The Unstoppable Michael Saylor and the Rise of Bitcoin

MicroStrategy shares are up about 690% in the past year and the 59-year-old executive chairman's approximately 10% stake is worth about $9.7 billion, while he personally owns an additional $1.9 billion or so of bitcoin.

MicroStrategy Inc. (MSTR) shares are up about 690% in the past year and the 59-year-old executive chairman’s approximately 10% stake is now worth about $9.7 billion, while he personally owns an additional $1.9 billion or so of bitcoin.

Saylor has emerged as the public face of the recent bitcoin craze, with nearly 4 million followers on X. To celebrate bitcoin topping $100,000, Saylor hosted a New Year’s Eve party for several hundred members of the crypto community at his waterfront, Miami-area estate, near his luxury yacht. A half-dozen dancers dressed in gold performed. Celebrities mingled with investing luminaries, including Bill Miller, the former Legg Mason fund manager; Peter Briger, chairman of Fortress Investment Group; and Mark Casey, a key portfolio manager at Capital Group. The event was livestreamed on YouTube to tens of thousands of bitcoin fanatics as Saylor, in a black blazer and a bitcoin T-shirt, presided.

Enthusiasm for Saylor’s company is so rabid it has resulted in a head-scratching situation: MicroStrategy owns about $47 billion of bitcoin, but its shares are worth about $97 billion. It’s as if investors are paying $2 for a $1 bill. Just as surprising: Sophisticated investors have been among the biggest buyers, including mutual-fund power Capital Group, which owned about 8% of the company as of Sept. 30, and Norges Bank Investment Management, Norway’s $1.5 trillion sovereign fund, which owned nearly 1%.

Fans say the premium reflects confidence that Saylor can continue to produce profits betting on bitcoin. Only 21 million coins will be created, a scarcity that boosts its value, they argue. By issuing equity at lofty levels, and selling debt at friendly terms to the company, Saylor can create value for shareholders as he expands MicroStrategy’s bitcoin horde, says Richard Byworth, a partner at SYZ Capital, who personally owns MicroStrategy stock.

“The premium is justified and will always be there," says Jordi Visser, a Wall Street veteran who worked at Morgan Stanley and recently purchased MicroStrategy shares. “No company can do what he’s done. They own about 2% of bitcoin—who can own more of it?"

There’s serious risk attached to Saylor’s strategy. He rode past investment waves until they crested and then crashed, losing billions of dollars of personal wealth, sometimes in a single day.

Saylor declined to comment for this article.

Saylor, a lifelong bachelor who turns 60 next month, has endured a series of career setbacks and run-ins with financial authorities and others. Last year, he agreed to pay Washington, D.C., $40 million to settle an income tax dispute, after Washington officials alleged that he previously lived in the District, not in Florida or Virginia as he claimed, and should have paid D.C. taxes.

The son of a career Air Force officer, Saylor studied aeronautics and science at Massachusetts Institute of Technology and was part of the Air Force Reserve Officer Training Corps. A few years after graduation, he launched MicroStrategy in