Michael Saylor

About Michael Saylor

Michael Saylor was born February 4, 1965,^[3] in Lincoln, Nebraska.^[4] During his early childhood years, he lived on Air Force bases around the world because his father was an Air Force chief master sergeant. Saylor’s parents raised him, along with his brother and sister, as Southern Baptists. Their home included a strict chore regimen, and swearing, smoking, and drinking were not allowed.^[3] 

Saylor has described his father as a typical, disciplined military seargent, saying, “I can’t remember a single time in my life where my father ever said an untruth or tried to slide by with a half effort on anybody or with everything, which is kind of interesting, you know, because you don’t realize how unique that is until you grow up, and then you realize that people are always, like, sliding by, a negotiation or something, but my father never cut a corner, ever.”^[5] 

Saylor loved reading as a kid but had a strong preference for comic books. His parents offered to pay him a dime for every regular book he read. He said, “I learned quickly that if I read lots of normal books. I could get the money to buy comic books, and I must have read one summer a hundred books, just lots of books.”^[5] 

When Saylor was in seventh grade, his family moved to Fairborn, Ohio, a small town near the Wright-Patterson Airforce base. While living in Fairborn, he enjoyed singing in his church and school choirs and playing in rock bands. Saylor plays the guitar, trombone, and piano.^[5] He attended Park High School in Fairborn. He graduated as valedictorian and was voted “Most Likely to Succeed.”^[4] 

Education and Early Career

After high school, Saylor attended MIT on a full ROTC scholarship. He studied aeronautics, astronautics, science, technology, and society and was a member of the Theta Delta Chi fraternity.^[3] Saylor’s thesis, “A Mathematical Model of a Renaissance Italian City State,” explored computer simulation technology and public policy. He graduated with honors in 1987.^[4]   

After earning his degree, Saylor hoped to be a pilot in the Air Force, but a benign heart murmur made that path impossible. Instead, he began working as a consultant, focusing on using computer simulations to support strategic decision-making. He consulted for companies such as DuPont, Dow, and Exxon.^[6]   

Early Success at MicroStrategy

In 1989, Saylor used funding from DuPont to start MicroStrategy with his former roommate and fraternity brother, Sanju Bansal. The company initially provided software for data mining before focusing on business intelligence software.^[3] 

MicroStrategy’s first major success was a $10 million contract with McDonald’s. McDonald’s used MicroStrategy’s software to learn which menu items were more popular in certain regions of the country. After the successful contract with McDonald’s, Saylor’s company landed several contracts with Fortune 500 companies.^[7]  

According to Saylor, MicroStrategy doubled its revenue every year between 1994 and 1997. The company went public in 1998 with shares priced at $12 each. On its first day of trading, the value of the shares doubled by midday.^[3]  

While MicroStrategy grew, Saylor received plenty of media attention for his role as MicroStrategy’s CEO. Several outlets, including KPMG, Ernst &Young, and Red Herring Magazine, recognized him as “Entrepreneur of the Year” or a “Top 10 Entrepreneur.”^[8] By 2000, Saylor’s net worth reached $7 billion due to his stake in MicroStrategy.^[5]  

Significant Losses

In March 2000, the SEC charged Saylor and his company with inaccurate financial reporting. The charge caused MicroStrategy’s stock value to plummet, and Saylor’s net worth dropped by an estimated $6 billion in one day.^[9]  

After the company’s losses, Saylor commented, saying, “If I was a better manager, if I had had more experience, if I was more careful, if I was more competent, maybe this wouldn’t have happened. It’s like being a parent whose children were playing in the front yard, and one of the kids got struck by lightning, and now he’s dead. You didn’t have a lightning rod on your roof, because you were planning to take care of doing that next year. Now people walk by your house, point, and say, ‘Look, that’s where the kid got struck by lightning.’ It’s an awful feeling.”^[10] 

An economic downturn followed the huge drop in MicroStrategy’s value as other tech companies similarly lost value. MicroStrategy was able to survive by cutting costs, reducing its workforce, broadening its customer base, and changing its growth strategy, prices, products, and leadership style.^{[11] [12]}  

Crypto Strategy

Saylor has been a vocal advocate of cryptocurrency. In 2020, he tweeted, “The destiny of money is to be encrypted.”^[13]  

Because of his belief in cryptocurrency, he has led his company to become one of the most prominent investors in Bitcoin. In August 2020, MicroStrategy invested $250 million in Bitcoin, which was the first of many purchases.^[14] By September 2022, the company had spent $3.98 billion on Bitcoin.^[15]   

At a 2021 Bitcoin conference in Miami, Saylor said, “We say Bitcoin is hope. Bitcoin fixes everything . . . that certainly was the case with our stock . . . it imbued life into the company . . . morale was dramatically boosted. We just had the best first quarter we’ve had in a decade.”^[16] 

In December 2022, MicroStrategy sold some of its Bitcoin holdings for the first time after the price of the cryptocurrency dropped significantly throughout 2022. The company sold 704 Bitcoin for $11.8 million.^[17]  

In 2022, Saylor stepped down as CEO but remained the executive chairman. As executive chairman, he said he planned to focus on the company’s Bitcoin acquisition strategy.^[18] 

Other Ventures

In addition to his role at MicroStrategy, Saylor founded Alarm.com, a pioneering home automation and security company that was sold to a venture capital firm for $27.7 million in 2009.^[19] Saylor also founded Angel.com, a cloud-based interactive voice response service provider that was acquired by Genesys Telecommunications Laboratories for $110 million in 2013.^[4]

In 2012, Saylor published The Mobile Wave: How Mobile Intelligence Will Change Everything, which appeared on The New York Times’ and The Wall Street Journal’s best seller lists.^[4]

In 1999, Saylor created The Saylor Foundation, a charitable organization that has supported several causes, including refugee relief, education, environmental conservation, and children’s health. Through the foundation’s Saylor Academy (Saylor.org), more than 1.4 million students worldwide have received free education and professional development courses.^[4]

Controversies

In 2022, the Washington D.C. Attorney General sued Saylor for tax fraud. The lawsuit accused Saylor of avoiding more than $25 million in D.C. taxes by illegally pretending to be a resident of other areas.^[20] 

Michael Saylor Today

Saylor continues to act as executive chairman at MicroStrategy. He remains an active advocate of Bitcoin. While speaking at the Bitcoin 2023 conference, Saylor stated that he believes Bitcoin is the dominant digital commodity. He is especially interested in Bitcoin’s Ordinal technology, a technology similar to NFTs.^[21]  

Saylor is also a regular guest on multiple podcasts, including the Lex Fridman Podcast,^[22] PBD Podcast,^[23] and the Pomp Podcast,^[24] where he discusses his ideas surrounding cryptocurrency.