Haseeb Qureshi: You Will Suck Online If You Aren't Vulnerable (Building a $4B Fund in Public)

I agree with that in part and I think it depends a lot on what you're doing. For most startups they will never get a call from New York Times or a regulator. Most startups will just die in darkness and you sort of eventually earn the right for the New York Times tech reporter to call you a scam. Now that said, I think if you look at the big founders in our space, the people who are, you know, the Polymarkets and the Hyperliquids and so on, for them being able to speak across multiple registers is really important and you can see that we haven't always done a good job of that as an industry. In fact, we've had some pretty horrific missteps if you look back at some of the big founders and CEOs in our space who've done a real disservice by the way that they've failed to really congeal a story about why what they're doing is valuable for the world.

So, yes. And I think it's a yes and.

Yeah, that's a heavy question. So the short version of the story is that when I was a professional poker player, I backed this other player who ended up cheating and I defended him and that ended up blowing back on me. I was 21 at the time and I had no idea how reputations worked. And I think moving on from poker after that, I was very young and I dropped out of school to play poker. I was a professional while I was sponsored. And so that was kind of the only thing I'd done in my life was build this career as a poker player. And when I left that behind and I had to figure out who I was and what I wanted to do with my life, it was one of the hardest and probably darkest chapters for myself as a person because I had been playing poker professionally from 16 until I was 21. I'd made a bunch of money as a young man. I made a name for myself. I had all these people who looked up to me, who adored me, who I thought I was an amazing person, who then went to looking at me thinking that I was this piece of. And that was probably the hardest thing that I personally have gone through is this feeling of total rejection from my own community. Now, in retrospect, I think all of this was a tremendously valuable lesson for me in being able to one figure out who I really am and what I really value as a person. And you're only ever going to really learn that by being confronted with the parts of yourself that you like and the parts of yourself that you don't like. And so my own fear of being associated with this person or my fear of him being found out and as a result my relationship with him being found out led me to lie to people and try to deflect my relationship with him. I learned through that two things. One is that it's so important to always be honest, transparent, and direct. And that's a big part of what's led to my cultivation of myself now as a public figure is my first instinct is always just say what happened, just be transparent. The reality was I didn't cheat, I didn't actually do anything, he's the guy who cheated, but I was so afraid that my relationship with him would tarnish me because people would think like, well, if you're so close to him you must have cheated. And ironically the fact that I was trying to distance myself from him was in fact the thing that ended up tarnishing me. And so I've just learned, there's an old saying I can't remember who said it, but anything that you wouldn't be comfortable reading in the newspaper, don't do it. And that has taken me a long way in building my career and my intuition as being a very public person.

And the second thing I'd say is you have to learn at some point that your power comes from yourself and your ability to move forward in your life and accomplish your own goals. It doesn't come from other people. And if you're really convinced that other people are the source of your capabilities, then you are going to be very, very afraid to do anything that's going to upset people. And so I learned through basically the hard way that I was the only one who was going to be responsible for my own success and my own reinvention. And that is a large part of what gives me confidence when I go out into the world and I say an unpopular opinion or I do something that might piss people off is that look, if people are pissed off at me, it's okay. I think about some of these folks who are extremely public in careers that are often very non-public. I think a lot about Bill Ackman. Hedge fund managers are notoriously very private. They're very behind closed doors. They don't upset people. They basically want very much to enjoy their billions in privacy. And in fact it's a big part of why you want to make a lot of money is to retreat from the public eye and to not be in the crosshairs. Bill Ackman is the exact opposite. He is an extremely public, almost pathologically public person. I don't know that much about his returns but it's obviously a large part of his power is the fact that he's had a lot of moments of foot and mouth syndrome but he goes out in the public square and does it again and does it again and does it again and that's what earns him the right to keep doing it. And I actually think, not that I want to emulate him per se, but I think about him as being one of these quintessential examples of the different ways in which you can vest your power in your public persona that allows you actually to advance your career in places where people normally think that the risk reward is only to the downside.

Well, I think the answer is always both. And the two of them, they co-create each other. I remember when I posted this article about how to build a VC firm, there was one founder who commented, 'Oh, you're only saying this because you're a famous person and so because you're famous, you were able to build this great firm.' And it's like you have exactly the other way around. When I started this, nobody knew who I was, right? My public reputation was co-created with this firm and the two of them fed on each other. As I built my reputation, I was able to build Dragonfly and as Dragonfly was built, it was able to build my reputation. And so I always think of it the same way is that it's a conversation. The two things are working together with each other. The more that you build your public brand, the more you're going to get into great deals and great founders are going to want to work with you. And your ability to tell the story and to have that megaphone and to have some influence and be a marker of taste and quality is going to help those projects succeed which helps bring the next project that wants to succeed. And it's a virtuous cycle. Without that cycle it's really really hard to succeed in venture. You have to have some kind of unfair advantage. We didn't have any obvious unfair advantage. We're not A16Z or Sequoia or whatever. So we had to build it and the only way you can build it is through this kind of co-creative loop between building your brand and building the brand of, the way I describe it in venture is famous for being famous where people want to be in your portfolio.

I think I am. I think I am. Yeah, I'd say so.

I mean, when I started investing, I was at another firm called Metastable, which was a very early crypto VC founded by Naval Ravikant. And when I was at Metastable, Metastable was a legendary fund at that time. It was one of the largest funds in the space. I think it was probably second only to Polychain at that time. And of course, Naval was such a well-known public figure that it was really easy for us to get into deals. And so when I was at Metastable, I never had to fight for a deal. Basically, we would decide, everybody would come talk to us and we would just say, 'Oh, this one.' And we'd say, 'Hey, Naval, go talk to them and get us some allocation.' And he'd say, 'Yep, they got it.' And they would always give us allocation. And so that's what I thought investing was when I was at Metastable. And so when I left Metastable and came over to start building out Dragonfly, that was not our experience. I kind of realized like, oh, winning allocation in deals is hard. People don't want to give you any space in the round if they don't know who you are or why you're valuable. Every single deal you have to earn it with what you bring to the table and you have to convince them that you've earned that slot on their cap table. And so that's when it really clicked for me. When I was at Meta Stable I was public and I tweeted stuff, whatever, but it was not with the same level of rigor and seriousness that oh, if we don't do this, if we don't manage to build this brand and get people to really know who we are and put ourselves on the map, we have no shot of winning. We're going to be relegated to being this second, third tier player. So I was like, 'Okay, challenge accepted.' When I started Dragonfly, Dragonfly had no public presence whatsoever. There was a website with just a little logo on it and nothing else. And I remember I started a blog called Dragonfly Research, which was really just my blog. It was just me kind of writing like kind of smart stuff that I was thinking and calling it research. At that time it was pretty easy to pass something off as research because there weren't a lot of people who were writing in-depth stuff about crypto. And people were like, 'Okay, well, I guess that's, if you're calling it research, sounds like research.' And I had a couple articles that ended up getting a lot of attention, getting people talking. And for a lot of people, that's where they first discovered Dragonfly was just these blog posts I wrote about kind of shower thoughts about crypto. And that's how you do it, you slowly, gradually build a legend. And eventually you step into that legend when you have the ability to prove it. So eventually we did have researchers and we did have an actual research team. But in the beginning, no, it was just me writing things that I thought would sound smart.

I'm not going to reveal my sources.

Yeah. So a few reasons. I find TV to be, I mean TV is like the kind of standard prestige media, right? It's like, 'Oh, you've got a byline in CNBC or Bloomberg. You can put it on your thing. You can add it to some list.' All love to our friends, by the way. Yeah, you're all great. I'm sure they're not watching this, so it's fine. I'm kidding. Here's what I'd say is that TV is kind of the standard most low context viewer. It's somebody who just happens to be watching a channel in the background, probably muted while they're at work or something like this. The level of engagement somebody has with TV, of this sort of transient low context media, is just very low. And in general, my view is that the reason to get on TV is either you're on one of the blockbuster shows, like you're on Squawk Box or something and people are actually watching this, or you're basically there for this kind of background prestige. But the difference with podcast, the difference with long form is that one, people usually listen to long form and they're engaged because they're driving or they're working out and they're actually listening to the whole thing. It's not just background noise very often when they're engaging in this kind of media. And second, they really get to know who you are. They have a lot more texture about who this person is as opposed to this person is a stand-in expert on this segment that we're doing today. When you're on Bloomberg or you're on one of these TV shows, you are cast into being this, we need somebody to be a civil engineer to talk about why the bridge fell down and you are a civil engineer and they give you the little by line and here's where you work, but that's not what's important. What's important is that you're commenting on this story that we're talking about today. Whereas with long form, very often it's not like, we're not talking about some story, we're not talking about some thing. We're talking about each other and we're talking about ideas and that stuff is much more likely to stay with people and to have an impression on them. So even if let's say it's some super prestige media prime time daytime TV, maybe it has 10 times the views of a podcast, but the people who are listening to that podcast are going to be really listening and remembering the things that I'm saying and it's going to be much deeper about who I am and make an impression of like oh I think I understand who that person is. But on some daytime TV I'm going to get in three points about whatever the story of the day is and that's pretty much it. So that's why I prefer podcasts over traditional daytime TV.

I mean look, I will say you have to be thoughtful about what podcasts you do because there's an infinite number of podcasts. Sure. And so there are, you know, just a random dude in his basement who's like, 'Hey, I'll bring you on the blah blah blah.' And it's like, 'Okay, this is maybe not worth an hour of your time.' But for the most part, I mean, the other advantage, of course, is that with a lot of TV, you have to like go into a studio and there's a lot more. Get your hair and makeup done. My hair is a real mess to do. So that does take a lot of time. And yeah, it's like and you get all of that for like a 6 minute appearance in the middle of a Bloomberg show. Whereas for a podcast, like you can, for a lot of podcasts, you literally just turn on your camera and then you go. So the amount of time that you're spending in order to get the content is much more efficient. That said, if it's TV that I think is really valuable, so it's got a lot of distribution or it's something that is a story that I think is going to, I want to get out to this particular audience. The other thing to understand is that TV and podcast have very different audiences and the kinds of people going to be watching Bloomberg TV or watching CNBC are very different from the people who might be listening to your podcast or listening to a different podcast. So, or your own, or my own. So podcasts have very different audiences from each other. It's not as though there's a podcast audience. And so you have to be thinking about what is the audience for the show and is it important to me to get in front of this audience? So there might be some random public interest thing that just is totally irrelevant. Might be fun but it just is not useful. Some podcast about, I don't know, men's style or something. I don't know why they would... really important. That would be a very strange guest for them to have on that kind of show. But yeah, it would be totally irrelevant to any of my professional goals. Even though it might be a lot... Your next business could be a fashion line. We don't know. Dragonfly has to go really badly for that to be my fallback. But you know, if there's a show that has very few people who watch, but they're all really powerful people, then okay, maybe I want to be on that show.

TBPN. That's right.

Okay.

A wise man wrote that.

When you are an upstart, it's very very difficult to be thinking in terms of power because power is something that everyone else has. And so a lot of what you're doing when you are an upstart is you are cultivating your skills. You're cultivating individual abilities of okay I can help you with recruiting, I can help send out a message, I can help you with BD relationships, I can help you with this, I can help you with that. The bigger you get and the larger scale that you start competing on the more power starts to matter. And power, it's difficult to define. It's somewhat amorphous, but you know it when you see it, which is that this person can solve problems for me, they can move other powerful people. And a lot of what startups do is that they have skills, they have abilities, they have knowledge, they have competence, but they don't have power. Big companies have power, right? Incumbents have power. And I came to realize this from there was an interview that Marc Andreessen kind of put it the most lucidly of anyone that I've heard, which is that the business of venture capital is renting your brand and your prestige and your power to startups who don't have it yet but will get it soon. You're sort of lending it against them and against their name is principally the most important transaction that happens in venture capital and that's why it's very important to have power, to cultivate that power so that you can give it to the people who deserve it.

Yeah. Okay. Rapid fire.

I listen to, there's a video on, there's a YouTuber. He's a monetary economist. I forget the name of the channel, but there was a long form video where he talked about the myth of the petrodollar that I found actually very fascinating and I didn't know very much about it. And so it was actually one of the biggest kind of mental shifts for me. The short version is basically that there's the common story about the petrodollar is that when Nixon basically broke the gold standard, there was a deal that was struck with Saudi Arabia that the oil was going to be priced in dollars and this was the birth of the petrodollar, which is that the oil trade being denominated in dollars is what ultimately buoys the value of the US dollar after you break away from the gold standard. And the assumption was that this deal with Saudi Arabia was, in exchange for us militarily protecting you with the US military, you agree to price all of your oil sales in dollars. So I'd always heard that story. That's like the standard story that you hear. It turns out that in 2016, through a FOIA request, the actual treaty that was signed with Saudi Arabia was declassified and was basically revealed for the first time in 2016. And in that document, it's very clear that there was no agreement to price all oil in dollars. In fact the agreement was not to price oil in dollars. The agreement was for Saudi to stabilize the price of oil. That was the agreement. And there, it's a broader thing. I recommend that you look this up about the myth of the petrodollar. It's very very interesting. But it's one of these things that, especially if you're in crypto and you're in these kind of monetary circles, you just hear these stories that are told over and over again. And it's always I find very refreshing to come back to first principles and understand like, hey, is this really true? Because of course, there's all the story about Iran pricing their oil in yuan and now in Bitcoin. Is this some violation of the petrodollar myth or the petrodollar's monopoly? Does that mean that the US dollar is going to fall off a cliff? Of course, the US dollar did not really respond to the fact that Iran is doing that. And the question is, okay, why is that? If the petrodollar is so important. And the other thing that he points out is that look, in the 70s the oil trade was an enormous part of international trade. It was an enormous part of what caused international finances to get settled in different currencies. Today, it's something like 1% of total international trade of dollars moving around the world is oil. Wow. Actually because we're net exporters now and there's a lot else that's going on that explains that. A much bigger share of demand for dollars is actually manufacturing. So our relationship with China actually matters way way more than our relationship with the oil trade and OPEC countries.

Yeah. So anyway, that is my answer to your rapid fire question.

I don't know. I was in Costa Rica a few years ago and I just saw the major highways and infrastructure they were building there, the ports, just making these developing nations totally dependent.

I think it's more complicated than that. But we don't have to necessarily go into it. We're doing rapid fire. It's not very rapid fire.

The hill I'm willing to die on. Ooh. I think the First Amendment. I'd say free speech.

No, I am very alarmed by the march on both the left and the right for increased censorship. Censorship. You know, everybody cries that, oh, we're being censored and their antidote to that is censoring the other side. And I think the intuitions behind liberalism are dying in our country. You can see it very clearly in young people. Young people do not overwhelmingly believe in free speech. And I think it's a principle that right now it's basically just a system of law that is protecting the institutions that I think led to our liberal society. And I think they're at real risk of eroding. So that's a hill that I would die on.

You're welcome.

Who should you have on the show next? I would say Erik Voorhees is somebody you should have on the show. I think he'd be an amazing guest.

Yeah.

Thank you for having me, Evony. Appreciate it.