Saylor says ChatGPT helped Strategy raise $15 billion in a year

NewsThu, 06 Aug 2026 20:50:33 UTC1 hour ago
Saylor says ChatGPT helped Strategy raise $15 billion in a year

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.

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