Reunion: Leadership and Creating a Culture of Belonging

Rabbi Tarfon said: The day is short, and the work is plentiful…It is not your duty to finish the work, but neither are you at liberty to neglect it. 

(Pirkei Avot 2:15-16)

My conversation today with Jerry Colonna closes with him paraphrasing this powerful notion - and the work we are discussing is the work on yourself and the work to create a better world - one where everyone feels like they truly belong. In a world where many organizations are retreating from Diversity, Equity, Inclusion and Belonging initiatives, I’m grateful that Jerry is leaning into this conversation. I see the work of antiracism as firmly in the realm of what my peoples call Tikkun Olam, repairing the world.

It’s absolutely essential that men in positions of power and especially men who present as White, do not neglect this work. 

Jerry is a graduate of Queens College and a Brooklyn native.

Jerry helps people lead with humanity and equanimity. His unique blend of Buddhism, Jungian therapy, and entrepreneurial know-how has made him a sought-after coach and leader, working with some of the largest firms in the country.

In his work as a coach, he draws on his experience in Venture Capital as Co-founder of Flatiron Partners, one of the most successful early-stage investment programs. Later, he was a partner with J.P. Morgan Partners, the private equity arm of J.P. Morgan Chase.

As a partner with J.P. Morgan Chase, Jerry launched the Financial Recovery Fund with The Partnership for the City of New York, a $10 million-plus program aimed at creating grants for small businesses impacted by the attacks on the World Trade Center.

Along with a strong commitment to the nonprofit sector, Jerry is the author of two books: REBOOT: Leadership and the Art of Growing Up (2019) and REUNION: Leadership and the Longing to Belong. (2023)

Reboot was met with critical acclaim, stirring up a big question in the hearts and minds of people: “How have I been complicit in creating the conditions I say I don’t want?” Jerry’s second book builds on this question, asking us what benefit we get from the conditions we say we don’t want - the systems of oppression that those who have eyes to see, can see.

Reunion is a highly personal book that asks us all to examine our history of longing to belong - and the ways in which we have been excluded or excluded others.

Key Threads in the Conversation

We discuss Jerry’s Journaling practice and how it is an essential conversation he has with himself, each morning. 

We explore what it means to be a “good man” - and how in his first book, REBOOT, he questioned whether he was a good man, while in REUNION, he built upon the assumption that he is a good man and explored (and expanded) what it means to be a good man in a world where there is division and polarization.

And I get Jerry to coach me on one of my favorite questions: understanding the disowned parts of ourselves, exploring the reasons behind disconnecting from them, and the importance of integrating them back without denying them - very much in line with the process of REUNION. All while working to authentically grow in ways that matter, without self-abuse or denial.

Those parts of ourselves we wrestle with wrestle back at us. Many leaders I coach want to be feel or been seen as more or less of some quality or another - they, like so many of us, feel they must be other than they are in order to belong.

In my experience, fighting against our parts without understanding and loving them is a losing battle. Jerry asks us to understand the stories behind our self doubt, and to honor the ways that part of us has sought to care for and protect us in the past.

I find great empathy and lovingkindness in spending time nurturing my denied parts and my clients do, too. I’m so grateful to absorb Jerry’s approach to self-integration, and to expand our inner work towards creating not just a life we love, but a world we want to live in.

Links, Quotes, Notes, and Resources

Reboot

Jerry’s profile at Reboot

Some other solid interviews with Jerry:

On Being with Kista Tippett: Can you really bring your whole self to work?

Noah Kagan, from AppSumo, interviewing Jerry on being a better human and a better leader

More About Jerry

A graduate of Queens College, Jerry helps people lead with humanity and equanimity. His unique blend of Buddhism, Jungian therapy, and entrepreneurial know-how has made him a sought-after coach and leader, working with some of the largest firms in the country.

In his work as a coach, he draws on his experience in Venture Capital (VC) as Co-founder of Flatiron Partners, one of the most successful, early-stage investment programs. Later, he was a partner with J.P. Morgan Partners (JPMP), the private equity arm of J.P. Morgan Chase.

As a partner with J.P. Morgan Chase, Jerry launched the Financial Recovery Fund with The Partnership for the City of New York, a $10 million-plus program aimed at creating grants for small businesses impacted by the attacks on the World Trade Center.

Along with a strong commitment to the nonprofit sector, Jerry is the author of two books: REBOOT: Leadership and the Art of Growing Up (2019) and REUNION: Leadership and the Longing to Belong. (2023)

Reboot was met with critical acclaim, stirring up a big question in the hearts and minds of people: “How have I been complicit in creating the conditions I say I don’t want?” Jerry’s second book builds on this question, asking us what benefit we get from the conditions we say we don’t want.

Jerry is astounded by the fact that he lives on a farm outside of Boulder, CO near the foothills of the Rockies, and far from the streets of Brooklyn where he was born and raised. He is the father of three amazing humans, each of whom cares deeply about the love, safety, and belonging of others.

AI Summary

• Jerry discusses his journaling practice, which he does every morning, and how it's a conversation he has with himself (4:58)

• Jerry discusses the continuity and progression between his past works and future plans, emphasizing the importance of living authentically and working through meaningful issues publicly. (10:22)

• Jerry explains that in Reboot he questioned whether he was a good man, while in Reunion he built upon the assumption that he is a good man and explored what it means to be a good man in a world where there is division and polarization (12:17)

• Jerry articulates his desire for transformation through openness to dialogue and self-reflection, aiming for individuals, especially those in positions of power, to recognize complicity and actively work towards positive change. (16:30)

• Daniel asks who Jerry wishes would read his book and go through the workshop, and Jerry responds that he hopes it will open hearts and minds to dialogue and radical self-inquiry (19:40)

• Jerry discusses the role of a coach in guiding clients, emphasizing the importance of telling clients what they need to hear rather than what they want to hear. (29:17)

• Daniel Stillman asks Jerry about his approach to coaching clients on difficult topics like equality and antiracism, and Jerry describes his imagery of being side by side with clients and offering guidance without letting ego get in the way (30:41)

• Jerry explains how he approaches pointing out instruction to clients and shares an example of helping a client confront accusations of exploiting unpaid or low-paid labor (34:20)

• Jerry Colonna delves into the process of reuniting with disowned parts of oneself, exploring the reasons behind disconnecting from certain aspects and the importance of integrating them back without denying them. (37:40)

• Daniel and Jerry touch upon the transformation of internal struggles into strengths, referencing the shift from ghosts to ancestors. (45:33)

• Jerry Colonna asks about the benefit of self-doubt and discusses how it can serve as a safety mechanism, potentially passed down through lineage (46:45)

• Jerry and Daniel discuss the danger of participating in the diminishment of oneself while emulating others, and emphasizes the importance of honoring and metabolizing teachings from elders (51:59)

Full AI Generated Transcript

Daniel Stillman 00:00

And I can welcome you officially to the conversation factory. Jerry, I actually really am grateful that you made the time for these open space conversations.

Jerry Colonna 00:08

Well, thank you for inviting me. It's really a joy and delight. I think you were kind enough to ask about what the experience has been about talking with folks, and I have to confess that I just enjoy it. So I'm looking forward to our conversation.

Daniel Stillman 00:29

Thanks, Jerry. There's so many places we could begin, but as a fellow native New Yorker, and there are plenty of us, whenever. This is a sidebar, I wasn't intending to go here, but I feel like whenever somebody's like, wow, you're really a native New Yorker. I've never met one. I'm like, I don't know. You talk to your bartenders. There's lots of us.

Daniel Stillman 00:50

There's a million kids in the New York City public school system, and you were one of them. So I loved the story of you journaling on the subway and discovering your voice and the power of connecting to your own voice. And I just was curious about what your journaling practice is like today. And if you continue to, if you recommend journaling in general to leaders as.

Jerry Colonna 01:17

A practice, well, here's my journal.

Jerry Colonna 01:24

Would I continue to recommend it? Well, what my journaling practice is is exactly what it was when I started at 13 years old. When I was 13, it was a different time of the day that I would do it more often than not. As YOu noted, I had this Long subway ride from Midwood, Brooklyn, to Ozone Park, Queens, and the train would take me into Fulton street, downtown Manhattan, where I'd switch to the a train, and then. So I would Take the entry.

Daniel Stillman 02:05

You're misusing your subway pass, if I recall.

Jerry Colonna 02:08

Do you recall well? You recall well. And I would pass the hours doing homework because it was about a 90 minutes, two hour ride each way, reading and journalIng. And the original journal was always a, you know, three ring binder that I was writing in loose leaf. Eventually, I graduated to bound volumes, probably in my twenties, and I continue to journal to this day. I will confess that my handwriting is so bad, I have dysgraphia, and I cannot go back in time and reread my own handwriting, which is an interesting experience. So it just keeps me very much in the present. And the experience of journaling is just something that, it's a conversation I have with myself.

Daniel Stillman 03:12

Yeah, I mean, I'm really glad you frame it that way. I think that is part of the beauty of it. But do you have a specific prescribed dose or cadence? Because you know, there's the artist's way method of coaching where it's like, you know, it's first thing in the day, three pages long hand, or do you just go to it when you're called to it? Is it a specific.

Jerry Colonna 03:36

Oh, I go to it every morning. Yeah. Every morning. My routine is, you know, I wake, I shower, I get myself awake, I have a cup of coffee, and I journal.

Speaker 3 03:52

Yeah.

Jerry Colonna 03:53

And I do that fairly religiously every day, and then I follow that with sitting meditation. And so from where I. From my experience, the totality of the experience, it takes an hour or so to do all that. It's just a lovely way to start my day.

Speaker 3 04:18

Yeah. Yeah.

Daniel Stillman 04:21

Do you recommend it to folks, to leaders that you work with who aren't doing it?

Jerry Colonna 04:28

I do. I'm not hard and fast about it. As with almost anything that I recommend, it comes with the same spirit as the Buddha once offered in a teaching, which was, try it. If it works for you, great. And if it doesn't work, that's fine.

Speaker 3 04:54

Yeah.

Jerry Colonna 04:56

When I read the equivalent of that in the buddhist teachings, I felt so relieved from the lack of dharma, lack of dogma. Dogma to the dharma that it felt very resonant to me. So that's the kind of attitude I try to take.

Speaker 3 05:14

Yeah, yeah.

Daniel Stillman 05:16

It has value, but it's not. We're not restrictive or dogmatic about it. I'm really curious. I'm going to follow the thread of having conversations with ourself. One of the. It's one thing that came up in your first book and in your second book was this idea of being a good man. And that's. And it seemed like sometimes that was something you were saying to yourself, like, where I'm not and I want to be. And other times, in the beginning of reunion, it's almost like you're telling yourself, like, I am a good man, and I claim it. And, you know, the state of masculinity in today's culture is, you know, an interesting. That's like a whole other conversation.

Jerry Colonna 06:05

Right.

Daniel Stillman 06:06

But I'm curious what it. What's important to you? And, boy, that, you know, my chest is a swirl with these feelings because, you know, being a good man, it's important to me. I want to feel like I'm a good man. What's important to you about being a good man? What does it mean to you to be a good man?

Jerry Colonna 06:27

Well, I can't help but acknowledge your feelings, which are what's behind the question. I mean, this movement that you noticed, if you will, from one book to the other, from reboot to reunion, includes this movement towards

Jerry Colonna 06:51

accepting, if you will, who I am. So let's give it a little bit of context, and then we'll circle back to the larger question.

Jerry Colonna 07:05

In reboot, you're referring to what I call the good man chapter, chapter nine, in which it essentially opens with me yet again debating the question, am I a good man? And the woman who is now my wife, Allie, saying to me, in effect, in an exasperated way, enough already. You're a good man. Stop it. Right, but. And then as that story progresses, and I share the story of encountering this toppled over oak tree in which I project all of those feelings into the tree and imagine the tree as a good man. And I begin a process of working through the notion that I may have done something wrong in my life. I may not have always lived up to my aspirations, I may continue to not always live up to my aspirations, but nevertheless, I am a good man. You're right. In reunion, I work from the assumption, because reunion was written

Jerry Colonna 08:28

simultaneous with the process that I was going to, whereas reboot was written retrospectively. With me looking backwards. In reunion, I again tackle the question of, what does it mean to be a good adult? What does it mean to be a good human? But I build upon the assumption that I am a good man and then ask the question, a deeper question, which is, what is the relationship to a good man in a world where our dividedness and polarization can lead to children being killed? And how can one define oneself as being good if one is not putting one's shoulder to the wheel to make the world safe for all, to feel loved, safe, and that they belong. So, you know, the way I've internalized that is I am a good man, and there is still work to be done.

Daniel Stillman 09:42

Yeah, I see, you know, in the introduction to reunion, which is a lovely book.

Jerry Colonna 09:50

Thank you.

Daniel Stillman 09:51

There's this idea of redoing our first works over and the Baldwin quote and Parker's perspective of, like, looking at our past works and finding them wanting. And I'm hearing you say, and I had thought myself, there's a thread between them. It's a broadening definition of what it means to be a good leader and to be a good man. So I'm wondering, do you see it? I'm hearing now it's a thread less than. It's a reboot or a reimagining.

Jerry Colonna 10:22

I think that that's right. I think that while I wasn't cognizant of it at the time. And while Parker and I had numerous conversations while I was writing reunion, he very much was my mentor during that process, as he's been for 20 years. There is a. I can look backwards and see the through line, the thread from the work that I was trying to do with reboot to the work that I'm trying to do with reunion. And while I'm not ready to talk about it yet, the work that I'm planning to do in the next book. And if you want to step back far enough and say, okay, so what is actually happening here? I would argue that what I'm doing is living out loud. Living. Working through issues that matter to me in a public space, because I think that that's of service to people.

Speaker 3 11:41

Yeah.

Jerry Colonna 11:42

You know, I'll make an addendum to all that. I'm working my way through the latest Wendell Berry book, and I'm blanking on the name of it. I would have to look it up for a second. I'll pause on that. And in this book, he is yet again re-examining race in America, but through the lens that is really important to him, which is what he would describe as a discrimination against farmers, a discrimination, if you will, against rural America. And he talks about the divide between urban and rural. And I see him working through the same themes, expanding on the themes of his past works, the same themes that he wrote about in The Hidden Womb, which he published in 1970. And so I would expand the definition of what does it mean to be a good man? To include being willing to do our first works over being willing to. To look back and say, there's more to be said here.

Speaker 3 13:03

Yeah. Yeah.

Daniel Stillman 13:06

It feels like, in a way, being a good man is a horizon.

Speaker 3 13:11

Right?

Daniel Stillman 13:11

It's not a.

Speaker 3 13:12

It's.

Daniel Stillman 13:12

I mean, in one sense, I hear the, like, the power of owning, I'm a good man, and I can relax and I don't have to doubt myself. But on the other hand, there's an aspect of being a good man that is like, continuous process of exploration, a continuous process of revisiting your assumptions, a continuous process of looking around and saying, what kind of world am I creating? What kind of a man blanks.

Jerry Colonna 13:39

You know, I think that. That. I think that's true. And because I'm feeling uncomfortable with it, I'll say that we're having a gendered conversation and an angle here. And I think there is a lot. There are some aspects of this that are reflective of the experience of many folks who identify as men. And there are some aspects of this that are more universal. And that's important because from the subtitle of reboot, as you know, is leadership in the art of growing up.

Jerry Colonna 14:23

The final line of the main body of text in reboot is. And with that, I mastered the art of growing up. And the reason I bring that back in is that what we're both talking about is a practice. What we're both talking about is the. The commitment to the art of growing up. And that's a really important but subtle point, because we can get too wrapped around the axle thinking that there is a point, as you point out, that it's a horizon. It's not a point in the landscape that you arrive at. And then you rest.

Speaker 3 15:11

Yeah, now.

Jerry Colonna 15:13

But there is. There is something liberating in being able to say, as my psychoanalysts used to say to me all the time, not bad, considering. Which is a very liberating thought. You're not bad, considering everything. Yeah, you're okay, you know? So I offer that.

Daniel Stillman 15:37

I appreciate that, you know, so many layers and threads to pull on, but in some sense, you refer to the second book as a workshop, and a workshop has a beginning, a middle, and an end, and there should be some sort of transformative experience that people feel, and we're changed at the end. That's the power of the workshop. And I'm wondering, like, who do you. Who do you wish would read the book and go through the workshop and feel transformed at the end? Like, what's your dream for the transformative power of this. This workshop in a. In a book?

Jerry Colonna 16:17

Well, I think with reunion, the one person I know was changed was me.

Speaker 3 16:26

Yeah.

Jerry Colonna 16:30

And you're right. The implication of using the framing of a workshop is that one is changed by the end. And before I can say who I would wish to be changed, let me talk a little bit about the change that I would want to see. The change that I would want to see is an openness to dialogue. It's really important to me that reunion. Reunion. Leadership and the longing to belong not be presented as a conversation-ender, read this, and then you're done. Far from it. My hope is that the transformation would be an opening of hearts and an opening of minds to consider the possibility that that which we. Those of us who hold power. Right. I identify as white, cisgender, straight male, and as such, I hold a certain amount of power that those of us who hold power in whatever situation we're coming from would recognize the possibility that there's a lot more work we need to do. And that the work is not about looking outward and explaining to somebody else how they're wrong, which we spend far too much time doing, exacerbating the divisions. But the work is to look back, and you'll recognize this word. To look back or this question and ask, how have I been complicit in creating the conditions? I say I don't want to look back and say, how have I been complicit in and benefited from the conditions in the world? I say I don't want to see. And most importantly, what am I willing to change? What am I willing to give up, do that I love in order to see the world that I really want to see exist?

Speaker 3 18:49

Yeah.

Jerry Colonna 18:51

So long. Statement made short. The workshop transformation that I hope to see is that people end with that question and start doing that form of the radical self inquiry.

Speaker 3 19:07

Hmm. Yeah.

Daniel Stillman 19:10

I think of the questions that are. There's this list of questions that I've been absorbing from you. What am I not saying that needs to be said, which I know is from your psychoanalyst. What am I saying that's not being heard? What am I saying that I'm not. What's being said that I'm not hearing? And then there are these other questions, like, how have I benefited from the suffering of others? What don't I want to find out about my ancestors? Have I seen no strangers? There's, like, there's. There's layers of questions that people can be asking themselves, but the. The question that's in me, I don't know if you've ever been, I'm guessing at some point in your life you've been to a Passover Seder. In my.

Jerry Colonna 19:50

I have, yeah.

Daniel Stillman 19:51

In my, in my. My tradition, there's these. These questions. There's a story of. Of the sons, the son. There's a son who says, like, well, you know, this happened to you. Like, this has nothing to do with me.

Jerry Colonna 20:08

Right.

Daniel Stillman 20:09

And there's a son that sort of separates himself from the question. Then there's the son who doesn't even know how to frame the question about, like, why is this night different from all other nights? I'm butchering the haggadah. I really didn't prepare to have this angle, but this is. I'm trying to find a pathway into asking you the question about what? About all the people who, who will not read this book, who aren't ready to ask these questions. I feel like there's. There's. I feel like everybody could benefit from reading this book, and many people, bless you, will not won't.

Jerry Colonna 20:41

And many people will stop reading after the first line. Right.

Daniel Stillman 20:45

And many people are with. Are retreating from diversity, equity, belonging, ESG, you mentioned. I'm grateful as well in the conversation. Like, there's a huge retreat from woke capitalism and all of these things, and it's people who don't want to ask these questions at all because they're uncomfortable questions.

Jerry Colonna 21:09

Yeah.

Daniel Stillman 21:11

And I appreciate you leaning into those questions and doing your work in that.

Jerry Colonna 21:17

Well, let's even add to the question. One of the women who wrote the essays in the afterward, Virginia, asks a very, very powerful question of her. After describing her family's joy and maintaining a family tree that goes all the way back to Switzerland, she asked the question, what happened to the queer folk in my family? Because they existed.

Jerry Colonna 21:48

Okay, so, yeah, let's unpack your question for a moment. You started off by asking what happens to the folks who don't read this book? And you also make the observation, which I completely agree with, that we have moved away, if you will, even in the time in which I started writing the book to where we are today,

Jerry Colonna 22:22

I did not imagine as divided as we were starting in, say, the summer of 2020, that we would actually get worse. And it is worse. It is worse. And, you know, it's a challenge. I asked before of the world at large, what am I willing to give up that I love in order to see the world that I know needs to be to come into fruition? So, Daniel, a lot of people loved REBOOT. A lot of people loved it.

Speaker 3 23:07

Yeah.

Jerry Colonna 23:08

Like, a surprising number of people loved that book. And still to this day, people, I was at a book event these last couple of days, and this woman comes up to me shaking with her worn copy of reboot, and she wants me to sign it. And I love that. I love it at a non ego based way, and I love it at an ego from my ego based way. And so what am I willing to give to up that I love? And what I'm willing to give up that I love is being the object of these wonderful and grandiose projections that somehow I have all the answers. But here's a larger truth, and it's implicit, if you will, in the quote from the Talmud in which I start chapter seven. I think it is in reunion. It is not yours. It is not mine to complete the work, but neither are we at liberty to neglect the work.

Speaker 3 24:18

Yeah.

Jerry Colonna 24:19

Right. So that look on your Face. Okay. We are not allowed to ignore the suffering.

Speaker 3 24:29

Yeah.

Jerry Colonna 24:31

Okay. We started off by talking about the good man. Okay? Our task from the divine. And I don't care which of the 84,000 doorways point you to the dharma, whether it's Judaism or Buddhism or Christianity or any other of the world's great wisdom traditions. They all point to the moral obligation to lift those who are oppressed, to welcome the other, to welcome the other, to see no stranger, and to welcome the wretched, to make space. You know, the other night, a woman came up to me because, you know, in reunion, I talk about being motivated by my daughter's participation in the protests over the murder of George Floyd. And she says to me in a kind of almost conspiratorial way, well, you know, black lives matter is anti semitic. And I looked at her and I said, there is anti semitism on the left. There is no question about that. But here's a news flash. There's anti semitism on the right. There is antisemitism everywhere, and there have been for millennia. This is not a phenomena of current times. And I don't know any other way to push up against systemic othering such as antisemitism, other than those of us who are not subject to the burdens of those things standing up and speaking out because it's wrong.

Speaker 3 26:31

Yeah.

Jerry Colonna 26:35

We know this.

Daniel Stillman 26:36

We know this. So one question I'd been sitting with was, as an executive coach myself, in my training, in my mentorship, my coaching mentor, Robert Ellis, said, like, I'm always a step behind you, and if you stop, I'll bump into you, but I don't know where you need to go. And I really appreciated the conversation you were having with one of your founders who was underpaying her employees and her interns, and you pushed back pretty hard on her and then pushed even further to, say, look into her heritage in tobacco farming and the long history of unsustainable economic models involving sharecropping and slavery and onward. And I feel like, in a way, as a coach, I want to be a step behind. And there's the asking telling spectrum. Like, I'm here just to ask questions, but there's a line where an ask becomes a tell, and you're like. And you're confronting them with a question that they don't really want to be asked. And I saw that as a real strong position to take as a coach to bring equality and anti racism and creating a positive world. Like, would you want your children to work at this company? What are the real externalities of your business model? And what kind of a world are you creating for future generations? These are hard questions. And that's not being a step behind. That is sometimes being a step or two ahead. And I don't know. My question is there. It seems like you do it with a lot of delicacy and respect, but also firmness and a little bit of force. So I'm just wondering how we manage this question of people who are not in the conversation, who are not thinking this way with themselves already there is an element of helping them get into the mode of these thoughts.

Jerry Colonna 29:06

I really love this question because it goes to the heart of how one can hold oneself as a coach in these spaces. So I want to recognize and honor what Robert said to you or says to you. And I think what he's saying in that is that the coach does not set the direction. And I would agree with that. The imagery that I feel more comfortable with than being behind is actually being side by side. And the imagery that I hold on to is I imagine myself oftentimes as in the passenger seat of a car being driven by the client. And my job might be to say, there's a pothole up ahead. I know that you can't see it, but I can see that pothole. You might want to make a left turn here.

Jerry Colonna 30:10

I think back to what my first coach supervisor once said to me, which I think is a really fundamental belief system and can be problematic. What she said to me is we tell our clients what they need to hear, not what they want to hear. Now, the problem with that is that we have to be careful of our own ego and our own narcissistic needs to be right.

Daniel Stillman 30:40

I don't know what you're talking about. I have no. That is an alien concept to me. I don't know.

Jerry Colonna 30:51

But there's something fierce about that. And then in the circumstance that you described in the example that I gave in the book, if you recall, the setup was really important. This client came to me not understanding why there was so much turmoil in her organization and what the accusations were against her. The accusations were that she was exploiting labor. Okay. The reason her entire staff quit was because they were exploiting labor. So my, in Buddhism, we call them pointing out instruction. My pointing out instruction didnt come, I think, from some deep place within me that said, let me set you straight. It came from an exploration that said, well, lets put the pieces together here. Youve been accused of exploiting unpaid or low paid labor such to the point that your company has now failed.

Speaker 3 32:06

Yeah.

Jerry Colonna 32:09

And by the way, the accusation was that there was a direct exploitation of non white folks and so the echoes were really worth looking at in that regard.

Daniel Stillman 32:26

Yeah. I mean, she had a central question, and she was looking here. And you're saying there's a bigger. That's circle that you're not looking here for this?

Jerry Colonna 32:38

That's right.

Daniel Stillman 32:39

The answer. The question you're looking for.

Jerry Colonna 32:41

There was a.

Daniel Stillman 32:41

It's true. She was. She was asking the question, why is this happening to me? And.

Jerry Colonna 32:47

Right.

Daniel Stillman 32:48

You're saying, hey, look, look a little.

Jerry Colonna 32:53

Well, it is what we should do as coaches. Right. When. So when a client says, why is this happening to me? And we are seeing a pattern, I don't think it is pushing. I don't think it's necessarily leading to be able to notice a potential pattern that's going on. I remember I used to have a client who used to complain about her boss named John, and I finally pointed out to her that her last two bosses were also named John and that her father's name was John and that the same complaint about all four men was occurring and so was I leading. Yeah, a little bit. But it's also like, you know, you've got a nail stuck out of you, stuck in your head.

Daniel Stillman 33:49

Right. I don't know if you've seen that video. It's a. It's a classic.

Jerry Colonna 33:52

I have.

Daniel Stillman 33:53

Yeah. It's like, I don't know if there's this throbbing. And this is the question of fixing versus not fixing, and also the question of, like, until we make the unconscious conscious.

Jerry Colonna 34:05

Right.

Daniel Stillman 34:05

It's gonna rule our lives, and we're gonna. We're gonna call it fate. And you're just pointing out patterns and seeing if they agree or disagree. We hold them lightly.

Jerry Colonna 34:15

That's right. Or if they resonate.

Speaker 3 34:16

Yeah.

Jerry Colonna 34:17

Or if they're. Or if they generate curiosity. Absolutely right.

Daniel Stillman 34:21

And if she had rejected it, then she would have rejected it. So there's another young quote I want to explore and a question that's been gnawing at me. It's a very ill formed, long winded tangle of a question, but I have an intuition that you will grok it and have an interesting perspective on it. And so this is just me getting some free coaching from you, if I can.

Jerry Colonna 34:47

Okay. Who said it was free? I'm sending you a bill at the end.

Daniel Stillman 34:52

Please do. So the other young quote you mentioned in your book is, we're not what happened to us, but what we choose to be.

Jerry Colonna 35:02

Actually, if I may, because I think the pronouns matter here.

Daniel Stillman 35:06

Oh, yes.

Jerry Colonna 35:07

He said, I am not what has happened to me. I am what I choose to be. Okay, yes, but keep going.

Daniel Stillman 35:15

Fair. No, no, because it's. It's. He's owning it.

Jerry Colonna 35:17

Right.

Daniel Stillman 35:17

And that. That's the difference. He's not proclaiming it for someone else. It's a choice that we make for ourselves.

Jerry Colonna 35:22

Mm hmm.

Speaker 3 35:22

Yeah.

Daniel Stillman 35:23

So, I, um. I was listening to your interview with Krista Tippett because I'm a huge Krista Tippett fan. I was re listening to it, and there was this phrase she used that didn't actually get picked up later in the conversation. What do we do with our own messiness? What do we do with the parts of ourselves we don't want to choose to be anymore? And something that comes up in my coaching work is the sense where there's parts of ourselves that we don't want to bring into a conversation. There's parts of ourselves that are. That we kind of want to other. That are ghosts to us, but they're still there. And I feel like there's a context. For example, one of my coaching clients feels the need to project a certain amount of confidence in fundraising conversations. And, of course, everyone has feelings of lack of confidence internally. And so there's this idea of showing up on purpose, of wanting to be. Be a certain way to shape the conversation in a way that we want to shape it. And not all our parts are safe in the conversation. And I guess I'm wondering, it's this idea of, like, self leadership and self management. How do we be these other ways without denying or othering these parts of ourselves? Because we don't want it to be a cognitive, performative act of playing.

Jerry Colonna 37:02

We don't want to fake it till we make it. Yes.

Daniel Stillman 37:05

That's in my notes. Right. And that's. That's like the classic, you know, Polonius, bad advice. Bad advice.

Jerry Colonna 37:12

Right.

Daniel Stillman 37:12

You know, Polonius, a terrible father, gives terrible advice to his okay, son. And so it's. To me, it feels like they're, you know, I want to befriend those parts of myself, but there's. And then we ask them to stay outside, but it still feels like there's this tension to other. These parts of ourselves and to make them unwelcome in these conversations.

Jerry Colonna 37:40

Well, I think I'm teasing through what the question is, so let me respond to that, because I'm seeing it not only Daniel as one coach to another, giving a perspective, but it's also for you, as well. So we'll hold both perspectives, and in a way, both of my books reboot, which is the book with which I was talking to Krista about, which I was talking to Krista about. And reunion. Address the need that's implicit behind your question in reunion, I think it's chapter four. It's the end of part one. So if we take a step back and we say that the basic theme of reunion is that in order to lay the ground work for what David White would call the house of belonging, one must reunite with a series of things, reunite with the truth of our ancestors, and not merely the myth. Reunite with those of our past, those of our ancestors who have been othered, and importantly, the parts of ourselves that we have dismembered from our own experience of us. And this is what's relevant. That's chapter four of the book, and in it, I quote extensively from an essay that Parker Palmer wrote about reuniting with the parts of ourselves. And again, that was a big theme in reboot. Okay, so if we go back to your example for a moment, this may feel like a subtle difference, but it's a little bit how I approach this question differently than, say, perhaps other coaches or perhaps other therapists or perhaps others. The making friends with parts of ourselves that we have dismembered. Okay. The process of reuniting with the parts of ourselves isn't, I think I'm thinking now of the parts work that Dick Schwartz teaches. I think that that is useful and important, but ultimately limited because it misses a very, very important element, which is behind the question of, how have I been complicit in creating the conditions I say I don't want? And that is the exploration behind why was this part of me dismembered? Because more often than not, I disconnect in order to feel loved, in order to feel safe, or in order to feel that I belong. Now, once. The first step is to recognize that there are parts of you that you have dismembered. The second step is to understand what was the cause of that dismembering. And the third step in the welcoming in is to understand that your wish for love, safety, and belonging is because you're human, not because you're broken. And so how do we transform the act of dismembering a part of ourselves, shoving it into the long black bag behind us, of the shadow that Robert Bly would call? How do we bring it back in and integrate it? Not simply by allowing ourselves to live out actions from our shadow, but, in effect, to eliminate the need to put things in the shadow in the first place.

Speaker 3 42:05

Yeah.

Jerry Colonna 42:08

That'S true. Reunion. That's not just living side by side in the same house that's actually bringing it back into relationship and welcoming it in.

Daniel Stillman 42:24

Yeah, it's a really interesting. And I appreciate that. I'm thinking of the. There's this Ts Eliot quote. The end of all our exploring will be to arrive where we started and to know the place.

Jerry Colonna 42:36

I almost used that quote. Almost used that quote in the book. I know the quote well.

Daniel Stillman 42:42

And in a way, what's tough is that there's still. We want to leave the feelings of self doubt outside the conversation, and we want to project confidence. And there's parts of us that feel a need to be seen as powerful, strong, lovable.

Jerry Colonna 43:05

But let me interject for a moment, please. How does the feeling of self doubt serve you?

Jerry Colonna 43:18

What is the benefit of the self doubt? You see what I'm doing there? You said, we want to leave the feelings of self doubt behind. And I'm actually asking a different question, which is, what is the benefit of doubting of oneself?

Daniel Stillman 43:41

It's safety.

Jerry Colonna 43:42

It's safety.

Daniel Stillman 43:44

Yeah.

Jerry Colonna 43:45

And if we look at the child that is in us, who was five years old, who, in order to feel safe, took on the responsibility of doubting one's own capability, because to be too confident was too risky. And that may be not only my interpretation of what I see all around me, but in fact, that might even be a lineage gift.

Speaker 3 44:15

Yeah.

Jerry Colonna 44:16

That might be something that grandparents felt and great grandparents felt. Because if I grew up, for example, in an environment of pogroms,

Jerry Colonna 44:32

did I just hit a nerve?

Daniel Stillman 44:34

Oh, yeah, sure.

Jerry Colonna 44:36

Then it's better to not stand out. It's safer to not stand out. And when I say safe, I don't just mean existential safety. I mean physically safe.

Speaker 3 44:52

Yeah.

Jerry Colonna 44:53

And so if that's the move, then what is needed is to be able to turn around and say, no matter how unsafe I feel, I am, in fact, safe.

Speaker 3 45:07

Yeah.

Jerry Colonna 45:09

Right. They are not coming with a knock on the door to take the whole family away. They did do that.

Jerry Colonna 45:20

But we are safe.

Speaker 3 45:22

Yeah.

Jerry Colonna 45:24

And so I can allow myself to feel the confidence of a fully grown, good man.

Daniel Stillman 45:33

Yeah. And that's the transformation of ghosts into ancestors.

Jerry Colonna 45:37

That's it. That's it. You got it.

Daniel Stillman 45:40

So what's really helpful about this, and I really appreciate you pulling it apart, is, you know, several years ago, I tried to write a. A second book and was blocked because, you know, my mother's gonna listen to this. So I. I don't want to say.

Jerry Colonna 45:59

God bless you, mom. We love you.

Daniel Stillman 46:01

I know that you had, you know, there was we controlled ourselves and parented ourselves in the family context because our houses were chaotic. Right. And so learning how to be things and to feel things and to be more mature than we are, to project what we don't feel internally and to create a shield of being a different way, there's a part of it that's numbing, and it's a kind of self murder. But in the flip side, I have, in my own experience scene when I was a 13 year old kid, I followed around this origami expert, Michael Schaller, on New York City. And I was an origami nerd. And this man was a short, loud, big personality, jewish man who could just own a whole room. And I was like, I learned how to be like Michael. I was like, look at him. And I think there is a beauty and a power. I wouldn't say faking it to till you make it, but seeing what someone else is and channeling them. So I think there's a beauty to that, but behind it is these feelings of self abnegation and numbing and denial and disunion. And I think this is where all of those are present and all of them are possible and true. And I think this is the sort of the question that's been. I appreciate you pulling away some threads at this with me.

Jerry Colonna 47:40

Well, you know, I really appreciate the story you share, Daniel. And I guess the question is, as you were talking about modeling yourself in some ways after Michael, I think of myself as modeling myself after, say, doctor Sayers, my first psychoanalyst, or Parker Palmer. And I think that there's something brilliant and beautiful about that. But it's not necessary to participate in the annihilation of your true self in order to internalize the lessons from others who come, who are mentors.

Speaker 3 48:18

Yeah.

Jerry Colonna 48:20

You know, Parker once wrote, there is nothing so tragic as to be complicit in the diminishment of our own self.

Speaker 3 48:27

Yeah.

Jerry Colonna 48:29

Right.

Speaker 3 48:29

Yeah.

Jerry Colonna 48:30

So, you know, but too often, I think, in the faking it till you make it, in the emulation of those we admire, we participate in the diminishment of our own self, seeing that as a necessary part of the emulation.

Speaker 3 48:56

Yeah.

Jerry Colonna 48:57

And it's. And it's just not true.

Speaker 3 49:01

Yeah. Yeah.

Daniel Stillman 49:02

So what I'm getting from this, what I'm learning is, and it's really great to hear in the ways that you've emulated and tried to project. You know, it's like, I want to be more blank, like blank is. And it's okay to do that if we use the other hand, to say, how can I nourish and care for and love the parts of me that don't. That don't feel that way.

Jerry Colonna 49:29

That's right. It's, you know, in a very practical way, I might be in the middle of a coaching conversation, and, you know, just as I just did with you, I might look away and stare off and say to myself, how would doctor Sayers respond?

Speaker 3 49:50

Yeah.

Jerry Colonna 49:51

Or how would Parker respond? Or how would Sharon Salzburg, my buddhist teacher, respond? And what I'm doing in that act to reference what I do in reunion. Sorry, we're getting. Our snow plows are here. What I'm doing in that act is taking. Is really referencing and taking in my elders who have come before me, and it's a. It's an act of honoring them.

Speaker 3 50:26

Yeah.

Jerry Colonna 50:27

To. To emulate what they have taught me. You know? I mean, Parker is 85. He's emulated Thomas Merton.

Speaker 3 50:38

Yeah.

Jerry Colonna 50:40

Right.

Jerry Colonna 50:48

You just don't have to participate in wiping out yourself in order to internalize your teachers.

Daniel Stillman 50:57

I think that's beautiful. It's a really beautiful way to put it. It's a really beautiful way of putting it. Sometimes I remind you, Daniel, you don't.

Jerry Colonna 51:07

Have to wipe yourself out to internalize anything. That feels like a teaching for me.

Speaker 3 51:14

Yeah. Yeah.

Jerry Colonna 51:16

In fact, the best way to honor whatever it is that you may have gotten from me is to metastasize it, is to metabolize it, is to take it in and make it your own.

Speaker 3 51:29

Yeah.

Daniel Stillman 51:30

Well, the thing that's coming up for me is the Mary Oliver poem, wild geese, which, you know, you do not have to be good, which is, like, such a relief for you do not.

Jerry Colonna 51:43

Have to walk for miles on your knees.

Daniel Stillman 51:46

You just have to love what the soft animal of your body loves.

Jerry Colonna 51:50

Amen.

Daniel Stillman 51:51

Amen. Well, it seems like we're very close to time, and that is probably a great place to stop. But I'll ask you, what haven't I asked you? Or what's unsaid that's worth saying with the few minutes we. We do have left. And I really appreciate all this time and consideration for these questions so far.

Jerry Colonna 52:11

What I would say is this, and here's a trigger warning. It's going to be about you. What a delightful conversation you've given me. What a gift you've given me with your questions, with your explorations, with your authentic whole self.

Jerry Colonna 52:37

Would that every conversation I have touch this level of depth. That would be a real joy.

Daniel Stillman 52:50

Thank you. I really appreciate that.

Jerry Colonna 52:57

I want you to know that I can feel how much my work has meant to you, and that is an honor to me.

Daniel Stillman 53:07

Thank you.

Jerry Colonna 53:07

So at the end of this, you're going to send me your address so I can send you a couple of signed copies of my books.

Daniel Stillman 53:14

Thank you very much. Well, as it turns out, you can also make coaches cry, not just CEO's.

Daniel Stillman 53:27

I really appreciate the time, Jerry. It's really been delightful. We'll include links to all the places where people can find all the things so that people can continue to do this work because it's really important work.

Jerry Colonna 53:39

And amen.

Daniel Stillman 53:40

That work is not the world.

Jerry Colonna 53:42

The world needs us to do our work. We are not at liberty to neglect the work, period.

Speaker 3 53:55

Yeah. Yeah.

Daniel Stillman 53:57

And the real work is internal work.

Jerry Colonna 54:01

Is inner work, always.

Speaker 3 54:03

Yeah. Yeah.

Daniel Stillman 54:08

Thank you so much, Jerry. It's really been. It's been a delight. It really, really has been. Have nothing else to add.

Jerry Colonna 54:16

That's a good note to end on.

Daniel Stillman 54:19

Beautiful. Well, I'll call scene then.

The Intentional Conversations that Build Powerful Co-founder Relationships

My guests today are Rei Wang and Anita Hossain, Co-founders of coaching platform The Grand, which was seed funded by Alexis Ohanian’s firm Seven Seven Six in 2023. Rei is the Chief Product Officer and Anita is the CEO.

I met Rei ages ago, in her early days in NYC at General Assembly, where she worked as a Product Manager and Global Community Lead, developing educational opportunities for students.

And I was excited to interview her about her work as the CEO of the Dorm Room fund at First Round Capital a few years back to get her perspectives around the intersection of community and product design…especially when the community IS the product. Check out that conversation here. Rei cultivated a vibrant startup ecosystem, mentoring over 250 entrepreneurs on various aspects of business management and fundraising. Their leadership garnered recognition, including the Forbes 30 under 30 award.

Rei and Anita met during their time at First Round Capital, where Anita was the Head of Knowledge. While there, she helped hundreds of entrepreneurs connect deeply and vulnerably, to share their concerns and to learn from each other. Anita was also an executive coach with the renowned coaching firm, Reboot, and is a certified Neuro-Linguistic Programming Practitioner.

Key Advice for Working Through Challenges

• Prevention is first and foremost! Speak early and often to reduce buildup, bottling up and boiling over of tensions

• Make feedback about actions and behaviors, not about the person or their personality

• Rei suggests that using a simple framework like SBIO is a great way to frame feedback. (Situation or data, the Behavior you see, the Impact it has on you, and the Opportunity for improvement or transformation)

• Make sure feedback conversations are two-sided, with both partners regularly asking for and offering feedback

• Anita underscores the importance of Co-Creation of resolutions to challenges instead of telling someone to be different. Working on these tensions with a sense of collaboration can lead to reduced defensiveness.

Links, Quotes, NOtes, and Resources

The Grand

My previous conversation with Rei Wang

More About Anita and Rei

About Rei Wang

I was born in China and lived with my grandparents and my great-grandmother all under one roof. My grandparents were teachers, lifelong learners, and culture bearers of our community. We constantly had neighbors of all ages over for tea and conversation. These discussions enriched my education.

I love building communities and designing learning experiences. I was an early Product Manager and the Global Community Lead for General Assembly where I created education products for thousands of students to pursue careers they love. More recently, I was at First Round Capital where I served as CEO of Dorm Room Fund. I nurtured a community of 250+ startups, and counseled entrepreneurs on topics ranging from fundraising to management. For my leadership on Dorm Room Fund, I received the Forbes 30 under 30 award.

About Anita Hossain Choudhry

My parents immigrated to the US from Bangladesh and found creative ways to share their life lessons through storytelling. I loved the stories so much I decided to share them by performing Bengali plays all around the country. Through these stories I gained valuable perspective and connected with a place my parents once called home.

I lead with curiosity and empathy which empowers others to find their voice. I launched a women's peer group at Deutsche Bank and a storytelling series for Wharton MBAs. Most recently, as the Head of Knowledge at First Round Capital, I helped hundreds of entrepreneurs connect deeply, candidly share their concerns, and learn from each other. My work on creating safe spaces is featured in the First Round Review. I’m also an executive coach formerly with Reboot and a certified Neuro-Linguistic Programming Practitioner.

The Grand is a culmination of my previous work experiences and inspired by my belief that everyone deserves group coaching and a supportive community.

A.i. Summary and Key Moments

The co-founders, Rei Wang and Anita Hossain discussed how they started their company, The Grand, which aims to address loneliness through consistent and vulnerable conversations within peer groups. They shared their insights around building a successful co-founder relationship, investing the time and effort to create intentional interactions, including fun outside of work. They emphasized the importance of frequent communication and intentional conversations to reduce tensions and misunderstandings. They emphasize the importance of frequent and honest feedback, coaching, and removing judgment in conflict resolution.

• Rei shares how they convinced Anita to start a company with them over the course of several months, comparing the process to a courtship 12:01

• The idea for The Grand came from their own experiences with loneliness and belonging, and their success in creating peer groups for open and vulnerable conversations among coworkers and founders (12:22)

• In their co-founder relationship, they prioritize connecting as whole humans and starting conversations with honest check-ins about how they're really doing, before diving into other topics. (15:18)

• Rei and Anita have frequent conversations throughout the day, which helps them address things earlier on and be more proactive in their communication (17:34)

• The co-founder relationship provides a unique outlet for constant communication about what's going on, how they're thinking and reflecting, and clarifying together. They also recognize the importance of coaching in being leaders and building a business. (23:26)

• Rei mentions the significance of sharing feedback frequently and openly to prevent resentment from building up. They also highlight the importance of framing feedback around specific behaviors rather than personal attributes. (28:18)

• Anita emphasized the importance of empathetic listening in co-founder relationships, where you seek to understand the other person's situation and ask open and honest questions. (31:07)

• Rei advised that forming a strong co-founder relationship takes time and intentional investment, suggesting activities like retreats and pilot projects to test working together in different capacities. Anita added that having fun together as individuals is also crucial in the co-founder relationship. (38:19)

Full A.I. Generated Transcript

Daniel Stillman 00:00

I'll re welcome you all to the conversation factory. Rei for the second time, and Anita for the first time. So I'm really grateful you made time for this, and I do still hope that I can learn from you in this conversation.

Rei Wang 00:12

Thank you so much for having us, Daniel. I'm excited to be you.

Daniel Stillman 00:16

Thank you. So I am curious how you two started the conversation about starting a company together. I know the grand has around for a while, and it started like all things do, I presume, as a conversation. So I'm wondering if you can just tell me a little bit about the seed conversation.

Rei Wang 00:39

Yeah, definitely. I'm happy to start telling the story, Anita, and feel free to jump in. It was actually a series of many conversations. So Anita and I have both started at first round at similar times back in. Gosh, Anita, I think 2015 feels like a decade ago.

Daniel Stillman 01:02

I mean, that is actually almost a decade ago.

Anita 01:04

Almost is a decade, right?

Rei Wang 01:09

I can't believe it. So Anita and I had became friends through work and just developed a close relationship. And I'd always known that I wanted to start a company, and I knew that it was important for me to start a company with people that I really enjoyed working with. Right. Because that would keep me motivated and energized through the ups and downs of company building. And after a few years of working at first round, working with Anita, I was like, I think I want to start a company with. So we used to go to the Boba guys in, you know, just for coffee, tea breaks during work. So I asked Anita one day if she wanted to get Boba. And after we got some Boba, I asked her, I was like, hey, Anita, you want to start a company with me? She's like, you're crazy what we even do together. And I rattled off a bunch of ideas, and she was like, no, I'm not convinced by any of. But I didn't take no for an over. Over the next, gosh, I'd say, like six months to a year. I can't remember exactly how long it was. Anita.

Anita 02:24

Yeah, probably very long.

Rei Wang 02:29

Where, you know, I just kept on asking Anita if she wanted to go get Boba or go get lunch, and then asking her again if she wanted to start a company with me. And being fairly relentless, know, just working together and was hoping to kind of change her mind and convince her that we could do something really great together. And I remember the day that she finally said yes. We had just gone on a company off site where we went curling at the Oakland ICE, and I don't know what it was about? Curling. After we went curling, we went for a walk around Lake Merritt, which is where I used to live in Oakland, and we sat on the grass and Anita was like, okay, Rei, I'll do it. Finally said, you know, it felt like a proposal moment when someone finally says yes. And I was elated and super excited to start this journey together.

Daniel Stillman 03:34

What made you want to propose to her and to be so persistent, why did you want to start a company with Anita? I mean, obviously she's wonderful. There's lots of, I can make up my own reasons, but I'm curious, what made you say she's co founder material?

Rei Wang 03:51

Yeah, that's a really good know. I think going back to the point of, I think a lot of people start companies because they're excited about the problem space or about the market they're tackling. And while I know those things are important, for me, it was really just being excited about who I was working with. And I think over the past three years that Anita and I had worked together, at that point, we had just developed a great relationship. I really felt like I could trust her, I could confide in her. She'd helped me navigate a bunch of different kind of challenges through work and life, and I felt like we could have honest communication and a really great partnership. So to me, I think that was the signs of a great co founder relationship and why I wanted to propose to her.

Daniel Stillman 04:44

Anita, what's your version of this story? I'm really curious what your experience was like.

Anita 04:48

Yeah, that is a beautiful story. Thank you, Rei. My version is a little different, and I would highlight that. I do think there are two types of founders, ones who know they want to be a founder and they want to start a company. And I'd say, Rei was in that camp. And then there's other folks who almost need to be a founder and don't want to be. So that was the camp that I was in. I will paint the was, you know, working at first round Capital, I had become an executive coach, working with Founders Day in and day out, and I really did not want to be a founder seeing it firsthand, unless I felt like I could really dig into an area that I was super passionate about, and I can spend the next seven to ten years working on it. And if I felt like I was uniquely suited to solve that problem. And so that's why I avoided being a founder for some time, just knowing the reality of it. Until Rei and I had these walks and these conversations. And the way I remember it is we had this deep level of trust with one another. Like Rei said, we were confidants for each other, and so we knew that we would work well together in that way. But it was the problem space and our values that we aligned on. And we talked a lot about problems that we saw that we wanted to do something about. And we kept coming back to loneliness, and we bonded over our own experiences. Being first generation immigrants in the US and what that experience was like and our own firsthand experiences with belonging or not belonging. And that's really what helped me understand, okay, we have this level of trust. We also have the same values, and we've also found a space that we can spend a lot of time in and make our mark on the world. And so that's really what it was for. Yeah. And the rest is history. And, yeah, I still remember that day in Oakland. We have a picture of it. It did feel like a momentous day for us, for sure.

Daniel Stillman 07:08

That's really what. What's coming up for me is loneliness and belonging are such big challenges, and there's so many ways to approach that challenge. So I'm curious, from your perspective, Anita. And I love this idea that, God, this is a hard job. I know it firsthand because I'm sitting with people who are solving this challenge every day. And to find not just a problem space that you wanted to lean into, but a way to address it is so interesting. So, for you, how did the grand come out of

Daniel Stillman 07:52

that sort of challenge you saw of loneliness? And.

Anita 07:57

So, you know, we talked about our firsthand experience with it throughout our lives growing up. And in particular, when Rei and I both moved to San Francisco, we both started in a job in an industry that we'd never worked in before. And so if we were left to our own devices and not able to talk to anyone about it, it could be very lonely, because you question everything, like, am I good enough? Am I doing the right thing? And we opened up to each other in this way, and that was really powerful, just this realization that I'm not the only one who has these thoughts. And over time, what we did is we gathered a group of coworkers to have monthly conversations on a consistent basis where we had this real talk and really talked about the self talk or the things that we were telling ourselves and really helped each other become more confident in our roles. That was such a powerful model. We also took that to the founders we worked with. And so we'd create peer groups. And again, these founders at first would come in and thinking they have to perform and say things like, I'm crushing it, everything's going really well, when in reality we knew that that wasn't true and it also wasn't helpful. And so we designed experiences and guiding principles that really helped people share more openly and more vulnerably and talk about the things on their mind, like, am I good enough as a founder? And that is when things shifted and we realized that there is something here, but only top. When you think about executive coaching and you think about these peer groups, only top executives or founders can get access to that. What would it look like if we can create something where people across ages, geographies, roles, can get that level of peer support when they need it most, so that no one has to walk through life alone and ultimately can become what we say, the grandest version of themselves.

Daniel Stillman 10:12

The power of, you mentioned consistency in conversations and self talk, the power of looking at yourself talk and going from surface level talk to real talk. And so I really want to focus the attention away from the product and how you two live those principles, because I've seen the event that I went to, we were talking about, I guess it was several weeks ago. Now, I know, and from my conversations with both of you in the past, I know that intentional conversations matter so much to you. And I'm curious what that looks like on a week to week basis. Because we scheduled this time, we wasted some of your time on technical difficulties. But normally you would be meeting on Thursdays to have your conversation just for each other. What would you be talking about now? How would you be designing this conversation? What would you be making sure you're attending to in your co founder relationship?

Anita 11:23

Rei, do you want to go first?

Daniel Stillman 11:25

I know it was a big question. Nobody wants to jump in on that one.

Rei Wang 11:30

Go for it, Anita. I'll jump in after you.

Anita 11:33

I would say the main thing about our relationship and our conversations and what drew us to each other is we connect as whole humans and not just as colleagues or co founders. And so the container of our conversations always start with, how are you really as a person? And we have a space to do that. Sometimes we do it through rituals like red, yellow, green, check ins, which is a stoplight analogy. Green means you're here, you're totally present. Yellow means you're here, but there's something lingering on your mind. And red means you're physically here, but your head is completely elsewhere. And the goal isn't to be green all the time. The goal is to just be honest about where you're at. And check in with yourself, but also with each other. We presume that everyone's checking in green all the time, and if they're a little distracted or short or whatever, we fill in the blanks and make up our own story. And so how can we have that honest connection in the beginning of any of our conversations so that we know the starting point and then we can get into two other topics, and so that's very important for us.

Daniel Stillman 12:53

Yeah, how we begin is so important.

Rei Wang 12:56

Yeah. Plus one to everything Anita said. Well, also, I think another important thing to know is just the frequency that we communicate with each. You know, Anita and I will probably just pick up the phone and call each other three to four times a. You know, we hardly go a couple hours without talking to each other. And I think that's fairly unique for co founders, especially for remote co founders. But we're constantly checking in with each other about questions, decisions, ideas, feedback throughout the day. And I think that helps too. If you're just meeting once a week for a one on one, then you feel a need to kind of prioritize and only talk about the most important things. And you don't get to dig into all of the topics that are top of mind. But I think having this level of frequency, we're able to kind of address things earlier on, be more proactive in our communication, so that way things don't bubble up into much larger challenges or topics of discussion, but rather ones that we can discuss quickly together and come.

Daniel Stillman 14:08

To a solution or agreement on that is fairly frequent. I'm curious how you distinguish between today is a special day and a special conversation. Like there's more intention versus the. I guess I'm wondering about logistical, emergent, reactive, proactive conversations versus intentional strategic conversations and how the week might be divided up. Or is it just like it is a steady stream of conversation and each one has the same sort of human energy behind it? I feel like I'm not asking the right question here, but maybe you can guess what I'm trying to get at.

Anita 14:59

Yeah, I would say a lot of, yeah, go ahead, Rei.

Rei Wang 15:06

This is hard without.

Daniel Stillman 15:07

I know. Yeah, it's like you can't point, you can't put your finger on your nose and say, not it.

Anita 15:12

You Rei!

Daniel Stillman 15:15

Yeah, you've got the floor, Rei.

Rei Wang 15:18

Okay, sounds is, I would say it's a steady stream with kind of maybe strategic milestones or checkpoints along the way. I think because we're talking to their so frequently, we'll say, hey, I think we need to have a strategy alignment conversation. Let's schedule that for Thursday and then also on the calendar to really dig into it and have more of a prepared agenda for that conversation, especially if we're trying to reach alignment. But other times, I think the conversations are more organic. Sometimes Anita will call, we'll talk about something for five minutes. Other times a five minute conversation will turn into an hour long one, and we'll end up having more philosophical conversation rather than a tactical conversation. Right. And I think it's just having that relationship, knowing kind of what we need, what the other person needs, but also being able to be clear about what our capacity for conversation is, too. And Anita is a mom of two, and we've all got kind of busy lives going on. So knowing, like today, I just have ten minutes to talk through this, but I can chat about this Thursday after six post bedtime and dig into it further. And being able to set kind of those boundaries with each other is also important.

Daniel Stillman 16:49

What did you want to add to that, Anita?

Anita 16:52

Yeah, so just going in a slightly different direction. One thing that I've noticed about our relationship and our conversations is we almost act as each other's emotional thermostats. And that is really critical in a co founder relationship because there are so many ups and downs you deal with on a daily basis. So to be able to have this safe space with each other where one of us might be feeling stressed or down about something and the other person is able to bring the other back up, it's really nice to have that relationship. And I do think us having worked together before contributes to that and really helps that.

Daniel Stillman 17:37

Can you talk a little bit more about this idea of being an emotional thermostat? Because on one hand, telling somebody your challenges can make them feel better. But I also, I'm sure you know, the experience of being bright sighted when you share a challenge with someone, and that doesn't sound like what you're talking about, but it does sound like co regulation, like having someone else who you really can tell everything that's going on creates homeostasis in your dialogue overall in the body of your relationship.

Anita 18:10

Exactly. I think you put it beautifully, and that's exactly right. When you're building a company, there are obviously, you have your team, you have your investors, you have your customers. Just having that relationship with each other and that co regulation that you talked about is so critical to face the day to day challenges that inevitably come up.

Daniel Stillman 18:34

This is something that I think is so interesting and unique about the co founder relationship. And, you know, this obviously, Anita, as a coach, sometimes the way I talk about it is that a founder, really your wife or your husband, can't be the person who hears all your problems all the time. You can't tell everything to your board. You are trying to sort of control the messaging around what's going on to various other people who are in the organization. And there is rarely a person who you can tell everything to, the good, the bad and the ugly, except for an executive coach. And it sounds like, in a way, the two of you provide this very unique outlet for constant communication about what's going on, how you're thinking and reflecting and clarifying together, which makes me think, why doesn't everyone have a co founder?

Anita 19:32

Yeah, that's a really good point. And, Rei, part of our relationship, early days, when you were trying to find a coach, we had that relationship. I don't know if you want to speak to that at all.

Rei Wang 19:49

Yeah, definitely. I mean, I think what is unique about our relationship is we're two co founders who are starting a coaching company, right? So we definitely know the importance to being collaborators, to building a business, to building a great product. And going back to the early days, I mentioned that I knew I wanted and needed to be my co founder because we had built that relationship of trust. And I had gone to her with a lot of the challenges that I was navigating in work and life at the time. And she was able to ask me really thoughtful questions to help me kind of process and find the answers within myself. So we've always had that foundation and we have different personalities in that we're able to kind of, I think, adapt to sort of what each other is feeling and provide kind of that alternate point of view and that balance to each other, too. So that way we can help see each other, see those new perspectives and kind of create that happy, perfect 72 deg temperature where we can all flourish and grow and do our best work.

Daniel Stillman 21:04

Yeah. Rei, I'm wondering, you mentioned, oh, we need to have an alignment conversation, or each one of you sounds like you can sort of call an audible, for lack of a. I mean, it's a sports metaphor. I'm not too good with those. But to sort of say what you feel needs to happen. And I'm wondering, from your perspective, I know that you are a very intentional conversation designer as well. How do you feel like you approach the structure of some of these more specific conversations that the two of you might call for? Say, let's have a conversation about blank, and let's actually have an agenda and approach it. How do you think through designing those conversations?

Rei Wang 21:51

Yeah, that's a great question. I think the first thing is to really align on the goal of the, you know, similar to how Anita kicked off our conversation today. Before we hit record, just asking, what do we want to accomplish from this conversation? What is the objective here and where are we trying to go in terms of destination? So outlining what that focus is, what the goals are, and using that to kind of set the context and frame the conversation and then also categorizing what type of conversation we're having. Is this an ideation conversation where we're trying to come up with new potential solutions, or is this a decision making conversation where we're trying to reach clarity and make a critical decision? Is this a feedback conversation where we're both trying to gain developmental feedback for each other, for our teams? Being really clear about what type of conversation you're having and what the purpose is, is the first step to making sure that you have a productive, intentional conversation.

Daniel Stillman 22:56

Yeah. Nita, I'm wondering if one of the things that I'm hearing, and I think this can always be, I think it's an interesting balancing act, is so much co creation and so know in dialogue and deliberation, but you two have different roles. Rei is the chief product officer and you are the. And like, I'm wondering how you separate whose job is what and whose decision rights are what. Or is it really just everything is dialogical and as co founders, it's something that everyone needs to sort of come into a decision together.

Anita 23:40

Yeah, that's a great question. I would say when we think about our roles, we come together first as co founders. And like Rei talked about, if there's a big decision we need to make and through our conversations we usually are able to get to alignment. And if for whatever reason we aren't, then Rei's done a good job of really creating the space for me to set the strategy and vision. But normally as co founders, we get to a point of alignment because we're not precious about, oh, it's my idea, your idea. It's really what's the greater good for the company, for the space, for our team. And when you have that baseline intention, I think you can get to where you want to go. And that's the most important thing about our relationship and how we delineate the decisions we need to make.

Daniel Stillman 24:38

Yeah. Did you want to say more about that, Rei? I think it comes up for you on that question.

Rei Wang 24:42

Sure. Yeah. I think this is a really important question and one that co founders need to figure out early on, but also check in continuously in their journey. And I think this has, has evolved for us a lot over the four years that we've been building the grant. So I'd say in the early days when we were just a team of two, every single meeting together was both of us. Right. And we would talk through every single decision together. Now we're a little bit bigger. We've got nine full time employees, six of which are on the product team, three of which are on the revenue team. So it's pretty clear these days where we focus our time. I spend most of my time working with the product team thinking about new features that we can release to make our experience for coaches, for members, for sponsors better and make sure that we're delivering a world class product experience. And Anita is really spending her time with the revenue team thinking about sales and marketing and go to market and how do we continue to bring in new business for the company. So I feel like these days we have more purview over kind of managing our teams and working with them to kind of deliver our goals and our results. And of course, we still come together a lot as co founders, but we're no longer in every single meeting together because we have to scale ourselves as our companies and our business and our team start to scale, too.

Daniel Stillman 26:19

Yeah, that's a really interesting inflection point moment that you're in where part of me feels like a little like I don't want to project, but it's like, it's a little sadness of this moment from like, wow, it's just like the two of us in everything altogether to like, I feel a little bit of a sense of loss of. Not that it's not okay to trust that person, but it's an interesting moment when you no longer have visibility to all of those things anymore.

Rei Wang 26:51

Yeah, I think there's definitely a lot of nostalgia. I mean, Anita and I like to reminisce on the early days when we would just work from her living room and it was very intimate and casual and cozy. But I think there's also great things that happen as you start to grow and scale too, which is we don't have to be responsible for making every single decision. Right. So I think that emotional burden starts to shift too, because you feel like, okay, I've got a team that I can delegate to. I've got a partner who I trust who's running another team and they're taking care of this too. So you no longer feel like that pressure solely weighs on you or on the two of you.

Daniel Stillman 27:33

I think that's a great reframe. I love that. So the two of you work with a lot of founders, and I'm curious, based on the way you think about your co founder relationship, it doesn't always go smoothly. People do have conflict, and I'm curious how you two think about working through conflict and if there's any coaching or advice you would offer to other co founders who are facing a moment of tension. And maybe I'll start with you, Anita.

Rei Wang 28:09

I'm happy to.

Daniel Stillman 28:10

Oh, Rei. Rei wants to jump in. Go for it.

Rei Wang 28:15

Okay. I'm happy to start on this one. So I think this is one of the most important topics and one of the most common topics that we see. Co founder relationships, business breakups are one of the things that we hear about most. I think, to me, the most important thing is to share that feedback frequently and often, and not to let things fester. I think oftentimes when you don't kind of discuss openly and honestly what's happening with your co founder, you start to kind of build resentment or it starts to kind of turn into a much larger conversation. So going back to kind of our communication practices, the fact that we can call each other three times a day and just very candidly say, hey, I have some thoughts about that meeting. Here's my feedback on how I thought it could be better. Or I have some thoughts on the way that you framed this conversation. Next time, could you try framing it this way? Because we have that relationship and we talk to each other so often, nothing feels like it's been kind of bottled up and boiling over, and it doesn't turn into a large point of tension or a large argument. I think the other thing to be really mindful of is just being really clear about how you give that feedback to and making about the behavior that you want to see differently, rather about kind of the person or an attribute of theirs. And that's something we spend a lot of time coaching founders and leaders on, is always framing the feedback as what is the specific action or behavior that you want to see differently, right?

Daniel Stillman 30:01

Yeah.

Rei Wang 30:02

Using the example of SBIO is a great way to kind of frame that feedback. Talking through the situation, the behavior, the impact and the opportunity, and how that person can either get a new way or approach to shifting that behavior is fundamentally sort of the crux of the conversation.

Daniel Stillman 30:26

Yeah, I'm a big fan of that framework, and it seems like there's a term I use, it's called the FQ, which is the festering quotient. And it seems like you guys really have a super intentionality around keeping the FQ really low because you have that shared vocabulary around feedback and a real bridge of communication that it's expected and that it's being offered within a good framework and within the right spirit, which is, like, super duper awesome. Thank you for that. Anita, do you have anything to add about conflict and how to keep the FQ low?

Anita 31:07

Yeah, I will add that. By the way, can you hear my baby?

Daniel Stillman 31:13

No, I can't. And you know what? Babies and dogs are always welcome on the podcast. It's totally fine.

Anita 31:19

She just started crying. Okay. She's good. The thing I would add is a lot of times feedback is a one sided conversation where you drop something that you want someone to change, and then that's it. You expect them to go off and make that change. And that's why, as we talk about Sbio is the opportunity, and that's where we invite people to take more of a coaching stance, where they get curious and have a conversation. And that part of it is, I think, the most important, because then you can get on the same page and really feel like you're co creating a solution versus someone telling you to do something different, which makes people become defensive. And so that's one thing that is really important in terms of conflict. And the other thing is with the festering quotient. I think about a lot of the founders that I've coached where we've had an open and honest conversation, and I turn to them and I say, can you say that to your co founder? And they're like, what should I do? And it's like, no, have that conversation with them. And at first, people are tense. They don't know how people are going to react. But it's so important to, again, not dwell on it and spiral on it, because then you're making up your own stories versus bringing it to the table so you both can come to the same page and just have an open dialogue.

Daniel Stillman 32:52

Yeah. This is such an important thing about the stories that we tell ourselves about what's going on and the stories, how we interpret what some of these actions is. And I think what's interesting about the SBio framework is it's really about owning your own. This is what I saw. This is what I saw. The SBI is still like, I saw this, this, and this. This is my experience. And just owning that, I think, is so powerful, versus saying, like, you did this, you did this. You did this. And it's a stance, it's a small shift, but I think it's a really important one.

Rei Wang 33:31

Yeah.

Anita 33:31

It's removing the judgment from what you're saying and making it really objective.

Daniel Stillman 33:36

Yeah. So our time has gone quickly and delightfully. There's so many questions I could ask you all, but I will just ask you, what have I not asked you that is important for us to talk about? What is something important? What's a layer deeper that we haven't touched on, or a parting thought that just seems important to reflect on around this question of powerful, effective co founder relationships based on your experience. And Anita, if you want to go first, if you've got something, Rei, we can just popcorn whenever you feel like you got something.

Anita 34:18

What I would add is the key skill of empathetic listening and how important it is in conversation, especially with your co founders. As leaders, we've been socialized to constantly problem solve and pattern match and listening to respond. And when we're in that mode, we get lost in what's really going on. And so one of the things that I hope everyone walks away with is how can we listen to really understand someone's situation? How can we get curious and just be with that person? And if everyone takes that stance and really hones in on empathetic listening and then asking open and honest questions, I really think the world would be better off. And the way that we talk about open and honest questions, it's a question that you don't have a preferred answer. You're not trying to lead someone into a particular answer, and it's not a yes or no question. And so I would say those two things, if co founders can really build those skills with one another, then your relationship will really go to the next level.

Daniel Stillman 35:33

Yeah. What is your favorite question? That is sort of an open, honest, empathetic. I mean, obviously they're the best ones come up in the moment, right? And they're new questions, but I'm willing to bet you've got one in your back pocket that is a favorite for you.

Anita 35:47

Yeah. So I love to teach people what I call outcome shift. And it's a set of two questions that really helps people move away from the problem that they're spinning on and go more into the solution. It's very simple. The first question is, what would you like? And then the second question is, what will having that do for you? And it's really powerful because, Daniel, when's the last time someone asked you, what would you like?

Daniel Stillman 36:19

Usually at a restaurant, it's not very frequent exactly.

Anita 36:24

But then what will having that do for you? Really gets to the core of what someone is seeking. And so you keep asking, what will having that do for you? You repeat back what they've said and then you keep drilling down and you can uncover so much with just those two questions. I was talking to someone who wanted to ask them, what would you like? They wanted to get their MBA and we went through that exercise and in the end we found out that no, they really just wanted to make their parents proud. And so what are other ways that they could do that? And it just opened know a deeper level conversation.

Daniel Stillman 37:04

Rei, does, does Anita ask you that question often? And if do you get tired of it?

Rei Wang 37:14

We do an exercise where we'll actually just keep on repeating that question. What will having that do for you? Over and over again until we get to the source of truth. And it is pretty powerful what it can reveal.

Daniel Stillman 37:26

You guys are such nerds. I love it.

Rei Wang 37:30

We are total nerds.

Daniel Stillman 37:31

You're literally drinking your own champagne. That's beautiful. Do you ask it? Show me. We have almost no time left, but you say, what would having that do for you? And you say something and then she says something. You're just sort of like going back and forth on this and she says.

Rei Wang 37:50

What will having that do for you? And will ask me sometimes five times in a row, right until I get to the root of what I really want.

Daniel Stillman 37:59

Yeah, I love that. That actually is in the room. That's super awesome. Rei, I would ask you the same question in the moments we have left. Like, what haven't I asked you what's important for you to say? And maybe your own favorite question would be amazing.

Rei Wang 38:19

Yeah, I'd say for anyone who's listening that is thinking about starting a company with another person, I think great relationships and great co founder relationships really take time these days. I feel like it's popular to do co founder dating or co founder Kind of speed Networking. I've seen a lot of those events pop up and while I think it's a great way to meet people, you're not going to go from a speed networking event or a dating event to kind of being co founders and great co founders overnight, right? No, I think just like all great relationships and all collaborations, it takes time. You have to form Storm Norm before you can perform. And Anita and I now have had the benefit of working together for eight years. But even in the early days of transitioning from first round to the know, we were very intentional about spending time together to form. So we went on a retreat together in the early days to talk about what the grand's vision was going to be and also to make sure that we could spend four days together in a cabin and really be able to work together well. Right? We did a couple of initial sort of pilots where we facilitated off sites together for other companies just to see what it would be like to work together in a new way or in a new environment. And I think all of those initial projects and initiatives really helped us get a feel for what it would be like to work together in this new capacity. So that's my advice for anyone who's listening, is give yourself that time, put yourself in these unique environments with your co founder to see what that relationship is going to be like and continue building it over years. Because ultimately, I really do believe that co founder relationships are what kind of make or break a company. We've seen it time and time again with the founders that we work with. So you really have to be intentional about investing that time into.

Daniel Stillman 40:27

Is. Oh, sorry, Nina, you wanted to say plus one that.

Anita 40:30

Yeah, like, plus one that. And I would just underline, make sure you can have fun. Know, that's another thing that Rei and I do intentionally, where sometimes we will get together and intentionally not talk about work and make sure that we can have fun as two individuals, two humans. After that event in New York, Daniel, you'll find that's fun. Rei and I were so hungry, we went and got hot pot. Just talked for hours and it was glorious. And so I think that's really important in the co founder relationship, too.

Daniel Stillman 41:06

That is your. Did you know this is a favorite place of one of yours from your New York days, BRei?

Rei Wang 41:14

No, we just both had forgotten to eat at the event. You know how it is, Daniel. We were starving at the end and was just trying to find any place that was open at a Tuesday.

Daniel Stillman 41:26

I'm always looking for recommendations, but if it was just serendipity, then I know the feeling of being below the line with food is halt. As they say, hungry is the first on the checklist. We are at time grand people. Thank you so much for making time to have this conversation. Where should people go to learn more about all things grand if they want to join the grand world?

Rei Wang 42:01

Yeah, definitely check out our website, www.theGrand.World. And if you want access, we've actually built a feedback tool based on SBiO that anyone can use for free to practice having feedback conversations. So you can sign up for that by going to home the grand world.

Daniel Stillman 42:18

And I will put links to that in the show notes. Thank you so much for the conversation. I'm so sorry that the Internet sometimes is not our side, but I appreciate you two being super patient with the technology. You two are awesome.

Anita 42:35

Thank you so much for hosting.

Rei Wang 42:36

Thank you so much, Daniel.

Anita 42:38

Thanks for your thoughtful questions.

Daniel Stillman 42:40

Thank you. Thank you very much.