Michael Saylor Says ChatGPT Helped Strategy Raise $15B

Strategy Executive Chairman Michael Saylor says ChatGPT helped design preferred-stock structures that raised about $15 billion, extending the company’s Bitcoin(BTC) financing beyond convertible debt.

Key Points:

• Saylor said ChatGPT helped Strategy develop preferred-stock structures after the company reached the limits of the convertible bond market.
• He credited the AI-assisted approach with helping raise roughly $15 billion and repeated a Bitcoin forecast near $12 million by 2046.

Saylor AI Financing

Speaking with Steven Bartlett on The Diary of a CEO, Saylor said Strategy turned to OpenAI’s ChatGPT after becoming the world’s largest convertible bond issuer and maxing out that market. By early 2025, the company already held about $30 billion in Bitcoin.

“We go to the AI. We said, well, can we do it?” Saylor said. Strategy first introduced STRK, a convertible preferred stock, then followed with a preferred security carrying a variable monthly dividend rate.

“In the history of the world, no one ever created a variable dividend rate preferred stock,” Saylor said. He said one instrument raised $10.5 billion and roughly $4 billion came from related financing, taking the total to about $15 billion.

Saylor also defended Strategy’s Bitcoin sale after short sellers questioned whether the company could liquidate holdings without hurting the market. “If you want people to believe that you can do a thing, you have to do the thing,” he said. Strategy later sold more than 1,600 Bitcoin in one week, and Saylor said, “It turns out that the break even point for us is about 3.2%.”

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Bitcoin Price Outlook

Saylor remains highly bullish on Bitcoin despite the sales. “I think it appreciates about 30% a year for the next 20 years,” he said, adding that he expects growth to slow to roughly 20% annually afterward.

At roughly $64,500 at publication, that path would put Bitcoin near $12 million by 2046. The forecast remains speculative, while Strategy shares have struggled to break above $150 this year and macro trader Arthur Hayes has tied a possible seven-figure rally to an AI credit bust.

The interview reflects a shift in Strategy’s financing model. After relying heavily on convertible bonds, the company expanded into preferred securities and later showed it would sell Bitcoin to support that structure, while Saylor maintained that he has never sold his personal holdings.

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