by Coinstrooper Crypto Articles
Quick Take
  • The same venture bets that helped build Sam Bankman-Fried’s empire have become a case study in selling too early.
  • “That guy knew how to trade with his client’s money, he just ran out of time,” one user quipped.
  • Alameda Research wrote a $200,000 check into Anysphere, the maker of AI coding tool Cursor, during a 2022 pre-seed round.
  • With this, they secured roughly 5% of the company, according to Forbes’ accounting of the firm’s startup holdings.

What Happened

The scale of the miss became clear this week, after SpaceX agreed to a $60 billion all-stock deal to acquire Cursor, building on a call option the rocket company first secured in April 2026.

“He made all these bets at 29, while running a $32B exchange…The estate just wasn’t allowed to hold them. Say whatever you want. The man had the eye,” investor Sjuul added.

Market Context

However, the roughly 23-fold gap between the sale price and today’s value is the clearest sign of how distress selling clashed with frontier-tech timing.

Why It Matters

The same venture bets that helped build Sam Bankman-Fried’s empire have become a case study in selling too early.

As the FTX bankruptcy estate raced to repay creditors, it offloaded early stakes in companies that went on to rank among the most valuable names in AI and fintech, often for a tiny fraction of what they would later command.

Details

“That guy knew how to trade with his client’s money, he just ran out of time,” one user quipped.

The Cursor stake sold at cost

Alameda Research wrote a $200,000 check into Anysphere, the maker of AI coding tool Cursor, during a 2022 pre-seed round.

With this, they secured roughly 5% of the company, according to Forbes’ accounting of the firm’s startup holdings.

In 2023, the estate sold that position back at cost, treating a then-obscure developer tool as a minor asset to clear.

At that valuation, the discarded 5% stake would be worth about $3 billion. On paper, a position the estate let go for pocket change would now rank among the most valuable assets it ever touched.

“SBF’s sleepless prison nights just got worse… In 2022, Alameda (FTX) dropped $200k into Cursor pre-seed → ~5% stake at a ~$4M valuation. FTX bankruptcy sold the entire position back at cost. Today, that 5% would be worth $3B – a 15,000x return,” commented John LeFevre.

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Anthropic Defines the Regret

FTX poured about $500 million into Anthropic in 2021, one of the largest private checks written into an AI lab before ChatGPT existed.

This left it close to an 8% holding in the company founded by former OpenAI researchers Dario and Daniela Amodei.

With court approval, the estate sold that stake in two 2024 tranches:

About $884 million to a group of institutional buyers in March and

A further $452 million that June, for roughly $1.3 billion combined.

Anthropic has since raised a $30 billion round at a $380 billion post-money valuation, per the company’s own disclosure.

That same 8% stake would now be worth more than $30 billion, an exit BeInCrypto flagged as a multi-billion-dollar miss while Bankman-Fried sat in prison.

The proceeds still helped push creditor recoveries toward full repayment.

Robinhood, Solana, Sui Round out the List

The pattern repeats across SBF’s other forced exits.