He is the executive chairman and co-founder of MicroStrategy, a company that provides business intelligence, mobile software, and cloud-based services.

[2][3] In 1983, Saylor enrolled at the Massachusetts Institute of Technology (MIT) on an Air Force Reserve Officers' Training Corps (ROTC) full scholarship.

[2][4] A medical condition prevented him from becoming a pilot,[2][3] 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.

[4] In 1988, Saylor became an internal consultant at DuPont, where he developed computer models to help the company anticipate change in its key markets.

[9] By early 2000, Saylor's net worth reached $7 billion, and the Washingtonian reported that he was the wealthiest man in the Washington D.C.

[16] MicroStrategy ultimately settled with the SEC, agreeing to hire an independent director to ensure ongoing regulatory compliance.

[17][18] After his leadership was criticized by several major investors in 2014, Saylor has since opted for a symbolic one-dollar salary without any cash bonuses, but with stock options.

[20] On August 8, 2022, Saylor assumed the title of executive chairman of MicroStrategy and appointed Phong Le, the company's president, to succeed him as CEO.

On December 11, 2020, MicroStrategy announced that it had sold $650 million in convertible senior notes, taking on debt to increase its Bitcoin holdings to over $1 billion worth.

[27] Despite criticism from skeptics like Peter Schiff, Saylor remains confident in Bitcoin as an inflation hedge and a transformative financial asset.

MicroStrategy has significantly increased its Bitcoin holdings, recently announcing a $700 million debt sale to further invest in the cryptocurrency.

[28] 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."

[10][11][12] 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.

[43] 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.