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Michael Saylor: The Man Behind MicroStrategy’s Bitcoin Investment

Writer's picture: Steven WalgenbachSteven Walgenbach


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Michael Saylor is an American entrepreneur and business executive who is widely known for his role as the co-founder and executive chairman of MicroStrategy. He was born on February 4, 1965, and has made a name for himself as a former rocket scientist and business analytics software executive. Saylor is also an author and philanthropist who has a background in computer simulation, business strategy, and public policy.

Saylor became a billionaire again in 2020 by investing in bitcoin and other cryptocurrencies. He is a Bitcoin maximalist who believes that the cryptocurrency is the exit strategy. Saylor has been very vocal about his support for Bitcoin and has been advocating for its adoption by businesses and institutions. He is also known for his bold moves in the cryptocurrency market, including investing over $1 billion of MicroStrategy’s funds into Bitcoin.


#Bitcoin is the Exit Strategy. pic.twitter.com/aauBgmE25a — Michael Saylor⚡️ (@saylor) February 20, 2024

Despite facing criticism for his risky investment strategies, Saylor remains confident in his decisions and continues to push for the adoption of Bitcoin. His influence in the cryptocurrency world has made him a prominent figure in the industry, and his success as an entrepreneur has earned him a place among the world’s wealthiest individuals.

Early Life and Education

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

Saylor enrolled at the Massachusetts Institute of Technology (MIT) in 1983 on an Air Force ROTC scholarship. During his time at MIT, he studied aerospace engineering and computer science. He received a Bachelor of Science degree in Aeronautics and Astronautics in 1987.

After graduation, he worked briefly for the consulting firm The Boston Group before founding MicroStrategy, a business intelligence software company, in 1989.

Saylor’s early life and education played a significant role in shaping his career. His exposure to the Air Force and his interest in aerospace engineering influenced his decision to pursue a career in technology. His education at MIT provided him with the technical skills necessary to start his own company.

Business Ventures

MicroStrategy

Michael Saylor is the executive chairman and co-founder of MicroStrategy, a business intelligence, mobile software, and cloud-based services company. Saylor served as the company’s chief executive officer from 1989 to 2022. Under his leadership, MicroStrategy became one of the leading companies in the business intelligence industry.

One of Saylor’s most notable business ventures was his decision to invest heavily in Bitcoin. In August 2020, MicroStrategy announced that it had purchased 21,454 bitcoins for $250 million. Since then, the company has continued to invest in Bitcoin and now holds over 100,000 bitcoins, making it the largest corporate holder of the cryptocurrency.

Other Investments

In addition to his work with MicroStrategy, Michael Saylor has made several other notable investments. He is a co-founder of Alarm.com, a home security technology company, and he has also invested in several other technology startups.

Saylor is also a prominent philanthropist. He has donated millions of dollars to various causes, including education and medical research. In 2012, he founded the Saylor Foundation, which provides free online courses to anyone in the world.

Overall, Michael Saylor is a successful entrepreneur and investor who has made significant contributions to the business world. His investments in Bitcoin and other technology startups have demonstrated his ability to identify promising opportunities and capitalize on them.

Advocacy for Bitcoin

Michael Saylor is a well-known advocate for Bitcoin. He has been vocal about his support for the cryptocurrency and has taken several steps to promote its adoption. This section will explore some of the ways in which Saylor has advocated for Bitcoin.

Bitcoin Holdings

Saylor’s company, MicroStrategy, has been one of the most prominent institutional investors in Bitcoin. In 2020, the company acquired $250 million worth of Bitcoin as a reserve asset. Since then, MicroStrategy has continued to add to its Bitcoin holdings, and as of June 30, 2022, the company’s Bitcoin holdings had a market value of $2.451 billion.


$MSTR is powered by #Bitcoin. pic.twitter.com/lmVxM3wK7w — Michael Saylor⚡️ (@saylor) February 19, 2024

Public Statements

Saylor has also been vocal about his support for Bitcoin in public statements. He has given several interviews and speeches in which he has discussed the benefits of Bitcoin and the potential risks of fiat currencies. In a 2021 interview with CNBC, Saylor stated that Bitcoin was “the dominant digital monetary network in the world” and that it was “the best store of value in the history of the world.”

Educational Initiatives

Saylor has also taken steps to educate others about Bitcoin. In 2020, he launched the Bitcoin for Corporations initiative, which was aimed at helping other companies to add Bitcoin to their balance sheets. The initiative included a series of webinars and educational resources that were designed to help companies understand the benefits of Bitcoin as a reserve asset.

In addition to this, Saylor has also written a book titled “The Bitcoin Standard,” which explores the history of money and the potential of Bitcoin as a new monetary standard. The book has been praised for its clear and concise explanations of complex economic concepts.

Overall, Michael Saylor’s advocacy for Bitcoin has played a significant role in promoting its adoption. Through his company’s Bitcoin holdings, public statements, and educational initiatives, Saylor has helped to legitimize Bitcoin as a viable asset class and store of value.

Legal and Regulatory Insights

Michael Saylor is no stranger to legal and regulatory issues, having been involved in several high-profile cases throughout his career. One such case is the lawsuit brought against him and his company, MicroStrategy, by the District of Columbia’s attorney general in 2024. The lawsuit alleges that Saylor and MicroStrategy colluded to hide taxable income from the District of Columbia, resulting in a loss of $25 million in tax revenue.

Saylor has vehemently denied these allegations, stating that MicroStrategy has always been transparent in its financial reporting and that the company has complied with all applicable tax laws. He has also hired top legal representation to defend him and MicroStrategy in this case, including a former US Secretary of Labor and the son of the late Supreme Court Justice Antonin Scalia.

In addition to this lawsuit, Saylor has also been vocal about his concerns regarding the regulatory environment surrounding cryptocurrencies. He has stated that he believes that the lack of regulatory clarity in this space is hindering its growth and adoption. Saylor has also been critical of the practice of lending out cryptocurrencies, citing concerns about counterparty risk, regulatory issues, and legal and accounting issues.

Despite these challenges, Saylor remains committed to the cryptocurrency space and to MicroStrategy’s role in it. He has stated that he believes that cryptocurrencies have the potential to transform the global financial system and that MicroStrategy will continue to be at the forefront of this transformation.

Philanthropy and Personal Interests

Michael Saylor is not only a successful businessman but also a philanthropist who has been actively involved in various charitable activities. He has donated millions of dollars to different causes, including education, healthcare, and poverty alleviation.

One of his notable contributions is the Saylor Academy, a non-profit organization that provides free online courses to individuals worldwide. The academy offers over 100 courses in various fields, including business, computer science, and mathematics.

Saylor has also been a strong advocate for Bitcoin and its potential to revolutionize the financial industry. He has invested heavily in the cryptocurrency and even converted MicroStrategy’s cash reserves into Bitcoin, a move that has attracted both praise and criticism.

Apart from his business and philanthropic activities, Saylor is also a pilot and car enthusiast. He owns several luxury cars, including a Lamborghini Aventador and a McLaren 650S. Saylor is also an avid traveler and has visited over 100 countries, often using his private jet to get around.

Overall, Michael Saylor’s philanthropic efforts and personal interests reflect his passion for innovation and his desire to make a positive impact on the world.

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