A Comprehensive Analysis of On-Chain Pre-IPO: Why is the Pricing Power of SpaceX and OpenAI Moving On-Chain?

Organized & Compiled: TechFlow

Guest:Dio Casares, Founder of Patagon

Host:Laura Shin

Podcast Source:Unchaind

Original Title:Why SpaceX, OpenAI and Anthropic Now Trade Onchain

Broadcast Date:May 22, 2026

Key Takeaways

In the latest episode, Dio Casares and Laura Shin delve into how pre-IPO price discovery is gradually migrating to the blockchain. From the recently launched SpaceX pre-IPO perpetual contract on Hyperliquid to secondary market trading of Anthropic and OpenAI shares, they deeply analyze this trend. They also discuss the new partnership between Nasdaq Private Market and Polymarket and its potential impact on the future of private equity.

Highlights Summary

Why the On-Chain Pre-IPO Market is Suddenly Heating Up

• "A good way for the crypto audience to understand pre-IPO perpetuals is to think of them as the crypto version of pre-market. Many people might recall that Hyperliquid used to be very aggressive with many altcoin pre-markets, which started attracting significant volume and gradually became where most pre-market trading occurred."
• "These pre-IPO perpetuals are launched shortly before a planned IPO or key event... Because they are launched so close to the event itself, they attract more volume, and more people are willing to participate. You can think of it as a future that is about to settle, as opposed to products like Ventuals, which have longer durations and it's unclear when these perpetual futures will ultimately settle."

Why OpenAI and Anthropic Deny Secondary Trading

• "First, they want to create genuine fear to discourage people from investing in the secondary market. Because the nature of secondary market trading is that someone is buying shares, but the company or its employees are not receiving capital from it. And these AI companies, to put it bluntly, are high capital consumers. They absorb massive amounts of cash and then invest and burn through tens of billions of dollars."
• "Anything that hinders these high capital consumption companies (so-called 'cash incinerators') from raising capital, especially right before they enter an intensely competitive IPO phase, is seen as a major problem... They are all trying to absorb as much capital as possible. Therefore, for them, restricting the secondary market just before an IPO is an important step because it can channel more supply and demand into their own primary funding rounds."
• "The second reason is liability. Usually, when a company validates or approves a transaction, it is also responsible for executing that transaction... When these SPVs start unwinding and closing around the IPO, a host of waterfall issues arise. For these companies, whether due to legal liability or simply not wanting the hassle, they want to stay far away from this stuff. Nobody wants to deal with 1000 different cases."

What Problems Does On-Chain Implementation Solve?

• "In crypto, derivatives markets make more sense than spot markets, mainly because of US regulations. In the US, these private shares typically have a roughly 6-month holding period... If you don't have a system to enforce this 6-month holding period, it could jeopardize the regulatory exemptions these shares rely on, leading to fines and a host of other issues."
• "High spot market trading volume may not necessarily be in these companies' best interests because it competes with their primary rounds. They don't want price discovery happening this way, as it could lead to adverse selection when they raise capital. A company might say: 'We know you're going to tokenize this, so we won't work with you.'"
• "With tokenized products, if an SPV makes a mistake, or if any legal issues arise, or if the fund structure is problematic, the fallout can be catastrophic. Derivatives also have risks, of course, like ADL events or price spikes, but it's more of a market risk rather than someone messing up a contract and everyone losing their money. For this reason, I am more bullish on the perp side."

Are Private Giants Already Trading Like Public Companies?

• "To some extent, I agree: these companies do have record levels of participation. If you break down the capital invested pre-IPO into these companies, the participants could number in the thousands, tens of thousands. For private companies, that's not typical."
• "But to my knowledge, they aren't actively promoting a secondary market, meaning they don't encourage people to buy and sell after investing. They've been trying to be very clear with investors: 'If you invest, you should hold until an IPO or a similar liquidity event.'"

Methods and Risks of Getting In Before the IPO

• "These are late-stage companies. Once you get into the second, third layers of structure, you're playing a dangerous legal game of 'hot potato' with these shares, which most people would probably want to avoid."
• "There is a real risk here: many banks and brokers might say, 'We don't know if this transaction is valid, so we cannot allow you to sell these shares.'... If the primary bank account for an SPV is at JP Morgan, and JP Morgan says 'We cannot help you sell these shares,' they suddenly find themselves in a race against time: setting up a new account, which isn't easy; then transferring the shares from the original account to another broker's account."
• "There's also a scenario where someone might say: 'I did agree to sell and deliver these to you, but now these transactions have been deemed invalid, so I will just refund your money.' That would most likely lead to litigation. That person might eventually lose, but you still have to sue them. So, depending on the instrument and structure, there are many different risks."

Robinhood, FTX, and the Legal Boundaries of Different Structures

• "As for whether they violate securities laws and whether a company like OpenAI can actually stop companies like Robinhood from offering these products, that's still a legal grey area. Regardless, these products haven't gained particularly widespread attention. The main reason is that these products aren't truly liquid assets."
• "The Anthropic shares held by FTX, and many other shares and assets held by FTX, were typically sold without any encumbrances. That is to say, Anthropic's right of first refusal (ROFR) on those shares was completely waived, transfer restrictions were waived, and other restrictions were also removed."
• "If you hold Anthropic shares related to FTX claims, meaning the Anthropic stock that FTX purchased, you might be among the safest holders besides direct investors approved by the company, because it carries a different legal status."

The Competitive Landscape of the Private Secondary Market

• "On the perpetual side, there's Trade.xyz, which is HIP-3; there's Ventuals, which was an earlier protocol, also HIP-3; and there are new projects, like Entropy, which a friend of mine is working on, which will also be HIP-3. They will offer some pre-markets a bit earlier than Trade.xyz. You'll see these markets generally aggregating around Hyperliquid."
• "I think Solana is more retail-focused, and for some reason, people are more willing to experiment there. There's also significant overlap between crypto and AI... There are many people willing to take high risks and who have capital, and they are already used to operating on Solana. They tend to invest in these kinds of projects without needing to open bank accounts, go through cumbersome procedures, or gain direct share allocations through personal connections, as in traditional finance."

Patagon's Positioning and On-Chain Boundaries

• "We previously looked at perpetuals in the private market, to see if we should suggest to some clients that if they are considering hedging pre-IPO exposure—though it's a bit of a grey area itself—they might consider using perpetuals rather than setups like IBKR... We don't want to anger the companies whose share registries we are on. Launching tokenized versions of their stock or launching pre-IPO markets, especially very early pre-IPO markets, is an easy way to really upset them."

Why Pre-IPO Perpetuals May Continue to Expand

• "Many major events that change the world and markets now happen on weekends, which is a huge boon for many RWA perpetuals that can trade 24/7. The same goes for pre-IPO perpetuals. Once they convert, they become regular RWA perpetuals."
• "I'm not sure how the pre-IPO market will evolve, but this year we have a historically high number of IPOs. SpaceX, Anthropic, and OpenAI are all aiming for valuations above a trillion dollars, which has never happened before... Now is indeed a good time for pre-IPO perpetuals to gain more attention."

Why the On-Chain Pre-IPO Market is Suddenly Heating Up

Host Laura Shin:This week, or more accurately over the past few weeks, there's been a lot of activity in the pre-IPO market, especially on-chain. This week Hyperliquid had a very big new launch, the SpaceX pre-IPO perpetual. Around the same time, Polymarket announced a new type of event contract where users can bet on unicorn valuations, IPO dates, secondary market pricing, etc., and this is in partnership with Nasdaq Private Market. Last week, Anthropic and OpenAI declared a batch of secondary market share transactions void, sparking significant controversy.

According to Allium Research data, the volume for this kind of pre-IPO activity on Hyperliquid was only about $3 million in February, but a few days ago it reached $44 million. What's your take? Why is this activity emerging now?

Dio Casares:

I think a big reason is that the timing is very strategic. A good way for the crypto audience to understand pre-IPO perpetuals is to think of them as the crypto version of pre-market. Many people might recall that Hyperliquid used to be very aggressive with many altcoin pre-markets, which started attracting significant volume and gradually became where most pre-market trading occurred.

After these tokens officially launch, their opening price is usually quite close to the price formed in the pre-market. And after they become regular perpetuals with normal oracles, Hyperliquid retains most of the trading volume.

So what we're seeing with Cerebras and now SpaceX is that these pre-IPO perpetuals are launched shortly before a planned IPO or key event. I think the relevant timeline for SpaceX is around the 17th of next month, so just three or four weeks away. Because they are launched so close to the event itself, they can attract more volume, and more people are willing to participate. You can think of it as a future that is about to settle, as opposed to products like Ventuals, which have longer durations and it's unclear when these perpetual futures will ultimately settle.

Why OpenAI and Anthropic Deny Secondary Trading

Host Laura Shin:In my initial question, I actually mentioned several different types of activities: the SpaceX pre-IPO perpetual, the Polymarket news, and the Anthropic and OpenAI events, with some happening off-chain and some on-chain. They could be considered different areas within this market or different stages in the pre-IPO phase. How would you summarize what these news items represent respectively?

Dio Casares:

The reasons behind OpenAI and Anthropic stepping out and saying "we won't recognize these transactions" are roughly twofold.

First, they want to create genuine fear to discourage people from investing in the secondary market. Because the nature of secondary market trading is that someone is buying shares, but the company or its employees are not receiving capital from it. And these AI companies, to put it bluntly, are high capital consumers. They absorb massive amounts of cash and then invest and burn through tens of billions of dollars.

Anything that hinders these high capital consumption companies (so-called 'cash incinerators') from raising capital, especially right before they enter an intensely competitive IPO phase, is seen as a major problem. Currently, SpaceX is expected to go public first, followed by Anthropic, then OpenAI. These companies are trying to attract as much capital injection as possible. Therefore, for them, restricting the secondary market just before an IPO is an important step because it can channel more supply and demand into their own primary funding rounds.

The second reason is liability. Usually, when a company validates or approves a transaction, it is also responsible for executing that transaction. That is, on the company's cap table, it must ensure that the person who bought the shares actually receives them at or before the IPO.

You can imagine there might be hundreds or even thousands of SPVs (Special Purpose Vehicles) and other entities in the market that could face lawsuits and have very complex structures. When these SPVs start unwinding and closing around the IPO, a host of waterfall issues arise. For these companies, whether due to legal liability or simply not wanting the hassle, they don't want to be near this stuff. Nobody wants to deal with 1000 different cases.

So they are being very vocal now, saying: "This isn't our problem. If you're not in an approved block, we can't help you." They are choosing to make this clear loudly before an IPO causes problems. In summary, it's about maximizing the cash they can get and minimizing their own legal liability.

What Problems Does On-Chain Implementation Solve?

Host Laura Shin:We've already touched a bit on the various problems existing in this market and why some believe on-chain solutions can solve them. Could you specifically list what problems buyers and sellers are trying to solve through on-chain implementation?

Dio Casares:

On-chain implementation can be viewed through two markets: one is the derivatives market, and the other is the spot market. The derivatives market has many advantages. Like most derivatives, it is first and foremost a hedging tool. Many people I know who use this market do so as a way to hedge existing spot positions or direct investment positions they hold.

I believe derivatives markets make more sense than spot markets in crypto, mainly because of US regulations. In the US, these private shares typically have a roughly 6-month holding period. There might be ways around it, but it's roughly 6 months. If you don't have a system to enforce this 6-month holding period, it could jeopardize the regulatory exemptions these shares rely on, leading to fines and a host of other issues.

So once you tokenize something, as long as it represents some ownership interest in these companies, US regulators can easily say this violates relevant rules. I think this is a huge hurdle many tokenized products will face.

Another issue brings us back to the earlier point: high spot market trading volume may not necessarily be in these companies' best interests because it competes with their primary rounds. They don't want price discovery happening this way, as it could lead to adverse selection when they raise capital. A company might say: "We know you're going to tokenize this, so we won't work with you."

In contrast, the derivatives side is easier to handle. For example, a family office or an individual investor can hedge their exposure or, if willing, increase it. Here, you don't have the same key person risk.

But with tokenized products, if an SPV makes a mistake, or if any legal issues arise, or if the fund structure is problematic, the fallout can be catastrophic. Derivatives also have risks, of course, like ADL events or price spikes, but it's more of a market risk rather than someone messing up a contract and everyone losing their money. For this reason, I am more bullish on the perp side.

Host Laura Shin:Right, it's more like market risk. People are willing to accept that. But the other scenario is more like someone messes up, and everyone has to pay the price, which is unacceptable to many.

Are Private Giants Already Trading Like Public Companies?

Host Laura Shin:I've seen criticism that the problems in the pre-IPO space are also related to these unicorns staying private for so long. People have been talking about this phenomenon for a long time, but in a sense, they almost pretend to still be private companies because they allow a lot of gray market activity around them. The result is that more people hold ownership in some form compared to truly strict private companies. So in a way, they are almost de facto public companies already. Do you agree with this view?

Dio Casares:

To some extent, I agree: these companies do have record levels of participation. If you break down the capital invested pre-IPO into these companies, the participants could number in the thousands, tens of thousands. For private companies, that's not typical.

But to my knowledge, they aren't actively promoting a secondary market, meaning they don't encourage people to buy and sell after investing. They've been trying to be very clear with investors: "If you invest, you should hold until an IPO or a similar liquidity event."

So, I don't think it's entirely fair to call them "public companies disguised as private ones." Buying these shares is still much more difficult. Companies also gain many benefits from going public, one very important one being reduced fraud. But it's true, they have attracted a record number of investors and capital at a very early stage, that's accurate.

Methods and Risks of Getting In Before the IPO

Host Laura Shin:You mentioned earlier you think perpetuals are better in some ways. But there must be reasons people are willing to try investing pre-IPO. What are the different choices? What are the respective risks of various investment vehicles or exposures?

Dio Casares:

The most obvious reason is the earlier you get in, the better the price might be. Imagine if we were talking about Anthropic two years ago, its valuation might have been around $8 billion. Looking at its current round, that's a gap of over 10x, not even accounting for dilution.

So, investors certainly have reason to want to get in earlier and achieve better multiples. For these late-stage companies, the best way to invest is to find someone who has access to primary rounds and invest through an SPV or co-investment.

Co-investment is different from an SPV. For example, some very large funds do co-investments: they might invest $1 billion through their own fund first, then allow their LPs to invest another $100 million directly into the company. If you can do that, it's probably the cleanest way to invest in these companies.

If not, the next best is to find someone with an SPV or someone who can participate directly. These are late-stage companies. Once you get into the second, third layers of structure, you're playing a dangerous legal game of "hot potato" with these shares, which most people would probably want to avoid.

Host Laura Shin:What are the issues with that situation?

Dio Casares:

There are many detailed issues here. For example, Anthropic and OpenAI are now being very vocal, saying they don't consider these transactions legitimate or valid.

Imagine you're dealing with a waterfall distribution structure: someone currently holds company shares but has promised to transfer them to an SPV; or the SPV itself holds shares, and it owes a second layer of interests, which in turn owes a third layer. If this person or SPV needs to send shares to a bank or brokerage account, especially right at the start of an IPO, the bank's or broker's compliance department will usually ask: "What type of transaction is this? A sale? A gift? A transfer? If it's a sale, show me the documents."

There's a real risk here: many banks and brokers might say, "We don't know if this transaction is valid, so we cannot allow you to sell these shares."

In most cases, the DTCC (Depository Trust & Clearing Corporation) categorizes shares, mainly into restricted shares and non-restricted shares. Many large brokerages and banks will still raise questions about these shares, but some mid-sized firms might say: "These are not restricted shares, my risk is low, so I can allow you to proceed."

But if an SPV's primary bank account is at JP Morgan, and JP Morgan says "We cannot help you sell these shares," they suddenly find themselves in a race against time: setting up a new account, which isn't easy; then transferring the shares from the original account to another broker's account. From an AML perspective, that's also bad because the new broker will ask: "Why was it there initially, and now you're transferring to us? Clearly something was wrong there."

That's a procedural risk. There's also a scenario where someone might say: "I did agree to sell and deliver these to you, but now these transactions have been deemed invalid, so I will just refund your money." That would most likely lead to litigation. That person might eventually lose, but you still have to sue them. So, depending on the instrument and structure, there are many different risks.

Host Laura Shin:Right, structure is crucial. Even in that last example you gave, where the counterparty is willing to refund, you have to assume they actually still have the money.

Dio Casares:

There's also the tail risk of outright fraud. For instance, if someone shows you completely fake documents and disappears with the money, there's not much you can do at that point.

Robinhood, FTX, and the Legal Boundaries of Different Structures

Host Laura Shin:Also please explain the Robinhood tokenized stock situation. It involves OpenAI and SpaceX, and we saw OpenAI quickly deny it. But I guess its setup is probably okay. Can you explain its place in this landscape?

Dio Casares:

My understanding of these products is that they are more like a trust-style offering. As for whether they violate securities laws and whether a company like OpenAI can actually stop companies like Robinhood from offering these products, that's still a legal grey area.

Regardless, these products haven't gained particularly widespread attention. The main reason is that these products aren't truly liquid assets. The trust can hold a batch of shares, and users can trade tokens representing them, but users cannot redeem the underlying shares corresponding to those tokens until a major liquidity event occurs.

For small investors, this might be a better way to invest because it lowers the barrier. But for large investors, it's riskier because you have to rely entirely on the market's confidence in the token's value. We've seen that after many announcements, the market might suddenly deem these tokens less valuable than hours before. So, this investment approach itself carries significant risk.

Host Laura Shin:FTX obviously holds some Anthropic shares. Where does that situation belong? I imagine it's a relatively rare anomaly, but I'd like to hear where it fits in this world.

Dio Casares:

A bankruptcy court, in a sense, is the closest thing to a "majority rules" arena. Often, it's not just about what the bankruptcy law says, but what the court and others involved in the process consider fair.

The Anthropic shares held by FTX, and many other shares and assets held by FTX, were typically sold without any encumbrances. That is to say, Anthropic's right of first refusal (ROFR) on those shares was completely waived, transfer restrictions were waived, and other restrictions were also removed.

Of course, one could argue that this waiver doesn't necessarily extend to further transactions beyond the initial one. That argument can be made, but it might be difficult to win. Because if you say bankruptcy assets cannot be considered to have full value in future sales, it would set a terrible precedent affecting all future bankruptcy cases.

So, if you hold Anthropic shares related to FTX claims, meaning the Anthropic stock that FTX purchased, you might be among the safest holders besides direct investors approved by the company, because it carries a different legal status.

The Competitive Landscape of the Private Secondary Market

Host Laura Shin:I know some players in the private secondary market aren't necessarily crypto-related, while others are blockchain-based. Could you help us map out the main players in this space? I suspect some participants may operate in more of a "grey area" than others.

Dio Casares:

There are many different types of players in the private secondary market. For example, Setter is one relatively low-profile but very large secondary market broker. Their business is very broad, covering everything from transfers of fund interests to direct allocations of company shares. For instance, if you invested in a Paradigm fund but want to sell your interest before the fund returns capital, you can do that through Setter. According to their website data, they've done an astonishing $400 billion in volume, making them undoubtedly one of the largest players in the field.

Other more well-known players include Forge and Hiive. Many have heard of them because their account opening process is relatively simple, they offer rich market data, and they have decent volume. However, compared to Setter, they are not actually that large.

Besides them, there are many small-to-medium-sized firms operating, active in the spot market, focused on helping investors buy and sell actual shares.

On the perpetual side, there's Trade.xyz, which is HIP-3; there's Ventuals, which was an earlier protocol, also HIP-3; and there are new projects, like Entropy, which a friend of mine is working on, which will also be HIP-3. They will offer some pre-markets a bit earlier than Trade.xyz. You'll see these markets generally aggregating around Hyperliquid.

On the tokenized side, there are also several different players, many in the Solana ecosystem rather than Ethereum. These companies often charge a one-time 20% fee, which is very high for the industry, plus a 20% performance fee on token trades.

In contrast, derivatives markets primarily make money through trading fees. So there are some interestingly different business models here: spot players are more like flipping shares to retail, while derivatives companies are more like facilitating these trades and collecting fees.

Host Laura Shin:It sounds like they might be targeting different audiences. Why do you think more of this activity is happening on Solana rather than Ethereum?

Dio Casares:

I think Solana is more retail-focused, and for some reason, people are more willing to experiment there. There's also significant overlap between crypto and AI, to some extent I'm an example myself.

So, there are many people willing to take high risks and who have capital, and they are already used to operating on Solana. They tend to invest in these kinds of projects without needing to open bank accounts, go through cumbersome procedures, or gain direct share allocations through personal connections, as in traditional finance. Ultimately, projects go where the capital is.

Patagon's Positioning and On-Chain Boundaries

Host Laura Shin:Let's talk about your business. You're obviously very involved in this space. What exactly does Patagon do in the secondary market?

Dio Casares:

We're a bit like a new kind of private bank. We mainly help people get into private deals. We've previously done Anthropic, xAI, Cohere, also Circle pre-IPO, Kraken, Fluidstack, and many different companies.

Generally, we are an exempt adviser. We structure these deals into funds and help with filings, etc. But we don't need to be a registered investment adviser yet because our AUM hasn't directly reached $150 million. That means working with us involves less hassle than working with some RIAs.

We're now expanding this business to allow people to invest in commodity-type trades. For example, if you have a directional view on an Argentine copper mine, you should be able to invest in a real, compliant project embedded locally. That's also a key point of our platform. We try to vet almost every deal, because if these deals go wrong, it's our reputation at risk.

We've also been involved in some complex deals, like the Circle pre-IPO investment. That deal was very tricky because we got in very close to the IPO.

So, we now want to extend this capability to more tangible assets. At the same time, we're also trying to offer services like bank accounts, crypto custody, etc. Our business is roughly about helping people get into these deals, structuring them into funds, and charging different fund fees based on deal size and the difficulty of accessing these companies.

Host Laura Shin:So your business doesn't currently have an on-chain component?

Dio Casares:

No. We previously looked at perpetuals in the private market, to see if we should suggest to some clients that if they are considering hedging pre-IPO exposure—though it's a bit of a grey area itself—they might consider using perpetuals rather than setups like IBKR.

Frankly, we have had clients ask: "Should I hedge my exposure using perpetuals or through shorting setups like IBKR?" That's about the extent of our involvement in this area. We might help the Entropy team with some markets; they will try to offer some pre-markets earlier than Trade.xyz, that's my understanding. But it's certainly not a core part of our business.

The reason is, we don't want to anger the companies whose share registries we are on. Launching tokenized versions of their stock or launching pre-IPO markets, especially very early pre-IPO markets, is an easy way to really upset them. People might forget, Anthropic has a list that's basically "don't touch these people." For us, that would make it easy for us to end up on a similar list, so we won't do that.

Why Pre-IPO Perpetuals May Continue to Expand

Host Laura Shin:What is your outlook on the future development of the private market, especially the part involving blockchain?

Dio Casares:

We're at a very good point in time. Overall, Hyperliquid is rising fast, and the pre-IPO market is also developing.

Many major events that change the world and markets now happen on weekends, which is a huge boon for many RWA perpetuals that can trade 24/7. The same goes for pre-IPO perpetuals. Once they convert, they become regular RWA perpetuals.

Hyperliquid has previously used pre-market perpetuals as a loss leader, meaning they were willing to lose money initially to attract users and build market share for future profitability. I think this strategy will be adopted by more platforms in the future.

I'm not sure how the pre-IPO market will evolve, but this year we have a historically high number of IPOs. SpaceX, Anthropic, and OpenAI are all aiming for valuations above a trillion dollars, which has never happened before. Not to mention many other companies that could be mentioned.

So, now is indeed a good time for pre-IPO perpetuals to gain more attention. Cerebras is a good example, and if the SpaceX perpetual settles smoothly, trading volume for Anthropic and OpenAI-related contracts will likely only increase.

You'll see many trading platform providers starting to compete, trying to cover these pre-IPO markets because then they can dominate the subsequent trading volume after these markets convert to regular markets. That will be very interesting.