Bankless Interview: Private Equity Insiders Reveal the Inside Story of Anthropic's Primary Market Trading

Organized & Compiled 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 inside story of the secondary market trading around star companies like Anthropic. Patagon is a company focused on digital asset investment and private secondary market matching. Dio Casares states that secondary trading (here "secondary" refers to a primary-like secondary, where shareholders or employees privately transfer equity to others, explained in detail later; all references to Anthropic secondary trading in the text have this meaning.) related to Anthropic alone involves tens of billions of dollars, with single transaction fees as high as 10%. About 10%-20% of closed deals involve fraud or fake equity, and even fund practitioners earn more money from such transactions than from their core investment business.

What's more alarming are the nested SPV (Special Purpose Vehicle) structures, "forward contract" type employee equity, and "tokenized" private equity. Once Anthropic IPOs, delays in distributing multi-layered SPVs within the DTCC system, the decision of each layer's GP to hold or not, and the potential cancellation of some equity at the company level will trigger a wave of lawsuits lasting several years.

Highlights

Market Structure and Arbitrage Space

• "You can't just go to Anthropic and say, 'I want to buy $1 million worth of stock in this round.' This is a market built on internal connections."
• "Some people who have shares sell shares; some who have buyer resources sell buyer resources; a few do both. That's the structure of this market."
• "Even people inside funds make more money from this kind of secondary trading than from their main investment business, so many are shifting into this market."

Market Size and Fee Rates

• "Private market fundraising has exceeded IPO fundraising in the past few years. Recorded secondary market transactions plus financing rounds amount to over $200 billion."
• "Many Anthropic deals we see involve a one-time fee of 10% plus long-term cuts. If $10 billion comes in through such channels in a round, the fee pool alone is $1 billion."

Company-Approved vs. Non-Approved Secondary

• "Anthropic generally supports direct trading, recognized by the company, listed on the shareholder register, and then jointly distributed by partnering funds."
• "Companies hate platforms like Hive and Forge the most. They see a large block of shares and email hundreds of thousands of un-KYCed people on their platform saying, 'I have discounted shares,' which directly interferes with Anthropic's fundraising for that round."
• "OpenAI and Anthropic recently made employee tender offers, allowing employees to sell up to $30 million directly at the valuation of the current round. This is actually the company 'intercepting' sellers who would otherwise go through gray secondary markets."

Fraud and Bad Debt

• "Among the deals we've seen, about 10%-20% involve fraud. Equity certificates can be forged—it's outright scam."
• "More common than pure fraud is someone claiming to have shares but doesn't, taking the money first and then trying to source the shares, often failing."
• "Under the U.S. legal system, you're 'presumed innocent.' So the problem is, if a position goes from $1 million to $50 million, and suing to get it back costs $10 million, they might just default, still netting $40 million."

Nested SPVs and Post-IPO Settlement Hell

• "Why are there two or three layers of SPVs? Because it's hard for buyers and sellers to 'perfectly match.' An $8 million seller might face three buyers piecing it together."
• "Anthropic directly named Sidecar. They think Sidecar's due diligence is insufficient, basically approving things after seeing a document that 'looks okay.'"
• "The real chaos post-IPO is: the first SPV layer gets the stock in days to two weeks, then asks LPs if they want cash or stock, then passes it to the second layer, third layer... If any intermediate layer GP decides to hold and lock up the position without distributing, everyone downstream gets stuck."
• "Post-IPO, companies basically won't chase down problematic shares anymore. They won't do another private round, so the game-theory motivation to maintain market order disappears."

Advice for Small Buyers

• "If you're a small buyer with $100,000 to $1 million in some 'tokenized version of Anthropic' or similar vehicle, most of the time you can't even peel back the layers to see the underlying. At best, you see the vehicle your money goes into, and that's usually the second or third layer."
• "I trust intuition. If your gut feeling about this position is really bad, you should exit."

The Real Mechanics of Anthropic's Secondary Market Trading

Host: There are many questions about Anthropic's secondary market and the broader private market. Before we start, could 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 invested in secondary trades ourselves and also offer secondary trading as a product for clients, helping them find share access.

Host: So, as a service to clients, you go to the market to find hot secondary shares and package them for clients.

Dio Casares: Exactly.

Host: This puts you in the front row to observe this market. Currently, the hottest pool of capital is the secondary market, especially for Anthropic, SpaceX, OpenAI. Can you explain what's happening here? Most people have no idea.

Dio Casares: Broadly, there are two types of secondary. The first is primary-like secondary. The name itself is contradictory—it means instead of a fund directly investing, people in the market set up SPVs, then SPVs on top of SPVs, and invest the money. This is actually new money for the company; the company does get the financing.

Employee stock sales also fall into this category because it's company-approved. The company got value from issuing stock to employees, now letting them cash out.

The second type is true secondary. You're buying shares from someone who already bought them from the company. This type has historically been troublesome. Traditionally, VC exits waited for IPO or M&A, but now financing rounds are tens of billions, far exceeding the $10 billion companies used to raise at IPO. The liquidity timeline is completely changed. When FTX went bankrupt, a large chunk of Anthropic shares was forced to be sold, driven by bankruptcy proceedings.

So the secondary market needed to be built, but is also viewed with suspicion by many managements who see it as competing with their own equity sales for fundraising.

Host: So besides Anthropic's own appeal, two structural inputs drive this phenomenon: one is the massive market size itself, with larger capital amounts; two, these companies stay private longer, giving the secondary market time to mature and participants to increase.

Dio Casares: Yes, I agree.

Host: Can we talk about the normal case first? Anthropic knows the secondary market exists, and some of it is company-approved secondary. How does an Anthropic-approved secondary transaction happen?

Dio Casares: A more accurate term might be the SPV market. There are people in the market who just want to buy Anthropic, they're not in funds, have no special loyalty to the company, purely for profit. Anthropic overall supports direct trading, company-approved, on the shareholder list, then co-distributed by partnering funds who make money by helping the company raise funds.

Anthropic is doing exactly that with several large PE firms for this current round. These institutions aren't flashy but are indeed connecting shares to many people. They aren't on Anthropic's public "unauthorized institutions" list, so they're basically company-approved.

Another category is what management really hates. These companies often send them legal letters. Like platforms such as Hive, Forge. Their play is: seeing a large block, they email hundreds of thousands of un-KYCed people on their platform saying "I have discounted shares," which directly interferes with Anthropic's fundraising for the round. They're in the "scavenger" business: trying to find shares cheaper than the current secondary market price or round valuation.

The result is family offices and big clients come to Anthropic saying, "Hive/Forge says I can get a 20% discount, why should I invest directly in this round?" This makes Anthropic's fundraising harder. Worse is the psychological aspect: a clear "sell low, buy high" spread in the market often signals low activity, a bad signal the company wants to eliminate.

OpenAI and Anthropic recently made employee tender offers, allowing employees to sell up to $30 million directly at the round's valuation. This is actually the company "intercepting" sellers who would otherwise go through gray secondary markets. Many who wanted to sell have sold enough in the tender offer and won't sign private "I'll buy your stock a year later" contracts.

Host: So company-approved transactions are of two types: one is non-competitive, the company itself is fundraising, money goes to the company; two, improving future market structure, letting employees or ecosystem sellers sell before IPO, releasing sell pressure. These are benign, positive-sum trades aligned with Anthropic's interests. The bad type involves a bunch of middlemen "extracting water," giving the company no benefit and making it look bad.

Dio Casares: Right. In the US, there's a rule for unlisted securities: a six-month holding period. So some "tokenized private equity" you see, theoretically if someone could keep trading back and forth, each trade might violate this law. Maybe they have some avoidance in the backend, but historically US regulators tend to think if the asset has US ties, they have jurisdiction. Another thing Anthropic doesn't want is regulators accusing them of "knowing but not acting."

Host: So legally, Anthropic can't "pretend not to see"; once they know about these markets, they must act.

Dio Casares: Yes.

Host: How big is this market? Tens of billions for Anthropic alone? What percentage is unhealthy dark market vs. the entire market?

Dio Casares: This is basically all of the private side. Private also has many forms: a few family offices pooling to invest, vs. brokers, vs. firms like us raising and charging fees, completely different. Plus brokers are layered: a first-layer broker knows many buyers, also knows another broker who actually has the shares. So the market structure is complex, and money is huge.

An interesting data point: private fundraising now exceeds IPO fundraising, has been for years. Recorded secondary market trades plus financing rounds are over $200 billion. Considering fees aren't a few basis points but like the Anthropic deals we see: one-time 10% plus long-term cuts, if $10 billion comes through such channels in a round, the fee pool alone is $1 billion.

Host: I recently saw two social media posts reflecting the market's craziness. One was a San Francisco guy on Hinge writing "I know someone at Anthropic, dates zero commission," using Anthropic stock access to attract dates. Another was a woman tweeting "I just brokered one Anthropic secondary deal, made more than my entire 20s salary combined, this is insane." This is the social elite in San Francisco gaming around Anthropic shares. How does this happen?

Dio Casares: I actually spoke with the person who tweeted that. From a buyer's perspective, you want Anthropic, but the charter and agreements aren't public, hard to get. You can't just go to Anthropic and say "I want to buy $1 million in this round, thanks." This is a market built on internal connections. Some have shares and sell shares; some have buyer resources and sell those; a few do both. That's its market structure.

Even people inside funds make more money from this secondary trading than from their main investment business, so many are shifting into this market.

Host: So people see Anthropic equity as a goldmine, and a bunch are selling picks and shovels.

Dio Casares: Yes, and competition is much fiercer now, which is good. A few months ago, there was no real competition; most were just middlemen, not directly connecting sellers. Now more people can find both sides, handle the whole process, more professional. But simultaneously, fee rates are coming down.

Another risk many don't realize: sometimes you can't get shares from investors, so you buy employee forward contracts. This blew up recently. A well-known institution sold a forward contract on an xAI employee; that employee was later named in xAI's lawsuit against OpenAI, accused of corporate espionage, all his shares reclaimed by the company. Result: money paid, fees taken, but a mess. All buyer brokers 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 think these "fake SPVs" will increase; this will evolve into a game of reputation, seeing who can build investment vehicles that don't blow up.

10-20% of Deals Involve Fake Stock Certificates

Host: Let's talk about why an investment vehicle blows up. I understand it's nested SPVs, layer two, three, four, each layer taking fees, each layer down increasing uncertainty about whether the corresponding equity actually exists.

Dio Casares: Two or three-layer SPVs exist because of "buyer-seller mismatch." An $8 million seller rarely has a perfect $8 million buyer; might be three buyers piecing together. Most in this space aren't licensed brokers who can charge fees and pass through. But if you set up a fund, you can charge a front-end management fee for managing the fund; fees are taken at the SPV level.

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

Dio Casares: Better than nothing. Because at least you have tax filings, if managed properly. Anthropic is also publicly saying which fund admin services they recognize. They specifically named Sidecar, interesting because others are brokers for funds or SPVs; Sidecar is just a fund administrator. Naming Sidecar is because Anthropic thinks Sidecar's due diligence is insufficient, basically approving after seeing a document that "looks okay."

Back to your risk point: first, the equity isn't real at all; certificates can be forged—that's outright fraud. We've seen at least 10 such cases, confirmed fake after checking transfer records, but there's little you can do besides whistleblowing. Sometimes you can't tell if they faked it themselves or are reselling fakes. There is fraud, but I don't think it's as widespread as rumored; maybe 10%-20% of closed deals are fraudulent. More common isn't fraud but claiming to have shares without having them, taking money first then trying to invest in the company, often failing.

Host: Is there "unintentional fraud," where someone tries hard but because the market is like this, they don't actually get the promised asset? Is there a gray area?

Dio Casares: That's "gross negligence." Not much gray area. Pitchbook, shareholder lists, other resources for due diligence—these should be used when directly dealing with sellers. If you don't do due diligence on your buyers or clients, that's negligence; shouldn't happen. If you buy from a reputable seller with shareholder list access, documents reviewed, and they still do something shady, that's different, but the market has reputation; unreliable people are known in the circle.

Lawsuits and Locked Stock Disputes That May Erupt Post-IPO

Host: Post-Anthropic IPO, how does this speculative market "collapse"—not bad collapse, but settle, distribute shares, cash changes hands.

Dio Casares: Two main things: first, DTCC-level broker accounts and AML procedures; second, each fund's distribution terms. Some funds have full discretion on when to distribute; some stipulate distribution in-kind or cash immediately upon IPO and liquidity.

Imagine a three-layer SPV: first layer gets stock first, asks underlying LPs if they want in-kind or cash; all LPs in second layer say stock, pass it up; depends on DTCC, normally days, banks might take two weeks—that's two weeks delay. Then second layer asks its LPs cash or stock, pass to third layer, another 3 days to two weeks.

At any intermediate layer, if distribution rules allow GP discretion—e.g., Anthropic opens, stock soars, first layer GP says "I have long-term carry, I want it to rise more"; or conversely, opens crashes, doesn't want to deliver immediately, wants to hold months longer. If that happens, everyone downstream doesn't get stock. Also, people hedge their long positions in public markets, technically gray area. You might have thought delivery in 6 months, but have to wait another month. Many lawsuits will emerge here.

Host: Sounds like Anthropic itself doesn't care much, because for them, stock is issued, top SPVs handle it.

Dio Casares: Yes. Post-listing, company no longer needs private transfer agents, only used them for initial issuance, then everything goes through DTCC, they basically step out. But many brokers and banks might look at these trades and say, "Anthropic declared this invalid, we need to check if we can sell for you." Could be messy.

But from a game theory perspective, post-IPO, companies basically won't chase down problematic shares anymore; they won't do another private round, so the original motivation to maintain market order disappears.

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

Dio Casares: Lawsuits will take years; some cases will drag for years. Total amount? I'm not sure, I think nobody knows. But this will be the "awakening moment" for this market.

I spoke with someone from a small European family office recently, quite sad. I believe they invested in the problematic deal mentioned earlier, money ultimately returned. But I believe that GP didn't tell LPs, took the returned money trying to keep playing, betting on Anthropic's appreciation. This is common: using returned money as trading principal to bet on gains; unless they can make 500% returns, they can't fill the hole. I'm not optimistic they can. That loss will be borne by the fund itself.

Host: Your concern is: some people subjectively want to do well but mess up, e.g., buy fake equity. But why, after messing up, would they still have client money?

Dio Casares: Yes, or negligence occurs. My intuition is the fee structure for that block was heavy, GP took the money, ended up with nothing to return to LPs; or for some reason, they think they can't return it. But finance doesn't work like that; after a screw-up, someone must say "I'm very sorry this didn't work out, here's your money back."

Host: So the error path is: you raise money from friends/family, set up an SPV, it has money; you get a verbal promise from someone else to deliver shares. Then you have two choices: do nothing, keep money in SPV waiting for shares; or count chickens early, "I just made a lot, buy a house, a Porsche," then on delivery day find no shares, but money spent, nothing to return.

Dio Casares: Exactly.

Host: Let's zoom out. The private market is huge, companies IPO later, money changes hands privately, gradually becoming its own internal market—the opposite of public markets, yet the coolest companies stay here longer. How will this market evolve?

Dio Casares: Saying "completely unregulated" isn't fair; regulation exists but is "wild" and not strictly enforced. Unless obvious fraud, regulators mostly don't bother, and they can't keep up. Should FINRA chase someone for incorrect filing or illegal fundraising? Most would say illegal fundraising. Sometimes it's the same people doing both.

Markets repeat similar patterns. This is like that phase in crypto with low float, high FDV: limited supply creates crazy moves, making it easier for companies to raise. This cycle has real tech behind it; I use Claude myself, their revenue is already substantial.

Interesting are existing large institutions; banks have or partner with secondary desks, they are very cautious, can't keep up with this market's pace. So you see a wave of new firms filling the gap. Simultaneously, large funds also do SPVs, just structured differently, only for their own LPs. This trend is capital moving from "giving to funds for unified management" to "directly managed capital." I think this continues until this cycle ends. A bunch of people will buy vehicles equivalent to "locked tokens" and lose a lot, finally saying "okay, I'll put money back into VC funds." This wave of hot money will go elsewhere, but the US secondary market will become more professional.

Patagon's Strategy and Philosophy

Host: Back to what you're doing at Patagon. From your experience and knowledge in secondary markets, introduce Patagon's strategy and philosophy.

Dio Casares: Initially we only did proprietary, getting into trades. Then a friend paid me a fee once, I asked why. He told me another broker would charge him two to three times more; what he paid me was the savings. I realized, growing up in the Bay Area, I know many people, know who to call, how to background check, while many of my friends are international, not as connected in San Francisco. I started doing this part-time, then gradually saw it could be a business, especially around brand and process.

Look at platforms like Forge, Hive; they don't verify if equity is real, don't vet buyers, don't collect KYC (here referring to marketplace business, their own direct investment opportunities are different), but still charge 3.5%. Just giving you an intro, a fake order book, you still have to email negotiate, and they charge 3.5% on the deal. We think that's outrageous.

What we do: find deals ourselves, set up investment vehicles ourselves, do our own due diligence; ensure equity is real, structure compliant. Clients can invest in these deals directly on the platform, no need to negotiate price first, then ask for vehicle docs, sign, email back and forth for wiring. Everything in one place; ultimately we even let clients use positions for credit financing. We want to provide value far beyond "get you into this one and leave you."

We've done complex deals, like a crypto company, all employee forward contracts. During due diligence, we background-checked each employee: gambling issues, acquaintances giving negative feedback. We found one problematic, didn't work with that person, others were fine, whole deal completed smoothly.

Host: This in turn builds your credibility; when trying to get Anthropic secondary or other shares, you can say "our client base is quality-screened."

Dio Casares: Precisely. We can also tell clients "we've handled difficult deals." For that deal, there was no other authorized access in the market; we got clients in where others couldn't. Clients appreciate you, naturally come to you next time.

Legal Risks of Tokenized Equity and Pre-IPO Perpetual Contracts

Host: If a listener has already bought Anthropic secondary or other company secondary but knows nothing about the underlying authenticity, what advice or action do you have?

Dio Casares: Hard to generalize, market structures vary too much. Some now hold perpetual contracts; while I personally don't recommend, ironically perps are derivatives, fall under a completely different legal subclass, so risks less obvious. Funding rates might be aggressive, but that's the price you pay for it to align with IPO open price.

If you're a small buyer with $100k to $1m in some "tokenized version of Anthropic" or similar vehicle, most of the time you can't peel back layers to see the underlying fully. At best, you see the vehicle your money goes into, and that's usually the second or third layer. I'd advise not adding more; if your gut feeling about this position is really bad, generally I trust intuition, exit.

Host: The tokenized perpetual contracts you mentioned—do they have real claims on underlying equity, or are they just predictions/subjective mappings?

Dio Casares: Several institutions are doing this now; mechanisms differ, but the idea is once these go live, pre-IPO perpetual funding rates will be crazy. Pre-IPO perps are different from regular perps because market makers already have underlying trades as hedges, hedging methods differ from US equity market structure, but eventually it converges to a real stock, allowing arbitrage. So as IPO nears, perpetual contract prices and funding rates converge to "normal market" levels.

Host: Any topics I didn't ask about?

Dio Casares: I think we covered it quite comprehensively.