MicroStrategy founder Michael Saylor once lost $6 billion in a day. His big bet on Bitcoin might sink him once and for all
, 2022-08-03 14:50:00,
It was the early hours before MicroStrategy’s IPO in 1998, but founder Michael Saylor wasn’t assuaging big investors or running through projections, or even putting champagne on ice.
Ensconced in a $10,000-a-night three-story rooftop suite at Manhattan’s Palace Hotel, he found his attention captured by something else entirely: the suite’s private elevator. He was so enthralled by the opulent toy that, according to a press account at the time, the young founder spent the early morning hours obsessively riding it up and down.
Indeed, when looking at Michael Saylor’s 33-year career, one gets the sense that the wild ups and downs don’t faze him at all. In fact, he may even be chasing them. At the NASDAQ later that morning, MicroStrategy’s stock popped 100% from the offering price to garner an almost $1 billion valuation. By the close, Saylor’s stake reached $540 million.
Years later, MicroStrategy would become ensnared in an accounting scandal that sent the stock plunging 62% in one day; Saylor lost $6 billion in personal wealth. His swift financial decline even turned him into an answer to the Trivial Pursuit question: “Who has lost the most money in a single day?”
Still, the entrepreneur persisted. He went on to offer a promising new product to Facebook, sell a cloud-based software platform he’d built in-house for over $100 million, pen a prophet bestseller on the mobile future, and collect multiple yachts, one of which starred in the wild party scene of an Entourage movie.
But Saylor’s most outrageous swing of all is one that’s playing out right now at MicroStrategy. Over the past two years he has essentially bet his entire $500 million revenue company on the future of Bitcoin. On August 2, the company announced Saylor would step down as CEO after three decades at the helm to take the role of executive chairman. In a statement, Saylor attested that the new job will enable him to focus “on our Bitcoin acquisition strategy and related Bitcoin advocacy initiatives.” (Given that Saylor controls the voting stock, and will stay on executive chairman, it’s certain the decision was his, though the company did not respond to several requests for interviews with Saylor.) In a surreal twist, though the company announced a gigantic writedown of $918 million on its Bitcoin holdings, MicroStrategy’s stock soared the day after the news hit, rising 15% to $321 and gaining over $400 million in market cap.
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