Michael Saylor says ChatGPT helped him raise $15B for Strategy's Bitcoin bet

Michael @saylor used @ChatGPT to engineer a financial instrument that Wall Street had never seen before, and it went on to raise roughly $15 billion for @Strategy's $BTC treasury. He detailed the process in a new episode of the Diary of a CEO podcast with host Steven Bartlett, published on August 6, 2026.

An Instrument Lawyers Said Could Not Exist

After Strategy exhausted more conventional routes for raising capital, Saylor turned to OpenAI's chatbot with a specific and unconventional brief. A standard preferred stock trading near its par value normally requires a fixed dividend, making the price sensitive to interest rates. Saylor wanted the price stable and the dividend variable, resetting monthly, which had never been done before. Lawyers and bankers were hesitant, telling him they had never seen it done before and were not sure it could be done. ChatGPT, he said, worked through the structure with him until a viable design emerged.

The resulting instrument came to market as a $2.5 billion IPO, which Saylor described as the biggest IPO of the year to date at the time. Strategy then filed a shelf registration and sold an additional $8 billion of the same security, plus roughly $4 billion of other instruments, bringing total proceeds to around $15 billion.

Don't Try to Outwork the Robots

Beyond the capital-raising story, Saylor used the interview to share a broader view of how builders should think about AI. His argument is that the competitive edge does not come from learning what AI can already do, but from asking it to do things that have never been tried. "Don't keep doing the same thing over and over, working harder and harder every year, fighting against the modern automation epidemic," he said during the interview.

The remarks come at a complicated moment for Strategy. The company's total obligations have grown more than threefold over the past year, driven almost entirely by roughly $15 billion in preferred stock offerings. Strategy's Bitcoin-heavy approach and its use of preferred stock to fund further purchases has left the company increasingly tied to the cryptocurrency's price, a structure Fortune has described as carrying significant leverage risk. Saylor has maintained that Bitcoin appreciation is sufficient to service those obligations over time, but the position remains closely watched by markets.

Sources:
Fortune: Michael Saylor says he made $15 billion with ChatGPT (August 2026)
Fortune: How Saylor's preferred stock gamble could trigger a death spiral for Strategy (June 2026)
Diary of a CEO interview transcript via Singju Post