Michael Saylor reveals how ChatGPT helped Strategy unlock $15 billion for its Bitcoin machine

Michael Saylor says Strategy used AI to design a new class of preferred stocks that ultimately allowed the company to raise roughly $15 billion for its Bitcoin strategy.

The Strategy executive chairman said he turned to AI after the company’s existing financing channels, including common-stock sales and convertible bonds, were becoming harder to scale.

“I used AI to make $15 billion last year,” Saylor said during an Aug. 6 appearance on The Diary of a CEO podcast.

Saylor was referring to capital raised through securities rather than $15 billion of personal income or corporate profit. He said Strategy ultimately sold about $10.5 billion of one preferred-stock instrument and another roughly $4 billion across related products.

He did not initially identify the AI system by name. Later in the discussion, after Saylor described asking an AI how Strategy could structure an unusual variable-dividend preferred stock, host Steven Bartlett asked whether he meant ChatGPT and OpenAI. Saylor affirmed the characterization.

Strategy turned to AI after its old Bitcoin playbook hit limits

According to Saylor, the experiment began in early 2025 as Strategy searched for another way to finance Bitcoin purchases.