Michael Saylor says he used ChatGPT to help design a Bitcoin (BTC)-backed preferred stock. It raised over $15 billion for Strategy, a financial instrument nobody in history had built before.

Speaking with Steven Bartlett on The Diary of a CEO, Saylor also defended a recent Bitcoin sale. He then doubled down on a bold Bitcoin price prediction stretching two decades.

ChatGPT used as a historic $15 Billion funding tool

By early 2025, Strategy already held about $30 billion in Bitcoin. It had also become the largest issuer of convertible bonds in the world, maxing out that market. Saylor needed a new instrument, so he turned to OpenAI’s chatbot.

“We go to the AI. We said, well, can we do it? They’re like, of course you can do it. Just do this, this, and this, and this, and that,” Michael Saylor, Executive Chairman, Strategy, said on YouTube

The result was STRK, a convertible preferred stock, followed by a version with a variable monthly dividend rate.

“In the history of the world, no one ever created a variable dividend rate preferred stock,” Saylor said.

That structure helped raise $10.5 billion from one instrument, plus roughly $4 billion more, totaling the $15 billion Saylor credits to AI.

Why Saylor Sold BTC

Short sellers argued that Strategy owned too much Bitcoin, near 4% of the supply, to ever sell without crashing the asset or its own stock. That belief threatened the dividends behind Strategy’s credit instruments.

“If you want people to believe that you can do a thing, you have to do the thing.”

Saylor said.

Saylor sold Bitcoin near $59,000 in response, and the price rose afterward. Strategy later confirmed a sale of more than 1,600 Bitcoin in one week, even as Saylor insisted he has personally never sold a token. The move also eased concern about Strategy’s growing preferred stock load, which analysts said was straining the firm’s Bitcoin flywheel.

“It turns out that the break even point for us is about 3.2%,” Saylor noted.

Bitcoin trades near $64,500 today. Saylor still expects it to climb 30% annually for two decades, then slow to roughly 20% a year.

“I think it appreciates about 30% a year for the next 20 years… And then it’ll slow down to being appreciative about 20% a year.”

Compounding at that rate for 20 years would push BTC from today’s price toward roughly $12 million by 2046, based on Saylor’s own math.

However, that timeline has skeptics. Strategy’s own stock has repeatedly failed to crack $150 this year. Macro trader Arthur Hayes ties any run toward seven figures to an AI credit bust, not corporate buying.

Still, Saylor’s core message stayed consistent throughout the interview. Entrepreneurs should stop competing with tasks AI already handles, he said, and instead ask it questions nobody has asked before.