If FTX hadn’t sold Anthropic back then, today’s valuation might not be $13 billion, but hundreds or even thousands of billions of dollars. Anthropic’s latest prospectus reveals plans to list on Nasdaq at a price range of $70–$78 per share under the ticker symbol ANT, with Goldman Sachs and Morgan Stanley serving as lead underwriters. Under the current offering structure, the IPO implies a valuation of approximately $917 billion to $1.02 trillion; if calculated on a fully diluted basis, the high end could reach as much as $1.4 trillion. But the most fascinating story behind this IPO isn’t just how much wealth the AI company has created—it’s what FTX missed. Between 2021 and 2022, Alameda Research invested approximately $500 million in Anthropic, acquiring roughly 7.84% of its shares. Later, after FTX collapsed, its bankruptcy estate was forced to sell these shares in two tranches in 2024 to repay creditors, recovering a total of about $1.34 billion. From an investment perspective, this was already a highly successful transaction—turning $500 million into $1.34 billion, a return of roughly 2.68x. But the problem? They sold too early. Had they held onto the shares, and assuming the original 7.84% stake remained unchanged, Anthropic’s $1.4 trillion valuation would make this portion worth approximately $109.8 billion—transforming the initial $500 million investment into nearly $110 billion. Of course, this is a static assumption. After subsequent funding rounds diluted ownership, the original stake’s proportion has dropped to about 2.5%. Based on the latest IPO valuation, the actual theoretical value is closer to $30 billion. Even so, this remains an investment that could have fundamentally altered the fate of FTX’s creditors. There’s a very real investment lesson here: Bankruptcy liquidation and long-term investing are two entirely different games. At the time, FTX needed cash liquidity—not to hold onto an unlisted AI company with an uncertain future. In that context, selling the shares wasn’t necessarily a wrong decision. After all, no one could guarantee Anthropic would grow to its current scale. But looking back today, this transaction stands as perhaps the most expensive early exit in crypto history. The cruelest truth about investing is this: you must not only decide what to buy, but also whether you can hold on.