Michael Saylor
Saylor in 2022
Born	(1965-02-04) 4 February 1965 (age 60) Lincoln, Nebraska, U.S.
Alma mater	Massachusetts Institute of Technology (BSc)
Occupation	Executive chairman of MicroStrategy^[1]
Notable work	The Mobile Wave

Michael J. Saylor (born February 4, 1965) is an American entrepreneur and business executive. He is the executive chairman and co-founder of MicroStrategy, a company that provides business intelligence, mobile software, and cloud-based services.

Saylor was MicroStrategy's chief executive officer from 1989 to 2022. In 2000, Saylor was charged by the SEC with fraudulently reporting MicroStrategy's financial results for the preceding two years. He later reached a settlement with the SEC for $350,000 in penalties and $8.3 million in personal disgorgement.

Saylor is a bitcoin advocate and under Saylor MicroStrategy has spent billions of dollars to purchase over 500,000 bitcoins. In 2024, he paid a $40 million fine to settle a tax fraud suit. He authored the 2012 book The Mobile Wave: How Mobile Intelligence Will Change Everything. He is also the sole trustee of Saylor Academy, a provider of free online education.

Early life and education

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Saylor was born in Lincoln, Nebraska, on February 4, 1965, and spent his early years on various Air Force bases around the world, as his father was an Air Force chief master sergeant. When Saylor was 11, the family settled in Fairborn, Ohio, near the Wright-Patterson Air Force Base.^[2]^[3]

In 1983, Saylor enrolled at the Massachusetts Institute of Technology (MIT) on an Air Force Reserve Officers' Training Corps (ROTC) full scholarship. He joined the Theta Delta Chi fraternity, through which he met his future co-founder of MicroStrategy, Sanju Bansal.^[2]^[3] Saylor double majored in aeronautical & astronautical engineering and history of science.^[2]^[4]

A medical condition prevented him from becoming a pilot,^[2]^[3] and instead, he got a job with a consulting firm, The Federal Group, Inc. in 1987, where he focused on computer simulation modeling for a software integration company.^[4] In 1988, Saylor became an internal consultant at DuPont, where he developed computer models to help the company anticipate change in its key markets. The simulations predicted that there would be a recession in many of DuPont's major markets in 1990.^[2]^[4]

As of 2016, Saylor had been granted 31 patents and had nine additional applications under review.^[5]

MicroStrategy

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Using the funds from DuPont, Saylor founded MicroStrategy with Sanju Bansal, his MIT fraternity brother.^[3] The company began developing software for data mining, then focused on software for business intelligence. In 1992, MicroStrategy won a $10 million contract with McDonald's to develop applications to analyze the efficiency of its promotions. The contract with McDonald's led Saylor to realize that his company could create business intelligence software that would allow companies to use their data for insights into their businesses.^[3]^[4]^[2]^[6]^[7]

Saylor took the company public in June 1998, with an initial stock offering of 4 million shares priced at $12 each.^[8] The stock price doubled on the first day of trading.^[9] By early 2000, Saylor's net worth reached $7 billion, and the Washingtonian reported that he was the wealthiest man in the Washington D.C. area.^[2]

In 1996, Saylor was named KPMG "Washington High-Tech Entrepreneur of the Year".^[4]^[10] In 1997, Ernst & Young named Saylor its "Software Entrepreneur of the Year", and the following year, Red Herring Magazine listed him as one of its "Top 10 Entrepreneurs for 1998".^[11] Saylor was also listed by the MIT Technology Review as an "Innovator Under 35" in 1999.^[12]

On March 20, 2000, MicroStrategy announced that it would restate its financial results for the previous two years.^[13] MicroStrategy’s stock price, which had soared from $7 per share to as high as $333 per share over the course of a year, plummeted 62%, dropping to $120 per share in a single day. This significant decline is considered one of the key events marking the burst of the dot-com bubble.^[14] By August 2000, approximately two dozen class action securities fraud actions were filed in the United States District Court for the Eastern District of Virginia against the company.^[15] In December 2000, the U.S. Securities and Exchange Commission filed fraud charges against MicroStrategy and its executives.^[16] MicroStrategy ultimately settled with the SEC, agreeing to hire an independent director to ensure ongoing regulatory compliance.^[17]^[18]

After his leadership was criticized by several major investors in 2014, Saylor has since opted for a symbolic one-dollar salary without any cash bonuses, but with stock options.^[19] According to Bloomberg, Saylor exercised those option for around $400 million in the first quarter of 2024.^[20]

On August 8, 2022, Saylor assumed the title of executive chairman of MicroStrategy and appointed Phong Le, the company's president, to succeed him as CEO. Saylor said in a press release, "As Executive Chairman I will be able to focus more on our bitcoin acquisition strategy and related bitcoin advocacy initiatives, while Phong will be empowered as CEO to manage overall corporate operations."^[21]

As of November 2024, he owns 19,998,580 shares (Class B common stock), about 9.9% of the total outstanding shares, and has approximately 45% of the voting power. This increase in shares is mainly due to a MSTR stock split on August 8th 2024 at a 10:1 ratio for both class A and B shares. ^[22]

In February 2025, the company rebranded from MicroStrategy to Strategy.^[23]

Bitcoin advocacy

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Saylor is an advocate of bitcoin, stating that he believes it will displace gold as a non-governmental store of value.^[24] Saylor has said that "capital preservation" is Bitcoin's utility and compares buying it to buying a home in a city everyone wants to move to. According to Saylor, bitcoin is "the apex property of the human race."^[25]

On MicroStrategy's quarterly earnings conference call in July 2020, Saylor announced his intention for MicroStrategy to explore purchasing bitcoin, gold, or other alternative assets instead of holding cash. The following month, MicroStrategy used $250 million from its cash stockpile to purchase 21,454 bitcoins.^[26]

MicroStrategy later added $175 million of bitcoin to its holdings in September 2020 and another $50 million in early December 2020. On December 11, 2020, MicroStrategy announced that it had sold $650 million in convertible senior notes, taking on debt to increase its Bitcoin holdings to over $1 billion worth. On December 21, 2020, MicroStrategy announced their total holdings include 70,470 bitcoins purchased for $1.125 billion at an average price of $15,964 per bitcoin.^[27] As of February 24, 2025 holdings include 499,096 bitcoins acquired for $27.95 billion at an average price of $62,473 per bitcoin.^[28]

Despite criticism from skeptics like Peter Schiff, Saylor remains confident in Bitcoin as an inflation hedge and a transformative financial asset. MicroStrategy has significantly increased its Bitcoin holdings, recently announcing a $700 million debt sale to further invest in the cryptocurrency. Saylor has also expressed his willingness to advise on crypto policy, potentially serving on a crypto advisory council for the Trump administration.^[29]

Political views

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COVID-19 response criticism

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In a 3,000-word memo to all MicroStrategy employees on March 16, 2020, entitled "My Thoughts on COVID-19," Saylor criticized countermeasures then being recommended against the disease, saying that it is "soul-stealing and debillitating [sic] to embrace the notion of social distancing & economic hibernation" and predicting that in the worst-case scenario, global life expectancy would only "click down by a few weeks." Saylor also refused to close MicroStrategy's offices unless he was legally required to do so. The full content of the memo appeared on Reddit for only a few minutes and was reposted in the Washington Business Journal.^[30]^[31]

The Mobile Wave

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In June 2012, Saylor released The Mobile Wave: How Mobile Intelligence Will Change Everything, published by Perseus Books, which discusses trends in mobile technology and their future impact on commerce, healthcare, education, and the developing world.^[32] The book appeared on the New York Times Best Seller list, where it was ranked number seven in hardcover non-fiction books in August 2012,^[33] and was ranked number five in hardcover business books on the Wall Street Journal's Best-Sellers list in July 2012.^[34]

Saylor Academy

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In 1999, Saylor established The Saylor Foundation (later named Saylor Academy), of which he is the sole trustee. Saylor.org was launched in 2008 as the free education initiative of The Saylor Foundation.^[35]

Awards and recognition

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Saylor has received several awards and recognition throughout his career. In 1996, he was named KPMG High Tech Entrepreneur of the Year.^[4] His leadership at MicroStrategy earned him a spot on Ernst & Young's Entrepreneur of the Year list in 1997.^[36] Additionally, Saylor has been featured in various industry publications and lists, recognizing his influence and impact on the tech industry and digital currency advocacy.^[10]^[11]^[12]

Controversies

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SEC investigation

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In March 2000, the U.S. Securities and Exchange Commission (SEC) brought charges against Saylor and two other MicroStrategy executives for the company's inaccurate reporting of financial results for the preceding two years.^[37] In December 2000, Saylor settled with the SEC without admitting wrongdoing by paying $350,000 in penalties and a personal disgorgement of $8.3 million.^[38]^[39]^[40] As a result of the restatement of results, the company's stock declined in value and Saylor's net worth fell by $6 billion.^[41]^[42]

District of Columbia tax fraud lawsuit

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On August 31, 2022, the Attorney General for the District of Columbia sued Saylor for tax fraud, accusing him of illegally avoiding more than $25 million in D.C. taxes by pretending to be a resident of other jurisdictions during the years 2005 to 2021. He initially claimed he resided in Virginia during the period, then later claimed that he resided in Florida.^[43] MicroStrategy was accused of collaborating with Saylor to facilitate his tax evasion by misreporting his residential address to local and federal tax authorities and failing to withhold D.C. taxes.^[44] Saylor issued a statement saying: "I respectfully disagree with the position of the District of Columbia and look forward to a fair resolution in the courts."^[45] In June 2024, Saylor settled the tax dispute by agreeing to pay a $40 million fine.^[43]

References

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^ "Leadership". microstrategy.com. MicroStrategy. 2013. Retrieved 22 February 2013.
^ ^a ^b ^c ^d ^e ^f ^g Jaffe, Harry (1 March 2000). "The Seven Billion Dollar Man". The Washingtonian. Retrieved 25 January 2013.
^ ^a ^b ^c ^d ^e Leibovich, Mark (6 January 2002). "MicroStrategy's CEO Sped to the Brink". The Washington Post. Retrieved 5 August 2024.
^ ^a ^b ^c ^d ^e ^f Glasser, Jeff (15 July 1996). "From the Ground Up and Up". The Washington Post. Archived from the original on 31 August 2000. Retrieved 26 January 2013.
^ "Patents by Inventor Michael J. Saylor". Justia.com. Retrieved 13 May 2016.
^ Salter, Chuck (31 March 2000). "People and Technology – MicroStrategy Inc". Fast Company. Retrieved 25 January 2013.
^ Stewart Alsop (8 September 1997). "Now I know how a real visionary sounds". CNNMoney.com. CNN. Retrieved 25 January 2013.
^ "Initial Public Offerings Key Data". NASDAQ. 11 June 1998. Archived from the original on 8 March 2012. Retrieved 27 January 2013.
^ Mark Leibovitch (9 August 1998). "A Journey Into the Secret Heart of Capitalism". Washington Post. Retrieved 21 September 2016.
^ ^a ^b Stan Hinden (6 July 1998). "Transforming information into another public utility". New Straits Times. Retrieved 19 February 2013.
^ ^a ^b "Michael Saylor". The Washington Post. 21 June 2000. Retrieved 19 February 2013.
^ ^a ^b "Michael J. Saylor, 34". MIT Technology Review. Archived from the original on 7 February 2022. Retrieved 19 February 2013.
^ Hilzenrath, David S. (March 22, 2000). "For MicroStrategy, A Matter of Timing". The Washington Post.
^ "MicroStrategy plummets". CNN Money. March 20, 2000.
^ In re Microstrategy Inc. Securities Litigation, No. CIV.00-473-A | Casetext Search + Citator (Court case). Archived from the original on 2024-12-28. Retrieved 2025-01-01.
^ "SEC Brings Civil Charges Against MicroStrategy, Three Executive Officers for Accounting Violations" (Press release). U.S. Securities and Exchange Commission. December 14, 2000.
^ Lau, Debra (December 18, 2000). "Forbes Faces: Michael Saylor". Forbes.
^ Hilzenrath, David S. (December 15, 2000). "Saylor, Associates Settle Fraud Charges". The Washington Post.
^ Heath, Thomas (September 8, 2014). "MicroStrategy CEO reduces pay to $1 from $875,000 following criticism of stewardship". The Washington Post.
^ Kharif, Olga; Contiliano, Tom (April 24, 2024). "MicroStrategy's Saylor Reaps a Stock Windfall During Bitcoin's Record Run". Bloomberg News. Archived from the original on 29 April 2024.
^ Sigalos, MacKenzie (August 2, 2022). "MicroStrategy CEO Saylor moves to chairman role, focusing on strategy and bitcoin". CNBC. Retrieved August 9, 2022.
^ name="Fintel-2024-11-22">SEC Filing, Fintel Research (November 22, 2024). "MicroStrategy CEO Saylor Institutional Ownership". Fintel. Retrieved November 24, 2024.
^ Strategy (2025-02-05). "MicroStrategy is now Strategy".
^ "Michael Saylor: Bitcoin to Replace Gold This Decade". FXEmpire. 2021-11-19. Retrieved 2024-01-14 – via Yahoo Finance.
^ "Bitcoin is the best investment asset: Michael Saylor". Yahoo Finance. 2024-03-12. Retrieved 2024-03-14.
^ Medici, Andy (11 August 2020). "MicroStrategy buys $250M in Bitcoin as CEO says it's superior to cash". Washington Business Journal. American City Business Journals. Retrieved 15 September 2020.
^ "MicroStrategy Announces Over $1B in Total Bitcoin Purchases in 2020". MicroStrategy. Retrieved 2020-12-22.
^ "MicroStrategy Acquires Additional 19,452 Bitcoins for $1.026 Billion". MicroStrategy. Retrieved 2024-09-20.
^ Qureshi, Mehab (2024-12-18). "Michael Saylor Says He's Willing to Advise Trump Administration on Crypto: 'I've Met With A Lot of People..'". TheStreet Crypto: Bitcoin and cryptocurrency news, advice, analysis and more. Retrieved 2024-12-18.
^ Medici, Andy (19 March 2020). "MicroStrategy CEO Michael Saylor questions 'dizzying' national response to coronavirus outbreak in lengthy staff email". Washington Business Journal. American City Business Journals. Retrieved 15 September 2020.
^ Wong, Julia Carrie; Strauss, Daniel (18 March 2020). "The tech execs who don't agree with 'soul-stealing' coronavirus safety measures". The Guardian. Retrieved 15 September 2020.
^ Ross Joynt, Carol (27 June 2012). "MicroStrategy CEO Michael Saylor's "The Mobile Wave" Examines the Implications of Mobile Technology". The Washingtonian. Retrieved 12 February 2013.
^ "Best Sellers — Hardcover Nonfiction". The New York Times. 5 August 2012. Retrieved 12 February 2013.
^ "Best-Selling Books, Week Ended July 15". The Wall Street Journal. 20 July 2012. Retrieved 12 February 2013.
^ "About the Saylor Foundation". saylor.org. Saylor Foundation. Retrieved 21 February 2013.
^ "Michael Saylor: Michael Saylor Net Worth, Biography, Age, Spouse, Children & More". Goodreturns. Retrieved November 14, 2024.
^ David S. Hilzenrath (14 April 2000). "SEC Investigating MicroStrategy". The Washington Post. Retrieved 29 January 2013.
^ Debra Lau (18 December 2000). "Forbes Faces: Michael Saylor". Forbes.com. Retrieved 25 January 2013.
^ David S. Hilzenrath (15 December 2000). "Saylor, Associates Settle Fraud Charges". The Washington Post. Retrieved 29 January 2013.
^ "SEC Brings Civil Charges Against MicroStrategyand Three Executive Officers for Accounting Violations". sec.gov. U.S. Securities and Exchange Commission. 14 December 2000. Retrieved 19 February 2013.
^ Plotz, David (23 March 2000). "Michael Saylor MicroStrategy's cult leader". Slate. Retrieved 19 February 2013.
^ Yang, Catherine (8 February 2004). "MicroStrategy's Second Wind". Businessweek.com. Bloomberg. Archived from the original on October 25, 2012. Retrieved 25 January 2013.
^ ^a ^b Laris, Michael (3 June 2024). "Bitcoin billionaire, firm to settle D.C. tax fraud suit for $40 million". The Washington Post. ISSN 0190-8286. Archived from the original on 12 June 2024. Retrieved 3 June 2024.
^ "AG Racine Sues DC-Based Billionaire Michael Saylor & Software Company Microstrategy for Evading More Than $25 Million in District Taxes". oag.dc.gov. Retrieved 1 September 2022.
^ Feiner, Lauren (31 August 2022). "MicroStrategy Chair Michael Saylor accused of evading $25 million in taxes by DC attorney general". CNBC.

External links

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