In this conversation, I dive into the nuances of co-founder relationships with Clarity.so co-founders Richie Bonilla, CEO and Eni Jaupi, CTO.
Clarity.so is a y-combinator funded startup that has built a groundbreaking DAO contribution platform. DAO stands for Decentralized, Autonomous Organization, which you should totally google if you want to know more.
While Clarity isn’t a DAO, you can see how the radical transparency that is at the heart and spirit of the cryptocurrency movement is also at the core of Richie and Eni’s relationship. I mean, it’s also the name of the company!
Like a few of the other conscious co-founder interviews I’ve been doing, these two co-founders prototyped their working relationship before jumping into their company together, which helped them build a foundation of trust and respect.
They also talked a lot. Like A LOT before even starting the company. Starting with a few times a week, they gradually transitioned to talking for at least an hour, daily, for a year.
What this conversation re-established for me was that it’s important to have agenda-ed conversations, and it’s also very important to have stream-of-consciousness, unagendaed conversations, too. Generally speaking, we’re great at structure, and less good at making space for wondering and wandering. For more on the power of wondering and wandering, make sure to check out my interview with Natalie Nixon.
Be sure to check out my conversation with Jane Portman and Benedikt Deicke, co-founders of Userlist, on how they connected through shared communities and learned how each other really worked through real-world, previous projects.
You may also enjoy my interview with Carolyn Gregoire and Scott Barry Kaufman, the co-authors of the 2015 bestseller, Wired to Create, where we unpack how they managed their working relationship.
And if you really want to dive deep into the idea of being a conscious co-founder, make sure to check out my conversation with my friend Doug Erwin, the Senior Vice President of Entrepreneurial Development at EDAWN, the Economic Development Authority of Western Nevada.
Links, Quotes, Notes, and Resources
Minute 6
Richie Bonilla:
So basically in our first year working together, we talked a few times a week and we would have very in depth conversations about the work that we were doing. Once we started working on Clarity together, which was sort of a very organic and gradual transition. We talked, we would meet every day to talk. And we would talk about the things that we were doing, which would take maybe 15, 20 minutes.
And then we would spend another 40 minutes every day. So it would be like a total hour every day, talking about what this could become and what this could be. And so we basically spoke every day for an hour for the first year that we worked together. And I think that we're still reaping the benefits of getting on the same page in that way. Whereas, like a lot of my friends who don't work remote thought that was crazy. They're like you sit on the call for an hour a day. What do you even talk about? And I think that was probably one of the best things we ever did. I think we're still, like I said, reaping the benefits of that alignment.
Minute 25
Eni Jaupi:
This may be just, I don't know how to exactly call it, but we always have said this out loud: that our best interest is this company and knowing that full well, that just irons out whatever small conversation that we were having, that did not match, or our opinions did not match completely. So those are mostly just knowing that the other person knows that your intentions are fully aligned with his and at the same time, just putting aside your pride, that sometimes you just need to say, "Okay, let's just do it. And that we can talk about it later again." Try to not say I told you so, if something goes, as you imagine, as the person that said no, or the person that had the objections predicted or said, so just small things like that are part of the growing experience.
Minute 30
Richie Bonilla:
Even though we agree right now, let's still take the time to run through these other scenarios, so that we're make sure that we agree, rather than just taking a surface level agreement and being like, yes. And then running through it later." I look at it as de-risking the project, because if we get into details later, it's actually harder for us to fix this. So yes, we agree at this level, but let's go two or three levels deeper on this and make sure we agree on those levels too. And the way that we end up doing that is by saying, "Well, what happens if you know this or that?,Or the other thing?" And playing through those scenarios.
Minute 32
Richie Bonilla:
And I think that this is representative of how we approach our whole relationship, where in the beginning of starting to work together, we're like, "Oh, we're taking this more seriously." Getting aligned on what kinds of things you're trying to do with your life. Like, "Hey, if this is an opportunity here to make this something really big, are you here on a 10 year mission with me? Or are you looking for a passive income side hustle, SaaS product?" Those are fundamentally different visions. And it's really difficult if one person is like, "I'm sort of happy with like a 10K a month SaaS business. Why are we going through all this trouble to change the world?"
That's a really tough thing to reconcile later. Also, things like, "Hey, if it was right for the company, would you move to the United States? Would you move to New York City and come over here? Is that a deal breaker for you? Or is that something you're open to?" Because, we don't know what the future's going to hold. And that might be the right thing for the business.
So looking at all of those sort of irreconcilable positions really early on and having those conversations really early on, I think is something that we definitely did. And I think that people avoid it, because they're scared that like, "Oh, this person doesn't want to ever move to the US. And is that something that I can live with? And if not, crap, I just lost this opportunity." But I think it's the alternative. It's way harder to have that conversation later, if you're not in agreement.
Minute 36
Richie Bonilla:
I think that the way I see it is like, always talk about the thing that's relevant right now first, right up until the point where we feel like we have a handle on it. So getting through those open questions and then depending on where we're at. So sometimes something's really urgent. It's like, let's get this conversation done. Let's make these decisions. And let's get off the phone as soon as possible. Other times, you finish that conversation. You're like, "I've got this thing in my head, this idea that I can't kick and I want to share it with you. And let's explore that for a minute." And maybe we won't build that feature or encounter that problem for a few months. But by doing this, by the time we do get there, we've already talked about it 2, 3, 4 times, and we've already built up a shared mental model of like what that's going to be
More about Richie and Eni
Richie Bonilla is Co-founder & CEO of Clarity. His background is in product design & software development. He entered web3 by contributing to an early NFT gaming community in 2018. He worked as a remote freelancer for 10 years across various industries. This perspective informs his work at Clarity where he and Eni are building tools for DAO contributors, who experience many of the same problems faced by web2 freelancers.
Eni Jaupi is Co-founder & CTO of Clarity. His background is in software engineering, working as a remote freelancer for 9 years. His first introduction to crypto was in early 2017 while building side projects.
Full Transcript
Daniel Stillman:
I will officially welcome you to the Conversation Factory. Richie, Eni, welcome aboard. Thanks for making time for this. I really appreciate it.
Richie Bonilla:
Thanks for having us.
Eni Jaupi:
Thank you for having us.
Daniel Stillman:
So I think let's start with the big picture, which might be giving folks a sense of who you all are and what you're working on.
Richie Bonilla:
So my name is Richie. My background is in design and product, also technical. And so just like sort of a multidisciplinary founder. I'll let Eni introduce himself, but what we're working on is called Clarity. We believe that... We were freelancers in Web2 and we think that freelancing is great, because you have a lot of independence, freedom. And if you do a good job, you can make some pretty good money, but the downside is that it's very lonely and it's also very risky for a lot of folks, because they don't know where that next project is coming from.
Richie Bonilla:
And we see Web3 and DAO as a way to solve those last two pieces, because we think that community and networks help with that. And so we're building Clarity, which helps these DAOs to become more organized and more legible and more accessible, so that more people can engage with them. And so Clarity takes the form of a collaborative workspace that integrates tokens very seamlessly into the experience.
Richie Bonilla:
It includes both documents and project coordination tools, natively, and some other more social features that help people coordinate together. And so we think this is really important for people to be able to build reputation and be able to go off road and be an independent worker, and be what we call on Web3, a contributor. That's the new version of freelancers in our opinion. And so, that's what we're working on.
Daniel Stillman:
That's cool. Eni, do you want to add yourself?
Eni Jaupi:
Yeah. Just to give a brief background on myself. I'm Eni, I'm from Albania, so pretty far away from Richie. I'm primarily a software engineer. I say primarily, because when you work the remote or in general, in a project by project, you have to wear many hats. But I like to call myself a software engineer, first. I've worked remotely and as a freelancer practically, my whole career.
Eni Jaupi:
I wouldn't be able to say was what are the best things and the worst things, because this is practically all I know. So it would be a bit hard to make a difference, is what I can say though, is what Richie said about it being full of great opportunities, but at the same time being a bit lonely, just because you're not having so many casual conversations with somebody that you meet with the screen, a few times a day or a few times a week. So about Clarity, I think Richie is the voice that I also like to hear, when we talk about Clarity itself. I just give all my opinions away. And that Richie actually say them back to me, because that just feels so much better and sounds so much better than me actually saying it.
Daniel Stillman:
So Eni, are you saying that you use Richie as a sounding board, like you express your ideas and then Richie helps reframe them back to you? They make more sense.
Eni Jaupi:
Yes. That's almost always been the case even in our previous project, because in our previous project I was in the team. So I was a software engineer, but I had no prior relationship to Richie. So our first meeting was practically in a sprint kickoff. So of course, there was that tension of a new developer coming in and the project manager on the other side, having expectations for you, but what we found worked and I think that has always been the case was, what we're talking about a bit earlier, which is, I like to give my opinion. I have a lot of opinions about product in general, but being of an engineering mind is really hard to explain in a human in "Way". And that'-
Daniel Stillman:
Your so called human ways of talking.
Eni Jaupi:
Our so called human way of talking. And Richie has an outstanding ability to really understand what I'm trying to say without me needing to break out of that role, because you either have to do one or the other, if you really want to be good at one. So even when I change hats, practically, my way of speaking actually changes quite a lot, because when I'm trying to say that, "Okay, these things that we are trying to build is really cool, is really important, but technically these are the challenges." It's really hard to do that, if you want to also be able to convey that... Okay. The thing that we are trying to do is going to be done, is just how it's going to be done, that needs some talking through.
Daniel Stillman:
Richie, anything you wanted to add to that? How does that spark for you?
Richie Bonilla:
Yeah. I think that's the unique thing about us was that, I also similarly have been a freelancer for eight years until... Clarity is like our first real job for both of us. And I think that early on in our relationship, especially for the first year that we were working on Clarity together, but I would say... Let me restart that. So basically in our first year working together, we talked a few times a week and we would have very in depth conversations about the work that we were doing. Once we started working on Clarity together, which was sort of a very organic and gradual transition. We talked, we would meet every day to talk. And we would talk about the things that we were doing, which would take maybe 15, 20 minutes.
Richie Bonilla:
And then we would spend another 40 minutes every day. So it would be like a total hour every day, talking about what this could become and what this could be. And so we basically spoke every day for an hour for the first year that we worked together. And I think that we're still reaping the benefits of getting on the same page in that way. Whereas, like a lot of my friends who don't work remote thought that was crazy. They're like you sit on the call for an hour a day. What do you even talk about? And I think that was probably one of the best things we ever did. I think we're still, like I said, reaping the benefits of that alignment.
Eni Jaupi:
I think Richie is talking about the median, because those conversation could go into five or six hours. For me, it was 6:00 in the morning and I was starting to not sound really good, because I was falling asleep. So that's, where the conversation would naturally end. So I think that has always been a cool part. And when we do it now, it sounds... Because it's not that this was, oh, like 10 years ago. But it sounds nostalgic, because when we still do that and we go into deep conversations for hours and hours [inaudible 00:08:02], and this is through the screen, so through a microphone, it just feels organic.
Daniel Stillman:
I think this is an amazing insight in terms of the way you're creating intimacy from far away. And as you said, Richie, before we started recording, the two of you met in person once, and that's all after you had already been working together for some time on this project, on this company, is that right? So you'd built up a lot of connection points and a lot of alignment and a lot of intimacy, intellectual intimacy, all of it from far away.
Richie Bonilla:
Yeah. I think that was because we let conversations go stream of consciousness. So we would have our agendaed conversation and be very disciplined about that. But then we would just like, let things... We still do this. We just allow for stream of consciousness to take over in a conversation. And sometimes we go over time. Sometimes we talk about stuff that probably is not relevant for six months, but I think a lot of the time we, what we're doing is... I think most of the time it's actually very productive in that, it allows us to keep a shared mental model of the entire business. And so we've always done that. And we did build up a lot of... I think I like that word, intellectual intimacy, before meeting in person, because of that.
Daniel Stillman:
One thing that I've heard from a couple of the other co-founders that I've been connecting with is, I find it interesting, just like any other relationship there's a million, there's so many fish in the sea, there's all these people out in the world. There's a lot of makers and people with ideas and people who want to create a company. Of all the... What's that line from Casablanca? Of all the bars in all the world, you walked into a place... How did you, of all the serendipity, what serendipity created, the two of you crossing paths, and then taking that next step into getting closer? What was right before, "Yeah. Let's work on this together?"
Richie Bonilla:
Yeah. So on my end it was bidding for a job on Upwork that I won. And so I was working out. We worked on this project, there was these casting directors in New Orleans. They had this amazing system for casting directors to find extras, because extras casting is very different from main character casting. There's a lot of like bulk casting. It has to be a lot about their appearance and just like a lot 50 different attributes that you can match people on. And so they had this system that had organically grown. It was way more than what they had ever anticipated doing. They needed someone to come in with a product lens and really rethink it. And so they hired me for four months before bringing Eni in. And so I had done a lot of user research and iteration, and then he was brought in to sort of lead the development team and help to start building it. And so that was on my end, what it looked like.
Daniel Stillman:
And so Eni, this is what you're talking about. You're plopped into the middle of this group that's already been together, been working for a while.
Eni Jaupi:
So on the other side, for me, it was actually a lot less intentional. So it started as a conversation with somebody that was part of the team and they were just saying, "Okay, you should jump in. I think this is a really cool app that you could work on." And so I just got there and practically, okay, these are the things that we need. This is the stack. Sounded cool. The app looked cool. So it was a lot more just a nonchalant decision of, "Okay, this is a cool project. Let me just try it out." The guys were already working, I believe at that point. So they had quite a few things built, but when I jumped in the thing that actually connected us more so than anything else was caring about the project. When you're in freelancing, you have projects one after the other.
Eni Jaupi:
So it's kind of hard to care on a deep level, that the thing that you are working on really needs to be something big. And from my side, that has always been the goal. So to be a big part of something big. And so the tendency to care, I think that's just what did draw us, as sometimes we would be the only two people talking in a call and maybe that would be kind of annoying, but that was also organic. It wasn't something as a single case or a single decision that we worked on specifically, and that built our relationship up.
Eni Jaupi:
It was just get on a call and just things flowed from there. We understood each other really well, so that also helped quite a bit. I was also not really shy to say my opinions. So I think that was also something that from Richie's side actually, that stood out as, okay, this guy knows what he is talking about. And at the same time, some of those ideas, if not all, they clicked. So that, probably has something to do with it.
Daniel Stillman:
So in the story now, I'm hearing you're starting to click, you're thrown to the middle of this experience together. How did things accelerate to these long, weekly conversations? What was in the middle between connecting and feeling some similarities, some understanding to, yeah, we're going to work on this thing together and really accelerating into that?
Richie Bonilla:
Yeah. So I think that one of the first things that clicked for me was that Eni would show up to these calls and he would ask me really detailed questions about what we were going, what problems we were solving, and then he wouldn't take any notes. And I was just sort of like, "What's this guy's deal? He asked me these questions, he doesn't take any notes." And he'd also, didn't read off of a list of questions. He would just sit there and ask me. And I was like, "He's not listening. Why are we doing this?" But then every week it would like, that would work and everything we talked about would be implemented or whatever, and then we'd move on to new stuff. And he never dropped anything. And I was like, there's something up with this guy.
Richie Bonilla:
There's a trick or he's just like raw intelligence is really high. He just retains information. That's not how my brain works. And so that was like the first thing that clicked. I was like, okay, this is interesting, a different relationship than I've had before. But I'd say that one of the things that was happening was that I had... Because I had been working remotely for so long and I started my career working remotely. I developed a system for running remote teams, using existing tools in a specific way. And I was prototyping that system on the team and Eni really took to sort of... I think he realized what I was doing, or at least that's my impression of it. And started suggesting improvements to that system and the bigger thing that we were building.
Richie Bonilla:
And so over time, that's the system that became Clarity. That was the thing that we started to then build product around. Especially once we started to contribute to these Web3 communities in like 2019. And so that's how Clarity progressed. And so he was sort of working on Clarity before it had a name, just by helping me to sculpt the system to run the team that we were running together. And so I think that's where we really started to mesh, was like we were having conversations outside of the work that we were doing for the client. We were really working on something else, an art project together. It was like a Meta project. And that took a larger and larger percentage of our mind share over time.
Daniel Stillman:
So Eni, you were aware of the structure and you were giving feedback, not just on the content, but the process, the structure.
Eni Jaupi:
At first, I was not aware specifically that it was a structure. It just seemed to be something that worked. I couldn't give a name to it, because I hadn't talked to Richie specifically. There was something that he was doing, but at some point you start to pick the patterns of, okay, we are doing this, this and this. And every time that we did that, it worked every time that we didn't do it, it worked less well than it could. So that just became a lot more obvious. And of course adding input, of course, I believe the input that I give back then, Richie, must have absolutely crossed his mind. It's just that he was being polite with accepting feedback. But at some point Richie said that he was going to step away and he mentioned that he was going to build a "Ticketing system."
Eni Jaupi:
That's what he called it to practically make it sound as, "Yeah, I'm just going to do this thing probably to not jinx it," but that's when it actually clicked that, oh, okay, he's going to take this thing and make a product out of it. So that's where I messaged him and the message was just, "If you need help as a passion project, I'd be glad to help you." So it didn't start as, "Okay. Let's do this thing together." Started more so, "Oh, I see what you're doing. I see where your head's at, and if you just need help, especially on the technical side, I'd be happy to help with it."
Daniel Stillman:
That's such an interesting... That's a moment where you're like, wait, there's something here and you sent that invitation. Richie, do you remember getting that message from Eni of like, "Yeah. Yeah. Tell me what I can do. Tell me how I can help."
Richie Bonilla:
Yeah. I was sort of conflicted, because I knew that I had heard and believed from my own observation that the best co-founders are people who you worked with on something prior, whether you worked at a company together and were on the same team, or whatnot, or had a previous startup together. And so being a freelancer, I didn't even have a lot of "Colleagues" that I had worked on teams together. And so I really wanted to work with Eni, and I thought that if there was somebody in my life who I could work with on something, it would be Eni, but I also was like, I don't feel comfortable like poaching somebody off of my client.
Richie Bonilla:
I don't know where this thing is going to go. I didn't want to create any bad Juju. And so I was sort of like, "All right, guys, I'm leaving." I broke it to the team. I was like, "Hey guys, I'm leaving. I'm scaling down my freelancing to focus more on this side project." And then when Eni reached out and was like, "No, no, what are you doing? Tell me more." And then was like, "I want to work on that with you." I was like, "This is some universe stuff. I can't just ignore this."
Richie Bonilla:
And so I made it very clear to the client, who's a friend of mine still. And I said, "This is what's happening. Put it in writing, make sure everyone knew what was going on. He's working out with me on some stuff that might increase in the future, who knows." And that was my clean conscience progression through the situation, because I was like, can't really give that up. This is someone who I'm working with, who I've never worked so smoothly with somebody, who's clearly this talented. And so you can't just like pass that up.
Daniel Stillman:
You answered the call, that message. And I think that's really cool that you tried to be really clean about it. And something we were talking about before we got started was, and I appreciate you mentioning universal received best practices. And I think you definitely nailed on one, which is you can't start from zero. You're already building on some knowledge about each other and you're building that intimacy on a foundation. And Richie, you'd mentioned that you'd had some previous experiences that were maybe not so awesome on the co-founder side. Maybe now's a good time to talk about some of the anti patterns that you've experienced in the past.
Richie Bonilla:
Sure. Yeah. We had at my first company, which the funny thing is I've freelanced through that entire company, because it never quite got off the ground in a meaningful way from a revenue standpoint. And so I had to always be a freelancer to make that work as well. So my point is just that working on that company, we dropped out of college to start that company. And I started it with some guys who I had just met and there were four of us. And so there was all these red flags, like in retrospect. Just met, never done this before, four co-founders. You're just compounding the number of things that are red flags for co-founder relationships not working out.
Richie Bonilla:
And that came to bite us. So in the end it ends up being like me and one of the co-founders who's a CEO and we were working on it together for the longest period after the other two folks had left, one didn't want to leave school. So we had to tell him, "Sorry, but that's not the level of commitment that we're looking for." So that, was like a tough situation. And then the other one wanted to go to grad school. And so then he decided to go back to school or he didn't drop out in the first place, he graduated and then went to grad school. And so we were sort of left the two of us. And then unfortunately I had to decide to leave, because just the direction of the company, we were focusing more on like the operations of hospitality properties, rather than like the software part, which is what I was really interested in, where I saw my career going.
Richie Bonilla:
And he was really good at that part. And so that was another tough thing was like, then I had to be the one who left, which was also its own struggle. And there's all the writing on the wall, like in retrospect of like I said, those various criteria that we didn't hit, but then... So with this one I had a mental checklist of things I wanted to see in a co-founder relationship. And I was prepared to basically be a solo founder, if I didn't find that, but that definitely wasn't the preferred situation.
Daniel Stillman:
Yeah. So a lot of that was in your mind, I'm guessing as you were thinking about this next, next idea. Eni, had you had past experiences with the downside of co-founding?
Eni Jaupi:
Not really, I don't want to jinx it, but this is my first co-founder experience.
Daniel Stillman:
You just have to say jinx and then hit something, hit some wood or something.
Eni Jaupi:
Oh, okay. Got it. So on my side, I'm trying to be the exception of not having prior roadmap of failure points. So I hope to never know what those failure points are. I can't say anymore than that, at least. I know my struggles. I know what I could have done better, but I'm not sure if I would've changed that, as opposed to something else, because I think the journey to be where we are now also needed some in between points, that in retrospect are not ideal, but of course it's part of the growth. So I wouldn't say that something is specific to either being successful or not. I think the experience is also growing and into actually becoming two people that can talk about more than the specific task in hand, about things that span multiple years, or multiple decades as we sometimes do.
Daniel Stillman:
Eni, when you think about the time you've been working on this together, you talked about failure points and learning. Do you feel like there have been friction points that you've been able to work through? Well, clearly effectively creatively. And if so, I'd be curious to explore how you manage those. You haven't had an explosion yet. We're still here. You guys seem like you're on good terms, but there's always bumps on the road.
Eni Jaupi:
Of course. I would say that at least nothing has sticked out as, okay. We absolutely need to figure this out before we are able to continue working with each other. This may be just, I don't know how to exactly call it, but we always have said this out loud that our best interest is this company and knowing that full well, that just irons out whatever small conversation that we were having, that did not match, or our opinions did not match completely. So those are mostly just knowing that the other person knows that your intentions are fully aligned with his and at the same time, just putting aside your pride, that sometimes you just need to say, "Okay, let's just do it. And that we can talk about it later again." Try to not say I told you so, if something goes, as you imagine, as the person that said no, or the person that had the objections predicted or said, so just small things like that are part of the growing experience.
Eni Jaupi:
I think those are just things that happen. I think any relationship has those and especially two people that until very recently could not meet each other. Like, "Yeah, okay, let's do it." But if you say that too many times, there are too many things left untold or unsaid. And you don't have conversations, maybe sometimes the time, maybe sometimes just as a... "Okay, we need to do this. You cool with it?" "Yeah. I'm cool with it." Those are just things that compound, so trying to get that out of the way as soon as possible. Or as soon as you see that something is penting up. I think that's part of it. Although full disclosure, we have been so much on the same wavelength, that when we had the discussions about product, one of us would just be the devil's advocate.
Eni Jaupi:
So we would be on the same page and the other person would take the stance of, "Okay, I'm going to take the stance of, let's do this other thing." We are on the same page. We want to do that. But the other person just came up with reasons to knock off the thing that we were both agreeing on. So it sometimes goes to the point that we agree on so many things where we are in the same wave length that we need to take stances of, "Okay, let's do this from the other side. So let's try to knock it down." And one person tries to defend the current position the other person becomes a devil's advocate saying, "Yeah, but there's also this one, or this case, or this case." So I can say about the red herrings, or big things actually.
Daniel Stillman:
And are you setting up that devil's advocacy conversation intentionally, like I'm going to... Or Richie is making a face like yeah, maybe no. Or it just happens organically.
Eni Jaupi:
It happens organically. So it depends on the thing. If it's a technical discussion, or usually the "Disagreement" of opinions are when Richie's designer brain is versus my engineering brain. Those are the ones that we don't need to consciously go into the devil's advocate. Or in the other side, we just try to come up with reasons why the thing that we were both thinking about does not work. So we consciously go into, "Okay, what if this is the case? Does it work or not?"
Daniel Stillman:
Yeah. Richie, what's this been like hearing Eni process these thoughts? I'm curious. What's the all sparking in you?
Richie Bonilla:
Yeah. The funny thing is, I think we do, do that, but we've never... I don't think we've ever used the word devil's advocate in describing it. We never actually said like, "Okay, I'm going to take the devil's advocate position here." We usually say something like, "Well, the counter argument to that is-"
Daniel Stillman:
Yeah.
Richie Bonilla:
And it's sort of like, I think of it as we're programming a system and we need to make sure... We're QA testing the ideas, if you will... Here's an edge case where that doesn't work. And let's present this scenario. Let's run this scenario and see how it plays out. And so I think it is doing exactly what Eni described, but not in a way that I think people think when they hear the term devil's advocate, because that can often just be the person who... I think devil's advocate has a really bad recognition.
Daniel Stillman:
I'm not a fan of that. It's like, "Why would you advocate for the devil? That's a terrible idea."
Richie Bonilla:
Yeah. There's a lot of like, "Oh, you're just masking your actual opinion behind this contrarian thing in order to like say something that is going to upset other people." I think that often is like a misuse of devil's advocate. And so like I said, I don't think we've ever used that, just that terminology. But we do it in the sense of like, "Let's run through these other... Even though we agree right now, let's still take the time to run through these other scenarios, so that we're make sure that we agree, rather than just taking a surface level agreement and being like, yes. And then running through it later." I look at it as de-risking the project, because if we get into details later, it's actually harder for us to fix this. So yes, we agree at this level, but let's go two or three levels deeper on this and make sure we agree on those levels too. And the way that we end up doing that is by saying, "Well, what happens if you know this or that?,Or the other thing?" And playing through those scenarios.
Daniel Stillman:
This is like explicating the positions without taking them.
Eni Jaupi:
Yes. So just to clarify that I've at least [inaudible 00:31:31] we use it as a non bad meaning thing. Surprising. So I just meant doing the... Just take taking the opposite stance of the thing that we're discussing. I didn't notice until right now that I should be more careful with the-
Daniel Stillman:
No, no, there's a-
Eni Jaupi:
Explaining that.
Richie Bonilla:
Yeah. This also happens too. We just have like a cultural... "Oh yeah. So that's, how we use the word here, or like that's how-"
Daniel Stillman:
But I love this idea of QA testing an idea. So what I'm taking away is, and it sounds like you're on the same page of this is, QA testing an idea, looking at the whole problem space, looking many layers down and not necessarily taking a position, but exploring a positions. And I feel like in terms of working through challenges as an important question, this is absolutely best practice. And it's great to see the two of you just willing to dance around in the problem space before you take hold of a solution and run with it.
Richie Bonilla:
Yeah. I think like to your earlier question of what are things we've creatively done about like to do this? And I think that this is representative of how we approach our whole relationship, where in the beginning of starting to work together, we're like, "Oh, we're taking this more seriously." Getting aligned on what kinds of things you're trying to do with your life. Like, "Hey, if there's an opportunity here to make this something really big, are you here on a 10 year mission with me? Or are you looking for a passive income side hustle, SaaS product?" Those are fundamentally different visions. And it's really difficult if one person is like, "I'm sort of happy with like a 10K a month SaaS business. Why are we going through all this trouble to change the world?"
Richie Bonilla:
That's a really tough thing to reconcile later. Also, things like, "Hey, if it was right for the company, would you move to the United States? Would you move to New York City and come over here? Is that a deal breaker for you? Or is that something you're open to?" Because, we don't know what the future's going to hold. And that might be the right thing for the business.
Richie Bonilla:
So looking at all of those sort of irreconcilable positions really early on and having those conversations really early on, I think is something that we definitely did. And I think that people avoid it, because they're scared that like, "Oh, this person doesn't want to ever move to the US. And is that something that I can live with? And if not, crap, I just lost this opportunity." But I think it's the alternative. It's way harder to have that conversation later, if you're not in agreement.
Daniel Stillman:
Eni, how do you feel like you manage the balance? Because, you all are still talking very frequently. Is it still an hour a day, at least, until, or at least until Eni falls asleep? How are you balancing the regularity, but also the talking about now, and also that longer term, because it seems like in every conversation you're circling around all of those levels.
Eni Jaupi:
That's a hard one, because it just boils down to, "Okay. We need to get back to a now level," or if we feel that this conversation is proving to be helpful, then we continue with it. But me and Richie say always that in what we do in startups, you have to know which fires to let burn and just feel the heat and deal with it. I think that's the same mindset as with the conversation. So if you feel that, "Okay, this is something that we can talk about later, we can postpone it." And this is usually something that comes naturally, if you have the shared context of everything going on. As you kind of feel it, "Okay, this conversation is drifting a bit too much for now. We don't really need to have it." So it's about deciding what is that point that, "Okay. We have gotten maximum value from it. No need to go further than that."
Daniel Stillman:
Yeah. Richie, is there something you wanted to yes and from that?
Richie Bonilla:
Yeah. I think that the way I see it is like, always talk about the thing that's relevant right now first, right up until the point where we feel like we have a handle on it. So getting through those open questions and then depending on where we're at. So sometimes something's really urgent. It's like, let's get this conversation done. Let's make these decisions. And let's get off the phone as soon as possible. Other times, you finish that conversation. You're like, "I've got this thing in my head, this idea that I can't kick and I want to share it with you. And let's explore that for a minute." And maybe we won't build that feature or encounter that problem for a few months. But by doing this, by the time we do get there, we've already talked about it 2, 3, 4 times, and we've already built up a shared mental model of like what that's going to be.
Richie Bonilla:
And so what ends up happening is that we have a really tight grasp of the details of the work that we're doing right now. And we also have a really robust mental model of all of the work we're going to be doing for the next three months. And then obviously there's the longer term stuff that we're talking about. "Okay. That's not going to be relevant for five years. Let's just dream a bit. That's a 10 year thing. That's a 100 year thing."
Richie Bonilla:
We have those conversations, but they're obviously a lot less frequent, but these loop, these concentric circles, if you will, evolve by allowing the conversation to go beyond just what is relevant at this moment. And it's the stuff you would talk about over lunch, or dinner, or drinks. Because we don't have that, I think that allowing a conversation to go a bit long is the way that it goes and not fighting it. So not say, "Oh, we should get off right now." If we both got energy for the conversation, let's harness that energy right now. And let's harness that enthusiasm right now, because we can't schedule it in. You can't schedule, "I'm going to have energy for this topic next week." Yeah. You can't do that.
Daniel Stillman:
And yet you can organize your schedule to allow for that space, which I don't think everybody listening to this has a calendar that necessarily allows them to say like, "Well, let's push things off and let's keep going with this." How do you two create this space to make that possible, to make those kinds of continuous conversations possible?
Richie Bonilla:
I would say so we have an international team as... Oh, you know that, but we have a really international team, because I think we have nine people right now. We have three in Asia, three in the US and three in Europe. And so out of necessity, we sort of need to be very disciplined about how we meet and when and for how long. And I think that what we... I know that what we do is we create a meeting time where we meet every day, every weekday we meet at the same time, some of those meetings are scheduled to go long. Some of them are really short, like 30 minutes, but the product team meets every day. We have it all hands every week for everyone who's contributing actively to Clarity.
Richie Bonilla:
And then we have one on ones with each other, like throughout the week. So every week we have one meeting with everyone in the company, we have five meetings, or four meetings with... No, actually five, because there's one right after the all hands. So five meetings with the product team and then one meeting with a one-on-one with everybody. And so throughout all of those conversations, you maintain a mental model of the entire thing. But because that happens at the same time every day, the rest of the day is wide open.
Richie Bonilla:
And so you can actually play with that time. Most of the time it's deep work time, but if we've got something that's running long, let's break off the people we need from this meeting, let everybody else go. And let's just figure this out for as long as it requires. And I think that the whole company basically rests on Eni's ability to have a Eastern schedule instead of an Albanian schedule. Because if he wasn't a night owl, I don't know how this would work.
Daniel Stillman:
What was it like meeting up in person? Where did you meet in person? Was it just the two of you, or was it getting the whole team together?
Richie Bonilla:
It was really strange, brutally strange. We met in Portugal in Lisbon and the first hour was incredibly weird. And I think like the only way I can understand why this was the case is, I think that intellectually, we knew that this was our close friend and co-founder and partner, but our brains didn't recognize that person was that person. [inaudible 00:40:58]. So it had this feeling of, I know that you are you, but I feel like you're a stranger.
Daniel Stillman:
Yeah.
Richie Bonilla:
And that was this really weird thing. And I've met a lot of people, internet friends online, but... I'm sorry, in real life, but I've never had that experience. I think it's just because we had such a robust relationship. And then all of a sudden, after an hour, we went and got dinner with a group of friends and it was still odd. But then after dinner, something clicked and we were a hundred percent normal. It was really strange. And then we were just talking, it was a 100% comfortable, a 100% normal, but that first 45 minutes to an hour was really weird in a way that I still can't get my head around.
Daniel Stillman:
Yeah. What was that like for you, Eni? I can see you're smiling, it's like [inaudible 00:41:51]-
Eni Jaupi:
I have no idea how to explain it, really. So the closest thing is what Richie said in which, "I know you, but I don't know why this feels weird." It was one of those cases that we looked at each other and starts smiling. Okay, what the heck is going on?
Eni Jaupi:
I don't feel like this is the normal way that this should actually work. And so that was... I don't know. I can get that out of my head. I don't know how I would react if we were exactly in the same position. Probably the same. But as Richie said, after an hour, it was as we had talked like that all the time. So it was exactly that. So a switch and I remember exactly where we were, in which we were walking down through some stairs, just clicked and as if that was a norm.
Daniel Stillman:
Wow. I don't think our biology was set up for handling this, so I think you... And I've had this experience myself, where I'm like, "Wow, you're so much taller than I thought you'd be." Because, here we are in this rectangle, we're all pretty much the same size. So it's really interesting to hear about your breaking through that.
Eni Jaupi:
I think the three dimensions actually has something to do with that. So you actually see that this person has a back of his head that you have never seen, like yes, something is wrong here.
Daniel Stillman:
"Wait, Richie's sideburns are so different than I thought they'd be. I could never really make them out." So this is so interesting. I'm really glad you shared this. And I think this is something that's going to be happening more and more, as we live in this fully distributed world and connect with people and do projects remotely. And Richie, you and I have Michael from Huddle and in common.
Daniel Stillman:
They creating teams like this remotely is just the norm. And so more and more people are going to be having the experience that you, Eni, and Richie are talking about, like, "I know you, but I don't know you and I didn't know what you smelled like. That's so weird." And then you just get used to somebody's presence. It's very different. So our time together is growing short. And I want to respect your time, because Richie, you're on a work-cation, which means you at least have a couple of hours or sun left in Mexico and I'd like you to enjoy that. What haven't I asked you when it comes to creating, building, sustaining a powerful, conscious co-founder relationship? What haven't we explored that's important to get on the board?
Eni Jaupi:
I would say a sense of humor.
Daniel Stillman:
Yeah.
Eni Jaupi:
In startup world, you have to be able to take things that are going on and in startup world, everything is going at the same time. So there's definitely something going on at any given point. So having this point that you can look at the other person and say, "Huh, that was kind of tough, wasn't it?" And not be a 100% serious, a 100% of the time. That helps me personally. So that, has been something that I've found to work at least for me.
Daniel Stillman:
Yeah. Totally.
Richie Bonilla:
Yeah. I have a couple of answers to this. I think that the first one is, especially when you're remote, there's not a lot of ways to read body language. So you have to be very clear. An example is yesterday, I opened a conversation with the team that I hadn't set up the conversation properly. And so there was a miscommunication of what my intention was behind the feedback that I was giving. And after the conversation Eni got on the phone with me, he was like, "Hey, I just really didn't agree with you on that." And I thought it was a pretty uncontroversial point and we talked about it, and turned out that just my lack of setup for the conversation made him actually misunderstand what I was trying to get across.
Richie Bonilla:
And so then today I was able to take ownership with the team and be like, "Hey, I realize that was a sloppy conversation, here is what I meant, if we want to talk about it more, we could talk about it now." But getting that direct feedback of like, "Hey, I really didn't agree with you." And then being like, "Why? Let's hash that out." That was the key to then being able to take ownership and correct it with the team. And I wouldn't say it was a big deal, but you stack a bunch of these tiny little things on top of each other and they become a problem later. So that was one of them. And then I would say another thing is, when disagreeing on something and actually being like, "Okay, we've explored this entire topic. We still don't agree on how to proceed. Let's frame it."
Richie Bonilla:
We frame it as like a bet. So you say, "Okay, what are we really doing here?" What we're really doing is we're taking a X $1,000 bet. Here are the parameters. Here's the budget for that bet. And in eight weeks we will know if it plays out and then we can decide how to proceed. So let's take a chunk off of the direction. Let's place that bet. Let's define the parameters for success. And then we'll go from there. And this way, it's not my idea, your idea. It's just like, "Hey, we're going to de-risk this we're frame it that way. We're going to evaluate it later and decide to double down or abandon course." And then the third thing I want to mention is a compliment to both of those, which is, I think that there's this responsibility in a co-founder relationship to not say, "I told you so," like Eni said before.
Richie Bonilla:
But that comes with the paired responsibility is to take ownership proactively over decisions that you made, that didn't go well and to say it before, so no one feels like they have to say, I told you so. So I will err on the side of saying, "Hey, I know I said this last week, that didn't go like I thought it would. I wanted to just take ownership over that. Here's what I think happened. Here's where I think we could do better next time."
Richie Bonilla:
But that was something where I totally miscalculated and I will err on the side of taking more responsibility than it's probably necessary for my mistakes, because at least it clears the air and the team doesn't think like, "Oh, this guy, keeps making mistakes," because you have to make mistakes in order to make progress. If you're doing it right, then most of the ideas you try don't work. If they all work, then you're not trying hard enough, or you're not being creative, or you're not being risky enough, or you're not being ambitious enough. And so you have to create the space for mistakes and for wrong decisions. But also that comes with the responsibility of taking ownership over those decisions and making sure that everyone knows that you know, that didn't go like you said it would.
Daniel Stillman:
Thinking in bets is so powerful and the ability to disagree, but still create forward movement on getting more information is a really, really powerful skill. And so I'm really glad you highlighted that. Also, I want to just acknowledge that we're just about at time and I'm grateful for the time. If people want to learn more about you all and what you're creating, what's the best place to send them?
Richie Bonilla:
Sure. So we have our website for Clarity at www.clarity.so. We have a blog there where we are posting more and more frequently, and we'll continue to do that. If you want the most high speed, high bandwidth version, it would be our Twitter @Clarityteams. Yeah, that's that. And I'm also Richie Bonilla at... I'm sorry @RichieBonilla on Twitter. Eni, is famously not on Twitter, so unfortunately.
Daniel Stillman:
Good for you, man.
Richie Bonilla:
It's the only way to do it. You're stuck with me.
Daniel Stillman:
Are you on Truth Social with [inaudible 00:50:21]? That's a terrible joke. I apologize. And I feel like... We're literally out of time, but if somebody who's listened to this and is like, but I don't run a DAO and looking at, when I looked at what you all were building from the outside, it looked like anybody who's building something collaboratively on the internet could benefit from that. Is that true? Or what kind of teams can benefit from what you all are creating?
Richie Bonilla:
So I would say that it is true that collaborative work can be done on Clarity for most kinds of teams or organizations. I think that we specialize in a type of coordination that is done by people who are not in a hierarchy. And I don't mean that there's no hierarchy. I just mean that they are sort of independent actors who are choosing to work together in a way that is not traditional from like a management perspective. And I think that's different, because we're freelancers. We were freelancers. We've always been that way. We are coming from a sense of not making people feel like second class citizens in the tool by being an independent worker. And that's how we've designed it from the ground up. And I think that there's a lot of that affects the user experience a lot.
Richie Bonilla:
When I think about project management tools in Web2, I think about tools built for project managers, and a project manager's job is to get the most out of their human resources. And that is one way of building an organization. It is not the vibe that I ever resonated with. And so we don't really think that we are building project management software, we're building project coordination software, because it's people who are each choosing to work together on a shared goal from a more equal view, rather than trying to optimize these people's capacity.
Richie Bonilla:
And so that's really the type of coordination that we specialize in. And I think that plays through the user experience, but yes, it is true that you could use it for any kind of team, except, there would be a ton of features for token integrations and crypto native functionalities and sign in with Ethereum, and these other pieces that would probably be totally irrelevant to you. Like bounty payout workflows and stuff like that. So those just wouldn't be that relevant, but if that's the style of coordination that you participate in, regardless of your goals. Yeah, sure. That's relevant. It's just not the type of organization that we typically focus on. We put all of our innovation energy into DAOs and other kinds of DAO like organizations.
Daniel Stillman:
That's really helpful. And I feel like what you're talking about is what a lot of folks talk about as the future of work, more teams that are more networked and horizontal. And so I feel like more and more teams will be more and more appropriate for the things that you're creating.
Richie Bonilla:
Yeah. And we feel that very strongly, because we have always felt this was the most fun, meaningful, interesting way of working. And we've chosen to do that year, after year, after year. And we're just looking to eliminate the downsides, so that more people can engage with that kind of work and not experience the risk, or the loneliness, or other factors that stop you from engaging as an independent worker.
Daniel Stillman:
That is awesome. Thank you so much for really, really putting a fine point on that. I think that'll be super helpful to have it in your voice, so that people understand this stuff. Because, I know it's not in everybody's wheelhouse. Web3 is an edge for a lot of folks out there. I want to respect your time. I really appreciate you two sharing and being so reflective. And I feel like I can safely call scene for the time that we've had together.
Richie Bonilla:
Thank you so much for having us. I'm so grateful for the opportunity to speak about the co-founder relationship and things, because I don't feel like that's a topic that we have a really get asked about. But it's something that's so important to us and that we've treated with a lot of intention and it's been really fun to have a chance to actually speak on that and be asked questions about it. So thank you.
Daniel Stillman:
Yeah. It's my pleasure.
Eni Jaupi:
Thank you, man. Thank you. And also thank you for bringing up a point during our discussions that I hadn't thought about previously, which is, we had talked about me moving to the US, if the company needed it. We haven't talked about Richie moving to Albania, if the company needed it. I thin we have our next conversation setup.
Daniel Stillman:
I hear the food in Albania is pretty good. I'm just saying.
Eni Jaupi:
Oh, it's amazing. I can tell you that.
Daniel Stillman:
You guys may not know this, but in New York City if you ever come, the most popular street for Italian food in the Bronx, Arthur Avenue is all those Italian restaurants are run by Albanians now, Eni. People, all these tourists come... Yeah. You know. Richie knows what I'm talking about.
Richie Bonilla:
Yeah. I used to live over there and I was telling Eni the same thing. I'm like, you won't believe the Albanian food here. You're going to love it.
Daniel Stillman:
People think they're eating Italian food, but it's Albanian food.
Eni Jaupi:
Yeah. But we are really good at talking in Italian. So that's could be the correlation there.
Daniel Stillman:
Yeah. Only if you knew what to look for, would you see all the Albanian flags. You're like, "Wait a minute." All right, guys. Thank you so much. This has been a really energizing conversation. I really appreciate it.