Prototyping Partnerships — The Conversation Factory

How do you make a friend?

How do you become lovers with someone?

How do you become business partners?

In RomComs, there’s a “meet-cute”...the hilarious and unlikely way two people in this topsy-turvy mixed-up world collide and fall madly, rapidly in love.

In the real world, taking time and gradually testing, trying and yes, prototyping a relationship is ideal. In love, we call it dating. There’s no good word for “friend-dating”, especially when you’re doing it with someone of the same sex.

And with founding a company…where does the conversation start?

In this conversation, I sit down with Jane Portman and Benedikt Deicke, co-founders of Userlist, on how they connected through shared communities, and learned how each other really worked through real-world, previous projects.

They also share their insights on setting the stage both for a long-term vision for building a company AND for a possible exit from a partnership through thoughtful conversations.

Userlist is a tool for sending behavior-based messages to SaaS customers and recently completed a pre-seed round with 21 angel inventors.

Benedikt is a software engineer from Germany who loves to plan, build, and grow web applications. He co-hosts the Slow And Steady Podcast and organizes the Femto Conference, a tiny conference for self-funded tech companies. Jane is a leading UI/UX consultant specializing in web application design, and has been the host and founder of the UI Breakfast podcast since 2014 (she kindly invited me to join her show in early 2022).

Enjoy my conversation with these two delightful co-founders as much as I did.

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Links, Quotes, Notes, and Resources

UI Breakfast

Userlist

benediktdeicke.com

Better Done than Perfect podcast

Jane's Story: Turning Thirty: Story of My Life

Culture, Values, Operating Principles & More

Inspire, Not Instruct: How We Do User Onboarding at Userlist

Minute 8

Daniel Stillman:

So at that moment, how did you decide to go all-in? All three of you said, "Yeah, we're going to make this happen." How did you decide to structure your relationship at that beginning stage of this new idea?

Benedikt Deicke:

If I remember correctly, Jane had that proposal and connected all three of us, and I think the first thing we did was have a conversation about what we want from this. And we did an exercise about... I don't remember the name of it, but it was something from Google Ventures about company culture and tone of voice and stuff like that just to get a feeling of we're aligned in terms of values and goals. And that was pretty helpful to get a rough understanding of each of our expectations and where we might differ. And I remember that one of the exercises was, let's plan for, "Where do you see yourself in the next five years, 10 years, 15 years?" And I think one of the learnings from that was that we were pretty well aligned in terms of expectations and goals. And that made it easier in terms of starting just together, because we knew we were on the same path and not heading in different directions with the expectations and where we wanted to take this.

Minute 15

Benedikt Deicke:

I guess one thing that was valuable in entire process of doing that, I think it was the Google design sprint exercise that we did. And having the founder agreement and just talking through all those things aligned expectations from the get-go. And I feel like that's already a good way to minimize disagreement down the road, because I feel like a lot of the fights that founders might have between each other is because they're not on the same page and have slightly different ideas about the future and slightly different expectations. And by just making sure that we're on the same page, for the most part at least, already helps with reducing the conflict.

Minute 17

Jane Portman:

To be entirely honest, all these measures and being aligned and the vesting schedule and everything, this is all great. But the biggest success factor is that we had worked together prior to that. I would not jump into co-founder relationship these days without having worked with the person. And that's the only idea how you can judge their communication, their work ethics, and a lot of other things you can never understand if you don't get involved. We were lucky that, I had not worked with Claire for example, Claire had an amazing track record as a marketer, so I just took the dive. But the relationship that now keeps working is between me and Benedikt, and we had tested it prior to starting. So I consider that the key success factor. Everything else, surely great, allows you to part ways, but at the core of it is maybe bringing somebody for money first, or somehow before trying to bring them on into the shares or something like that.

Minute 28

Daniel Stillman:

What advice would you give to someone else who feels like their co-founder isn't putting in as much as they should? It's a difficult conversation to have.

Benedikt Deicke:

But it's one you should have, right?

Jane Portman:

Even though it must be had. It must be had. This communication principle, I think I saw it in Crucial Conversations. I forgot the author of the book. It's pretty famous. Basically, you have problems with your boss, your spouse knows about it, your colleagues know about it, except for your boss. So if you feel like something is unfair, that is the conversation to have. And these fundamentals of being rewarded for your time, either with salary or with shares and keeping it fair for everybody, this is fundamental so that everybody can perform so that they feel everything is honest. Without that, without the feeling of fairness, without the fundamental of being fair, this is broken. You're feeling like you're trapped or something like that. This is not going to move forward. So it's fundamental.

Minute 34

Jane Portman:

I'd like to touch on how we do planning. And we borrowed this principle from Shape Up by Basecamp. And it says, basically, "Don't worry about your backlog as much as people do." So previously, before adopting this, we would religiously every month meet and reprioritize 60 items in our backlog. And this is just such a ridiculous activity, because in software, everything changes all the time, because you learn, you keep learning the circumstances, change, opportunities arise, things that seemed important, don't seem as important because you've learned something that is crucial to your customers in higher degree. And we just plan out the next, I don't know, let's say two, three big features. Even one, two, I would say. One, two, three, something like that.

That is true for product and for marketing, so we usually have a marketing theme direction for the next, let's say quarter or something. And there is also the things in the product that Benedikt is working on with the technical team. So there is high level roadmap, but there's definitely nothing set in stone, and we are fine with it. And that relates to that level of fluidity that we discussed. We're comfortable with that. There might be some people who are not, but works for us.

More about Jane and Benedikt

About Benedikt

Hi! I’m Benedikt Deicke, a software engineer from Germany. I love to plan, build, and grow web applications. These days, I build my own products, organize a conference, contribute to open source, and co-host a podcast.

About Jane

Jane Portman is a UI/UX consultant specializing in web application design, founder of UI Breakfast and Userlist. At Userlist, Jane's goal is to provide flawless UX and help users be awesome at their customer messaging. Jane has also been running UI Breakfast Podcast since 2014.

Full Transcript

Daniel Stillman:

Oh, my God. We're live. Welcome to the Conversation Factory you two. Thanks for making this happen.

Benedikt Deicke:

Yay.

Daniel Stillman:

Big yay indeed.

Benedikt Deicke:

Thanks for having us.

Daniel Stillman:

Yeah. It only took a couple of tries on calendar.

Jane Portman:

Thank you, Daniel. Thank you, Daniel.

Benedikt Deicke:

True.

Daniel Stillman:

So the basic question, how did you two find each other in this crazy mixed up world? I've been thinking about this idea of serendipity and how extraordinary it is that anything happens at all. So how did you two... Maybe you can introduce yourself a little bit, but I want to put it in the context of, how did you two find each other and decide to do this project, to start this thing that you're doing? That's the big question.

Jane Portman:

So we run Userlist, a software that helps SaaS companies send email automation, send email messages to their customers and leads. That is a fairly complex software product, and I'm really excited that Benedikt, the brilliant technical brain on the other side of the microphone has been on this journey. And we have known each other for 10 years, I think, roughly.

Benedikt Deicke:

Not quite, but it's getting close.

Jane Portman:

We're getting there.

Benedikt Deicke:

Yeah, it's getting close.

Daniel Stillman:

So you've known each other for 10 years, but Benedikt, when did you start thinking about what userlist became?

Benedikt Deicke:

So after meeting each other, I think we met online in a community or so, and I think a couple years after we've met at a conference and basically have been in touch after that on Twitter and social media in general. And at some point Jane was thinking about starting her first software product and was looking for a developer to work on that with her. And it wasn't userlist at the time, but in the end, I joined that project and she hired me as a developer. And in that process, we discovered that there was a tool missing in our stack that was basically userlist. So that's where the original idea came from.

Benedikt Deicke:

But it wasn't for another couple of months where we, I think, figured out that the other project we were working on wasn't quite the right thing or didn't quite work out that I think Jane, you got an inquisition offer, right? That got you thinking about moving on to the next thing. And then I think in the end, it didn't really pan out with the acquisition plan. But suddenly, there was free time and a new idea and Jane was like, "Hey, let's maybe tackle this other thing we discovered along the ride," and that's what we did.

Jane Portman:

Yes. Yes. And there were three of us in the beginning, and the second try, I thought we've got all the bases covered and we are going to skyrocket to 5K MRI in five months or so. And yeah, a lot of things went differently, but ultimately, it was a good start. And maybe today we can talk a bit more about how we can help others find their good co-founders and what's the best way to set it up, right? Because, as you can see, one of us left and we're still friends, which is a rare thing, if you think about it.

Daniel Stillman:

Very much so. I'm wondering though, I want to go back because Benedikt, this is really interesting. I think Jane, maybe you had mentioned this, that you had known each other for a while. So there was a community that you two had connected on and exchanged some messages. You sort of knew who each other were, and then you met IRL.

Jane Portman:

We met a few times at MicroConfs in Europe in person. We hang out in the same, I don't know, Slack community and definitely had a lot of friends in common. And also, my first experimental book in 2013, I think, there was a guy who bought it and I thought, "Hmm, what an interesting guy. Weird name, long hair." And then I saw his picture popping up again and again, and then we met in Prague, I think, eventually. And yeah, we met a few times.

Daniel Stillman:

Well, you wrote your book around 2014, you met-

Jane Portman:

13. 13.

Daniel Stillman:

2013.

Jane Portman:

It's nine years. Yeah.

Daniel Stillman:

Yeah. Wow. And then you had a couple of interactions in real life, and it was just friendly, collegial, I guess you might say.

Benedikt Deicke:

Yeah.

Jane Portman:

There's great spirit in the startup community, around this ecosystem of raw balling startup for the rest of us, MicroConf and now Tiny Seed, a lot of fellow founders, I was a consultant serving them design, Benedikt was a consultant serving them-

Benedikt Deicke:

Development.

Jane Portman:

... engineering. And also, Benedikt had his own product back then. Was this nice vibe going on. But yeah, when I was looking for a developer, another friend of mine said, "Well, if Benedikt suggests his help, go take it. He's the best you can find." So I did.

Daniel Stillman:

That's amazing.

Jane Portman:

And I really took him up on the deal. I really took him up on the deal, because, well, I'm a non-technical founder and I didn't have massive budget back then in 2017, I think, in the fall. Or actually 16. That was the fall of 16, I think.

Benedikt Deicke:

Right. Yeah. Yeah.

Daniel Stillman:

And so you had this moment where you were like, "Okay, this is..." So Benedikt, you were saying that Jane, you had got an offer for that company that wound up not working out, but it got you thinking, "We should start thinking about the next thing," and that seed of that next thing was inside of what you had been building together. Yeah, we can't see video, but she's waving her head, so I didn't get it quite right.

Jane Portman:

We just discovered a gap in the tools that can be used for running a SaaS. Back then, there was, at least in my head, I could only see Intercom that could send both email and in-app notifications based on user behavior. Also, this problem of... When Benedikt helped me launch the product, was a launch day and I realized we don't have a dashboard and building one takes money and time, and how can I see who my customers are? Because I had expected analytics to solve this problem, but analytics don't really solve this problem of CRM-ing your customers to a sense.

Daniel Stillman:

Do you remember the conversation the two of you had about where the gap was and the seed for this next idea?

Jane Portman:

Well, I wrote emails. I wrote emails to Benedikt and to Claire. I thought we will have all the bases covered. Claire was a marketer, Benedikt's an engineer, I can do design and the rest, and we were a killer team. And I can't believe they both said yes, so that was the process.

Daniel Stillman:

So at that moment, how did you decide to go all in? All three of you said, "Yeah, we're going to make this happen." How did you decide to structure your relationship at that beginning stage of this new idea?

Benedikt Deicke:

Jane Portman:

Because all three of us had experience consulting other for other SaaS companies, and we've seen different flavors of those SaaS companies, and it could be that, for example, me and Benedikt could go and expect a more calm, bootstrap business, and Claire would see, "Oh, let's raise five million in the next year," and just put fuel there. And we were more or less aligned with the sustainable bootstrap journey where we could take our time to build a sustainable product without burning a lot of money right away. So for example, one of those things.

Daniel Stillman:

Yeah. Yeah. So who facilitated that conversation or who brought the plan for that dialogue? Was that you Jane or was that Claire or?

Jane Portman:

I had an original three pager doc, and then Claire started piling on more questions, and then Claire brought this format for the workshop that we did together, so it was a collaborative effort. There were other resources we used, for example, for the concept of vesting, for the concept of not splitting the shares absolutely equally. We had this point system that we bought somewhere, where you first have equal amount of points and then you score a couple of points to the person who starts, a couple of points to the person who has the audience, a couple of points to the person who can do this and that, and we ended up with a slightly different number so that it's not a 50:50 split, which sounds to many founders, it's an obvious choice, "Yeah, let's do 50:50," but maybe it's not the best choice. Who knows? Well, we do.

Daniel Stillman:

How long did you spend on this conversation? You had your three-page doc, Claire brought in some of these visioning conversations from Google and the points conversation, how much time did you put aside just to facilitate that dialogue?

Jane Portman:

A few weeks. And we also put together a co-founder agreement. That was also part of this dialogue, that we fleshed out a few more details about specific scenarios that could go right or wrong. We even invited... What's the word for it, Benedikt?

Benedikt Deicke:

What was the name?

Jane Portman:

Third-party friend.

Benedikt Deicke:

A mediator basically.

Jane Portman:

And independent friend who could judge... Yes, mediator. A third-party friend who we all know who could help us resolve disputes if we could totally not do it on our own. Well, thankfully, we didn't do that.

Daniel Stillman:

Yeah. Well, just to be clear, this is a fourth-party friend, because there was three of you.

Jane Portman:

Yeah. Well, we all knew the person that we named the mediator. That was the idea, so that-

Daniel Stillman:

Oh, I see. So all three of you knew the mediator, and this was the person who was going to come in if you hit a bump, or were they-

Jane Portman:

It was the plan.

Daniel Stillman:

... also judging your partnership agreement as well?

Jane Portman:

Not much at all. Just for the bump role.

Daniel Stillman:

Yeah. Did you hit some bumps? Did this person have to come in?

Jane Portman:

Not for this person. No.

Daniel Stillman:

That's very interesting.

Benedikt Deicke:

It was basically a safety measure. I guess we were worried that when there's conflict, it would be two against one, and getting into unfair situations, and we wanted another neutral party that was able to put things into perspective and maybe have a neutral outside perspective and be like, "Yeah, you can't do this because it's unfair to that other person," and stuff like that. So we were lucky that we had a mutual, well, not close friend, but acquaintance that we all knew and trusted with this. And they were nice enough to agree. And in the end, luckily, it never came to it, but it was good to have it set up just in case.

Daniel Stillman:

It's so interesting. I feel like in a way almost having that... Or maybe I should ask this as a question instead of a presumption. Do you think having that backstop helped you manage your disagreements or did you just not hit any rough patches in the time that you were together?

Jane Portman:

I think all three of us were not naive, rather mature. Not 19 years old when you just jump in, build something and then figure it out. We're bitter and we've seen different situations in life. It's a lot similar to marriage. And even after you've seen a few couples divorce, you realize that nothing is really forever, and many scenarios may arise. So we wanted to put guard rails in place for potential different scenarios that could arise, that of course we might see eye to eye at the moment, but what if something comes along we don't know about, then what happens?

Daniel Stillman:

Yeah. Sorry, Benedikt. Was there something-

Benedikt Deicke:

No.

Daniel Stillman:

... you wanted to add about that? I just love the idea that you put the guardrails there, and if they're good enough, you don't even need them ideally.

Jane Portman:

Like a prenup.

Daniel Stillman:

Like a prenup, yeah.

Benedikt Deicke:

Daniel Stillman:

Yes. Yeah. There's two things that I'm hearing here that are great principles for anybody. One is to spend significant time thinking about the near and longer-term vision, the 3, 5, 7, 15 year, and just align on, "Are we making a fast company or a slow company or something in the middle?" That's a really important decision to be straight on. And the other negotiation theory, there's this idea of interests, options and legitimacy. It's called the circle of value. It's, as we enter into this negotiation and we both have interests, we both feel like we have certain options and we both have our ideas of what legitimacy is. And I love that the three of you picked a person that you all agreed they would be, in a sense, an arbiter of what is legitimate and fair, so that it wouldn't be a two against one conversation. I think that's really amazing.

Jane Portman:

Daniel Stillman:

Yeah. I mean, I think it's an interesting question of... And this may be a weird way to describe this, but Benedikt, you and Jane now are co-founders, right? So there is a difference in relationship between when you Jane brought Benedikt on as a contractor for hire on an idea that was yours. Now this is an idea that belongs to both of you.

Jane Portman:

I think the consultant relationship, it has different dynamics. And it's good because Benedikt could see that I'm adequate when it comes to money, I can see that Benedict is adequate when it comes to money. If we had only worked on a, let's say, non-for-profit project, it was just fun, might have been different. Who knows? But I just knew that it was fine. I don't know. It just felt fine. Felt secure and nice. And he didn't trick me into big money, even though he could definitely charge the hell out of me for what he did.

Benedikt Deicke:

And I guess what also plays into this is that we had very compatible styles of working. I feel like this is also something that is easily overlooked, is that the amount of planning you need and the amount of stuff you maybe do ad hoc and a spontaneous work stuff, if it that part doesn't align, one of the parties, or maybe both parties might get frustrated really quick. Because you might think, "Ah, this other person always needs two weeks of planning things out and then being able to execute. I want to execute right now." And the other person maybe is like, "Ah, he's always switching focus and making a mess and there's no structure." So I feel like a lot of it is also about matching styles of working on stuff.

Jane Portman:

I'm so glad you brought that up. It's not just the working style, not just the planning, but also the quality standards of what you put out. Because we are both rather fluid in planning, but we are super nitpicky that we need to put out the quality product. It's got to be close to perfect. Of course, it's not possible to achieve complete perfection in real life, but both in engineering and in design, we will strive for the best. And some people like it messy. I couldn't work with somebody like that, I'm pretty sure.

Daniel Stillman:

Fair. Yeah, there are the people who believe that you should put it out when it's at 80%, because of the Pareto principle, but you're like, "No, I want that last 20% before it gets out the door." That's good.

Jane Portman:

Email automation. We're sending bulk email to somebody else's customers. Seriously, 80%?

Daniel Stillman:

No. Well, and I'm glad that you have that shared perspective. Have there been challenges that you've had to manage in your relationship?

Jane Portman:

There have been disagreements.

Benedikt Deicke:

Yeah, it's not always a smooth ride.

Jane Portman:

One co-founder quit. Yeah.

Daniel Stillman:

Well, let's talk about it. I'm curious how you've managed some of the bumps in the road that you've experienced with each other.

Jane Portman:

Benedikt, what do you think? How do you describe that?

Benedikt Deicke:

I was wondering what to talk about. I mean, we should probably touch on Claire leaving the company at some point, because that's probably the most significant one so far, because it made a lasting difference and changes everything-

Jane Portman:

Changes everything.

Benedikt Deicke:

... and changes the dynamic, so.

Daniel Stillman:

Yeah. I mean, it's very interesting because you guys did a lot of upfront work to check on alignment, and then it... Between the start and... When did Claire decide to step down? What was that arc?

Benedikt Deicke:

I think it was one year in-

Jane Portman:

Just one year in.

Benedikt Deicke:

... something like that.

Daniel Stillman:

Just one year in.

Benedikt Deicke:

I mean, we talked about all that planning and the goals and the future and expectations, and what I probably have to say about this is, yeah, we made a plan, and yes, we had visions, but none of this was true. We expect it to be-

Daniel Stillman:

So I hope everyone listened to this point in the podcast.

Jane Portman:

No, the plan was true. We were true to ourselves. It's just, the plan didn't work as expected, as it often happens.

Benedikt Deicke:

I mean, we still had the shared vision and stuff like that, but everything took a lot longer than we expected. So I think one year in, we didn't even have the product done in a way that people were actually using it, so we were not making any money. And all three of us have been doing this on the side, we had still our consulting gigs where we were making the money to pay rent and food and stuff like that. And that of course took away from working on the product and everything was a lot slower. And yeah, about a year in, Claire was like, "Yeah, I have two other businesses I'm running and they are making money and they're taking most of my time and focus, and unfortunately I can't spend more time on userlist, because what's the point? It doesn't make any money, and I'm short on time anyway, so I'll focus my efforts on those other two businesses."

Benedikt Deicke:

And while it was a bummer for us losing our marketing expert, there wasn't a big argument about it because it made sense. In a way, we were in similar positions, just that each of us only had one other side business and not three. So it was sad, but in the end, I mean, because we had those guardrails in place, it was clear what needs to happen to have a transition out of the company. And the way we set it up in our agreement back then was we had to allocate the shares of the company roughly a third each, and we had the vesting schedule, so we'd only gain ownership of our shares over, I think, 50 months, something like that. So every month, we would-

Jane Portman:

Yeah, 50 months.

Daniel Stillman:

Five, zero.

Benedikt Deicke:

Five, zero, yeah. Almost five years, not quite.

Jane Portman:

And we just finished that with Benedikt, by the way, we're fully invested now. Just a few months.

Benedikt Deicke:

Yeah, we're fully vested [crosstalk 00:24:46].

Daniel Stillman:

Congratulations. How does it feel like to finally own your own company?

Jane Portman:

Not much different.

Benedikt Deicke:

It doesn't change much. But the goal was you'd earn 2% of that block of shares per month that you keep working on it. So when Claire was like, "Yeah, I don't have the time to put effort into this anymore," we first reduced her vesting rate from 2% to 1% for a while. And eventually we decided, okay, it doesn't make a lot of sense to keep her on this, and we stopped it at some point. And that overall reduced her amount of shares to whatever she had earned by that date and kept things fair in a way, because now we definitely own larger shares than her because she stopped working on it after a year or so.

Jane Portman:

Technically, going back in time, we should have just stopped vesting altogether. But this was this half measure that we reduced her vesting in half. And it felt nice to do because she was advising, but going back in time, and even if you're a young startup, every month of vesting counts. So if the person is not putting in work, don't vest them shares just because you want to look nice or hope for something, because the company will be worth much more down the road, and every percent becomes a sufficient thing. We don't regret this. It was just for a while, and we're happy that we're friends with Claire, but making difference between being nice and rewarding shares for work, these are different buckets, don't mix that. Don't mix that with friends or-

Daniel Stillman:

This is a very hard thing to do. Last night, I was-

Jane Portman:

Am I phrasing this right, Benedikt? You're just grinning.

Daniel Stillman:

Since you were all at that time working part-time, how did you define what was the right amount to be working on the project? Was it value created or was it hours logged?

Benedikt Deicke:

I think we had an informal agreement that it was 50% of our time sort of, but we didn't track hours or something like that. It was basically, we'd see each other's progress and be fine with it, or when you had the impression that, "Hey, you're not putting in enough work," then we'd call each other out on that. But overall, it was never an issue for the most part. I don't remember having a big conversation about that at any point, so.

Jane Portman:

Up to this point, we don't track hours, because why we're in is for freedom. But there's also pretty serious peer pressure and motivation and accountability that comes from having a co-founder. And if you're not putting in the hours, you're the one who feels guilt and suffers after all.

Daniel Stillman:

What advice would you give to someone else who feels like their co-founder isn't putting in as much as they should? It's a difficult conversation to have.

Benedikt Deicke:

But it's one you should have, right?

Jane Portman:

Daniel Stillman:

Anything you wanted to add to that Benedikt?

Benedikt Deicke:

No, not much. I mean, it's an unpleasant conversation, but it's one you must have, because afterwards, things will feel better, because at least the opinions are on the table and you might fight about it, but maybe you agree. I mean, I remember we had some bumps like this a year or two ago, where I felt like Jane was a little bit distracted with other stuff, and we brought it up, and in the end, we agreed that yeah, maybe we have to restructure things a little bit. And in the end, it worked out and it was definitely better after having that conversation than the couple of weeks before it was like, "What's going on? We're not making enough progress on whatever task was on the to-do list back then." So might be uncomfortable at first-

Daniel Stillman:

Do you remember that conversation, Jane?

Jane Portman:

Hmm?

Daniel Stillman:

Do you remember that time?

Jane Portman:

Oh, sure. Yeah. It's not like everything is clouds, unicorns and roses and stuff. We just switched to full time maybe a year ago, it was a smooth transition. And we had some funding from Tiny Seed, which was good, but not enough to just hire full time, big time, but it already gave us some freedom. So there was this transition from, do everything yourself to get help and where and how and how this looks like. And at that point, I didn't have a clear picture of exactly how to efficiently delegate, let's say, the marketing department was the first we started like delegating out, and there was a series of experiments with hiring generalists, specialists. Not all the experiments were successful. And then there was this fundraising question because we did raise another angel round last year. So we were wondering, "Do you have good enough product market fit to support this fundraise? It doesn't make sense. How do we do this?" and other things, more discussions. But I'm happy we came out of the other side, happy and invigorated in a sense.

Daniel Stillman:

How often have you revisited that conversation you had at the very beginning that Claire helped co-facilitate, where you talked about your vision and your values?

Jane Portman:

Roughly speaking, once a year, we have a bigger planning goal. Maybe a couple times a year. Benedikt, what's your impression of that?

Benedikt Deicke:

Yeah. I feel like it probably wouldn't hurt if we just went back to that exercise from then and do the exact same thing again, because we haven't done that. But of course, at the beginning of every year or-

Jane Portman:

It's be fun to look at the responses. It would be fun to see the responses.

Benedikt Deicke:

Yeah. Right. Let's see how the vision maybe changes and the expectation changes. But overall, I mean, we're having conversations once per week about the short-term roadmap and what we are planning to do and things that are happening in the business and all of that. But I feel like, at least at the beginning of each year, we make a rough plan of like, what are the next big steps? Where do you want to go next and what needs to happen, and what are the problems? So in a way, we're doing it on a regular basis, but I guess it wouldn't hurt to have this deep workshop type of conversation where we try to realign on stuff. I think it wouldn't hurt doing it again.

Jane Portman:

Never hurts. I'd like to touch on how we do planning. And we borrowed this principle from Shape Up by Basecamp. And it says, basically, "Don't worry about your backlog as much as people do." So previously, before adopting this, we would religiously every month meet and reprioritize 60 items in our backlog. And this is just such a ridiculous activity, because in software, everything changes all the time, because you learn, you keep learning the circumstances, change, opportunities arise, things that seemed important, don't seem as important because you've learned something that is crucial to your customers in higher degree. And we just plan out the next, I don't know, let's say two, three big features. Even one, two, I would say. One, two, three, something like that.

Jane Portman:

Daniel Stillman:

Say a little bit more about that. What's important about letting go of being strict about the backlog.

Benedikt Deicke:

I feel like-

Jane Portman:

The thing is, it will never be implemented in the order you put it. What's the sense of ordering 50 items?

Daniel Stillman:

Pair-wise.

Jane Portman:

You can barely make the first five happen in time, and given the fluidity of everything, product, customer, market, anything.

Daniel Stillman:

Yeah. That's fair. Benedikt, what was on your mind?

Benedikt Deicke:

Yeah, basically that. The backlog, they're all good ideas. You look at each one of them, you're like, "Yes, yes, that's a good idea. And we have this one customer asking about it and it makes sense for everyone else." But you only have so much time and you have to pick something and stick for it for a while to make meaningful progress on it. And by the time you're done with it, you can pick one other thing maybe, maybe two, if you're lucky, and you still have 50 other things on the list that are still good ideas, but not necessarily the best thing to work on right now. And therefore, just keeping that list and working through that list. I mean, we did that in the early days, and I remember going through that list every couple of weeks and being like, "Yeah, yeah, we should probably do that at some point, but we just don't have the resources right now. So let's move to the next thing and look at that. And yeah, same thing."

Benedikt Deicke:

And at some point, you just keep looking at the things and being reminded of all the nice things that you potentially could be doing, but you are not because you're working on other stuff or more important stuff. It just becomes in a way, becomes a little bit frustrating because you're always feeling like your product falls short and your product is way from done and way from useful, even though that might not even be the case, because a lot of people are already using it.

Jane Portman:

I there's anything we had learned after these four years of userlist, and we had been consulting prior to that, but I had never realized that it's such a tale of limited resources. It's all about limited opportunities that you can pursue, exactly like Benedikt said. And when you're a consultant, it seems like, "Oh, why don't they do that? That's on the surface. Why don't they do that? Why don't they do this?" And it's so easy to give advice, but when you're inside of it and you only have this much development resource and you have this much time, you have to A, prioritize, and B, somehow live in peace with this. So understanding that you can surely have the vision, but it's not always up to that vision because of resources. And I ask people who are way up in the letter and it's the same for them. It's the same for our big integration partners. It's never that you can make everything happen, so you have to live with it.

Daniel Stillman:

So how do two people choose one thing to focus on as the whole company? What is that conversation like for the two of you? What's easy about that? What's challenging about making that choice? And what do you do instead of having that list of reminders of things you could do, what do you have instead?

Benedikt Deicke:

We still have a list, but it's not super detailed. It's more like gut feeling, broad ideas and not super fleshed out. And our planning process these days are usually... One thing I think we do really well is we have a lot of customer interactions, either in customer support or during demo calls with potential new customers, or just keeping in touch with our audience. And that usually informs the next steps pretty well, because the things you keep hearing over and over again are probably the things we want to tackle next. And that makes the conversation relatively easy. And so far, I feel most of the times, we're on the same page about stuff. We have the same gut feeling that should probably go into this direction and ensure maybe we fight about like, should we do this particular part of it first or that other part of it first? But it's so far working out relatively well. I don't think we had big disagreements on product direction so far.

Jane Portman:

And moreover, there's the marketing department, my kingdom, sort of speaking, and there is the product department, which as a UX designer, I have a word to say, but it's Benedikt's ultimate hand touching the code. And if he doesn't write it, it's not going to happen, so he's the product owner for sure, and I'm totally at peace with that. I'm happy. Basically, we do call the shots to some extent in each of the departments. However, we do consult before pursuing some major directions. That's the key, but on daily basis, it's us ruling two different departments in fact. The marketing machine for this is insane. We did not pick an easy battle. It's always a lot of education and everything we have to do. Education, brand building, everything for such an essential tool, it's very important.

Daniel Stillman:

Yeah. Because not everybody has the mental model of why they need it.

Jane Portman:

And how they should use it once they install it. It's like everybody has an understanding they need email automation, but using it well to the full power, nobody's born an email automator, and we're trying to make up for that.

Daniel Stillman:

That is true. It is not a native capacity for anybody.

Jane Portman:

You can be born a designer, you can be born an engineer, you're hardly ever an email automator really. Let's face it.

Daniel Stillman:

So listen, the two of you, we only have a little bit of more time left and it's been a lovely conversation. Is there anything we have not talked about that we should talk about when it comes to sketching the arc of your co-founder conversation together?

Jane Portman:

There is a great deal of infrastructure that surrounds a software business that it's not talked about much, but it includes co-founder agreements, the legal paperwork, the bank account, postal addresses, cell phone numbers, having all the passwords in place, I don't know, support desk, shared emails. There's so much to do that should be done properly so that if anything happens, first, you pass the bus test, or if somebody decides to leave or I don't know, gives birth to a baby or something-

Daniel Stillman:

The what test? The bus test? I missed that.

Jane Portman:

Yeah. The bus test is like, can your business still survive when one of the founders gets hit by bus? And it's especially true for a solo founder business. I'm not kidding.

Daniel Stillman:

Wow.

Jane Portman:

What are you going to do? And it can happen.

Daniel Stillman:

Okay. And Benedict, what haven't we talked about that's on your mind? I've learned about the bus test. This is a new one.

Benedikt Deicke:

Yeah. I mean, this is a good point. What else? I mean, one thing that we hinted at earlier is the plan and reality don't always overlap. And I think looking back at the last four years, or almost five years, four and a half, something like that, things move a lot slower than you want them to and that you expect. And what I definitely underestimated is the toll that puts on you on a mental level, just the ongoing slog of putting in hours and hours and hours of work and the company just growing slowly, super slowly. And that was hard over the last year or so. It was hard for a while. I feel like there's this valley of despair where the product is used, but it's not making enough money to fully sustain the business, but it's not bad enough to easily call it off as a failure when it's in the state of barely working.

Jane Portman:

Definitely not bad.

Benedikt Deicke:

When it's barely working, it's insane. The stress that puts on you is crazy, and I underestimated that for sure.

Jane Portman:

The startups survive by not dying.

Benedikt Deicke:

Sort of, yeah.

Jane Portman:

You just need to keep going, and it's a slog. It's much more routine and boring than it seems. It seems like, "Yeah, exciting idea. Snap, we're going to make it happen," but-

Daniel Stillman:

Yeah. How do the two of you take care of yourselves given that stress and that slog? What do you do for yourselves to keep sane?

Jane Portman:

Human maintenance stuff; sleep well, eat well, exercise as much as you can. It's the simplest and the hardest thing to do.

Benedikt Deicke:

I mean, I think what we do well, maybe better than others, I don't know, we're very strict about boundaries. For example, we usually don't work on weekends unless a thing is on fire. The weekends are off, evenings are off. We don't have expectations to be on call 24/7 for whatever comes up. And I think that helps in keeping your mental side in check by just having breaks and taking vacation and taking time off and being fine with that, and not expecting the other person to be there and answering emails and answering messages all the time. I think that helps with keeping us sane.

Jane Portman:

There's another angle we do fairly well compared to people I know, is hanging out with other founders, peer support. And all of us have our own mastermind groups when we hang out with other founders just to talk life and to talk business every two weeks let's say or something. And we have great advisors and we have over 20 angel investors who, if we have hit a wall, I just write up a giant notion doc describing the problem and we send it to a couple of most relevant people and we try to brainstorm that. So it's never like we're in a box or alone, there's always some sort of input from peers or mentors.

Daniel Stillman:

One thing I'm taking away from this conversation is you met inside a community, and it seems like community is also helping you stay afloat and stay sane.

Jane Portman:

It's not always the same community, but yeah, it's different levels of community. Many levels of it has evolved. Definitely. But you can't just go alone.

Benedikt Deicke:

Yeah. I mean, if you want to take away one thing from all of this, I guess just building a network is the best thing you can do, in whatever we talked about, either finding a co-founder, finding advisors, finding investors, employees-

Jane Portman:

Employees too.

Benedikt Deicke:

... just get out there and make friends with people, and that will come a long way. It will take a while to build that network and to nurture those relationships, but in the end, a lot of the good things that happen to userlist, we can probably.... Yeah, no, I'm not finding the right word, but at the root, if you follow it back long enough, you find this was based on this one relationship that we had in our network or whatever, that friend and that recommendation or whatever. So I feel like that's one of the key skills to develop, is making friends.

Daniel Stillman:

Yeah. I think it's really beautiful. I mean, I can't imagine that either of you thought when you first logged on to that community, that this is what it would've led to.

Benedikt Deicke:

Definitely not.

Jane Portman:

Yeah.

Daniel Stillman:

Well, I think that's a really great place to close out. I'm really grateful for the time, for the both of you being so reflective and open and honest about your experiences and your insights. I really appreciate it.

Jane Portman:

This was fun to share, going down the memory lane.

Daniel Stillman:

Yeah. There's a lot to be gathered from memory lane. It's awesome.

Benedikt Deicke:

Yeah. We enjoyed that conversation.

Jane Portman:

Thanks so much for having us.

Daniel Stillman:

All right. We'll call scene. Yeah. Well, I really appreciate it guys. Thank you so much.

Jane Portman:

Thanks for having us, Daniel.