How Michael built the fortune
Michael Saylor's wealth has been made twice. The first time was in enterprise software. In 1989 he co-founded MicroStrategy with Sanju Bansal, a friend from MIT, to build tools that let companies analyse large volumes of business data. The firm sold reporting and analytics software to retailers, banks and government agencies, and it went public on the Nasdaq in 1998. During the dot com boom its shares soared, and Saylor briefly became one of the richest people in the technology industry.
That first fortune shrank sharply in March 2000, when MicroStrategy announced it would restate several years of revenue. The share price collapsed, and Saylor and other executives later settled accounting fraud charges with the Securities and Exchange Commission without admitting or denying wrongdoing. He remained in charge, and the company survived as a smaller, profitable software business for the next two decades.
The second fortune came from bitcoin. In August 2020 Saylor announced that MicroStrategy would use its spare cash to buy bitcoin as a treasury reserve asset, arguing that holding cash during a period of low interest rates and money printing would erode its value. The company then went much further, issuing convertible bonds, preferred shares and new common stock to raise billions of dollars specifically to buy more bitcoin. Saylor also disclosed large personal holdings of the cryptocurrency.
The strategy turned the company into a leveraged proxy for bitcoin. When the price of bitcoin rose, the company's shares tended to rise faster, and Saylor's large stake, including high-vote shares that give him control, rose with them. The approach has been copied by other listed companies, and it has also been criticized for exposing shareholders to the swings of a single volatile asset.
Companies and holdings
Saylor's main assets are:
- his shares in Strategy, the new name MicroStrategy adopted in 2025, where he is executive chairman and holds most of the voting power
- personal bitcoin holdings, which he has described publicly
- the Saylor Academy, a nonprofit online education project he funds
In 2022 he stepped down as chief executive, handing the role to Phong Le, and became executive chairman so he could focus on the company's bitcoin strategy. The firm continues to operate its analytics software business alongside its bitcoin holdings.
Strategy's capital raising has become a business in its own right. The company has sold several classes of preferred stock with different dividend and conversion terms, alongside at-the-market offerings of common shares, and has used the proceeds to keep adding to its bitcoin reserve. Saylor presents the firm as a vehicle that offers investors different levels of exposure to bitcoin, while critics point to the leverage and the dependence on continued demand for its securities.
Early life and career
Saylor was born in 1965 in Lincoln, Nebraska, and grew up mainly in Fairborn, Ohio, near Wright-Patterson Air Force Base, where his father served in the Air Force. He won an Air Force ROTC scholarship to the Massachusetts Institute of Technology, where he studied aeronautics and astronautics and the history of science, graduating in 1987.
A medical condition prevented him from serving as a pilot, so he turned to business. He worked in consulting, including on simulation models for the chemical company DuPont, which became MicroStrategy's first major customer and helped launch the company.
The idea behind MicroStrategy's software grew out of that consulting work. Saylor saw that large organizations collected huge amounts of data but lacked easy ways to query it, and he and Bansal built tools that let managers produce reports and analyses without writing code. The approach made the company one of the early leaders in what became known as business intelligence software.
Philanthropy and public life
Saylor's most visible charitable project is the Saylor Academy, founded through his foundation in 2008, which offers free online college-level courses. He has also donated to MIT and other institutions. In 2012 he published a book about the effect of mobile technology on business and society.
Since 2020 he has become one of the most prominent advocates for bitcoin, speaking at conferences and on social media and urging corporations and governments to hold it. In 2024 he and MicroStrategy agreed to pay 40 million dollars to settle a lawsuit by the District of Columbia alleging that he had avoided local income taxes; he did not admit wrongdoing. He lives in Miami Beach.