Michael Saylor told the Diary of a CEO podcast that a preferred-stock product he designed with ChatGPT let his company raise roughly $15 billion over the past year. 

Saylor’s advice to entrepreneurs is to stop competing with machines and start directing them.

How did ChatGPT help Michael Saylor make $15 billion? 

Michael Saylor, the 61-year-old executive chairman of Strategy, the firm formerly known as MicroStrategy, framed AI as a partner rather than a rival during his conversation with the host of the Diary of a CEO, Steven Bartlett. 

“Don’t try to outwork the robots,” he said. “What you want to do is ask the AI to do something that’s never been done before.” 

Saylor said during the interview that both Bitcoin and AI technologies are early in their adoption and that companies pairing the two will build financial products that do not yet exist.

Microsoft’s CEO, Satya Nadella, has also described AI in a similar way, calling it a “co-pilot” at Davos in 2023. Mark Cuban has also argued that entrepreneurs using AI could create outsized wealth.

Saylor revealed during the podcast that ChatGPT helped him raise $15 billion. His company, Strategy, had been using convertible bonds to fund Bitcoin purchases, but eventually hit the practical limit of that approach. 

Saylor said he went back and forth with ChatGPT for hours, testing whether a monthly preferred stock that stayed stable near $100 was possible. The AI told him no one had ever done it before, but it was legal and reasonable. Bankers and lawyers also pushed back at first because nothing like it had been sold before.

The resulting preferred stock is one that was designed to bridge debt and equity while still financing more Bitcoin buying called STRK. The AI helped structure STRC as a Bitcoin-backed convertible preferred stock. It also suggested ways to adjust the dividend rate each month, which helps keep the market price close to its $100 par value. 

The $15 billion figure represents the capital raised by the company, not personal profit earned by Saylor. Forbes estimates his personal net worth at $3.3 billion. 

Why is Strategy now selling Bitcoin?

Bitcoin has fallen 26% in 2026, while Strategy shares are down about 38% from the start of the year. The stock is trading near $98, down roughly 76% from its 52-week high of $414.36. 

Strategy has also sold its Bitcoin for the third time, Cryptopolitan reported, recently offloading 1,638 Bitcoins for about $104.7 million at an average price of $63,957 each. Combined, Strategy has sold approximately 5,226 BTC for roughly $321 million to cover preferred dividend payments. 

Strategy also raised $290.6 million by selling common shares and added $250 million to its cash reserve, which now stands at $4 billion. The reserve is designed to cover at least 12 months of the company’s preferred dividend and interest obligations, which total about $1.76 billion per year. 

Strategy still holds 842,138 Bitcoins at an average cost of about $75,419 per coin. With Bitcoin trading below that level, the company is sitting on a multibillion-dollar unrealized loss. Its second-quarter results included an $8.32 billion unrealized loss tied to falling Bitcoin prices and a diluted loss of $24.45 per share. 

Saylor has resisted the idea that he abandoned his stance, writing on X, as Cryptopolitan quoted him, “We have never had a ‘never sell’ policy.”

Notably, during the dot-com era, MicroStrategy’s stock surge made Saylor a billionaire. But the company later restated its results and disclosed that its 1999 revenue had been overstated. The stock lost 62% of its value in one day, and Saylor later settled SEC charges by paying $8 million without admitting wrongdoing.

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