Michael Saylor has claimed that ChatGPT played a pivotal role in helping Strategy develop a new financing structure that ultimately helped raise roughly $15 billion in capital for additional Bitcoin purchases.
Speaking during a recent interview, the Strategy executive said the company turned to artificial intelligence after reaching the limits of its traditional financing options.
According to the boss, the firm had already become one of the largest issuers of convertible bonds tied to its Bitcoin strategy and needed a new type of security to continue expanding its treasury position.
Saylor explained that by early 2025, the company had largely maxed out the equity and convertible bond markets to fund additional Bitcoin acquisitions. That forced Strategy to search for an alternative instrument that was neither ordinary common stock nor a conventional bond.
He described the goal as creating a hybrid preferred security with customized terms that combines elements of debt and equity and is suitable for a Bitcoin-focused treasury company.
 
Notably, according to Saylor, the company used OpenAI’s ChatGPT to explore possible structures for the new instrument. He said the AI helped evaluate legal, financial, and structural possibilities for what became the STRK convertible preferred stock.
The executive emphasized that no one had previously created a Bitcoin-backed preferred stock with the specific features Strategy wanted to include.
Saylor also said the AI suggested ways to implement features that bankers and lawyers initially viewed as unconventional, including mechanisms intended to help the instrument trade more like a short-duration credit product than a volatile equity security.
Meanwhile, the Strategy chairman stated that the preferred stock launch became a $2.5 billion initial offering, followed by additional sales through a shelf registration. Combined with other financing instruments, he said the company ultimately sold about $15 billion in credit-related securities, which he equated with roughly $15 billion allocated to the company’s Bitcoin strategy.
“Yeah. Because the short of it is we brought that IPO to market. It became a $2.5 billion IPO, the biggest IPO of the year to date. And then we put a shelf registration on it. We sold another $8 billion of it,” Saylor stated.
“So, we sold 10.5 billion of that instrument plus 4 billion of the other instruments. So, we basically sold $15 billion of credit, which kind of equates to the company making about $15 billion,” he added.
Nonetheless, while Saylor framed the achievement as evidence of AI-assisted innovation, he acknowledged that the transaction also required substantial legal and financial engineering work.
Saylor also used the discussion to argue that entrepreneurs should focus on asking AI to solve problems that have not previously been solved rather than simply automating existing work. He said the opportunity lies in combining domain expertise with AI-generated exploration of unconventional solutions.
“I used AI to make 15 billion dollars last year. Don’t try to outwork the robots. What you want to do is ask the AI to do something that’s never been done before.”
That said, the comments come as Strategy remains one of the most closely watched corporate holders of Bitcoin, with investors continuing to scrutinize both the company’s treasury strategy and the increasingly sophisticated financing structures being built around it.
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