Michael Saylor Used ChatGPT to Engineer $15 Billion Bitcoin Stock Offering

Strategy Inc. Executive Chairman Michael Saylor revealed that his company deployed OpenAI’s ChatGPT to engineer a novel Bitcoin-backed preferred stock structure that ultimately raised $15 billion, overcoming initial pushback from investment bankers and legal advisers.

Speaking on a Diary of a CEO podcast episode published Thursday, the 61-year-old software executive said he turned to generative artificial intelligence after conventional capital raising reached its limits. The financial structure allowed Strategy, formerly MicroStrategy, to continue aggressively purchasing digital assets, though the heavily leveraged strategy faces mounting scrutiny as Bitcoin drops 26 percent this year and Strategy shares decline 38 percent.

“You don’t want to learn how to do things the AI can do. What you want to do is learn how to ask the AI to do something that’s never been done before,” Saylor said during the interview with Steven Bartlett. “…If you want to create these incredible success things, you want to locate the magic opportunity.”

Addressing how professionals should position themselves alongside automated systems, Saylor urged workers to focus on novel problem-solving rather than competing on sheer labor output.

“If you’re in your working years where you want to upgrade the world and make a difference and be remembered for something—then a pretty simple principle is don’t keep doing the same thing over and over, working harder and harder every year, fighting against the modern automation, epidemic,” Saylor said. “Don’t try to outwork the robots.”

Founded in 1989, Strategy became the first publicly traded company to adopt Bitcoin as its core treasury reserve asset. The firm’s unprecedented exposure to digital currency has drawn criticism from Wall Street analysts, with Fortune’s Shawn Tully describing the capital structure as “dangerously” leveraged to fluctuating token prices.

Saylor, whose personal net worth is $3.3 billion according to Forbes, defended the firm’s appetite for financial risk despite market headwinds.

“We found some extraordinary cool thing. We committed to it with all of our heart and soul and we declared we were going to make it work come hell or high water,” Saylor said. “We got punched in the face a hundred times. And every single time we ran into a problem, we stopped, we recalibrated, we went a different direction.”

The high-stakes financial engineering echoes earlier periods in Saylor’s executive career. Following the dot-com market crash, MicroStrategy was forced to restate its financial statements after disclosing that 1999 revenue had been overstated by 25 percent. The adjustment reduced Saylor’s paper wealth by $6 billion in a single day—a record loss at the time—and prompted an investigation by the Securities and Exchange Commission. Saylor settled the SEC charges later that year by paying $8 million without admitting or denying wrongdoing.

Saylor’s view on generative automation reflects a broader consensus among technology leaders regarding workplace transformation. Microsoft Corp. Chief Executive Officer Satya Nadella highlighted the need for strategic adaptation during the 2023 World Economic Forum in Davos, Switzerland.

“I see these technologies acting as a co-pilot, helping people do more with less,” Nadella said. “The future of work is not just about technology and tools. It’s about new management practices and sensibilities to the workplace.”

Billionaire entrepreneur Mark Cuban expressed a similar perspective on the High Performance podcast, arguing that artificial intelligence will create unprecedented scale for innovative builders.

“There’s always something bigger and better that’s created by an innovative entrepreneur,” Cuban said. “But AI just dwarfs all that.”