NewsCryptoMichael Saylor Credits ChatGPT for $15 Billion Strategy Raise, Tells Builders: 'Don't Try to Outwork the Robots'

Michael Saylor Credits ChatGPT for $15 Billion Strategy Raise, Tells Builders: 'Don't Try to Outwork the Robots'

Author: Fortune Crypto·

Key Takeaways

  • Michael Saylor used ChatGPT to help design a Bitcoin-linked preferred stock that enabled his company Strategy to raise approximately $15 billion through an IPO and related offerings.
  • Strategy became the first publicly traded company to adopt Bitcoin as a core treasury component in August 2020 and now holds the largest corporate Bitcoin treasury of any public firm.
  • Saylor advises professionals to focus on asking AI to accomplish unprecedented tasks rather than competing with automation or simply automating existing work.
  • Strategy's stock has declined 38% this year compared to Bitcoin's 26% drop, illustrating how the company trades as a leveraged proxy for the cryptocurrency.
  • Saylor previously faced an accounting scandal after the dot-com boom when MicroStrategy overstated 1999 revenue by 25%, erasing $6 billion from his net worth in a single day and leading to an $8 million SEC settlement.
Michael Saylor Credits ChatGPT for $15 Billion Strategy Raise, Tells Builders: 'Don't Try to Outwork the Robots'

Billionaire Michael Saylor says the key to building wealth in the age of artificial intelligence is not competing with machines but harnessing them. In a Diary of a CEO interview published on Thursday, Saylor revealed that he used ChatGPT to help his company, Strategy (formerly MicroStrategy), raise approximately $15 billion last year through a novel Bitcoin-based preferred stock.

"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 told podcaster Steven Bartlett. "Don't try to outwork the robots."

The 61-year-old offered that principle after Bartlett asked what it takes to build a legacy on the scale of figures like Michael Jackson or Elon Musk—someone globally recognized for their impact.

From Software Firm to Bitcoin Pioneer

Saylor founded MicroStrategy in 1989 as a business-intelligence software company. Over the past five years, however, he redirected the firm's strategy toward Bitcoin, making Strategy the first publicly traded company to adopt the cryptocurrency as a core component of its treasury—a move that began in August 2020 and has since been imitated by a small but growing cohort of corporations adding Bitcoin to their balance sheets. When more conventional financing methods were exhausted, Saylor said he turned to ChatGPT to help design a Bitcoin-linked preferred stock—a product that lawyers and bankers initially questioned because nothing like it had existed before.

Strategy ultimately raised roughly $15 billion through an IPO and related offerings, prompting Saylor to say that AI "made" him $15 billion. The company now holds the largest corporate Bitcoin treasury of any publicly traded firm.

For entrepreneurs and workers seeking to capitalize on the AI boom, Saylor described adopting the technology as a "no brainer." The real advantage, he argued, lies in asking better questions rather than simply automating existing tasks.

"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," he said. "…If you want to create these incredible success things, you want to locate the magic opportunity."

The Risks of Going All In on Bitcoin

Saylor's net worth currently stands at $3.3 billion, according to Forbes. However, his AI-fueled, Bitcoin-centric strategy carries substantial risk. Strategy's heavy reliance on the cryptocurrency—and its use of preferred stock to raise additional capital—has left the company deeply exposed to Bitcoin's price movements. Fortune's Shawn Tully has described the structure as "dangerously" leveraged.

That exposure has been evident this year: Bitcoin is down 26%, while Strategy shares have fallen 38%. The disparity illustrates a pattern financial analysts have flagged: because Strategy's stock increasingly trades as a leveraged proxy for Bitcoin, its declines tend to amplify the cryptocurrency's drops. Saylor, however, argued that major breakthroughs often demand weathering setbacks, and that the company's willingness to adapt through adversity has been central to its success.

"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."

It would not be the first time Saylor's aggressive bets produced severe consequences. After MicroStrategy's stock surged during the dot-com boom and made him a billionaire, the company was forced to restate its financial results, disclosing that 1999 revenue had been overstated by 25%. The accounting scandal erased $6 billion from his net worth in a single day—at the time, the largest one-day personal loss ever recorded. The SEC later accused him of violating federal securities laws; he settled the charges by paying $8 million without admitting wrongdoing.

Fortune reached out to Strategy for further comment.

Other Business Leaders Echo the AI-Embrace Message

Saylor is far from alone in urging professionals to treat AI as a tool for innovation rather than a threat to employment. Other prominent executives have argued that the most significant opportunities in the AI era will flow to those who combine the technology with distinctly human skills.

Microsoft CEO Satya Nadella has said that while AI will boost productivity, the future of work demands more than mere adoption. "I see these technologies acting as a co-pilot, helping people do more with less," Nadella said at the World Economic Forum's annual meeting in Davos, Switzerland, in 2023. "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 has gone further, predicting that entrepreneurs who harness AI to solve problems stand to generate unprecedented wealth. "There's always something bigger and better that's created by an innovative entrepreneur," Cuban said on the High Performance podcast last year. "But AI just dwarfs all that."

This story was originally featured on Fortune.com.