Michael Saylor asked ChatGPT to help him solve a corporate finance problem. The chatbot’s answer ended up raising $15 billion.
Strategy Inc., the company formerly known as MicroStrategy, used AI-designed credit instruments to raise roughly $15 billion in capital, nearly all of it directed toward purchasing Bitcoin. Saylor disclosed the role of artificial intelligence in creating these hybrid securities during an appearance on The Diary of a CEO podcast, describing how the company turned to ChatGPT after hitting practical ceilings with traditional financing methods.
From convertible bonds to AI-engineered securities
Strategy had been funding its Bitcoin acquisitions primarily through convertible bonds for years. The company eventually ran into the natural limits of how much capital it could raise through conventional convertible debt, a wall that forced Saylor’s team to get creative.
Rather than hiring another investment bank to brainstorm, Saylor turned to ChatGPT. The AI helped design a new class of preferred stock instruments that blend characteristics of both debt and equity, a hybrid structure that hadn’t previously existed in quite that form.
