121: Founder Mode on Bitcoin: Double the Volatility, Double the Stakes | Will Reeves, Co-Founder ...

It is very unique building on Bitcoin because not only do you have the very tumultuous, volatile journey of building a company, but now you're doing it on top of a protocol that's also volatile, tumultuous, and essentially achieving its own product market fit as well. And so you have these two variables that any one on their own— you can ask any Bitcoin investor and they'll tell you about the roller coaster. You can talk to any startup founder and they'll tell you about the roller coaster. When you put both together, you get this compounding effect. And I will say it is definitely the source of some of the most exciting times and nerve-wracking times of the journey. But, you know, over these years since I've been in this space, there's massive opportunity that comes with volatility, with tumult. And that creates, for people that have that mindset and have that understanding, it creates great opportunities.

Welcome back. This is Welcome back to From Startups to Grownups. My name is Alisa Cohn, and today I'm thrilled to welcome Will Reeves to the podcast. Will is the co-founder and CEO of Fold, a company focused on expanding access to Bitcoin through everyday financial tools. Will and I talked about what it's like to build a company on top of something as volatile as Bitcoin and why that requires a very unusual level of resilience, discipline, and long-term thinking. He shared the story of Fold's early pivot when he realized the company was solving the wrong problem and what it took to help the team shift towards a model that really clicked with customers. We also talked about what founders need in order to endure the day-to-day reality of building, why growth at all costs can be dangerous, and what changed for Will when Fold became a public company. And we got into the deeply human side of leadership too. Imposter syndrome, hiring yourself out of your comfort zone, and how to build a company without losing sight of the life you're trying to create. This is a fantastic conversation, very practical and very honest. Please enjoy my great conversation with Will Reeves, co-founder and CEO of Fold. Will, welcome to the show. I'm so excited to have you today and excited to dive into your journey.

Thank you very much, Alisa. It's exciting to be here. It's fun not only to talk about the business, but also the journey behind it, which is a whole other story that many don't get to hear.

Yeah. Yeah. A whole other story. Well, let's set the scene. You co-founded Fold in 2019, and Fold is a Bitcoin financial services company focused on expanding access to Bitcoin through its services like debit, check it, checking, and bill payment. I got that off your website, but I will just say I myself am a Fold user, so I'm excited to hear all about this. And obviously your company is tied to the Bitcoin roller coaster. So what's that like for you as a leader to go through the roller coaster? You know, 2019, but I know you were a Bitcoin guy before that. What's it like for you to go through that roller coaster?

Well, it's a good day to talk about the roller coaster today because we are certainly on that in the last few days. You know, I've been an entrepreneur builder in other industries before, and it is very unique building on Bitcoin because not only do you have the very tumultuous, volatile journey of building a company, but now you're doing it on top of a protocol that's also volatile, tumultuous, and essentially achieving its own product-market fit as well. And so you have these two variables that anyone on their own— you can ask any Bitcoin investor and they'll tell you about the roller coaster. You'll— you can talk to any startup founder and they'll tell you about the roller coaster. When you put both together, you get this compounding effect. And I will say it is definitely the source of some of the most exciting times and nerve-wracking times of the journey. But, you know, over these years since I've And in this space, there's massive opportunity that comes with volatility, with tumult, and that creates for people that have that mindset and have that understanding, it creates great opportunities.

Yeah, I first thought it's absolutely true. It's always like this plastic time where there's, in times of change, there is opportunity. But I'm just curious, do you think you were like born with a stomach for that kind of rollercoaster or that kind of opportunity? Did you develop that over time? How do you personally relate to dealing with the ups and downs, especially the downs?

Yeah, I think it's a little bit of both. I could probably speak to experiences or times in my life that have, that well prepared me for this. And also other times I believe that to some extent the idea of experiencing volatility, letting it flow over you both as a hardship and a challenge that it is, but also keeping your wits about you enough to understand the opportunity that's there. I believe that can be learned over time. And I think people who are generally open to allowing themselves to face volatility and putting themselves in these situations actually build muscles and strengths that allow them to go to the next phase and the next phase. And over time that compounds. So I'd say it's both something you're born with, but me personally, I've noticed an ability to grow that as well.

Yeah. Can you talk about an experience you had where you really had to let it wash over you and kind of how you came out the other end of that?

Well, those range from deeply personal to, you know, other ways. I think it comes from a lot of places. I think inspiration, and when I made that comment, is driven by moments of failure, trying to do things in the past at a younger age, but continuing to try and having the people around you to keep pushing you to try even with failure. I think it's experiences of loss and losing friends and family and then finding a way to make it through the other side and continuing to, you know, use their inspiration and to move forward. I think it is examples of, you know, understanding what you want out of life and being very clear about that so that you can take calculated chances. So I think a lot of it comes from a combined— I don't there's any one singular formative one, but I've been an entrepreneur before. I've seen what that hero's journey looks like, both in success and failure. I've been a friend and a family member and seen people succeed and lose people. And I think that's a pretty universal sentiment shared by many. And I think if you're able to look at all of these as actual thematically similar, you can create a worldview that, you know, allows you to deal with more hardship than I believe if you just are living a life where you're kind of at the behest of life's challenges, which will bring it to you anyway. So I don't have any single one, but I think a lot of them are really related to what many people have already gone through in their own lives.

Yeah, I think that's so powerful. And let's start really using that, you know, sort of difficulty in your own life as like a learning and like fuel and opportunity. And then I love what you just said about developing a worldview around that. I mean, it's in some ways it is really developing a philosophy about that. Do you have any specific advice for founders in how to, you know, withstand those ups and downs? To your point, just the startup journey itself and grow from them and kind of build muscle around them? Any specific advice or tips or tactics?

So I think when considering this journey of, you know, building a company of any size, many people from the outside may think of it as a, hey, this is a way to make a lot of money or get fame or have power. And most of those things are like an end state they're looking at, and they're oftentimes pointing at individuals after a very long career and saying, hey, look what they've done. Anyone else who's doing this is doing it to get what they have. And obviously some of that is true. But from the actual lived experience of building a company, if that is the only motivating factor, it's not going to work. It is not enough fuel because it is so uncertain. It has so many very harsh 90-degree turns along the way that you'll give up because you will say, hey, that fame I was promised or that wealth looks out of reach now. It's not worth it for me. So the people that I've seen succeed most are the ones who can become deeply aligned at— I don't want to say the word peace because it's not peace, but comfortable in the day-to-day of what you're doing and building. And that comes with a, you know, you're not getting everything you want. It's very much a balance that you need to strike and understand of what's really important to you, what's not, what is realistic given where I'm starting or where my resources are. And so the best advice that I would say is that for builders is that you need to be deeply prepared for the day-to-day and design that as best you can, meaning get the people that you want to work with, be doing the type of work that is going to be interesting to you, because it is only through that day-to-day that will get you through and get you enough satisfaction and to make it through the journey, because it truly is one day at a time. There really are very few overnight successes. And so optimizing for the life you want to live, even though you haven't achieved all the things you want to achieve, is a very hard thing for some people to do, but I think is absolutely necessary for a founder because it's an endurance event. You need to be living in this uncertainty and volatility for a very long time with very little chance of actually the big payout at the end of the rainbow. And so really knowing yourself and designing that, what that cauldron is for that day-to-day, is probably the most important thing for you to do.

Yeah, that is great advice, and I appreciate especially that you sort of talk about— it reminds me of the expression I heard long ago, which is the best way to be an entrepreneur is to fall in love with the problem problem, not the solution.

Yes.

And yeah, and I think that's so important. And, you know, sort of, you just talked about 90-degree changes, a change that you all had to make because Fold's early iteration focused on spending Bitcoin and converting it to gift cards or cash. And then you realized you were solving the wrong problem. So how did you have the insight that you were solving the wrong problem? And then what did you do to make that 90-degree shift or maybe more degree shift in terms of moving towards the right problem?

I think a problem and great thing about entrepreneurs and builders is that they believe that they can bend the world to their will or affect large change through the product that they put out there. Where that goes wrong is not aligning that with the realities, the physics of the actual world and what people want and need. And so there was a moment in the journey— again, I had been a builder before, I knew I wanted to do that. What I found with Bitcoin is this incredible opportunity to align beliefs about what I want the world to be with my skill set. And we had launched the ability to use Bitcoin as real money. It was something that was always said. It's like, hey, if Bitcoin's real, I need to be able to use it places. And so we went out to solve that problem. And as we solved that problem, it was, hey, send Bitcoin and you can shop at Starbucks or Whole Foods or you name it. And we were working through that problem and we saw some successes here and there, but we weren't getting the traction that we wanted to. And so we kind of just went to, I believe it was a Starbucks.. And we're standing in line and we're going to use some new feature that we released on the product. And we saw the line was out the door. And, you know, ultimately what we're trying to do is enable people to get coffee. And we were thinking, okay, our payment method, you know, takes the confirmation times, take a while to process a Bitcoin payment. There's a taxable event that's there. You're not getting rewards like you're doing on a credit card. You're not spending on credit like you are on a credit card. And I just looked around and I said, we're offering a product that is, you know, completely in many ways inferior for this use case what's already working in the world. People love to, you know, for the most part, some of the existing payment methods that are out there. And so we just saw that we're a single person in this big line. We said, well, what do these people actually want? How do they actually live? And we saw that, hey, we're the only ones here because we have Bitcoin and we need to spend it. But 99% of the rest of the people in line have no Bitcoin. We know from studies that they're interested in it, especially in a Starbucks in San Francisco. So what if we allowed them to buy their Starbucks coffee with the same payment method they're used to and they earn Bitcoin? And so now we are solving a problem for a much larger group of people while still introducing and making Bitcoin real, which is part of our core vision, and flip it on its head. And so we just kind of looked at there and saw the world as it was and for a moment took a breath and pause and saying, we need to reconfigure our solution based on that reality. And once we seeded that point to the world and to reality, we were greatly, you know, benefited with success. We had, I think a few months later, we launched a revised version of the product where you earn Bitcoin rewards. And that's really the start of that product market fit, that customers, you know, pounding down your door in a reality where you see it in the charts. It's like this undeniably is what the world wants. What we had before, maybe wrong timing, you know, maybe some other things were part of the issue, but it wasn't that initial problem we were trying to solve. But we found ourselves there as the lonely people in the Starbucks line realizing we were trying to sell an inferior method of payment to people who already had something great, and all we needed to do is tweak that to achieve success.

Yeah, it's so powerful when you're there seeing it with your own eyes. And I think as a founder, it's just so important to be able to really distinguish signal from noise and have that insight, like, oh, not this but that. But then when you go back to the team who were not in the Starbucks line with you, how do you then make the case and get— how many employees did you have then, and how did you then get them on board with this new direction?

It was a handful. It was, you know, under 5 employees at the time.

So it was really small.

Yeah. And so it really wasn't a hard sell. You know, a lot of it was we were already in a point— the whole reason why we were in that line of testing this new feature is because we already kind of had our wits' end about how to make this work. And so it was already readily apparent to the team that, you know, a new approach to our vision was acquired. It just wasn't clear where the direction was. And so ultimately, the insight that we brought back is we found what that direction was. We found how to be relevant, not to the very small amount of people that had Bitcoin back in, you know, 2016, 2017, but that wanted Bitcoin and wanted it in a way that they didn't have to buy it, they could earn it. And that was where, you know, that pitch really was not only something that resonated with our team, but it resonated with all of our partners. You know, Visa, after that pivot essentially was when Visa really turned to us and we became their first partner in the Bitcoin industry to really test this theory out. And we saw all the doors open up, not just customers coming, but partners. The team was more aligned, more motivated.

So it just— you kind of made sense. That's the thing with product-market fit. It's just kind of like it sort of all comes together itself.

And yeah, it's oftentimes it's not very clever tricks. It's very simple tweaks onto things that can open up that reality. And it really wasn't something that took too much because also the way it was essentially just reverse engineering the product that we had already built. Instead of you paying us Bitcoin to then go shop at Starbucks, you use dollars at Starbucks and we give you Bitcoin. And it was very intuitive on the infrastructure point. So it was pretty self-evident.

Yeah. And I think what it does is it also gets people experience with like a low-risk experience of Bitcoin. And I think one of the issues with Bitcoin is it feels scary. It feels sketchy for people. So maybe talk about maybe your own first encounters with Bitcoin and, and maybe share a little bit about the philosophy of decentralization and why that's so essential to this ecosystem.

Yeah, I think like many people, Bitcoin reared its head up in many different ways in my life early, and I was paying some attention to it, but the overall in my early days was, oh, you know, this is cool technology. This is not necessarily necessarily for me, and it doesn't solve a pressing need for me. And I was proven— I later, you know, atoned for that and realized I was deeply wrong about that. But it was largely driven by my experiences, and that spans from, you know, I'm from Sonoma Valley in California. There's a lot of migrant worker work and a lot of remittance back to Latin America, and I was involved in some projects during the wine harvest every year. And some of it was bringing in support— legal, health, for the farmworker population that was there, that was essentially running the valley every year. And a group came up and spoke about Bitcoin, and it was largely of, hey, this is a way to remit value to your family back home without the major fees involved. I thought that was very interesting, useful. But again, I wasn't personally needing a remittance service, so I said, you know, great tool for certain people. I later found myself in Argentina where I was staying with a family and one of the family members had really escaped some major problems with some of the defaults and the inflation there by opting in almost fully with their savings. And it was a great story for him. And I thought it was incredible tool there. But I just said, you know, I didn't see it was directly necessary for me or my family back home. I saw it in the United States. I think during Occupy Wall Street, Bitcoin was being used because PayPal accounts were being shut down and censored. So I thought that was great. It's uncensorable payments. So I saw all these, you know, pieces of what Bitcoin could be, like a kind of mosaic of it, but none of them were directly related to me. And maybe the closest one that I think dominates a lot of the headlines is the crypto bros, this idea of this get-rich-quick or trading thing. I've never been a trader. It's not in my appetite. I don't do that. So that wasn't for me either. But what it did was it developed enough interest in Bitcoin. I kept studying it and thinking about it, and what that ultimately brought me to was not Bitcoin as money, but the money we use today and some of the challenges associated with that money we use today. That, you know, inflation is a very real thing. Purchasing power has been going down. Ultimately, the paths of long-term savings and financial stability have been eroding for younger generations and don't seem to be coming back. Social Security itself is expected to run out in, you know, the 2030s, which is right around the corner. So all of the trusted ways to do it right, to build savings, to build a life, are eroding at the same time as you get the financial crisis and you get the pandemic and you get massive inflation coming in. All of these things came together that ultimately brought me to the point of actually Bitcoin is deeply for everyone and it's— I want to make it part of my life to accelerate that journey that I went on for everybody. And that is what Fold is.

Right, because it makes it accessible. And I just want to highlight a couple of things that you said, which I think are so important. Like the notion of decentralization is what allows it to, you know, sort of transcend like, you know, PayPal or Amazon or whatever it is you're transacting on. And then also it's a store of value, which means it's not subject to inflation. Is that right?

Yeah. So I think one of the major kind of breakthroughs about Bitcoin is that we live in a world that is essentially besides us talking with our friends directly or being in person is mediated by other third parties. Every interaction, every time you pay someone, every time you send a message to someone, every time you get paid by your employer, you're receiving it in a unit of account that is subject to a monetary policy of someone else. It's not this asset from the heavens that is here. It is fully mediated. It is fully manufactured and everything about our lives is. And what that leads to, in some cases it's great, it allows us to essentially not worry about or think we need to worry about everything all the time. Someone else is handling it is, I think, how people would say it. But the danger at the same time is that these third parties have their own worldview and they have their own ways and their own incentives that they are responding to. And those incentives are not always, and most of the time are very rarely, aligned with your incentives as an individual. They're serving somebody else. And so Bitcoin stands in stark contrast to that entire framework that the world sits on. It is a way to transact value over distance, not mediated by a single person. There is no one to inflict their worldview on you. And it is not just for payments. It's also for, you know, being able to opt into a monetary system that isn't a politically charged reflection. Of what's going on in the world. And so in a time now, I think it's becoming more and more apparent that, you know, governments are all looking for ways to become sustainable. They're looking for ways to continue to fund themselves when everybody is running deficits and the math just doesn't math. And so Bitcoin provides this island away from having to trust the worldviews of whether it's people that are printing money or people routing your messages or your value. Allows it to be a kind of island of neutrality, which is such a special gift for this world because it's, you know, it's not that we're saying Bitcoin allows you to go against and do things illegally. Well, you know, it's been used to do things illegally just as other payments have. But really what Bitcoin is allowing you to do is to operate and have optionality in a world where there was no optionality. And so what does that do? It reins in— it provides a counterbalance to fiat money that is printed by a certain group with a certain worldview. It allows you to send money without any of the intermediaries. And so it creates a way to look at the world of saying, hey, what if there was just a neutral place to transact value and to hold value? It's almost like that gives you the vantage point to see how the rest of the world is mediated. And even at that very basic insight that Bitcoin at least allows us to look back at the world we live in and see the benefits and challenges from it, that is hugely powerful. And when those third parties are not behaving well or don't have our best interest in mind, Bitcoin is sitting there as an option for us. And so it is a great thing to keep, you know, the rest of the world in check in some way. And, you know, my belief is that this isn't for big corporations, it isn't for any one group of people. It's truly an option open to everybody. And so far, everyone who has opted into it over a long enough time horizon and has seen the benefits of it.

Hmm. Will, you've said that growth at all costs will destroy you in Bitcoin. You need to be extraordinarily resilient, very conservative in how you're building your company, and be prepared to go into cockroach mode for years on end. And I think that's so interesting because these days there is this sort of growth at all costs mindset which is coming back, right? The sort of the startup world swings its pendulum to, you know, growth at all cost and then get to profitability and then growth at all cost again. Why is that so significant for the kind of company that you're building?

Well, I think it goes back to that first conversation we had about, you know, you're building your business on top of a protocol that is figuring out its place in the world. And so that means that the volatile swings hit you doubly. And it is a time when historically these bear markets would last for years. And it is something that you needed to survive because ultimately Ultimately, anyone building on Bitcoin in any serious way, in my estimation, is taking a long-term view on what this project is. And I think those that have not taken a long-term view and seen it as, hey, I can do something in the next 2 to 3 years and reap the value from that, I think those are the ones that get largely burned because Bitcoin inevitably doesn't live up to their expectations of endless boundless growth up into the right always. And so it means you have to always be looking and preparing yourself for many different eventualities, have a totally different risk model, and be looking further into the future. You know, we intend to be a great American financial institution, and that is only true if we can survive as long as Bitcoin continues to survive. And that means that undue overly leveraging or burning too hot before, you know, paths or sights on profitability can bite you. And many people in other industries who start working in Bitcoin and think, hey, I've done a startup before, don't always recognize that. Because what they don't recognize is there's this compounding risk with Bitcoin that when Bitcoin goes down, it's not just that your new customers may not come as fast, it's also that the whole world says Bitcoin is dead. And so no one is interested in funding Bitcoin anymore. So there is not even the kind of release valve of, oh, we can go tap VC markets again. That option is really off the the table. So I think a lot of people have shown the way, but I think more than anything that has shown the way is you can look at just the sheer amount of startups that have not followed that type of approach to their work and burned too hot, too fast. And Bitcoin tends to humble everybody.

So true. Bitcoin tends to humble everybody. We'll see if AI tends to humble everybody too. But I'm curious, you of course have to shore up as a CEO, you have to shore up your own funding. And I'm just curious if that maybe is why you went public in a SPAC last year. Tell us about the process, the thought process around going public, and what was that process like?

So a few years ago, we were looking at our opportunities where we know that Bitcoin was working on these cycles and we need to make these kind of 4-year plans to really best prepare yourself to where you want to go. And one of the opportunities that we saw was that, you know, in public markets, there really was not a company that represented Bitcoin as a savings asset for Americans. It is not Bitcoin for a high leverage trading or high frequency trading or get rich quick or, you know, all the other cryptos around. There were plenty of those that were public. There wasn't a company that was focused on a more conservative understanding of Bitcoin and approach that it would be the hub for businesses and families that have said Bitcoin is an important part of our long-term savings. We want to convert our paycheck and buy some, and we want to be able to earn rewards on our activity. There wasn't a product out there. And at the same time, from the public markets, it was dominated by this other view of crypto that was, you know, has its own merits on its own, but is essentially speculative casinos in the sky. It is Vegas decentralized and We know the world wants that. It's clear that it has had incredible success, but that's just wasn't what our vision was. It was very different. And what that did was it caused a lot of problems for us because there was no public company out there that was representing a different idea of crypto. That wasn't all these schemes and rug pulls and all the nasty news that comes out of it. It looked a lot like a financial tool that can just help people and we have the data to show it. So we saw and had the hypothesis that if we were able to go public and do that, you know, want to be one of the first to do it, we would open up partnerships and opportunities that were never open to a non-public company before, because there is a halo that comes with being a public company in terms of the rigor of audit and transparency that you're subject to. It makes partnerships and people who are thinking about getting involved or want to find a partner in the space, it really separates you. And so we wanted to do that, but we also knew that going public could be a process in and of itself, and sometimes you can't control the timeline. And so for us, the SPAC really allowed us to have a vehicle that had a more surgical, direct way that we could manage the timeline a lot better than an open-ended IPO, especially, you know, we went public, we were already well along the journey. It was, you know, Comello was the front runner. For the election. Bitcoin, where— what was going to happen regulatory with it was totally up for question. It was definitely not certain. And so for us, the SPAC allowed us a very direct way to do this, to manage timelines and ultimately get us there when we needed to be there. And it was, it was ultimately an investment that we made that, you know, I think paid off. And it's showing off in the partnerships that we've had across the company that have opened up to us that wouldn't have been there without that. So SPAC, it was the right vehicle for the job we needed, which was we know Bitcoin has these cycles, we need to get in and this timeframe and, you know, the rest is history. We've now essentially almost at our 1-year anniversary of going public.

Yep. Happy anniversary. That's great. And I'm so curious, in that year, how did your life change as the CEO of a startup, pretty much essentially, and then into a public company CEO?

That is a very long list. So we're a year in. We've done, you know, 3 of our earnings calls. We've been launching products. We've brought in new partners. We've been cycling out SPAC investors with new investors. And so a lot of my job today is just telling the story to a very different group of people. You know, the audience and the channels in which you do that is very different than as a private company. In fact, you don't really need to do anything on that angle as a private company. Company. And so a lot of my life has changed in, I think, some, you know, scheduling ways. Like, I'm definitely on the road a lot more. I'm talking to a lot more people and very different people than I was speaking to before. But what I always wanted to do when we made the decision to go public is that we were going to be very clear about what our vision was. We were going to make sure the company was well capitalized to handle any storm of public markets. And, you know, we went public the day the initial Trump tariffs. The entire year has been nonstop chaos in other realms since then. And so it really has been something you need to be very flexible, have a great team behind. And really, that's the foundation we set up. And so because of that, Fold has really been able to really stay focused on building what needs to be built. And really, the new stuff is telling the stories to new investors, new partners that has I think, been the most noticeable difference. Before, we also, we had such a great team, and part of the reason why we were able to go public is, you know, our finance team was incredible, our risk team was great, our marketing and product team was excellent, and that allowed us to get through, I think, a lot of the main things that are hard for new public companies. You know, the reporting is no joke, all of the filings are there, but we just had a great team that could handle And again, we're only 50 people, so it's not like we have a massive team to do this. We are still building an operating company, public, growing tremendously year over year, and we made it all work.

Yeah. What surprised you?

What surprised me? I think part of the process that has surprised me are the dynamics of investors. And, you know, you are now at the behest of sentiment, which is a very different thing. You know, private, when you're fundraising, privately, essentially you need to land sentiment in the pitch phase until the check gets through. You got to get someone really believing and then you go away for years and you execute. But as a public company, the sentiment feedback loop is live every single day. And there's a huge delta between what the world is thinking and what you know and what your team is thinking, the wins that your team has. And for structural reasons and for strategic reasons, those two worlds don't see each other all the time. And so you kind of operate in these two worlds always. You have this sentiment that's driven by fragments of things, it's driven by the macroeconomic conditions, it's countless things. And then you have your team, who's the same team that you've been building with, and you say, hey, we need to keep our eyes on the prize. And this number moves up and down a lot, but that's not reflective of what you're doing. What you're doing to you do today will be reflected in the future. And helping the team understand that and myself understand that has been a big growing opportunity, you know, a big opportunity for us and learning curve. But what has specifically, I think, made us ready to, you know, really understand that is that we've been building in Bitcoin for a long time. We have seen a number that you're working on that you care about, but that is moving all over the place all hours of the day. And so we've always had that dynamic. Back a little bit. It's different than when it says your name and directly what the number is right there. So I think that has been surprising on how to motivate teams and manage that wall a little bit so that both sides are happy. Not very easy to do, but, you know, I'd say first year we've learned so much.

Yeah, I can imagine. If there was a founder CEO who was in your shoes a year ago, about to go public on a SPAC, similar circumstances, what specific advice would you give that person? To navigate these challenges that you're talking about?

I mean, the strongest advice is to have the best possible people around you. And so the only way to make that ROI or investment pencil out at all is if you know you have a team that can compound the value that will come of it, not just get the one-for-one value on the other side. You need to have a team that can actually compound out of that. And so it would be, you know, your numbers might be great, because there's some tailwind in your industry for a couple quarters. You might have a great roadmap that you're talking about. You might have a lot of things. But if you do not have a team that specifically is geared to reaping the bounty of being a public company, you're gonna miss a lot of the opportunity that's there for you. But also you're gonna probably get bogged down in just the day-to-day of operating a public company that's gonna take you away from the actual work at hand.

Yeah, because you really need your team to be surrounding you to do that. I'm just curious, how did you learn how to hire the right people, the right executives? I mean, you have 50 people, but I know that you have a small executive team around you. What have you learned over the years, the hard lessons about hiring executives?

I have learned many. So first one, I learned in a very painful way that I need to replace myself and I can't, as the CEO of the company, You know, I think you see a lot of especially founder CEOs have this issue where, you know, you come in and you're building with a very small team and you're doing 40% of the work at the company. You know, you're a product, you're an engineer, you're great at marketing. And then as you start to scale, you realize how much work the CEO job is just keeping it together. But at the same time, you're, you cling to what you know and you try to hold on to your safety, which is maybe your core skill set. For me, it was, you know, in product management and, and product design. And I clung to that for way too long, and that made me delay hires that were needed to come in much further along that would allow me to step away and do more with myself, but also get someone in there who's better at it than I could do, but also is dedicated to it. And so I'd say that any safety areas, you need to focus on those specifically, because everyone knows, you know, everything outside of area of expertise, you're like, I need to get the best. Okay, that's an easy thing to understand. But when you're talking about, I need to get the best, and that's my job today, a lot of people don't let go of that. And they don't let go of it primarily out of making themselves feel like they still know everything and they're still an expert in their field, when the CEO role is calling and it's about to show you and humble you about everything you don't know. And you need to go on that journey and learn that as fast as possible. And so hire yourself out of your comfort zone is so important. The other part is that, and this is a compounding effect, where in some cases hiring someone who you believe is better at whatever that core skill set is that you had, hiring someone better than you are for that, then allows you to use that person as a bellwether for competency across the organization. So very quickly they're going to start to say, I need someone who has this much hunger or this much skill set, and then you need to make changes and you need to upskill in other places, and you have to follow that chain. And ultimately, that chain is people who have, under a profile that you believe in and a vision you believe in, their expectations just rise across the organization naturally because you're attracting people. And you have these canaries who will start talking when they have people that are not meeting expectations. And so it is a cultural approach to hiring, and it's a lot about really listening to the feedback loop of the people that you want to scale. You want more of those people, be really listening to them and make sure the rest of the organization is serving them. And then once that happens, the rest of the organization is going to look back and have higher expectations. And you need to keep doing that always.

Yeah. It's such a building process. I think that's so powerful the way you described it. And so important, like a great hire then kind of shows you what a great hire looks like. And so then you keep reaching for the great hire more and more and more. And that is of course is painful and challenging. And I'm just curious, in that context, what are the signs to you that an executive is not scaling and not ready to scale?

I think whether it's an executive or IC, I start always at hunger and drive. Like, I really do believe that is one of the easiest and best high signal. Yes, it may not be immediately the most competent or the most knowledgeable, but when you're actually working in a day-to-day environment and the world changes so rapidly, your data changes. Regardless of how competent you are or how much expertise you have or how much experience you had, if you do not have hunger and drive, there are too many things every day that are going to come across your desk that are going to essentially dissuade you from doing your best work. Things will seem impossible or not moving fast enough, and if you do not have that basic hunger, it doesn't work. And so I start there as an initial filter. And, you know, after that, of course, I want to see initiative. I want to see a clear understanding of your own journey, and I want to see what hero's journey you're on. And I want to make sure Fold is a platform for you to see that through. So starting with that drive, that hunger, it all goes out from there because, you know, it's really not about talent. I think that is the thing that is more scarce than talent, is just people who truly want and have intrinsic desire to better themselves and to produce great work.

Yeah, that is for sure. I mean, the truth is that hungry people can learn almost anything, you know, by just by their drive and their hunger. But I'm curious. So if you have someone, you bring people into the company and you hope for the best, you look for hunger, you look for drive, you hope for the best. But what happens if there's a sense of like the executive was good or the leader or the IC was good for that period, but the years go by and they haven't grown and changed? What are the markers to you that like, that is no longer going to work, that person's not going to be able to get to the next level?

Well, on any given day, the territory of a startup increases and it decreases in some ways. You say, hey, we're not doing this business line anymore. That boundary line comes back in and it expands somewhere else. But every day the territory is constantly shifting. And what you'll see with people, even execs who were great at a specific period of time in a company, you'll mostly start in my experience is you will start to see that it is the moment when they stop shifting with that territory change is the moment when they kind of said, this is what I was doing. I successfully did this, but I'm going to be rigid against the future progress or the future state of the company. And it's very normal for that to happen, especially when you're talking over 3, 4 year periods of time, even if you are being successful. And it will show up in small ways at first. It will, you know, "Hey, I'm not interested in this work," or "That's not mine, that's someone else's," or "We need to go hire people," or things like that where you start to see it quietly. But then it compounds on itself into larger things. Whole areas of the business are just not being touched that, you know, would be something very obvious that someone with just boundless hunger and saying, "I'm going to move with the territory," would just take up. And When you see it actively not being taken up, that's a good sign that maybe you've outgrown what you need in that role.

Yeah, those are great. Those are very clear markers. And I think it's also a vibe, right? The founder has a kind of spidey sense of like, is this gonna be happening or not happening? Yeah. Will, I'm curious, in any founder's journey, there's highs and lows. What's one of the highest highs you had and what's one of the lowest lows and what'd you take away from it?

So I'll start with the lows, but they all have a very similar similar thing. Lowest lows are— I think they always coincide. You know, it can start on a product failure or a fundraising failure or a market failure, but they always get to the same place. And it's when you look around and you're saying, there's no one here to save us. We're the only ones that are going to get us out of this problem. It's when financing is out there saying, we're not interested. It is when you miss a new recruit saying, hey, this is too crazy of a time, not interested. It is when a product launch gets gets canceled because a partner cancels on you. And it's an inward process of, we only have what we have here. In the good times, it looks like we're succeeding because everyone's on our side. In the bad times, it's when you look around and it's like you and a couple people. And that's a very scary feeling, especially when you are, you know, stewarding investor money, when you are stewarding careers, all of that. And you look at saying, wait, it really just comes down to what we're gonna do next. That's it. There's no here coming to help us. Here are the resources we have. Here are the constraints we have. Make your way through it. And so those lows really correspond around that moment of, I think it's like loneliness and an initial feeling of hopelessness that then has a very humbling outcome of actually it's always only been what you and the team have and the resources you have there. That's always, it's what it's ever been. Anytime that you've thought otherwise is because things are going well and people are are, you know, fair-weather fans and with you there in the good times. And so for Fold, that has meant deep bear markets, year-long bear markets where nobody's interested in Bitcoin at all. It is partners pulling out of projects that the team had been working on for a year. So I'd say that's where the worst of the worst really has happened. And the best of times, I'd say, are those moments when I think it has been team offsites and team when we've all been together You know, we're a remote company and we are a moment of success and progress and we all get to see each other in the excitement in our eyes that we're actually doing what we believe in, what we love, and it's working. It's the same validation of that pivot we made, knowing that it's not about selling Bitcoin, it's about earning it and seeing the immediate user numbers go up. And so I think it happens in these brief kind of moments, but it's really those that are shared with the team, I think, are the best. So if the commonality of all the lows was this sense of feeling absolutely lonely in the world, you know, you only have yourself and the world is not coming to save you. I think the highs are those moments where you look around and the world is moving in your favor. You have a team that is directly seeing whether it's a product launch or closing of some fundraising or a new customer highlight. Or insight that came through and the team realizes that there's a direct feedback loop between what they do every day and the world getting better in some way. And there's this kind of compounding magic that happens that is infectious for the rest of the team. It's infectious for all those working with our team members. And you start to get into these moments where, you know, instead of— which is most of the world for startups where the world is kind of pressing in against you. This is one of those feelings when you're being kind of lifted shifted. And that at Fold— again, getting back to that original story of pivoting from the spending Bitcoin to earning the Bitcoin rewards— we were not in the best place. We were like, what's the next move? We had the insight, we did the work to form the product to be about Bitcoin rewards, and almost immediately after launch, the numbers were going up, the sentiment on social media was excellent, we were getting great feedback. And the team kind of looked at each other in moment of elation of it's working. We are changing the world and it's working more than anything. Instead of this constant trust us, it'll be true in the future, which is you can do for a while, but the best are when you're confirmed in the real world. And that can happen in many ways. But at Fold, the best days have always been after a major product launch and seeing the success and the feedback loop from real customers.

Yeah, that's really powerful. And I can imagine those real moments of triumph. And it's so rewarding when those things happen for sure. Well, just a few more questions. Have you ever experienced imposter syndrome?

All the time. All the time.

What's that like?

I think the comment when we were talking about how to hire a good team, I had the comment of you have to hire, you know, yourself out of a job. And part of the reason why most, and from the CEOs that I know and founders that I know, most actually don't want to let go of their initial kind of domain because everything else is imposter syndrome. You know, there's not many people who do this job, and there's very few people who do it multiple times. So it's very rare that someone has everything, you know, and something you can't learn at an MBA, certainly not. You have to learn by trial by fire. And so the decision to let go of the safety of your historical domain and skill set and move into the, you know, company builder and CEO is a path of pure imposter syndrome. At least it is, it has been for. And so it's a constant relearning or learning new challenges. And the true test is how fast you learn that.

What advice do you have for other founders as they struggle with imposter syndrome?

Number one, know that is the, at least from my perspective and my experience, that is the only constant with other founders and many more doing it. The very, just the fact is that it's not more widely known because A, as a founder of a company, you don't want to ever admit that. And B. As a founder of company for your team, like you don't have another person working with you on it where you can kind of commiserate. So to the rest of the world, you have to do everything you can to essentially show that you don't have imposter syndrome, but you definitely do. So you're in that. And the best thing you can know is that's the default position for a growth CEO.

Well, what do you wish you had known earlier on your journey?

Replace myself. That just sticks out as such a pivotal thing that I didn't do. But I should have done early. I think it would have materially changed where we are at today. But beyond that, I think there is a, you know, a time when startups go through phases and people may be right for some phases that are not for others. And that's just a fact of life because a startup is essentially speedrunning a company formation to massive scale. And so it goes through what, you know, some companies took decades to go through the startup is supposed to pierce through in a matter of a decade. And so you don't have the benefit of this kind of longer time horizon, which naturally does this. As the CEO, you need to be attuned for constantly tuning the company for this growth that's happening underneath everything. And it's not really obvious to everybody on the team always. So it's again a perspective that you get to enjoy having yourself. It's both very hard reality. It takes hard things to do to act on it, but you absolutely have to, or else you're going to stagnate because you're going to keep the people who are there to solve one problem, even though your new problems are totally different. And so yes, startups can feel like families a lot of the time, but functionally the best ones. And when I mean the best, the ones that just work and that are sustainable and can compete, the ones that have longevity are ones that recognize that there are phases, and that requires turnover, and that turnover is hard, is really difficult.

It is difficult. It's so difficult. And I think so many founders recognize that they wish they had known that earlier, which is part of the thesis of this podcast, actually, to help people prevent unforced errors. My last question, Will, is what advice do you have for other founders as they embark on their journey to grow into leaders?

The advice is that you probably have ideas, and conceptually that it's hard, but it's going to be infinitely harder than that. And it's not only harder in the sense of I have to, you know, walk up this hill instead of get on the escalator. Like, some things are actually like physically hard, but also every day is a barrage of decision-making that needs to happen very quickly and with very limited information. And so the default phase is this is hard, this is going to be very hard. And so at the same time of doing that, you need to create the decisions for your personal life that are able to coexist with that difficulty and that challenge. And so, you know, for me personally, I knew that at the same time of scaling my company and building it, I also knew I wanted to start a family. I also knew that I did not want to have, you know, I was making a big bet on myself and the company. I didn't want to have day-to-day financial stressors also. And so I made decisions about where I was going to live, how I was going to, you know, live my life, how I would raise my family in a way that could coexist with this journey that's happening with the company, but at the same time provide that I want to be building a family. And this is why I'm building this company is to ultimately provide them a good life and an interesting life. And understanding that as a tension that will always be there is one that you don't want to be blind to going in because it's not that you It's not that you can't have a family and do that as long with building a company. It's that these will be in competition with each other. And you need to understand what you're willing to sacrifice on either side. And when you're talking with investors and you're stewarding capital at increasing amounts of, you know, you're going, you need to deeply respect that. And so making sure when you go into this journey that you've designed your life so that you can provide a good life for your your family that will inevitably be under assault from the trials and errors of building a company. Like you need to create that structure and it needs to not be one that you think of as separate from the whole thing because it is almost a finite resource. Your time is finite. Your ability of who you're talking to is finite. And if you've chosen to take this hard path and have a family and you've chosen to raise that family in a place that is, you know, raises the stakes even more. It can really eat you up. And it's not to say you can't succeed because there's many others that have, but it does materially raise potential anxieties along the path. And so, you know, going in with that and designing that you're not just building a company, you are building your life and those around you share that life with you and making sure that they can live in harmony in a way that both are very successful is the hard part. And, you know, a lot of people start this journey young, but when you look at the numbers, the most successful people who are building companies are actually older. They skew older, you know, I'm just under 40, but really you look at the numbers, 50, 60 is one of the golden years of incredible company builders. And when I was, you know, 20-something building companies, I wasn't thinking about these types of things. It wasn't as important to me, but I know that founders are living a life themselves and that needs to be considered in the equation. And you probably need to make sacrifices to make sure that you don't take away from the company, but you give yourself a domain that you can not burn out in, that will be rewarding to you when things are the worst. And without that, you know, it's a bottomless pit. So, it's a thing that you really should focus on is the whole life.

Well, so powerful. Such a great conversation. I really appreciate your wisdom and your depth and your, I would even say philosophical bent. So, thank you so much for joining me. I really appreciate it.

It was great to be here, Alisa.

Thanks for listening to From Startup to Grownup. If you like what you heard, give it a review on Apple Podcasts so other people can find it. And if you know of a founder or someone else who is meant to be on this podcast, drop me a line through my website, alisacohn.com.