KEYTAKEAWAYS
- CZ’s early Bitcoin bet made him wealthy, but crypto’s biggest missed opportunity came later with AI.
- FTX’s stake in Anthropic could have been worth over $27 billion, reshaping Crypto–AI relations.
- The failure to retain AI exposure left crypto sidelined as traditional finance captured the upside.
CONTENT
From CZ’s early Bitcoin gamble to FTX’s lost Anthropic stake, this story explores how crypto missed its biggest chance to shape the AI era — and the billions left on the table.
In 2014, just 1 year after first encountering the concept of cryptocurrencies, CZ made one of the boldest investments of his life — selling his apartment in Shanghai and going “all in” on around 1,500 BTC at a three-digit price.
12 years later, had CZ never sold, this investment would have generated more than $100 million in profits, with peak returns reaching approximately $189 million.
Compared with his later achievement of founding Binance and rising to become an industry leader, the financial gains from this early bet may seem insignificant to CZ himself. But from an outside perspective, this idealistic, all-or-nothing decision remains one of his most widely admired moves.
Ironically, however, even someone as decisive and conviction-driven as CZ once missed an opportunity — in a highly dramatic way — that could have delivered returns hundreds of times greater than his famous “sell-house-for-Bitcoin” bet.
FROM AN OVERLOOKED SIDE BET TO THE CENTER OF THE AI SPOTLIGHT
In April 2022 (the official announcement date; the deal was actually completed in 2021), FTX made its most important investment in the AI sector — leading Anthropic’s $580 million Series B round with a $500 million commitment. At its peak, FTX held a 13.56% stake, later diluted to 7.84% after multiple subsequent funding rounds.
At the time, AI’s transformative potential had yet to fully materialize. Just 6 months later, in November 2022 — the same month FTX collapsed — OpenAI launched ChatGPT, marking the irreversible beginning of the AI “Age of Exploration.” Meanwhile, Anthropic, powered by its Claude series (especially the developer-focused Claude Code), repeatedly stunned the world and gradually emerged as one of the brightest stars of the AI era.
As Claude continued to evolve, Anthropic’s valuation soared. Capital flooded in, with investors eager to secure a seat on its IPO-bound ship. According to the latest market rumors, Anthropic is in the final stage of a massive new funding round, expected to exceed $20 billion (originally planned at $10 billion but potentially doubling due to overwhelming demand), with a valuation reaching as high as $350 billion. The deal may close as early as this week.
Based on this valuation, FTX’s former stake in Anthropic would now be worth approximately $27.44 billion — more than enough to cover, several times over, the reserve gap that ultimately led to its bankruptcy. But history cannot be rewritten, and the outcome was long sealed.
It is hard not to acknowledge SBF as a rare venture capital talent. Beyond Anthropic, he also invested at the seed stage in today’s rising star, Cursor. Yet he was clearly not a qualified business operator, especially when it came to risk management.
CZ, by contrast, represents the opposite profile. He is an exceptional operator, and Binance’s dominance owes much to his repeated strategic successes. Still, CZ has often stated that he is not a traditional return-driven investor — he does not speculate aggressively and sees himself more as an industry builder than a pure profit seeker.
A RUSHED ENDING: WHAT COULD HAVE BEEN CRYPTO’S GREATEST LINK TO AI
You might wonder: 🔍what ultimately happened to FTX’s equity holdings?
The answer is straightforward. After FTX’s bankruptcy, all assets — including the Anthropic stake — were placed under the control of the bankruptcy administration team. In February 2024, the court approved the sale of these shares. In March and June of the same year, the team sold 29.5 million shares and 15 million shares for a combined total of over $1.3 billion.
The buyers were primarily Abu Dhabi–based ATIC Third International Investment and Wall Street institutions such as Jane Street and Fidelity. In other words, no crypto-native company ended up sharing in this windfall.
Whether these assets were deliberately undervalued, or whether there were hidden interest transfers under the guise of bankruptcy liquidation, is no longer central to the crypto industry.
What truly matters is this: this could have been the strongest intersection between Crypto and AI.
In another timeline, whether these shares were held by SBF or CZ, if a leading crypto institution had maintained meaningful influence in the most successful AI company of this era, the “Crypto + AI” narrative might have produced far more ambitious experiments — and possibly unexpected breakthroughs.
Those left slapping their thighs in regret are not only CZ.
