Crypto billionaire Michael Saylor says he made $15 billion last year with ChatGPT—and has one rule: 'Don't try to outwork the robots'

Michael Saylor has a new favorite collaborator, and it isn't a banker or a lawyer. It's ChatGPT. The Strategy co-founder told podcaster Steven Bartlett this week that the chatbot helped him design a Bitcoin-backed preferred stock structure so unusual that his own legal and financial teams balked at it. Nobody had built anything quite like it before. Strategy ended up raising roughly $15 billion through that IPO and related offerings, and Saylor is happy to credit the AI for the number.

His pitch to workers and founders is blunt: quit trying to out-hustle the machines. Saylor, 61, told Bartlett that grinding harder at tasks a robot can already do is a losing game. The move, he argues, is to use AI to chase problems that have never been solved, not to automate the ones you already know how to solve. He called it finding the "magic opportunity," which sounds a little mystical for a guy running a public company, but the underlying logic tracks with what other tech executives have been saying for a couple years now — Satya Nadella's co-pilot framing, Mark Cuban's claim that AI-savvy entrepreneurs will dwarf every wealth-creation wave that came before it.

Worth remembering: Strategy, the company once called MicroStrategy, didn't get here by playing it safe. Saylor pivoted the 1989-founded software firm into essentially a leveraged Bitcoin vehicle over the past five years, becoming the first public company to stack the cryptocurrency onto its balance sheet as core strategy. Fortune's Shawn Tully has flagged the approach as dangerously exposed to Bitcoin's swings, and 2025 has made that visible — Bitcoin is down 26% this year, Strategy's stock has dropped 38%. Saylor's own net worth, per Forbes, sits at $3.3 billion now, a fraction of what it once was.

And this isn't his first brush with a spectacular reversal. Back during the dot-com crash, MicroStrategy had to restate 1999 revenue after admitting it overstated results by 25%, wiping $6 billion off Saylor's net worth in a single day — at the time, the biggest one-day personal loss on record. The SEC came after him for securities violations; he settled for $8 million without admitting fault. So when Saylor talks about getting "punched in the face a hundred times" and recalibrating instead of quitting, he's speaking from a track record that includes some genuinely brutal punches.

The AI angle is new, but the pattern underneath it isn't. Saylor keeps betting everything on one big idea, weathering the fallout, and reframing the survival as proof of vision. This time the idea just happens to involve a chatbot helping structure a bond nobody had priced before.