Born on February 4, 1965, he is the Executive Chairman and co-founder of MicroStrategy, a company that provides business intelligence, mobile software and cloud services. Saylor is famous for his statements that began in 2020 when he decided to buy Bitcoin with the cash of his company Microstrategy.
Saylor was born in Lincoln, Nebraska on February 4, 1965 and spent his early years at several US air force bases around the world as his father was a chief sergeant of the air force. In 1983, he entered the MIT (Massachusetts Institute of Technology). It was at this time that he met Sanju Bansal, the future co-founder of Microstrategy. He graduated from MIT in 1987 with a double major in aeronautics and astronautics, and science, technology and society.

He wants to become a pilot but it seems that a health problem prevents him from realizing his dream. Instead, he got a job at a consulting firm, The Federal Group, Inc. in 1987 where he worked on computer simulation modeling for a software integration company. The following year, he became an internal consultant at DuPont, where he developed IT models to help the company anticipate changes in its key markets.
With DuPont funds, Saylor founded MicroStrategy with Sanju Bansal, whom he met in his fraternity at MIT during these studies a few years ago. The company starts with developing data mining software. The company then focuses on business intelligence software. In 1992, the company began to win large contracts with reputable companies.
This is where Saylor’s success began. In 1996, he was named High-Tech Entrepreneur of the Year by KPMG Washington. In 1997, Ernst & Young named Saylor its Software Entrepreneur of the Year, and the following year, Red Herring magazine recognized him as one of their top 10 entrepreneurs for 1998. In the same year, in June, Saylor and Bansal listed Microstrategy, with an initial share offering of 4 million shares at $12 each. The following year, in 1999, Saylor was named “Innovator under 35” by MIT Technology Review.
While everything seems to be successful in Saylor, he will experience his first difficulties in 2000. In March, the US Securities and Exchange Commission (SEC) filed a complaint against Saylor and two other executives of MicroStrategy for publishing inaccurate financial results reports for the previous two years. He will be required to pay a personal restitution of $8.3 million. As a result of this scandal, the value of the company’s shares is falling and Saylor’s net worth falls by $6 billion. A bad year for Saylor, however it will be many years before they are again in the front of the stage.
At the MicroStrategy Quarterly Results Call (from to covid 19) in July 2020, Saylor announces its intention for MicroStrategy to explore purchasing Bitcoin, gold and other alternative assets instead of holding cash. The following month, MicroStrategy uses $250 million of its cash inventory to buy 21,454 bitcoins. Subsequently, Microstrategy never stopped buying Bitcoin. MicroStrategy now has an impressive total of 471 107 BTC.

The MicroStrategy boss has established himself as one of the world’s largest bitcoin holders. A bet that might seem like completely crazy, yet today this choice seems successful. Even if the tech stars on Wall Street are called Nvidia, the master of AI chips, Microsoft, Apple, Tesla or Netflix, it is his company Microstrategy that recorded a record increase of 600% during 2024. Its value is now around $80 billion. An ardent defender of Bitcoin, Saylor may have seemed crazy to the general public. Yet the explosion in value of Bitcoin has propelled it to the forefront. With the arrival of an administration extremely favorable to cryptocurrencies, Saylor appears today as a true visionary. These statements are now being scrutinized by the entire crypto community making him alongside Elon Musk, one of the most influential people in the ecosystem.