E131: Anchorage Co-Founder: Built America's First Crypto Bank

25:23And that bothers me. You left Portugal when you were 24? That's right. So the story is I was actually born in Monterey, California. And I went back to Portugal when I was three years old. I grew up, I did my academic career there. And then Square flew me out of Lisbon in 2011 when I was 24 years old. So you work with Jacques Dorsey? Right. From very early on. So when I was accepted at Square, I think there was 20 people on the team. When I actually joined a few months later, the team had almost doubled. I was an employee of 40. which was pretty fascinating. So I came in. I was really the only person working on the security team at the time.

25:56It was absolutely tiny. And it was a really, really fun ride. What was it like to work with a guy, or for a guy who built two mega companies, Twitter and Square, at the same time? Yeah, so at the time, he was not doing it. At the time, remember, he had been fired from Twitter. This was not a multi-billion dollar, you know, icon that was running two public traded companies. Absolutely not. That's not what it was until 2011. It was extremely polished, like very well-dressed, none of these like beards and like extremely polished, very well-dressed, soft-spoken. CEO with a chip on his shoulder. He wanted to succeed at this.

26:34He wanted to make sure that he was recognized for the work that he was doing. Do you know why? Well, he had just been fired as CEO of Twitter. So that does something to you. So I mean, and you've read the books and you've read everything that just happened around it in all the history around how Twitter got created. But it obviously was extremely hard. And so I would have felt exactly the same way. Like the need to prove myself in something completely different that nobody can actually point at and say, no, he was lucky. Lucky, yeah, absolutely. He wasn't, clearly wasn't. And at Square, he was a great CEO.

27:03He was extremely different than he is today. You did see that evolution. Like, you know, the Jack Dorsey that was like starting to become more quiet in meetings and more quiet in meetings. You started seeing the whole like, you know, only eating once a day. the paleo thing. And then, you know, I think it was the same, ice bath super early in the morning, eating only once a day. Yeah. All those things, you saw them progressively, like, you know, and then the aura ring and then the tracking and then it started getting like what the jack that it is today, you know, tie-dye shirts and this new persona, which is extremely interesting to see, but we saw the progression.

27:37I want to say something, but I forgot. Well, I've learned from him a lot, by the way. He was an extremely good CEO. And right now, having started my own company and I've run my own company. I really appreciate him as a CEO much more than I did at the time. Why? You said, right, you told me the other day, I started to appreciate him as a CEO or him much more when I became myself a CEO. So let me maybe give you a story here. That was, so Square had such great moments. And one of the things that we did is at some point, we were working every Sunday because for four months, Starbucks was coming on the platform of Square and our platform was not ready to actually process credit cards for Starbucks.

28:16And so we really needed to rebuild infrastructure from absolute scratch, little scratch, like new data centers, new bare metal, new machines, everything to kind of like new software stack from the ground up to be able to support the level of scale. And so for a long time, four months, we were working Sundays. If you're working Sundays, really you're working seven days a week because your Friday is also your Saturday and your Saturday is actually your Sunday. And so it's kind of like this thing of like, You're not really like you're on a Saturday, you're working slightly less, but you're working on Sundays.

28:49And so it's kind of like this weird, awkward situation. So we were basically working every day for four months at least. And then it continued. I think the work culture was fantastic and we were working hard, but we saw tons of return from that. So that was amazing. But at some point, people were complaining about at Square, they were concerned about the unsustainability of the pace that people were working in. So especially because like the thing for me, the first thing you say, oh, we're working on Sundays. I'm like, this is incredible. How do you make your employees work seven days a week? You're a founder, fine.

29:20Okay, but like, how do you motivate all these people who all have different motivations? And some of them is probably not, I mean, okay, you're in a startup, you need to work hard, but like, how do you do that? Exactly. So that's number one. It's like, how do you do that? And at the time, I remember feeling excited for working Sundays. You know, how crazy is that? Probably also because you're very young, right? I was very young. I really needed to accomplish something. I really wanted to prove myself. I was working with great people. We were building awesome stuff. But at some point, you know, this was later, but it came from the origin was the working for months.

29:50But the work ethic was extremely hard or it was extremely, I think, good. What happens if someone says, I don't want to work on Sunday? Out. Essentially, I think in a nicer way. And people start complaining. And at some point, there was this thing that we call town square. So every Friday, I had this whole company meeting and there was any question that you could ask. So you'd go out and ask Jack a question. And then people were asking about the work ethic and like, how are we working so hard? So Jack at some point goes up on the stage and says something that was, it was not received well at all, at all.

30:21And so he goes on stage in front of the whole company at Square and says, you know what? The way that I look at weekends are like mini vacations. So the reality is that every Saturday and Sunday, I act and I refresh as if it's a mini vacation. So you should look at every Saturday and Sunday as a mini vacation. And that's how you should recharge. I know you're working very hard, but if you look at it that way, then you're not going to be tired anymore. So even while you're working, what? And so, no, it was like, it was - This is inception gone wrong. No, no, this was post the period of working Sundays.

31:00Okay, afterwards. Afterwards, but people were still concerned about the amount of work that they had and working so hard, working late. And he just comes to the whole team and it's a little bit like tone deaf. At the time I'm receiving this, I was like, think of your weekends as mini vacations. I mean, who says this? And now the funny part is that now, you know, 14 years later, I'm kind of like, oh crap. I understand. I don't understand the, you know, I understand where he's coming from. Like what was behind him trying to do and say crazy stuff like that and where it comes from and how hard it is to run a company and how hard it is to get people motivated and how hard it is to like, you know, there's stuff that's going wrong, but the team really like can't really share fully.

31:40We're very transparent. We're very transparent at Anchorage. We're very transparent at Square. We took a lot of the good stuff from that culture. But it's still like, it's a lonely job. There's a million things that are going wrong in that moment. And then people are complaining that they're working until like, I don't know, 7 p.m. every day. And it's sort of like, just want to tell them to fuck off. You just can't. Obviously, it's not the way to have a great culture. And so, you know, you sort of like, this hits so hard. Fuck off. Oh my God. one thing that is so underrated and I tell everyone who has a normal job is, especially when they start to, when they try entrepreneurship, I'm like, now you understand how when you receive your freaking salary every 25th of the month or 27th or whatever the date is, it's not magic.

32:25There is some idiots behind the scenes destroying themselves, trying to create a service or product, trying to sell market and sell this service and product, dealing with a trillion problems. selling that and then getting paid because there's a cash flow product. All this shit that you don't think about just, oh, but I come here and I work that many hours every day. Yeah, but like input, output, like this doesn't matter, right? Like do you realize now when you're an entrepreneur, you realize like this is like 20 things that need to come together at the same time for you to be able to receive your salary on the 25th of the month, every freaking month.

33:01And if it's one day late, you're going to complain, right? And this is so underrated. And so in Czech, by the way, they did a really good job at aligning people with like, obviously equity, which was extremely profitable when the company went public and got all the way to$100 billion public market cap. So all the early people were extremely well compensated for their hard work. And I don't think any of them are complaining today. And so they were extremely compensated. You have to create this alignment. And he was good at creating alignment. He was good at division. He was good at like rallying the troops.

33:26Like I liked working on Sundays somehow. Like this is cool. And I still do today for what it's worth. So maybe it's like we were odd ducks and he was able to like, get a bunch of early folks that were really motivated to work extremely hard. So that's also a skill, filtering. So I learned a lot from him and that was really interesting to see. And now I have just a different appreciation for what it is to be in that position. What's the key difference between a founder like Jack, Elon, Zuck, who are building companies that truly change the world and all the other entrepreneurs who are doing great, which is already very hard, building a profitable company is very hard, right?

34:06But who aren't changing the world at scale? What's the difference?

34:12At the end of the day, it's really hard to understand for many of these folks what's narrative and what's not narrative. And, you know, in the Jack case, I actually have insider knowledge of who he was as a person and like what's the persona and what's kind of like who Jack actually was in person. We were talking a little bit about how these people on Twitter are one person and then in real life, they're like the nicest people ever. that also happens with these narratives. They're too much in the media. So the reality is that for many of these folks like Elon, etc., the motivations are hard to introspect if you don't know them in person, if you only know them from the outside.

34:42But I would say that it is a different type of beast to go after really hard problems. Spaceships are really hard problems. For a long time in Silicon Valley, you got laughed out of the room if you wanted to raise money for a hardware startup or a defense startup. And now here we are in the world of hard tech. All the VCs are pivoting hard, right? We do hard tech. We do hard sciences. We do defense tech. We're investing in this energy. We're investing in all these things that were just like completely forbidden for over a decade in Silicon Valley. I do think that there's a special type of founder.

35:20I do think those things are still lower EV. Expected value is lower. it's much longer cycle, much higher chances of failing. CapEx obviously is much higher to kind of get into one of these things. So it takes a different type of founder to kind of go into something that has, it's a life's mission. And that's the reason why they do it. Usually people are more driven when they're doing these hard, hard, hard problems. The other ones are just participating in a capitalistic society where they have a skill set and they're building whatever the clients want to buy. And that's totally fine. That's how capitalism works.

35:56And it finds a way. But there's missionaries and there's mercenaries and there's a lot of mercenary founders and mercenary CEOs that they get passionate about whatever came in front of them and whatever opportunity, then you have the true missionaries, which is they actually had the vision before they went and tried to kind of like solve the problem versus iterating on something that somebody was just willing to pay for. So there are different. Yeah, absolutely. Build different. Basically trying the things that are the hardest, which is why the reward is also much bigger because the risk is much bigger.

36:26what's something that no employee can understand ever about being a founder and CEO? I think they can always start a company and so they'll understand it and I think that's what they should do and one of the happiest moments is when I get to fund somebody that came from Anchorage or from some of the companies I mean it's such a great like now they're going to see the journey and in fact I hope that the same way they have a deeper appreciation for Jack so many years later I hope they'll have a deeper appreciation for me hopefully that will also happen that people appreciate it and that has actually happened people have come to me after starting a company and say a year ago I didn't realize how hard this was you made it look so easy in A, B, and C and now I understand you know Z, Y, Z whatever I understand why I hated you but I shouldn't have forget you and tell you well I don't know maybe somebody will come one day I was like I started a company actually it was not that hard you still suck totally that might happen and so So I do think that there's a lot of the lonely job.

37:27We talk about this. The cool part about startups is that there's so much written about it and so much talked about. I do think that loneliness, the startup is already so volatile and there's so many peaks and troughs. In crypto, it's 10x harder. And being a founder of a crypto company that is a startup, then all of a sudden it's just like 100 times harder. And so I think people understand that intellectually, that that's happening. They just don't feel it. Like really that. Look, being a founder is like you wake up every day and you get punched in the face. That's what it is. I wake up and I get punched in the face.

37:59And you really have to have an amazing team around you to kind of have the motivation to keep going because there's many, many days that are just dark days. It's just like, oh my God, this is what I'm doing in my life. On loneliness, I mean, I have like some parts on that because it's so important. The other day you told me there's no downside to starting a company. I don't understand why there's more people who start companies. There's no downside, but there is... I mean, let's start with that. Why do you think there's no downside to starting a company? I think right now, I think the obvious reasons are it's very easy to fundraise.

38:31So lots of capital available. So one of the big portions why companies were so hard to start 20, 25, 30 years ago is venture capitalists wouldn't give you money until you had actual revenue in a business that brought market fit. Nobody was really willing to... They exist, but it was... few and far in between. It was very hard to raise on an idea. Right now we can raise on anything. You see in our industry that people are raising for the stupidest ideas. It's fine. It's a capitalist that works. Some people will lose a lot of money. Hopefully one in a hundred of them actually yield something that is actually interesting.

39:04But capital availability makes it such that you're not really going. You can pay yourself a reasonable salary. You're not risking your own capital, your own savings. It's a lot. It's rare that now you have somebody that's actually digging into their savings and really keeping a company afloat that can actually fundraise for. That's one of the big ones. So from that perspective, the risk-reward is completely inverted. The second thing is that when you're starting a company, the value of the experience that you're accumulating is five times, ten times larger than being an employee. So somebody that has been a founder for three years, in my eyes, has been punched in the face every day for three years.

39:40And they've accelerated their knowledge creation and their maturity five times faster than any employee. And by the way, they have seen what it looks like to hire and fire and retain and grow and do all of these things. And so they also, as employees, they have an appreciation for what it is. Now, I do think that founders generally make for poor employees because they're always looking for the next thing. And the ones that want to do multi-stage founders or the founders that are actually done in multiple times, they're not going to stick around for a long time. But when it really hits that combination of somebody who has already started something or really cares about operating instead of actually founding, those are the best people.

40:19So that Venn diagram are the best. They have the appreciation for how the sausage is made and they don't want to go just leave and start their own thing. And so they're happy with like growing and they feel like growing is, they're doing something great in the world. There's no downside to starting a company, but there are many hidden realities that no one tells you about before you start and that are pretty brutal. One of them is loneliness, right? Mentioned before. I read a tweet the other day from Avishal from Electric Capital that hit really hard. One of the most underappreciated parts of being a founder is how lonely it is.

40:53Founders who have 10 plus years in will tell you almost no one who started with them is still around. You start the journey alone and end it alone. I'm laughing because it's like, it hits really hard. It's why founders bond so tightly with other founders. I 100 % agree. You know how that hit me first? it was so brutal. So from the start of the company, we took lots of pictures. I started in my living room, and so it was Nathan and I, and then Nathan, Buzz, and I. And so we started taking pictures, and every time we moved to offices, we took pictures, and there were dinners and there were lunches.

41:28So the reality is that right now, in this day and age, you have really good photo evidence of the growth of the company. And we put all these pictures in a shared Google Drive. And for some reason, Google, at some point, and some of one of their products started surfacing pictures from four years ago. And so you at some point realize that there's a picture surfaced four years ago and you look at it and 90 % of the people in that picture no longer work. So it's you, it's Nathan, and nobody else is in the picture as part of the company anymore. And that is actually visually when it hits you. It's like, no, that person is gone.

42:04That person is gone. That person is gone. That person is gone. And those are the people you started the company with. Those are like the first 10 employees, the first 50 employees, is the first 100 employees. 10 co-founders. I mean, 10 co-founders, yeah. That's right. It's brutal. And you can see this visually. It's not even just the feeling it because on day-to-day, you don't notice because you're always like solving the next end plus one problem. But when you look at the pictures, it really visually hits you. And so that's actually when I noticed this, it was like three years into the company, four years into the company, seeing Google share a picture of like the first 10 or 20 employees and seeing nobody's here anymore.

42:35How do you feel about that? It was crazy. It was like, why are people leaving me? It's this thing. As a founder, it's really hard to disassociate your identity from the company. I am the company. So if somebody leaves the company, they're leaving me. And I'm sure that in many cases, people are leaving because of me, because either I was the time poor manager or because they didn't agree with the direction of the company or because in one of the bear markets, they didn't have crypto conviction. There's many reasons why people leave. So I'm sure that a percentage of them is actually your own fault and you could have retained them.

43:02And that's actually the productive way of viewing it is I could always retain them. What could I have done better? But still, at the end of the day, you are not the company. People leave and move on for many reasons. And not all of them are your fault. How good of a manager do you think you are? It really depends on the day that you ask. Well, I've gone better over time, which is good. I don't think I've stagnated as a manager. It depends on lots of factors. I think what I found is the way that I'm the best manager is by recruiting people that actually fit my style of management. And so the reality is that I don't try to be a manager that is a good manager across the board in all styles.

43:38Um, specifically I'm a very, very poor manager for people that want participation trophies, the people that want, you know, the, you know, the medal for accomplishing like a pull request today or like the participation trophy or like the little, like, you know, the small little things of like recognition. I mean, we celebrate our wins. We do obviously these things, but ultimately, like, I think people have to really drive, you know, have to, have to drive meaning from their own work and from their own excitement of things that their accomplishment. and these participation trophies are, you know, overused.

44:10Self-starters, basically. Yeah. You need to work with self-starters. That's what I realized with myself. Since 10 years, I'm like, I managed to keep no co-founders or left. Probably tell something about me. Employees, like, I'm a terrible manager. I'm like, I don't have patience. I'm like, I don't understand. I mean, I understand most people just want to make money to like survive, but I don't understand how you cannot be like self-starter. So I don't want to tell you what to do. I'm like, you come here. I need help. If I need to sit down with you and explain the whole thing, your commodity. I need someone who's smarter than me and does the thing better and comes up with it.

44:45But that's not how it works. I didn't realize. By the way, it's not seniority, really. I think you can select for people from the most junior in their career across the board, whether they're engineers or marketing people or compliance. But people are excited to do the work and have some kind of intrinsic motivation is why they're doing it. Those people, I think I'm a great manager, too. I've helped them grow. I really care about where they go. I find them if they don't want to work here anymore. Great opportunities and fund them. I've done it in the past. It is, I think, the people that really are looking for the participation trophies and are just kind of meek and their motivation is really the title growth.

45:20And my friend now became a manager and I also want to become a manager. I have no patience for that and no appreciation for that. And so I'm pretty sure I'm a bad manager for that. On loneliness and on how not glamorous entrepreneurship is contrary to popular beliefs from the media. I saw another tweet the other day. Antonio Martinez, who sold his company to Coinbase. It's so funny. It's so funny because it's so real, right? After the Coinbase deal closed, I popped open a bottle of champagne, drank a coffee mug of it in silence, and sat alone in the office I'd walked into almost three years prior.

45:59It ended more or less like it started. Don't do a startup if you can't imagine in sailing a boat across an ocean alone or settling raw land alone with the absolute hell-bent motivation to get it done no matter what it takes, at whatever risk it costs? You forget that the majority of the outcomes are not successful in this particular case. I don't know what the acquisition looks like, but that is the most brutal part of this. I was talking to someone that had been a multi-time entrepreneur and he had failed three times in a row. And he had spent 12 years of his life, building this, these three companies.

46:37And all of them had failed. And so, I've, you know, I've been lucky enough to have successes. But that is even more brutal. Like the compounding aspect of the majority of these things fail. So true, actually. And it really hits, again, before you said, there's no downside in starting a company. But, when you're in your early 20s, I mean, I had the co-founder of Virtuals, right? Jensen. And he was basically saying very rationally. I went to Imperial College. Then I went to BCG. In BCG, I knew and I grew up without Aircon. If you don't have Aircon in Asia, you don't have money basically. I had like 200K in debt.

47:17So I went to BCG because I can make money and in eight years, I can become a partner and make a million dollar a year. So if I build a business within eight years, I need to make more than a million dollar a year for myself. Otherwise, it's not rational. So I went into business, didn't work, back into consulting a couple of times until like It worked out. But you really have this moment. I remember I was 23 and I mean, I'm Swiss, right? In Switzerland, if you go work for a bank, you make 10K a month directly, right? 10K, Swiss franc a month, which I mean, SF is very expensive. But like for most part of the world, it's a lot, right?

47:53When you're super young. So you're thinking, so I moved to London to start this first company. I was like, it's the best moment to do it because I don't need much to live. I'm 22. 1K a month is enough, right? So I'm kind of safe and I can try until something works. If my model was always, if I go into consulting, I get used to 10K or 15K a month, then how can I get back to 1, 2K a month to build something? But the actual truth is if it doesn't work out, you fucking lost. I mean, you're saying, yeah, you're saying yes. You said five times faster, right? If you're an entrepreneur or an employee, yes.

48:31But let's say you try something and it doesn't work out. you lost a few years, you can say, oh, but I lost, people will say, it's not lost. But if you try to go to corporate world, no one will understand that. They will look at your CV, they will be like, what are you? Like, no one can, they don't understand. Like they have all this, you know, it's like HR department. So there is, for me, I still feel like there is a big risk. It's either you make it, right? And it's worth it. Either, as you said, You compound the failures and then you're, I don't want to say you're a failure, but it's tough, right?

49:10So I think the two fallacies are the following. The first one is slope versus intercept. I think the thought process of, I need to match the million dollars in the next eight years, or it's not a rational decision. It's actually wrong. Because the reality is that if you follow the entrepreneurship path, you are actually compounding something. You're compounding knowledge. You're compounding the ability to create new businesses. You're actually compounding heavily. you're valuing the market in a way that you're not in the traditional financial world. Towards whom? Towards other companies that are in that market.

49:38And that's the second fallacy. It's just like, it doesn't necessarily need to be that after your company fails, that you're going to have to go to BCG and you sort of like wasted three years and then get back into the kind of like, you know, the grind of like the tenure of actually one of these. No, no, no. You can actually go to another company. There's so many successful companies, highly profitable companies that will value your skill set in your three years of compounding. And you're a much, much better business person, engineer, because you've done so many different things. You've actually, you know how to solve problems.

50:06To me and all the companies that I've created and been part of, I really want that. I want to see that self-drive. You just told me yourself, you want self-starters, people that self-drive. Who's better than somebody who's actually tried as a startup? So the reality is that the value to me of those folks is extremely high. Plus something that we didn't talk about is that failure is also relative. There's lots of acquihires in which this is not a failure. Yes, it's your zero revenue. Like you built nothing that a fun product market fit and somehow you're going to make a few million dollars of an acquisition because you're coming as a packaged acquihire.

50:39There's so many of them in Silicon Valley that in fact you can, for a large majority of people, you fill up and you keep filling up. And so the story of a person failing three times in a row in which the failure is literally shutting down the company and ending up with less money than they started. I think that's much rarer. It exists, but it's much rarer right now in Silicon Valley. I mean, think about creating an AI company, attracting any kind of talent that knows anything about AI, and then thinking that you can't package that team and sell it to somebody else as a high multiple, 10x multiple per engineer.

51:12And so a million dollars per engineer minimum acquisition price, maybe$5 million per engineer that actually knows AI. So that's not going to be a failure, neither in the monetary sense, or even publicly. They're going to see you as a successful exited founder. I don't know if this is a particular case, but you might have zero revenue and get acquired into a company like Anchorage or a company like Coinbase. And then that looks like, I don't know, he's had many exits in the past. And so that's what I mean. Interesting. Right now, there's very little. And by the way, finally, the loneliness, the being punched in the face.

51:42Yes, it's a very different experience in being at Boston Consulting Group and doing that job. but that is part of the reason why it has so much value is because it accelerates your growth it accelerates your learning puts you in the position to do so Entrepreneurship is lonely what about life? You talked before about Naval having dinner with him yesterday I think he said something like life is a single player game do you agree with that? I know where it's coming from you know sort of this instinct of like you're born alone and you die alone and everything else is a story that you tell yourself and you can process your brain can process the inputs and you can decide how to interpret them.

52:20And he's right, right? Like having a partner or not having a partner doesn't matter if you can somehow fool your senses into thinking you're happy when you don't have a partner, right? So there's all this like logic to it of the basis, of the core, of the sentence, of the pithy sentence, of Naval, the philosopher, that is actually true. I think the reality obviously is the lived experience is very different. It does feel very different to have a family. I mean, this sense of self-sacrifice, we were talking about it, that there's very few things that you actually are willing to reduce your happiness on, to do.

52:53Like the majority of things, you're chasing happiness. And family is one of the few that you're actually willing to sacrifice your happiness. You're going to be less happy, but you want them to be happy. And so you're kind of sacrificing your personal happiness for the children, for the family. I think that's very special. And that to me feels like it's not necessarily like a single-player game in the larger sense of the description of a single player game. If the objective is to be happy with the family and to do good work and to actually move the world forward, to accumulate knowledge, to create value to the world, you do it in teams.

53:26And so I don't feel that way. I feel even in venture. So building a company, highly collaborative. If you're doing it as a single co-founder, much harder. I've been lucky enough to have the world's most amazing co-founder. What do you think about that? Single founders. I had a bunch of like, for example, Jeff from Hyperliquid at Yoohoo from Kaito. Like they're guys, they're basically single founders. And it's rough. I don't know how they're doing that. Extremely rough. Extremely rough. One of the coolest parts about having a co-founder is that, you know, if there's a sinus of the ups and downs, you're usually not in sync.

54:02And so you're sort of phase shifted. And so the reality is that your high is one of their lows and your low is going to be one of their highs. So it sort of evens out the actual, the shared experience with the co-founders of the experience of the company. And I felt that. I felt that with Nathan a lot where, in fact, when somebody was down on some topic, the other one didn't give themselves the leeway to also be down and sort of like was taking the other side of the equation and like bringing people back up. So doing it solo is much, much, much harder for sure. So I think in my life, everything that I've done has never felt like a single player game.

54:35Even venture investing at Hunt Ventures is a team sport, which is awesome. And I know lots of ventures like Lone Wolf, and it's isolationist and you're doing your deals. In many cases, there's politics about whose deal it is. I felt none of that. I think Chamath was talking about that on Social Capital. He was saying investing is a very personal thing and he was explaining why it kind of like didn't work with like his other partners and at the end of the day, you make your investment decision. And I think both things can be true, by the way. Like, it's very introspective. One of the coolest parts about investing is that it's very introspective.

55:09Like, what do you need yourself to get get the conviction. So what is your taste? What are the things you're looking for? But still, you're working as a team to gather those inputs, people challenging your ideas, people helping you with conviction. I do think that there's a lot to be said of having a team dynamic in which there's truth-seeking, they know you, they bring out the best of you and the best decisions of you. And I do think as a team is much better than on your own. You can get into these like crazy internal loops that it's very easy to pull you out if you're from the outside, but it's very hard to get out of if you're just cycling away in your own mind.

55:43You mentioned Nathan before. You built Anchorage in 2017. Why did you take the leap? At the time, it was kind of interesting. This is not something that, you know, we've always wanted to start a company. In fact, when we were going from... We were working together, right? Together. So we started the same week 14 years ago at Square. And then we went from Square to Docker together. Actually, in the middle of that transition, we thought about deeply about starting a company, which was a security company, key management company. Funny enough, Anchorage is sort of a key management company. So we ended up doing it.

56:13But we thought about it between Square and Docker. We went to Docker together. And then when we were at Docker, there was this crypto fund that lost the passphrase to a$1.5 million Bitcoin wallet and offered me 20 % if I could break into it. So this is actually my introduction while I'm at Docker of like very sophisticated investors who are not very sophisticated at key management. So I started doing consulting. So 300k in Bitcoin for you if you manage? If you manage to break the key. And the reality is that they didn't actually lose the password. They had the seed phrase, but they had the seed phrase generating a different software and it had been many years ago.

56:48And so the reality is that you just needed to go and get the new version of the software and kind of like migrate the thing. So there was not even like a need to bootforce to do anything fancy. That was just sheer incompetence of, or, you know, like, look, it's not their focus. It's not their field. And clearly there was a lot of demand. So Nathan and I, if you think about it, It's perfect founder market fit. I have a PhD in distributed systems and security. Nathan was working on anti-reverse engineering at Arxan. At Square, we had worked with hardware security modules, building payment systems, building hardware, secure hardware, secure payments, authentication, authorization.

57:19At Docker, we're doing key management, distribution of keys. All of this stuff really led to this perfect founder market fit of two security engineers building what is a security product, which is one of the world's largest crypto custodians that is storing private keys for these large institutions. This started because of this$1.5 million Bitcoin thing. It started because of the funds reaching out for help with custody. They didn't know what to do. They wanted to invest in this new thing, but it was weird. It was a bearer instrument. There was no support from the traditional players to help them custody this thing.

57:59it was not a new stock that somehow was like a new ticker on the same APIs on the NASDAQ. It was very weird. It was very prone to being lost. It was very prone to being stolen. And it was extremely awkward to talk to with their LPs. And so they needed to do something. You love 0 to 1? I love the 0 to 1 phase. Why? It's well, it's the phase that it's like the most pie in the sky. Nothing. There's no technical debt. There's no technical debt. you're building something from fresh. It's all ideas. It's all, you know, bright-eyed, bushy-tailed, bright future. The first 18 months of a company are so magnificent.

58:36Hopefully you've raised around and so you have money in the bank for the first 18 months. You're just trying to get to the next stage and the next proof point. And it was just, it's really special. Oh, no politics, really small teams. You're working together, hopefully all in person. And so this no politics thing is always... Hopefully you're in person. Hopefully you're in person. Tell me more about that. I do. Because COVID, remote work, etc. But like, can you work remotely and build, especially build a company that is high performing? So I think the zero to one is the most important phase for you to be in person because you can't really build culture easily remote.

59:13So I do think that the first phase of the company needs to be in person. I do also think that some of the larger companies can be successful with remote. There's lots of stuff they have to build around it. I think Stripe is a good example of somebody that took remote seriously. But if you're that big of a company, now there's a lot that you can do to try to have people be productive and still have a percentage of people be remote, even though they are also leaning towards an office too. But when you're an early stage company, it's just starting out. The iteration cycle, speed is all you have. Speed is all you have.

59:46And if speed is all you have, then being in a room just minimizes the round-trip time of any decision, round trip time of any kind of product, work product. So being in person just makes you a lot likelier to be successful. How about 1 to 100? 1 to 100. It's extremely interesting. It's just a different set of skill sets, different set of muscles. You know, I think it's like a different workout. Just a total different workout that you're doing from 1 to 100. You start hiring people that are experts at their phase, at their fields. you start having to build a hiring machine an HR machine Nathan and I actually interviewed every single employee at Anchorage until we got to like 300 employees and to this day still do it and so it's kind of interesting that it changes the dynamic of what you're building you're building an executive team now you are building these machines that are processes that have to run when you're not there and that's just a different thing running the process and building a machine that runs the process are just two different fields of work and two completely different muscles.

1:00:53I have a question from a friend of mine and I said, hey, I'm going to talk to Diogo. He asked, how do you go from being an employee at Square? Probably a very good employee for an employee at Square. Well, I worked on Sundays so I think, you know, that earned me a little bit of credit. How do you go from being an employee at Square, 24 years old, to becoming a general partner at Throne Ventures, the chairman of the Neur Foundation and the co-founder and executive chairman of Anchorage, which is a unicorn, right? All at the same time, at just 38 years old. I know there's some people that fail up all the time.

1:01:39That's the only answer. It's basically seeing failures. One of the things that when I talk to people who do like, I mean, people I talk to usually do like really big things, it often comes to, listen, I've been doing that for 10 years or 15 years. I wake up every morning super early and I just continue and I never give up, right? And I just continue and continue and continue, which I always use this Steve Jobs quote. It's very boring, but it's, he says 90 % of what separates entrepreneurs that are successful from those who are not is perseverance. Just continuing. Yeah, totally. Look, I don't think there's like much to it.

1:02:16There was no premeditation on how I was going to end up. It was just one day at a time, following the things that I wanted to do, projects that I was passionate about, really working hard on things that I liked. There's not much more to it. I got lucky in so many phases of my life, but one of the things that you can sort of like look at my career, which is a weird one, but it's, I've been doing the same thing for the past 20 years. Which most people don't want to do that. they get kind of bored or tired. I want to do something else after a few years. But if you do that, you start from scratch again, right?

1:02:43You don't compound. That's right. And so I feel like I've been compounding on the same space for 20 years. And I just have had different lenses and different projects around the same field. And the way that it works is I was doing academic research in security and distributed systems as a PhD, right? And so that's distributed systems and security. That's what blockchain is. And then I go to Square to build hardware and distributed systems. Hardware security modules, security. And I go to Docker to build key management and distributed systems and security and selling security. And then I go to Anchorage to build a key management solution that holds cryptocurrencies and Bitcoin as a founder.

1:03:18And then I go to Hunt Ventures to invest in distributed systems and security companies. So the reality is that I've really only done one thing, but I've done it as a researcher, I've done it as an operator, I've done it as a founder, and now I'm also doing it as a venture investor. And the reason why doing it simultaneously actually helps is because it's an extremely good palate cleanser. As a venture investor, you're doing one specific type of work. But if you can have, as executive chairman of Anchorage, you can still make decisions, still part of these board processes, still part of these roadmaps, have these high-level strategic discussions, still help with lending these clients and talking to them and help the product be better.

1:03:58You're making real decisions. You're still an entrepreneur. It makes you better as an investor because you can actually not lose relevance. Like investors lose relevance really quickly, even when they were founders on the things that they're seeing. Same thing for a new foundation. You know, there's not many people that have ran these weird crypto foundations. They're very weird. You know, there's Swiss law. You know, they're creative for all these reasons. They, they're crazy. They have billions of dollars on the balance sheet of these tokens. There's so many crazy decisions that need to be done.

1:04:24And so many decisions that are just weird that nobody has ever had these types of foundations ran before. And so that also makes me extremely valuable for founders, which then is extremely helpful to win deals and to source deals at HuntVenture. So right now, what I feel is like, I don't have three jobs. I only have one. They're just like different parts of the same job and they all help each other. So that's how I've been able to construct. And in fact, I sort of wake up and it's a dream combination of jobs, candidly. And I don't think I would have been happier if I was doing any of one of them in isolation without the other one.

1:04:54So they really help each other. And you can sort of switch. If you're frustrated about something, then you can go operate a little bit or you can go help in some company portfolio or you can go continue to invest and do the N plus one meeting. So you can, it's great. It's such a great combination right now. I feel the energy and I see your banana smile. So I feel like the energy. Have you ever struggled with mental health? No, thankfully I've not struggled with mental health. I think I've not even tried to kind of like, I love when people preemptively and proactively go and talk to folks that can help them think through and be better.

1:05:34Like coaches, I think all of those things are actually extremely good. The one that I've been thinking about is actually when my relationship with my wife is amazing. So shouldn't we start doing couples therapy while it's amazing? So when things are actually bad, it doesn't add, it doesn't tarnish. So that's the thing that we've actually been able to, we've been thinking through doing. We haven't quite triggered it, but I really want to do it. How do we not ruin the good thing? How do we, it's basically prevention, right? It's prevention. Especially if you're working so hard, you're like, I don't want any...

1:06:03You don't want, right now, my life is going so well that it's sort of like, you want to maintain the momentum. And so you're sort of like, and by the way, we talked about travel. Travel is really the hardest part of my job. Travel right now is, I travel a lot. I go, entrepreneurs are, I have to do this. And with small kids, it's just like, they play on your heartstrings. And it's just extremely sad. regarding we'll talk about the travel and the kids later for sure regarding the couple therapy I also saw some other some people who built a bunch of relationships didn't work out and then they said now that we're starting a new relationship we start directly couple therapy right it's not smart it's not when everything goes well or when everything goes bad it's like actually we start now so we give ourselves all the chances very smart too right very smart too And I think one of the things that I've struggled with friends that have done it is that it turns out that even the person that is doing the therapy itself, it's a little bit like dating.

1:07:01Like there's a fit. And so if things are going wrong and you're kind of like shopping around from somebody to help you and you're going through a sequence of people that don't work immediately, you're going to give up and things are going to go bad. But if you're in a good relationship, you're actually like just shopping around for somebody that is a good person to help you. And so you're likelier to find somebody that fits the two partners. And so in that case, then you have higher chances of success. How often do you see founders burning out completely? Because you say, I don't have problems, I'm good.

1:07:30But you invest in founders and it's with founder burnout or even founder, co-founder problems. It's not talked much, but it's very common. Extremely common, extremely common. And you see it once you have like a portfolio of companies. So I have almost 150 angel investments. And obviously now at OnVentures, I'm doing quite a few investments with the portfolio. is actually the sample size is big enough for you to start to see patterns and percentage-wise. Even if something happens like 5 % of the time, I already have lots of reps of what those 5 % look like. It's really interesting. I think the things to be said is, yes, people don't talk about it publicly because it's awkward and it's very emotional.

1:08:09But we sort of in Silicon Valley know how to structure these things. So let me give you an example. There was a company that I've been talking to recently and I was helping them think through this. And one of the concerns that the CEO and founder or co-founder was thinking through is, look, I'm founding this company with these other co-founders, but I've never really worked with them in the past. I've known them, I've never really worked with them in the past. What should I do? How can I do this? I've had bad experiences in the past. And so all of a sudden you're kind of like, okay, look, there's mechanisms of, maybe you don't do traditional 25 % cliff for your vesting.

1:08:44Maybe you do six year. maybe you kind of like set the expectation that next fund around everybody has to reinvest maybe you help yourself to already having this structure work such that if something goes wrong which is highly likelihood if you haven't worked with someone it ends up not screwing the company's cap table so there's always ways for you to just already preemptively doing it but of course look when you're starting a company it's all you know it's all going to be perfect it's all going to be amazing nobody really thinks it through the downsides it's just human relationships it's the third biggest reason why companies failed is founder and finding third biggest I thought it was actually higher on the ranking no no what are the first two first one is lack of product market fit which makes sense the second one I think is they just run out of money so on the way to there to product market fit they run out of money the third one is founder and finding there is a trend in general successful entrepreneurs turn into VC one of them I hate being part of trends it's the current thing I think trend is not the right word.

1:09:45It's basically something that we've seen since a long time, right? But let me tell you the following. Right now, I think I'm the only GP at a crypto fund that has been a crypto founder. So in crypto, that's not true. So there was, I mean, Fred from Coinbase. He really seems to be involved, right? He's a biology company. Now he's back to being a founder, which actually like, it shows like, hey man, like the itch is like, I need to get back to that. But Fred was definitely the first example. It seems like he's now focusing on building a company. But it's kind of interesting. Crypto doesn't have it.

1:10:17I think part of the reason is that there haven't been that many successful crypto companies. And so there's not that many founders to go around. And by the way, some of the founders or DeFi founders got extremely rich because of this weird, misaligned incentives of having early liquidity. So that also kind of screwed up probably some of the pipeline. But you're right that it's very common in traditional venture. Exactly. For me, it was not just crypto. It was like literally like tech and like people move, like shift from one to the other. Why? Part of my internal motivation is actually when you're running a company, you have blinders on and you wake up and you think about the company and you go to sleep and think about the company.

1:10:53And even for me, my angel investment time, it always felt like I was sort of like cheating on Anchorage because anytime that I'm being spent on this thing, does it actually bring value to the company that I raised$500 million for and that I have over 400 employees that I'm working for, it does feel like you're sort of like spending time. It is a palate cleanser. I think it does help the company in many ways. You learn about the market. You have these investor updates, which are very useful on and on and on. But still, your focus should be on this company and maximizing your whole value. As a venture investor, your job is the opposite, is to not have blinders on, is to in fact, look at the coolest things and meet the coolest founders and build the best relationships with the smartest people in the room.

1:11:33That's such a dream job, if you think about it there's lots of downsides being a venture investor um in many cases sometimes you can't actually like go to the depth that you wanted to and really do research on these things and thus you're you know like you're master of none like you're jack of all trades master of none you can like know a little bit about many things and not a lot about one thing which depending on the personality is very frustrating definitely for engineers is traditionally very frustrating but but you get to kind of this awesome life of like meeting the best people smartest people see what they're doing and i've always been passionate about their businesses and like i I want to see how they're growing.

1:12:05I want to see the P &Ls. I want to see how they think about the structure, how they think about the market competitiveness dynamic. And as a venture investor, you get to see them all. And you get to see how the market evolves. And you also feel like you're part of the cool kids club because you have access to information that other people don't. Like you see all of these things, you see all these companies, they come talk to you. And so it's very easy to have this like ego boost of like people wanting to come to you to raise money. And also it's a huge responsibility because many VCs are assholes and sort of like start believing that they're actually the heroes of the story when in fact, obviously, the founders are the only heroes of the story and the only people actually building value are the founders, not the venture investors.

1:12:41Why do you say many VCs are actually assholes? I think it's very easy for you if your job is to just meet with companies and meet with people to become very transactional and to not respect the other party. Because you have the leverage of giving the money or not? You have hundreds of deals that come in. You're going to make some investments into these deals. it's so common a founder meeting a VC is once in a while whenever you're fundraising that's a very different type of it's not something you do on cadence you fundraise maybe five times in your life you said some VCs are assholes that's right, many VCs are assholes why?

1:13:23I think there's actually just the business itself is conducive to starting treating people like numbers there's so many founders that come in that it's very easy for you to get the meeting late to sort of be an interesting about the deck not ask good questions not come prepared that is to a certain extent is respecting their time but when you're doing hundreds of these things a year it's extremely hard to keep also makes sense right if you want to be kind of empathetic also towards them it's at some point i don't even know how you filter through all this stuff like that's right so the job is not conducive to you sort of having like the highest quality human experiences but You have to find a way of doing it.

1:14:01And so there's lots of things that, and then again, by the way, you have leverage. You have lots of leverage. In many cases, by the way, the VCs are chasing and they're chasing the founders because they want allocation. And so this inverts pretty quickly in certain deals. But the large experience that people have with venture investors are people that are not going to get investment. And in that particular case, when it feels like the dynamic of the power is that the VC is default uninterested and you're trying to convince them to be interested, it's very easy for somebody to kind of abuse that power and get there late, not respect the founder.

1:14:31And so it's extremely easy just because of the laws of numbers and treating things like numbers and not giving feedback and not answering back. I get it. I understand the sentiment a lot better now, but it's still a hard thing to do. I had Kiao Wang from Alliance Tao on this podcast a couple of months ago and he said that he loves 0 to 1 like you and being a VC is actually the only way that you can do 0 to 1 50 times a year. That's exactly right. I think as a founder, you do it four times in your life, five times in your life. But as a venture investor, you can do it 50 times a year. And so that's actually pretty cool.

1:15:03And again, look, it comes from like, you won't have depth in those 50 times, but you're going to get to see some really cool stuff. And you feel like you're part of it. And that's a really cool feeling. What about people who go straight into VC without ever building? Why would they do that? I think generally, in fact, that profile, they're better investors. They actually get better returns. How is that possible? It's so counterintuitive. Well, the thing that you have to realize is that when you're a founder and you're evaluating a company because you're a founder, two failure modes. Number one, you fall in love with the product, not with the business.

1:15:38That's a mistake. Number two, you imagine yourself in the shoes of the CEO and what would you do and how would you do it? And you sort of fill in the gaps versus actually listening for what the founder is telling you that they're going to do. You're sort of like, no, no, no, this is what you should do. And I'm going to overlay my vision of what I should do in your mind. And so I'm going to do the best version that I think the business could be, not the version that you're selling it to me. And so you end up making poor investments. A financier will just look at it for what it is. So you're telling me here that you're not the most qualified.

1:16:09I think I just have headwinds. I just have headwinds. The tailwinds are not on my back. But I'm still going to fight those headwinds. You also told me VC has a higher expected value than building. I think that's unfortunately true still. What does that mean exactly? Well, it means that in terms of money creation and wealth creation, there's less variance. So VCs usually are highly paid on a salary basis. They get carry. And so they get an upside on what they're building, which is great. It's aligned. But the expected value is they make many bets. They have a diversified portfolio. And they, over the long term, actually end up making more money with less variance.

1:16:50variance. So the likelihood of them making millions of dollars is extremely, extremely, extremely high. The likelihood of them making hundreds of millions of dollars is potentially similar. The likelihood of them making billions of dollars is lower. And so it's sort of the super, the things that work for the things that truly work. Being a founder, obviously, will be the thing that will return the most, create the most wealth. But in general, for the majority of the outcomes, the majority of the companies fail. And as a founder, you have one company at a time. As a venture investor, you have many bets.

1:17:22And so that is also conducive to just a tighter variance in our expected value. What are the numbers out there in terms of how many founders and how many investors, right? Because for example, because like the logic would be then, except for people who are like very high risk, high reward, which is probably not many people, why would you build a business, right? And if you go, I remember going to a bunch of these conferences, crypto conferences, because we're in crypto here, two, three years ago. And I'm like, there's no builders here. Everybody's a VC or self-proclaimed VC, right? Oh, yeah. And I'm like, how the fuck is this industry going to move forward if everybody's investing but no one is building?

1:18:07Yeah, so it's sampling bias as the investors actually have the time to go to the conference and the real builders are not, they're at home building, right? And so that's actually what's happening. And maybe it's actually a negative signal if the builders are always at the conferences. That's what's happening. So look, in the US, there's what, like 15 ,000 venture investors, 20 ,000 venture investors. And there's way, way, way, way more companies than that and founders than that. Companies that could create on a yearly basis. And by the way, we're at a local maximum of a number of investors and number of venture firms.

1:18:34During 2021 and 2022, there was major, major growth. The market was very frothy. Everybody was making money hand over fist. if the public markets were having these multiples and it made a ton of sense for you to be an early stage investor and for you to kind of like buy these lottery tickets. And so there were lots of funds that were being created. Now the expectation is that lots of funds that raised their first fund in 2021 won't raise their second fund. Or even funds that have been able to raise two funds will merge, go out of business, what have you. One of the things you told me about

1:19:06going into VC, right, is you talked about raising funds and actually that you can make this, if you said basically, people who don't want to have accountability can go into venture in last years. Yes. Can you explain that? So what's happening is that, imagine a job where you, if you can get in the door, you can get in the door and you can convince people to hire you. You are paid a very high salary and you're making decisions that will only really turn out to have been good decisions or not good decisions five to seven years in the future. And so the reality is that there's very little accountability in the intervening period.

1:19:43And obviously, this is a little bit of an exaggeration, but it's roughly true. In fact, you're not going to be accountable for the investments if you leave. And so if five to seven years in, you just move to another fund, you restart the period of inaccountability where the prior funds, they know their investments were not great and know your performance was not great, but the next fund does not know that. And so now you're starting again. And now you have a period of another like five years or seven-year leeway. So technically, if you really want to make money and have no accountability, it's a great place for people that are actually not great to hide.

1:20:14Sounds like... To hide for many, many years. Sounds like corporate politics. Well, it's also true that you can hide at Google. Google, in a large sense, for many years, has been the place where you go to retire, right? And collect the paycheck and rest, invest, and all those things, where people go in and work two hours a day or whatever it is. So you can definitely also hide in a corporate structure. But arguably, most companies that are not Google, they don't have like a money printing machine and really are trying to like get to results. They're better at understanding if you're doing something and there's not going to be an employee at a startup that is going to have five to seven years of doing nothing and being paid and collecting a paycheck.

1:20:50Maybe there are, but generally I think VC is very prone to lack of accountability because how hard it is to have accountability. And it's only getting worse. Companies are only taking longer and longer to go public, longer and longer to actually get into their own. And so I do think at the same time, there's also some tailwinds of things getting better. AI companies seem to be having revenue earlier and faster and growing with less people. And so that's also positive in terms of exits and in terms of potential having your good companies mature faster. Why did you choose Hound Ventures? Do you have VC?

1:21:23So there's three main reasons. So the first thing that VCs have, the large majority of them, is politics. and if you want to avoid politics, you want to work with people that you know and you want to work with a team that is very small. Because politics come from n squared of the number of people and so I've known Katie Hahn for over eight years. In fact, she introduced us to our first general counsel at Anchorage eight years ago when we were starting the company and I've known Katie and worked with her in so many capacities. For example, we were part of the A6Z portfolio so technically that was on our portfolio, right?

1:21:58A16Z led our Series A back in 2017, and she joined A16Z as a GP. We were competitors, fierce competitors. She was not the one who made a decision to invest. It was Chris Dixon, and Chris Dixon was on our board, but Katie was Chris's co-GP at the fund. And so we interacted with her in that capacity. The best capacity we interacted with was as a competitor. She was on the board of Coinbase, and obviously I was on the board of Anchorage. We were on the Libre Diem together. if you recall, the Facebook initiative. So I was on the technical steering committee. She was on the board. So we also worked there.

1:22:34I mean, Sui is becoming a big partner of the podcast. And I'm doing all the founders and I'm probably going to do David Marcus. Yes, what a great team. What a great team to talk to. We were also personal friends. I know Byron and I know her kids. She knows Molly and she knows my kids. And so we've been friends. We've been, oh, and Hunt Ventures is a client of Anchorage, of course. And so we've also worked as a client in... That's what we were saying before, right? That's right. Silicon Valley power, basically. Like it's insane. So we overlapped in like five to six different dimensions. And so known quantity, amazing.

1:23:10What a great, like federal prosecutor coming to crypto. It's a dream, right? And she has a great network. And so when she heard that I wanted to professionalize my angel investment and really start doing capital deployment with more of my time, she just jumped on the opportunity. And it's such a great match. Great brands, a fund that is big enough funds to matter. $500 million early stage funds and a billion dollar growth stage fund. And the team was just amazing and is amazing. And so that was a great match for me. You mentioned before you have to travel a lot, especially for this job. That's right.

1:23:43How does this affect your life? Well, it's really the hardest part of the job. I think partly the job always requires you to travel. I think the fact that I'm in Lisbon has a few advantages, but has a big disadvantage, which is you're actually further. If you assume that the majority of the deals are in New York and San Francisco, then you're further. The reality is that I've actually been able to source great deals from Europe. So that's also been a little bit of an advantage. But the reality of it is I have to be on a plane to come to the US, which is where the deals that matter are. The hard part right now of the traveling is having two small kids.

1:24:14I guess my daughter is just over a year old. So there's not a lot of conversations going on with her at the moment. but my son is almost four years old. He's three and a half and he's already having conversations with me. He asked me where I am. And so one thing that started happening is, which is really interesting, is like he asked me, where are you, daddy? I would say, you know, I'm in San Francisco. What are you doing? I'm working. And then he would go into why. And the moment he asked why, the obvious instinct is, okay, how do I tell them what I'm doing in a way that he can relate to? And so the first instinct, my first instinct was to tell him, hey, daddy's working to make money.

1:24:55And since the conception of money for a three and a half year old or four year old is weird, so that we can buy toys for you. And so that was the easiest way that I thought to describe this connection. Like I'm working so I can buy toys for you. So there was a positive association to it. Unfortunately, that 100 % backfired because this kid, the next trip that I went on, that I was away for a week, gets on the phone and says, Daddy, Daddy, you can come back home now. I don't need more toys. How did you feel about that? It's terrible. I mean, it's just, I mean, and you're sort of like, well, two folds.

1:25:33First, clearly I screwed up by describing the connection to toys because that's not really what's happening. There's a lot more for me to travel while I do this job. I don't have to work. I don't have to work to have this job, right? And so why am I doing it? And so it's a little bit introspective. Like, why am I doing it? Well, I'm doing it because I want to contribute to the world. I want to build wealth. I want to, this pursuit of knowledge. I want to have this self-actualization. I want to feel relevant. I want to work in things that I enjoy. At the same time, I want to have, obviously, be a great father and be a great husband and have this happy family life.

1:26:09Is it possible to combine both? A hundred percent. And when I'm on the ground, when I'm in Lisbon, when I'm with my family, I'm present. I'm present. I spend time. I take him to school myself. Actually, his school is so close to our house that he actually comes on my shoulders. I take him to school on my shoulders. And there's such great connectivity. And I think I've been doing a great effort of actually being present in my children's lives. But it is a trade-off. And you're always having this question that you just ask, which is, is it possible? Am I doing a good job? And I think it is possible.

1:26:39It's just like it requires a lot of work like everything else. What could make you change your way of looking at that? Saying, oh man, actually, I could be a general partner at Hunt Ventures and not be on the board of, or chairman of NIR Foundation or Anchorage and maybe spend a bit more time with my kids, right? I think the two things that would change it are obviously the relationship with your partner starts deteriorating. You feel like you're being pulled away so much and there's so many things that you're missing that sort of starts. And you can feel those things coming, I'm assuming. So that's an obvious one.

1:27:15The second one is your children's education does not go the way you think it should. And sort of they, I don't know, imagine a world in which they start misbehaving or they start having like patterns of behavior that speak to maybe not a presence of a father figure or something like that. I don't know what that looks like right now, but those would be the two things. It's like your partner and your children are starting to behave in ways that you think like your presence could actually evade. And there's lots of things that you can do to mitigate that. So one of the things that I've been trying to do is when I come to the US, we come to New York and try to come for a few months at a time and bring them along so that they're part of it.

1:27:49So there's always options, right? You always have options here, especially when they're small. Exactly. You can move them around. And so I'm exploring all of the above. So far, it's been a great balance. Obviously, I miss them so much when I'm away. But by the way, I work all the time and there's no distractions and it's absolutely amazing and you're super productive on the plane and you're super productive at the hotel and you're super productive. You're meeting all these people and you always say yes. Oh, do you want to come for dinner? Yes. There's no consideration of anyone else. So to a certain extent, that's kind of like your concentrated work and then concentrated family time, which is kind of cool.

1:28:22As mode of operation is actually pretty cool. Absolutely. It makes a bit of sense. What's enough for you? What is what? What is enough? There's not enough. I think knowledge is infinite. And I think wealth is wealth creation and wealth is infinite. And so we should always push forward. humanity is definitely not at a point where i think should uh people should have the freedom to think that they could step back and retire to a beach or whatever it is and so for me there's no i think if we think about it as money i mean i what i already have is already enough but there's so many cool things that i could actually use money for um for example one of the things that i really want to do um my sister lives in copenhagen and um she's a chemist phd and her husband, my brother-in-law, is also a chemist, PhD, and he's a great researcher, accomplished.

1:29:10He's published in all of the big science and chemistry research conferences. And they're great, but they live there. And part of the reason why they live there and they don't live closer to us is because obviously chemistry labs can be everywhere in the world. So one of my ambitions is actually creating chemistry research center in Portugal, in Lisbon, with the sole purpose of being able to move my sister and my brother-in-law close to me and their kids. Because I want their kids to grow up with my kids and I want them to be close. And I don't want to take away one of the great chemistry researchers from the world.

1:29:52And so how do you do this simultaneously? Have them continue to be productive for the world while living closer to you. And so this is actually a solve that can be done with money. So obviously it takes a lot of money. I don't know,$100 million to kind of like create a research center, to build a campus streaming lab, to fund them for five years. It does not have to be all my money. I can probably try to fundraise for it. But that would be amazing. Like if I could have my cake, I need it too. I have my sister close to me and my nephew's close to me and I could have a great research center in Lisbon.

1:30:19There's a wheelie. That is one of the things that you can do when you have money. Are you happy? Yes. Extremely happy right now. What makes you happy? this feeling of I'm doing the things that I want to at the level of quality that I want to with very few trade-offs. I think the set of trade-offs that I have right now are excellent trade-offs. I feel extremely happy doing the things that I do. I feel like I'm living my best life in a sense of like the people that I work with are awesome. My family is awesome. People are healthy. It's such a great time in my life right now. My parents are getting older, but they're getting to hang out with their grandchildren.

1:30:59And so we're in this perfect phase of like, things are going extremely well. And in fact, one of my anxieties right now, there's actually one of the things, it doesn't really break my happiness, but it is actually an anxiety. It's a stupid one. This is stupid. But I'm waiting for the other shoe to drop, if you know what I mean. Things can't get better. And so they can only get worse. It's sort of the current feeling. And so I'm sort of waiting, like this anxiety that I have about, which is stupid because now you're living in fear of something that hasn't happened yet. But this is a weird one, and I feel it.

1:31:29It's going to happen. It has to. It has to, yeah. Like, one of my mentors, he always told me, like, especially as you kind of grow older, there's more shit that happens. And you learn that it's almost impossible for everything at the same time to go well. Like, when something goes really well, like, then you're going to have another thing, parent or health or whatever that's going to go to shit. And then you have to kind of learn to accept that and deal with that. I mean, obviously I don't wish it to you, but... Yeah, no, but by the way, the family and the health ones are the ones that actually would be the things that reduce happiness.

1:32:07If a portfolio company or there's a problem or those things, I just expect them as part of my life. So those things don't detract from my happiness. They're just literally the thing that I want to do. Solve problems and like be part of these things. And so I don't see those things, bad things happening in a portfolio company as something that detracts from my happiness. Obviously, I wish that it didn't, but that doesn't really change my happiness levels. It would change my happiness levels as you've described. Health issues, you know, God forbid, you know, somebody passing away. Those things are going to be the hard things to face at some point.

1:32:35You told me the other day, I have a contrarian opinion on every topic. So let me throw a few topics so we can have some fun. I hope that I can step up to the plate.

1:32:50Contrarian take about the human brain. The human brain. Okay, let's see. Let's see. Well, I think artificial intelligence will actually be created in a different way that is not mimicking the human brain, actually. So adjacent. I think lots of us are thinking and lots of researchers are thinking that what they're trying to do is mimic the way that the brain is actually interconnected and all these different lobes and all these different prefrontal cortex and how these things actually operate. LLMs being one of the building blocks that they're connected. And I think we're going to be able to create intelligence that doesn't actually mimic the way that the brain is created.

1:33:28What's the result of that? The result of that is human-like interactions with something that just does not have the same traits that a human would have, if that makes sense. So kind of like extreme high, what we would call intelligence, but not necessarily with instincts of self-preservation or like all of this biological stuff that we've sort of like jargoned our way into having, but just like more of a pure intelligence entity that doesn't have a lot of the same characteristics that humans are just known to have. The contrarian take about relationships. Relationships. Okay, this is an interesting one.

1:34:11Let me think through this. We didn't prepare any of this. Just as a context, you told me that with your co-founder, you spent a lot of time doing that kind of exercises, right? Yeah, so in that one, it's a contrarian take maybe it's not as contrarian but one of the things that we did do is we all we both always defended the other side of the argument so whatever the debate is whatever we were discussing one of us would instinctively veer towards defending the other side of the argument by the way that's you're talking about your co-founder here not your wife right yes correct with my wife that would be extremely unproductive let's put it this way that would be extremely interesting and productive That would be.

1:34:54What does that mean? Do you give in a lot? No, no, no, no. But that relationship is obviously like, can't be like, that relationship can be as rational as a co-founder relationship. Co-founder relationship is, we're friends, but is to a large extent, a business relationship. And business relationships are based on rationality and different things than just a husband and wife relationship, which is based on a lot of different things. And being right is not one of them. Being right is seldom the important thing. But for my co-founder, this instinct of like, this has been interesting. I think actually as a self-discoverer has been really interesting.

1:35:31We've always defended different sides of the argument. And I've noticed that sometimes I started defending a side that I didn't believe in. And through my own arguments, I ended up changing my mind. And that has been a fascinating outcome of like this, like how, what way to actually put in my opinions. And I started having this instinctive notion of how hard is it for me to like change my mind on this topic. It's been a really interesting one. Yeah, I think that's a key trait of intelligence, actually. Being able to absorb, a lot of people will think, oh, no, if you're smart, like, or very intelligent, you need to understand everything directly.

1:36:07No, it's actually like, if I have more context, I can change my mind, actually, a lot. So there's two things. One is, I don't know, right? If you say, I don't know, actually, you can show that you're very intelligent or smart. And the other one is, hey, there is some new information here that I didn't take into account. I just changed my mind. That's it. So the interesting thing here though is that when somebody gives you a convincing argument, you can internalize you changing your mind at the moment. But what sometimes happened actually was I changed my own mind. I already had all the arguments because if I didn't, how could I make them?

1:36:45So I was actually in an active debate in the process of active debating constantly. made you surface arguments in a way that I don't know if what was happening was that you had received information and hadn't incorporated. And within the debate, you're incorporating this new information so your mind changes. Or if there's some other process by which your position was shaky, the other position was shaky, and then these new arguments are coming to light, are sort of like going through your brain and just start making more sense. And so you now have more affinity towards this argument. And it was just shaky to begin with.

1:37:16But I don't know. The interesting part for me was not, somebody gave me a very convincing argument and I just took that opinion. No, it's been like my own arguments that are in my head that I'm making end up changing my mind from one to the other, which is kind of an interesting one. So do you have a contrarian take about relationships? About relationships? I don't know if I have a contrarian take here. Actually, I'm probably pretty vanilla on that one. A contrarian take about entrepreneurship? Entrepreneurship. I do think that my contrarian take is, it really is at this point in 2025, the default path that everybody should take.

1:37:55And there's very little downside and there's very little risk. It is primarily upside. And I think it accelerates people's careers and people's progression. And especially when you're young, the younger you are, the more risk you can take. And so I do think that everybody should follow this path. What are you going to do with your kids? I'm definitely going to try to motivate them to, you know, be independent agents and like start things and follow their passion and their interests. So if they didn't start starting companies, that's great. I think the right thing for your children is to not have expectations and to just like allow them to like surface their own curiosity and then follow that.

1:38:29So I won't impose any worldview on them of like, oh, if you don't start a company or some kind of failure, no, it doesn't go to that. There's this like wishing and like realizing or thinking or believing that you, that there's little outside right now. And there's primarily upside and that has changed and is changing and where people are creating businesses but it hasn't fully like like it's not in the united states is a lot more obvious but even in other countries i think people haven't realized how much they can do with so little money and how they can create companies access the global market of the internet um and just build meaningful wealth for themselves their communities and their families with by taking risks.

1:39:07What do you think about crypto? Crypto. Well, I think DeFi will never work. Wow. That's so good. Okay. Unless DeFi founders have four-year cliffs and seven-year investing periods. Until we align the incentives of DeFi founders and tokens closer to what equity companies have, then we'll never have a successful ecosystem. Want to explain why? What's the current issue? Two, current issue is the obvious one, which is people get rich and they lose interest. If you have early liquidity for yourself and your team, and that was actually the outcome you were driving at, why would you actually work hard for the next six years and grind something that we just discussed is extremely, extremely, extremely hard.

1:39:49And it gets to the same outcome that you're already at. And so I think that has been very, very corrosive to the space. And I wished for a better outcome here. Obviously, look, as an investor now, it's very self-serving right um but also look i've never launched a token and encourage is not that type of company i had kane from uh synthetics and the infinex and so i mean it's pretty much what you're talking about synthetics they made a lot of money he even says it we understood the game etc right kind of build this on the ish thing and then you just cash out and you make a lot of money but then he had this thing where i need to come and like build this everything crypto app and how to do something that's actually useful for the space.

1:40:31That's amazing, but he's one in a hundred. Yeah, exactly. Like the other ones just do the whatever the beach thing is. And so this is extremely, extremely distracting. And also because it is this way, it just incentivizes more grifts. 100%. I mean, the problem in crypto is, yeah, that's a big problem. That's why I'm doing this here. I'm like, how do we, how do I help people look at the right thing? there's so much noise, right? And there is so many projects and shit. Like there's so much shit. I'm going to go and filter because I've been doing crypto stuff since eight years, probably late 2018.

1:41:10So seven years. So I'm not an OG, but I know who the OGs are, right? Like, hey, I mean, for me, ultimate goal, like Antonopoulos, Wences, Brian from Coinbase. These are, Fred, you know, these guys were like the, and there is a Polychain, Olaf, like, they're not really out there anymore, or some of them never really been. But like, you want to try at least to show the world, hey, look, these are the people that you should listen to and focus on. And because these are the real ones, right? Out of all the shit out there that you're just spending too much time putting your attention on. So absolutely, it's so weird, this industry.

1:41:52It just makes sense, you know. So since this internet has this major advantage, which is free and instant dissemination of information, and that's fantastic, but it's also terrible because you can disseminate any information out there for free. And so what's your biggest prediction for next 12 months? Predictions. This is an interesting one. I think that we're finally going to see the first real integrations between this world of traditional finance in the form of RWA's IndyFight. So a much better, we have played with things at the edges, but something that is actually a security or something that actually has utility value, but is traded and participates freely in the DeFi ecosystem, we've never had this.

1:42:42And I do think in the next 12 months, all the pieces are in place. All these people are racing at it. And so maybe that star says the first crypto on-chain IPO in the next 12 months. I think that would be a fantastic outcome. What does that look like? It looks like you do... I read about Coinbase saying, hey, we want to put the coin on-chain. The first on-chain IPO. First on-chain IPO. So there's an underwriting process. The token is issued on-chain. It has the actual same rough rights as a traditional security token would be, but it was fully an on-chain process. It didn't at no point got to get traded in the traditional exchanges and get like ran through the process through the traditional underwriters.

1:43:29I think that would be really cool. Amazing. Thank you so much for doing this, Yogo. Thank you for having me. That was a pretty mind-blowing conversation. So good. Thanks for having me.