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Michael Saylor is the co-founder, former CEO, and current chairman of Strategy (formerly MicroStrategy), a business analytics company that emerged during the Dot-com boom. The U.S. business mogul is an influential advocate for Bitcoin and has directed Strategy to become one of the biggest corporate Bitcoin investors – a tactic that has proved lucrative.
Arguably, Saylor catalyzed a boom in corporate Bitcoin investment. He is also thought to be one of the five biggest individual Bitcoin investors in the world. Saylor has long been an outspoken advocate for the cryptocurrency, regularly appearing at industry events and engaging with politicians and policy-makers.
The former rocket scientist life hasn’t been without controversy, however, and he has made the news on two separate occasions for accusations of fraud and tax evasion resulting in multimillion dollar settlements.
Breaking Down Michael Saylor’s Net Worth in 2025
Michael Saylor has an estimated net worth of $8.3 billion in 2025, making him the 361st wealthiest person in the world today. His wealth comes from two main sources: the business he founded (MicroStrategy) and Bitcoin investments.
| Asset or Income Source | Amount |
|---|---|
| Strategy shares | $2.3 billion |
| Bitcoin holdings | $1.4 billion |
| Recent stock sales | $370 million |
| Tax fraud settlement | -$40 million |
| Total Net Worth | $4.03 billion |
The rising price of Bitcoin has since restored Saylor’s multibillionaire status. He holds more than 17 thousand Bitcoin, which is worth roughly $1.4 billion at the time of writing.
Saylor holds $2.3 billion worth of Strategy shares, making him the company’s largest shareholder. In 2023, the share price soared by 346%, and by June 2024, shares had already increased by more than 100% that year. Saylor also made $370 million in stock sales in the first part of 2024.
Early Life
Saylor was born in Lincoln, Nebraska in 1965. His father was in the Air Force and, as a child, Saylor lived on U.S. Air Force bases all over the world. He spoke about his upbringing and and the early days of MicroStrategy in a talk from years ago if you’re interested in learning more.
When he was a teenager, his family settled at an Air Force base in Dayton, Ohio. After graduating high school at the top of his class, he received an Air Force scholarship to study aeronautics and astronautics at the Massachusetts Institute of Technology (MIT). Saylor had hopes of becoming an Air Force fighter pilot, and while at university, he completed flight officer training at Lackland Air Force Base in Texas.
After graduation, Saylor joined the Air Force reserve and took on work as a consultant. His specialty was using computer simulations to aid business strategy. His clients included industry giants like DuPont and Exxon.
Founding Strategy (Formerly MicroStrategy)
In 1989, when he was 24, Saylor launched MicroStrategy with his roommate, Sanju Bansal. Their target was enterprise businesses, and according to one article, they provided “software that allowed companies to extract useful bits of information from their unwieldy corporate databases”. For example, a company might be able to predict which retail branch would sell the most units on a holiday.
The Boom Years
MicroStrategy’s software quickly attracted a list of Fortune 500 customers, and its revenue doubled every year from 1994 to 1997. By 1998, the company was listed on the NASDAQ (at a starting price of $6 per share) and was poised to benefit from the peak of the Dot-com boom. After just a few months as a public firm, MicroStrategy’s stock was worth more than Saylor’s former employer, DuPont.
In January, Saylor and MicroStrategy were flying high. The company announced that revenue for 1999 hit $205 million, an increase of 93% compared to 1998. MicroStrategy shares were worth $142 at the time. Saylor announced plans to raise $2 billion by issuing new stock. By March, the share price hit a peak of $333 (80 times the original share price).
He recalled, “I’m at the top of the world, everybody loves me. Everybody loves the company, we’re hitting the cover of every magazine.” MicroStrategy even hosted the Super Bowl party.
The $6 Billion Bust
The crash came even faster than the explosive rise in share price. In 2000, auditors informed the company that they were concerned that their numbers for 1999 were inaccurately reported as a result of some “creative accounting.” The company was forced to announce that its revenue for 1999 was in fact 25% lower than the year prior, marking a staggering decline. It had, in fact, lost money in each period.
As a result of the new report, the firm’s stock dropped by 62% and Saylor personally lost a record-breaking $6 billion in a day. The share price fell to $86.75 and the planned stock offering was cancelled.
The Securities and Exchange Commission (SEC) accused Saylor and two colleagues of committing fraud. Civil charges were filed in federal court in Washington. Saylor agreed to pay a $350 thousand penalty to the SEC and $8.3 million to shareholders. He also agreed to make various changes to the way that MicroStrategy was run.
One analyst suggested that the MicroStrategy bust was a major contributor to the bursting of the Dot-com bubble. At the very least, it was a key event marking the sector’s downturn. For the next two decades, MicroStrategy remained relatively low profile.
The Bitcoin Splurge
In 2020, while Saylor was CEO, the company bought Bitcoin for the first time. The move was heavily criticized by analysts and shareholders, but it turned out to be a fantastic bet. They purchased 21,454 tokens at roughly $12 thousand per token – a total of $250 million. The company continues to invest in crypto and now owns about 1% of all Bitcoin tokens in circulation – approximately 214 thousand tokens worth around $13.7 billion.
Saylor explained his decision to go all-in on Bitcoin with Strategy in an episode of The Pomp Podcast.
The company is believed to be the largest corporate Bitcoin investor in the world. In July 2024, it held 12 times more Bitcoin than the next biggest corporate investor. In fact, MicroStrategy stock is considered a proxy for the Bitcoin market.
Recent Years
In 2022, Saylor stepped down as CEO of the company but remained as Executive Chairman. In a press release, he said, “I will be able to focus more on the Bitcoin acquisition strategy….while [the new CEO] will be empowered…to manage overall corporate operations.” In 2025, MicroStrategy rebranded as Strategy.
MicroStrategy is now Strategy. https://t.co/p6UvQgOvnz
— Michael Saylor⚡️ (@saylor) February 5, 2025
Michael Saylor’s Income Tax Scandal
In 2021 and 2022, the District of Columbia filed lawsuits accusing Michael Saylor of evading more than $25 million in income taxes. The billionaire had been living in Washington from 2005 to 2020 but had not paid any income tax to the district during that period. DC said that he had fraudulently claimed that he lived in Virginia or Florida, where income taxes are lower.
Saylor denied wrongdoing and claims that he has lived in Miami, Florida, since 2012. Nonetheless, he settled for $40 million in 2024. According to Attorney General Brian L. Schwalb, “Saylor openly bragged about his tax-evasion scheme, encouraging his friends to follow his example and contending that anyone who paid taxes to the district was stupid.”
Saylor Foundation and Academy
Michael Saylor founded the Saylor Academy in 2008. Headquartered in Washington DC, the Academy is a non-profit that offers free online courses, including college credit and professional development courses. Topic areas include business administration. Computer science, and English as a Second Language. Saylor is the executive chairman of the organization.
Michael Saylor’s Books
Saylor is the author of “The Mobile Wave: How Mobile Intelligence Will Change Everything” (2012). The book is described as “a ground-breaking analysis of the impact of mobile intelligence, the fifth wave of computer technology.” It was number seven on the New York Times best-seller list for hardcover nonfiction in August 2012.
He co-wrote the book “What Is Money?” with Robert Breedlove, et al., which is described as, “a philosophical odyssey exploring anthropology, energy, and technology spanning from The Stone Age to The Digital Age in an effort to help people truly grasp the historic significance of Bitcoin.”
Michael Saylor’s Crypto Advocacy
Saylor is an outspoken and influential advocate of Bitcoin. He frequently appears on the news, in podcasts, and at industry events to discuss the value of Bitcoin. In March 2025, he attended a crypto summit at the White House alongside crypto leaders like Coinbase co-founder Brian Armstrong and the Winklevoss twins. He used the opportunity to promote pro-crypto policies.
When you get invited to discuss Digital Assets at the White House, make sure you wear your Orange Tie. pic.twitter.com/1KvjsCdDmp
— Michael Saylor⚡️ (@saylor) March 8, 2025
He believes that Bitcoin is essential to the prosperity of the United States in the 21st century. He has also said that “Bitcoin is the best way to promote personal liberties and free markets”. He has also made positive comments about NFTs – although Bitcoin is his focus.
As CEO, he made Strategy the first U.S. public company to transfer its balance sheet from crash into crypto. He has led the company to become the biggest corporate Bitcoin investor in the world. Saylor also has significant Bitcoin holdings of his own and has achieved Bitcoin “whale” status.
Saylor is one of the more controversial advocates for cryptocurrencies on social media, often drawing ire for his bold comments. For example, he once suggested that listeners should sell everything they have and mortgage their house to buy Bitcoin.
Michael Saylor Crypto & NFT Holdings
Saylor’s known crypto holdings are worth roughly $1.4 billionin 2025. He stated in an interview that he has not invested in NFTs. Saylor also holds $2.3 billion worth of Strategy shares. The company owns around 1% of all Bitcoin tokens (roughly 214 thousand tokens worth around $13.7 billion) and continues to invest in Bitcoin. Therefore, Saylor indirectly owns an enormous amount of the token.
Michael Saylor’s Other Assets
According to Saylor, his house in Miami Beach “was appraised at $46 million a few years ago”. A 2021 court filing states that he owns a “multimillion waterfront penthouse” in Georgetown, Washington. He is thought to own another penthouse in the Adams Morgan area. He has also owned several yachts, including a 154-footer, which he bought in 2013 for $31.5 million. Saylor apparently has a full-time crew living on a yacht moored outside his Miami Beach home so he can travel at short notice.
Michael Saylor’s house in Miami Beach was worth $100,000 in 1930…..
It was appraised at $46 million a few years ago
pic.twitter.com/Wy8g2ztjKH— Business Blurb™ (@businessblurbb) April 20, 2024
Michael Saylor Net Worth: The Verdict
While fines and settlements relating to fraud and tax evasion have made a dent in Saylor’s net worth, he remains one of the wealthiest people in the world. His estimated net worth is over $8 billion. His wealth comes from the success of his business in the 1990s, his astute direction of Strategy’s enormous Bitcoin investments, and his own personal Bitcoin purchases.
However, Saylor’s two income sources are both entirely reliant on Bitcoin’s value. Fortunately for Saylor, he and other top crypto advocates have the ear of the White House, which has already signaled a much more friendly approach than the previous administration. If both Saylor and Strategy continue to make savvy crypto investing decisions, the entrepreneur will likely retain his multibillionaire status.
FAQs
What are Michael Saylor’s Bitcoin Holdings?
Michael Saylor bought 17,732 Bitcoins in October 2020. At the time of writing, his holdings are worth roughly $1.4 billion.
How did Michael Saylor get rich?
Michael Saylor founded a company called Strategy (formerly MicroStrategy) which made him a multibillionaire during the Dot-com boom. He remains the biggest shareholder of Strategy which continues to grow and generate wealth for the founder. Saylor has also made considerable investments in Bitcoin.
How old is Michael Saylor?
Michael Saylor is 60 years old.
