Shortly thereafter, he got a driver’s license and registered to vote in the Florida, and began filing his taxes in the Sunshine State, while spending most of his time in DC, commuting to MicroStrategy’s headquarters in Tyson Corner, Va and “indulg in the District’s social scene.” Adds the complaint, “He even suggested that his friends from New York, California, or the District, were ‘fools’ if they did not evade the personal income taxes imposed by their respective states by similarly acquiring a house in Florida and spending time there.”
The complaint recounts that in 2012, Saylor purchased a bayfront Mediterranean mansion in Miami Beach called Villa Vecchia for $13.1 million.
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The document is full of fun nuggets that illustrate Saylor’s attachment to the nation’s capital: How Saylor combined three luxury apartments on the Georgetown waterfront to create the 7,000 square foot penthouse he dubs Trigate, and where he really resided most of the time, the yacht and backup craft he docked in front of the abode, his regular appearances at a premier place to see and be seen, Cafe Milano, and his addiction to flying the world in MicroStrategy’s Bombardier Global Express private jet, for which the FAA maintains flight records that provide “an almost perfect representation of Saylor’s travel to and from the District” for the past two decades. It alleges that Saylor lived in DC most of the year from 2013 to 2020, but claimed residence in the no-income-tax state of Florida. In fact, the whistleblower’s account is astoundingly detailed. It’s clear that the whistleblower saw a great deal of Michael Saylor, and given the knowledge of the jockeying inside of MicroStrategy, might well have been a high-ranking executive. The suit was sealed and remained secret until the District issued a separate action, including virtually the same charges, on the last day of August. In August of 2021, the whistleblower filed the first case accusing Taylor of illegally skirting $25 million in payments. In 2021, the District updated the law allowing private citizens to bring suits, with DC as co-plaintiff, against “high-earning companies and individuals” for tax evasion. The District has long deployed a False Claims Act to pursue, for example, contractors who over-bill or fail to complete construction projects. The District case arises from an earlier complaint filed by a whistleblower. (For Fortune’s full look at Michael Saylor’s wild career and massive bet on Bitcoin, read the full story here.) And Saylor so intimidated the brass at the data analytics pioneer that they bowed to the boss, knowing full well he was blatantly skirting millions in taxes, and putting the enterprise he founded at risk. Most shocking, Saylor stands accused of recruiting his lieutenants at MicroStrategy to conspire in an intricate plan for orchestrating the fraud. According to the suits, Saylor mocked other well-to-do folks who paid taxes in the District as “fools,” and exhorted friends to follow his example.
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