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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