The Numbers Come First
Michael Saylor, the 61-year-old founder of Strategy — formerly MicroStrategy — says artificial intelligence was instrumental in raising approximately $15 billion for his company last year. Speaking on the Diary of a CEO podcast with host Steven Bartlett, Saylor said he turned to ChatGPT to help design a Bitcoin-based preferred stock after the company had exhausted more traditional capital-raising channels. Lawyers and bankers initially questioned the structure, according to Saylor, because no comparable product had existed before.
Strategy ultimately raised roughly $15 billion through an IPO and related offerings tied to that instrument. 'Don't keep doing the same thing over and over, working harder and harder every year, fighting against the modern automation epidemic,' Saylor told Bartlett when asked what it takes to build a legacy of lasting impact.
The Leverage Behind the Rally
The win is real — and so is the risk. Fortune's Shawn Tully has described Strategy's structure as 'dangerously' leveraged to Bitcoin's price. That exposure is visible in 2025 performance data cited in the source: Bitcoin is down 26% this year, while Strategy shares have fallen 38%. Saylor's current net worth stands at $3.3 billion, according to Forbes.
Saylor's record with bold bets is long. After MicroStrategy's stock surged during the dot-com boom, the company was forced to restate financial results after disclosing that 1999 revenue had been overstated by 25%. The SEC accused him of violating federal securities laws; he settled, paying $8 million to the agency without admitting wrongdoing. The accounting scandal cost him an estimated $6 billion in a single trading day — at the time the largest single-day personal loss on record.
Saylor frames the setbacks as part of the playbook. '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,' he said.
The Principle Behind the Pitch
For workers and entrepreneurs, Saylor's core argument is about the quality of prompts, not the volume of output. '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.
He is not alone in that framing. Microsoft CEO Satya Nadella said at the 2023 World Economic Forum in Davos that 'the future of work is not just about technology and tools. It's about new management practices and sensibilities to the workplace.' Entrepreneur Mark Cuban has gone further, saying on the High Performance podcast that 'AI just dwarfs all' previous waves of entrepreneurial opportunity.
CEO Times Read
Saylor's story is a clean illustration of what free enterprise rewards: the willingness to deploy capital in a direction the consensus hasn't priced yet, then absorb the volatility that comes with being early. The $15 billion raise didn't come from a government program or a regulatory carve-out — it came from a founder who asked a machine a question no lawyer had thought to ask first.
The risk is equally instructive. Leverage amplifies both directions, and Strategy's 38% share decline this year is a reminder that conviction without risk management is not a strategy — it is a wager. The market has already voted on that distinction. Capital rewards clear rules and honest accounting; it punishes neither boldness nor caution as such, only the confusion of one for the other.
