Michael Saylor, the billionaire software mogul and one of the biggest Bitcoin whales, first rose to fame back in the 90s, when his company, MicroStrategy, was at the peak of its success. Yet, there was a dark cloud on the horizon, as MicroStrategy stock lost 62% of its value in one day, erasing $6 billion from Saylor’s wealth and making headlines as one of the catalysts that finally caused the 2000s dotcom bubble to burst.
Although Saylor's net worth never truly recovered to the levels of MicroStrategy's most glorious days, he was lucky to bounce back, coming up with an even riskier bet: to take on debt to increase his company's Bitcoin holdings to over $1 billion. Since 2020, when he first announced MicroStrategy's corporate coffers would be used to purchase the "digital gold," the business intelligence firm's bitcoin holdings rose to an astounding 158,400 BTC (almost $6 billion at today's prices), making it Bitcoin's biggest corporate investor.
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While Saylor's foray into Bitcoin undoubtedly earned him some harsh (and sometimes valid) criticism from the mainstream media, the tech CEO has become the crypto community's darling, which earned him a nickname "permabull" for his perpetually bullish stance on Bitcoin. So if you, too, are a curious mind who'd like to learn more about one of Bitcoin's most loyal supporters, you have come to the right place! Read on to learn more about Michael Saylor's net worth, his success story, and BTC holdings.
Michael Saylor: education and early life
Michael Saylor was born in Lincoln, Nebraska in 1965 (58 years old at the time of writing). His father was an Air Force chief master sergeant, so Saylor's family frequently changed residence, living all over the world on various military bases and finally settling in Fairborn, Ohio, when Michael was 11 years old.
After high school, Michael Saylor decided to follow in his father's footsteps and went on to MIT on an Air Force scholarship. He graduated with a double degree in Aeronautics and Astronautics, and Science, Technology, and Society, finishing in the top 1 percent of his class with a 4.8 average out of a 5-point scale. However, due to his medical condition — a benign heart murmur — Saylor never became a pilot as he initially planned and instead took the gig at the consulting firm The Federal Group, Inc., where he put his engineering skills to work in computer simulation modeling, which was his college minor. After a year, Saylor left for a position as an internal consultant at DuPont, developing computer simulations that would help the company plan future actions in its key markets. While working on one of his models, Saylor successfully predicted a 1990 recession, although he was forced to make numerous tweaks to a program and run it several times on different devices because his management was hesitant to believe that the market crash was coming.
The creation of MicroStrategy
Impressed with the quality and precision of Saylor's predictions, DuPont offered him the position as an independent contractor. DuPont also agreed to provide funding to Saylor's new venture, MicroStrategy, which he set up together with his MIT fraternity brother, Sanju Bansal. The company started developing software for business intelligence, releasing its first product in 1991. A year later, MicroStrategy secured a lucrative $10 million contract with McDonald's, agreeing to build an application that would allow a fast-food giant to monitor the effectiveness of its promotional campaigns. That was when Saylor also realized that his company could develop a non-proprietary product instead of custom-built solutions, so businesses worldwide could use their own data to achieve competitive advantages in their markets.
The idea turned out to be a hit. MicroStrategy entered the market just as the demand for business intelligence solutions skyrocketed, and so did MSTR stock price after the founder duo took the company public in 1998. Due to his stake in MicroStrategy, Saylor became a multibillionaire: by early 2020, his net worth amounted to $7 billion.
Unfortunately, Saylor didn't get to enjoy his newfound fortune for a long time. In March 2000, around the time the dotcom bubble started to burst, the U.S. Securities and Exchange Commission (SEC) opened an investigation into MicroStrategy and Saylor over the company's accounting practices. The regulator found that MicroStrategy had been prematurely recognizing its revenue in violation of Generally Accepted Accounting Principles (GAAP), which forced the company to restate its financial results for the preceding two years. The restatement showed that MicroStrategy had actually been operating at a loss rather than the profit it had previously reported, which hammered its stock and cut Michael Saylor's net worth by $6 billion.
A few months later, Saylor settled with the SEC for $350,000 in penalties and a personal disgorgement of $8.3 million without admitting or denying the findings alleged. Although his personal net worth never fully recovered, MicroStrategy has successfully weathered the storm and even pursued aggressive expansion, going into the markets of mobile software, data mining, and cloud-based services
Saylor's big bet on Bitcoin
In August 2020, Michael Saylor announced that MicroStrategy would become the first major corporation to invest a large portion of its treasury in Bitcoin, marking a significant milestone in the mainstream corporate adoption of cryptocurrency.
“After scientifically studying everything on Earth, I’ve concluded Bitcoin is the best inflation hedge,” Saylor told CoinDesk. “We buy bitcoin as fast as we can with whatever money we find lying around.”
In a bold call, Saylor once made a prediction that the bitcoin market will one day reach $100 trillion, a 100x increase from the entire crypto market cap at the time of writing. True to his word, MicroStrategy CEO went on a two-year bitcoin buying spree by selling the company's debt to scoop more "digital gold." As a result, MicroStrategy's stock became a proxy for investing in bitcoin, moving up and down in lockstep with the biggest cryptocurrency.
Despite his belief in Bitcoin, Saylor maintains a critical stance on Ethereum. During the 2022 Blockchain Economy Istanbul conference, the American entrepreneur questioned the protocol's technical reliability and ethical soundness. He pointed out Ethereum's extensive roadmap of three to four years, which, in Saylor's opinion, means that it "doesn’t look like it's going to be completed or stable for another 36 months."
"'Ethically sound' means I need to know that nobody could change [the protocol], which includes Vitalik. I need to know that no one at the Ethereum Foundation, no individual can change the protocol because if they could change the protocol, it makes it a security and if it makes it a security, then it’s not going to become global money," Saylor added.
Why did Saylor step down as MicroStrategy CEO?
In 2022, Michael Saylor resigned as CEO of MicroStrategy after a release of an earnings report, which revealed a $917 million loss caused by a negative return on the firm's Bitcoin investments. Nevertheless, Saylor remained executive chairman of MicroStrategy, while the company's president Phong Le assumed the role of CEO.
While some observers speculated that MicroStrategy's bitcoin accumulation was over with Saylor's departure, it quickly became apparent that it was not the case. If anything, now the stubborn founder has even more time to focus on the company’s strategy to acquire and hold Bitcoin, while the new CEO oversees the legacy software business.
“I believe that splitting the roles of Chairman and CEO will enable us to better pursue our two corporate strategies of acquiring and holding Bitcoin and growing our enterprise analytics software business,” Saylor said at the time.
Michael Saylor's net worth in 2023
At the time of writing, Saylor's estimated net worth is $1.5 billion, as reported by Forbes's real-time billionaire net worth tracker. In 2023, Saylor briefly dropped off the list because of the crypto crash but rebounded due to BTC price appreciation that pushed up his company's stock.
In October 2020, Saylor disclosed that he personally bought 17,732 bitcoins for $175 million at an average purchase price of $9,882. At the time of writing, Saylor hasn't sold any of his BTC, and his personal Bitcoin holdings are now worth $658 million.
How did Michael Saylor build his net worth?
As former CEO and co-founder of MicroStrategy, Michael Saylor net worth is largely tied to the performance of its stock — when the company went public in 1998, he owned over 39,521 units of the company worth over $14 million at the time. MicroStrategy, a business intelligence firm that had been one of the high-flyers during the dotcom era, made Saylor a multibillionaire in the late 90s, but then tanked his wealth shortly after the bubble burst, spooking the markets and shaking investors' confidence in the tech sector for years ahead.
Another significant part of Saylor's wealth comes from his foray into Bitcoin: as of 2023, his personal holdings of Bitcoin exceeded 121,044 BTC, substantially contributing to the entrepreneur's wealth.
Finally, as the CEO and then executive chairman of MicroStrategy, Saylor receives a handsome salary and generous bonuses for his tireless leadership of the company.
Saylor's philanthropy and corporate giving
In 1999, Michael Saylor established the Saylor Foundation (later renamed as Saylor Academy), which is a non-profit organization that offers free education in the form of an assembly of online courses from the world's most renowned institutions, including Carnegie Mellon University and Massachusetts Institute of Technology. The Saylor Academy also offers online degrees through cooperation with other organizations.
Interestingly, Michael Saylor is also the author of several books that focus on business strategy and entrepreneurship, namely The Mobile Wave: How Mobile Intelligence Will Change Everything and What Is Money? The Saylor Series. The first book, which found itself on the New York Times Best Seller list in August 2012, explores trends in mobile technology and predicts that the fifth wave of computer technology would alter forever entire industries and societies. The second book, co-authored with Robert Breedlove, paints a broad picture of the changing nature of money, taking the reader on a lengthy journey from the Stone Age to the creation of Bitcoin with the aim to fully capture the historic significance of the first cryptocurrency.
Bottom line
A successful entrepreneur, author, and staunch Bitcoin evangelist, Michael Saylor is widely recognized as one of the most influential voices in the crypto space. Saylor's adoption of Bitcoin as a primary reserve asset for his software company, MicroStrategy, helped trigger an institutional interest in Bitcoin, elevating the asset to its 2021 bullish highs.
As of 2023, Michael Saylor's net worth is estimated at $1.5 billion, a testament to his influence in the tech and cryptocurrency industries.
If you would like to learn more about the net worth of other crypto personalities, take a look at our articles on Vitalik Buterin of Ethereum, Sergey Nazarov of Chainlink, Kevin O'Leary of Shark Tank, and Crypto Hasbulla.
