Michael J. Saylor

Saylor was born in Lincoln, Nebraska, on February 4, 1965, and spent his early years on various Air Force bases around the world, as his father was an Air Force chief master sergeant. When Saylor was 11, the family settled in Fairborn, Ohio, near the Wright-Patterson Air Force Base.

In 1983, Saylor enrolled at the Massachusetts Institute of Technology (MIT) on an Air Force Reserve Officers' Training Corps (ROTC) full scholarship. He joined the Theta Delta Chi fraternity, through which he met his future co-founder of MicroStrategy, Sanju Bansal. Saylor double majored in aeronautical & astronautical engineering and history of science.

A medical condition prevented him from becoming a pilot, and instead, he got a job with a consulting firm, The Federal Group, Inc. in 1987, where he focused on computer simulation modeling for a software integration company. In 1988, Saylor became an internal consultant at DuPont, where he developed computer models to help the company anticipate change in its key markets. The simulations predicted that there would be a recession in many of DuPont's major markets in 1990.

As of 2016, Saylor had been granted 31 patents and had nine additional applications under review.

COVID-19 response criticism

In a 3,000-word memo to all MicroStrategy employees on March 16, 2020, entitled "My Thoughts on COVID-19," Saylor criticized countermeasures then being recommended against the disease, saying that it is "soul-stealing and debillitating [sic] to embrace the notion of social distancing & economic hibernation" and predicting that in the worst-case scenario, global life expectancy would only "click down by a few weeks." Saylor also refused to close MicroStrategy's offices unless he was legally required to do so. The full content of the memo appeared on Reddit for only a few minutes and was reposted in the Washington Business Journal.

SEC investigation

In March 2000, the U.S. Securities and Exchange Commission (SEC) brought charges against Saylor and two other MicroStrategy executives for the company's inaccurate reporting of financial results for the preceding two years. In December 2000, Saylor settled with the SEC without admitting wrongdoing by paying $350,000 in penalties and a personal disgorgement of $8.3 million. As a result of the restatement of results, the company's stock declined in value and Saylor's net worth fell by $6 billion.

District of Columbia tax fraud lawsuit

On August 31, 2022, the Attorney General for the District of Columbia sued Saylor for tax fraud, accusing him of illegally avoiding more than $25 million in D.C. taxes by pretending to be a resident of other jurisdictions during the years 2005 to 2021. He initially claimed he resided in Virginia during the period, then later claimed that he resided in Florida. MicroStrategy was accused of collaborating with Saylor to facilitate his tax evasion by misreporting his residential address to local and federal tax authorities and failing to withhold D.C. taxes. Saylor issued a statement saying: "I respectfully disagree with the position of the District of Columbia and look forward to a fair resolution in the courts." In June 2024, Saylor settled the tax dispute by agreeing to pay a $40 million fine.