Compiled & Edited by: Deep Tide TechFlow

Guest: Dio Casares, Founder of Patagon

Original Title: The Shadow Market Behind Anthropic's Stock

Podcast Source: Bankless

Broadcast Date: May 14, 2026

Editor's Introduction

In this podcast, Patagon founder Dio Casares reveals the insider stories behind the secondary market trading of star companies like Anthropic. Patagon is a company focused on digital asset investment and private secondary market matching. Dio Casares states that secondary transactions related to Anthropic alone involve hundreds of billions of dollars, with a single transaction fee rate as high as 10%, and about 10%-20% of transactions involve fraud or share falsification, even the earnings of fund practitioners through such transactions already exceed their primary investment business.

Even more concerning are nested SPV (special purpose vehicle) structures, “forward contract” employee stock options, and “tokenized” private equity, which could trigger a wave of lawsuits lasting several years once Anthropic goes public, due to delays in multi-layer SPV distributions in the DTCC system, whether each layer GP opts to retain holdings, and the possibility that some equity may be invalidated at the company level.

Key Quotes

Market Structure and Arbitrage Opportunities

• “You can't just run to Anthropic and say, ‘I want to buy one million dollars worth of stock in this round,’ it's a market built on internal connections.”
• “Some people sell shares if they have them, others sell buyer resources; a few do both sides, that's the structure of this market.”
• “Even people in funds earn more from these secondary transactions than from their core investment businesses, so a lot of people are shifting to this market.”

Market Size and Fee Rates

• “The amount raised in the private market has surpassed IPO fundraising amounts in recent years, with recorded secondary market transactions and financing rounds exceeding 200 billion dollars.”
• “Many of the Anthropic deals we see have a one-time fee of 10% plus a long-term commission; if 10 billion dollars flows into this channel in one round, that's a fee pool of one billion dollars.”

Secondary Transactions Recognized and Not Recognized by the Company

• “Anthropic generally supports direct transactions, the company recognizes them, adds them to the shareholder registry, and then connected funds do joint distribution.”
• “The company despises platforms like Hive and Forge; they see a large block of shares and send mass emails to hundreds of thousands of unverified people on the platform saying, ‘I have discounted shares,’ which directly interferes with Anthropic's current fundraising.”
• “OpenAI and Anthropic recently made offers to employees, allowing them to sell up to 30 million dollars directly at this round's valuation. This is essentially the company ‘cutting off’ those sellers who originally intended to go through the grey secondary market.”

Fraud and Bad Debt

• “In the transactions we've reviewed, about 10%-20% are fraudulent; share certificates can be forged, which is direct fraud.”
• “More common than outright fraud is when someone claims to have shares but actually does not, takes the money first, and then looks for assets, often unable to find them.”
• “Under the American legal system, you are ‘innocent until proven guilty,’ so the issue is, if a position goes from 1 million to 50 million dollars, incurring 10 million dollars in legal fees to recover it, they might simply default, having netted 40 million.”

Nesting SPVs and Settlement Hell Post-IPO

• “Why are there second and third layer SPVs? Because it’s hard for buyers and sellers to ‘match exactly.’ A seller with 8 million dollars may have three buyers pooling resources.”
• “Anthropic directly names Sidecar, as they believe Sidecar's due diligence is insufficient; they basically let a document through if it looks ‘fine.’”
• “After the IPO, the real chaos is that the first layer SPV takes days to two weeks to get the stock, then asks LP if they want cash or stock, which then moves to the second and third layers… any GP at any layer wishing to hold and not distribute locks everyone else out.”
• “Post-IPO, the company will basically not chase those problematic shares; they will not raise any private rounds again, and the incentive to maintain market order is gone.”

Advice for Small Buyers

• “If you are a small buyer, investing 100,000 to 1 million dollars in some ‘tokenized version of Anthropic’ or a similar vehicle, most of the time you can't even open the lid to see the underlying, you can at most see the vehicle where the money is going, and that's usually second or third layer.”
• “I trust my gut; if you have a very bad feeling about this position, you should back out.”

The Real Operating Mechanism of Anthropic's Secondary Market Transactions

Host: Regarding Anthropic's secondary market, and even more broadly the private market, there are many questions. Before we start, can you introduce yourself and why you have a unique perspective on Anthropic's secondary market?

Dio Casares: Patagon has two core business lines, proprietary investment and client services. We've conducted secondary transactions ourselves and also offer secondary transactions as a product to help people find share channels.

Host: In other words, as a service for clients, you find popular secondary shares in the market and package them to sell to clients.

Dio Casares: That's completely correct.

Host: This places you in the front row of observing this market. The hottest funding pools right now are in the secondary market, especially Anthropic, as well as SpaceX and OpenAI. Can you share with the audience what is happening here? The vast majority have no concept of this area at all.

Dio Casares: Broadly speaking, there are two types of secondary markets. The first type is ‘primary-like’ secondaries. The name itself is a bit contradictory; it means rather than allowing a fund to inject money directly, someone in the market sets up SPVs (special purpose vehicles), on top of which more SPVs are built, and then the money is funneled in. This effectively gives the company new money, and the company indeed receives financing.

Employees selling their shares also fall into this category, as this is approved by the company. The company receives value from issuing shares to employees and allows them to turn the shares into cash.

The second type is truly secondary. You are buying shares from someone who has already bought stock from the company. This type has historically been more troublesome. The traditional view is that VCs need to wait for an IPO or acquisition to exit, but now funding rounds often reach hundreds of billions, far exceeding the 10 billion during past company IPOs, changing the liquidity timeline completely. When FTX declared bankruptcy, a large block of Anthropic shares was forced to be sold off due to the bankruptcy proceedings.

So the secondary market needs to be established, but at the same time, it is viewed with suspicion by a lot of management, as they believe it might compete with their fundraising stock sales.

Host: So aside from Anthropic's own appeal, this phenomenon arises from two structural inputs: one, the market size itself is already massive and the capital volume is larger; two, these companies are staying private longer, allowing the secondary market time to mature and for more participants to engage.

Dio Casares: Yes, I agree.

Host: Can we first discuss the normal situation? Anthropic is aware of the secondary market's existence, and some of these are recognized by the company. How is a secondary transaction acknowledged by Anthropic completed?

Dio Casares: More accurately, we can call it the SPV market. Some people in the market want to buy into Anthropic; they are not in the funds, nor have any particular loyalty to the company, purely out to make money. Anthropic overall supports direct transactions; the company recognizes them, adds them to the shareholder manual, then the connected funds do joint distribution, making money by helping the company raise funds.

At the moment, Anthropic is working with a few large PE (private equity) funds to operate this round of finance. These institutions are not flashy but are indeed connecting many people with shares. They are not listed on Anthropic's ‘unauthorized institutions’ list, so it can be basically determined that they are recognized by the company.

The other type is heavily disliked by management. These companies frequently issue legal letters directly to them, like platforms such as Hive and Forge. Their practice is to see a large block of shares and send mass emails to hundreds of thousands of unverified people on the platform saying, “I have discounted shares,” which directly disrupts Anthropic's fundraising this round. They are in the “find-a-deal” business, trying to locate shares cheaper than the current secondary market price or this round's valuation.

The result is that on Anthropic's side, family offices and major clients will come and say, “Hive and Forge said I could get a 20% discount, so why should I invest directly this round?” This makes it harder for Anthropic to raise funds. Worse is the psychological aspect; if a pronounced discrepancy in “sell price low, buy price high” appears in the market, it often implies a lack of market activity, which is a bad signal that the company needs to eliminate.

OpenAI and Anthropic recently made offers to employees, allowing them to sell up to 30 million dollars directly at this round's valuation. This is essentially the company ‘cutting off’ those originally intending to go through the grey secondary market.

Host: So authorized transactions by Anthropic fall into two categories: one is non-competitive, with the company itself fundraising, with money going into the company; the other is to improve future market structure, allowing employees or those wanting to sell in the ecosystem to sell before IPO, releasing selling pressure. This is a positive sum game that aligns with Anthropic's interests. The bad category consists of a bunch of middlemen who take cuts, providing no benefit to the company and making it look bad.

Dio Casares: Correct. In the U.S., there’s a regulation for securities not publicly traded: a six-month holding period. So some “tokenized private equities” you see, theoretically, if someone can constantly buy and sell back and forth, each time could be a violation of this law. Perhaps they’ve done some kind of workaround behind the scenes, but historically American regulators tend to believe that as long as the asset has some connection to the U.S., they have jurisdiction. Another thing Anthropic does not want is to be accused by regulators of “knowing and not acting.”

Host: So, Anthropic legally has no leeway to “pretend not to see”; once they are aware of these markets, they must take action.

Dio Casares: Correct.

Host: How big is this market? There are several hundred billion dollars related to Anthropic? How large is the proportion of unhealthy dark markets, and how large is the total market?

Dio Casares: This is basically the whole of the private side. Private funding also comes in many forms: several family offices collaborating to invest, raising funds through brokers or institutions like ours, charging fees, which is entirely different. Plus, brokers are tiered; the first layer brokers know many buyers but are also connected to another broker who accurately has shares. So the market structure is quite complex and the money is substantial.

One interesting statistic is that private funding has exceeded IPO fundraising for several years now, with recorded secondary market transactions and financing rounds exceeding 200 billion dollars. Considering that the fee rates aren’t just a few basis points, but the kind of one-time 10% fee plus long-term commissions we see in Anthropic deals; if 10 billion dollars flows into this channel in one round, that creates a fee pool of one billion dollars.

Host: Recently, I came across two pieces of social media reflecting the market's craziness. One is a guy in San Francisco writing on his Hing profile “I know people at Anthropic, zero commission dating,” using Anthropic stock shares to attract dates. The other is a lady tweeting, “Just brokering one secondary deal with Anthropic, I earned more than my entire earnings over my twenties; this is outrageous.” This reflects the state of social elite in San Francisco maneuvering around Anthropic shares. How did this happen?

Dio Casares: The person tweeting, I actually spoke with her. From a buyer's perspective, you want to buy Anthropic, but the company’s charter and agreements are not public and hard to access. You can't just run to Anthropic and say, “I want to buy one million dollars worth of stock this round, thank you.” This is a market built on internal relationships; some people sell shares if they have them, others sell buyer resources; a few do both sides. This is its market structure.

Even those within funds earn more from such secondary transactions than from their primary investment business, so many people are shifting to this market.

Host: Meaning everyone sees Anthropic equity as a gold mine, so a bunch of people are selling picks and shovels.

Dio Casares: Correct. And the competition is quite intense now, which is a good thing. Just a few months ago, there was no real competition; most people were intermediaries, not directly connecting with sellers. Now more and more people can find both buyers and sellers simultaneously and handle the entire process more professionally. But at the same time, the fees that can be charged have also dropped.

Moreover, a lot of people do not realize the risks: in some cases you cannot obtain shares from investors and thus have to buy employees' forward contracts. This has recently triggered problems; a well-known institution sold a forward contract for an xAI employee, who was later named in the lawsuit against OpenAI and accused of corporate espionage, leading to all their shares being reclaimed by the company. The result was: money was paid, fees were collected, but it turned into a mess, and all buying brokers were left hanging. That institution’s attitude was, “If you paid the fee, that’s your problem, not ours; we can only refund the original principal.” I believe these “fake SPVs” will increase, and this will turn into a game based on reputation: seeing who can build non-failing investment vehicles.

10-20% Fraudulent Share Certificates in Transactions

Host: Let's talk about why an investment vehicle might fail. I understand it's the nesting of SPVs, layers two, three, four; with each layer, the uncertainty regarding the actual shares becomes greater.

Dio Casares: The existence of second and third layer SPVs is due to “the willingness to buy and sell not aligning.” A seller with 8 million dollars rarely finds a buyer with exactly 8 million; it’s often pieced together by three buyers. Most people in this space aren't licensed brokers and cannot charge fees while brokering. But if you set up a fund, you can charge front-end management fees for managing the fund, and the fees are collected at the SPV level.

Host: Does Anthropic prefer these funds or clearly oppose them?

Dio Casares: It's better than having none. Because at least you have a tax filing if managed properly. Anthropic also publicly states which fund administrative service providers they recognize. They specifically named Sidecar, which is interesting, because others are fund or SPV brokers, while Sidecar is merely a fund administrative service provider. They named Sidecar because Anthropic believes Sidecar’s due diligence is insufficient, as they essentially greenlight documents that look “fine.”

Returning to the risks you mentioned, the first is that the shares aren’t real at all; share certificates can be forged, which is direct fraud. We've seen at least 10 such cases where the transfer records confirmed they were fake. However, there’s not much you can do, only whistleblowing and reporting. Sometimes it’s hard to tell whether they themselves created the forgery or if they're reselling fakes. There is indeed a lot of fraud in the market, but I don't think it’s as widespread as perceived; roughly 10%-20% of transactions are fraudulent. More common is claiming to have shares but actually not; they take the money first and then look to invest in the company, often failing to deliver.

Host: Is there any “unintentional fraud,” where individuals try their best but fail due to the market’s state, and thus don't actually get the promised assets? Is there this gray area?

Dio Casares: That would be called “gross negligence.” There’s not a lot of gray area. Resources like Pitchbook, shareholder manuals, and others that allow you to conduct due diligence should have been used when directly connecting with sellers. If you haven’t done due diligence on your clients or buyers, that’s negligence, which shouldn’t happen. If you bought from a well-known seller with access to the shareholder manual whose documents also got checked, and they still did something improper, that’s another matter, but the market does have a reputation; unreliable people are well-known in the circle.

Potential Lawsuits and Locked Stock Disputes After IPO

Host: After Anthropic's IPO, how does this speculative market "collapse"? Not negatively, but in terms of settlement, distribution of shares, and cash turnover.

Dio Casares: It mainly depends on two things: first, the broker account level at DTCC (Depository Trust & Clearing Corporation) and the AML (Anti-Money Laundering) procedures; second, the distribution terms of each fund. Some funds have complete autonomy over when to distribute; some stipulate that once an IPO occurs and shares become liquid, they’ll distribute immediately in kind or cash.

Imagine a three-layer SPV: the first layer obtains the stock and then asks the LP below whether they want shares or cash; all LPs in the second layer say they want stocks, then this is passed up; it depends on DTCC, usually a few days, but if banks are tricky, it could take up to two weeks, leading to a two-week delay. Then the second layer asks its LPs whether they want cash or stock, passing it to the third layer, which could be another 3 days to two weeks.

At any layer in between, if distribution rules allow GP to freely decide, for example, if Anthropic’s share price skyrockets post-IPO, the first layer GP might say, “I have a long-term commission; I want it to rise more,” or conversely, if there's a price drop, they might not want to deliver immediately, wanting to hold on longer. If such cases arise, downstream everyone won’t get their shares. Some might even hedge their long position in the public market, technically falling into gray areas; you might think you’ll receive your shares in 6 months, but end up waiting an extra month, causing a lot of lawsuits to emerge.

Host: It sounds like Anthropic wouldn’t be very concerned because for them, once the shares are distributed, it's done; the higher SPVs handle it themselves.

Dio Casares: Correct. Once listed, the company no longer needs a private transfer agency, only using it the first time when issuing stocks, every transaction thereafter goes through DTCC, and they basically don’t get involved. But many brokers and banks might oversee these transactions and say, “Anthropic declares this transaction void, we need to clarify if we can help you sell.” This could be quite troublesome.

But from a strategic perspective, post-IPO, the company will likely not go after those problematic shares; they won't conduct any more private rounds, and the initial incentive to maintain market order will dissipate.

Host: How big can this be? How many lawsuits? How many dollars involved? How long will it take to clean up?

Dio Casares: Lawsuits can take several years, and some cases will definitely drag out for years. I can’t specify a total amount; I think no one can. But this will be the “awakening moment” for this market.

I spoke the other day with someone from a small family office in Europe, and it was quite disheartening. I believe they invested in that problematic transaction mentioned earlier, and ultimately the money was returned. But I believe that GP did not inform LP that they were holding onto the returned money to continue operating, betting on Anthropic's appreciation. This kind of thing is very common: using returned money as trading capital to bet on increases, unless they can generate a 500% return, they won’t be able to cover the losses. I am not optimistic about their chances of achieving that. This account will have to be absorbed by that fund.

Host: What you’re concerned about is: some people subjectively want to do well but mess it up, such as buying fake equity. But why would customers still have their money post-mess?

Dio Casares: Yes, or negligence could have occurred. My intuition is that the fee structure for that large block of shares was heavily weighted, with GPs taking off the money, leaving no funds to return to LPs; or due to some reason, they felt they couldn’t refund. But the financial industry doesn’t operate like that: after things go wrong, someone must come out and say, “I’m sorry it didn’t work out; here’s your money back.”

Host: So the error path goes like this: you raise funds from friends and family, set up an SPV, the money’s there; you receive a verbal commitment from someone to deliver shares. At that moment, you have two choices: do nothing, keeping the money intact within the SPV while waiting for the shares to come; or count your chickens early, “I just made a huge sum; let’s buy a house or a Porsche,” and then on the day of delivery, you realize the shares never arrived, but the money's been spent with nothing to repay.

Dio Casares: Absolutely correct.

Host: Let’s broaden our lens. The scale of the private market is massive; companies delay their IPOs, funds change hands privately, gradually becoming their own internal market, which is precisely the opposite of the public market. Yet now the coolest companies are lingering in this market longer. How will this market evolve in the future?

Dio Casares: Saying it is “completely unregulated” isn’t quite accurate; there are indeed regulations in place, but it is quite “wild,” and hasn’t been strictly enforced, unless there’s clear fraud, regulation generally doesn’t interfere much—they can’t keep up. Would you rather the U.S. financial regulators chase someone for not doing the correct filings or for illegal financing? Most people would certainly say to go after illegal financing. Sometimes the same group is doing both things.

The market continuously repeats similar patterns. This resembles the recent crypto phase where low liquidity and high FDV created crazy market conditions, making it easier for companies to finance. In this round, there are indeed real technologies behind it; I personally use Claude, and their income has become quite substantial.

Interestingly, existing large institutions, banks have their own or collaborate on secondary departments; they are very cautious and cannot keep up with this market's pace. Thus, you see new companies entering to fill this gap. At the same time, large funds are also setting up SPVs, just with different structures, targeting only their LPs. This trend is a shift from “funds managed uniformly” to “directly managed funds.” I believe this will continue for some time until this round cycle ends. A batch of people will buy what is essentially “locked tokens” and then lose a lot, ultimately saying, “Alright, I’ll return the money to the VC fund.” This wave of hot money will go elsewhere, but the secondary market in the U.S. will become more professional.

Patagon's Strategy and Philosophy

Host: Returning to what you do at Patagon. Based on your experience and understanding of the secondary market, can you introduce Patagon's strategy and philosophy?

Dio Casares: Initially, we only did proprietary and transaction-entry. Later, one time a friend paid me a fee, and I asked him why. He told me another broker was going to charge him two to three times the amount, and what he paid me was equivalent to the savings. This made me realize that growing up in the Bay Area, I know many people and understand whom to call and how to conduct background checks, while many of my friends have international backgrounds, lacking that kind of familiarity in San Francisco. I started doing this part-time and gradually realized this could be turned into a business, especially regarding branding and processes.

Look at platforms like Forge and Hive; they do not verify whether equities are real, do not vet buyers, and do not collect KYC information (here I’m only talking about their marketplace services, as investing opportunities they conduct directly is another matter), yet they still charge 3.5%. They just provide you an introduction and a fake order book, and you have to negotiate via email; they charge 3.5% on that transaction too. We find that absurd.

What we do is find deals ourselves, set up investment vehicles ourselves, conduct due diligence ourselves; ensuring the shares are real and the structure is compliant. Clients can invest directly through our platform without first negotiating prices, requesting investment vehicle documents, signing, and then emailing back and forth for payment. Everything is done in one place, and ultimately we can allow clients to take their positions for credit financing. We aim to provide clients with far more value than just letting them invest and then leaving them.

We’ve handled some complex deals, like a crypto company with all employee forward contracts. In the due diligence process, we conducted background checks on each employee to see if they had gambling issues or if anyone close to them gave negative reviews. If we found someone problematic, we didn’t work with them; everyone else was fine, and the whole transaction went smoothly.

Host: This, in turn, helps you build credibility; when you go to acquire shares of Anthropic's secondaries or others, you can say, “Our client base has undergone quality screening.”

Dio Casares: Exactly. We can also tell clients, “We’ve handled tough deals.” In that transaction, there were no other channels in the market to obtain authorized shares; we managed to get clients into opportunities others couldn’t access. Clients appreciate that, and next time they’ll naturally turn to you for such matters.

Legal Risks of Tokenized Equity and Perpetual Contracts Before IPO

Host: If some listeners have already purchased Anthropic's secondaries or other companies' secondaries but know nothing of the truth behind the scenes, what advice or actions would you suggest?

Dio Casares: It’s hard to generalize because the market structure varies widely. Some people now hold perpetual contracts, which I personally wouldn’t recommend; ironically, they belong to a different legal subclass and thus the risks are not so obvious. Funding rates may be aggressive, but that’s the price you pay to align it with the IPO opening price.

If you are a small buyer, investing 100,000 to 1 million dollars in some “tokenized version of Anthropic” or other similar vehicles, most of the time you can't even open the lid to see the underlying. You can at most see the vehicle where your money is going, and that’s typically second or third layer. I would suggest not to increase your position; if your gut feeling is very bad about this position, generally I trust my gut, then pull out.

Host: Are the tokenized perpetual contracts you mentioned making genuine claims to the underlying equity or are they merely predictions or subjective mappings?

Dio Casares: Many institutions are currently engaged in this, though each has different mechanisms. The idea is that once these things are launched, they’re similar to pre-IPO perpetual contracts where funding rates can be extremely wild. Pre-IPO perpetual contracts differ from typical perpetual contracts because market makers already have underlying trades as hedges, and the hedging methods differ from the U.S. stock market structure. Ultimately, they will converge on a real stock that allows for arbitrage. Therefore, as the IPO approaches, the prices and funding rates of perpetual contracts will align with “normal market” levels.

Host: Is there any topic that I haven’t asked about?

Dio Casares: I think we’ve covered quite comprehensively.