Epicenter - Learn about Crypto, Blockchain, Ethereum, Bitcoin and Distributed Technologies - Dragonfly: The Secrets of a Top-Tier Crypto VC - Haseeb Qureshi

Episode Date: July 25, 2025

Founded in 2018, Dragonfly has quickly become one of the most prestigious crypto VCs. Dragonfly was one of the first to adopt a global approach to backing founders and disruptive tech, all while building a strong brand that allowed them to secure top-tier deals. Join us for a fascinating discussion with Haseeb Qureshi, managing partner at Dragonfly, to learn the secrets behind running a top-tier crypto VC and what made Dragonfly succeed where others have failed.Topics covered in this episode:Haseeb’s background, from poker to cryptoEffective altruismCrypto investmentDeveloping judgementThe vision behind DragonflyConsensus vs. non-consensus dealsKPIsPeople, Product & MarketsThoughts on the current crypto marketThe evolution of crypto VCsAdvice for crypto foundersThe importance of disciplineIs the golden era of crypto investing sunsetting?Episode links:Haseeb Qureshi on XDragonfly on XSponsors:Gnosis: Gnosis builds decentralized infrastructure for the Ethereum ecosystem, since 2015. This year marks the launch of Gnosis Pay— the world's first Decentralized Payment Network. Get started today at - gnosis.ioChorus One: one of the largest node operators worldwide, trusted by 175,000+ accounts across more than 60 networks, Chorus One combines institutional-grade security with the highest yields at - chorus.oneThis episode is hosted by Brian Fabian Crain.

Because venture capital, unlike trading, it's not a single-player game. Venture capital is a multiplayer game at its essence. You're usually on a team, and you win by helping people. And you only win if other people win. The other thing about it is that the feedback cycles are extremely slow. Right? So you make a VC investment, and you don't know for years whether or not you're right. It doesn't matter.

All that stuff is easy to learn. The hard thing, the thing that I can't teach you is judgment. But this ability to think very clearly to question obvious assumptions and to cut to the essence of something I don't know how you're training. It has to be that you have experience making tough decisions.

It can come from being a decision maker, building businesses, it can come from competitive computer games, I think can develop that ability to make decisions. You know, if you've just been in school for your entire life, I don't think that trains you very well

to make decisions. When you're in school, you're mostly being told what to do and performing tasks of memorization, you kind of have to build the reputation of the legend of yourself as an investor alongside it. And I said, look, I want us to be one of the most technical funds in crypto. When I'm competing with Olaf to win a deal, who does a founder pick? Do they pick me or do they pick Olaf?

There's two quadrants at which you can look at any investment. Consensus and non-consensus. Now, almost all the money in venture overwhelmingly gets made in non-consensus right. Hi and welcome to Episode at the Show, which talks about the technologies, projects and people driving decentralization in the Galactional Revolution. I'm Brian Crane. And today I'm speaking of Haseep Rureshi, who is the managing partner of Dragonfly, which is one of the best-known, largest crypto-V-C funds. So we're really excited to have Haseeb on today. So just before we go into it with Haseep, we want to share a few words from our sponsors this week.

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All you need is one GNO and some basic hardware. To learn more and start building on the open internet, head the NOSIS.I.O. NOSIS building the open internet one block in a time. So thanks so much for coming on, Haseep. I'm really excited. I was sort of diving a little bit into your story and your background. I think there's a lot of interesting things there. Maybe you can start there because, I mean, you started sort of your first, you know, real serious effort.

It seems like it was in poker. Like when you think of today, what are the biggest things you've learned from that time that, you know, kind of like still shape you today? Well, so I played poker professionally for when I was 16 years old until I turned 21. And, you know, when I was 19, I was ranked one of the top online, no limit holding players in the world. Poker is a very, it's a very unique game because there's nothing else that really teaches you how to think fluidly about risk and reward and about probabilities the way that poker does. It's in a way kind of surprising that we don't really have good ways to teach this.

to young people. Like I sort of still can't really even imagine if I, I don't have a kid, but if I did, I can't imagine how I would teach them how to think about risk the way that an investor does other than poker.

There's really just nothing like it when it comes to understanding the way in which you cannot be too risk-averse and you cannot be too emotional about making decisions. And a poker table is one of the rawest places

that will test your ability to actually make decisions under uncertainty and under emotional stress. So that part, I think, was really valuable training for what I would end up doing much later in my career.

As a program, I went through a lot of ups and downs and actually, at the end of my poker career, there was this big blow-up that happened. It was kind of a complicated story, but basically there was this guy who was cheating, and he was one of my mentees. He was a student that I was working with. And my reputation ended up getting caught up in this thing

because I was trying to defend him. And that led to me getting oustered from the poker community. And I was 21, I was very young. All of my, you know, I dropped out of school to play poker. It was all that I was doing with my life. And it really caused me to, to really rethink what I wanted to do with my life.

And what, you know, in a way, poker, it actually has a lot of similarities of crypto trading because poker is a very single player game. You know, you obviously, you're playing with multiple people at the table, but you're not on, there's no team poker. You play for yourself, and it's you against the world. And nobody really cares whether or not you do well.

And so you're going through your ups and downs alone. there's a saying in poker that always resonated with me, which is that everybody who understands doesn't care, and everybody who cares doesn't understand. Meaning, you know, in poker, you're always going through this volatility. You're always going through these swings or ups and downs, because there's a lot of luck in poker in the short run. In the long run, it's a game of skill.

In the short run, there's always ups and downs. And when you're going through those ups and downs, that's a lot of what makes it so psychologically challenging. and the people, you know, you think about your friends, your family, your mother, they don't really understand what it means when you tell them, oh, I just lost 100K today. They're like, oh, my God, you know, is everything okay? Like, should we worry about you, you know, should we call someone? And you're like, no, no, no, that's not what I need.

You know, I just kind of need you to understand that, like, I'm going through a tough time, but like, I'm going to be okay. And the people who really get it, who are other poker players, they don't care. They're just like, oh, man, you. You know, you're complaining. I'm like, I have my own problems. I'm going through my own downswain. You know, I'm not a shoulder for you to cry on.

And so you have to learn to be very emotionally and mentally resilient. I think it's very similar for a lot of traders is that, you know, if you're trading in crypto, you're on your own. You know, nobody's looking out for you. Nobody really cares if you lose money. And in some sense, like, the only way they can make money is if you lose money. So that, for me, it was really a. cauldron, I think, that forged a lot of my, my own determination and my own resilience.

I think it was a very, very difficult time after I quit poker because I really didn't know what I wanted to do with my life. And I was really questioning myself as, you know, was I somebody who actually could do something valuable in the world? You know, poker is a, in a way, again, very similar to crypto trading. It's a, it's a kind of, I don't want to say nihilistic, but it's a very selfish activity at the end of the day. You know, like I always reflect on the fact that as a poker player,

you know, it's a fascinating game. It has all this mathematical complexity and really beauty to it as a game. But in the raw reality of it, no matter how good I am, the reality is like, you know, the way I make my money is some guy sits at a table

who's a, you know, a dentist or a doctor, you know, who did something actually useful for someone in the world and they come sit at a poker table and they lose money to me. And when you really, think about like, okay, that's where I make my money from at the end of the day. You know, I can glamorize it about, you know, the intellectual contest of, you know, this game

of risk that I'm playing into other people. But the reality is like, yeah, I got really good at a card game. And that always really bothered me. And so it made me determined after I quit poker that I wanted to do something more valuable with my life. And that's what ended up leading me into the tech industry and eventually, you know, coming into crypto. So, yeah, I mean, I guess one of the really unique things about, because you mentioned

the analogy to investing. And maybe with trading, it is a bit, you have to have fast feedback, right? But I guess the thing that's incredible about poker is just the immediacy and the amount of hands you can play and the amount of feedback you get. So I guess that's really hard to replicate anywhere else. Yeah, trading is the most similar.

Ironically, VC is actually quite different from poker. And it's one of the reasons why a lot of poker players find their way into trading. Very few poker players find their way into venture capital. Because venture capital, unlike trading, it's not a single player game. Venture capital is a multi-player game at its essence, right? You're usually on a team, and you win by helping people. You win by finding a founder, finding somebody who's building something, and helping them to get there.

And you only win if other people win, right? You cannot win in VC on your own, like, obviously, by definition. So it's intrinsically pro-social in a way that both trading and poker are not. the other thing about it is that the feedback cycles are extremely slow right so you make a VC investment and you don't know for years whether or not you're right and you get some signals early on it's like oh you know this person raised more money or they you know they're getting some momentum and they got some Twitter followers but you know being in crypto you know that's that's no guarantor of success and if anything it you know sometimes it's an anti-pattern if a project is

getting all this hype really early kind of you know sort of sort of it's sort of gasses out very quickly if it leans too much into just purely building hype. And so the reality is it takes years before you actually get the full feedback loop, which means it requires a very different kind of thinking and a very different kind of of a mental adjustment than a game like poker or a game like trading where you get instant feedback, right? If you enter into a trade, especially if you're a short-term trader, you know very quickly whether or not you made the right decision. And the same thing is true in poker, although there's uncertainty and there's some randomness and that's also true in

But directionally, you're getting this reward signal that's pushing you in the right direction. In venture, it requires a lot more using a lot more fluid intelligence to understand it. Did I make the right call last week, last month, last year? And a lot of times the answer is that you really don't know, and people who look like they made great decisions in one vintage, in retrospect,

it's like, actually, that was an absolutely terrible vintage. And the people who sat out from this particular trend, whether it's, you know, Metaverse investing or whether it's, you know, NFT issuers or whatever, for a year or two, those people can look brilliant. And then, you know, two, three years later,

all of a sudden, the evaluation of who did well and who did poorly completely changes. And that's happened in crypto so many times that it's really, in a way, quite fundamental to the way that VC works. Yeah, I definitely want to get into that a lot more. I'm curious, so you said, you had this phase of being kind of lost

and then you end of tech industry. I read, so you're also into effective altruism, right? So were this kind of connected? Very much connected. So when I was young, I made a lot of money at a young age as a poker player.

I was surrounded by a lot of people who had made a lot of money very young. And the thing that I noticed pretty quickly, I think sooner than a lot of people get to learn this lesson is that money doesn't make people happy. And if you're in the poker world, it's obvious because you see all these people

who are making all this money, and they're miserable. You know, and you realize, like, okay, I know all these people who are like, you know, my classmates who I was going to uni with who they don't have a lot of money. And most of them are actually pretty happy, even though they're, you know, scraping by, they don't have a lot of cash,

but they're having a great time. And people in poker world who are like, you know, sitting down, hunched at a casino, you know, they're staying up late, they're working on hours, they're just kind of, they're miserable. You know, not all of them, obviously, but many of them. And they very quickly broke this connection in my head

between money and happiness. And I realized pretty quickly that I was not somebody who's very motivated by money. They don't spend a lot of money. I don't really have a lot of need for flashy things. But I realized coming across the philosophy of effective altruism, this was around like 2012, 2013 that I first came into time.

of these ideas. It incredibly strongly resonated with me that, okay, money might not matter very much to me, and I don't think money is going to make me happy, but money has tremendous power in the world, and that the effect of that money is very, very asymmetrical, right? That money can do a lot more good in a developing country than it's going to do for somebody like me who lose in America and like, okay, well, I can have a nicer TV, I can have a nicer car, but it's not really going to change my quality of life in a substantial way.

But a relatively small amount of money, just a few thousand dollars, can be literally life-saving in another part of the world. And that was what ended up getting me on the train of thinking, hey, one thing I know that I'm good at is making money. I was able to do it very well as a poker player, and I bet I could do it again.

And so if I go into a field that's lucrative, and is something that I'm also driven towards and excited about and care about like technology, I think I can donate a lot of that money and have a lot of impact, a lot more impact than I could just have on myself personally. And that was what made me decide

that when I came into the tech industry, I was going to donate a third of my income to high-impact charities. So I decided that in like 2013, and 2015 is when I first came into the tech industry, and ever since then, I've been donating a third of my pre-tax income. Now, the funny thing, of course,

in crypto, you can't, talk about effective altruism without talking about SBF. Because, of course, the most famous, the most famous effective altruists in the world was SBF. And it's funny because I actually met SBF. The first time I met SBF was in 2014 before he was in crypto. He was still at Jane Street at that time. And I met him at an effective altruist summit in San Francisco. So he was, you know, just a scrawny little trader, you know, had the crazy hair, wearing the shorts.

and I think I met him in a hallway at one point. I recognized him because he was somebody who was himself a very active donor in the effective altruism space and I was an aspiring donor. I didn't have any money yet. So I was like, I hope to someday have money, but right now I'm pretty broke.

But I met him, and the next time that I would meet him would be many years later in Berkeley when he had started Alameda research. It's funny because effective altruism as a philosophy went through such, you know, it's like crypto, right? It went through such a massive upswing and reputation

and then absolutely cratered with the collapse of FTCS. And it was very unfortunate that the industry ended up putting all their eggs, or not the industry, the movement ended up putting so many of their eggs into the basket of this one man. Because at the end of the day, there are a lot of people who are effective altruists. You know, it's a movement that probably spans, you know, 50, 60, maybe even 100,000 people. And most people are not that loud about it.

You know, they just kind of do it. They don't make their whole identity around it. You know, like, I'm an effective altruism been doing this many years. I don't tweet about it all the time. I don't try to make a big dog and pony show when I make my donations at the end of the year. But the, you know, the essence of effective altruism

is really quite simple, which is just this idea that, you know, you think you're giving, your money can have a lot more impact if you think about it in a more rigorous way. SBF was in many ways the worst element. It's like a good example of what happens

when you take anything to an extreme, right? Any philosophy can be taken to an extreme. And at those extremes is when you start really untethering from normal common sense morality. If you start being convinced that, hey, you know, effective altruism is so important, I shouldn't take care of my friends and family.

or I should give away everything that I own and kind of live as this weird ascetic. Or, you know, I should steal people's money in an exchange in order to donate more to charity. Right? Like, when you start really getting off the deep end, you get into extremism. And there's, you know, there's religious extremists,

there's philosophical extremists, and SPF sort of now serves as this cautionary tale to everybody in the effect of altruism world of like, hey, you know, everything, Everything should really be in moderation and includes effective altruism. So anyway, I thought I would just give that thought. I don't know if you want to dwell on the effect of altruism connection. It's okay, I think.

Yeah, yeah, yeah, fair enough. Let's talk about crypto investing. So you got into that through Metastable, which probably not a lot of people know today, but it was one of the first crypto funds. probably one of the first, certainly more like hedge fund like structure, if I remember correctly. What was it like working there?

And what were sort of your biggest learnings from that? So I came into Metastable. Actually, before I came to Metastable, I was working at Airbnb, came into crypto full-time, worked at a company called 21, which became aern.com.

That's Bologi's startup. They got a corporate by Coinbase. I left and then started my own startup. And that was when I ended up meeting Naval. So, Naval, of course, founder of Angel List, very well-known angel investor, influencer, life guru, Silicon Valley.

And he ended up convincing me to shelve my startup and join Metastable as a GP. So Metastable is one of the very first funds in crypto. I didn't know anything about investing at the time that Naval recruited me. Like literally my own portfolio, I just had in index funds. I don't think I'd ever made really a serious stock investment.

Like even stock picking is something I just didn't do. It was just like, no, just index invested. I read all these papers that nobody can beat the market. So just do passive investing. And Naval was like, hey, you should become VC. And I was like, go VC. I don't know anything at all about, you know, finance. I don't know what a term sheet is.

I don't know what carry is. I literally didn't know anything. And Naval was like, look, it doesn't matter. Like, all that stuff is easy to learn. the hard thing, the thing that I can't teach you is judgment. But if you have judgment, the rest of it is, you know,

you're a smart guy, it's pretty mechanical. I can teach you the rest in just a few months. And that, you know, in the beginning, when I first came into Medistable, I really thought this is going to be temporary. You know, I'm going to come into Metastable, I'm going to kind of hang out, learn a few things.

But then, of course, I'm going to go back in the startup world. I'm going to go build something because I saw myself as a builder, but also, you know, psychologically, I just thought, like, well, building is obviously the real thing. You know, VC is like this kind of, you know, whatever, sort of, you know, bullshit job that you do in the interim

of, like, early retirement or something. You know, it's like a waiting room before you have a good idea. And over time, I came to appreciate more and more that venture was actually something very, very interesting and unique in its own right compared to what I was doing before. And the way that Naval described it is something that's still resonant. with me, which is, you know, if you're building a startup, you know, you imagine crypto is like this wave that's coming to shore. And we know the wave is going to hit and it's going to transform

the beach. And if you're a startup, you are like one grain of sand in that wave trying to make your way to shore. And you might make it, you might not. And like, it's you against the world. And, you know, it's like, okay, this is the, this is the titanic conflict that every startup founder feels like they're in. But to be an investor is to pull up a chair at the side of the beach and to take bets on which grains of sand are going to make it short. And in a way, okay, maybe there's some element of diversification you get as an investor, but the more important thing is that it's actually really the best seat in the house to watch

the wave come in. Because there's no better place that you're going to really get to see what actually happens to the world. and to be able to test your intellectual ability to predict how it's going to play out. You know, I came into crypto in 2017 full time. And at that time, you know, people were talking about the ICO boom and, you know, the way in which, you know,

IoT was going to get transformed and all, you know. It's funny because one of the very first podcasts I was listening to is actually this one, Epicenter, because there wasn't a lot of technical content back in 2017. And, you know, listening to the show, I used very studiously would listen and try to understand like, oh, you know, what's, what does Iota do? What does foam do?

You know, all these projects from that era, you know, you dutifully listen and understand and really try to predict, is this the future or is this a mirage, right? Is this wave going to make it sure? As an investor, that's fundamentally your job, right? And there's a lot of other stuff that goes into it, about sourcing and, you know, building relations with founders and helping them out. But this is the core of what investors do. and to be better at that,

at being better able to predict where the future is going and how technology will evolve, I've come to appreciate is the most interesting thing to me of anything that I can do. Building is fun, it's very satisfying to feel your thing

turning into a real product out in the world that people use. And the way, building an investment firm is similar in many ways. Having built Dragonfly, we're like 45 people around the world. We're a big brand. We do a lot of, we do a lot of things that any company has to do in order to establish itself and to build a strong reputation. But the end of the day, investing is

really about predicting the future. And to me, there's no, there's nothing that quite resonates as much with me anymore as getting to do that for a living. So you mentioned the judgment thing as this, you know, crucial thing an investor has to be good. And do you think this is something you just had? Did you learn it in some way? Is it something that you, you know, you do you try to develop it and like how? I don't have a good answer to that. Like honestly, when I look, because we obviously hire a lot of investors and we interview a lot of investors and I'm now on the reverse side of the table.

I'm where Naval once was when he was looking at me and how to determine does this person have judgment, right? Obviously when people come in and they're junior, they don't know that much about investing. They don't know that much about VC. You know, we'll often ask them a case study of like, hey, you know, would you make this investment, write me a memo about why you would or wouldn't make this investment. And you read this memo and some of them are very polished. You can tell, okay, they've thought a lot about investing before. Some of them are very unpolished. But most of the time, you can really kind of see through

does this person have that spark of insight, that they can think for themselves, they can think very clearly, they can cut through to the center of the problem. And it's sort of like, do you get there in one cut, or do you slowly kind of trim around the edges and maybe eventually you'll get there? and that question, when you see it, you know it instantly, that okay, this person has good judgment. And is it, it's not always connected to the fact that they've been an investor before. A lot of people who are very good at this and can think very clearly and lucidly about making good investment decisions don't have training as professional investors. but this ability to think very clearly to question obvious assumptions

and to like cut to the essence of something I don't know where it comes from I don't know how you train it it has to be like almost certainly when I think about it it has to be that you have experience making tough decisions

and where would you get that kind of experience I think it can come from many different places it can come from being a decision maker building businesses it can come from games I think games are one of these places that do actually if you're a if you're competing at a high level in games.

I think you can even be true for, not things like poker, but even just competitive computer games, I think can develop that ability to make decisions repeatedly very well. But most people who are, if you've just been in school for your entire life, I don't think that trains you very well to make decisions.

I don't think you're making a lot of decisions when you're at school. I think when you're in school, you're mostly being told what to do and performing tasks of memorization and largely conformity, which is can you go home and do the thing I ask you to every single night

and memorize this stuff. But the reality is that, being able to memorize things is totally useless in investing. There's nothing you need to memorize investing. On some level, you need to have a general background knowledge

about the world and about, okay, I need to think about how big of a problem is this that's worth addressing. But very little memorization is involved. Very little of what you learn in school is going to be applicable to something like investing in crypto. It's mostly your ability to teach yourself,

to think fluidly about new domains, to really be able to, again, make difficult decisions that nobody else is going to explain to you how to make. The more that you've done that, the better you're going to be at this. And that's one thing that I think for poker, you know, for poker, it's not just that when I was playing poker, I was making tough decisions at a poker table. it was also that the era in which I started playing poker,

and to be clear, I think poker is actually very different today than it was at the time that I was playing it. Poker was not very developed as a game when I first came into playing poker, meaning that today you have these game theory optimal strategies that are very well worked out. People do studying alongside these solvers, which are these programs that will basically output

the game theoretic optimal Nash equilibrium for a given poker situation. And most of what people are doing, doing is they're studying what the computer is telling them. The computer knows the answer. It's like chess, right? Poker has become much more like chess in the last 10 years. Poker was not at all like that when I came into the game. Poker was still in the process of being developed as a fully fledged game. And as a result, a lot of what we were doing, like what I see us, like me and my peers in that generation, was much more like science. it was much more us trying new things, developing different parts of the poker meta,

and really challenging a lot of the assumptions of the poker players who came before us. It was actually, like, when I look back of what I loved the most about poker, it was that. It was us kind of opening these new frontiers and experimenting with new strategies that nobody had really tried before and proving that they could work in different ways.

That skill, most people don't have. if you went to school, you've never done anything like that in your life, unless you, you know, at a postgraduate level, you're a researcher or something like this. That skill is the skill that I think most translates into being able to be a good investor. Because being able to be a good investor means, okay, the year is 2021, Play to Earn was just invented. What the fuck is Play to Earn? How does it work? Where is it going to end up?

Right. There's no book you can read. There's no, there's no expert that you can consult. There's no amount of learning you've done in your life. life that we prepare you to answer that question. You have to think for yourself from first principles where you think it's going to go and you have to make a bet on it. Yeah. Yeah. Do you think your ability that this kind of judgment is developing much today in what way is evolving? It's a good question. I think my, I would say that my ability to make decisions within

investing is getting better. As I get more data, as I have more experiences, as I make more mistakes, and as I have more successes, I'm learning from all of these things, you know, patterns and behaviors that I'm realizing are more and more important, right? So just to give you one example right now, I have a portfolio company that's going through a co-founder breakup. So, you know, two people started a company together. They were very good friends. Now they're splitting apart, they hate each other. And navigating a co-founder breakup is one of these things that the first time you do it as a VC, you just have no idea what you're doing. It's like, it's like a divorce, you know, and you're like the friend of both of them and you have to somehow safeguard, you know,

what's going to happen to the kids and what's going to happen to all the stuff, but also, okay, these two people who I also care about and I want to make sure that they're going to do okay. It's better for everyone if they do okay. You have to navigate that. And it's almost like being a mediator, but then also being an investor and also being, you know, you do a lot of different things at the same time. First time I did it,

no idea it was, you know, it was just totally, totally unprepared to deal with that. Now I've done it many times. And the end of the time you do it, the better, more solid, more capable,

more fluid you become at being able to help people navigate those difficult things in a, in a startup. Same thing with dealing with M&A or dealing with some kind of strategic pivot or, you know, helping a company,

you know, figuring out its hiring strategy. The first time you, you do it, you sort of stumble along. You know, when I was at MetaSable, the funny thing about Medistable is because, you know, Naval, you know, he's such a well-known person, he was so famous, obviously still is, but, you know, at that time he was very, very active in the crypto investing market. Everybody wanted his money.

And so when I was at Medistable, you know, even by the time that I left, I had never actually won a deal. When we wanted to make an investment, so it was like, okay, you know, so at MediSable, we did the C-Dround of Avalanche. And I was like, hey, I think we should do this. I think Goon is great. Let's do the seed round. I knew Goon and I had a relationship with him.

But at the end of the day, he didn't want my money. He wanted Naval's money. And so Naval was the one who went out to say, okay, Naval, we want this much allocation. He would go and he would go win the deal. And it was at Dragonfly that I had my first ever actually, okay, Haseeb, it's your job to win the deal. You have to convince the founder to take your money.

And why would you take my money over A6 and Z's money or Paradigms money or Polychains money or anybody else's money. And it's intrinsically like a very, you sort of have to be, this goes against a lot of your instincts. If you're somebody like me to say like, hey, I'm amazing. You should work with me because I'm a special guy. And like I'm exactly the person you should work with over everybody else. Everybody else sucks. And I'm the one who's going to solve all your problems. You have to do that. You have to sell. you have to fundamentally convince the founder that you are special

compared to everybody else and you will solve their problems in a unique way that nobody else will. And that skill is a skill that you can only get better at the practice. You know, so the judgment thing itself, I think at the end of the day,

I don't actually know that my judgment, you know, at a core level, has really gotten that much better over the time that I've been at Dragon Fly. I think my judgment as an investor has gotten better in the same way, you know, as a poker player,

I got better and better over the years at playing poker. But would my judgment translate? I don't know. I think that the one thing I have noticed to myself since I became a VC, before this, I was a software engineer,

I was a builder, I was of course a poker player. I only ever played, again, largely single player games. So, you know, when you're a poker player, you're playing for yourself, you know, you don't really need to be a social butterfly to play poker.

And of course, being a, you know, If you're a software engineer, it's like the most quintessentially antisocial job is writing code. But VC is hypersocial. You know, all you do all day is talk to people. And when I first started, it was exhausting for me. It was very, very difficult because I was psychologically and mentally quintessentially a builder. And now that has really changed kind of who I am.

And it's something that all my friends and my family, they can't help but notice is the way in which, becoming a VC really changed me. And I think in that respect, it's very good for me because when I first started, I could not handle a day full of meetings. Like literally, I would collapse at the end of the day.

I'd be like, I have to cancel. I cannot do another meeting. Like, I'm so exhausted talking to people. I just want to, like, read and, you know, go read a white paper. You know,

like that just sounds so nice to me compared to having another fucking meeting. But leading a firm, building a team. And on some level, you know, part of what you have to do as a VC is to build your own brand very intentionally. Because, you know, at the end of the day, VC is a people business.

You know, on some level, yeah, okay, Dragonfly is a brand and people care about Dragonfly now. And, okay, it's kind of cool if Dragonfly is your lead. But at the end of the day, funds don't really have independent brands of the people. Right? Like, if I bounce from Dragonfly and, like, everybody leaves and we turn over and there's a new team of Dragonfly, you know, it's not like Airbnb. You know, if Brian Chesky leaves Airbnb, nobody really cares, you know, you'll still use a product. I don't think anybody would even be like, oh, I don't know if I can use Airbnb anymore now the CEO has changed. But at a VC fund, it kind of is, right?

The VC fund doesn't really mean anything without the people there. And so at the end of the day, you kind of have to build the reputation of the legend of yourself as an investor alongside it. And that was something that would have been very difficult for me four or five years ago. And it's something I've gotten a lot better at. So when you started Dragonfly, what was the kind of company you wanted to build and how did you want it to be different from the other crypto funds? So that was actually very central to my decision to join Dragonfly. So I actually joined Dragonfly about like six months after they first started. So I wasn't there at the very, very beginning.

The fund wasn't, it was like half raised at the time that I joined Dragonfly. So I just left Metastable and I was kind of, a free agent deciding what I wanted to do. And funny enough, I was actually working on a course. So back when, Abology, after he left Coinbase, he started this thing called Nakamoto, which was this publishing thing. I don't know if you remember this.

But I created this course of blockchain 101. And I was working on this, and I thought I was going to write a book teaching blockchain. So long ago, you know, in a way. This is also when educational materials in crypto were much worse than they are today. So thankfully, that gap has largely been made up. But at the time, there was really only

podcasts and one textbook, which was the Princeton textbook, which, you know, that's how I learned about Cryptel was reading the Princeton textbook. And so I was, that's what I was doing at the time.

And, you know, Bo ended up approaching me and trying to convince you to join Dragonfly. In Dragonfly at the time, they didn't really have much of a brand. I don't think anybody knew them

in the West. You know, they were kind of this, they'd invested in other funds. They'd invested into, you know, polychain and paradigm and a bunch of other funds. And they did some deals like kind of follow-on investments alongside some of their other managers that they were backing.

But they weren't really doing direct deals, investing directly into companies. And they weren't leading any deals. And so, you know, Bo pitched me on this vision of building a global fund. And when I say global funds, you know, at that time, I had never actually been to East Asia. Never been to Japan, never been to China, never been to Korea, never been to Singapore. This was back in like 2017, 2018. And I knew that crypto was big in Asia,

but I kind of knew it intellectually. It was sort of like, well, now that I know this, I can make decisions on that basis, but I don't really need to go there. I don't need to meet a miner. I know mining exists, but what does it really matter, the details of what they do? And Beau was the one who convinced me that,

no, no, no, no. If you want to understand what's really happening in crypto, if you want to understand this global phenomenon, you have to be able to see the whole elephant. If you haven't seen it with your own eyes, you don't really get it. And all the VCs in crypto at that time were almost to the last man based in Silicon Valley.

Certainly in 28, you know, before COVID, everything was in Silicon Valley. And it was out of Silicon Valley that people were investing in this thing that's happening all around the world, right? And I was very much that. I was, you know, I met a stable. we were in San Francisco.

We never invested in anything that didn't come to SF to meet us. And Beau's vision was very different and it really resonated with me. They're like, hey, actually, why is no one doing it this way? Why is nobody opening the aperture and looking at the whole totality

of what's happening in crypto globally? And what would it look like to build a firm with that being the initial animating hypothesis that actually, if you could see the whole thing, you would do it somewhat differently. That was the pitch that he made to me.

And I told them, like, look, I'm potentially down to join, but I have some demands. And if you meet those demands, I'll join. The first demand is that, so at the time, Dragonfly was not a technical team. There was nobody technical on the team. And I said, look, I want us to be one of the most technical funds in crypto. That's what Medistible was.

Medistable was led by Lucas Ryan, who was, you know, he studied cryptography at Stanford under Damona. and the way that he taught me how to invest and how to diligence stuff was you know you go into the GitHub like you actually understand from a protocol level what they're doing what the attack surfaces

how robust is this technology like if you can't run it yourself you don't understand it and that that kind of technical approach to diligence like really nobody in CryptoVC was doing at that time this is before A66NZ Crypto

before paradigm you know most of these teams were run by people who weren't technical in the in the in the VC world and so that was the first thing is that i want us to build a technical team i want us to know i want us to be known for being technical second is that uh we got to start leading deals i want us to be actually competing with the poly chains of the world with the pantaras with with the a 16 zs um and third is uh we're no longer going to invest in funds everything that we do from now on is going to be direct we're going to work directly with founders and we're going to be known as being one of the premier funds in crypto.

And Bo said, I'm down. And that was how I ended up coming into Dragonfly. So that was the original thesis of the kind of firm we wanted to build. And now at the time, we didn't have a lot of resources, you know, and again, we were flanked by the Polychains and the Pantera's and the A16s who were much bigger, much better resource. I mean, at that time, those guys were huge. You know, my goal originally when we first started Dragonfly was to someday beat Polychianzies. Now, today, that might seem really bizarre of like, why PolyChate in particular? It's like, no, no, no, you don't understand.

Polychain at that time, they were the number one fund. They were the only people who had a billion dollars of AUM. They had it backed almost everything from the first generation of crypto. You know, whether it's MakerDAO, PocaDot, they were in Avalent. There were so many things. Cosmos early. They had so many wins. And, you know, looking at Polychain, I was like someday,

someday we're not there yet it took a long time for us to climb that matter but someday we're going to beat polychain and uh in terms of getting into deals or in terms of the- Yes, exactly.

As a VC, the way that you think about like what's the actual head-to-head is when I'm competing with Olaf to win a deal, who does the founder pick? Do they pick me or do they pick Olaf? The end of the day, that's the head-to-head.

You know, it's kind of like in poker, we call it playing heads-up, which is one-on-one. if you want to ask who's the better player which fund is winning on some level it's like okay did you make better investment decisions

obviously that matters but it's hard to quantify that it's hard to tell because like I said all this stuff takes years to play out but the one thing that you can know as a platform as a brand is my fund winning

at the end of the day the number one determinant of who ends up getting the better returns is who can get the better deal who can win and the way that you you know, there's one way to think about investing is that there's

two quadrants at which you can look at any investment. Okay. Those two quadrants are consensus and non-consensus, meaning that everyone agrees this guy's going to be the winner and, or maybe you see something other people don't. Right? So an example of a consensus deal would be something like, you know, take OpenC. Right? To the OpenC Series A

was an incredibly competitive round. right this was like in i don't know what was this like early 2021 open sea was growing like crazy everybody knew open sea was going to be the winner and everybody was competing to try to win that deal everyone gave them a term sheet every single VC you've heard of um or take for example um you know the mega eth series a incredibly competitive round everybody was giving term sheets to to mega eat at that time and um these are consensus deal now there's non consensus deals as well so non-concesses deal would be like the salana seed round right salana seed round was not competitive, right? Salana pitched everybody. Multicoin won it, but they didn't like win it because

everybody, you know, they beat all these other people. They won it because everyone else said no. And so, okay, multi-coin wanted. Same thing with Salana Series A. Everybody, they pitched everyone. Everyone said no, except for multi-coin. And so you have these consensus deals, not consensus deals, and there's consensus right, and consensus wrong, right? So there are times when everybody is, everybody has consensus on a deal, and the deal is correct, right? It is the winner. Everyone knows it's going to be the winner.

And then there are times where the consensus is wrong. Now, almost all the money in venture overwhelmingly gets made in non-consensus right. That's where you get the 100-Xs, the 150-Xs, the 500-Xs, right? And everybody knows ventures

a power law business, and that means that the really, really big outcomes are the ones where you make the lion's share of the returns. but a lot of money also gets made in consensus right. And then there's consensus wrong where you're going to lose money and then non-concessus is wrong.

That's where you're making crazy bets out there that don't pay off. So non-consensus right is where your brand doesn't matter. You don't need to have a great brand or to do non-concessus right deals. And in a way, if you think about early one confirmation or early multi-coin, they didn't have the best brand of crypto, but they were able to win. these non-concessus deals, and they eventually able to parlay that into building a great brand.

But consensus right deals are consistent money makers. Right, that's where a lot of the money adventure gets made. It's not where the really incredible outcomes generally happen, but it's places where you'll consistently make good money. And that is purely a game of brand.

If it's consensus right, everybody knows. You know, the classic examples of Google Series A. Everybody knew Google was going to win, but only Sequoia got to play, right? because Sequoia is Sequoia. They had the brand to be able to win that deal. So that's where brand matters. And that's why it's very important to cultivate that,

that ability to win head to head against another VC. If you look at our biggest wins, you know, one example of this is the Athena seed round. So we led the Athena seed round. That was non-consensus. Now, why do I say it's non-consensus? One, it wasn't a super competitive round. Second, it was after terror collapsed.

Right? We led the Athena Seed round after Terra collapse, after people thought DFI was uninvestable. And especially people thought that an algorithmic stable coin was completely uninvestable after the collapse of Terra. It was our ability to identify that, hey, no, no, no, no. What's happening with Athena is different from Terra, right? We never invested in Terra.

We passed every single round of Terra because we understood that the mechanics of Terra were fundamentally insecure. They're fundamentally something that as it went to scale, it was going to break with probability one. but something like Athena no Athena is a cash and carry trade Cash and Carrey trade has been around forever this is the oldest thing in history

I was talking to hedge funds that were pitching the cash and carry trade back when Dragon Fifer started it's a very well understood financial product it's not like oh this is a bank that takes on more and more leverage the bigger it gets right that's what Terra fundamentally was so understanding that

and being able to see through to the future is how a lot of the returns of venture get made. But the measurement of winning is how most of the bread and butter of venture works. And so that was when I say that I wanted to beat Polly Chain, that's what I mean. Eventually, you beat them in returns. But the first thing, the first thing that you see as you become a better fund is eclipsing them in terms of being able to win in the head-to-head. But you still think like most of the returns, if you think of like Dragonflies, track record, was more in this non-consensus right bucket

or to what extent was the consensus right also a driver for this? It's usually something like 70-30 is that 70% of your returns come from a very small number of non-consensus deals and then 30% of your returns which is still substantial

comes from your consensus deals. And most of the time, it's not always true, right? So it's not literally true that Athena had no other bids when we won that deal. but it was not the juggernaut. It was not perceived as the juggernaut that it is today, right? It wasn't every single VC,

every single neighbor at VC bidding on that deal. But there are a lot of times that, like, the big winner can end up continuing to win and win and win and win and win. You know, one example of that is something like hyperliquid, right? So we were one of the VCs that was trying to get Jeff to take a VC check. You know, and we were, this is relatively early before their air drop, obviously.

we were, you know, we'd built a relationship with him and we were really trying to win that deal. We weren't winning it against other VCs. Like, there was no round. It was us preempting and trying to get him to take our check because we thought what he was building was really different and really compelling. And ultimately, you know, he got close,

but he said no, that I don't want to take any VC money. And, you know, there were other firms, other top tier firms that you know that were trying to do the same thing later of trying to stuff him with a term sheet, trying to give him a bunch of cash, and say, hey, you know, let's do something even though you're not looking for money.

Your ability to do that is ultimately constrained by how strong your brand is, but at the end of the day, you're never going to win all of them no matter how good your brand is. There's always some hyperliquids out there that will just say no to everyone. And no matter how good your brand is, even if you're, you know, A60 Crypto or Paradigm

or Sequoia or whoever, you're always going to lose deals. And so the question is, you know, as a fund, do you have that feedback loop of, okay, we lost this deal. Why do we lose the deal? Do we actually understand why we lost? And is this a problem that we can learn from and get better at? So the next time we go at this, we're going to do better, right? If you have that mindset like a product founder that you're constantly thinking about how to iterate in the direction of getting better, then, you know, with near certainty, you will improve as a firm. The weird thing in venture is that, you know, one thing I realize, part of the reason why we've been

so successful in venture. I think a few reasons. One is that we're just, really persistent and a lot of people just kind of gave up when crypto went through downturns or when things went badly they just you know they just didn't have the resilience to keep going um that's the honestly the most common thing that i've seen from all the vCs that i remember from when i first came in the industry most of them aren't here anymore most of them just bailed um so so that that is almost obvious thing is just do you have the stomach to be able to handle an industry that's as chaotic and as cyclical as crypto uh but the second thing is like why did you get into venture a lot of people came into venture because they think that venture is this, you know,

genteel job that you can just do on, you know, in the summers and you take the summers off and you know, you work like nine to five and then, you know, it's like, it's like ultimately a kind of early retirement for people. Like that's how they see it. They see it is this like high status job that you get invited to a lot of cocktail parties and you have to pontificate on Twitter. And that's not how I see it. You know, like that's not why I got in the space. I gave me the space to win. And I come in the space to win. And I come in the space to win. And to me, that means that every single day you're getting better. Every time you lose a deal, you obsess over why you lost.

Every time you don't see a deal, you try to go understand why didn't I see this? Why didn't this founder come and talk to me? And if you don't have that mindset, you're just going to lose. You're just going to keep losing and losing and losing and not learning why you're losing. And so that feedback with that iteration cycle that founders have of getting better every single time, every single day, every single moment you get product feedback. How can we get better? How can we get better? that loop I learned with enough time that a lot of VCs don't do it

and they just do just keep sucking as VCs and not ever really committing themselves to intentionally gain better and that's why as a firm I've been continually surprised at how quickly we've latched so many other VCs have been doing this much longer than us so you mentioned the ability to get into deals obviously there is ultimate returns

of the fund, are there other sort of dimensions by which you judge the success of Dragon Fy? I mean, those are, there's ultimately three dimensions that you care about as success as a firm.

So the first and foremost is returns. Returns at the end of the day is the North Star. The second is Brandt, right? Your ability to actually win deals when you're up and head-to-head against another firm. The third is ability to raise money.

Because at the end of the day, you know, VC is a scale business. So if you, you cannot actually raise the capital you need to go deploy your strategy, then it doesn't really matter how good you are, right? Because you don't have the money to actually go put all this stuff into motion. So you learn as a VC is that you kind of have two different audiences. What audience is the founders and just kind of the crypto community, how they perceive you and how they understand what you're doing, and how they perceive your brand. The second is actually

among LPs, which are a totally different world. They don't read crypto-Twitter, they don't care how many retweets your stuff has gotten. To them, your brand is constructed by this totally different channel and style of communication, which is to institutional investors or to family offices or whoever it is that you're raising your capital from. How do they perceive you? What content do you create for them? What are the things that you've done in this world that contribute to your brand?

And they care a lot more about things that nobody in crypto. the Twitter cares about. When I was reading through your blog, one of the things you linked to was this post by Mark and recent, where he talks about, you know, people, product, and market as sort of, you know, three dimensions by which you can evaluate a startup. And, you know, he comes like, hey,

the most important is market, right? If you don't choose the right market, like the rest kind of doesn't matter. I'm curious. Like if you, let's say you left being a VC and you had to start a company in crypto, what would be, I don't know, one or two, maybe three markets that you would focus on? That's a great question. I definitely can't name me three. I think, so probably if I were to try to build something,

I would be spending a lot of time at the intersection of crypto and AI. I think probably the thing that I would want to build is to work on AI-powered wallet automation. AI-powered?

I think this is the kind of wallet automation. Okay. So, you know, how can I get my wallet to be much more intelligent than it is today? And the reality is, like, we depend a lot. Like, our security,

model and our UX model for wallets is very, very highly dependent on humans catching mistakes, whether it's mistakes in, oh, is this the wrong contract? Am I getting spearfished? Or, you know, like, clicking through all these buttons to bridge from here to there. It's like, oh, make sure you come back in three minutes to like, you know, click do this other transaction. And clearly, the wallets should be a lot smarter than they are. They should be able to do a lot more of this, such as a human being, you're operating at a higher level of autonomy and direction giving compared to where the wallets are today,

which are extremely brittle. And there's almost no intelligence that's baked into your wallet besides a little bit of transaction simulation these days. I think that is going to be one of the most titanic changes that we see in the crypto industry over the next few years because of AI.

And I think in order to get there, you need to do reinforcement learning at scale with a really robust data pipeline and simulation environments in order to do that. And I haven't seen anyone really try to tackle this today. I think it actually requires quite a lot of capital. And I think it's a very hard problem to solve. And we're clearly not there yet.

Like we were not incapable of solving it today because, you know, models cannot consistently order pizza. They can't even consistently book a flight. What makes you think they can consistently, you know, bridge assets and do dextrades and, like, not get fished, right? Like, that's even harder than ordering a pizza. So, if you look at the latest generation of, models. I think if you look at, you know, the newest Claude 4 opus, some of these agentic

benchmarks, I think on ordering a pizza, it's something like 80% ability to order pizza and like 60% on booking flights, which is, you know, it's incredible compared to where they were a few years ago, but it's still abysmal in absolute terms, right? Like, if you had a personal assistant who could order you a pizza, 80% of the time, you'd be like, what the fuck is wrong? Like, I'll just order all my own pizzas. Like, I'm not even going to deal with this. So, but I think they will get there very soon. I would guess within a couple of years, we're going to have these things

consistently booking flights for us. And whoever wins this of being able to get AI and getting agents to work directly within your wallet and be as trustworthy as a self-driving car, right? If you think about, you know, I don't know if you ever taken a Waymo,

but, you know, today, you know, you take a Waymo in San Francisco or in Phoenix or in Austin, and it's just like, this is, I, I, I, trust this more than I would trust an Uber. It's kind of, you know, it's slower and it's more methodical today, but it's, it's almost certainly safer than going in an Uber. So when are we going to have self-driving wallets? And those self-driving wallets are going to totally change our experience of blockchains. I think this will be one of the biggest companies and one of the biggest

opportunities because of the fact that it's going to change our relationship with blockchains, right? Not just that, okay, I'll be able to tell my wallet, hey, move my assets from here to there, it said, I won't even care where my assets are. Because why would I need to care? I just tell, like, hey, I want to go trade on hyperlip. Go, go get me, you know, a 5x long on Bitcoin. And the wallet will just figure it out. It'll say, oh, well, my ass over here.

I'm going to go bridge. I'm going to do this. I'm going to do that. It's just going to happen in the background. Same way, you know, I tell my Alexa, hey, order me diapers and it just doesn't. Right? I don't need to deal with anything. That will happen.

You will trust the intelligence of your wallet enough to be able to delegate that task to it. And when that happens, how does it? change your relationship with blockchains? How does it change your relationship with Arbitrum? With Solana? With all these things. When I no longer care what chain this thing is on, I no longer have even allegiance to say, oh, well,

I'll only use Salana apps because, you know, I love Solana, I'm a Salana guy, right? That, I think, is going to be the biggest shift that we see in crypto over the next five years. And that, I think, that's the kind of scale of opportunity that if I was going to build something I would want to go after.

Yeah, I totally agree with you. I mean, I think one aspect of this that to me seems so crazy and illustrates like how crucial this is. It's just like wallet security, right? Because it's so, so hard. And it feels like it's actually gotten worse. I mean, at least, you know, back in the day, you know, everyone was like, oh, not your keys, not your coin. Self-custody. It's the way to go, right?

And it was very much. And like, you know, you don't want people onto crypto and they're like, you know, you have to write down your own wallet. I think today, you can often barely predict what are you signing. You have all of this fishing attacks, hacks, sophistication.

It feels like something where most people shouldn't actually use a wallet, right? You shouldn't do self-guise. And I think the only thing that can solve that would be something like this, where you can basically say, oh, I want to do this. And then there's some verification thing

that will translate it into a transaction verifies that this is really the right thing, what you want to do. So yeah, I think this is a massive one. If you look at smart contracts, right, in a way, smart contracts, we talk about how magical they are and how amazing they are,

but the thing that's obvious about them is that they're really not designed for humans. In a way, they're kind of designed for machines. Like, it's a lot easier for a machine to parse EVM bytecode than it is for a human being to do so, right? And it's certainly easier for them to parse solidity with like a, you know,

if you've got this diamond contract thing with like, you know, you can't even, you look at the code, you can't tell what the hell's going on. Even if you can read code, you can't tell what's happening. But an AI can very easily go and parse the contract

that it's interacting with. You know, simulate it, interact with it, go see what are other deployed instances of this contract? Are there any wallets that have been poisoned by it? check the DNS records, make sure nothing's changed recently. Like all this stuff, there's nothing stopping you from doing it. You could do, if you were sophisticated enough, you could do it, but you just won't, right?

You're lazy, it's slow, it's time-consuming, like you just don't have that level of patience. But an AI never gets bored, never gets lazy, you know? It's like, you know, a Waymo. A Waymo never does a rolling stop. It's kind of annoying that it never does a rolling stop, but it never does a rolling stop because it never gets a patient, right? It's just like, okay, here's a stop sign. I will come to a complete stop, and then I will start.

start again. And, you know, maybe we need to modify this behavior, but at the end of the day, it's completely configurable by us, the level of scrutiny and carefulness that these AIs will take. Now, there will definitely be attacks against AIs, and that will freak people out when the first time, you know, an AI does something purely that an AI would, a mistake only an AI would make, and that a human being would never make. But eventually we will get to a point that AIs are safer than humans for self-custody. And eventually, and I think not, not, it won't take too long to get there, that AIs will basically never make a mistake. of that kind, right?

Just because of the fact that it's actually pretty easy to understand, hey, the user wants to train in Uniswap, the user wants to use this app, the user wants to do this, user wants to do that. And almost every case, not every single one, but almost every case, if a technical intelligent person had reviewed this attack surface area, they could have figured out something went wrong.

But just nobody is ever doing all those checks all the same time, right? One of the things I think that is to be proud of is the industry, even though I agree with you, that wallet security is really difficult, it's really fraud, is that if you look at the amount of hacks that have taken place in crypto over the last five years, the amount of hacks actually at the smart contract layer

have plummeted. Almost none of the losses that you see anymore happening on chain are actually smart contracts getting hacked. It's almost always spearfishing, wallet compromise, some kind of malware, user error, and the reason why is that we've actually figured out how to write secure code now, which is, you know, thank God, right?

But, you know, like, if you even think about, you know, the Bibit hack, which, of course, unfortunately, happened relatively recently, one of the biggest hacks in crypto history, you know, full disclosure were investors in Bibet. That hack, you know, the question is like, okay, well, that, you know, that wasn't even no, like, you know, the smart contract itself was not compromised. It was the front end that was compromised. And if they had checked the actual hash corresponded to a clean computer computing the hash of what they thought they were citing, they could have noted the non-corresponding. between those two, right? And again, an AI could have done that. And AI could have, you know, went and, you know, spun up a virtual machine and go and verified that thing or ran the code itself. But, you know, they didn't do it. And maybe they would have if they had it for a time, but they didn't. In AI could have also just read the front end. If you'd read the front end, you would have seen that there was a special case in the JavaScript on the front end that said, if your wallet

is this, do this instead. Right. That code was there in the JavaScript payload that they were served. And as a human being, you're never going to see. see that. You're never going to, you're never going to check. But an AI will always check. And AI will always check. So that is my fundamental intuition where that comes from of why wallet security in five years will be much better than it is today. Let's talk a little bit about the market. So right now, the market is in a kind of interesting position, right? Bitcoin is obviously doing extremely well. And at the same time, most of or a lot of the rest of crypto is actually struggling a lot. I mean, I think sort of the entire altcoin market,

a lot of the new tokens that are launching, you know, of course, funded by VCs and where like VCs mostly invest, right, have basically struggled to find any buyers, you know, with some exceptions. What are your thoughts on where the crypto market is today? Well, there's definitely malaise in the all coin market. And you can see that there's not a lot of retail. activity in alts. That being said, I think in absolute terms, crypto market is doing okay, right? If you look at where is that marginal retail buyer

instead, the answer is that they're in public markets. So you can see with the Circle IPO, you can see with all these micro strategy and with all these treasury plays that are coming to public markets, that's where you're seeing a lot of the energy and attention really being driven. Now, crypto markets are very cyclical.

And we know that right now, in a cyclical lull. Most of the attention is on Bitcoin. Monetary policy is still quite tight, right? If you remember, back in the beginning of last year, we thought there would be six rate cuts last year. Instead, we got two. This year, we've had none.

And it's already halfway through the year, right? And again, we thought there were going to be more rate cuts this year. So we're continually being disappointed on macro, and all coins are by their nature very sensitive to interest rates, because interest rates are basically just the cost of risk. When interest rates go down, that means that risk appetite is higher, almost by definition, because people are being paid less to take less risk.

So when people are being paid very little to be safe, they're more inclined to go further on the risk curve, and all coins are pretty much the riskiest of the risky things that are out there. So all coins are by their nature going to be very sensitive to macro, and I think you should expect that to continue, is that the institutional bid that's arisen for Bitcoin is relatively unique, right? Because that has come about for reasons

that have nothing to do with the overall broad crypto cycles that we otherwise see. But if you think about where crypto was relative to the beginning of this year, you know, beginning of this year, all coins are probably 2x where they are now. Like, you know, Solano was roughly 2x where it is. You know, most all coins are probably roughly 2x

below where they were, or 50% below where they were at that time. I think you will eventually see a reversion, but it's going down to be macro that leads first. In absolute terms, it's very obvious that the positioning of the U.S. government, which has been the most powerful government in the world, waging war on crypto

over the course of the last year, the fact that that's completely reversed, and now we have the most positive and constructive government we've ever seen in the U.S. about digital assets or almost about any tech industry, that obviously should mean that Alta are worth more than they were six months ago.

Or like if you just think even before Trump was elected, Alta higher than they are now. So I think what's happening right now with the all market is an anomaly. I think it will eventually correct, but macro has to lead. And that might mean six months, might even mean nine, 12 months

before we see that change. But the one thing that you can know with absolute certainty is that the cycles in crypto are not over. There are more cycles to come and that's something I lose no sleep. being confident in. So the environment for crypto-b-cies obviously has also been challenging, right?

Because if you benchmark to something like Bitcoin, you know, which at this point is like super easy to buy for, you know, anyone really. Then I think, you know, a few funds have outperformed that. And, you know, I think the sort of the DPI, so the amount of money returned from funds is mostly not so great. I think fundraising has been very hard for VCs. Do you think the crypto VC market is going to change a lot? And like how does it need to evolve?

I think it's almost certainly going to change. It's already begun to change. So I think that change has taken place largely because most of the funds that were raised in CryptoVC were raised in 2021, 2022. And that was peak ZERP. ZERP stands for zero interest rate policies when all of the central banks around the world

were sending their rates to zero or even below zero. in many places. And that just meant that money was burning a hole in your pocket. You had to put your money to work somewhere. And that meant a lot of risky capital, a lot of, a lot of risk seeking capital found its way everywhere into private equity, into VC, into, you know, obviously crypto VC was one of those beneficiaries. So those funds have largely run off now. Usually in venture, you have a two to three year fundraising cycle, and then you deploy your fund, and then you go raise the next one. Almost everybody who raised big funds during that time is now coming back to market

or they're already back in market and those funds in 2021-22 have been drawn down. So once those funds are over, you see that the next vintage, if you can't raise that amount of money anymore, then you have to downsize or you just have to fold. You just have to go find some other line of work.

And for a lot of VCs, that's the answer, is that it's not just that, oh, they can't raise as big of a fund as last time, it's that they can't raise at all. You know, if you raised $150 million and now you can raise, you know, 20. Those economics mean that you have to fire your whole team, right? You can't, you can't run a fund.

You can't keep your team. You can't do what you were doing before. And so a lot of people, I think, just quit if they realize that they can't really do that anymore. Now, we're in a relatively fortunate position that we have a strong brand. We have strong returns. And, you know, there are a lot of LPs that know us

and want to continue working with us. But I've seen even a lot of the brands that you know and love really struggling in market to be able to get, you know, fund vintages that are even comparable to their previous sizes. You can see for some of the funds that have been announced, significantly smaller than they were in 2021 for a lot of these name brand VCs who've come back to the market.

So what does that mean for the industry? A few things. One, it means that there's a lot less money and a lot less froth in investing into companies both in the early stage and the late stage. Now, that may correct as you start to see other forms of capital come into the space. So if you see more growth capital and more pre-IPO investing, I think that's likely to be actually pretty robust because there's growth capital

that's willing to touch crypto now, especially in the fintech stable coin space. But in the crypto-native stuff, that's where it really is just the crypto-native VCs that invests into, layer-ones and layer-tos and things like this, dexes and so on. And this capital is much tighter,

and everyone already feels it. So I think what it means is fewer VCs. I think it means more rational pricing. I think it means that founders the bar to raise money in crypto and to be a successful funders higher than it's ever been. And many people were thinking that, oh, well, there's going to be mean reversion. Like, it's going to go back to the way it was. Things are going to be hot and crazy again because, you know, Alts just haven't moved.

And if Alts are moving, then everything's going to change. And I think that's actually not true. I think that even if Alt start to move and you start to see like, okay, some of these funds are getting good DPI and so on, the reality is that the environment we had in 2031 will never come back. we're not going back to ZERP again and we're not going back to the amounts of money and the splashiness that you saw in 2021 where deals were getting done

with no diligence, super fast term sheets, you know, half-baked ideas, getting $10 million, that is not going to come back, even if asset price is too much better. It does mean that valuations will go up, but those valuations will be fought over by a smaller set of VCs,

moving at a pace that's more akin to what traditional venture has always looked like. If you think about it, from the perspective of someone starting a crypto company today also feels like a very different environment, right, where it's a lot more matured, a lot of things have become very competitive. As you pointed out, the fundraising environment is more challenging. What's your sort of main advice for someone wanting to start a crypto company today?

What should they keep in mind and what has changed about, like, how you should approach this today? My very glib answer is nothing has changed. The reality is that founding a startup in crypto was always hard. Every single moment that I can remember, it was always hard. Founders never thought it was easy to start companies and to build things in crypto. Even in times in the past, like if you think about 2017-2018, which was the golden era, where a lot of the most important projects were first built, I remember what it was like. I remember how those founders felt at that time.

And the answer was that they felt like shit. They felt like it was really hard. They felt like they were struggling to get access to capital. They felt like the world didn't care about what they were building. And you might think even, you know, 2021 was the party years. You know, that was when everything was crazy, money was really loose. You know, everything felt kind of wild and splashy. But even then, you know, I remember when a lot of these companies were raising their seat rounds

and they were struggling. And it's just like, yeah, okay, I can get some vanity metrics or I can get a bunch of Twitter followers, but can I actually get people to use my product? Can I actually go hire a team? can I actually go, you know, build something that the world cares about. The answer is that it doesn't really matter where you are in the cycle. Building companies is hard. Building products is hard.

Just even the act of deciding I'm going to go, leave my job, stake my reputation and my future career on the success of this crazy idea that nobody believes in but me. That's hard and it will never not be hard. So at the end of the day, you don't know where markets are going and you can't time things, right? Nobody in 2018 was like, you know what? That was a great time to quit my job and go all in on crypto. Turned out to be right,

nobody at the time thought it was a good idea. In 2020, it turns out that actually it was a terrible time to start a company. Most of the companies in 2020 are failing miserably and do all the time. I thought, oh, it's a great time to quit my job and go, you know, do some crazy thing. So the reality is that you just don't fucking know.

And at the end of the day, starting a company and going into, you know, building something and staking your reputation on it is an immensely personal decision. And that's where your conviction and your willingness to do it should come from, should not come from, hey, I think the market's good timing, is this and that, blah, blah, blah. Who gives a shit?

You don't know, I don't know, nobody knows. Right. If you have a good idea, if you really believe in it and you believe in yourself, go build a company. And if you don't, don't. Cool. I have two more questions when I ask you about. Before you ask you that question, Brian, you are yourself an entrepreneur. Yeah.

What would you say? I mean, I feel like the, you know, just the key is to find something. I mean, I would always use that approach if I wanted to start another company at some point. You know, I'd want to find something that, of course, one, I'm like deeply passionate about and that I would be willing to keep working on for like 10 years, right? And I think that is one of the things that wasn't, like, I wasn't so cognizant when I started course one, for example, was just that like, okay, once you go down a road, right, once you choose something, right? Like, you have to stick for, right? Like, you have to, you have to,

you have to see for a really long time. So I think that is one thing that I think is like super crucial. And then, I mean, I am personally very, like, avert, like, I have a strong instinct of like wanting to go somewhere that is kind of overlooked and ignored. And, not hot and where I'd feel like, okay, this is something that, you know, will become really big. Which, you know, I think a lot of people have the opposite instinct, right? Because maybe a lot of people are very good at execution and they're like, hey, this is an obvious opportunity. Let me go and compute with everyone else.

And, you know, some people can succeed that way. But I think right now you just see so much copy cats, right? It just feels like a vast majority of stuff. It's just people saying, oh, this worked over there. Let me do the same thing over here. And that's, it seems very short-sighted, right? Because even if maybe you have some initial success, and it's probably a lot easier to get initial traction with a lot of this stuff,

because, well, it's already kind of worked somewhere and you can replicate it. Then I think that to actually converting to something that works in the long term really hard. And I think the other issue I see is, I think people are just going to get bored of this stuff, right? And they're like, ah, this is kind of lame, right? The thing I'm working on. And then I think that's the worst thing, right?

Because then I think the founders will get bored. It will be harder to hire people or the people will be very mercenary and kind of come and go and move to the next thing. So I think it's, and I think crypto, has, I guess one of the things we are seeing, which I think is a challenge for the industry, is that it's become more something that people see as, hey, this is an industry where you can make a lot of money quickly and a lot of opportunities. So I think it attracts a lot of those people. And then a lot of people, I know, you know, who've been in crypto for a long time,

I feel are increasingly not that excited about it anymore. So I think this is actually for the first time, like last year, this year, where I see a lot of people I know who've been around for a long time who are kind of like, maybe I want to do something else, something like not in crypto anymore.

Whereas, you know, a lot of these people were like so passionate and so driven and like so ideologically motivated. And so I see that as a, you know, big, challenge for the industry as well. Yeah, that's very well said.

There's a line by Sam Aldman where he talks about, you know, when he was at YC, originally he would talk about, a very common advice would be, okay, don't try to come up with some super crazy, extremely ambitious idea because it's just too hard and you'll never be able to tackle that as a startup. And after he came to open AI, he said that he realized that he'd been giving bad advice at YC. And then actually, when you, when you, when you, pick something that's really ambitious, that's like really crazy, and they're like, okay, we're gonna build AGI.

It's like, okay, it's so unlikely to exceed, it's so capital intensive, it's crazy for a startup to wanna do that. But the one thing that you will do with almost certainty is you will attract followers to your cause because people wanna work at a company that's ambitious. They wanna go do something crazy. They wanna go do something that will change the world.

And you'll be surprised at the level of credulity that people will be drawn to and they'll say, like, fuck yeah, I don't know if we'll pull it off, but like, let's try, let's go try to build it. AGI. And that is something that's resonated more and more for me in crypto. A lot of people, like you said, they try to play smallball. You know, I think like, oh, well, you know, someone did this thing on this exchange or on

this, the chains, I'll go poured it over to this chain. And it's like a very safe approach to building a company. And it's like, oh, probably win. But you're absolutely right. It doesn't attract great people. It doesn't attract great investors. And like at the end of the day, the really, like the things that really energize people is, always first and foremost ambition. And that's what, that's what, you know, employees want to see. It's what investors want to see. It's what the world wants to see.

Like, the world will reward you for having an ambitious idea. It might not succeed, but it'll be a hell of a lot better of a ride for you than going and building, you know, the MF Y on a Z. Yeah, absolutely. I heard this other interview with you, where you said that you think discipline was, like, the most important contributor to your success. like how do you think about discipline? How would you define it?

And what's your advice for someone who wants to become more disciplined? Oh, damn, this is very, this is very like general life advice. I don't know how good I am at this, but I'll give it a shot. So I would consider myself to be a very, very disciplined person. I think I've been that way, not all my life, but for much of my life. I work pretty much all the time. I don't drink anything but water. I get to kind of eat, work out very,

follow a regimen very seduously. And like my ability to stay focused on one task, not just one task, but like one meta task, you know, not just literally, okay, I'm writing and I'm going to write for the whole hour, but just, you know, I'm going to be a great investor

and I'm going to learn everything that I need to in order to be a great investor. The discipline to just keep doing that over and over again for years is very rare. And so discipline, I think it's something I intentionally cultivated when I was younger because there was something I knew I didn't have. You know, when I was younger, I was a school,

I was a serial procrastinator, I was super lazy, you know, I just played a lot of computer games and didn't really give a shit about a lot of things. And it was something that I really didn't like about myself is the fact that I was very undisciplined. I think I was obsessive when I really, you know, catch my teeth, in something, you know, I'm the dog that can't let go and, you know, just gets dragged by the

tailpipe by the truck, you know, for many, many streets. So I've always had that quality in me, but being able to intentionally think like, hey, this thing that I don't want to do, it kind of sucks, I should just go do it. So I think that is one of the qualities that I have and that also intentionally cultivated myself. And I think if you're asking the question, how do I become more disciplined? I think the answer with all these things is just practice, right? So how do you practice discipline. The answer is, okay, what's something you think you should be doing? How do you, how do you create a system that forces yourself to do it? So I'll give you one example. I know that as a VC, it's very important to me to build, it's very important for me,

to build my public brand, to tweet, to like, kind of be out there, right? And, you know, over the last few years, I've, you know, my voice has very much risen in volume and in, you know, having a spotlight within especially crypto Twitter. And that was very intentional, It was not an accident that I was able to cultivate my voice in that way. But one of the things that most people don't know about me is that I actually don't read Twitter. I actually block all feeds on my phone. I have a rule. No algorithmic feeds on my phone ever.

Everything that I try to do is poll-based rather than push-based, meaning I don't want to be told, hey, read this, read that, da-da-da-da. I want to intentionally go and choose. I'm going to read this. I'm going to go look for this information, et cetera. And so my relationship with Twitter is like literally I block it. I block the feed. I have a like browser extensions that block all feeds on my browser and I don't have the mobile app install on my phone.

And nevertheless, I'm tweeting very regularly. A tweet actually I have a rule. I tweet once a day every weekday, at least once a day every week. And if I don't, any given day, I have to pay somebody $100. And I've been doing that now for years because the honest of God truth, I hate tweeting. really don't like social media. But I do it, intentionally cultivate it, and for a long time, the way that I did it

is that I would force myself to do it. And how do I force myself to do? The most excruciating thing you can do is to send $100 to your friend and be like, don't donate the charity, don't do something good with it, go waste it. That's going to really piss me off.

And I've been doing things like this for years as a way of cultivating this habit in myself of just tweeting regularly. it's like a muscle. Like now I just, oh, I got a tweet today, boom, boom, boom, you know, get it out there and, you know, try to write something that I think is going to resonate with people. So this kind of thing, you know, just multiply that by, you know, everything that I'm doing in my life that I find is important. You can do that. Anybody can do that. Anytime they want. It doesn't have to be $100, it can be $5. But it just has to be like,

look, you know the things already that you wish you were doing that you're not doing. And in a way, like, how can you create? The one thing that you learn in order to actually cultivate discipline is not about being disciplined, right? Like, one thing that you have to assume about yourself is that you are a lazy piece of shit. You know, that is how I model myself. I am a lazy piece of shit.

And the only way that I will do things is if I have to, if I either pre-commit myself to doing it such that I can't back out of it, or I've created a structure that is going to force me to do it, right? it's sort of environmental design. These two things, to me, are the core of how you ultimately cultivate discipline. Is by either making public commitments that you can't go back on, or by creating these structures around you that are going to force you to do it. And if you keep doing those things, eventually people look at you and they'll call you disciplined.

Right? It's like, when people look at me and they call me disciplined, I'm like, that is not how I pursue. I have a lazy piece of shit. I know myself wants to know that if all these structures fell away, I would just, you know, I would lie in bed and play video games and smoke dope or whatever. Like, I would be absolutely useless as a human being. So this, these things come from what you put into it.

That's the best answer I can give about how to call the fate display. I think that's a fantastic answer and it definitely resonates. Maybe this is the final one. So do you, you know, you're someone who's very curious, right? You like to explore different things, learn. I mean, you've made, you've had some, you know, very, fundamental changes in your career and focus, do you think you'll always be an investor

or do you have something in your mind or like, okay, one day this is what I want to do? I will always be an investor in the sense that I will always be investing into things, but will I always be a professional investor? I doubt it. I think I'm somebody who I naturally have moved through many different domains

in the course of my life and I'm almost certainly not done. That being said, I'm very committed to building Dragonfly and to investing into what I see as the generations of crypto technology that are still yet to be fully done.

But there will come a time when crypto is basically done. Not that crypto's not going to change anymore, that there's not going to be new founders or new startups, but if you think about, like, for example, social media, social media really stopped being venture investable

after about 2010, right? Now that being said, social media companies between 2010 and 2025 became the most important companies in the world. Social media won. The thesis was absolutely correct, but there's really nothing more to do as a VC, right? Almost every single social media company

was already built before 2010. And so I think that's probably, probably going to be true of crypto at some point. I don't think it's true yet. But it will be true of crypto at some point that all the most important companies slash protocols are basically built. And the growth is going to happen

in public markets, not in private markets, the same way that happened in social media. And I think that will be the point at which we say we were right. We won, right? All the things that, you and I, when we first came in this industry, all the things we were saying

that nobody believed us, we were vindicated. But there's nothing more to do as a VC. Like, you're done. Hang up your hat. go do something else. I don't want to

overstay my welcome as a VC. I don't want to be clinging on and raising funds when I don't really believe that there's still this golden era of opportunities of companies and protocols

to be built. I think there very much obviously still is and you can just see how much, you know, Solana just went from nowhere

to being a dominant chain in the span of like a year and a half. Like that just happened. So very clearly, like we're not done. There's still an enormous rate of change in this industry.

But is it going to last 10, 15 years? I don't know. Maybe not. And if not, I will hang up my hat and go do something else. Cool. All right. Well, thank you so much, Seab.

It was a huge pleasure to have you on. Really enjoyed the conversation. Thanks for having you. Thanks very much for coming on. It was an honor to be on. If I had told myself seven years ago that I'd eventually be on Epicenter, I think I would have been elated. So thanks for having me.

Thanks so much, Aesib.