Michael Saylor's profile

Michael Saylor

Michael Saylor is an entrepreneur, investor, strategist, author, and speaker on topics of technology, bitcoin, and business strategy. His early life and career are filled with contradictions; an unconventional upbringing on a west coast swing family that embraced individualism and pursued success through original thinking.

Known for his entrepreneurial and business acumen, Michael J. Saylor created and now heads MicroStrategy, a firm that offers corporate analytics, mobile applications, and cloud-based services. Saylor is the author of the 2012 book The Mobile Wave: How Mobile Intelligence Will Change Everything, which was published by HarperCollins.

Innovation through iteration is how Saylor builds his businesses. His later success came from building companies that are strategically and operationally sound with a focus on customer experience and value creation.

Saylor’s methodical approach combined with deep understanding of companies, markets, and individuals enables him to identify emerging trends, identify competitive advantages, and act on them before others can recognize and capitalize on them too.

Saylor’s early life and career

Michael started his life in Lincoln, Nebraska, on February 4, 1965.

In 1983, he was lucky to get an ROTC scholarship and enroll in the Massachusetts Institute of Technology (MIT).

He earned two degrees from the institution in 1987. The first was awarded in aeronautics and astronautics, while the second was awarded in science and technology.

Saylor also had flight training at Lackland Airforce Base, where he rose to the rank of Second Lieutenant in the United States Air Force. He adored the use of computer simulation in business forecasting in his institute’s system dynamics class.

“The future of big tech is digital property.”

Michael Saylor

Rather than continuing his flying career, he joined the Federal Group as a consultant in 1987. He was unable to fly due to a health issue. He was a computer modeler for a software business.

The computer enthusiast provided consulting services to businesses looking to incorporate new technology into their company planning and decision-making processes.

Saylor began his career at DuPont in 1988. In 1990, while advising for DuPont, he predicted a decline in the company’s main markets. The forecast was made feasible by the computer models he developed to help the business prepare for potential market forces shifts.

In 1989, Saylor founded the MicroStrategy Company in pursuit of business-oriented computer modeling technologies. The firm’s goal was to offer intelligent solutions to businesses. Saylor was the pioneer in developing Relational Online Analytical Processing (ROLAP).

  • Timeline

    1965: Michael J. Saylor (born February 4, 1965) is an American entrepreneur and business executive, who co-founded and leads MicroStrategy, a company which provides business intelligence, mobile software, and cloud-based services.


    1983: In 1983, Saylor enrolled at the Massachusetts Institute of Technology (MIT) on an Air Force ROTC scholarship.


    1987:  He graduated from MIT in 1987, with a double major in aeronautics and astronautics; and science, technology, and society.


    1987: A medical condition prevented him from becoming a pilot, 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.


    1988: In 1988, Saylor became an internal consultant at DuPont, where he developed computer models to help the company anticipate change in its key markets.


    1990: The simulations predicted that there would be a recession in many of DuPont’s major markets in 1990.


    1992: In 1992, MicroStrategy won a $10 million contract with McDonald’s to develop applications to analyze the efficiency of its promotions.


    1996: In 1996, Saylor was named KPMG Washington High-Tech Entrepreneur of the Year.


    1997:  In 1997, Ernst & Young named Saylor its Software Entrepreneur of the Year, and the following year, Red Herring Magazine recognized him as one of its Top 10 Entrepreneurs for 1998.


    1998: Saylor took the company public in June 1998, with an initial stock offering of 4 million shares priced at $12 each.


    1999: Saylor was also featured by the MIT Technology Review as an “Innovator Under 35” in 1999.


    1999: In 1999, Saylor established The Saylor Foundation (later named Saylor Academy), of which he is the sole trustee.


    2000: 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.


    2000: 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.


    2000: 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.


    2008: To support his goal of making free education available to all students, Saylor.org was launched in 2008 as the free education initiative of The Saylor Foundation.


    2012: Saylor authored the 2012 book The Mobile Wave: How Mobile Intelligence Will Change Everything.


    2012: 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.


    2012: 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, and was ranked number five in hardcover business books on the Wall Street Journal’s Best-Sellers list in July 2012.


    2016: As of 2016, Saylor has been granted 31 patents and has 9 additional applications under review.


    2020: 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.


    2020: MicroStrategy later added $175 million of Bitcoin to its holdings in September 2020 and another $50 million in early December 2020.


    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.


    2020: 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.

Michael Saylor and MicroStrategy

The firm’s goal was always to raise the intelligence level of businesses. MicroStrategy would help companies make smarter choices by integrating insights into every application. The new technologies would replace outdated ones that take too long and effort to analyze data.

Saylor built the firm to be a global leader in business analytics and mobile software, servicing clients all around the globe. Michael co-founded MicroStrategy with his college pal Sanju Bansal in 1989 with his DuPont consulting fees.

Although the firm’s initial primary function was data mining, it shifted emphasis in 1992. McDonald’s paid the company ten million dollars to create marketing campaign tracking software. The deal taught Saylor that MicroStrategy could build business intelligence tools to assist companies analyze their processes.

Microstrategy IPO

Throughout the 1990s, the company expanded and eventually became public in 1998. 

Michael sold four million MicroStrategy shares at a price of $12 per share. 

On the first trading day, demand for the shares pushed the price up 100%. His net worth hit $7 billion USD in the first quarter of 2000. By that time, he had amassed over 30,000 shares valued at over $4.8 million.

Judgment Charges against Microstrategy

In March 2000, the SEC filed a lawsuit against Michael and two other MicroStrategy directors.

Saylor allegedly filed financial reports for 1998 and 1999. Michael paid the SEC 350,000 USD in fines and 8.3 million USD in disgorgement nine months later.

However, he made no admissions. MicroStrategy was harmed by the case’s prominence. As a consequence, the founder’s net worth was reduced to $1 billion from $7 billion.

MicroStrategy’s Bitcoin Invest

Before February 2021, the company owned about 71,000 Bitcoin worth 3.3 billion USD. Moreover, the CEO has personally hodled 18,000 BTC.

Michael revealed in early April 2021 that MicroStrategy had purchased 15 million USD worth of BTC. See how much Bitcoin MicroStrategy has today in our live Bitcoin investments overview.

MicroStrategy’s stock price rose in reaction to its Bitcoin hodling. A single share cost 724 USD in mid-March 2021, up from 107 USD a year earlier.

Despite the BTC price drop in February 2021, Saylor firmly told CNBC that its market worth will one day reach 100 trillion USD from the current 1 trillion USD.

Why is he important in the Crypto world?

The man behind Microstrategy, Michael Saylor, is, without doubt, one of the most important people in the Crypto world. His knowledge of the industry, both past, and present, is unparalleled. Not only is he an active member in the online community, but he has also had a hand in raising over $100m in funding for key companies within the space.

Relevant tweets and phrases from Michael Saylor

Key phrases

“Bitcoin is a bank in cyberspace, run by incorruptible software, offering a global, affordable, simple, & secure savings account to billions of people that don’t have the option or desire to run their own hedge fund.”

Michael Saylor

“When I discovered bitcoin I thought this is digital gold on a big tech monetary network and it’s going to grow by a factor of a hundred. Then I thought, well, I should buy as much as I can…I was buying it and I was thinking I have to buy as much as I can, as fast as I can or someone will figure this out and I won’t be able to.”

“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.”

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