How Michael Saylor rebooted his career and his company by becoming the world’s biggest bitcoin bull

Michael Saylor is no stranger to the limelight. The MicroStrategy CEO is perhaps best known for losing $6 billion in a single day during the height of the dot-com bubble, when the software business he had founded at age 24 nearly collapsed.

Two decades later, Saylor is once again at the center of a jittering conversation, thanks to his unprecedented embrace of bitcoin. With a mix of debt and virtually all of MicroStrategy’s cash, Saylor has bought more than 100,000 bitcoins that today are worth billions — and he doesn’t show any signs of slowing his buying binge anytime soon.

While other high-profile tech execs have invested company cash into crypto — Tesla’s Elon Musk and Square’s Jack Dorsey are among the best known — none has lashed their business’s fortunes to bitcoin the way that Saylor has. As little as 20% of Microstrategy’s value is tied to the company’s core software product, reckons analyst Kamil Mielczarek.

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