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One Tuesday in August last year, Michael Saylor’s life took a sharp turn.

The 56-year-old CEO of a sleepy enterprise-software company in Virginia suddenly became a business rock star. Saylor began appearing on television news shows, his name mentioned alongside tech visionaries such as Elon Musk and Jack Dorsey, while his company’s long-dormant stock soared.

The fundamentals of MicroStrategy, the business Saylor founded in 1989, were much the same as they’d been for years, except for one thing: On August 11, 2020, Saylor converted virtually all of the company’s cash into bitcoin.

In the months since, Saylor has doubled and tripled down on his bitcoin bet, borrowing more than $2 billion in debt to buy up more of the volatile cryptocurrency.

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