
Playbook
Tasteful Skills
“Tasteful Skills” argues that the best agent skills are not documentation or best-practice lists.
Anthropic just declared many gray-market share deals void — its lawyers said any transfer without board approval “will not be recognized,” and explicitly stated that SPVs holding Anthropic stock are prohibited.
The private-market frenzy got absurd because Anthropic’s numbers got absurd — Matthew Berman cites Dario saying revenue grew 80x this year, helping push private-market valuation chatter from roughly $300 billion to above $1 trillion.
Middlemen turned Anthropic secondaries into an opaque fee stack — Berman walks through employees selling to buyers, buyers bundling shares into SPVs, and resellers layering more SPVs on top, with fees ballooning from a normal 2% to 10% or more.
Some well-known secondary platforms were called out by name — Anthropic’s notice flagged firms including Forge, Hive, Sidecar, UpMarket, OpenDoor Partners, Unicorns Exchange, Pachamama, and Lionheart Ventures as unauthorized.
Berman’s bigger point is about access, not just legality — he argues average investors are shut out of companies like Anthropic, OpenAI, and xAI while insiders and wealthy funds capture what he frames as generational AI wealth creation.
The money is already reshaping real life in San Francisco — he points to Anthropic allowing 600 employees to sell $6.6 billion in stock, about $11 million each on average, alongside Bay Area homes selling hundreds of thousands over list.
Berman opens with the bombshell: Anthropic’s lawyers warned that unauthorized secondary share sales are void. He immediately ties it to his own near-miss buying Anthropic secondaries, saying he regretted passing until this notice made clear a lot of these deals may never have been valid in the first place.
He frames Anthropic as maybe the fastest-growing private company ever, with valuation talk jumping from around $300 billion in February to north of $1 trillion. The fuel was explosive demand around AI and Dario’s claim that Anthropic’s revenue grew 80x this year — the kind of number that creates instant feeding frenzies in private markets.
Berman explains the basic trade: an early employee wants liquidity, sells shares, a buyer aggregates them, then stuffs them into an SPV to resell access. The problem is that one SPV often gets wrapped in another and another, so by the time the end investor arrives, they’re paying 10%+ in fees, staring through fog, and barely know what they actually own.
He reads the legal language plainly: if Anthropic didn’t approve the transfer, the buyer is not a stockholder and gets no rights. The sharpest line is that Anthropic does not permit SPVs to acquire its stock at all, which Berman says effectively slams the door on a huge chunk of private-market demand and helps explain the sudden drop in secondary valuation.
Anthropic’s warning lists classic red flags: unsolicited messages, “exclusive access,” crypto or wire payments, pressure tactics, and anyone claiming they found a workaround to company restrictions. Berman says the board-approval issue is the real killer, then notes Anthropic explicitly named OpenDoor Partners, Unicorns Exchange, Pachamama, Lionheart Ventures, Hive, Forge, Sidecar, and UpMarket — including some firms that are otherwise legitimate players in secondaries.
Things get almost surreal when Berman recounts seeing VC Ash Arora publicly post that brokering an Anthropic secondary deal made her more money than her entire net worth from her 20s. He DM’d her asking for shares, the post vanished, and he says people warned that brokering securities without being a registered broker could trigger FINRA trouble — all capped with the darkly funny Forbes 30 Under 30 joke about alumni ending up in jail.
Berman zooms out and argues the scandal isn’t just shady SPVs — it’s that ordinary people can’t buy into Anthropic, OpenAI, or xAI while elite VCs and wealthy insiders can. He acknowledges the investor-protection rationale, but says the current setup is basically “the rich get richer,” especially now that giant firms stay private longer.
He closes on the spillover effects: Anthropic reportedly let 600 employees sell $6.6 billion worth of shares, around $11 million each on average, creating a fresh wave of multimillionaires. In Berman’s telling, that money is already washing into San Francisco real estate, with examples like a Sunset District home going for $900,000 over list, turning AI wealth concentration into something you can literally see in the housing market.
Share
Keep Reading
The Weekly Echo. The inbox-shaped summary of what mattered.
New editorials announced here.

Playbook
“Tasteful Skills” argues that the best agent skills are not documentation or best-practice lists.

Playbook
Learn how tasteful prompting helps you move beyond generic AI output by shaping context, style, and judgment from the start.

Playbook
OpenAI shipped /goal for the Codex CLI. It turns a prompt into a persisted, self-continuing contract.