Michael Saylor Lost Big in the Dot-Com Bubble and Bitcoin’s Crash. Now He Aims to Rebound Again

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Michael Saylor Lost Big in the Dot-Com Bubble and Bitcoin's Crash. Now He Aims to Rebound Again

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Saylor and MicroStrategy then spent two decades mostly under Wall Street’s radar. Not that he was suffering. MicroStrategy kept plugging away, developing software for businesses. Saylor lived in a Miami Beach, Fla., mansion that looks like a Spanish colonial palace. A recent visit by a CoinDesk reporter revealed painted cherubs on the foyer ceiling, gold paneling and crimson-red wall paper in the dining room, a stage beyond the office library stocked with guitars, drums and whatever else a band might need, and a portrait of Saylor styled like an old English sailor – with laser eyes. A yacht was floating out back, where a crew lived full-time so Saylor could travel whenever he wanted.

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