using the word community, which many of them are just using it, willy nilly, and then not backing it up with actions. What that does is it creates, it just wipes out what actually I've heard Casper say, community washing is what a lot of organizations do.

Daniel Stillman:

Yeah.

Carrie Melissa Jones:

And at the organizational level, it means that they're not actually following up on what they're doing, or what they're saying with actions, because they're not working in integrity.

Carrie Melissa Jones:

And then at the individual level, we come to expect community from things that are not community at all. They're just audiences or one conference that a company put on and they're calling that community. And then we don't realize what we're missing, because that's what we think community is.

Daniel Stillman:

Yeah.

Carrie Melissa Jones:

Organizations to me are one of the top culprits of like doing this wrong and creating some major, major issues. And I've worked with a variety of organizations, some of which are completely humble about this fact. And they say, "we want to do better." And then I've worked with really large organizations who one time a VP at the end of a four hour workshop said to me, "this is really nice and all but we're not going to do anything with this."

Daniel Stillman:

Mm-hmm (affirmative).

Carrie Melissa Jones:

I had flown across the country to, for her to tell me this. And yeah, it's just some people get it, and some people don't and it's a continual practice.

Daniel Stillman:

Yeah. I'm wondering how you, how you sustain yourself in, emotionally sustain yourself. I think this is one of the challenges of being a consultant is some clients really care and some clients are trying to do what I would call edutainment when they bring me in sometimes. And, I'm guessing the question I have is like, what's the conversation you're having with yourself about your business?

Carrie Melissa Jones:

That's a really good question. I am continually just trying to be aware of my capacity. And I often go over it, even with that awareness because doing this work requires empathy, just such deep levels of empathy that I can lose myself really easily in it. Cause I'm empathetic for the various stakeholders within the organization. Sometimes I'm very intuitive and I can feel sometimes people's trauma. I know that sounds really wild, but I feel them bringing it into the conversation. I'm sure you can sense all kinds of stuff like that.

Daniel Stillman:

Yeah, people are so traumatized. I mean, let's just, I mean, obviously the last 3 years, but let's just talk about, the last 100 as you said, right. Being totally uprooted from what kind of lifestyle we're perhaps built to do. Right. There's a lot of traumas.

Carrie Melissa Jones:

Yeah. Yes, absolutely in the last three years, but even prior to that, there's just so much that goes on in organizations that people don't process and it becomes these scar tissue and they build from places of ego and trying to heal things.

Daniel Stillman:

Yeah.

Carrie Melissa Jones:

And I only know this because I have my own story of trying to do that right. It takes empathy on that level and then empathy on the customer or whoever we're gathering at that level deep empathy there. So I have to do less than I think I'm capable of. And I'm actually finding that year after year, I'm doing less work every year but I'm doing it better, if that makes sense.

Daniel Stillman:

It does. Yeah.

Carrie Melissa Jones:

Yeah. Yeah.

Daniel Stillman:

The word capacity is so fascinating. One of the things I actually was really interested to talk to you about, I was super grateful for the folks you sent over for the scholarships for the master class. And I was like, wait, Carrie's got this whole like work study machine underneath the hood. You talk about capacity, and I was like how does she structure the innards of this business? You seem to be, have a little minion.

Carrie Melissa Jones:

Minions?!

Daniel Stillman:

I myself am good at just sort of like emergently, discovering all the things that need to get done and then just kind of doing them and then always remembering that there's something else that I've forgotten to do. I'm only just now learning how to explain what I intend to do and work with other people to help extend my capacity. I, it's a thing, I get it.

Carrie Melissa Jones:

Yeah.

Daniel Stillman:

I've never had to do that. You seem to have some of that a little bit more at your fingertips. So tell me about that, Carrie.

Carrie Melissa Jones:

That's so interesting that you would say that because I feel like I'm so bad at it. In fact, I feel that I'm, again, aware that this is an issue and so I bring it up with everyone that I work with. I say I'm really bad at receiving support. I'm not good at it because I'm used to being self-sufficient, I grew up and I solved my own problems. I got A's on my own.

Daniel Stillman:

Damn straight you did. Why was that important to you to be self-sufficient do you think?

Carrie Melissa Jones:

Oh, you want to, are you my therapist?

Daniel Stillman:

Sorry. I was that, I'm always, this is my mode. Whatever's, I'll take that back.

Carrie Melissa Jones:

It's totally challenging me. I mean that with love. It's a very deep question.

Daniel Stillman:

Yeah.

Carrie Melissa Jones:

I do that because it was a form of safety for me growing up, and I knew I couldn't depend on anybody else, but I could depend on myself.

Daniel Stillman:

Yeah.

Carrie Melissa Jones:

And that makes for a very strong person, right, like extremely resilient.

Daniel Stillman:

Yeah.

Carrie Melissa Jones:

And that's something I'm just aware, like whatever comes my way, I can deal with it, I know. My issue is that I then try to help other people on the path, so I'm always giving and often not receiving. And so a lot of community builders are that way. So I see it a lot in my work. And we often feel like we don't have a choice. We're like, I did this to myself. Like I've taken on these responsibilities, I can't ask anyone for help because I said, yes. So now I have to deal with it. I don't think that's true. I think it's a thing where people want to help us.

Daniel Stillman:

Yeah.

Carrie Melissa Jones:

They really really want to help us.

Daniel Stillman:

And so this is clearly an edge for you and your working.

Carrie Melissa Jones:

Oh Yeah. The people that you spoke to that I referred your way, both brilliant community builders, actually one of them came up with the idea of the work study program. So she came to me in my program and said, "Carrie, unfortunately, I lost my job in the pandemic, but this is something I really want to build up my skills around online community building. I don't want you to give it to me for free. I want to be an investment. And what do you think about work study?" And I thought about the times when I used to do yoga in person, and there was always work study opportunities at my yoga studio. Anyone could come in and offer their services for free yoga classes. And so I thought, yeah we'll do that. I'll just make like a little yoga studio

Carrie Melissa Jones:

Out of this. And with her, it was an organic process of, figuring out what do you want to do? Like what do you want to do with your life, your work, and how can I give things away for you to take on, to build up your skills? And now I have four different work study students. So I actually made it part of the process. And I think it's really important that I put that work study out there. Just like you put your scholarships out there because it's an issue of equity if we just keep it secret, like oh yeah if you ask me, I might give you a discount.

Carrie Melissa Jones:

That's an issue of equity and privilege and it just causes all kinds of problems. So I was public about it. I brought on 4 work study students, and now I have a whole, I just wrote down all the things that I do and thought, what do I not need to be doing myself anymore? Yeah. That would teach someone else. Something I think is really easy to do that for them is an edge. And I meet with them once a week. I make sure that they're getting something out of it. So I mentor them all and we're just in a continual conversation and they all know I'm bad at receiving. So I say that to them, every time I give them something, I'm like, don't let me take this back from you.

Daniel Stillman:

That's wonderful. And that feels so normalizing to me, because I feel like I've expressed to people like, I don't know how to do this. I don't know how to do all the things that I'm doing. I recently just documented my process for the podcast. I brought on a process coach, Srinivas Rao, who's going is, I recorded his podcast. He has a podcast called the Unmistakable Creative.

Carrie Melissa Jones:

Oh yeah.

Daniel Stillman:

And so he does knowledge management consulting. And I mapped out the whole podcast process and there was like this little swirl towards the end I knew about. And I was like, I have to do all this. And, Nathan who will listen to this, hi Nathan, who's my podcast producer assistant right hand guy, looked at the diagram I made in braille. Cause I sent it to Nathan before I sent it to Srinivas, and I was like, Hey, did I miss anything? And he was like, no, that looks about right. He's like, but that little swirl there, I can do that if you want. He's like, you just have to probably give me your login for those two, that site and that other site. And I was like, really?

Carrie Melissa Jones:

Yeah.

Daniel Stillman:

I can just, I don't have to do that.

Carrie Melissa Jones:

Yeah. That's great.

Daniel Stillman:

And it's all also something that he, not that I don't think that's like, that's not his edge. That's not where his joy is. We, it's my job to find other things that are worthwhile and interesting for him to do so that it matters to him and he doesn't go away.

Carrie Melissa Jones:

Yeah. And then we also have to trust that people will say no, if they yes are at their capacity, we can't decide that for them ahead of time.

Daniel Stillman:

Yeah.

Carrie Melissa Jones:

That's not really fair. Yeah. And I get quite emotional about actually, like I brought on an assistant this last year and she's, she's so good. She doesn't even wait till I delegate things. She's like stop doing that thing. She's like, I guess this is exactly what I need. Thank you Jen. Yeah. But it makes me like emotional I'm even like tearing up about because to be supported in that way is so fresh for me. It's so new and it feels very healing, frankly.

Daniel Stillman:

Yeah. This is the conversation you're having with yourself about your business. Like what is mine to do? What is some, what can someone else help with help me with, do I have to be doing this? And I love that you've bringing in, you're bringing in somebody who can challenge you and say, put that down and walk away.

Carrie Melissa Jones:

Yeah. She's been doing this for like 20 years. So she's just like, why are you still doing all these things in your business? This will stop from growing. I've seen it over and over again.

Daniel Stillman:

The same thing for myself I've just noticed that talking to someone who's been doing it for 20 years, showing my process to Srinivas, who has a much more successful podcast than I do. I didn't actually feel any shame. Cause I was like, I'm clearly have hacked this together. You tell me, but there can be a lot of shame. I found of just like, I don't know how to do this. And I'm broken because I don't. So I'm, it's actually really, I'm normalizing for me. Thank you for thanks for engaging this conversation.

Carrie Melissa Jones:

Yeah, Absolutely. Yeah.

Daniel Stillman:

I am really curious. The, sort of like bow to, there was two more things about you that I wanted to plug away at. One is how you build your own community and mentorship. Because obviously you mentioned the community, people who have no community. And I feel like that's something you must be working at intently. How do you build that for yourself?

Carrie Melissa Jones:

Yeah. For me it started in late high school that I.

Carrie Melissa Jones:

... started in late high school that I left the music forums, where I was a member for a long time and had learned all these social skills that I didn't have. And part of the reason I was able to leave and still feel connected to people was because of my very best friend still to this day, Samantha. And she came to me in her time of need and showed me what it looks like to ask for support when we were quite young.

Carrie Melissa Jones:

And so she's been my best friend through our entire lives at this point. Almost. Knowing that she's there is like this foundation that I then have of like, she's my safety foundation. Like, I don't know what's going to happen in my life, but Sam is there. And that's been really big for me.

Carrie Melissa Jones:

And the other thing is, again, something I'm not super good at, but making sure that I disclose information about myself and what's going on with me when someone else discloses this principle of reciprocity, which is like this human beings just want to be in reciprocal relationship with one another. But oftentimes I would listen to other people's problems, and then I would just not share anything going on with me, which of course you're like, moving along and developing a relationship and that just stops it from progressing.

Carrie Melissa Jones:

So, there's also times you don't have to share your story with anybody. You don't owe it to anybody, but if you feel safe with someone and you want to become better friends with them, you will have to share part of yourself with them. So there's no holding that back if you want to be close with someone in your life.

Daniel Stillman:

So it sounds like there's an inner move that you're focusing on. That some of your work is to make sure that you are actually being vulnerable.

Carrie Melissa Jones:

Mm-hmm (affirmative).

Daniel Stillman:

With the right circle of people.

Carrie Melissa Jones:

Exactly.

Daniel Stillman:

Yeah. The safe place.

Carrie Melissa Jones:

Exactly. Because I will say, actually up to my late twenties, I had a lot of messy things going on in my life. And I definitely opened up to the people who retraumatized me. That's what we do, right? When we've experienced personal trauma, we just recreated it until we heal it. And so, you can certainly think someone's safe, who actually ends up not being safe to share things with.

Carrie Melissa Jones:

And so I think again, normalizing the fact that sometimes you're going to open up to people and they're not going to be good about it. And they might hurt you. And you might hurt them. And your relationship might not last forever. All that is just part of it. You cannot go through this life and not be hurt at some point. Like, you're not living. So I think coming to terms with that is deep work to do.

Daniel Stillman:

Yeah. That's really powerful. I think it's funny. I was thinking about the places and spaces and the mechanics, but I really like that you went to the inner move or the inner move of being open. Being present and being aware of reciprocity. Which is, you can go to all the places and spaces, but if you don't have the inner move, then you're not going to be able to take advantage of it.

Carrie Melissa Jones:

Yeah. I think that's something I realized too, in the last few years. Because, in the past I might have said, "Yeah, well you go to Facebook groups." And then you go and here's all these tactical things. I can tell you, none of that matters. In fact, none of it matters. I think it surprises my clients because they realize that they must change in order to build community. And that's pretty huge.

Daniel Stillman:

That is pretty huge. And it's very clear to me and we'll transition in a moment to talking about brand communities. It is a spiritual path for you. That it matters deeply because it's part of your core identity.

Carrie Melissa Jones:

Mmm.

Daniel Stillman:

But I feel like I would be remise. The last thing we did together, the last time we hung out was this experimental online book swap. And I didn't realize. I think I learned from the interview you did with Charles. Was about, that you've been passionate about books since you were a teen.

Daniel Stillman:

And I'm really curious for you to talk about, because the community, we think like, "Oh, it's people and divulging." But a book is the safest trend.

Carrie Melissa Jones:

Oh, I know.

Daniel Stillman:

Right?

Carrie Melissa Jones:

I love books.

Daniel Stillman:

Yeah. So I'm curious, how do you feed your head and what books have nourished you and are nourishing you? I probably won't do anything with this video, but there on that bookshelf behind-

Carrie Melissa Jones:

Yeah. There's behind me-

Daniel Stillman:

[inaudible 00:28:02] Jones. Our books.

Carrie Melissa Jones:

I have a book shelf over there, bookshelf downstairs. I read all the time. I read a lot less fiction than I used to. But growing up, well actually in college I studied English literature and I studied abroad in Stratford-upon-Avon in London. I saw the real Shakespeare group.

Daniel Stillman:

Wow. That's amazing.

Carrie Melissa Jones:

It was so cool. James Franco was in my class. I don't have to talk about that right now, but.

Daniel Stillman:

No. Let's get read of that.

Carrie Melissa Jones:

So, I have been escaping I think through literature for a long time. Growing up, my favorite author was William Faulkner. So I was always very dark and wanted to explore the shadow sides of things and find poetry in the attempts to have language express what our world is and what our identities are. But constant failure.

Carrie Melissa Jones:

I actually have a tattoo on my arm that says, "I'll do what little I can in writing." Which is from a book by James Agee, who's from East Tennessee, where my family is from.

Daniel Stillman:

Wait, can you say that quote one more time? I went by fast.

Carrie Melissa Jones:

I'll do what little I can in writing.

Daniel Stillman:

Tell me what that means to you. That's so interesting.

Carrie Melissa Jones:

Yeah. So in the 1920s, there's a history. In the 1920s in America during the Great Depression, the south was obviously hit horribly by the Great Depression. The entire system of share cropping, which is what had cropped up after slavery and plantations and all these things in the south, basically turned into a giant exploitation system of share cropping farmers who could not get out of debt.

Carrie Melissa Jones:

So they were in horrible situations, horrible poverty. And James Agee was a journalist. I think he was sent by Fortune magazine in the 1920s to go live with a family in the south. In their decrepit farmhouse. And he was sent with Walker Evans, who was a famous photographer from that period too. He took those New York subway photos that are really famous.

Carrie Melissa Jones:

He went with them. So then a photographer and a reporter were sent to live with this family and write a very short article for a magazine that people on the west and east coast would read, that taught them what's going on in the south. And how bad is it there? This kind of sensationalization.

Carrie Melissa Jones:

And he went and he refused to write the article. Because he was there and he ended up staying longer. And he said, "I can't. You want me to write 400 words on what people are going through here? That's not possible." He goes on for like 10 pages just saying, "If I could, I'd give you their clothing. Pieces of their hair. I'd give you the smell of the dirt. I'd give you the sound of the creaking on their front porches. But I can't give you any of that. So I will do what little I can in writing."

Daniel Stillman:

Wow.

Carrie Melissa Jones:

Yeah. I wrote my thesis on that book in my undergraduate.

Daniel Stillman:

Yeah. I can feel the import of it.

Carrie Melissa Jones:

Yeah. So, that's how I read all the time and it's funny. I wrote Building Brand Communities with Charles and I don't know that I would ever read my own books. Because I mostly just try to read things that are much broader about human nature.

Daniel Stillman:

Yeah. What would be the two books that you wish that everyone in the world would read? If it's now your book obviously.

Carrie Melissa Jones:

That's really hard.

Daniel Stillman:

I know it's hard but you got an answer.

Carrie Melissa Jones:

Oh man. I will probably take this back, once I think about it in a while.

Daniel Stillman:

Hot take.

Carrie Melissa Jones:

Yes. I will say that Macbeth is my favorite Shakespeare play and that is something everyone should either watch one of the movies or remakes of it or read it yourself. I have parts of it memorized because I'm just so obsessed with it. And let's see.

Daniel Stillman:

I don't have Macbeth outreach candle. That's the famous bit from it. What did Shakespeare say? What is your substance? What have you made, that millions of strange shadows on you tend. What is the little substance of Macbeth that you wish everyone would be able to touch?

Carrie Melissa Jones:

Um, well there's the one monologue where he, goes tomorrow, tomorrow, tomorrow.

Daniel Stillman:

Mm-hmm (affirmative).

Carrie Melissa Jones:

[inaudible 00:33:11].

Daniel Stillman:

Yeah.

Carrie Melissa Jones:

Yeah. And he basically wraps up all of life by saying that life is full of sound and fury signifying nothing. It's obviously very depressing.

Daniel Stillman:

I'll do a little like hand in writing. I see the connection.

Carrie Melissa Jones:

Exactly.

Daniel Stillman:

Yeah. All right.

Carrie Melissa Jones:

Yeah. I never made that connection myself. Yeah. I think it's just humility in the face of, we are such small creatures, and we're given one life to live, so don't kill the king. [inaudible 00:33:48].

Daniel Stillman:

Okay.

Carrie Melissa Jones:

It's not going to end well for you.

Daniel Stillman:

No, it won't. So Macbeth. Amazing choice. I love it. And what else do you wish that everyone would just pick up and read and spend some time with. Take a bath with.

Carrie Melissa Jones:

The other one is probably one of the books I recommended during the book swap. Which is the Body Keeps the Score. And that's not a book I would read in the bath.

Daniel Stillman:

No? Okay.

Carrie Melissa Jones:

No. It's about how trauma lives in our bodies.

Daniel Stillman:

Yeah.

Carrie Melissa Jones:

And I think if everyone read that book or knew about Bessel van der Kolk's work, we would have a deeper understanding of how little, what my friend, Nicole, calls little t and big t trauma. Little t is the trauma that all of us have. The everyday trauma. Just living. And then big t trauma like being in a car accident. In my case, being in a horrible relationship. All kinds of things like that.

Carrie Melissa Jones:

So we would understand how that's actually, until we heal it, it's living in our bodies. And we are recreating it and often recreating it in relationship with others. As my therapist says, that wounds created in relationship must be healed in relationship. We cannot heal our wounds that were created in relationship with people by of going inside and trying to fix it. Even therapy won't really solve it.

Carrie Melissa Jones:

The only way is to work through that in relationship to other people. And that's what communities can be for us, is a place where we can finally heal that if the community is healthy and doesn't recreate the broken structures that rest of the world has.

Daniel Stillman:

So I think there's a perfect time to transition. I'm going to reset the clock. This is what every facilitator goes through. Right? It's like, but this is good stuff.

Carrie Melissa Jones:

Yeah.

Daniel Stillman:

I do want to make a break and we want to talk about brand communities but I think what's interesting here is, the question I was sitting with was, well, what's the most important conversation that the brand community isn't having and that you want to invite? And it seems like I'm wondering what the shadow is. And I'm seeing that that is of great interest to you. What aren't we talking about? What aren't we looking at is really important.

Daniel Stillman:

And so with that, we'll magically transition to chapter two.

Coaching Executive Mindsets

I can’t believe it’s taken me SO long to share this conversation with the Amazing Elise Foster.

Elise is a powerful coach, an accomplished author, and a friend. She’s the co-author of The Multiplier Effect with Liz Wiseman and Beautiful Questions in the Classroom with Warren Berger (who’s written several bestselling books on powerful questions).

She was a thinking partner for me when I was in the early stages of writing my second book, and I was shocked and honored when she decided to come to my Facilitation Masterclass and even more shocked and honored when she actually got something out of it - proving that it really is more about what they practice and the container I create than what I teach!

I’m also honored that she’s been a great member of the Conversation Factory Insiders’ group - we started 2 years ago with alums of the masterclass meeting monthly for experiments and intentional practice, and 2 years and 22 sessions later, we’ve all learned a tremendous amount about leading groups online. Elise was kind enough to lead a session for the community on the QFT, a Question Formulation Technique from the Right Question Institute which has shifted how I think about Powerful Questions and how I coach teams on them, too.

In this conversation, I wanted Elise to unpack not just some of her favorite “Eye Opener” warmup exercises to help get teams to think differently, but also how she thinks about bringing them into sessions with teams, and why they matter.

Lots of folks talk about icebreakers - and they can be helpful to help us connect to each other from afar…but they are such a broad class of activities - they can include games like “Two truths and lie” which are just about connecting people as humans or “three things”, a classic improv game which helps folks just warm up their brains.

Priya Parker asks folks to check into the chat with where they are and what actual substance is beneath their feet, to help ground and connect us.

Eye-openers are both about what we do, as leaders and coaches of people in the moment, in order to create an experience for people…and eye-openers are also about how we help people reflect and unpack that experience and how to connect it to a larger idea about transformation and development.

Elise kicks our conversation off by talking about the “Hand Clasping Game”, a classic exercise that you can try now since we talk about it, but don’t give it enough time to “breathe” in the conversation.

Just clasp your hands together naturally. Of course, this assumes you have two hands. If this doesn’t apply to you, I hope you can imagine the process.

Now, unclasp your hands and “reclasp them” but shift hands - whatever hand was “pinky out” let the other hand be the “pinky out” hand. Elise calls this “reversing the weave” of your hands.

What do you feel?

Discomfort. Oddness. Weirdness.

That is a raw, visceral experience. Now, the magic happens when Elise unpacks this experience, and applies it to the context she works in - Leadership Transformation. 

Having a toolbox or a mental “file” of these exercises can be great…in fact, I have a whole online course about them. But as Elise and I discuss, having the wherewithal to bring one of these out in a session also takes some guts and some faith.

You take some trust the team has in you and burn it…risk it on an edgy experience…and hopefully you earn that trust back, with dividends, at the end of the unpacking.

Also worth noting is that this is the second episode on the theme of “An experience is worth a thousand slides” when it comes to coaching executive mindset shifts. The first conversation was with Jeff Gothelf, most notably the co-author of Lean UX, where we talked about the Vase and Flowers exercise, another powerful eye-opener that I love very much.

This episode is short and sweet, so without further delay, enjoy the conversation as much as I did.

Links, Quotes, Notes, and Resources

Elise Foster

Online Icebreakers Course

Coaching Executive Mindsets Part One

Minute 1

Daniel Stillman:

You said the stock and trade of your work is getting people to lean into discomfort. The clasping hands game is like what I would almost call a micro eye-opener. When and how do you bring that exercise into your work to unlock a shift for people?

Elise Foster:

There are times when I started with it, where it's a new team and they've already talked about their current discomfort and they've said, "I want to make some changes." Then I'll bring it in at the start and have them clasp their hands naturally and then reverse the weave. The look on their face is almost this quizzical look of, "Why am I doing this?" And then I ask for their reflections. "What was that like for you?" And they talk about how unnatural it is and it's easy to go into and that's what you're likely to experience as you try on any new leadership behavior, is you try to engage with people on your team differently. You're going to experience that unnaturalness and you're going to want to back to your natural state. What does that mean for you and your team and your team's effectiveness if you keep reverting back to the natural state?

And I think the other moment of insight, though, that I'm just thinking through is most people know changing leadership behavior is really hard. And I think the biggest aha is even when you walk into something knowing it's really hard and prepared for that level of difficulty, we don't recognize how easy it is to revert back.

Minute 4

Daniel Stillman:

It's a cycle of concrete experience, reflection, and then connection and forward thinking. I think all of those components are required to have a complete cycle of what I would call eye opening or aha-ing.

Elise Foster:

Yeah, and I think what's coming to mind for me when you say that is the slides are the contents and a lot of training experiences and developing experiences tend to sit squarely in the put more information in and you'll get better results out. And they don't focus enough on, "Wait a minute, the shape of the container might just need to change." And that's really what has to happen in leadership change is, "I have to start thinking about it differently. It's not just adding more stuff in, it's about how do I make sense of that stuff in new ways."

Minute 17

Daniel Stillman:

So, I'm wondering what you do that the line from Henry V is, "How do you screw up your courage to the sticking place?" What do you do to make you, yourself, feel like you can get away with whatever thing you're going to pull out of your hat?

Elise Foster:

Some of it's just being bold and trying it but I think some of it's in the set up. As I set up the session and letting people know, setting up the tone that it's going to be experiential. So, part of leadership is a thing you do and a set of instructions, if you will, that you try to implement each time, but it's also how you feel when you're doing it. And so we're going to weave those two together. There's going to be a little bit of an idea that we're going to play with. And notice I used the word play because there's going to be some experience that goes along with that and a lot of leadership, in my mind, is really about experimenting because even if you have a playbook that has worked reasonably well for you, when you add on a new team member or a new challenge that your team is facing, that playbook, exactly as you ran it before, may not work tomorrow.

Elise Foster:

So, as a leader, you have to start to be able to sense into and notice, "Oh, well this thing was working. Why is it no longer working and what's the little experiments I can run to see what's going on and how I might rewrite that play?"

More About Elise

Early in her career, Elise Foster was happy as an engineer, managing high-profile global projects to solve complicated problems. But, it wasn’t long before she realized she wanted to solve different types of problems. Today, Elise is a leadership coach who enables education and business executives to unlock their potential and achieve even greater success. She is well-versed in the field of leadership and collective intelligence within education systems and is the co-author of The Multiplier Effect: Tapping the Genius Inside Our Schools, which hit shelves in March 2013. As a Multipliers Master Practitioner for the Wiseman Group in Silicon Valley, Elise guides leaders on using their intelligence to make everyone around them smarter and more capable. Her clients include leading educational institutions and corporations such as the Chicago Public Schools and Abbott Labs. She is passionate about working with early career and seasoned professionals and she delivers effective workshops and coaching.

Elise wasn’t always this passionate about her work. She took a chance and changed from a life in engineering to one in training and development, becoming a management fellow at Harvard University where she worked with faculty, staff, and students. Later she made her way to Indiana University (Kelley School of Business) where she coached more than 200 MBA students. Her path also includes a stop as an adjunct faculty member, teaching and mentoring local college students.

She holds both a bachelor’s and master’s degree in engineering from Virginia Tech and a master’s degree in education from Harvard University. She is a wife and mother of one school-aged daughter; she and her family enjoy traveling and exploring new cultures together. In her spare time, Elise volunteers with the Lilly Foundation Scholarship and Youth Leadership Bartholomew County where she works to uncover the genius in each high school student she encounters.

Full Transcript

Daniel Stillman:

This computer, okay. Elise, thanks for making the time to have this little conversation with me. So, where we just ended is where we're going to start. You said the stock and trade of your work is getting people to lean into discomfort. The clasping hands game is like what I would almost call a micro eye-opener. When and how do you bring that exercise into your work to unlock a shift for people?

Elise Foster:

So, it's a great question and I think it's one of the things I'm trying to lean more into is the emergence of things. And so instead of building it into an agenda, I'm looking for the opportunities to take a pause. There are times when I started with it, where it's a new team and they've already talked about their current discomfort and they've said, "I want to make some changes." Then I'll bring it in at the start and have them clasp their hands naturally and then reverse the weave. The look on their face is almost this quizzical look of, "Why am I doing this?" And then I ask for their reflections. "What was that like for you?" And they talk about how unnatural it is and it's easy to go into and that's what you're likely to experience as you try on any new leadership behavior, is you try to engage with people on your team differently. You're going to experience that unnaturalness and you're going to want to back to your natural state. What does that mean for you and your team and your team's effectiveness if you keep reverting back to the natural state?

Daniel Stillman:

Yeah. So that gives them a burst of energy from insight, I presume. There's this moment of insight where your skills in peeling the onion, unpacking, and letting them just sit with that experience gets them to an aha moment.

Elise Foster:

Yeah, most people, they reflect and they're like, "Wow, I didn't think something so small could be so hard." And I think the other moment of insight, though, that I'm just thinking through is most people know changing leadership behavior is really hard. And I think the biggest aha is even when you walk into something knowing it's really hard and prepared for that level of difficulty, we don't recognize how easy it is to revert back.

Daniel Stillman:

Yeah, yeah. So the thing that we were talking about right before that thing was the idea of what I call underselling and over delivering versus overselling and under delivering. Always a better position to be in. There's not a giant lead-in. There's not a huge drum roll into this activity. You're looking for a moment to sort of insert that pause, that opening of thought. It's not like it's specifically in an agenda for you.

Elise Foster:

Exactly. It's one of the things that I'll have... I haven't thought of it in this way, but I'll have a list of things that I could do in a session just to tickle my brain before I go into it. So they can pop into my awareness more readily than if I didn't have this set of things available to me and the clasping of the hands is one that I do have available and when I hear people start talking about their difficulty changing and how easy is it to revert back. To use the overused term these days, the somatic experience of feeling that...

Daniel Stillman:

Is it overused? I feel it could be used more by more people, but...

Elise Foster:

I guess it depends on what circles you run in. In the circles I run in, everything is about the somatic experience.

Daniel Stillman:

Yes. Let's use a better word. You're giving them a visceral experience of an idea. This brings in my new favorite watercolor that an experience is worth a thousand slides. Right, because you could give them a whole slide on that and I'm sure there's somebody who's got... No offense to anybody who's listening. It's like, you could explain that in a slide deck but people have to do it and then they have to have you ask them a question and have some silence while they kind of struggle and think about it and then they need you to connect it. It's a cycle of concrete experience, reflection, and then connection and forward thinking. I think all of those components are required to have a complete cycle of what I would call eye opening or aha-ing.

Elise Foster:

Yeah, and I think what's coming to mind for me when you say that is the slides are the contents and a lot of training experiences and developing experiences tend to sit squarely in the put more information in and you'll get better results out. And they don't focus enough on, "Wait a minute, the shape of the container might just need to change." And that's really what has to happen in leadership change is, "I have to start thinking about it differently. It's not just adding more stuff in, it's about how do I make sense of that stuff in new ways."

Daniel Stillman:

Yeah, yeah. So, let's connect this back to 1713 because I remember your aha when you went through that game for the first time. You're like, "Wait a minute. I can use this." And I think you're still on your journey of bringing it into... It's not in your tickler file, where you're like, "Oh, I can definitely bring this in." So, I'm wondering if you can talk about your arc of the aha you got trying it out in a low stakes way and then maybe we can go deeper into the mechanics of the thing, potentially.

Elise Foster:

Yeah, the two things that I remember most vividly from that experience was how little I know about the year 1713 and virtually everyone else knew about the year 1713 in that session, but how much that lack of knowledge kind of put us on equal playing ground. Just to set the stage of it, you brought together a group of people who didn't know each other at all. There might have been one or two people who knew each other, but the vast majority of us didn't know each other and it was a nice entry point to come in where we're all on this unstable footing and kind of feeling uncomfortable. So I think it created safety for people not to know and it created an awareness for me that there's a whole host of things we think we know a lot about but we don't.

Daniel Stillman:

In that we can't explain it perfectly to someone who has no knowledge of it.

Elise Foster:

Right.

Daniel Stillman:

So, I'm curious. I mean, so, the way I think of 1713. One of the things I love about it is... For those of you listening, it's an improv game where one person has to explain a thing to someone else who pretends to be from 1713, which is super fun because I think there's this idea that explain it to your mom, explain it to your grandma. And I'm like, "That's kind of sexist and ageist." So, let's be chronoist. There's nothing particularly controversial about just pretending to be from several hundred years ago and not understanding an iPhone. Which, by the way, I think I've seen one of the perfect introductions to it which is like explain an iPhone to someone from 1713. But I'm curious. You found an opportunity to bring it into your work in a low stakes way and you had some learnings and insights from it.

Elise Foster:

Yeah, so from the day we did that session, I'm like, "Where can I use this?" And one of the challenges is and I think part of it is I'm probably making it too big a thing. Like, "Okay, I need to insert this thing." And maybe if I did have it in that tickler file it might be easier. I didn't have, and I still haven't quite found what is the direct connection to this particular team effectiveness program or this particular leadership development program to use it, but I did have an opportunity. I was part of a three-day virtual conference and they were looking for people to host 90-minute sessions and then people to host 30-minute kind of in-between sessions. And I thought, "This is a great opportunity to play with some of these icebreakers." It's a super safe space and it's with other people who do a lot of online facilitation but are still in that transition phase of, "Well, I used to do all this in person, so I'll just take my slides and bring them up onscreen and do it that way." And so I thought it'd be a fun exercise. So, it was super fun. People had a lot of fun playing 1713 and then my all-time favorite game that I changed the name of to make it Seven-Second Animals.

Daniel Stillman:

Hey, just for the record, it was taught to me as Three-Second Animal and I changed it to Five-Second Animal because I thought that was too cruel. I think you're being way soft on your participants by making it Seven Second Animal. If I can go on record.

Elise Foster:

I am fully aware of that and I have a feeling the people that I shared it with will make it Nine- or Fifteen-Second Animal because-

Daniel Stillman:

Slippery slope.

Elise Foster:

But the couple things that I learned. One, people experienced this experience of not knowing in two ways. One, I have no idea what happens in the year 1713. And two, I don't know how to explain something that I do every day. And some people really leaned into it an got super creative and had a lot of fun with that piece of, "How do I get really creative about talking about these Zoom screen windows?" And the learning that I had, though, is... I had people and we did two rounds and it was as much an eye opener as it was a way to get to know and have a familiar face on the screen. So in between the two rounds, somebody said, "Oh, are we going in with the same topic?" And I thought, "Well, here's an opportunity and if they wait, it'd be emergent. And oh, well I had planned the same topic but what if we try a new topic? What topic would you like?" And the topic that they went with had to do more with the pandemic and this global reach of the pandemic.

Elise Foster:

When people came back, you noticed a different tenor in the conversation because people could relate back to understanding plagues and different things like that in the year 1713. And so the content area, the topical thing that you have people explain, I think, is really important. If there's any way to connect it back to a time when we didn't have the kinds of technology we have now. I think you'll have an experience, it won't, maybe, be the eye opening experience you want it to be.

Daniel Stillman:

Well, so there's so many things that that lights up for me and one is my own preference for... There's what I would call a pure icebreaker. Which is like, "Hey, name, rank, and serial number." Classic and it's barely even an icebreaker or like two truths and a lie. No offense, but it just doesn't do anything for me, as you know. I've said this before. To me, something like 1713 does warm people up. It does break ice but it is doing it about, potentially, content. And it's especially valuable. When I think about the finger clasping exercise, it's about discomfort and leaning into transformation. 1713, for me, is about connecting people to universal human needs and experiences, which in the product innovation and product design world, the idea of jobs to be done or user goals or personas.

Daniel Stillman:

Actually, the first time I used this, and this is super relevant to what you're going do for a facilitation Friday. It was at a hybrid meeting. An unintentionally hybrid gathering where there were like four or five people in person and maybe five or six people remotely because they didn't realize they were supposed to come in for this meeting. It was part of a 5G innovation lab that I was helping Verizon run and 1713 is the perfect game for a startup founder who's trying to design some internet of things sensor array for them to try to explain that in the most basic fundamental human components. It is grounding. And it worked fairly well for them to share their own insights after they're paired up experiences. I can pair up the remote people and the physical people and the remote and the physical people can still tell the story of their insights to each other.

Daniel Stillman:

That, to me, is the function of leaning into discomfort. You have that connected to a group need and from an innovation transformation perspective. That's what I connect 1713 to. It's like, "Oh, these people need to understand jobs to be done because their ideas are way out here and they need to get them right back down on the ground level of a person with a goal." And those things, the whole idea of jobs to be done is that it is durable. Like you said, with the pandemic, people have had that need, "How do I manage myself and my family when I can't go out and when I can't talk to people?" Like, that's something that happened and has happened and will, unfortunately, keep happening.

Daniel Stillman:

So I think it's like, when people say, "Oh, I need an icebreaker or a warmup for our gathering," I'm like, "Well, what do you want to do? What is your goal? What is the transformation you want to unlock for that group of people?" And I think that's what's interesting to me because I can hear you do that for your groups. You're thinking to yourself, "What do I need to unlock for them?"

Elise Foster:

Yeah. Well, what you're raising for me is two things. On the leadership transformation side, so much of the change is more elusive. It's not a durable good. It's not a thing I can see, touch, or feel. And so it has me puzzling through, what is that connection that 1713 could make within the context of their business and when you pitched the idea of having this conversation it had me thinking about an IT leadership team that I'm likely to be working with soon. When I think about the IT systems that exist today and what they're trying to do today to connect their global business, that could be a really good grounding piece, to start with 1713 to ground them in the work that they do and why it's so important for them to be effective as a leadership team.

Daniel Stillman:

Yeah. So, the thing that was bouncing around my head is I think sometimes people feel like, "I can't do this with a group of senior folks because they just want some slides. They want me to tell them what's what and they're going to think I'm bullshit or something and I'm going to have to sell it to them." So, I'm wondering what you do that the line from Henry V is, "How do you screw up your courage to the sticking place?" What do you do to make you, yourself, feel like you can get away with whatever thing you're going to pull out of your hat?

Elise Foster:

Some of it's just being bold and trying it but I think some of it's in the set up. As I set up the session and letting people know, setting up the tone that it's going to be experiential. So, part of leadership is a thing you do and a set of instructions, if you will, that you try to implement each time, but it's also how you feel when you're doing it. And so we're going to weave those two together. There's going to be a little bit of an idea that we're going to play with. And notice I used the word play because there's going to be some experience that goes along with that and a lot of leadership, in my mind, is really about experimenting because even if you have a playbook that has worked reasonably well for you, when you add on a new team member or a new challenge that your team is facing, that playbook, exactly as you ran it before, may not work tomorrow.

Elise Foster:

So, as a leader, you have to start to be able to sense into and notice, "Oh, well this thing was working. Why is it no longer working and what's the little experiments I can run to see what's going on and how I might rewrite that play?"

Daniel Stillman:

So, what I'm hearing you say, and I think is very true is you have to set up that they're coming into a space that is going to be different. You can't sandbag them entirely but there is also a little big of sandbagging where you... I'm hearing in your tee up, it's like, "Hey, everyone. Leadership is about experimentation and so we're going to run an experiment together, right? So bear with me, this might feel uncomfortable. Everyone stand up and dot, dot, dot."

Elise Foster:

Yeah, exactly. And then inviting them in that to experience their discomfort and notice what was uncomfortable for them. What was the voice in their head saying? Was it, "I'm going to look like a fool in front of my companions?" Is it that, "I just don't think there's anything we can learn from this." What's their self talk? "I have better things to be doing. I have a problem to be solving."

Daniel Stillman:

But this is profound, Elise, because I think we often feel like as folks who are coming in as change agents to coach a group of folks... I'll just say for myself, I know people are like, "Daniel, tell us what to do." Right? And the whole, "Fill us up with more knowledge so that our knowledge cup is full so that we can just pour it out on everyone else." The idea that it's my job to make them sit with some discomfort, that's something that I strongly identify with. It is my job to get them to sit with this uncomfortable moment of, "What was that like? How would you connect this to your work?" Because I have a little bit of faith that they will have an insight. But I think there is a feeling of abject terror in myself and everyone else when you pull one of these things out that maybe it won't land. Maybe it won't connect. Right? Maybe they won't have an insight.

Elise Foster:

Yes, and what you're raising for me is sometimes they won't, but they will still try to convince you they have because they play along really, really well.

Daniel Stillman:

Right, right. Yeah. Confabulation. People have had an experience and if all they say was, "That was uncomfortable and I hated that," then we can still work with that, presumably.

Elise Foster:

Presumably, but there's also, I think, the other element to this is I think, in my experience anyway, is you can get a room full of people who all had an experience together and there's one person for whom it was really profound and then everyone else is like, "Oh, it was really profound for them. Maybe it should have been more profound for me, so I'll add something in that makes it sound like it was profound for me." And there's not a lot you can do with that and you probably won't know for whom it was really profound. I think, though, creating the space for people to have the reflective moment there and some sharing gives people something to take away and hopefully further reflect on.

Daniel Stillman:

Right. So, when we think about how to do the workshop math to include these things, I think there has to be some popcorning of people's experiences in. And depending on how large your group is, that can be a lot or a little. And if we want to add on your experience I doing this, I think you always need a warmup to your warmup. So, I think what you did in the group was great, where you said, "Okay, let's do it with something straightforward that we all know and then let's do it with something stranger that's harder for us." I mean, these things take time. I think this is actually the biggest challenge that I'm having with this executive leadership team session that we're doing. It's like the max we can get is two hours with... these are very, very senior people from a major global brand and me and my internal [inaudible 00:22:51] are having this little battle over... She's like, "Can you do it in 30 minutes?" And I'm like, "No. I can't. It takes 45 because they have to think and we have to talk and we have to hear from everyone and that means she only has another hour and 15 to do all the slides."

Elise Foster:

It's probably been three or five times in the last week and a half where I have heard a colleague say, "You know, I have just decided, I mean, in this online world, you can't do anything more than two hours." I mean, you just can't do anything more than two hours because people check out. It's the max people can offer you and when I think about the experiences that we had in the Master Facilitation course and some really well held online facilitation, I don't think it's the length of time that matters. I think it's how you choose to use that length of time. So when you think about planning this, it drives me want to ask the question of the leaders you're working with, "Okay, what is driving your time window?"

Daniel Stillman:

Thank you for the pushback. You're not wrong, but I think part of the reality is people... It's about their commitment to anything. Like, nothing's that important because everything is important. To literally get four hours from them. Like, of course I could design a four hour session that would be deeply engaging and would be incredibly valuable, right? But the question is would they be willing to see it as an organizational imperative to give up a "full day." It was hard enough to get a full day back in the day. Now a full day is... I mean, people just have kids around their house and even the CEO of a major brand can have a baby or a pet walk across the screen. But the pushback is well taken and well provided.

Elise Foster:

Yeah, and I think it's also pushback, though, for my own thinking, to go, "Okay, why am I pushing for more time? What is it?" And so it just means you do really have to do the math. What is the way that I quickly bring them in and knowing... It was funny, I did a session for a big Latin American brand and I came on and I started talking and I'm immediately getting Zoom messages going, "There are no slides showing. There are no slides showing." I'm like, "I know there are no slides showing. Trust me, the slides will come but there aren't any slides right now." And so it was a great learning to set expectations for what is it that we're going to be up to here today and this may look and feel like some of what you've experienced in the online world and it may look and feel quite different.

Daniel Stillman:

Yeah. So this goes to setting expectations and what my counterpart and I were talking about was when you're designing that arc of the conversation, I was like, "Let's just have a hot start." And we just let them know that we're not going to do introductions. They all probably know each other. They don't need to do that thing. As much as I love check-ins, this is not the time for it. Okay, we've got two hours with these folks. You're like, "Everyone, grab your pen and a piece of paper and we're going to draw a vase." And it's like, "Okay, that's where we're going." And I think the way I think about it is, "I'm going to burn some trust and hopefully I will earn it on the back end as quickly as possible.

Daniel Stillman:

You know, this is a very short burn and a very short cycle of the clasping hands if you're listening to this while you're folding laundry. The clasping of hands is a short burn and a strong payoff because you've done it a million times. 1713, because it's an improv game and requires either a fishbowl conversation and two very, very brave volunteers and then potentially a breakout session and then a popcorn coming back. It's a 30 minute set piece and so you have to really want to help people understand jobs to be done is the way I would put it or that we don't understand who our product is for or we can't explain it to ourselves or to each other in our organization. You talk about the IT silos that you're talking about. Like, "Can we actually explain all of our silos to each other? Right? And if we can't, then that's aha, we can't. But that means that we don't understand them."

Elise Foster:

Yeah. I think the word aha is kind of ringing true to me in this conversation. The work to be done is to create a container so that everybody can have an aha no matter where they are in the process. For some people the aha is going to be a big huge thing and for other people, it's just going to be, "Oh, I realize how uncomfortable that is and maybe I need to get more comfortable with discomfort." And other people are going to go, "Oh, I totally see why I have abandoned that thing I have been so committed to doing."

Daniel Stillman:

Yeah. There's one thing that I'm really taking away from this, because I know our time is growing nigh. This idea of the bell curve of people's experience and that it's okay that somebody's going to be like, "Wow, Elise you changed my life. I never thought about leaning into discomfort." And somebody will be like, "I don't really get it, but I can see other people are..." And then this person in the middle is like, "I see other people are getting it and so that's kind of interesting." And that that's okay because what you've done is you've given them an experience together and they get to talk about it, unpack it, and potentially own it and it can sometimes just become a metaphor. Luckily it can become a new piece of languaging for people. So like, "How are we leaning to this exercise or can we explain this to somebody from 1713 or are we building a vase or a way of experiencing flowers?" Which is another exercise I may be sharing in this workshop. I think it's profound to give people a shared experience.

Elise Foster:

Yeah, thank you for that and I think it's profound and we can't know how much it nudges the system. That experience is something that might not take hold for 18 months. And 18 months later, something major happens because of that experience and we'll never, ever know that.

Daniel Stillman:

Boy, that is heartbreaking, though, because this work is hard enough, right? And transformation doesn't happen with the snap of a finger. It takes time. So yeah, it sounds like one thing you remind yourself is, "This is a seed I have planted," and to trust that it will find and take root.

Elise Foster:

Yeah, and if you have more than one opportunity with them, what do you notice in the soil consistency and what new nutrients do you need to bring in to help it grow just a little bit faster if that's what you're going for?

Daniel Stillman:

Yeah, yeah. You know, we can accelerate it by providing some heat and some focus, but it's a balance. I'm growing seeds right now, so this is very much a take-home for me. It's like, you can build a greenhouse but you can get too much moisture and then you have mold. Right? You can overcook it, right?

Elise Foster:

Yeah.

Daniel Stillman:

So I think holding these experiences lightly and just being like, as my mother would say, "Everyone is here to contend with themselves." Right? We're providing them an opportunity to have an experience. We can't force them to have an experience.

Elise Foster:

Right, and the more you try to force it, the more mold you grow.

Daniel Stillman:

Right. Elise, anything we haven't talked about? Anything I haven't asked you that I should have asked you about this idea? We've covered a lot of really interesting ground on this.

Elise Foster:

No, I think I just want to say thanks. It was a really fun conversation and something new always is sparked when we have a conversation. So thank you for that.

Daniel Stillman:

Thank you. Yeah, I'm leaving with this, like, "You can't force someone to have an experience. It's an opportunity." And to remind myself and everyone else, it is a risk and the payoff can be there or not and that it's okay.

Elise Foster:

I mean, just with that, when I coach clients, there's something they're up to in between sessions and I always remind them, "Don't beat yourself up if you don't do the thing. Just pay attention to what got in the way of you doing the thing because we learn as much from you doing the thing as we learn from you not doing the thing."

Daniel Stillman:

Right. I agree, and they feel so bad. Negativity keeps them from trying again.

Elise Foster:

And we learn from that and so I think that's what your comment brought up for me. So, thanks again.

Daniel Stillman:

Thank you, Elise. I will call scene. I'll stop recording.

The Conversation Factory Book Club: The Creative Empathy Field Guide with Brian Pagán

I'm so excited to share this book club experiment with you. I've been inviting alums of my facilitation masterclass and subscribers to the conversation factory insiders group into intimate conversations with authors of transformative books. In this conversation, my friend Brian Pagán, Author of "The Creative Empathy Field Guide," is our guest.

Brian points out early on that empathy is lauded by many thought leaders and no lack of articles - with the simple, inspirational message that empathy is good for you! And while that is absolutely true, what is missing is the how of empathy - not the why. Brain sought to fill this gap with his book, "the creative empathy field guide" which is a very short and very helpful book....and if you follow the links to Brian's website at the Greatness Studio, he's got a "greatest hits" selection from the book that you can access, free of charge.

So: Just to clarify our definitions: Creative Empathy is the use of empathy in the creative process. That is, we are making things and those things are not for us. So, we must learn to both connect with those people we are creating for and to detach from them - we have to tap into our skills of emotional agility to lean in and out of creative empathy.

One thing that you'll find most surprising (or at least I did!) is that creative empathy benefits from some of the tools of method acting - the ability to connect to your own experience and bring that experience into the present moment.

One thing that is missing from this conversation is my friend and guest from early in 2021, Dr. Lesely Ann Noel, who really helped me understand that there are limits to us-them dichotomies in design thinking and that designing for others can reinforce existing power dynamics, stereotypes and "othering" of people. Brian does address this in his book, but I recommend my conversation with Dr. Noel, DeColonizing Design Thinking. Dr. Noel has a complementary array of tools to help decolonize our thinking, like her Positionality Wheel which we turned into a Mural template to help you facilitate that conversation with your teams.

In this conversation, Brian and the Conversation Factory Insiders Community dives deep into The Empathic Design Process that Brian adapted: 

1. Discovery, 2. Immersion, 3. Connection, 4. Detachment

Discovery: As creators, we approach the other person’s world, which provokes our interest, curiosity, and willingness to empathize.

Immersion: We enter the other person’s world, look around, and absorb what we see without judgment.

Connection: Here, we resonate with the other person’s experience by recalling our own relevant experiences and memories.

Detachment: Finally, we leave their world to focus on creative action, before starting the cycle afresh.

Also check out Brian’s site for Free Creative Empathy Tools like an Ethical Design Checklist, his Journey Map Canvas and a Character Map Canvas (as an alternative to personas).

Links, Quotes, Notes, and Resources

Brian Pagán 

The Greatness Studio - What’s your superpower? 

Creative Empathy - The Greatness Studio

Brian Pagán on Twitter

Double Diamond: What is the framework for innovation? Design Council's evolved Double Diamond

Personas: "The word derives from Latin, where it originally referred to a theatrical mask"

Method Acting: "The method" is a range of training and rehearsal techniques, as formulated by a number of different theatre practitioners, that seeks to encourage sincere and expressive performances through identifying with, understanding, and experiencing a character's inner motivation and emotions

For-With-Am-For: Shifting Perspectives as a key to the creative process: Discovery "I work for you", Immersion shifts to the 2nd person "I feel you", Connection shifts to the 1st person "I am you" and Detachment shifts to the 3rd person again "I work for you."

 

Minute 18

Daniel Stillman:

If you were to choose one tool, what is your favorite tool for getting people to connect? When you talk about it as a field book and you talk about tools and techniques when you're teaching teams about how to be more creative in the way they connect for creative projects, what do you feel is the tool that people really find the greatest leverage or connection or ease in? And maybe also which one's the hardest and the most struggling, but that they should get better at?

Brian Pagán:

I think the biggest... I hesitate to call it a connection technique because I think it's something that serves the entire inner loop, so it's for immersion and connection in that sense, but trigger cards and sensitizers as something that's in the book. These are... So if we look at the idea of sensitizers, any sensitizer is some sort of bit of information or some kind of story or some kind of personal thing that we share about someone in the targeted audience or in our group of people we're designing for, that allows us to emotionally connect with it. Somehow invites our resonance, our emotional resonance with that thing.

And one of the ways that we can create sensitizers are trigger cards. And in the book, I show trigger cards from Melina Lopez Reyes who is a graduated master's student. And she did her project, her graduation project in Mexico around victims of domestic abuse. And what she found was that whenever she was working together with government officials or people who run associations or sort of volunteer organizations that help victims of domestic violence, they... In ideation sessions, it was helpful for her to sort of prime people with stories from her interviews. So she talked with a lot of different victims and made their stories really easily digestible with these little cards that people can use.

So before an ideation session, she can distribute these cards to the participants of the ideation session, and either as part of the session itself or as part of the pre-read that before you actually join the session, you can go through and look at these trigger cards. And because they tell such intimate stories and real stories based on actual research, they allow us to emotionally resonate with what's going on and the experience of those people that we're actually going to be ideating for in the session itself.

Minute 21:

Daniel Stillman:

My last question before I unleash the other brains in this room is what is not in the book but should be? Because I know that happened to me.

Brian Pagán:

Oh yeah, for sure. There's so many things. What's not in the book and should be? What is going to be in the expanded version is something about the hierarchy of spiritual intelligence from Cindy Wigglesworth. And going back to our earlier talking about humanity and recognizing shared humanity, Cindy Wigglesworth came up with this thing called this hierarchy of spiritual intelligence, which is basically four stages of connection between people going from apathy to compassion.

So first it starts with apathy, like you don't care. It doesn't matter. Whatever. And then there's sympathy, which is not quite empathy, or you feel sorry for someone, but you're still not really opening yourself and being vulnerable to putting yourself on their shoes or even trying to relate to them on that level. Then after that is empathy, where we actually recognize each other's humanity, we actually try to connect our own experiences with the other person's experience. And then we have compassion, which is where we take our empathy and our feelings of wanting to help this person and actually put them into action and do something about it. This is where we build a house or help the person out or give a hug or these, whatever compassionate action it happens to be. Or design an app for them, or whatever kind of thing. These are the four stages, let's say, of from how you get to compassion.

And just bringing those together and putting empathy in that context helps to understand that, one, if you can feel empathy for someone else, it basically forces you to recognize them as a human being and recognize their humanity because you're connecting your own experiences with their own too. So I think that's quite important and also shows that empathy can lead to compassion. It's hard to have compassion for someone if we don't have empathy for them first, if that makes sense. So those are the two key things that I'd like to bring in in the next version, let's say.

Minute 24

Erin Warner:

Could you explain the purpose and the value of detachment?

Brian Pagán:

Absolutely. So as far as I understand it, the difference between immersion and detachment is just the fact that it's hard for us to look objectively almost at something if we're still immersed in another person's world. Another way to say it could be that empathy exists out of two different components. There's the effective emotional component, and then there's the cognitive more rational component. And if we have too much of one without the other, then it can either be dangerous if we have just emotional empathy without rational empathy. But it can also just go too shallowly. If we don't connect emotionally, then we're not going to... We're not really having true empathy in that sense.

So I think by virtue of the fact that we go, we immerse ourselves in another person's world and then connect our own experiences with that, that's the inner loop. And then once we detach from that, then it gives us the psychological space and distance to be able to more effectively weigh the needs of the person in whom's world we just were immersed in, and everybody else, if that makes sense.

More About Brian

Hats I wear include speaker, actor, podcaster, writer, and UX consultant. Over the last 19 years, I’ve worked with around 40 clients, coached 16 startups, and traveled to 11 countries to give talks and teach classes.

I founded The Greatness Studio in 2016, Computer Drama in 2018, and MindFolk in 2020.

My home is with Hester Bruikman-Pagán in Zeeland (Netherlands), and I’ve loved avocados since before it was cool.

Full Transcript

Daniel Stillman:

I'm going to start recording in progress. Brian Pagán, thanks for being here for the Conversation Factory Book Club. And Chantel, Erin, and Jim, thanks for being here from the community to make the conversation so much more interesting than it would be if it was just me or just me and Brian. If it was just me by myself talking for the whole time, I don't think that would be that interesting at all. So thanks for making the time you all.

Daniel Stillman:

Brian, people can Google you, but what's important for us to know about you that we cannot find on the Google? What's important for us to know about you so we can get to know you before we get started?

Brian Pagán:

It's funny. I was just having a conversation with some students at the Amsterdam University of Applied Sciences, and a lot of students are doing projects around gender and gender identity. And we just went off on a tangent talking about how more common it is these days to be defined by what you're not in the sense that anyone who might be different from the mainstream or different from what we would consider a default in Western society, that we're just starting to define ourselves as like non-monogamous or non-binary or non this, non that. And it's, yeah, I think in some kind of way, I think that applies to me a lot as well. I remember having a T-shirt back in the day in Germany that said "Not quite normal." And I feel like if there's a sort of nutshell description of myself, I think that would be it.

Daniel Stillman:

Not quite normal.

Brian Pagán:

Maybe that's how I want, I pretend that I am. Maybe I'm just super normal and very boring, but then I think, oh yeah, if I pretend I'm not... But people think I'm more interesting. Maybe it's that. I don't know, but I definitely, yeah, don't feel like I fit into a lot of the default things of our society, if that makes sense.

Daniel Stillman:

Yeah, that does make sense, and I identify with that, which is maybe why we hit it off. So Chantel, Erin, Jim, what you don't know is Jim and Brian and I met drinking I think in New Orleans as is common at an interaction, Information Architecture Conference like 2012. That was a really, really long time ago. And we reconnected recently and sort of found that the arcs of our careers from sort of user experience design to thinking about humans. And UX designers at one point sort of woke up to this idea of like, "We're the only people who talk about our customers in the same way that drug dealers do." That's one of the classic quips of like...

Brian Pagán:

Oh yeah.

Daniel Stillman:

They're people, and then also in sort of the coaching and transformation space. So Brian and I have a lot of overlap. We've had some really wonderful deep conversations. And he shared this book with me and I thought it would be a really interesting opportunity to share this book with you all.

Jim Burke:

Drinking happens in New Orleans?

Daniel Stillman:

Yeah. It does.

Brian Pagán:

What? Shocking. Clutch the pearls.

Jim Burke:

And that's where the best conversations come from. The deepest thoughts come out of doing that.

Daniel Stillman:

Well, let's just say from heightened states of consciousness, Jim. There's lots of ways to get there.

Brian Pagán:

For sure. Yeah. I will say there were also musical instruments there. There was a lot of music, music playing, piano playing, and singing, and guitar playing, and stuff at the party we were.

Daniel Stillman:

Yeah, that was a good party. A rare party. It was one of those... Somebody had rented a room that had one of those balconies. There's something... By the way, if you're listening to this and you haven't been to New Orleans... Show of hands, who's been to... Chantel, have you been there?

Jim Burke:

Who's been there? Yeah.

Daniel Stillman:

You've been to New Orleans? Chantel, that's amazing. All the way from South Africa.

Chantel Botha:

Five years. Daniel, five years in a row. If you say "New Orleans," I say-

Daniel Stillman:

"When."

Chantel Botha:

... "Beads, beignets, and hurricanes."

Daniel Stillman:

The drink, not the atmospheric-

Chantel Botha:

Yes. No. The refillable cups with-

Daniel Stillman:

Yeah, yeah, yeah. Also jazz.

Brian Pagán:

Like this tall made out of plastic with a huge straw. Yeah.

Daniel Stillman:

And crawfish. That's what's really important to me about them.

Chantel Botha:

And then some black magic if you're into that.

Daniel Stillman:

And some black magic. All right. So now we really know Brian. Excuse me. So I'm really curious as somebody who's written a book, how is the book, how did writing the book change you? What was like, this is maybe my meta question was like, what was it like for you to write a book about this and what has it done to you? Maybe not for you.

Brian Pagán:

That's a great question. I think the first thing would be that it made it lot less scary for me to write a book, if that makes sense. Just I guess the first time... Because I always knew that I wanted to write a book or write books. I've always been very interested in writing. And so I, for a long time, I had the fantasy of just writing a book. But doing it the way that I did with the publisher Bookboon, they had a specific process, and it's almost like they coach you through the whole thing, and that really helped me to just write the first one, if that makes sense. And most of the time, the first one's the hardest one, right? So I think after that, I guess just the internal change or internal shift for me is I feel much more confident as a writer. I feel much more confident in the idea of, could I write a book? Yeah. I know I can. I have proof. And also just articulating the ideas in such a way that other people can hopefully understand them.

Brian Pagán:

I'm really curious to hear you all's thoughts about this too. Because did I succeed or not? We'll see. But yeah, I think that was the biggest change was the internal change of having confidence and also more the content wise change of understanding the things that I wanted to write about better because I had to formulate them for other people.

Daniel Stillman:

And why empathy and why creative empathy? Why a field book?

Brian Pagán:

So empathy is something that I feel like we need more of in the world. I know there are people who don't necessarily agree with that with folks like Paul Bloom, for example, talk more about compassion than empathy. But in my mind, empathy is something that we need if we want to be able to have compassion for each other and treat each other more kindly.

Brian Pagán:

And if there's... I don't know. I feel like there's a general overwhelming understanding that we seem to be farther from each other as human beings than ever. And they're all kind of factors and stuff, but one way to get back through that is just to recognize each other's humanity, treat each other like people. And I feel like if we were trained in emotional intelligence, if we learned very practical things, techniques about how to regulate your own emotions, how to empathize with another human being, how to listen to each other, then the world would be a much better place with or without technology, if that makes sense.

Daniel Stillman:

Yeah, it does.

Brian Pagán:

You still hear me. I'm getting a message that my internet connection is unstable, so...

Daniel Stillman:

Oh no. I hear you loud and clear.

Brian Pagán:

I hope I'm not breaking up.

Daniel Stillman:

That's fine for me.

Brian Pagán:

Oh.

Daniel Stillman:

So I think it's really important to contextualize this because I think there's at least two layers here. Obviously, there's the human and day to day, but specifically you're coming from the context of product design and product innovation. And so that's where I think the empathy process and the sort of like the first question I have for you is a visual question. Well, it's because this diagram was new for me. And this... I mean, I love visuals. I love models. I love loops, especially when there's two of them, and this empathic design process, and for people who are listening, maybe you can describe it, how you found it, and why... I mean, because it's sort of like, to me it feels like the backbone, the beating heart of the book, if that's correct.

Brian Pagán:

It definitely is. For sure. For sure.

Daniel Stillman:

Also interestingly in the book, I don't think this is red, this little number three is red, but on Bookboon, it is, which is interesting. So maybe you can tell us about...

Brian Pagán:

So of course there are two versions of it. There's a color one for the digital, for the ebook, and for the just paper book I wanted to keep costs down and try to make sure that things are, for the environment they aren't too damaging. So I did everything here in monochrome black and white. So basically, it's all in just black ink, whatever.

Brian Pagán:

But yeah, to answer your question. So I definitely see this for me as the big theoretical backbone of everything. And for folks listening, basically it's two loops. There's a loop inside another loop. So it's a four-step process and the two steps in the middle, so steps two and three, form their own sort of loop, if that makes sense. So you go through the first stage is part of the outer loop. And then in the second step, you go into the inner loop, to the third step, and this is immersion and connection. And then you leave that inner loop and go outside again to the outer loop with the fourth step. And just to really quickly talk through that, the four stages are discovery, immersion, connection, and detachment. Yes, exactly like you've drawn it with the thing on the screen.

Daniel Stillman:

Terribly.

Brian Pagán:

But it does make sense in that way because it's sort of almost like a railroad track in the sense that you go into one and go onto the other one. And if you look at-

Daniel Stillman:

So discovery, immersion, connection, and detachment.

Brian Pagán:

And detachment, yes. Yeah. So if we look at like a traditional design process, we already have discovery, immersion, and detachment. Discovery would be something like when we do market research and we notice that there are, I don't know, there are millennials who would like to have some kind of product and they're not getting it yet, and their needs aren't being met for some reason. And then people would start doing UX research. This is where we do immersion, where we do ethnographic studies, or they gather information about people.

Brian Pagán:

And then we skipped already to detachment. This is where we start designing stuff. And what empathy does, and the reason why, and just to go back to your earlier question, why creative empathy? Creative empathy for me is empathy applied to a creative process. And that's why it's a field guide as well. Because I wanted to make it very practical. Most of the stuff around empathy these days... I don't want to talk trash about anybody, but a lot of it is about how great empathy is and how it can help our lives, but there's not really much around how do I get started? Steps one, step two, step three in order to do empathy.

Daniel Stillman:

Just by, just super meta, that's very empathic of you to not talk trash about the other empathic thought views.

Brian Pagán:

Thank you.

Daniel Stillman:

I can really see their point.

Brian Pagán:

Exactly. Yes. I try to... But so this connection part, basically the thing about empathy is, it's twofold. One is that as designers, everyone's always talking about, "Yes, I'm customer obsessed and I want people to... I want to make things that people love. And I want people to really fall in love with my business and my brand," but we are not allowing ourselves in the creation process to be vulnerable towards the people for whom we're creating. Right? So we don't fall in love with them, but we expect them to fall in love with us. Right? And so this connection phase is when we actually, after immersion, after we've immersed ourselves in the world of another person through our research or through simulators or whatever, the connection phase is where we create space to reflect in our own experiences to understand that thinking about the last time that I felt the way that this person I'm observing is feeling.

Brian Pagán:

And then I can ask myself, what do I need when I feel like that? And if I can recall that in myself, this is another reason why I use a lot of acting techniques in the book, because acting is a lot about emotional recall and stuff, like bringing an emotional state into your mind so that you can use it. Once I get that into my head... Let's say I'm looking at someone and I can see that they're sad while they're interacting with a certain system. What do I need when I'm sad? I can recall that for myself. And then when I detach myself and start working on the actual solution, then I have an extra layer of insight and understanding into the sadness and the needs of the sadness around it. Does that make sense?

Daniel Stillman:

It makes a ton of sense. And I really want to highlight a phrase you said that was devastating, which is that we expect our customers to fall in love with us and our products, but we don't fall in love with them. And that's really profound because I think there's something fundamental about empathy that relies on humanity and equity. And I love the idea of truly bilateral relationships, of relationships among equals, and the idea that there should be for every action an equal and opposite reaction from my physics heritage. It's like, why-

Brian Pagán:

It's like Newtonian design.

Daniel Stillman:

Yeah, Newtonian design. It's like, and so now I get why it's in red, that the connection is so deeply important. And there's all these techniques that you have around it, like free writing and method acting, which I want to make sure we talk about. And that's why it's underlined in red, is that that's the step that you feel is missing in a traditional double diamond UX. Find a problem and then find a hole and then fill the hole process.

Brian Pagán:

And I will say another... If you don't mind, we'll just one more thing about the empathic design process. I don't necessarily see it as on a project level where you have a project that's discovery, immersion, connection, and detachment. I see the empathic design process very much as sort of a fractal kind of thing that can also apply within other stages of design processes. So for example, you just mentioned the double diamond. And the double diamond has four stages where you diverge and then converge and then diverge again and converge again. And within those stages, I feel like you can repeatedly do an empathic design process. It can be at every phase of a project. It can be every sprint. It can be every day. It can be that as a designer, you might be going through this process a few times a day as you're making decisions going forward through moving pixels.

Daniel Stillman:

It's fractal.

Brian Pagán:

It's very fractal in that sense. Yeah. Yeah. Yeah.

Daniel Stillman:

So two things I want to say. By the way, if Chantel, Erin, Jim, if you need to or want to break in at any point and say, if there's something unclear, you want to go deeper in something, you don't have to save your questions to the question. We're all equal humans here.

Daniel Stillman:

And I guess the second thing that's coming up for me, because maybe this is the thing that we wouldn't know about you if we Googled you, or maybe it is, is your acting experience. I mean, it's in the book, but I think the reason I'm interested in this is the idea that all of us can and maybe should, not to should anybody, can and should bring all of the parts of ourselves to the things that we're doing. And it's really interesting that because you have this acting heritage, you're like, "You know what this is like? This is like method acting," thought no one else ever. Right? And so I don't know if that's a question or a comment or just like a tell me more about that. And also just to anybody, for everyone, I think it's just, it's so valuable to be able to bring all the parts of yourself to a challenge. So kudos for doing that. And also tell us more about method acting for people who don't know about the method.

Brian Pagán:

The method. I love that. Yeah. So your question, I mean, answering your question is going to touch on so many things because in creating the book, it was exactly bringing different parts of myself and different interests that I had together into one space because I'm an actor, but I'm also, I practice mindfulness and I noticed a lot of things there that could be useful for design practice that aren't necessarily taught as part of a design practice, which I think is like a missed chance. And we talk a lot about empathy and we talk about empathizing with personas and with fictitious characters or characters in a product development cycle, but actors have been doing this for 3,000 years, three-and-a-half thousand, 4,000 years, or however long people have existed, they've pretended to be other people, and-

Daniel Stillman:

For fun.

Brian Pagán:

For fun. Yeah. Or for money or whatever. To precipitate social change. But there's already a really wide existence of techniques and almost a science that we can lean on and inform ourselves with that we're just not even paying attention to, which I think is a shame. So this is my attempt at a first, let's say, interconnection between those different disciplines, mindfulness, acting, and design.

Daniel Stillman:

Right, because this is... I was just in Greece for my honeymoon. And so I stood in one of these amphitheaters on the goddamn Acropolis.

Brian Pagán:

I'm jealous. Wow.

Daniel Stillman:

And you're like, "This is a place." Right? And it's been occupied on and off since prehistoric times, right? So it's like this little divot in the hillside just was used as a divot in the hillside, and then somebody put rocks in it so people could sit down and not give muddy, which was very nice. But this was the thing about personas. The word persona comes from persona, to speak through, because when they did these... When they acted, they used these masks that also helped them project their voices to the hundreds and hundreds of people. And I think personas are these things that are thrown around in the design field, and finding out the origin of this word persona, to speak through, was mind-blowing. So tell me what that sparks in you, Brian, because I heard you, just like your yes.

Brian Pagán:

Oh yeah, absolutely. I mean, it's by creating a persona or a character, we let our target audience speak to us. So yeah, I mean it... Wow. That's amazing. Yeah. Cool.

Daniel Stillman:

And maybe in terms of connection, if you were to choose, and this is a terrible question, one tool. If you were to choose one tool, what is your favorite tool for getting people to connect? When you talk about it as a field book and you talk about tools and techniques when you're teaching teams about how to be more creative in the way they connect for creative projects, what do you feel is the tool that people really find the greatest leverage or connection or ease in? And maybe also which one's the hardest and the most struggling, but that they should get better at?

Brian Pagán:

I think on the team level especially-

Daniel Stillman:

We can walk on two, both sides of that.

Brian Pagán:

For sure. I think the biggest... I hesitate to call it a connection technique because I think it's something that serves the entire inner loop, so it's for immersion and connection in that sense, but trigger cards and sensitizers as something that's in the book. These are... So if we look at the idea of sensitizers, any sensitizer is some sort of bit of information or some kind of story or some kind of personal thing that we share about someone in the targeted audience or in our group of people we're designing for, that allows us to emotionally connect with it. Somehow invites our resonance, our emotional resonance with that thing.

Brian Pagán:

And one of the ways that we can create sensitizers are trigger cards. And in the book, I show trigger cards from Melina Lopez Reyes who is a graduated master's student. And she did her project, her graduation project in Mexico around victims of domestic abuse. And what she found was that whenever she was working together with government officials or people who run associations or sort of volunteer organizations that help victims of domestic violence, they... In ideation sessions, it was helpful for her to sort of prime people with stories from her interviews. So she talked with a lot of different victims and made their stories really easily digestible with these little cards that people can use.

Brian Pagán:

So before an ideation session, she can distribute these cards to the participants of the ideation session, and either as part of the session itself or as part of the pre-read that before you actually join the session, you can go through and look at these trigger cards. And because they tell such intimate stories and real stories based on actual research, they allow us to emotionally resonate with what's going on and the experience of those people that we're actually going to be ideating for in the session itself.

Brian Pagán:

So for me, that's, I think, one of those measures or one of these techniques that takes very little effort and is quite easy to do, but it gives... The ROI is huge for this kind of thing. Does that answer your question?

Daniel Stillman:

Oh, it really does. My last question before I unleash the other brains in this room is what is not in the book but should be? Because I know that happened to me.

Brian Pagán:

Oh yeah, for sure. There's so many things. What's not in the book and should be? What is going to be in the expanded version is something about the hierarchy of spiritual intelligence from Cindy Wigglesworth. And going back to our earlier talking about humanity and recognizing shared humanity, Cindy Wigglesworth came up with this thing called this hierarchy of spiritual intelligence, which is basically four stages of connection between people going from apathy to compassion.

Brian Pagán:

So first it starts with apathy, like you don't care. It doesn't matter. Whatever. And then there's sympathy, which is not quite empathy, or you feel sorry for someone, but you're still not really opening yourself and being vulnerable to putting yourself on their shoes or even trying to relate to them on that level. Then after that is empathy, where we actually recognize each other's humanity, we actually try to connect our own experiences with the other person's experience. And then we have compassion, which is where we take our empathy and our feelings of wanting to help this person and actually put them into action and do something about it. This is where we build a house or help the person out or give a hug or these, whatever compassionate action it happens to be. Or design an app for them, or whatever kind of thing. These are the four stages, let's say, of from how you get to compassion.

Brian Pagán:

And just bringing those together and putting empathy in that context helps to understand that, one, if you can feel empathy for someone else, it basically forces you to recognize them as a human being and recognize their humanity because you're connecting your own experiences with their own too. So I think that's quite important and also shows that empathy can lead to compassion. It's hard to have compassion for someone if we don't have empathy for them first, if that makes sense. So those are the two key things that I'd like to bring in in the next version, let's say.

Daniel Stillman:

I think that's absolutely wonderful. Well, you answered all of my questions, so I'm going to pass the mic over to Erin first because she took the most copious notes in the Google slide stock that I shared. So Erin, what-

Brian Pagán:

Super cool. Thank you for that too, by the way.

Daniel Stillman:

Ditto, Erin, what is left in your mind that you want to unpack since we've got Brian here?

Erin Warner:

I know. That's great. Thank you. Thank you for this book, Brian. Yeah, I do have some questions, and maybe I'm sure they reflect where I'm coming from in my experience, but could you talk a little bit more about detachment? And you said that's in the standard repertoire of design, but I'm not really coming from that world, and so the word rings a little almost negative to me. Could you explain the purpose and the value of detachment?

Brian Pagán:

Absolutely. So as far as I understand it, the difference between immersion and detachment is just the fact that it's hard for us to look objectively almost at something if we're still immersed in another person's world. Another way to say it could be that empathy exists out of two different components. There's the affective emotional component, and then there's the cognitive more rational component. And if we have too much of one without the other, then it can either be dangerous if we have just emotional empathy without rational empathy. But it can also just go too shallowly. If we don't connect emotionally, then we're not going to... We're not really having true empathy in that sense.

Brian Pagán:

So I think by virtue of the fact that we go, we immerse ourselves in another person's world and then connect our own experiences with that, that's the inner loop. And then once we detach from that, then it gives us the psychological space and distance to be able to more effectively weigh the needs of the person in whom's world we just were immersed in, and everybody else, if that makes sense.

Brian Pagán:

So if I go into your world and I want to create something for you, if I'm still immersed in your world in my head while I'm trying to create something for you, then I'm going to forget everyone else, and I'm going to make something that works for you, even if it maybe exploits someone else. But if I can detach first, then it gives me that bird's eye view again where I can do something that helps you, but then I can also balance the needs of other people, the people around you, maybe people, other passive stakeholders of whatever I'm designing, in such a way that you are helped without trying to hurt someone else, if that makes sense. Does that answer your question?

Erin Warner:

Yeah, definitely. And actually, now that I hear you saying it, that was in the book. I read it. But then hearing you say it, connecting it directly to the detachment phase really clarifies. Thank you.

Brian Pagán:

Thanks. That's a good note. Maybe I should make that more explicit.

Daniel Stillman:

I'll give you the transcript, Brian. Chantel, Jim, just in terms of following that thread, is there anything more that you wanted to probe at on that topic or a different topic? But first, I want to see if there's anything deeper on that that's worth following. Because I'll just say one thing that's coming. Oh, wait, Jim, was that... I couldn't... Was that your mouth moving? I can't tell.

Jim Burke:

No, no, no. Go ahead. I have a completely different thread to go and disrupt everything with.

Daniel Stillman:

No, that's great. I was just designing the conversation. I was like, should we go deeper before we go other, elsewhere? It's-

Brian Pagán:

You've got the conversation canvas in front of your face, don't you Daniel? I know you're like looking at it. Which one am I-

Daniel Stillman:

It's on my brain.

Brian Pagán:

It's burned.

Daniel Stillman:

It's burned on my brain. One of the things that's coming up for me is the classic example of somebody coming to you and being like, "I'm sad" or "I'm upset." Just on the one-to-one conversation basis, on the human basis of like, "I'm sad. I'm having a hard time," and somebody goes, "You know what you should do is blank." Right? And that's going straight from the cognitive without any of the emotional resonance. It's like, "Oh, I'm so sorry you're going through that. That sounds hard."

Brian Pagán:

Yeah. I would even go as far as-

Daniel Stillman:

Wait, wait, wait, wait. Count to 10.

Brian Pagán:

I would even take it farther and say that a response like that is sympathy rather than empathy. Because it's easy to just come with solutions. I don't have to be vulnerable with that. I don't have to sit with you in your pain or in your trauma or in your experience in order to give you solutions. I just say, "Oh, you know what you should do? Just do that and that." It's real easy.

Daniel Stillman:

I read an article about that. You should read it.

Brian Pagán:

Here. I'll send you a podcast.

Daniel Stillman:

And I think the other thing that's important about detachment is that there are choices that have to be made in a creative project sometimes. Right?

Brian Pagán:

Yeah. Always.

Daniel Stillman:

And trade-offs. And I think that's sort of the classic trope of the designer, because that's where... He's like just fighting for the user and the customer, and you don't understand what they need. It's like, well... And then there's the trade-off of like, well, how will this be profitable? How will this be paid for? It's capitalism.

Brian Pagán:

When I teach-

Daniel Stillman:

Sorry, Erin.

Brian Pagán:

... beginning... When I teach basic UX, I have a slide on it with a... It's like a spider web with a little spider in the middle. And I like to talk about UX being in the middle of the web. We have to balance the needs of... On the outside edges of the web, there's developers and business and the user, and then there's people around the user, and then there's maybe legal team, and then there's maybe some experts or whatever. And we're like, we have to balance all that stuff. It's not just user advocate. We have to think of all these other things and like you say, make trade-offs and everything like that.

Daniel Stillman:

Right. And I'll just say, sorry for... But when I talk about that, that is that cloud three-way Venn diagram of user focus, business focus, and engineering focus. I'm like, those are people. Money people matter too. They have concerns and they need to be listened to, and sometimes their feelings need to be assuaged, and we have to empathize with them. And so the tech people, they're like, "I can't do that."

Brian Pagán:

Those poor money people.

Daniel Stillman:

Yeah, those poor money people. But there's people behind it where it's not just about... It is about finding appropriate balance between those three fundamental forces.

Brian Pagán:

Of course.

Daniel Stillman:

All right. I'll stop tirading.

Brian Pagán:

No, thanks for pointing that out. It's a good one.

Daniel Stillman:

Ladies first. Chantel, what's on your mind? What's important for you to bring into the conversation?

Chantel Botha:

So Brian, thank you for the book. I loved it. I skim read it. And Daniel said to me, "It's a light read. You're going to love it." And I really did. And I'm looking at the book more in the context of almost if someone said to me, "I've got a magic wand. What would I change in the world?" I would probably want to put just a whack load of kindness and empathy in the world. I really think we need a lot more of this. I mean, your book should be a prescribed book for every human on the planet, I think.

Brian Pagán:

Thank you.

Chantel Botha:

And it, I think it should be, I think empathy should be taught at school. So I've got two questions for you. So the first one is the emotional interest, how to escalate someone's emotional interest. Because what I see, and I operate a lot in the service environment teaching call center people and service professionals how to survive their jobs, and how to start thriving, and how to find passion, and how to unleash the human potential. And really what I see in that environment, there's a lot of people that have gone on autopilot. It takes a lot less energy. They don't really want to connect. They don't really want to feel if someone says to them, "You need to fill in this form." And the client replies, "You know what, I can't fill in the form. My son's sick and they need to go to the doctor." They pick, "We really need the form be because before we can do anything," rather than taking the bait and saying, "I'm so sorry to hear about your son." So I mean, a lot of what we see is energy conservation. So how can I create motivation for someone to want to connect and want to feel, because my value proposition is not very compelling. Yeah. Hey, feel some empathy. You're going to feel like shit. You're going to be sad. You're going to feel someone else's pain. And then what? Like...

Daniel Stillman:

We need to work on your sales pitch, Chantel. That's for sure.

Brian Pagán:

Absolutely.

Chantel Botha:

Daniel, do you have time for me? We can brainstorm it together.

Daniel Stillman:

We have Brian here. I think he's... Hopefully, he's going to help you find another entry point into the conversation.

Brian Pagán:

Nope. Empathy sucks. I'm leaving. No. I think it's a... I love that you gave me some context around it as well, because I think... So I have two, let's say, responses to the question or to the scenario. I would say the first response, if it's about creating that motivation, I feel like for most of us, obviously not for everyone, but for most of the human beings on the planet, we have this already inside us. We are born with the desire to be social, to understand people, to be kind to each other. And I would even go as far as to say that that's one of the reasons why we've survived while Neanderthals and other forms of humanity have died out is because we work together with each other. We help each other out. We take care of little babies and stuff. We don't just run around and hunting all day.

Brian Pagán:

So I think it's inside, and one way to I think help that happen for call center employees, for example, would be to create more space for them to allow them the time and the energy and the breaks and the recovery time to be able to actually do that kind of stuff, and listen, and be curious.

Brian Pagán:

Because of course I'm coming from a bunch of assumptions here. So if I say something that isn't true or isn't accurate, just please jump in and correct me. But I have the feeling that most of the customer service professions these days, a lot of times the companies look at customer service almost as bandaid or like a hygiene factor. It's like something they have to have, and they're not really passionate about it, and they're not interested in innovating around customer service. So the budgets for these kind of departments tend to be really low. And they say, "Okay, we need to hire a bunch of people, and they have a script, and they have the stuff that they need to do, and they just need to deal with it and stop bothering us with your problems."

Brian Pagán:

But if we give people, if we empower people to actually do things for people to help people out, and we give them the space to be able to recover from if they decide to immerse themselves in a person's world that they're talking to on the phone and listen to the fact that their son is sick and how is that affecting that person and how is it affecting their life and filling in the form and all that stuff. And like, "I get it. It's okay. Let's talk about it for a minute." If we can give them that space afterwards to be able to recover, then I think it makes it easier for them to actually do it. And especially if we model these behaviors, if we create a culture around listening and around non-judgmental observation, I think that could be helpful. But that is one. So that's one aspect of it is sort of taking away obstacles and letting it happen on its own.

Brian Pagán:

But if we're also trying to promote it a little bit, I think what we don't talk about enough might be this feeling of connection that we do get once the, let's say the climax happens and the sadness cloud sort of resolves, and the other person comes back and says, "You know what, thank you so much for this conversation. That really means a lot." Or "I feel much better having talked to you. Thank you for listening. This really, really just helped me feel better." And the feeling that you get when someone gives you that feedback is just amazing. And it costs time, it costs energy, it costs sadness, emotional, this journey, but it can be extremely rewarding. And think about if you do this 4, 5, 6 times a day, it's like a drug maybe. You'd feel really good. It's just this drug of helping people out and making people feel good and happy. That's amazing. Human connection. Yeah, we don't talk about that enough.

Chantel Botha:

And it's legal. It's a legal drug.

Brian Pagán:

It's legal even.

Chantel Botha:

I like that angle. I really do like that angle. I'm not sure how I would sell that up the hierarchy, because I think as the seniority and the pay grade gets more, I'm not sure that they're going to necessarily buy the legal drug. But thank you. Thank you for that perspective.

Chantel Botha:

I've got one more question for you. So if you had 60 minutes with a person that's very unempathetic, you've got a bundle of tricks and some magic sprinkle dust in your book, how would you... And I know you said earlier, we all have this inner, so we've kind of lost it a little bit. So let's just think about kind of the gem or the diamond that we've lost. But how would you in 60 minutes just reignite that empathy, flick on that switch? What would you do with a person?

Brian Pagán:

I hope you're not going to hate my answer. It's a typical coach answer, but I would listen first. Through going through a process of just listening and validating, listening and helping this person feel comfortable about what they're saying, helping them feel comfortable about what they're explaining about why they don't feel empathy or what holds them back, and accepting that for them, it's true. Even if I don't agree, it's for them, that's the reality that they're living with, and just observing that nonjudgmentally and creating space for them to sort of air out maybe some of the things that might be weighing on them that stands in their way.

Brian Pagán:

Sometimes it's enough for people to just get certain things off their chest or have articulated certain things maybe from their childhood. Maybe people don't understand that they went through this thing where, I don't know, their dad gave them a spanking because they were crying for some kind of thing. And boys don't cry. That's weak, or some kind of thing. That can have a huge impact on a kid in that moment. But then as they become an adult, that teaches them what's the worth of emotions and emotional intelligence. And if people are taught that empathy is bad, and emotions are bad, and crying is bad, and we shouldn't do this stuff, and you should be strong and don't show emotions or whatever, then there's a lot of baggage that they're working through. And just talking about it sometimes can help people open their own eyes, if that makes sense. Like just listening and letting them go through their own journey and sort of being there asking questions. I think that's the strategy that I would try to follow. Does that help? Does that make sense?

Daniel Stillman:

That's so insidious, Brian. I like that. Empathize with them until they crack.

Brian Pagán:

Yes. Kill them with kindness.

Daniel Stillman:

Kill them with... Well, yeah. Yeah. Jim?

Jim Burke:

Yes, sir.

Daniel Stillman:

What's on your mind? What's important for you to [crosstalk 00:39:15]?

Jim Burke:

So I want first, Daniel, I want to thank you for allowing us to come into your space and be part of this. This is awesome. As I read through Brian's book, there's a lot of things that I absolutely loved about the way that it was set up, because it was... It started with that diagram that you put up Daniel, the circle diagram. And the thing that I loved about that was it was more than, had me thinking that it's more than the hexagons for design thinking. By doing connection, when you look through, and I say the hexagons because when you go through empathize design, ideate, prototype, test, what you're talking about with empathy is really about a glue that binds those together. Because if you actually go through and if you're in academia and you're going through what's a part of ideate? What's a part of prototype? What's a part of test? Underneath everything is the connection that you're talking about, trying to connect with that user that you're designing to. So I love the fact that that, that circular diagram allowed us to be more than.

Jim Burke:

The other, the part that led then to the, I think it was an earlier chapter that you had which resonated with me, which was the product market fit side. I'm one of the denizens of Strategyzer and their Value Prop Canvas, and the Business Model Canvas. And the thing as a facilitator that I always... Not that I struggle with. I struggle with being in sessions where it's poorly facilitated, where it goes, "Oh, here's the Value Prop Canvas and we have the product, and we have the pains that people are doing. And here's your pain reliever, and the jobs that people do. And connect the dots and the skies will part and you'll have this thing because you filled out the rubric, therefore it must be so." When I start seeing that, and I loved your line in there. I loved creative empathy helps us achieve this by surfacing latent people's needs. Are there any suggestions that you would make on how to help surface those product market fit needs as you're designing, whether it's prompts or more probing questions?

Brian Pagán:

Both prompts and probing questions, I think... Yeah. So basically, everything in the proximity section, all the techniques in there and some of the ones in the team section as well, of course, but as a designer, working on something like myself, if I would be working like that, then I would try to use those techniques from the proximity session to be able to move myself into that head space or that emotional space while I'm actually designing something.

Brian Pagán:

So in the book I tell a story about when I was designing the interface, the UI for a breastfeeding tracker, for example. And I never breastfed. I never will breastfeed. It's not an experience that I have a lot of proximity with. But by doing this, it's a very simple exercise, but a free writing and character thing. Basically, I wrote... My acting coach gave me this exercise to pretend that I'm a new mom and I should write a letter to my newborn child. And that helped me really get into the head space of what it's like to be a new mom, a new parent who might be having some kind of anxieties around like, "Am I doing this right? Am I going to... I don't want to make you sick. You're such a fragile thing. I don't want you... I want to take care of you and I really love you, but I'm also scared. Like you're such a, you know, kind of thing."

Brian Pagán:

And just understanding that as part of my design process really helped me connect with the already existing research material that was there, but then on a much deeper, much more emotional level, so that it gave me not only the insight that things needed to be a lot simpler than I thought with the UI itself. But it also gave me a lot more confidence to fight for that simplicity within the team.

Brian Pagán:

And to give a very concrete example of this, at the bottom of those tracking screens in the app, there was a push to have content there, like articles that people could read. The assumption was that a mom while she's breastfeeding, wants to look at articles on her phone because she's bored or whatever. I thought, no, there's nothing boring about breastfeeding. It can be a very stressful thing. There's so much going on. We need to take this content out. We need to put the content in another place, serve it in a different way. And that one technique gave me sort of the ammunition and the ability to actually get that stuff taken out and placed in a more appropriate place. Does that answer your question?

Jim Burke:

Oh yeah. Yeah, it does. Thank you so much.

Brian Pagán:

Cool. Thank you.

Daniel Stillman:

Just to turn the crank on that a little bit, two things. One, I think that speaks to Chantel's question a little bit that one of the most powerful ways to create change is to have people get more proximity where the challenge is happening. And I've definitely done situations like this Chantel, where you bring people into the call center and they actually watch and listen while they go through it. And it's you increase the proximity. It's much harder to ignore what's going on.

Daniel Stillman:

But there's another thing which I really wanted to make sure we talked about, which is the first, second, and third person shifts that happen through the process. And when it comes to facilitating this process for others, Jim, which is what you're talking about specifically, like how do I help create a space where this can happen? The writing, the free writing is going back into the first person. It's not, she does this. She does that. She does this. It's trying to internalize it from the I do this. I do that. And even though I think there's some risks of stereotyping and not being, oversimplifying, it seems like making that intentional shift to the first person is a really important part of the connection step in creative empathy, like going back into the, like, to really inhabit.

Brian Pagán:

Absolutely. And that's exactly what that connection phase is all about, is really stepping into that world, becoming that person on some level. And whether it's in your head or whether it's as part of a simulator or something, it really personalizes it for yourself so that you really feel that connection. Indeed. Wow, you put it really wonderfully. Crap. I should put that in the book.

Daniel Stillman:

Well, Erin's moved locations, which means it's almost time for us to part. We only have a couple of minutes left, and I didn't design the close, which is kind of hilarious. Brian, is there anything else that we haven't asked you that we should ask you or anything else you want the people here or at home to know? That's the best I got right now.

Brian Pagán:

I'll say one last thing. It's a little bit more general than just from the book, but it's something that underpins everything in my entire life. So I'm convinced that every single choice that we make as people can be reduced to love versus fear. And the more we choose fear, the more easy it becomes to keep choosing fear. And the more we choose love, the easier it turns into keeping choosing love, or to keep choosing love. And the choice to listen, the choice to empathize with another person, the choice to be vulnerable and resonate and connect with another human being, it's that's a choice of love. And I want to help everyone that I possibly can to facilitate them in choosing love a lot more. Yes. Oh yes. It's all... That's the best. Yeah. Yeah.

Daniel Stillman:

Chantel has put on her heart sunglasses for those at home.

Brian Pagán:

Heart sunglasses.

Daniel Stillman:

And more Baby Yoda.

Brian Pagán:

Do love, you should.

Daniel Stillman:

So Brian, isn't this true that you do... So other things that people should know about you, which we didn't talk about. You do workshops on this stuff for teams and organizations, helping people get better at this.

Brian Pagán:

Absolutely.

Daniel Stillman:

Can people get a paperback version of the book? I know you sent me one, which was very sweet of you. Can they buy it from someplace else if they want to get it?

Brian Pagán:

I have a very strict pay what you want if you want policy for the paper book. So if you want a paper copy, just email me your address. I'll send it to you. And inside will be a little piece of paper with the QR code that if you want to make a donation or pay something... Those are another heart glasses. Oh man. That if you feel like giving something, you can, but it's totally optional. I really want this to be like a pay what you want if you want sort of give me what you think this is worth kind of scenario. And yes, I do give workshops on this for larger teams, smaller teams, at events, in-house like for companies, lots of trainings and stuff. Yeah. I definitely. It's a lot of fun too.

Daniel Stillman:

And people can find you at the URL that you're going to specify now.

Brian Pagán:

Thegreatness.studio, at The Greatness Studio, or especially for creative empathy, it's just creativeempathy.eu.

Daniel Stillman:

There you go. Easy. Well, with two minutes to spare, Chantel, Erin, Jim, what's one word you're checking out with?

Jim Burke:

Excited.

Chantel Botha:

Bold with joy. Thank you, Brian. I loved this conversation.

Daniel Stillman:

That's five words, but we'll allow it. Erin, what are you checking out with?

Erin Warner:

Oh, the positive residence of detachment for the holistic picture.

Daniel Stillman:

That's a good tattoo. I'm in for it. Brian, thank you so much for making time to have this conversation. Erin, Chantel, Jim, thanks for lending your brains to this delicious soup. This is really delightful. What a nice way to start my day. So thank you very much, everyone.

Brian Pagán:

Thank you all. This was amazing. I appreciate it.

Jim Burke:

Thank you all for having us. Thank you so much.

Chantel Botha:

Thank you.

Jim Burke:

Thank you, Brian.

Daniel Stillman:

Thank you, Brian.

Jim Burke:

Fantastic to meet you and be part of this.

Brian Pagán:

Absolutely. Thank you very much. Let's stay in touch.

Jim Burke:

Will do.

Daniel Stillman:

I'll call scene. And scene.

Brian Pagán:

And scene. Thank you all. Amazing. I appreciate it. So cool.

Daniel Stillman:

Thanks, Brian. All right. Have a good day, everyone.

Jim Burke:

Take care.

Erin Warner:

So cool to get to talk to the author, so thank you very much for this opportunity.

Daniel Stillman:

Thank you.

Brian Pagán:

And if you want a paper copy, let me know. Really. I'll send it. It's all good.

Erin Warner:

I think I do. I think I need to read it again, but thank you.

Brian Pagán:

Thanks.

Erin Warner:

Thanks, Daniel.

Daniel Stillman:

Thanks Brian. Talk to you soon. Hey, man. Thanks for doing that.

Brian Pagán:

Thanks for all-