The Wolf Of All Streets - How To Win Crypto's Next Bull Market | Rob Hadick

Episode Date: August 9, 2026

Rob Hadick discusses how institutional adoption is accelerating even as retail activity remains weak. We cover the growth of prediction markets, stablecoins, and tokenization, what caused the October 10 liquidation event, and why the next crypto cycle could be more selective, with stronger fundamentals and institutional capital driving the winners. Learn more about your ad choices. Visit megaphone.fm/adchoices

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prices may be struggling, but behind the scenes institutional adoption is accelerating. Today I'm talking with Rob Haddock from Dragonfly about prediction markets. It looked to me like it had started to permeate more of the non-tech forward or the non-cryptoculture. Tokenization. The perfect world is one where everything is tokenized and we can get tokens to be the only source of value accrual. Stable coins. If stable coins and tokenization is like in the water supply, everyone has to drink water.

And so every company will be a water dispenser at some point. in time. And why companies like Polymarket are growing regardless of what Bitcoin does. Polymark is being referenced as a source of truth. Polymark is just had their best month ever in June. They don't care what the price of Bitcoin is. We also break down what really happened on October 10th, why retail disappeared and what the next crypto bull market could look like. Are institutions building the future of crypto? While retail sits on the sidelines, we're going to find out. Let's go. Today's video is sponsored by 21 shares, not financial advice. Investing Carey risk, products might not be available depending on where you are. Talk to a financial advisor.

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Follow at 21 shares and at 21 shares underscore U.S. on X for crypto education and market commentary. They've had Haseeb on the show like 50 times. Great. On that, I could be. Why haven't we done this before? It's my fault. I'm assuming, But, you know. Maybe it's your producer's fault. Yeah, that's right. We need someone to play. But I'm glad that we're finally doing it.

So obviously, we're out here at the Audi summit. What are the sort of prevailing narratives that you're hearing or that you're interested in on the ground here? Yeah, I mean, this summit is pretty institutional, as you can tell. So it's been pretty interesting to see there's about 330 people here. But, you know, basically all every bank, every asset manager, a lot of the different. investment companies with the traditional investment companies are here. They're, you know, very focused on the things that you would think those people are focused on. So stable coins, tokenization, the future of AI, what does AI look like and how does it interact with crypto?

How do we, you know, how do the market's going to do? What is clarity act? And how is that going to affect, you know, the markets? And that's been the prevailing narratives. And so I think your listeners won't be surprised because that's a lot of what the narrative has been in the market recently. And we've seen the market get more mature, get more institutional. But it's exciting to see this much interesting. from, you know, all of the big name, you know, financial companies in the world.

Agreed. So that doesn't necessarily align with how you actually allocate capital. Yeah, it's from a venture capitalist perspective, you know, it does make it interesting right now to figure out how you're going to allocate capital. We've been, for Dragonfly, we've been obviously a little bit different in the way that we've thought about the space than some others. And so we've always viewed this space as financial technology. And so we've always invested in the infrastructure and then we've invested in decentralized finance. centralized financial companies, prediction markets, payments companies, stablecoins. That's been the prevailing narrative within all of our funds, basically.

And a lot of those things are doing incredibly well. So we have a couple of portfolio companies. I heard you just talked to Christian Carlos, obviously very close to Polly Market, where one of the largest shareholders there have been in them for several years. And, you know, Polymarket just had their best month ever in June. They don't care what the price of Bitcoin is. We have another portfolio company called Rain, which does Stablecoin backed credit cards. And every month that I've been in that company for the last year and a half has been their best month ever.

And it doesn't care what the price that Bitcoin is. So it's been very interesting to see where we have a lot of these very crypto-native investments, especially on the defy side of our portfolio on the infrastructure side, who have struggled since 10-10, at least on the price action side, maybe not from the adoption side. And then with the adoption picking up, these other companies who are just doing incredibly well, despite the prevailing sort of, I think, kind of lingering concern that a lot of the investors and a lot of the market has had. You brought up 10-10.

It doesn't get brought up as much as it should still. Probably. So what's your view on what actually happened there? I haven't had the conversation in quite a while, and maybe now the dust is settled, there's actually a conversation to be had. Listen, I think 10-10, listen, it's pretty clear that there were mistakes made at certain exchanges. Stakes were made. Yeah, mistakes were made.

in infrastructure and risk management at certain exchanges that created this, you know, dislocation of collateral, and that dislocation of collateral meant there was a depegging that shouldn't have happened, and that wouldn't have happened if people were appropriately building the infrastructure for the way that everyone had warned and expected that they should be doing, and that created this cascading liquidation effect that, you know, ended up being the worst day in crypto history because of that. And, you know, there's a couple of narratives there. One of them is about, you know, making sure that we continue to act like a mature enough

industry that has risk management and counterparty risk at the top of our mind. Another one is how we think through, you know, the types of leverage that we allow for products. And obviously, there's retail hunger for a lot of leverage, but is that the most appropriate way to, you know, get access or give access to a lot of different, you know, retail traders, depending on what their level of sophistication is. And so I think there's a lot of conversations to be had, but it's very clear that there's a huge overhang because that was, you know, the worst day in crypto history.

It was over a million individual accounts, I think. For whatever, 1.1 million people, those were, you know, there's not that many people here. Well, it's 100%. Especially when you enter the bare market, those would have been the people who probably would have still been participated. That's right. And I think what people forget to is that 2025 was not just 10-10,

but was probably, not probably, it was definitely the single worst year for crypto ever in terms of what it did to retail participants. Because, you know, we've had the Genius Act. We had obviously, you know, Bitcoin ran up to 120,000. But if you looked at what happened with the Trump meme token, if you looked at what happened with the tariff tantrum and kind of a lot of the liquidations we saw over that period of time,

then you saw 1010, the amount of accounts, the amount of capital loss by retail. leverage traders, it dwarfs the rest of what happened, you know, Luna and FTCS, etc. And when the retail investors don't make any money, when they continue to lose money for things that they might feel are unfair, whether you know, whether you believe that or not, they're not going to participate. They're not going to participate. They're not going to continue to trade. And so now we get this market where volumes are low, the active traders are low, the active accounts are low. But at the same time, you have this other thing that's happening,

which is that tokenization and stable coins, that institutional interest continues to skyrocket. And that's why we've got this sort of dislocation between, I think, price action and, you know, what's happening on the ground. It made such an interesting point because I think people would, on the surface, say 2020 was the worst, right? Because you have, block five genus. Block five Celsius, Voyager, FTX, all of them, right? Luna, of course.

But I looked back, and I think the volume on the day that FtX collapsed was like $1.2 billion in liquidations, and 10-10 was 19. Yes, that's right. The spaces just got so much bigger. So it doesn't matter what percentage. It's how many actual people lost their money that would still be here today. Interestingly, you know, we talk about having a responsible conversation about leverage and perpetual swaps.

And now we're just bringing them to everything. It is true. Instead, let's do perps on the weather. Well, what I will say, though. I'm not saying that's bad, by the way. Yeah, but what I will say there is, like, if you've talked to Cher Sealing over at the CFTC, like they are trying to be very thoughtful about the appropriate amount of leverage and the way that they roll these things out. It's not 100x leverage.

Correct. Right. And I think to your point, they serve a real use case for traders, but you want to be thoughtful around, you know, how you present them to traders, right? You know, we're in this interesting spot today where if you look at Robin Hood volume, 70% of options are the biggest part of their volume and prediction markets are growing. But of their options volume, 70% of that is zero-day options, right? So that tells you, like, you know, the type of trading activity that's happening on Robin. And there's real hunger for these things. How you roll it out in an appropriate manner and what type of sophistication you require, that's the story and that's the question that people are asking. And the CFTC is trying to get ahead of that right now. So you didn't become one of the largest investors in Polly Market by doing it last week.

I obviously saw it very early. Yeah. Right. So I would love to kind of dig into your thesis and thinking at the time when you made that bet because now it's probably one of those things. It was like, oh, obviously. Yeah. So I wish I could say,

it was obvious, but we've been in Polymarket for, you know, not that long, right? So it's been about three years or so, or a little less. We co-led sort of an extension around with Founders Fund in late 23. And it's funny because if you remember 23,

there was that weekend or Sam Altman got fired. And the, you know, he got fired on a Friday and then there was all this speculation about, okay, would he come back and will he be the CEO again? And the polymarket for whether or not he would be rehired

ended up being one of their largest week, I think it was actually the largest weekend they ever had in terms of trading volume. And I was seeing that a lot of my friends were texting me and they were saying, hey, have you seen the polymarket about St. Altman? And they were thinking, because this was on top of everybody's mind at the time.

And the polymarker was being referenced as a source of truth or everybody like a zero. Like a zero. You know, right? Yeah, exactly, right? It just became the term for a prediction market was the polymarket. The polymarket. And And, you know, we've known Shane for a long time. We, you know, thought about doing an earlier round, but we didn't.

But when that weekend happened and it became such a big part of the conversation, I really felt that there was, now was the right time. It was starting to permeate the, not just the crypto crowd, but, and prediction markets were already something that a lot of, I think, you know, tech forward people were thinking about. But we started to see the volume show up as well. And then at the same time, the Taiwanese election actually had a, it was the highest volume they've ever had for a foreign election. And so we're like, okay, so now it's not just U.S. elections.

And we started to see Joe Wisenthal from Bloomberg. And at the time, a lot of the political candidates were starting to tweet out polymarkets. And we had seen a little bit of that in 21, but it looked to me like it had started to permeate more of the non-tech Ford or the non-crypto culture. And I reached back out to Shane and I say, hey, let's go for a walk or let's have a meeting. And he was like, yeah, like, let's go for a walk. It was a Friday night. I still remember it. We walked for like two and a half hours through Washington Square Park in New York City.

And he just... That's why I got engaged. Yeah. Yeah. He's a New York guy. I got engaged in my. Oh, you got engaged. Yeah. As I said, I was like, he's, I know he's got a girlfriend.

Me. Sorry. Yeah. And beautiful, Plistic Engage. But yeah, and the story he told about wanting to create markets for everything was the same story he had said and told people, you know, years earlier. He had never wavered, despite the fact that. that, you know, it kind of had this big run in 21 and 2020 and then had the C of TC settlement in 22

and that they had kind of a big dip in volume. And you could just kind of see that he still felt very strongly about it. I started to feel a lot more strongly about it. And so we decided to do the deal at the time. And I think they were doing, you know, 50 million of monthly volume at the time. Last week they did $4.5 billion. And so it's the growth has been tremendous. I don't think, Shane would tell you that he would expect

He expected that growth, but I don't think we even, we expected that much growth that quickly. But it's interesting. Dragonfly, obviously widely viewed, I would imagine as a crypto VC, right? I know that that's diversified and whatever. But even at the time that you made that investment, you're probably looking at it as a crypto company to some degree or were you not. Yeah, I mean, we absolutely were. And, you know, the entire business at the time was just built on, you know, Polygon. Yeah. And they still have that. That's where the Polygon comes from. That's right. Yeah. The day I was like, wow, Alclans might really be dead is that you can't get polymarket, Polygon to move, even though Polymarket has a,

in the name and just chicken those words. But yeah, anyway, so you were viewing it as a crypto company at the time, right? Yeah, absolutely. Now, we've always invested in the idea that, you know, a lot of finance or all the finance maybe will happen on chain. And so, you know, in some sense, if stable coins and tokenization is like in the water supply, everyone has to drink water. And so every company will be a water dispenser at some point in time.

So if that's the case, then, you know, the aperture gets a lot pretty big. So, yes, it's a stable or a crypto company, but it's a financial company. And that is where finance is going in our mind. Okay. So talking about everything ending up on blockchain rails, I think. So you have a unique insight once again as a VC. And I think that maybe aligns better with retail than, you know, what Morgan Stanley or Goldman Sachs is doing.

Yeah. Right. So I think a big fear for people is how will they allocate capital as retail investors and actually profit from this new adoption of the technology? And I think that's actually a very big question. mark, right? So, like, you know, the example that keeps coming up, right? When I talk to, you know, Carlos from securitized, for example, says, yeah, what the DTC is doing is really, really interesting by tokenizing, but it's like, it's just changing their plumbing. Yeah, that doesn't

matter outside of the DTC. Yeah. So, you know, how will, will retail, I guess, be able to actually profit from what's being built by all of these institutions utilizing the rails? Yeah. So yes is the answer. But I think it's like not as obvious or as obvious it has. been in the past, which is, so, you know, all of these people, all of these companies, these protocols that launched tokens, people were able to, you know, participate in the growth of those tokens. What was really happening was people were launching, you know, some form of exposure to their protocol, very early stage, much earlier than typically what happened in the equity world. And, you know, that also meant that these things were very volatile and people like to trade

volatility. Now, obviously, we're in the situation where, you know, Clarity Act has been debated. I think they just launched the new text or just released to the public like 35, 40 minutes ago. And, you know, we'll see if that becomes law or not. Obviously, if that becomes law, I think there's a world in which, you know, different conversation. Yeah, different conversation. Everything is tokenized. But if everything is tokenized, one of the, there are many benefits of tokenization.

One of them is that there are different ways of which people can go public and can provide, you know, maybe fractionalized access to different types of investment opportunities earlier stage. And so we're already seeing that somewhat with open bell, which is the product that is coming out of, not securitized, but super state. And they're trying to provide a way for people to tokenize their equity earlier than they might go public otherwise. You're also seeing a lot of different startups try to find ways to tokenize and provide retail access to, you know, different types of alternative asset classes that didn't exist before.

And we're also seeing net new novel financial products be built on top of blockchain rails. that are also providing or building things that have product market fit and revenue. And so hyperliquid and lighter, Venice, there's many, many others that are starting to say, okay, well, we're building kind of net new financial primitives and we're launching tokens around those. And because of that, we're able to do this earlier than we'd be able to potentially IPO. Because IPOs these days and whether or not you trade well as a public company has as much to do as well. Like, can you get index inclusion? Can you get an equity research analyst to cover you?

and that's not going to happen of, you know, companies of the size that I'm talking about for the most part. And so there will be a world where the investable universe is much bigger, but it probably won't look like every technology company that launches a token, and these tokens can hopefully all go up at once. So you mentioned Venice, one of the, it was weeks ago now, but, you know, it kind of resparked the token versus equity debate. Yeah. And I would love to know where you sort of stand on token versus equity debate.

how value should accrue to one or the other, should people have both? Should old tokens be converted to equity in some way, shape, or form at this point? Or should equity be converted to tokens? How is this going to look? Yeah. Listen, I think there's, this is a complicated conversation, and it depends on context of any individual company or protocol. I think very clearly everybody is working within like the parameters that a non-clarity

act world allows them to operate into. I think where there's a lot of very interesting token economic work that people are doing, Venice being one of them, and some of the dexes as well, and in terms of finding ways to provide just value accrual back to that token and back to the holders of that token, and also operate within the governance structure that they need to as companies that are building different types of businesses that require the ability to, you know, enter into contracts with, you know, large service providers and, like, large, you know, some of the

financial companies that we're talking about, et cetera. And so it is, it's complicated. I think we, the perfect world is one where all, everything is tokenized and we can get, you know, tokens to be the, the only source of value accrual. It's not yet the world that we live in, but I think a lot of us are working to try to get us there. As you look forward, what do you think the next whole market. I'm not asking for timing or price. But, you know, as you're kind of handicapping the future, what do you think it looks like versus the previous cycles that we've seen before? First of all, I was one of the like the four-year-cycle dead skies. I'm kind of eating it right now, maybe. We'll see. I guess I was also that way

or I am also so that way. And I don't really think it's not. I keep saying, unless it goes like wildly up in October and just keeps going up, then I'll say I was wrong. Yeah, exactly. But okay, you know, if we get the upside too at the end of it, then sure. But I mean, you know, what do you think the next market looks like. We've obviously, you know, we've had like the ICO cycle and then sort of the pre-sale, I guess, VC cycle. And we've had the defy summers and the metaverse winters and NFTs, right? So, you know, what does it look like? You know, it's hard to, to know, and, you know, I wish I was able to see the future. I'm not asking you to see the future, but I know that you have a premise because you're actually allocating capital based on what you think will happen in the future.

Yeah. I mean, I have an expectation that there's two things that are happening. So there's the retail side and the institutional side we've kind of talked about. On the retail side, you know, people want volatility. They want, you know, potential for like large movements. You know, we have, you know, companies like Micron on the equity side who are 100 vol, even though a trillion-dollar companies, right? Like that type of volatility within the equity market means that we, the traders, the prosumers who are often in crypto, have found interesting things to do in the equity markets,

which were previously less volatile. I have an expectation that volatility moves from one asset class to the other, right? And so the volatility in the equity market will probably dampen at some point, especially as we start to get a little bit more clarity on how the AI market is going to. And there's just so much uncertainty in the AI market that's driving a lot of this volatility. As that dampens, we're going to see those traders move back to crypto and other high-vol assets as well. Prediction markets have obviously been a big part of this story as well, because people have been very excited about, you know, this new primitive and how they can engage in different types of exposure to different types of trades.

And so we'll continue to see that ebb and flow. I think, you know, Bitcoin is sort of its own thing. Ethereum is sort of its own thing. And, you know, I expect that, you know, whatever the time horizon is, that Bitcoin is much higher in the future than it is today. And then I think that when volatility comes back on the retail side, there is going to be the focus on like, or people are going to be more sophisticated around. Does this token have good token economics? Is it a thing that is going to accrue value? Is the revenue within this protocol?

Does it have product market fit? That sophistication is much higher than it was in 2021 when there was like all this fomo, right? Betting on an idea that maybe it may not be built and was already worth billions of dollars. Yeah, in some cases, the fact that we're getting what we wanted, it was bad for, you know, and for token prices. Because if you see, we're also doing a lot on the more institutional infrastructure side and things like that. But I have an expectation that that institutional infrastructure also means that more retail applications will be built that will be net new and novel.

And so you'll have more things that people can trade, that they can interact with. I do think there will be continued ability to do like novel earlier stage projects on blockchains and that will include tokens that, you know, aren't necessarily just stable coins and neopicking like a lot of people say. And so if that happens this year, if that happens next year, I think a lot of that depends on what happens in the public markets and what happens with AI, to be honest. Yeah, you made an interesting point about volatility. I think one of the just quiet reasons that crypto has been so uninteresting is that we actually took what you could do in crypto and allowed you to do it on every other asset. Yeah.

There used to be that, you know, if you went to a crypto exchange, you had to find some crypto asset or some all coin that was going to have volatility or, you know, that you'd catch the pump. now you can just go on Hyperliquid and the same people who would have been trading crypto or trading silver instead, right? Or pre-IPO SpaceX. Yeah, I think it's recently, you know, the hip three

markets that on Hyperliquid which are, you know, the rural asset markets was as much as 40% of daily trading volume, right? And it's crazy. And so because people are looking for volatility and they're looking for places to find an edge. And, you know, in these markets right now where there just hasn't been

as much volume, especially in all coins, there's just been less interest. But these things ebb and flow, like there's, you know, it's absolutes are for, what is the, you know, absolutes are for, I forget the exact same. Yeah, yeah. But, you know, I think we'll see a, that ebb come back. And when that date is, I don't know.

Yeah, I guess the big question a lot of people's minds is what happens to the things they're holding now. You know, like these all coins that just haven't moved in five years. Yeah. You know, is there somebody, it's interesting, I think we have the Franklin Templeton branding back here, but they bought coin fund or however that was structured. And it's a liquid fund,

and they're going to try, I would assume, try to raise billions of dollars to buy a bunch of liquid tokens. So there's somebody out there who's, I've got to imagine they're not the only ones who are interested in buying tokens that are on the market right now. Absolutely. Well,

and, you know, I've even talked to, you know, some of the big, you know, kind of like multi-stage hedge funds who do both public and private,

maybe crossover funds, who you would be surprised, some of the names that owned some of the tokens that we were just talking about the lighters and hyperliquids of the world. And you would have expected that maybe they own Bitcoin or Ethereum and Solana, things like that, but also owning

a lot of the applications. So we're seeing people buy these things, but I do believe that there's still, it's still very hard for those types of investors to stomach some of the volatility. But also as they get used to the volatility on the equity side, I expect over time with more, you know,

more agentic trading, more automated trading, that the risk management will get better. And so people will give a little bit more comfortable with it. But this asset class is one where, you know, I used to work at a big hedge fund called Golden Tree. And, you know, we were one of the first ones in the 2020 and 2020 and 2021 phase to come into crypto. But when things start making money for people,

everyone takes notice. And, you know, there's the infrastructure is now there for a lot of these big liquid managers to come back into the space when they see opportunity. Yeah. I mean, you kind of made this joke before you care for what you wish for. We got what we wished for and maybe we didn't want it. I mean, institutional adoption was all we ever talked about. And now, you know, institutions are getting adopted in their own way and maybe not ours.

Yeah, that's right. Well, I remember Larry Fink was it was 2023 who was saying everything's going to be tokenized. And if you remember, like all of the all coins went up with, you know, Bitcoin and everything else when he did that. And then a lot of things are now being tokenized. and we're finding out that, you know, the value occurs in different places. Well, I mean, if we do believe that there will be value in all coins, then we should actually beyond the fact that our bags are underwater, sheer the fact that we'll find a reasonable way to value them and invest in them

and understand why they may move up or down beyond just speculation gambling or like a tweet from a KOL or something, right? 100%. And I'm of the opinion that if more and more capital comes on chain, whether that's through stable coins, through these neobanks, through a lot of the more institutional interests, if there is just an ability to be on chain or not have the same friction that you would have before,

you know, things like the lighter integration into Robin Hood wallet and things like the hyperliquid builder codes. And we start to see these things get pushed out to more and more everyday users. That is going to be good for the whole ecosystem and it's going to be good for, you know, prices within that. Now, I do believe we're in a world, I'm not sure we'll ever be in a world again

where all things go up together. I do think there's going to be a lot more dispersion. Selective all season. But also, like, that's the way markets should work, right? Like, then there's efficient markets. Interesting, I think somebody, I'm trying to remember who it was, but I did one of these interviews and pointed out that we have the most dispersion historically we've ever had in the stock market, actually.

So, like, it actually, if you're a good stock picker right now, like, yeah, markets may broadly be up, but they're huge winners and huge losers, and it's not everything goes up at the same time as much as the headlines seem to indicate. and maybe if that comes to crypto, that becomes a very compelling reason for people to take notice again. 100%. Anything else on your mind before I let you go? I always like to say when because it does feel like there's just so much despair almost in the markets. And when you're on the ground and you're talking to the people who are building here,

like it's hard to be bearish to be honest over the long run, right? Whatever happens in the short run, you know, if you're long-term builder in this space, you're a long-term investor in this space, it's very clear. to me that we're in for a good X number of years, whether or not that means for the rest of the year, who knows? Yeah, I mean, I think we've gone from despair to apathy now maybe, you know, like for retail, but I think that there's actually more excitement to build in the bare market by anyone who is because they're not distracted by prices and media narratives.

Absolutely. All right, man. Appreciate it. Thanks so much. We finally got to do this. Thank you. Today's video is sponsored by Securitize. You've heard the word tokenization, putting assets like funds, bonds, bonds, treasuries,

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