Early Life and Education
Michael J. Saylor was born on February 4, 1965, in Lincoln, Nebraska. Due to his father's career as an Air Force chief master sergeant, Saylor spent his childhood on various U.S. Air Force bases. He excelled academically, graduating as valedictorian from high school. In 1983, he enrolled at the Massachusetts Institute of Technology (MIT) on an Air Force ROTC scholarship, earning dual degrees in Aeronautics & Astronautics and Science, Technology, and Society, graduating with honors in 1987.
Career and Rise to Success
After graduating from MIT, Saylor worked as a consultant. In 1989, at the age of 24, he co-founded MicroStrategy with Sanju Bansal. The company initially focused on data mining software. Under his leadership, MicroStrategy became a global leader in enterprise analytics and mobility software, serving thousands of organizations worldwide. MicroStrategy went public in 1998. However, the company faced challenges, including an SEC investigation in 2000. Saylor stepped down as CEO in 2022 and became Executive Chairman.
Key Business Strategies
Saylor is known for his strategic shift towards Bitcoin. In 2020, he led MicroStrategy to invest heavily in Bitcoin, making it one of the largest corporate holders of the cryptocurrency. As of March 2026, Strategy (formerly MicroStrategy) holds 762,099 Bitcoins. This strategy has significantly influenced the company's stock performance. MicroStrategy rebranded to Strategy in February 2025.
Philanthropy
Saylor established the Saylor Academy, a non-profit that offers free online education.