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

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.