Anthropic’s Secondary Market Transactions Exposed: Fraud, SPVs, and IPO Risks

Organized & Compiled by DeepChain TechFlow

Guest: Dio Casares, Founder of Patagon

The Shadow Market Behind Anthropic’s Stock

Podcast source: Bankless

Broadcast date: May 14, 2026

In this podcast, Patagon’s founder, Dio Casares, reveals the inner workings of secondary market transactions surrounding star companies like Anthropic. Patagon is a firm specializing in digital asset investments and private secondary market matchmaking. Dio Casares states that secondary transactions related solely to Anthropic involve hundreds of billions of dollars, with transaction fees reaching as high as 10%. Approximately 10% to 20% of these trades involve fraud or fabricated equity stakes, and even fund professionals have earned more from these transactions than from their core investment activities.

Even more concerning are nested SPV (special purpose vehicle) structures, "forward contract"-style employee equity, and "tokenized" private equity; once Anthropic goes public, delays in distribution through the DTCC system, whether each layer of GP chooses to hold, and the potential nullification of certain equity at the corporate level will trigger a wave of litigation lasting several years.

Market Structure and Arbitrage Opportunities

• You can't just go to Anthropic and say, 'I want to buy $1 million worth of shares in this round'—it's a market built on insider connections.
• Some people sell their shares, others sell access to buyers, and a few do both—that’s the structure of this market.
• Even people within funds are earning more from this type of secondary trading than from their primary investment activities, so many are shifting toward this market.

Market Size and Fees

• Private market fundraising has exceeded IPO fundraising over the past several years, with recorded secondary market transactions and funding rounds totaling over $200 billion.
• We’ve seen many Anthropic deals with a one-time fee of 10% plus ongoing carry; if $10 billion enters through this channel in a single round, the fees alone amount to $1 billion.

Supported and Unsupported Second-Tier Tokens

• Anthropic generally supports direct trading; the company recognizes investors, registers them on the shareholder roll, and then partners with affiliated funds for co-distribution.
• The company hates platforms like Hive and Forge—they see a large block of shares and send mass emails to hundreds of thousands of users on their platform who haven’t completed KYC, saying, “I have discounted shares available,” which directly disrupts Anthropic’s current fundraising round.
• OpenAI and Anthropic have recently extended offers to employees, allowing them to sell up to $30 million in shares at the current valuation. This is essentially the companies intercepting sellers who would otherwise have turned to the gray secondary market.

Fraud and bad debt

• Of the transactions we've reviewed, approximately 10%-20% are fraudulent; equity certificates can be forged, constituting direct scams.
• More common than outright scams are cases where people claim to have inventory but don’t—they take payment first and then try to find the product later, often failing to do so.
• Under the U.S. legal system, you are presumed innocent, so the issue is this: if a position grows from $1 million to $500 million, and it would cost $10 million to sue to recover it, he might simply default, since he would still net a profit of $400 million.

Nested SPVs and the Settlement Hell After an IPO

• Why are there second- and third-layer SPVs? Because it’s difficult for buyers and sellers to perfectly match. An $8 million seller might be matched with three buyers pooling their funds together.
• Anthropic directly named Sidecar, stating that Sidecar’s due diligence was insufficient, essentially approving documents just because they “looked fine.”
• The real chaos after the IPO is that the first-layer SPV takes several days to two weeks to receive the shares, then asks LPs whether they want cash or shares, and passes it on to the second layer, third layer... If any GP in the chain decides to hold and lock their position without distributing, everything downstream gets blocked.
• After the IPO, companies rarely seek to reclaim problematic shares again; they won’t conduct additional private placement rounds, and the incentive to maintain market order disappears.

Advice for small buyers

• If you're a small buyer, putting $100,000 to $1 million into some 'tokenized version of Anthropic' or similar vehicle, you rarely get to look beneath the surface—you can usually only see the vehicle your money goes into, which is often a second- or third-layer entity.
• I trust my intuition—if you have a really bad feeling about this position, it’s time to exit.

Moderator: There are many questions about the Anthropic secondary market, and more broadly, the private market. Before we begin, could you introduce yourself and explain why you have a unique perspective on the Anthropic secondary market?

Dio Casares: Patagon has two core business lines: proprietary investing and client-facing services. We have conducted secondary market investments ourselves and also offer secondary market access as a client service to help people find share opportunities.

Host: So, as a service to your clients, you go out to the market to find popular secondary shares, bundle them together, and sell them to your clients.

Dio Casares: Exactly right.

Host: That puts you in the front row for observing this market. Currently, the hottest pools are in the secondary market, especially around Anthropic, SpaceX, and OpenAI. Could you explain to the audience what’s happening here? Most people have no idea about this at all.

Dio Casares: Broadly speaking, secondaries fall into two categories. The first is primary-like secondaries. The name itself is somewhat contradictory—it means that instead of allowing a fund to invest directly, someone in the market sets up an SPV (special purpose vehicle), then layers another SPV on top of it before investing the funds. This actually brings new capital to the company, and the company does receive financing.

Employee stock sales also fall into this category, as they are approved by the company. The company has already received value from issuing shares to employees and now allows employees to liquidate those shares.

The second type is truly secondary. You’re buying shares from someone who previously purchased them directly from the company. This category has historically been complicated. Traditionally, VCs waited for an IPO or acquisition to exit, but now funding rounds often reach tens of billions, far exceeding the $10 billion valuations of past IPOs, completely altering the timeline for liquidity. When FTX collapsed, a significant portion of Anthropic’s shares was forced into sale due to bankruptcy proceedings.

Therefore, a secondary market needs to be established, but it is also viewed with considerable skepticism by many executives, who fear it may compete with their own stock sales used for fundraising.

Host: So, beyond Anthropic’s own appeal, two structural factors have contributed to this phenomenon: first, the market size itself is already enormous, with even larger capital volumes; second, these companies remain private for longer, giving the secondary market time to mature and attract more participants.

Dio Casares: Yes, I agree.

Moderator: Could we first discuss the normal scenario? Anthropic is aware of the secondary market, some of which consists of company-approved secondaries. How is a secondary transaction approved by Anthropic completed?

Dio Casares: A more accurate term might be the SPV market. Some participants in the market simply want to buy Anthropic shares; they aren’t part of any fund and have no particular loyalty to the company—they’re purely motivated by profit. Anthropic as a whole supports direct transactions, with the company approving and listing them on its shareholder handbook, followed by co-distribution through partnered funds that earn revenue by helping the company raise capital.

Anthropic is currently working with several large private equity firms on this round of financing. These institutions are low-profile but are actively placing shares with numerous investors. They are not on Anthropic’s published list of unauthorized entities, so they can be reasonably assumed to be approved by the company.

Another category is strongly disliked by management, and these companies often receive legal notices directly. Platforms like Hive and Forge, for example, monitor large share offerings and then send mass emails to hundreds of thousands of users on their platform who haven’t completed KYC, claiming, “I have discounted shares available.” This directly disrupts Anthropic’s current fundraising round. Their business model is essentially arbitrage: they attempt to find shares priced lower than the current secondary market rate or the valuation of this round.

As a result, family offices and large clients come to Anthropic saying, “Hive and Forge told me I can get a 20% discount—why should I invest directly in this round?” This makes Anthropic’s fundraising more difficult. Even worse, psychologically, a clear spread between low selling prices and high buying prices signals market illiquidity, which is a negative indicator that the company must eliminate.

OpenAI and Anthropic recently extended offers to employees, allowing them to sell up to $30 million in shares at the current valuation. This effectively allows the companies to bypass secondary market sellers who would otherwise operate in the gray market—many potential sellers have already sold their full allocation through the offer and no longer need to enter private agreements such as “I’ll buy your shares a year from now.”

Host: So, Anthropic-endorsed transactions fall into two categories: first, non-competitive transactions where the company itself is raising funds, with money going directly into the company; second, transactions that improve future market structure by allowing employees or others in the ecosystem to sell before the IPO, thereby releasing selling pressure. These are positive-sum, beneficial transactions aligned with Anthropic’s interests. The problematic type involves numerous intermediaries that extract fees, providing no benefit to the company while making it appear worse off.

Dio Casares: Yes. In the U.S., there is a regulation requiring a six-month holding period for unregistered securities. Therefore, some of the “tokenized private equity” you see could theoretically violate this law if someone continuously buys and sells back and forth. Perhaps they have some kind of workaround in the background, but historically, U.S. regulators have tended to assert jurisdiction whenever an asset has any connection to the U.S. Another thing Anthropic does not want is to be accused by regulators of “knowing but failing to act.”

Host: In other words, Anthropic has no legal option to turn a blind eye—once they become aware of these markets, they must take action.

Dio Casares: Yes.

Host: How large is this market really? Are there hundreds of billions of dollars just related to Anthropic? What percentage of this represents unhealthy black markets, and what percentage represents the entire market?

Dio Casares: This essentially covers everything on the private side. Private placements come in many forms: some involve multiple family offices pooling capital together, while others raise funds through brokers or institutions like ours and charge fees—completely different structures. Moreover, brokers themselves are layered: a first-tier broker may know many buyers but also relies on another broker who actually holds the allocation. As a result, the market structure is highly complex, and the amounts of capital involved are substantial.

An interesting data point is that private fundraising has exceeded IPO proceeds for several years now, with combined secondary market transactions and funding rounds exceeding $200 billion. Given that fees are not just a few basis points but rather the one-time 10% plus long-term carry we’ve seen in deals like Anthropic’s, if $10 billion of this round flows through such channels, the fees alone would amount to $1 billion.

Host: I recently came across two social media posts reflecting the market’s frenzy. One was a guy in San Francisco who wrote on his Hinge profile, “I know someone at Anthropic—zero commission on dates,” using Anthropic shares as a dating hook. The other was a woman tweeting, “I made more from brokering a single secondary Anthropic transaction than I earned in total during my entire 20s—that’s insane.” This is the state of social maneuvering among San Francisco’s elite around Anthropic shares. How did this happen?

Dio Casares: I’ve actually spoken to the person who posted that tweet. From a buyer’s perspective, you want to buy Anthropic stock, but the company’s charter and agreements aren’t publicly available or easily accessible. You can’t just go to Anthropic and say, “I’d like to buy $1 million worth of shares in this round, thanks.” It’s a market built entirely on insider connections—some people sell their shares, others sell access to buyers, and a few do both. That’s the structure of this market.

People in funds are making more money from these secondary trades than from their core investment activities, so many are shifting toward this market.

Host: So everyone sees Anthropic's equity as a gold mine, and a huge number of people are selling picks and shovels.

Dio Casares: Yes, and now the competition is much fiercer, which is a good thing. A few months ago, there was virtually no competition—most people were just intermediaries who didn’t deal directly with sellers. Now, more and more people are able to connect buyers and sellers directly and manage the entire process professionally. But at the same time, the fees you can charge have come down.

There’s another risk many people don’t realize: in some cases, you can’t acquire shares directly from investors and are forced to buy forward contracts from employees. This recently blew up when a well-known institution sold a forward contract on shares held by an xAI employee—who was later named in xAI’s lawsuit against OpenAI, accused of corporate espionage, and had all his shares reclaimed by the company. The result? Money was paid, fees were collected—but everything fell apart, leaving all buyer brokers stranded. The institution’s stance? “If you paid the fee, that’s your problem, not ours—we’ll only refund your original principal.” I believe these “fake SPVs” will become more common, and in the future, this will turn into a reputation game—where success depends on who can build investment vehicles that don’t collapse.

Host: Let’s discuss why an investment vehicle might collapse. I understand it involves a nested structure of SPVs—second, third, fourth layers—each layer charging fees, and with each subsequent layer, the certainty of whether the corresponding equity actually exists diminishes further.

Dio Casares: Layer 2 and Layer 3 SPVs exist because "buy and sell intentions don't align." An seller offering $8 million rarely has a single buyer ready to purchase exactly that amount—it might take three buyers to come together. Most participants in this space are not licensed brokers and cannot charge fees by acting as intermediaries. However, if you set up a fund, you can simply charge an upfront management fee for managing the fund, with fees collected at the SPV level.

Host: Does Anthropic favor these funds or explicitly oppose them?

Dio Casares: Better than nothing, because at least you have tax reporting, if managed properly. Anthropic has also publicly stated which fund administrators they recognize. They specifically named Sidecar, which is interesting because others are brokers for funds or SPVs, while Sidecar is solely a fund administrator. Anthropic named Sidecar because they believe Sidecar’s due diligence was insufficient—essentially approving documents just because they “looked fine.”

Regarding the risks you mentioned, the first is that the equity isn’t real at all—share certificates can be forged, which constitutes outright fraud. We’ve encountered at least ten such cases where reviewing the share transfer records confirmed they were fake, but there’s little you can do beyond reporting them. Sometimes it’s hard to tell whether the seller created the fake themselves or is simply reselling forged shares. There are indeed quite a few scams in the market, but I don’t believe they’re as widespread as some external reports suggest—perhaps around 10% to 20% of transactions involve fraud. More common than outright fraud, however, are cases where individuals claim to hold shares they don’t actually own, collect payment upfront, and then attempt to invest in the company afterward—often failing to do so.

Host: Is there such a thing as "unintentional fraud," where someone does their best, but due to the nature of the market, they end up not delivering the promised assets? Does this gray area exist?

Dio Casares: That’s called “gross negligence.” There isn’t that much gray area. Resources like PitchBook, shareholder manuals, and other due diligence tools should inherently be used when dealing directly with sellers. Failing to conduct due diligence on your buyers or clients is negligence—and that shouldn’t happen. If you bought from a reputable seller with access to shareholder manuals, reviewed the documents, and they still engaged in shady behavior, that’s a different story—but the market has reputation, and unreliable people are well-known in the industry.

Host: After Anthropic’s IPO, how will this pile of speculative markets “collapse”—not in a bad way, but through settlement, distribution of shares, and transfer of cash.

Dio Casares: Focus on two key things: first, the broker accounts and AML (anti-money laundering) procedures at the DTCC (Depository Trust & Clearing Corporation) level; second, the distribution terms of each fund. Some funds have full discretion over when to distribute, while others stipulate that distributions must occur immediately upon IPO and when shares become tradable, either in kind or in cash.

Imagine a three-layer SPV: The first layer acquires the shares and then asks its underlying LPs whether they want physical shares or cash; if all LPs in the second layer say they want shares, that request is passed upward—this depends on DTCC, typically taking a few days, but up to two weeks if the bank is involved, resulting in a two-week delay. Then, the second layer asks its own LPs whether they want cash or shares, passing the request to the third layer, adding another three days to two weeks.

At any intermediate layer, if the distribution rules allow the GP to decide freely—for example, if Anthropic’s stock surges after its IPO, and the first-layer GP says, “I have a long-term carry; I want to let it rise further”; or conversely, if it plummets at launch and the GP doesn’t want to deliver immediately and prefers to wait a few more months—everyone downstream will be unable to receive their shares. Additionally, some parties may hedge their long positions on the open market, which exists in a technical gray area: you might have expected delivery in six months, only to find you must wait an additional month, leading to numerous potential lawsuits.

Host: It sounds like Anthropic itself isn’t too concerned, since once the shares are issued, it’s handled entirely by their senior SPV.

Dio Casares: Yes. After the listing, the company no longer needs a private transfer agent—it only uses one for the initial share issuance, and all subsequent transactions go through DTCC, so the transfer agent essentially steps away. However, many brokers and banks may look at these trades and say, “Anthropic claims this is invalid; we need to verify whether we can help you sell it.” This could be quite cumbersome.

However, from a game theory perspective, after the IPO, companies generally have no incentive to reclaim problematic shares, as they will not conduct further private placement rounds, eliminating the original strategic motivation to maintain market order.

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

Dio Casares: The lawsuits will take years—some cases will certainly drag on for years. I can’t say the exact total amount, and I don’t think anyone can. But this will be the market’s moment of awakening.

A few days ago, I spoke with someone from a small European family office, and it was quite disheartening. I believe they invested in the problematic transaction mentioned earlier, and ultimately, the funds were returned. But I suspect the GP did not inform the LPs and instead kept the returned money to attempt another trade, hoping to profit from Anthropic’s appreciation. This is all too common: using returned capital as fresh investment capital to chase upside—unless they can generate a 500% return, they won’t be able to make up the loss. I’m not optimistic they’ll succeed. This loss will now fall entirely on the fund itself.

Host: You're concerned that some people intend to do the right thing but end up messing up—like buying fake equity. But why is there still client money after things go wrong?

Dio Casares: Yes, or there was a misstep. My intuition is that the fee structure for that large stake was overly burdensome—the GP took the money, leaving nothing left to return to the LPs; or for some reason, he felt he couldn’t return it. But that’s not how finance works. When something goes wrong, someone must step forward and say, “I’m truly sorry this didn’t work out; I’m returning your money.”

Host: So the mistake goes like this: you raise money from friends and family, set up an SPV, and once the funds are in place, you receive a verbal promise from someone else to deliver shares. At this point, you have two choices: do nothing and leave the money untouched in the SPV while waiting for the shares to arrive; or you start counting your chickens—thinking, “I’ve made a huge profit,” and go buy a house or a Porsche—only to find on delivery day that the shares never came, but your money is already spent and nothing is left to return.

Dio Casares: Exactly right.

Host: Let’s pull back the camera. The private market is enormous—companies delay their IPOs, and capital changes hands privately, gradually becoming its own internal ecosystem. This is precisely the opposite of the public market, yet today’s most exciting companies are staying in this space longer than ever. How will this market evolve in the future?

Dio Casares: It’s not entirely fair to say it’s “completely unregulated”—there is actually a lot of regulation, but it’s very loose and not strictly enforced, unless there’s clear fraud, in which case regulators generally don’t intervene because they can’t possibly cover everything. Would you rather have the U.S. financial regulators pursue someone for failing to file proper paperwork, or go after illegal fundraising? Most people would say, obviously, go after the illegal fundraising. Sometimes it’s the same people doing both.

Markets always repeat similar patterns. This is much like the recent period in crypto characterized by low circulating supply and high FDV, where limited supply fueled wild price movements and made it easier for companies to raise funds. This cycle is indeed backed by real technology—I personally use Claude, and their revenue is already very substantial.

Interestingly, existing large institutions and banks—whether they have their own or partner secondary departments—are extremely cautious and struggle to keep pace with this market. As a result, you’re seeing a wave of new companies entering to fill this gap. Meanwhile, large funds are also creating SPVs, but with different structures and exclusively for their own LPs. This trend reflects a shift of capital from “investing through funds managed collectively” toward “directly managed capital.” I believe this will continue for some time until the end of this cycle. Some investors will buy vehicles equivalent to “locked-up tokens,” suffer significant losses, and ultimately conclude, “Alright, I’ll just put my money back into VC funds.” This wave of hot money will move elsewhere, but the U.S. secondary market will become more professional.

Moderator: Let’s return to what you’re doing at Patagon. Drawing from your experience and insights in the secondary market, could you introduce Patagon’s strategy and philosophy?

Dio Casares: We initially only did proprietary trading. Then, one day, a friend paid me a fee, and I asked why. He told me another broker was charging him two to three times as much, and what he paid me was essentially the amount he saved. That made me realize that, having grown up in the Bay Area and knowing many people, I knew who to call and how to conduct background checks—while many of my friends had international backgrounds and lacked strong local connections in San Francisco. I started doing this part-time, and gradually realized it could become a business, especially in terms of branding and processes.

Look at platforms like Forge and Hive—they don’t verify whether shares are genuine, don’t screen buyers, and don’t collect KYC information (we’re only referring to their marketplace business; their direct investment opportunities are a separate matter). Yet they still charge 3.5%. They simply provide an introduction and a fake order book, leave you to negotiate prices via email, and still take a 3.5% fee on the transaction. We think this is outrageous.

We handle sourcing deals, setting up investment vehicles, and conducting due diligence ourselves—ensuring that equity is genuine and structures are compliant. Clients can invest directly in these deals on the platform without needing to negotiate prices first, request investment vehicle documents, sign paperwork, or exchange emails to arrange payments. Everything is completed in one place, and we also enable clients to use their positions for credit financing. The value we aim to deliver goes far beyond simply “getting you into this deal and leaving you on your own.”

We have handled complex orders, such as one for a cryptocurrency company involving forward contracts for all employees. During the due diligence process, we conducted individual background checks on each employee to assess whether they had gambling issues or received negative feedback from acquaintances. We identified one problematic individual and chose not to proceed with them; all others were clear, and the entire transaction was completed successfully.

Host: This also helps you build credibility—you can say, “Our customer base is quality-vetted,” when acquiring shares in Anthropic or other companies.

Dio Casares: Exactly. We could tell our clients, “We’ve handled difficult orders.” At the time of that trade, no other channel in the market could access the authorized shares—we got our client into an order that others couldn’t enter. The client will be grateful and will naturally come to you next time something like this arises.

Host: If listeners have already purchased secondary shares of Anthropic or other companies but are unaware of the authenticity behind them, what advice or actions would you recommend?

Dio Casares: It’s hard to generalize, as market structures vary too widely. Some people currently hold perpetual contracts—though I personally don’t recommend them—it’s ironic that perps, as derivatives, fall into a completely different legal category, making their risks less apparent. The funding rate may be aggressive, but that’s the price you pay to align it with the IPO opening price.

If you're a small buyer with $100,000 to $1 million invested in some "tokenized version of Anthropic" or a similar vehicle, you often won't be able to fully see beneath the surface. At best, you'll only see the vehicle your money went into—which is typically a second- or third-layer entity. I’d advise against adding more; if your gut feeling about this position is strongly negative—which I generally trust—I’d recommend exiting.

Host: You mentioned tokenized perpetual contracts—are they based on genuine claims to the underlying equity, or are they merely predictions or subjective mappings?

Dio Casares: Many institutions are currently doing this. Although each platform’s mechanism differs, the underlying idea is that once these assets go live, the funding rates for pre-IPO perpetual contracts can become extremely volatile. Pre-IPO perpetual contracts differ from standard perpetual contracts because market makers already have underlying trades to hedge against, and their hedging strategies differ from those in the U.S. stock market. Ultimately, however, they converge toward the price of an actual stock, enabling arbitrage opportunities. As the IPO approaches, the price and funding rate of these perpetual contracts tend to normalize toward market-expected levels.

Host: Is there anything else I haven’t asked about?

Dio Casares: I think we've covered everything thoroughly.