Michael Saylor is the chairman and CEO of the business intelligence software company MicroStrategy, which famously used its retained earnings to buy bitcoin in the spring of 2020.
On August 2, 2022, Saylor announced he would step down as CEO and take a new post as executive chairman, focused on the company's bitcoin strategy.
On August 31, 2022, it was announced that Washington, D.C., had sued Saylor for tax fraud, claiming that he failed to pay more than $25 million in income taxes despite living in the district for more than a decade. The lawsuit, filed with the D.C. Superior Court’s civil division, alleged Saylor knowingly avoided paying taxes he owed since 2005 by fraudulently claiming to be a resident of other, lower-taxes jurisdictions, including Virginia and Florida.
Saylor was born in Lincoln, Nebraska, in 1965. He studied aeronautics in college on a Reserve Officer Training Corps scholarship and was commissioned by the U.S. Air Force as a second lieutenant.
He was sidelined from his goal of becoming an Air Force pilot by a heart murmur. After leaving college in 1987 Saylor joined a software integration start up in New York City which failed after about a year. He then worked as a computer consultant at DuPont Company in Wilmington, Delaware, where he built business forecasting computer models. While working for DuPont as a consultant, Saylor persuaded the company to sponsor his start up software company, MicroStrategy, which he founded with a former MIT classmate, Sanju Bansal.
The company Saylor founded grew rapidly. "Nobody has really grasped yet the great wealth that can be made selling data over the Web," Saylor told the Washington Post in 1996. "There are 100 million potential customers out there." 
In 2000, Saylor accepted a penalty of $350,000 personally and $8 million from the company to settle charges of a massive accounting fraud from the U.S. Securities and Exchange Commission. Saylor and two other executives were charged with committing civil fraud. The agency forced the company to restate its earnings for the previous three years during which the company had claimed consecutive profits. The restatement showed the company had much lower revenues than previously reported and in fact had experienced losses each year.
MicroStrategy’s price per share free fell $140 in a single day as it fell to $86.75 from the prior day’s close of $226.75 on March 20, 2000. As a large shareholder, Saylor's personal wealth suffered a $6 billion loss, the largest one day personal financial loss ever recorded up to that point.
After a long period of lackluster growth, MicroStrategy became the first publicly-listed company to allocate capital reserves to cryptocurrency when it purchased 21,454 bitcoin in August 2020. The initiative was directed by Saylor and it made him a bitcoin celebrity.
MicroStrategy announced on August 11, 2020 that it had invested approximately $250 million in bitcoin saying, “Our investment in bitcoin is part of our new capital allocation strategy, which seeks to maximize long-term value for our shareholders.” The company alluded to its upcoming purchase in its July 28 report on its second quarter 2020 financial results. It also said it would return approximately another $250 million to shareholders.
Saylor graduated from high school first in his class and served as both class marshal and valedictorian. He graduated from MIT in 1987 with highest honors with a major in aeronautics and astronautics.
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