SBF Sold Too Early: These Exited Bets Later Turned Into Multi-Billion Winners

The same venture bets that helped build Sam Bankman-Frieds 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. That guy knew how to trade with his clients 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 firms startup holdings. In 2023, the estate sold that position back at cost, treating a then-obscure developer tool as a minor asset to clear. 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. SpaceX has exercised the option to acquire @cursor_ai in an all-stock transaction with the goal of building the worlds most useful AI models.For the past few months, SpaceXAI has been jointly training a model with Cursor, which will be released in Cursor and Grok Build soon. 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. SBFs 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. Follow us on Xto get the latest news as it happens 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 companys 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. He made all these bets at 29, while running a $32B exchangeThe estate just wasnt allowed to hold them. Say whatever you want. The man had the eye, investor Sjuul added. The proceeds still helped push creditor recoveries toward full repayment. However, the roughly 23-fold gap between the sale price and todays value is the clearest sign of how distress selling clashed with frontier-tech timing. Robinhood, Solana, Sui Round out the List The pattern repeats across SBFs other forced exits. Emergent Fidelity Technologies, the Antigua-registered vehicle Bankman-Fried controlled, bought a 7.6% stake in Robinhood for about $648 million in 2022. After the collapse, US prosecutors seized the shares, and in 2023 the US Marshals Service sold 55.3 million of them back to Robinhood at $10.96 apiece, a $605.7 million deal. That same block would be worth more than $5 billion at Robinhoods current valuation near $87 billion. Solana (SOL) cuts closer to home, since Alameda had been one of the tokens earliest backers. Under a court-approved process in 2024, the estate sold roughly 30 million locked SOL at about $64 each, with Galaxy Digital and Pantera Capital among the largest buyers. SOL later peaked near $293 in early 2025 before sliding to about $74 today, which leaves those discounted Solana sales looking costly mainly against the 2025 highs rather than the current price. In a separate 2023 settlement, Mysten Labs bought back FTXs Sui (SUI) equity and token warrants for about $96 million, close to the roughly $101 million the exchange had paid a year earlier. Taken together, the exits trace a portfolio of early access to standout companies undone by a bankruptcy that forced quick sales to repay defrauded customers. Sam Bankman-Fried is the greatest investor of all timeThat means if he werent in jail today and still owned all this equity, hed be worth ~$100 billion Hed be top 20 richest people in the world, stated Alex Finn, Founder/CEO of Henry Intelligent Machines PBC. The estate, run by restructuring veteran John J. Ray III, needed cash on a court timeline rather than the patience a venture fund can afford. Whether it sold too cheaply or simply could not wait is a debate that sharpens with every new funding round and acquisition tied to its former holdings.