Unchained - Why Pre-IPO Perps Like SpaceX on Hyperliquid Are Seeing an Upswing

Episode Date: May 24, 2026

Pre-IPO trading is hot ahead of three big IPOs. Perp volume on Hyperliquid went from $3M to $44M in three months, and SpaceX perps is just the beginning, says Dio Casares of Patagon. ======================================================== Thank you to our sponsor! ⁠⁠⁠⁠Coinbase One⁠⁠⁠⁠: Get 20% off the first year of your Coinbase One annual plan at ⁠⁠⁠⁠coinbase.com/unchained⁠⁠⁠⁠. ======================================================== Pre-IPO perp volume on Hyperliquid grew from $3 million to $44 million in roughly three months. Anthropic and OpenAI voided secondary shares, sending shockwaves through the pre-IPO marketes. Robinhood launched trust-style tokenized offerings into a gray area. And three trillion-dollar IPOs — SpaceX, Anthropic, and OpenAI — are converging in the same window. Dio Casares, founder and CEO of Patagon, a private neobank that has facilitated deals in Anthropic, xAI, Circle, and Kraken, explains the structural difference between derivatives and tokenized spot, why second and third-layer SPV waterfalls are legal hot potato, who actually holds the cleanest title, and where the competition for private market liquidity goes next. Host: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Laura Shin⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, Host / Unchained Guests: ⁠Dio Casares - Founder & CEO, Patagon Learn more about your ad choices. Visit megaphone.fm/adchoices

Everyone, welcome to Unchained. You're a no-hype resource for all things crypto. I'm your host, Laura Shen. Thanks for joining this live stream. Today's guest is Dio Cossaris, founder and CEO of Patagon. Welcome, Dio. Thanks for having me, Laura. This week, well, really, it's actually the last couple weeks.

We've seen a lot of activity in the pre-IPO markets, especially on chain. So this week, there was a huge debut on SpaceX, sorry, on hyperluquent, of pre-IPO. perps for SpaceX. And around the same time, we saw Polymarket announced a new category of event contracts that allow users to bet on things like unicorn valuations, IPO dates, and secondary market pricing. And that deal was with NASDAQ private market. And last week, obviously, there was the huge brouhaha about Anthropic and OpenAI voiding a bunch of secondary shares. So let's maybe just talk about, you know, all this activity. I do know that, like, just for hyperliquid alone, some of this pre-IPO activity in February only totaled to like $3 million. And as of a couple

days ago, it's already at $44 million. That's according to Allian Research. So talk a little bit about why you think we're seeing this activity bubble up right now. Yeah. I mean, I think a big thing is very strategic timing. A good way for a crypto audience to understand some of the pre-aids. IPO perps is almost like pre-markets in crypto in the sense that if a lot of people remember, Hyperliquid went pretty aggressive on a lot of alt-coin premarkets. And so they started to get a lot of volume on those markets. They started to be where most of the volume for these premarkets were happening. And then when those tokens went live, normally the pricing was pretty on par with what the price

ended up opening up at. And they ended up holding on to, by then, I mean, hyperliquid. ended up holding onto most of the volume once these became live normal perps with a normal Oracle. And so what we've seen with Cerebrus and what we've seen now with SpaceX is these pre-IPO perps launching just a little bit before the IPO is planned. Like I think SpaceX is the 17th of next month. So there's like three, four weeks left.

And because they're launching right before, they can get a lot more. volume and a lot more people are willing to participate because you can kind of think of them as student to settle futures rather than what Ventures was doing whereas more long-dated and unclear when those perpetual futures would actually settle. And so, you know, in my initial question, I kind of referenced a bunch of different types of, you know, this activity. So as I mentioned, it was the space X pre-IPO perps, this Polymarket News, the Anthropic and Open AI, that was happening both off-chain and on-chain. And these are all, you know, kind of like, you could say, either different areas of the market or different

phases of that pre-IPO stage. So how would you kind of characterize like what each of these news events is about in terms of like, you know, this whole space? I mean, SpaceX, a lot of the a lot of the reason why Open AI and Anthropic came out and said, you know, we're not going to respect these transactions is two pronged.

One, they want to create something almost genuine fear for people to not want to invest into secondaries, because all a secondary is, is a transaction where someone's buying stock

where the company or employees are not making money. And then all of these, all of these AI companies, for lack of a better term, are cash insincerators. They take in a lot of cash and they're investing it and they're burning billions and billions of dollars. So anything that gets away, in the way of such a cash incinerator, especially right before they're all about to enter pretty competitive IPOs. I think it's SpaceX first and then Anthropic and then Open AI.

They're all trying to get as much capital as possible. And for them, they see it a very important step to do that being restricting secondaries before their upcoming IPOs to try and be able to make all that supply go into their primary rounds. And the other thing is a liability thing, which is normally when a company takes a transaction as being credible or approves a transaction, they're also responsible for enforcing that transaction. So basically on the ledger of the company's shares, making sure that whoever bought the shares actually gets the shares on IPO or before. And you can imagine you have hundreds, maybe thousands of these SPVs and these companies that probably are going to have lawsuits or have very convoluted structures. And there's going to be a bunch of waterfall kind of issues as these SPVs start to close for these IPOs.

that these companies just don't want to be anywhere near for liability and also for just headache reasons. You don't want to have to be dealing with a thousand different cases. So they're just going out and very loudly saying, hey, this is not our problem. If you're not an approved block, we can't really help you. And saying that very loudly now before there's any issues on the IPO. So it's both them trying to maximize how much cash they can get

and trying to minimize their liability. if that makes sense. All right. So in a moment, we're going to talk a little bit more about these types of problems that exist in this market and how they might be solved by going on chain. But first, we're going to take a quick word for the sponsors who make this show possible. A 3% top off on my entire portfolio? Uh, yes. Who is saying no to that? That's free money. I don't care what's in your portfolio. That's a yes. If you've been looking for an excuse to consolidate your assets, this is it. Until May 31st, Coinbase is giving a straight. 3% Bitcoin boost on any crypto or cash deposits all month. Coinbase 1 is the ultimate membership to make the most of your money, which, as you know, is how I optimize my finances.

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assets on Coinbase. Back to my conversation with Zio. So you kind of went into this a little bit before the break, but just line out, kind of line up what all the different problems are between, you know, both for buyers and sellers that they're trying to solve by going on chain. So I mean, going on chain, you can kind of separate it into two markets. You have the derivatives market and then you have the spot market. that the derivatives market is great for a bunch of reasons.

It's primarily, as is the nature of most derivatives, a hedge. So a lot of the people that I know that are using this market are using it as a way to hedge positions that they have in spot or that they've invested in directly. I think that the derivatives market in crypto makes a lot more sense than the spot market, and primarily that's because of U.S. regulations. In the U.S., if all of these private stocks,

you're supposed to have a holding period of six months. There's arguably ways around that, but it's roughly six months. If you don't have a system to force that holding period to be six months, you can break the regulation exemption that those stocks have. You can be considered in breach and there's fines and there's a bunch of other stuff. So as soon as you tokenize something,

as soon as you tokenize an interest or anything that represents ownership in one of these companies, it's quite easy for a US regulator to say that that's in breach of that regulation. And so I think that's going to be a massive pushback that a lot of the tokenized offerings are going to have. And also just that a lot of other,

back to the conversation about, it's actually not necessarily in these companies' interests for there to be a lot of volume on the spot market because then that can compete with their primary rounds. They don't want this price discovery to be happening in this way. So they could be more adversely selected when these companies are looking to raise capital, they could be like, hey, we know you're going to tokenize this, therefore we're not going to work with you. Versus on the derivative side, it's a lot easier because you can just have a family office or someone that invested individually can hedge their exposure or if they want to, I guess, increase their

exposure. And that's something where you don't have this keyman risk, whereas these tokenized offerings, you know, if they mess up the SPV or if there's any kind of legal issue, or if they set up the fund improperly, it could have catastrophic downstream effects for everyone, whereas the derivatives, there's some risks. Like, you can. get ADLed or there could be a price look. But there's more of a kind of, there's not a keyman risk of, you know, someone messed up a contract and now no one can get their money, if that makes sense. So I'm much more bullish on the perks side. Yeah, it's like much more just a market risk, which I think people are willing to accept. Whereas in the other kind of situation, it's something

where it's like somebody screwed up and there's going to be hell to pay, which is, yeah, not acceptable to a lot of people. Yeah. So I saw some criticism that the reason that there are these problems also in this kind of pre-IPO area is that these unicorns have been, you know, first of all, just staying private longer, as everybody has talked about for a long time. But in a way, they're also almost like pretending to be private because they are letting a lot of sort of, you know, like, gray market activity. kind of flourish around them. And so you end up in these situations where a lot more people have some form of ownership than if it was just like a lot stricter. And so it's almost like they're practically public in a sense. Do you agree with that take? Or what are your thoughts on that?

I would agree in the sense that there's record participation in these companies in terms of the capital that they're raising. If you were to separate this year, amount of people that have invested in these companies before the IPO, it's thousands and thousands and thousands and thousands of people, which is very atypical for private firms. What I would say is that they, to my knowledge, at least, have not really promoted secondary markets in the sense of people being able to buy and sell once they've invested. They have tried to be very explicit to people that, hey, if you're investing, you should be holding until the IPO or a similar liquidity event. So I don't think it's entirely fair to say that they're just public market

companies masquerading as private companies. It is still much more difficult to buy these stocks, and there's a lot of benefits that they get from going public, mainly a decrease in fraud. but it is true that they've had just absolute record numbers of investors and capital going into these companies for such an early stage. I think that's very true. And so, you know, you mentioned earlier that you felt like perps are really kind of superior in a certain way. But there's a reason that people are willing to kind of engage in, you know, or at least

attempt to invest before, you know, it reaches that stage. So talk a little bit about that period, like what all the different options are and kind of like what the various risks are that come with the different types of either vehicles or like types of exposure that you can get. Sure. I mean, the obvious reason you would want to get involved earlier is because the price is probably better. If we were having this conversation about Anthropic like two years ago, the valuation would have been like $80 billion, which given their current round is a little bit over 10x, not including obviously dilution.

So there's obviously a reason to want to invest and get a better multiple. The best way that you can invest in most of these companies that are at your stage is finding someone that has access to their primary round and is doing an SPV or co-investment. into these companies. Co-investment is different from an SPV in the sense that some very large funds you do co-investment. So they'll invest, as an example, a billion dollars. And then from their fund side, as an example, so be like a large VC.

And then they'll let their LPs invests, say, $100 million directly into the company if they want to. That's probably the cleanest way possible to invest in a lot of these companies. If you can't do that, it's probably best to find someone that has an SPV or someone that has direct access on these other stage companies. As soon as you get to second layer and third layer, you're just kind of playing a potentially dangerous game of legal hot potato with these shares that I think most people would want to avoid. Yeah, talk about that.

What are the problems that can arise in those situations? There's a bunch of very in the weeds issues. For example, anthropic and open AI right now are very loudly saying that they do not consider these transactions to be legitimate. So say you have a waterfall and you have whoever has the shares but is committed to give them up to an SPV or the SVV itself that. holds the shares and then it owes the second layer and then owes the third layer. If you have to, if that person has to send those shares to a bank or a brokerage account, in general, especially at the start when an IPO happens, the bank or the brokerage compliance department will ask, hey, you know, what kind of transaction is this?

Is it a sale? Is it a gift? Is it a transfer? If it's a sale, please show me the docs. and there's a real risk that a lot of these banks and brokers could just be like, hey, we don't know if this transaction is valid and therefore we can't allow you to sell these shares. Most of the time you'll eventually, because DTCC has a type of share called restricted shares versus non-restricted shares, a lot of the larger brokerages and banks will still ask those

regardless, but some of the medium-sized firms are like, okay, these aren't restricted shares. I don't really have a risk. I'll let you do it. But if any of these SPVs have, you know, their main bank account set up with say JPMorgan and JPMorgan's like, hey, we can't sell these shares for you, suddenly they're in a race against time to set up a new account, which isn't super easy and then transfer it from their account to this other brokerage account, which looks terrible now from an AML perspective, because why did you? you have it in that account and now you're sending it to us. Clearly there was a problem there.

And so that's a procedural problem that you can have. You could also just have someone be like, hey, you know, I agreed to sell you this and give it to you. But actually, these are void and I'm just going to refund you, which probably will obviously lead to litigation in most of those cases. And I am of the opinion that they probably lose, but you still have to sue the person. So there's a lot of these different risks that could happen based on how. these vehicles are structured.

Yeah. It matters a lot. Even in that last example, if they offer to refund you, that's assuming they still have the money. Yeah. There's also obviously like the tail risk of like complete fraud. Like someone just showed you absolutely fake documents and, you know, went on a vendor with the money.

And there's not really much you can do there. Yeah. And just also explain about, you know, Robin Hood when they tokenize shares. So that was for OpenAI and SpaceX. And obviously we saw that like right after Open AI kind of disavowed that, but I'm sure the setup is probably okay. But like just explain sort of where that fits. Yeah. My understanding of those offerings are their trust style offerings, which falls into a kind of legal gray area in terms of if they break securities laws, and if companies like OpenAI can actually stop companies like Robin Hood offering them,

whatever the case, those in general haven't gotten a crazy amount of interest, mainly because they're also not liquid in the sense that these trust companies, basically you can put a bunch of shares into the trust, and now you can buy and sell these tokens, but you can't redeem for a certain amount of shares until there's a major liquidity event. And so for a smaller investor, that might be a better way of investing,

but for a larger investor, you have to really hope that the market value, the market actually believes that these tokens are valuable, which, as we saw after a lot of these announcements, a lot of the market suddenly thought that these tokens weren't as valuable as they had a few hours before. So it's a pretty big risk to take. And then you mentioned briefly the FTX bankruptcy,

which obviously owned some shares of Anthropic. Where does that type of situation fall? I imagine that's sort of an outlier and like really uncommon, but I'd be interested to hear just what sort of place that holds in this universe. Yeah, I mean, bankruptcy court is, the most like for lack of a better term mob rule in terms of it's not really bankruptcy law as much as what the court and a lot of other people involved in the process consider to be fair so that block of anthropic shares as well as a lot of other shares assets that ftx had were generally sold without any encumbrance so that means you know the right to first uh right to first uh right to first refuse on the shares was completely waived by anthropic. Transfer restrictions were waived.

All of these other things were waived. There's an argument to be made that obviously that doesn't extend past that initial transaction. And it's an argument to be made, but it would probably be quite rough because that would create a precedent potentially of bankruptcy estates not getting treated as having full value when they're selling assets of the future, which would obviously be bad for any kind of future bankruptcies. And so it's probably if you have a block in the Anthropic related FTX claims, basically

the stock that FTX bought in Anthropic, you're probably the safest out of most people, outside of direct investors that are approved by the company, just because there's kind of this different legal status hanging over it. So tell us more about this world in terms of the different players. I understand some of them are not necessarily crypto-related, but then there are others that are on-chain. So sort of give us the spectrum, and I'm also sure some of them are shadier than others. Yeah, I mean, SETTER is kind of one of the quieter, larger secondary brokers.

They do everything from fund positions. So say you're invested in like a paradigm fund and you want to sell your position before the fund returns their capital. You can sell that to direct allocations into these companies. They've managed, according to their website, 400 billion these transactions, which is just insane. They're clearly one of the larger ones. Forge and Hive are some of the most invisible

in that a lot of people know about them. They let you set up an account quite easily. They have a bunch of data. And they do a decent amount of volume, but they're actually not super massive. There's a bunch of then smaller or medium-sized firms. This is all on the spot side. On the perp side, you have trade,

XYZ, obviously, which is HIP3. You have Ventuals, which is kind of the OG protocol that is also HIP3. You have new ones, like a buddy of mine's doing this one called Entropy. That's also going to be HIP3. You kind of have a general concentration around hyperliquid for these markets. On the tokenized side, I think there's a couple different players. A lot of them are on the Solana ecosystem, more so than the ETH ecosystem. And that model, I don't know the names, the companies off the top of my head, but that model for them tends to be a 20% one-time fee, which is quite high.

And then a 20% performance fee on these tokens versus, obviously, there's trading fees, which is how the derivatives markets make their money. So it's kind of interesting different business models. The spot ones kind of just flip their shares to retail versus the derivatives companies very much just get a fee for facilitating these kinds of transactions. Yeah, it's probably, I guess, targeting a different demographic. And out of curiosity, why do you think that activity is happening on Solana versus Ethereum? I think Solano is a lot more retail and

for whatever reason they're willing to experiment a lot more there is also a pretty decent crypto and AI overlap I mean to an extent even I am an example of that and so I think there's a lot of people that were willing to take a lot of risk

and had a lot of capital and we're used to doing it on Solana that were willing to invest into these kinds of projects also on Solana instead of having to, you know, set up a bank account, do all of these other steps or like meet these people in kind of smoky cigar rooms to have to get direct allocations. So it was kind of people going to where there was capital. Huh. Okay. So tell us a little bit about your business because obviously you're very involved here. So what does what does Patagon do in the secondary? Yeah, so we're kind of a private neobank. We primarily help people get private, get into private deals. So we've done Anthropic before. We've done XAI. We've done Cohere. We did Circle before the IPO. We've done Krak in. We've done fluid stock. We've done a bunch of different companies. We generally were an exempt advisor. So,

We set these up as funds. We help with the filings and everything, but we don't have to be a registered investment advisor yet because our AUM has not yet hit directly $150 million, which means it's a little bit less of a pain to work with us compared to some people that are RIAs. We're expanding that business now also until allowing people to invest in commodity deals.

So say if you have a directional bet on, Argentine copper mining as an example. You should be able to invest in a project. That's legit. That's kind of been vetted, which is a big thing about our platform. We take care to try and vet almost all of these deals that we do because it's kind of our reputation on the line if these don't go well.

And we've done that with tricky deals. Like Circle, for example, was a very tricky deal because we did it right before the IPO. And that was a hard thing to pull off. And so we're trying to do that also with more tangible assets. And then we're also trying to get more into offering bank accounts, crypto custody and these other services for people. But our business is basically we can help people get into some of these deals.

And then these deals are structured as a fund. And we take fund fees, which vary from deal to deal, depending on the size and depending on how difficult it is to get into these companies. Okay, so your business actually doesn't have an on-chain component at the moment. No, I mean, we're looking at the perp, the kind of private market perp side to see if we should go to some of our clients and say, hey, if you're thinking about hedging, you know, pre-IPO, which is a little bit of a gray area, you should consider doing it via perp. versus doing it via like an IBKR setup. And we've also been, to be quite frank, getting questions about it from clients of like,

hey, should I hedge my exposure via perps or via like an IBKR kind of short? That's the extent to which we see this. We're maybe going to help some of the entropy guys with their markets. They're going to try and offer some pre-markets a little bit earlier. than what TradeXYZ is doing is my understanding, but it's not a core part of our business for sure. Because we don't want to antagonize some of the companies

that we're on the cap table of. And I think launching tokenized versions of their stock or pre-IPO markets, especially very early pre-IPO markets, is a very easy way to get them quite annoyed at you. And to get on, like, people forget this, but Anthropic had a list of people not to touch, basically. And that's a great way for us to get on equivalent lists.

And so we're not going to. Yeah. Yeah, I mean, it just goes back to that control issue that we talked about. It's sort of like if you want to stay in their good graces, then you have to kind of play by their rules. But yeah, it's not as favorable, I guess, for the buyer who, yeah, just might prefer something more liquid. Good. All right. So as we mentioned at the beginning of the show, this area is only just getting started in terms of competition. It's very clear. Some of those numbers that I gave, you know, they're small. So I'm just curious, you know, you probably know about new things that are in the work. So how do you expect that this space of like private market activity, especially for the parts of it that go on chain? Like how do you expect that to evolve?

We are kind of in a perfect moment in time in the sense that there's a lot of positive tailwinds for hyperliquid in general and for these pre-IPO markets. The fact that so many world and market changing actions happen on weekends right now has just been a massive goom for a lot of these RWA perps that can trade 24-7. and the same thing, these pre-IPO perps, when they convert, become just normal RWA perps. And so the same way that Hyperliquid kind of had pre-market perps as loss leaders, i.e. a kind of product they offered, where they were willing to lose money on it,

as long as it meant that long term they'd make money by controlling that market. I think you could see that a lot more. I'm not sure if the pre-APO market will be, we have a historic amount of IPOs happening this year, right? We have SpaceX, Anthropic, and Open AI all trying to target trillion plus valuations. That's never happened before. Not to mention, there's a bunch of other random companies that I could also mention. So there's just a really good time right now for pre-IPO purpose.

to start to pick up a lot more traction. And I think as the SpaceX, I mean, Cerebrus was a good example, but if the SpaceX perp settles as well, Anthropic and Open AI, perp volume will probably only increase. And you'll see a fight from a lot of the kind of exchange providers to try and cover these pre-IPO markets

in order to then dominate the volume once they convert to normal markets, which I think will be very interesting. All right. Well, Dio, it's been so fun chatting with you about this space and learning about it. And yeah, I feel like it's going to get crazier. I feel like it's like maybe going to end up being like the deaths of last year or something. I don't know.

Yeah. I mean, there's probably going to be some crazy market movements for sure. Yeah, yeah. We'll have to see, especially I don't know, just with the way the market is like just generally the stock market now. I'm a little bit like, I don't know. There's something about it that makes me nervous. But anyway, all right, well, thank you so much for sharing all your insight and information. And yeah, thanks to everyone for joining this live stream.

We'll catch you next week. Thanks for having me. Nothing you hear on Unchained is investment advice. This show is for informational and entertainment purposes only. And my guest and I may hold assets discussed on the show. For more disclosures, visit Unchained Crypto.com. Thank you.