Michael J. Saylor

Michael Saylor
Michael Saylor speaking in an interview Saylor in 2022
Born	Michael J. Saylor 4 February 1965 (age 61) Lincoln, Nebraska, U.S.
Education	Massachusetts Institute of Technology (BS)
Occupations	Entrepreneur Business executive
Years active	1987–present
Notable work	The Mobile Wave
Title	Executive chairman of MicroStrategy

Michael Saylor (born February 4, 1965) is an American entrepreneur and co-founder and CEO of MicroStrategy. He studied aeronautics and astronautics at MIT and later developed interests in computing and decision support systems. He serves as executive chairman and co-founder of MicroStrategy, a company specializing in business intelligence, mobile software, and cloud-based services.

Saylor was MicroStrategy's chief executive officer from 1989 to 2022. In 2000, Saylor and two other MicroStrategy executives were charged by the U.S. Securities and Exchange Commission with fraudulently reporting the company’s financial results. Saylor settled without admitting wrongdoing, paying $350,000 in penalties and $8.3 million in personal disgorgement. [1]

Michael Saylor’s company, MicroStrategy (now Strategy), pioneered corporate Bitcoin adoption by purchasing its first Bitcoin in August 2020. The firm steadily accumulated Bitcoin through equity and debt financing, influencing other corporations to treat Bitcoin as a treasury reserve asset and helping normalize institutional participation in cryptocurrency markets.

Under Saylor, MicroStrategy has spent billions of dollars to purchase over 600,000 bitcoins In 2024, Saylor and MicroStrategy agreed to pay $40 million to settle a Washington, D.C., tax fraud lawsuit alleging improper residency claims. Saylor denied wrongdoing and disputed residency allegations to avoid litigation. In 2012, Saylor published “The Mobile Wave: How Mobile Intelligence Will Change Everything”, a nonfiction book analyzing mobile computing as a major technological shift and its impact on society and future digital platforms.

Early Life and Education

Michael J. Saylor was born on 4th February 1965, in Lincoln, Nebraska, he is the son of a U.S. Air Force noncommissioned officer. He spent his childhood relocating across the United States, Japan, and New Zealand. When Saylor was 11, his family settled in Fairborn, Ohio, near Wright-Patterson Air Force Base.

In 1983, Saylor entered the Massachusetts Institute of Technology on a full Air Force ROTC scholarship, earning dual degrees in Aeronautics and Astronautics and in Science, Technology, and Society. While studying at MIT, Saylor joined the Theta Delta Chi fraternity, where he met Sanju Bansal, who later became a key business associate in his career. Bansal was born in India and raised in Washington, D.C., and studied engineering at the Massachusetts Institute of Technology.

After graduating from MIT, Saylor worked at The Federal Group and later became an internal consultant at DuPont in 1988, where he developed computer models to forecast market changes. One model correctly predicted a 1990 recession. In 1989, DuPont supported his work with a $250,000 consulting contract and office space. As of 2016, Saylor had been granted 31 patents, with nine additional patent applications under review.

MicroStrategy

Saylor co-founded MicroStrategy in 1989 with Sanju Bansal, his MIT roommate and fraternity associate. After developing computer models for DuPont’s titanium dioxide business, he secured a $250,000 consulting contract and office space near DuPont’s Wilmington, Delaware, headquarters to launch the company. The company initially focused on business intelligence software to simplify data analysis.

An early milestone was a $10 million contract with McDonald’s in 1992 to analyze promotional effectiveness. The McDonald’s contract led Saylor to recognize the potential for developing business intelligence software that enabled organizations to derive actionable insights from their operational data.

In 1995, MicroStrategy ranked as the ninth-largest developer of decision support system (DSS) software in the United States. In 1996, Saylor was named KPMG Washington High - Tech Entrepreneur of the Year. The company later relocated to Vienna, Virginia, and became a public company in June 1998.

Saylor has received multiple honors, including KPMG Washington High-Tech Entrepreneur of the Year (1996) and Ernst & Young Software Entrepreneur of the Year (1997). Red Herring named him among its Top 10 Entrepreneurs in 1998, and MIT Technology Review listed him as an “Innovator Under 35” in 1999.

MicroStrategy’s initial public offering on June 12, 1998, was priced at $6 per share (adjusted for a January 2000 two-for-one stock split). The stock rose on its first trading day and increased significantly through 1999, eventually reaching $333 per share on March 10, 2000. In March 2000, MicroStrategy announced that it would restate two years of previously reported financial results, leading to a sharp decline in its stock price. In April 2000, the company formally restated its 1998 and 1999 revenues and earnings in filings with the U.S. Securities and Exchange Commission. MicroStrategy’s stock price, which had risen from approximately $7 to as high as $333 per share within a year, declined sharply by about 62% in a single day, falling to around $120 per share. The drop is widely cited as a notable event associated with the bursting of thedot-com bubble.

By August 2000, approximately two dozen class action securities fraud lawsuits had been filed against the company in the United States District Court for the Eastern District of Virginia. In December 2000, the U.S. Securities and Exchange Commission filed fraud charges against MicroStrategy and its executives. The company later settled with the SEC and agreed to appoint an independent director to overseeregulatory compliance.

Following criticism from several major investors in 2014, Saylor adopted a symbolic salary of one dollar without cash bonuses, while continuing to receive stock options. According to Bloomberg, Saylor exercised stock options valued at approximately $400 million during the first quarter of 2024.

As of August 8, 2022, Saylor assumed the role of Executive Chairman, while Phong Le became President and Chief Executive Officer and joined the board of directors. Saylor remained chairman of the board and an executive officer of the company. As of November 2024, Saylor held approximately 9.9% of MicroStrategy shares, representing about 45% of voting power. Institutional investors and the public also held significant ownership stakes. In February 2025, the company rebranded as Strategy, adopting a new logo with a stylized “B” and changing its primary color to orange.

Bitcoin Advocacy

Saylor is a prominent advocate of bitcoin and has stated that he believes it may displace gold as a non-governmental store of value. Saylor has described bitcoin’s primary utility as capital preservation and has compared purchasing it to buying property in a highly desirable city. He has also referred to bitcoin as “the apex property of the human race.”

During MicroStrategy’s July 2020 earnings call, Saylor announced plans to explore alternative assets in place of cash holdings. In August 2020, the company used $250 million to purchase 21,454 bitcoins. The purchase helped popularize the term “digital asset treasury” to describe public companies holding cryptocurrency as a treasury reserve asset.

In September 2020, MicroStrategy added $175 million in bitcoin, followed by $50 million in early December 2020. On December 11, 2020, it issued $650 million in convertible senior notes. On December 21, 2020, the company reported holdings of 70,470 bitcoins purchased for $1.125 billion at an average price of $15,964 per bitcoin. As of February 23, 2025, MicroStrategy and its subsidiaries held approximately 499,096 bitcoins, acquired for about $33.1 billion at an average price of $66,357 per bitcoin, according to company filings and regulatory disclosures.

Despite criticism, Saylor has maintained strong support for bitcoin and MicroStrategy’s continued accumulation strategy. He has stated his willingness to advise on cryptocurrency policy and indicated that he would consider serving on a potential crypto advisory council under the Trump administration.

Political Views

In March 2020, Saylor circulated a 3,000-word internal memorandum to MicroStrategy employees titled “My Thoughts on COVID-19,” in which he criticized recommended public health measures such as social distancing and economic shutdowns. He characterized these measures as harmful and initially declined to close company offices unless legally required, drawing public and media criticism.

The Mobile Wave

In 2012, Michael Saylor published The Mobile Wave: How Mobile Intelligence Will Change Everything, a nonfiction book analyzing mobile computing as a transformative technological wave and its impact on society and future digital platforms. Following its 2012 release, The Mobile Wave reached number seven on The New York Times hardcover nonfiction bestseller list and was promoted through Saylor’s keynote appearances at industry conferences.

Saylor Academy

Saylor Academy is a nonprofit organization founded in 2008 to provide free, open online education. It offers more than 150 self-paced college and professional-level courses, along with certificates and opportunities for tuition-free college credit. The initiative aims to expand global access to education and is operated by the Constitution Foundation, a U.S. 501(c)(3) nonprofit.

Awards and Recognition

Saylor has received numerous awards and forms of recognition during his career for his contributions to technology, entrepreneurship, and business leadership. In 1996, he was named KPMG High-Tech Entrepreneur of the Year. In 1997, he was named to Ernst & Young’s Entrepreneur of the Year list. In 1999, MIT Technology Review recognized him as an “Innovator Under 35”. Additionally, Saylor has been featured in various industry publications and rankings recognizing his influence in the technology sector and digital currency advocacy.

Controversies

SEC Investigation

In December 2000, the U.S. Securities and Exchange Commission filed and settled civil charges against Saylor, Sanjeev Bansal, and Mark Lynch, alleging improper revenue recognition by MicroStrategy from 1998 to 2000. The executives consented to injunctions, paid $10 million in disgorgement, and civil penalties.

The case followed financial restatements and a sharp stock price decline, and the SEC imposed additional compliance measures on the company.

District of Columbia Tax Fraud Lawsuit

In August 2022, the District of Columbia attorney general filed a tax fraud lawsuit against Saylor and MicroStrategy, alleging that Saylor evaded more than $25 million in District income taxes by falsely claiming residency in jurisdictions with lower tax rates. The suit also named MicroStrategy, alleging that it assisted in the scheme.

The lawsuit sought recovery of unpaid taxes and penalties under the District’s False Claims Act, following whistleblower complaints and an investigation by the Office of the Attorney General. In June 2024, Saylor and MicroStrategy agreed to pay $40 million to settle a tax fraud lawsuit alleging improper residency claims to avoid District income taxes. Saylor denied wrongdoing and said he settled to avoid continued litigation.