Saylor: ChatGPT helped Strategy raise $15 billion
Michael Saylor says ChatGPT helped Strategy design STRK, a preferred stock that unlocked about $15 billion in capital in 2025.
Michael Saylor, founder and executive chairman of Strategy, told host Steven Bartlett on The Diary of a CEO podcast that the company used ChatGPT to design STRK, a preferred stock structure that unlocked about $15 billion in capital in 2025.
Saylor told listeners that Strategy had reached the practical limit of issuing convertible bonds to fund additional bitcoin purchases and needed a new financing option. He noted lawyers and investment bankers resisted unfamiliar structures. The company used ChatGPT to test alternative designs and settled on STRK, which Saylor described as a preferred stock format that sits between debt and equity and attracted the funds the company sought.
On the podcast he said, “We used AI to make $15 billion last year,” and added that the generative model produced ideas that led to the final product.
Saylor linked bitcoin and artificial intelligence, calling bitcoin “digital capital” and AI “digital intelligence.” He described bitcoin as a scarce, transferable asset and said AI expands human productivity. He advised business leaders to use AI to create new products rather than compete with automation, saying, “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.”
He reiterated his view that fiat currencies lose purchasing power over generations and that scarce assets can preserve value. He contrasted residential real estate, where taxes, insurance and maintenance often reduce long-term returns, with commercial property, where rental income can offset operating costs. He noted bitcoin can be moved across borders in seconds without multiple intermediaries.
Saylor predicted many knowledge-work tasks, including accounting, legal research and document preparation, will be automated and that future roles will focus on directing AI systems. He described plans for Strategy to combine its bitcoin holdings with AI tools to develop new financial products and to support the company’s next phase of growth.
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