# How America Is Exporting Its $40 Trillion Debt Delphi Digital · 2026-11-02 · 55 min · https://www.youtube.com/watch?v=Aru3OC4ewI0 ## Transcript Tommy Did you ever think you’d sell a company to a multibillion-dollar public company? Alex Wilson Absolutely. I knew it was just a matter of time. Like, “Oh my gosh, I’m going to quit my job to go all in on The Giving Block.” Tommy That’s a lot of layered risk. Alex Wilson Really high conviction. Alex Wilson They donated something like $50 million across 50 different nonprofits completely anonymously. Tommy Sounds like the Indian prince giving you money by email. ### Why Start Cyclops Alex Wilson The Giving Block works with probably 70% or 80% of the 100 largest nonprofits in the world. You can buy a ticket to space and pay in crypto or stablecoins through us. I was like, “Guys, rip it up. Start over. We’ll get you live way faster.” Tommy Probably a lot of companies that don’t like you. Alex Wilson Probably not. Let’s say we sell this company for $10 billion. The next company better be $100 billion, right? Tommy I love that. Tommy Alex, welcome to the show. Alex Wilson Thanks for having me, Tommy. Tommy You’re the co-founder of Cyclops. You’re also the co-founder of The Giving Block. How’s your day in Florida going? Alex Wilson Good. I love it here in Miami. We’ve got a nice, sunny day. Tommy Your co-founder doesn’t live here, though. Alex Wilson No. Tommy He chose wrong. Alex Wilson Yeah, he chose wrong. He came to Florida briefly, then he bailed on me. Now he’s in Nashville. Tommy It’s crazy. You could get investors excited about that, you know. Alex Wilson The other co-founders are in Michigan, too. David’s in Michigan, so— Tommy Started from a pretty low bar. Alex Wilson Yeah, exactly. Tommy I think you should get paid more. Alex Wilson Probably. Tommy You’re anchoring the company. Alex Wilson Really? The best state. Tommy Exactly. So, we’re going to go through your life story, but when you started, did you ever think you’d sell a company to a multibillion-dollar public company? Alex Wilson Absolutely. I knew it was just a matter of time. I’ve taken a lot of shots and started a lot of companies. I know we’ll go into that, and it definitely won’t be the last time either. Tommy I like that. Walk me through how you got started on the entrepreneurial kick. When we did some prep work, you mentioned buying and selling stuff on eBay. You did a bunch of jobs when you were starting out. What got you into that mentality? Alex Wilson I always really wanted to make a lot of money. That was kind of the starting point, honestly. Tommy “How do I make as much money as possible?” Alex Wilson Pretty much. I was interested in making more money from an early age. I grew up in a pretty average household. We didn’t have a lot of money, and we had our own ups and downs. I always knew there was more out there and wanted to help my parents financially, too. From an early age, I was always hustling, and my parents were super supportive of that. Tommy That’s nice. Alex Wilson They were pretty entrepreneurial themselves, too. They never had any big hits like we did with The Giving Block, but they always encouraged us. They’d say things like, when you see Elon Musk on the news, “There’s no reason that can’t be you in 20 years.” There’s literally no reason that can’t be anyone. It’s all out there for the taking. You just have to go for it. Tommy How much do you think your parents being that supportive helped you? Do you think you would have figured it out anyway? Alex Wilson I think it’s one of those things where it’s very hard to say. I think it would have turned out very differently, because most people wouldn’t even be comfortable thinking that way. They just think, “Okay, I’m going to go to school, get a good job, be a management consultant or investment banker.” That’s how you make a lot of money—the more traditional path. Doctor, lawyer. Tommy Yeah, exactly. Alex Wilson That extra push of “You should just try stuff” made a difference. It doesn’t matter if you’re 14 or 15; you can still make money. The other thing I heard all the time was, “Oh, well, you’re so young. You don’t need to worry about making money now.” I was like, “Well, if I make money now, I’ll make even more money later.” Tommy What was your first business? ### The Door-to-Door eBay Hustle Alex Wilson There were a couple. One of the more interesting ones was a business buying and selling domain names. I basically just read about it online. This was when I was in high school. You saw domain names starting to sell for a lot of money back then. I still remember some selling for millions of dollars in the news. I read a book and researched the best way to run a domain-name business. At my peak, I was selling hundreds a week. I was registering them on GoDaddy for $78 each. Often, I was only selling them for $20 or $30, sometimes a couple hundred dollars if I had a good one. I was really just doing volume. It was pretty fun. Tommy And that’s a lot of money in high school. Alex Wilson Yeah. Tommy You don’t have any bills, so— Alex Wilson Exactly. At the same time, I started some other businesses. There were the classic ones, like landscaping: you rally a couple of friends, shovel some snow, mow some lawns, do some mulching. One of the more interesting ones was helping people sell things online, mostly on eBay and Craigslist. It was really clear back then that older people didn’t know how to use the internet very well. They didn’t know how to sell their car or old golf clubs on eBay, or even a digital camera they weren’t using anymore. It started with finding things around the house that we weren’t using and selling them. That ran out pretty quickly. Then I started asking around and going door to door. I’d ask people, “Do you have something old that you’re not using anymore? I’ll sell it for you. Give me 20% commission, and I’ll handle everything. I’ll pick it up, take pictures, list it, ship it, collect the money on PayPal, and bring you a check at the end of the week or the month.” Tommy I also did the eBay business in high school. It’s crazy because the post office would ship you unlimited USPS Priority Mail boxes for free. You could do the whole nine yards. Alex Wilson Yeah. Tommy Were these older people scared to work with a young high school kid who wanted to sell their stuff? Alex Wilson Some were definitely skeptical, but there were people who stood out as very supportive. I try to be the same way now. If you meet a kid in high school who’s really hustling, try to be supportive. Even when people come to your door selling Girl Scout cookies, I try to encourage that entrepreneurial mindset in younger people and pay it forward. I’ve even gotten involved in Junior Achievement Miami. I’m on their board here, and about once a month I teach a class of high school students about entrepreneurship and the stock market. Tommy That’s awesome. Alex Wilson Yeah. Tommy I’ll take 100 boxes of Girl Scout cookies. There you go—the economy. Tommy As you were running these successive businesses growing up, it sounds like you kind of got addicted to it. But then you go to college, and there’s obviously a gap in entrepreneurship. Did you pick it up afterward, or when did you get back to it? Alex Wilson I never really gave it up. Once I knew I could make a little money and it was working, it just made me want to do it even more. In high school and going into college, I spent less and less time playing sports and doing other things because I wanted to get home and work. I wanted to make some money. I tried to keep that going through college. It was a little harder, but I tried to be self-sufficient and always make enough money to be fairly financially independent, even in high school and college. I bought my own cars, paid for car insurance, and helped with housing expenses, food, and other stuff. Through college, it was more odd jobs here and there. I even picked up jobs on campus that were less entrepreneurial, but I was always working. Tommy Was there ever a time in college, as you got close to graduating, when you thought, “Hey, I want to go work at a company”? Did that ever go through your head? Alex Wilson Yeah, and I actually did. Coming out of college, I got a management consulting job. I knew I wanted to go through the business school at Wake Forest, but beyond that, I was having a hard time deciding what would set me up for the best path for entrepreneurship. I ultimately landed on management consulting, thinking that would give me broad exposure to different industries and problem-solving, and let me meet a lot of interesting people. I did that for a few years and learned a ton, but I was always looking for what the big idea was going to be. It took a while, but I guess it didn’t take that long. Tommy Sounds like a death sentence to put someone like you in a cubicle. Alex Wilson Yeah. Well, at least in consulting, we were traveling a lot, going to client sites and really hustling. Tommy When you were doing management consulting, was it frustrating, like, “I want to go start a business. I want to do a big thing”? Or was it more like, “I’m going to crush this while I’m doing it, but I have this lingering feeling that I want to start my own business”? How was it? Alex Wilson I definitely learned a lot and had a lot of fun doing management consulting, but I was always brainstorming and trying to figure stuff out on nights and weekends. I started trading crypto and rode the 2017 ICO hype wave. It was all just a matter of what I was going to do and when, and waiting for the right moment. Tommy What was that moment for The Giving Block? I keep saying “first company,” but it’s really the first big company. Alex Wilson Yeah, the first big company. Pat, my co-founder of The Giving Block, went to college with me at Wake Forest. We were both living in Washington, D.C. at the time. He was working at a nonprofit while I was in management consulting. Funny enough, he was the guy in our friend group talking people out of Bitcoin and crypto. He was literally making fun of our friends who got into crypto and Bitcoin, which is hilarious. I was the friend trying to talk everyone into it. Tommy It’s crazy you connected despite being on opposite sides of that. Alex Wilson We were friends regardless. We actually became even closer after college than we had been in college because we were living in D.C., hanging out, and were both very entrepreneurial. Pat had a similar background of random startups and things in high school. When we were out in D.C. having beers, we’d always be talking: “Damn, we’ve really got to start a business. What are we doing with our lives?” We were always kicking around ideas. Eventually, I got him into crypto. He always says the “aha” moment for him was reading the Bitcoin white paper. I don’t even remember how I actually sold it to him. I probably just kept talking about it often enough. Tommy He just saw the chart. Alex Wilson Maybe that was it. He started investing a little bit and messing around. Once we were both really hyped about crypto, it was as simple as asking, “What could we do in crypto? What’s a path we can carve out that we’re uniquely able to solve and able to do better than anyone else?” Tommy So, what is The Giving Block? Alex Wilson The idea was, first, that crypto was going to get bigger and bigger. Second, nonprofits are bigger than people expect in terms of market size, and they’re very slow at adopting new technologies. This was in 2017, when we first started talking about it. You can imagine us going to a nonprofit and saying, “Hey, guys, heard of Bitcoin?” There were lots of skeptics at those nonprofits. Tommy “Please leave my office immediately.” Alex Wilson Back then, crypto and Bitcoin donations were just starting to happen. If a nonprofit wanted to accept them, they’d go to something like BitPay or Coinbase Commerce. There were some generic solutions out there, but none were made for the nonprofit market. Even getting onboarded and going through KYB with them was a disaster if you were a nonprofit, because they didn’t understand nonprofits. And then there was the interface. If you made a donation with BitPay, they weren’t giving you a tax receipt. The Giving Block was created to allow nonprofits to accept crypto donations. Tommy Yeah. Got it. I guess I skipped right past that. No, I just want to be sure everyone listening understands. What were the largest nonprofits you worked with, or maybe the most interesting ones? I’m not sure what you’re able to share, but I’m curious. Alex Wilson By now, The Giving Block works with probably 70% to 80% of the 100 largest nonprofits in the world. Wow. The Giving Block has incredible dominance in the market, still to this day. When we started, it went pretty slowly, and we were luckily stubborn enough to stick with it until we got some of those bigger clients, like Save the Children and United Way, as well as big universities. Of course, we signed up Wake Forest, where we both went to school. It’s like the classic momentum you start building: first you’ve got 10, then suddenly you’ve got 20, then 100, then 1,000 nonprofits. Once you become the market leader, it compounds quickly from there. We were the only ones taking the approach we took in the market. We thought getting a button to donate crypto on your website wasn’t enough. Anyone can do that. You need to tailor things to the nonprofit market, like reporting, tax receipts, and how to fundraise. We would teach their fundraisers how to talk to people on X, like Crypto Twitter. We’d say, “Please write Bitcoin as one word. You’re going to scare everyone away if you keep writing it as two words. It’s going to look like a scam.” Lowercase “b,” one word—stuff like that. It was very hands-on. Tommy That’s crazy. So 80% of the largest nonprofits in the world accept crypto using The Giving Block. You mentioned there was a low point, but you stuck it out. What was that low point like? Did you have no clients? Where were you guys? Alex Wilson We incorporated the company in May, with hilarious timing, as the bear market was starting. That first year, honestly, not much happened at all, and we were both still working our day jobs. It was very much a nights-and-weekends thing. Tommy So The Giving Block was part-time for you both? Alex Wilson It was to start, because we had no investor relationships. We didn’t know any VCs. I sent a million cold DMs to people, but no one took it seriously. If you’re a crypto investor, you probably know nothing about the nonprofit market. Most people wrote it off as being too small. We bootstrapped the whole thing and kept our day jobs. Then our day jobs became part-time. Funny enough, when we made the full-time jump, it was the spring of 2020, when everyone was freaking out about COVID. Everyone was like, “Oh my gosh, I’m going to lose my job.” And I was like, “Oh my gosh, I’m going to quit my job to go all in on The Giving Block.” That was an accelerant for us. That was our tipping point. Tommy You’re making it sound easy. That definitely was not an easy choice. Alex Wilson No. The funniest part was that, for those first couple of years, everyone was so skeptical of crypto. Everyone was like, “Oh, see, look, it was a fad. It’s going to zero.” We were just stubborn enough to believe crypto was going to come back and be bigger than ever, so we stuck it out. The crazy part is, you have a global pandemic, COVID, and crypto prices that fell off a cliff. You’re leaving your job to start a company and trying to convince people to sell the crypto they have left, or donate whatever they have left to nonprofits. That’s a lot of layered risk. Tommy Yeah. Really high conviction. Alex Wilson Yeah. Tommy That is crazy. So how did things accelerate? How did you sell the first big nonprofit? How did you get to the point where you thought, “This is what we’re going to do. It’s working. Let’s take that”? ### The $50M Anonymous Donation Alex Wilson The funny thing is that our first 50 clients or so were actually nonprofits trying to accept crypto but using bad solutions. They were using BitPay or Coinbase Commerce and really struggling. We went and interviewed all the nonprofits we could find that were accepting crypto and learned whatever we could about how they were doing it. Something was happening around the same time called the Pineapple Fund. Did you ever hear about that? Tommy I don’t think so. Alex Wilson It was on Reddit. It was a person or group of people who posted on Reddit saying, “I made a lot of money investing in Bitcoin, and now I’m going to give a lot of that money away. Hey, nonprofits, basically apply here.” You can imagine it sounds like the biggest scam ever. Tommy Sounds like the Indian prince giving you money by email. Alex Wilson Exactly. Some nonprofits thought, “Well, why not? Let’s give it a shot. Let’s apply. Let’s go for it.” They donated something like $50 million across 50 different nonprofits, completely anonymously. We still don’t know who it was to this day. Most of these nonprofits had never gotten a Bitcoin donation before and were scrambling to figure it out. So we talked to those 50 nonprofits and asked, “What did you guys do? How did you do it?” They were like, “Oh my gosh, it was a disaster.” Tommy Wait, so the $50 million was donated through old providers? Alex Wilson Yeah. Tommy Your competitors at the time? Alex Wilson Yeah. Tommy And then you go on Reddit and say, “Use us”? Alex Wilson Not even that. We would reach out. This was all happening in parallel. We weren’t ready in time to actually help them with those donations, so we were seeing it happen in real time. A nonprofit would open a random exchange account or find some sort of third party that could process the donations. It was a mess, right? Even the volatility of the donations was an issue. They’d open a wallet, get the donation, and say, “Oh my gosh, wait, now we have to sell it. What do I do?” Tommy It’s crazy to think of. I mean, the $50 million donated is obviously nuts, but that was back then. Alex Wilson Yeah. What’s that $50 million worth today? Bitcoin was between $15,000 and $20,000 at the time of the donations. Tommy $200 million, $250 million, something like that. Alex Wilson Yeah. ### Beating Coinbase by Going Narrow Tommy Damn. It’s also wild to think that Coinbase wasn’t built well enough to accept payments, because at the time, you’re looking at the largest U.S. exchange, and that’s your competitor. Everyone’s using it, and you guys are saying, “No, we can do it even better.” That’s another hurdle that you overcame, I think. Alex Wilson Yeah. Our competitors were way bigger than us. We were a bootstrapped team of a couple of people, competing against Coinbase and BitPay and these other big, well-funded companies. The problem they made—and honestly, in a lot of cases, they continue to make—is that when they offer products like that, they purposely make them generic and broad so they work for a lot of different types of customers. They’re not perfect for any one industry; they just sort of work for everyone. That’s a tricky part about being a big business like Coinbase. It’s hard for them to go all in on, let’s say, the nonprofit market and really specialize. Tommy So, how did you get confident you could beat them? Did you try the product and think, “This will never improve,” or was it talking to the foundations and nonprofits and thinking, “This isn’t good enough”? What gave you confidence that you could beat them? Alex Wilson Just by tailoring it to a market and going narrower than they were. That’s really what it was. We learned what nonprofits actually want and need and said, “We’re going to build it just for them.” If anyone besides a nonprofit wants to use this, they can’t. It won’t actually work or make sense. It was that specific. Tommy It’s awesome. There’s so much layered risk—COVID, the selloff, the competitors. It’s just cool that you guys did it. Alex Wilson The other funny thing was that, since it was bootstrapped, we actually became profitable pretty early on. We weren’t able to raise any VC money until we were profitable and didn’t even really need the money anymore. Things were going well, and we thought, “Let’s raise money, get some support.” We had some awesome guys who were early checks, like Kyle Samani from Multicoin. He was one of the first guys to respond to my cold messages on Twitter and stuff like that. Tommy Yeah, he’ll respond. He’ll argue, but he’ll back you. Alex Wilson Yeah. We had plenty of smart people asking, “Is the nonprofit market big enough? Does this make sense?” All these things. But he was the one to really engage and take the time to think it through, rather than think, “Well, it’s literally called the nonprofit market. Why would we invest in a company that we make money off of?” ### Sold to Shift4 a Year Later Tommy Yeah. So, time goes on, and you eventually sell to Shift4, a multibillion-dollar publicly traded payments company. How did that come about? When we were talking before, it sounded like there wasn’t that much time between starting or raising for The Giving Block and then selling it. Alex Wilson Yeah. We started in 2018, raised at the end of 2020 going into early 2021, and then ended up selling on March 1, 2022. It’s crazy—a year, door to door from raising to selling, pretty much. We hadn’t even spent most of the money we had raised yet. We were already profitable, too. Back then, valuations were very different. We raised $1.5 million at a $10.5 million valuation. Tommy Wow. A VC’s dream: $10.5 million and an exit a year later. Alex Wilson Yeah. And the thing was, we weren’t actually planning on selling at the time. We were thinking, “Things are going so well. Let’s try to get some investments from strategic partners and really get dialed in on some of these key relationships.” Some of those conversations turned into, “Rather than invest, would you guys consider just selling the company?” We were like, “Maybe. We’ll always hear you out,” but it wasn’t really the plan. Tommy When you got—when the first potential acquirer told you that, what was your reaction? Alex Wilson I was really caught off guard. I just didn’t expect that to happen so soon. Then, when it started to happen a couple of times, we kind of got cocky. I was like, “Let’s see what else is out there.” We hired a banker, and then we ran a process. Tommy Interesting. So, you had organic interest in acquiring the company, then hired the banker. Who found Shift4? Alex Wilson The banker actually brought us Shift4. That was awesome. We didn’t know much about Shift4 at the time, and there were a couple of different types of buyers. Our inbound offers were either from crypto exchanges on one side or nonprofit fundraising platforms that weren’t doing anything with crypto yet. Neither exit was that exciting to us because it felt like it was really limiting our upside. If you go to a crypto exchange, you’re just dealing with their customer base; with one of these nonprofit providers, you’re just dealing with their customers. When we started to run the process with a banker, they started bringing payments companies to us, and those had way more upside. It seemed so much more interesting because we could do so much more than what we were doing at the time. It would let us expand to different crypto and stablecoin products that had nothing to do with nonprofits, whereas we felt much more boxed in with those other options. Tommy Despite all the acquisition offers, it sounds like you guys were thinking about this in terms of, “How can we continue to grow The Giving Block?” rather than, “How do we get the best price?” That sounds like a pretty unique take from a founder. Alex Wilson Yeah, it was because it was so early. We felt like it was sort of too early to sell. We wanted someone who was going to help us do the next 10x growth of the company. This wasn’t something we were ready to walk away from yet. We still really wanted to be hands-on and involved, and we were explicit in these conversations: “We’re only selling to someone who lets us stay in control, hands-on, and really see this through.” Basically— Tommy Were they all receptive to that? Alex Wilson Definitely not. I think that’s part of the reason we ended up with Shift4, because it was still a founder company. They had done a lot of acquisitions, and they gave us confidence that they weren’t going to get in our way. That was a huge factor for us. Tommy What were the first times meeting Shift4 management like? Walk me through that. Alex Wilson It was always really impressive. They seemed like they understood everything better than any other buyers we were talking to. Maybe that’s because they’d done a lot of acquisitions, but I think part of it is just that their strategy and management team are incredibly talented. There were a lot of former bankers, as you’d expect, IB guys. The CEO, Jared, was a founder, too. When these guys looked at a company, they went so deep compared to everyone else, who seemed to take a high-level view of it. They also took the unique view that buying us was sort of a two-for-one: They wanted to get deeper into the nonprofit market, but they also needed crypto capabilities, which they didn’t have yet. Most of the other companies were looking at it just through the nonprofit lens. Tommy Got it. Alex Wilson For us, it was more interesting to have both those angles. On the nonprofit side, they buy The Giving Block, and that’s now a foot in the door to most of the biggest nonprofits in the world to cross-sell them on traditional payments. And, by the way, the team can build out things for the Shift4 merchant base that have nothing to do with nonprofits. Tommy Did you know the synergies for them, from your point of view? Did you know that’s why they wanted to buy it? Alex Wilson Yeah. We went through really detailed discussions of what this was going to look like if we went with them. That’s part of what was so convincing: seeing that vision of being able to work on essentially 2 businesses at once. ### From Shift4 to NASA Tommy Love that. So, Jared founded Shift4. When we spoke before the podcast, you said he started his first business at 16. Shift4 is obviously huge. Now he runs NASA. Next-level entrepreneur. Alex Wilson Yeah. Tommy Kind of similar to your story, just minus NASA so far. Alex Wilson Yeah. But I’ve got time. Tommy You’ll get there. What was it like working with Jared? He’s obviously an extremely successful entrepreneur, built a huge company, and is still going. What were the greatest lessons from working with him? Alex Wilson Yeah, he and the team there were super inspirational and really great role models for us. Alex Wilson And by the way, the company he started when he was 16 was Shift4. Tommy So, how old is he now? Like early 40s? Alex Wilson Wow. So, yeah, he really saw that opportunity. Tommy He started a payments company 24 years ago. Alex Wilson Yeah. It was online payments. Tommy Credit card payments were just getting started, basically. It was around 2002. I think it was the late ’90s, even. He was really early in that trend. Alex Wilson But he survived the dot-com bubble, I guess. Tommy Yeah. But an incredible entrepreneur. He had other businesses on the side, and he was also a pilot. So I think he had a lot of dreams about flying in space and all those things. Him getting to lead NASA now seems like a lifelong, or childhood, dream. Alex Wilson And Pat and I—I mean, working for him and working for Shift4, he really brought an Elon and SpaceX mentality to running the business: extreme ownership, extreme accountability, no BS. Everyone was very direct and performance-based, which was really appealing to us coming into a bigger company, where you worry about things being really bureaucratic. I think you see that at other founder-led companies, too. It is a little different. ### Lessons From Jared With the current CEO, Taylor, for example, those guys have worked together forever. They’ve kept that spirit alive at Shift4, which is really impressive. The leadership team has also been generally really impressive. Tommy I think a lot of people might ask you, “What’s the best lesson learned from Jared?” I want to ask you a little differently: In hindsight, after being at Shift4 for so long, what’s the one thing you took away from your time with Jared? I think that might be more interesting. Alex Wilson I think it’s his mindset. I try to be more like him and be disciplined in my thinking, so I don’t get distracted by shiny objects. He really stayed true to what the business was supposed to be doing, what it was good at, and what actually made money. Then there’s holding people accountable and enabling them to do a good job without micromanaging them. It’s hard to pick one thing or one aspect. It’s really the way he operates. We looked up to how he ran the business, and we still think back to those times and draw on them for how we run the business today. We learned a lot. Even seeing him get into the details of a support request was impressive. Tommy I mean, he might not necessarily respond to them, but he’d go in and read them and understand the problems. He really kept a good pulse on every part of the business. Alex Wilson We were always so impressed by how he seemed to know exactly what was happening in every department without being a micromanager. He would understand the problems and go into things to figure them out. He’d come out saying, “Why are we doing this a certain way? It doesn’t really make sense to me. Can someone explain this?” Tommy It’s an interesting skill, to be knowledgeable about everything but also not micromanage, because I think your first instinct is, “Well, let me just go start fixing all these things.” Alex Wilson Yeah. Tommy That’s cool. Alex Wilson We try to be the same way. I still do that kind of stuff with Cyclops today. I did that at Shift4 and The Giving Block, too. We try to be hands-on without being micromanagers. ### Hiring to Scare People Away Tommy We’re going to get to Cyclops next, but just on the Jared question: How did working for Jared change your management or entrepreneurial approach with your new company, Cyclops, versus The Giving Block? Alex Wilson We spent a lot more time from day one thinking about the culture, the principles of the company, and what we wanted people to think made a good Cyclops employee or team member. We address that head-on, even in the interview process. We think it’s as important to scare the wrong people away as it is to attract the right people. Even in our job descriptions, we say, “Don’t come here if you’re looking for a corporate nine-to-five job. This isn’t it.” Every person we hire has to interview with one of the co-founders. The number one thing we’re trying to do is scare away the wrong people. I go in there telling them, “Oh my gosh, this is going to be so much work. Are you sure you want to do this?” That’s pretty much the approach we take, because it only takes a couple of slackers to screw up that culture. Tommy So, you’re spending a ton of time on the culture, and you want to hire. How does somebody get through the interview process? Who impresses you? What kind of person? Alex Wilson They have to proactively bring up the traits we look for, like ownership and accountability. They have to seem like they love the startup grind and hustle. Anyone who’s like, “Oh my gosh, I can’t believe I had to have a late call yesterday,” is so out. Tommy I know a bunch of people on your team, and they’re all killers, so it’s good to know. Okay, so you guys started The Giving Block, got acquired by Shift4, and kept your foot on the gas building for years within Shift4. Alex Wilson Yeah. Tommy And then you decide you want to start a new company, Cyclops. There are so many questions around that. Why start Cyclops? Why not stay at Shift4 and keep doing what you’re doing? What’s the difference between Cyclops and Shift4? Walk me through that. Alex Wilson We stuck around for roughly 4 years after the acquisition. Tommy Long time. Alex Wilson It was a long time, and probably longer than we expected to stay. We were always very open with them that we wanted to start a business again at some point. This wasn’t the last business we wanted to do, but we wanted to see this through, stick around, and make sure things went well. I was mostly focused on building stablecoin solutions for the 200,000 merchants Shift4 had at that time. We looked at things like stablecoin settlement, payments and payouts, and different treasury use cases. To do that, you do what everyone knows: go out to the market, talk to all the different providers, and stitch together a solution. It’s funny how similar this ends up being to The Giving Block, and I’ll get to that in a second. Basically, 4 years into it, me, Pat, and David were sitting around complaining about how bad everyone else was and how difficult this was, because it should be so much easier. We were like, “Okay, we need to stop complaining and just do this. Why don’t we just do this ourselves? We’ve lived the problem we’re trying to solve for 4 years. Why not? Who’s going to solve this problem better than us? No one.” Tommy Just to be specific, so I understand: Shift4 would handle payments on the crypto side. You had to stitch a lot of providers together, and with Cyclops, this is the solution to use? Alex Wilson Yeah. We would go out and get on- and off-ramp providers, wallet providers, and transaction monitoring. Suddenly, you’ve got 5 to 10 different providers pulled together for, let’s say, a pay-with-crypto product or a stablecoin settlement product. You need an engineering team to manage all that and keep it together, plus the contracting and onboarding with each provider. It gets very messy very quickly. Maybe the biggest problem of all, very similar to The Giving Block, was that no provider was building for payments companies. They were all going very broad, and we said, “This is crazy. Payments is a huge industry. How is no one focused on this specific industry and its use cases?” Tommy How many providers did you have to stitch together? Alex Wilson Usually, you get an on- and off-ramp for the U.S., and then for every other major geography you want to work in, because many providers aren’t very global, or they say they are and the solution isn’t very good globally. Then you have a wallet provider, plus a redundant wallet provider in case something happens. Then you’ve got all the different compliance stuff, like Travel Rule vendors, Chainalysis or TRM. It’s dozens of providers. It’s a huge stack for building these crypto rails and crypto payment solutions. And so our idea was: Let’s go narrower by just working with payments companies with a profile like Shift4’s. The second piece is that, because we’re much more purpose-built for them, we can be an all-in-one solution. They have one relationship with us, one onboarding, one integration, and everything can be white-labeled and ready out of the box. They don’t even need a crypto engineering team. Part of the pitch was, “We know you guys aren’t a crypto company and probably aren’t going to become one. You don’t need to hire 20 crypto engineers to build this product. Let us—” Tommy So Shift4 comes to Cyclops, your new company, the one you’re currently running, and they say, “We want to accept crypto payments”—or, sorry— Alex Wilson Yeah. Well, the Shift4 piece is a little unique, because they became an investor and a client in Cyclops. So that was a big anchor customer for us. But other payments companies say, “We want to start settling our merchants in stablecoins.” Alex Wilson That’s the number one use case. The others are that we want to allow our merchants to accept crypto and stablecoin payments on the checkout page. The third use case is that we want to pay out—or our merchants want to pay out—their customers in stablecoins. This could be a marketplace for gig workers, an Uber or DoorDash kind of company, a payroll or contracting platform, or even a casino paying out winnings. There are a lot of cases for paying money out to people, especially if it’s global. Stablecoins can make sense. Tommy It’s kind of crazy because, in my crypto-native head, sending a stablecoin is so easy. It’s like, “Give me your wallet address and I’ll send you a thousand bucks.” But from your point of view and what you’re building, there are dozens of providers. It’s a very messy process. It seems very complicated, like two very different worlds, because when I think of payments, I think of it as so easy and crypto-native. ### A Ticket to Space in Stablecoins Alex Wilson Yeah. Part of it is because we’re operating in such a highly regulated environment, and it’s so B2B. It’s not like you and I opening a wallet or an exchange account and figuring it out because we’re crypto-native enough. This has to be an enterprise-grade product that can be white-labeled and rolled out to hundreds of thousands of merchants. It’s just a different scale and a different kind of expectation for how things work. Tommy What’s a customer or company that listeners would know that you work with and enable? Alex Wilson Maybe one of the cooler ones we’ve worked with is Blue Origin. You can buy a ticket to space and pay in crypto or stablecoins through us. Tommy How much does a ticket cost? Alex Wilson They don’t disclose the price publicly, but it’s millions of dollars for a ticket. Tommy So if I want to go to space, let’s say it’s a million bucks, and I want to buy that, I go to Blue Origin’s website or something, check out with crypto, and you handle that process? Alex Wilson Exactly. Even for that, the interesting use case is that it’s usually people from outside the U.S. who want to pay in stablecoins for these big transactions. In general, most of the consumer payment use cases are in the high-end and luxury markets. The reason is that non-U.S. people don’t have U.S. dollar-denominated bank accounts, but they have an invoice they need to pay that’s denominated in U.S. dollars. For them, sending a traditional wire from wherever they are means crazy FX fees, and it’s slow and opaque. Tommy I mean, us sending wires in the U.S. is annoying. Alex Wilson Let alone. But it can be 2%, 3%, 4%, even 5% for some of these international wire transfers if you don’t have the right banking setup. But you can access stablecoins pretty much anywhere, so it’s almost always much cheaper for them to use stablecoins they already have, or get stablecoins and settle the invoice that way. ### Who Stablecoins Cut Out Tommy As Cyclops grows, there are obviously so many fees with payment processors and wires—2%, 3%, 4%, 5%, like you just said. There’s a lot of money being taken away by third parties like banks and everyone else. It sounds like if you’re able to enable stablecoin payments at scale, you’re returning a lot of money to the consumer and the end business, rather than to middlemen. Obviously, Cyclops is a middleman, but a more efficient one. How much money in aggregate do you think you’d return to the world? Do you think about the global scale of your business in that sense? Alex Wilson Yeah, a little bit. It’s really hard to say because who it gets returned to and when it gets returned to them is going to vary a lot. I think when people think about crypto and stablecoins disintermediating companies, they take too broad a view. Even with payments companies, which I think most people would consider a sort of middleman, I don’t think payments companies are going away anytime soon. I actually think payments companies like Shift4 are best positioned to benefit from adopting stablecoins and crypto rails. The ones more at risk of being disintermediated are these other random middlemen beyond them, like some banking partners and even some of the networks. Shift4 and other payments companies can cut out their middlemen. As payments companies, they have distribution to customers, so they’re really well positioned. In some cases, their margins are better on stablecoins because they’re getting the margin their partners would have gotten. Tommy Got it. When I think of stablecoins and payment companies, I just think Amex won’t get its 2–3% anymore, whatever it is. Alex Wilson The consumer side of it is hard. I don’t think the consumer side changes too much. Call it 80–90% of what we’re doing is really B2B flows. We all love our credit card points. We love our lounge access from the credit card and the cashback or whatever. It’s a zoo now. Tommy I know. ### Agents Need New Checkouts Alex Wilson It has gotten bad, but I guess the biggest thing is that I really don’t think consumer behavior changes that soon. The real opportunity here is those B2B flows. Tommy Makes sense. Obviously, agents are all the rage: Hermes Agent, Muse, Instinct, Dots. There are too many to name at this point. How do you think about payments and money flows for agents? How does that affect your business? How do you enable it? Do you not care? If a billion people have an AI agent, are they interacting with Cyclops or not? Alex Wilson We spend a lot of time thinking about this. The shortest way to put it is that everything we build and do at Cyclops is designed with the expectation that a much larger portion of commerce will be done by agents in the coming years. Today it’s still relatively small, but we’re very confident that it’s going to be a lot bigger every year. Everything we build is built with that future in mind, and part of what we’re doing with these payments companies is making sure they’re ready for that future. If you scrape the internet for merchant checkout pages, so many of them can’t even be used by an agent because they’re outdated and poorly built. As part of our implementation with these companies, we’re getting them what we call more AI-ready. We’re almost auditing their products and checkouts to help them with that. We don’t think all agents are going to pay in stablecoins, but there are going to be a lot of use cases where they do. It’s going to be a mix of fiat and crypto. Tommy I like that. The other broad stroke I want to talk about is why stablecoins are so important for the U.S. That’s a big macro trend for you guys because it seems like it just helps the business overall. What’s your general geopolitical take on stablecoins? Alex Wilson The growth of stablecoins is a great tailwind for us. I think a big reason—and I don’t think this is a secret—that this administration pushes stablecoins so much is because they’re good for the U.S. dollar, essentially. I forget if it’s 80% or 90%, but I think 90-something percent of stablecoin supply is U.S. dollar-denominated. It’s almost all USDC and USDT. Tommy I assumed it was near 100%, to be honest. ### 200 Currencies Down to 25 Alex Wilson Honestly, it’s 90-something. It’s probably 99%. It creates this awesome flywheel for the U.S. government: the larger the stablecoin supply gets, the more Treasuries the stablecoin issuers buy, which brings down rates or at least tries to keep them down a little bit. At the same time, it’s dollarizing all these other economies, because people around the world who don’t have access to a major currency want U.S. dollars. It’s still the most popular currency in the world by far. Tommy It’s kind of scary for emerging countries. Do you think they’ll just hand over their economy to the dollar? Alex Wilson I don’t think they’re going to go down without a fight, basically. But if you look out a few years from now, we have, I don’t know, nearly 200 currencies around the world. I think it’s probably fewer than 25 even 5 or 10 years from now. Tommy I guess even lower on just a meaningful level. Alex Wilson Yeah. Tommy Five or 10, maybe. Alex Wilson I think it’s significantly lower than it is today. Some of them will start putting up barriers. The central banks of these countries will put limitations on it because they’re going to see this happening. But so much international business is already done in U.S. dollars, and if it just keeps getting easier and easier, there’s going to be less and less reason to use the local currency. Tommy It’s kind of crazy. We have so much debt, like $40 trillion in debt, but the dollar is becoming more important. It just seems like opposite things, right? Alex Wilson Yeah. I kind of think about it as a way of exporting the debt, or at least kicking the can down the road a little bit longer, right? Tommy Kicking it to someone else. Alex Wilson Yeah, the debt’s still going to be an issue. That’s unavoidable, I think, at this point, but this gives us some more time to figure it out. Tommy So we export the dollar, the issuers like Tether buy U.S. debt, and yields go down a little bit. Everyone seems like they’re winning here except other countries that want their own currency. How does that broad trend help Cyclops? Alex Wilson It helps us in the sense that, one, increasing stablecoin supply is a good tailwind for us because there are more transactions happening and more money moving. But also, increasingly, global businesses are getting comfortable using stablecoins for their day-to-day business operations. There are going to be more businesses locally in these other countries looking for access to those rails and starting to expect that as table stakes for a lot of the ways they run their businesses. They want U.S. dollar bank accounts; they want stablecoin access, and they’re not always able to get it today. Tommy What are you seeing in terms of an uptick in companies internationally approaching you for your services? Is this playing out the way we talked about? Alex Wilson What’s interesting for us is we really just sell to the payments companies, and then they white-label it and sell it to their merchants. Tommy But the merchants they see who are most interested are the more global businesses. Alex Wilson I think businesses that operate in dozens of countries are sometimes the ones most interested in stablecoin settlement, and there are a couple of reasons. One is as simple as they want to dollarize their balance sheets. They don’t want to hold any other local currencies for longer than they need to. Even if it’s not a U.S.-based business, many of the world’s largest businesses are U.S.-based, so their balance sheets are generally in dollars anyway. This lets them get out of the local currency faster or at better prices, at better rates. Or they just want their money faster. Saving money and getting money faster are both great. Very simple, right? ### Seed to Series A in a Year Tommy Yeah. It’s not a hard sell: “I’ll save you money, and I’ll get you money faster.” Alex Wilson Yeah. Tommy It makes sense. So, to close out the Cyclops section, how have things been going? How long has Cyclops been operating? How’s client growth? Walk us through that side. Alex Wilson We only officially incorporated about a year ago, in August. Tommy Well, trends-wise, you should be selling soon. Alex Wilson Yeah, it’s almost time. We’ve gotten our first offer. But it’s gone really quickly. I always feel weird saying we started this about a year ago because it feels like a continuation of the last 10 years. It’s such a natural progression of everything we’ve been doing, from The Giving Block to Shift4 to Cyclops, that it feels like one long project in that way. Tommy That’s cool. It’s a marathon. Alex Wilson Yeah. Last October, we raised our seed round. Castle Island led that. Those guys crushed it. They wanted to invest in The Giving Block, but they just missed it before the acquisition. They stuck around and kept hustling for us in the meantime, trying to be that first call. We raised from them for the seed, and then we came out of stealth as recently as March. We got so much inbound that we pulled forward the Series A. We weren’t planning on raising a Series A this year, but we got so many offers and found so many good partners that we thought could really accelerate the business. Tommy That’s like six months of stealth. Well, even less: you came out of stealth in March and did the Series A in July. Alex Wilson Jesus. Of course, nothing generates more buzz than announcing, so we announced that in July. There’s an unbelievable amount of investor interest, in part because we’re so far ahead of where we expected to be at this point in the year. In terms of customers, we thought, “Okay, we’ve got Shift4 as an anchor customer coming out of this year. Let’s try to get two more big payments companies signed. Three customers would be a great first year. We’d be hyped.” We’re going to end this year with more than 10, way more than we expected. The pitch is really resonating, and things are moving so much faster than we ever could have expected. Tommy What’s the reason it’s going so well? Is it first principles, that this is the right project? Is it your hustle? What is it? How do you get 10 customers when you’re aiming for three? Alex Wilson One reason is simply the product offering and the value proposition. The horror stories we tell about how difficult this was really resonate with the companies we’re talking to. My ideal scenario is that I go into a payments company and they’ve tried to do this themselves over the last year or two, and it hasn’t gone well. There are plenty of examples where they sign someone and might even announce it. There are cases where they signed and announced a deal with one of these infrastructure providers two years ago and haven’t gone live. I tell them, “Guys, rip it up. Start over. We’ll get you live way faster.” Tommy So you’re walking into companies dealing with a disastrous issue and saying, “I could solve this for you. We’ve already built this.” Alex Wilson Yeah. Stop trying to fight to get onto your product roadmap. We have a product out of the box that you can white-label and just use tomorrow, basically. Tommy Probably a lot of companies that don’t like you. Alex Wilson Yeah, probably not. We’ll see. But we’re really excited by how much this is resonating, and we’ve built an awesome team. I give a lot of credit to the team. It’s honestly been a lot of fun building again. ### Swinging for a $10B Exit Tommy What’s the long-term vision for you? Do you still want to grow this forever, or are you more of the mindset that you’ll sell eventually? Where do you land? Alex Wilson We definitely want to exit at some point. I don’t see this becoming a family business that we try to pass on to our kids or anything like that. But we think we’ll have a lot of optionality even in the next three to five years. We think it’s a pretty short timeline before we’ll have a lot of opportunities to exit. That doesn’t mean we don’t take it all the way to an IPO, but this needs to be a massive exit to be interesting to us. We had one good exit already, and we’re not in a rush to sell again. We’re going to really swing big and push it. This needs to be a $5 billion or $10 billion exit at least. Tommy Could you speak to the point that you’ve already exited? Could that slow you down in some instances because you’re comfortable, or could it speed you up and direct you because you don’t have to worry about money as much? Where do you land on that spectrum, Alex? Alex Wilson It’s more of the latter. It’s an accelerant. There are so many things you’ve learned that you don’t have to worry about, like having a team in place. Now we have investor relationships, and we can raise money. We couldn’t do that before with the last company. Tommy A lot of the day-to-day personal-life stuff is covered after the first exit. Alex Wilson And also, us three co-founders are the kind of guys who always want to go bigger. Let’s say we sell this company for $10 billion. The next company better be $100 billion. You’ve got to keep leveling up. Tommy I love that. How do you divvy up the work between co-founders? Who does what, and how did you figure that out? Alex Wilson It happened very naturally, and I think it worked so well because of how different the three of us are. We could not be more different. Pat, the best way to describe Pat is that he’s— Tommy Hates crypto. Alex Wilson He hates crypto, or used to hate crypto. Now he loves crypto. He’s one of us now. Tommy He’s one of us. Alex Wilson He’s much more the creative mind, the marketing mind, the big visionary. I’m much more focused on the product and partnerships, and the more tactical, day-to-day running of the business. Then David, our third co-founder, is handling basically the compliance, legal, and regulatory side. His background is as a lawyer. The way we met David was that Pat and I were looking for office space in D.C. when we started The Giving Block and came across his incubator. He was running a blockchain incubator and coworking space in D.C. as a side hustle while he was a lawyer. Tommy Everyone’s doing side hustles. Alex Wilson That’s how we met him. He sort of became an adviser to us, and then we hired him as a lawyer too. He helped with the deal with Shift4, and then we convinced him to join us full-time at Shift4 after the deal as a lawyer. He was kind of the crypto lawyer at Shift4 and became our right-hand man on all those projects. He was really betting on being a co-founder and part of whatever we did next, so it all worked out really nicely. We make a great team, and honestly, we have a lot of fun together. We’re great friends. Tommy I love it. I know we’re friends, but you’re kind of reorienting my founder lens a little bit. I would never want to compete with you in what you’re doing. That’s abundantly clear. Finding founders like you is sort of the north star for me. I haven’t met Pat or your other co-founder, but I’m sure they’re probably similar. Alex Wilson They’ll be here in Miami in a couple of weeks, so— Tommy We’ll have them back on. Alex Wilson Yeah. Tommy Cool. Alex, maybe in closing: you’ve started a lot of companies. There are way more ups and downs than you’re sharing. These are years of very volatile times, very hard times, and very good times. What’s the life advice you instill in people who work at Shift4? You want the people closest to you to be successful, and you’re giving them the best advice you can. What do you try to share with them? Alex Wilson I guess maybe two different things. If people are entrepreneurial, have ideas, and want to start a business, the biggest thing is that most of them just never try. Everyone loves to talk about the great ideas they have; very few actually give it a shot. I think there’s this perception that they have to drop everything and pursue that idea, and I don’t think that’s necessarily the case. The way we built The Giving Block is a great example. One of these new ideas you have can start as a nights-and-weekends project, until you find some product-market fit and figure out whether it’s really something you want to pursue. I would really encourage people to put in the time and effort to give it a shot. It doesn’t mean you’ve got to quit your day job right away; you can do both for a while. It might be a lot of work, so you have to know that coming into it, too. Unfortunately, I think if most people knew how much work it was really going to be, they might not do it. You also have to enjoy the problems you’re solving. Tommy If somebody started a side project at Shift4, do you think you’d back them? Alex Wilson It depends on what it is. If it’s competitive, maybe the answer is no. But I hope we do become an awesome training ground for people to go off one day, start their own businesses, and really crush it. We’d be happy to support them if they want to do that. Tommy Alex, thanks so much for coming on. Where can people get more information on Cyclops? Alex Wilson Our website is cyclops.io, and we’re on all the major social accounts, too. Tommy Easy. Alex, thanks so much for coming on. Alex Wilson Yeah, thanks for having me, Tommy.