I just read something fascinating about how a failed AI investment could have been worth a fortune. It turns out that around 2021, Dario Amodei founded Anthropic to compete with ChatGPT, and a year later, capital arrived: a certain crypto exchange led by an enthusiastic AI risk entrepreneur decided to invest 500 million in a new funding round, obtaining about a 13.56% stake that was later diluted to approximately 8%.

The interesting part is that all of this was financed with client funds, something that eventually came to light very publicly. When the 2022 bear market hit, the collapse was brutal: that exchange went bankrupt in November, and its CEO was sentenced to 25 years in prison. The case was widely documented across multiple industry sources.

But here’s what’s got me thinking: when the liquidation team started selling assets in 2024 to compensate creditors, they discovered that the stake in Anthropic was one of the crown jewels. They sold two-thirds to sovereign funds and netted around 884 million dollars. In total, they recovered between 1.3 and 1.4 billion of their original investment.

Now, look at what happened to Anthropic afterward. The AI wave hit hard, Amazon and Google invested massively, and the valuation skyrocketed. It’s currently negotiating a new funding round with an estimated pre-money valuation of 350 billion dollars. If that 8% stake had remained intact, it would have been worth approximately 28 billion dollars or more.

The irony is that if that exchange hadn’t collapsed, its CEO could have been one of the richest billionaires of this AI era. Instead, that stake ended up being what saved many affected creditors, while he himself is in prison watching his potential fortune evaporate. The story of how a bet on AI ended up being the biggest asset in a bankruptcy is a reminder of how volatile all this can be in the world of crypto and technology.