Michael Saylor: From Software Entrepreneur to Leader in the Crypto Industry

Michael Saylor, the creator of Strategy (MicroStrategy), is one of the most influential figures in the world of technology and business intelligence. His career is filled with visionary decisions, strategic investments, and innovations that elevated him from a young entrepreneur with software ambitions to a leader in the cryptocurrency industry.

Born in 1965 in Lincoln, Nebraska, to a military family, Saylor spent his childhood at various U.S. Air Force bases around the world. By his teenage years, his family settled at Wright-Patterson Air Force Base near Dayton, Ohio—the birthplace of aviation and home to the Wright brothers. He graduated from high school as valedictorian and was also nominated by his peers as "most likely to succeed."

Saylor attended the Massachusetts Institute of Technology (MIT) on a scholarship from the U.S. Air Force, where he graduated with high honors in 1987 with dual degrees in aeronautics and astronautics, as well as science, technology, and society. During his time at MIT, he was involved in a rock band and learned to fly gliders. His thesis, titled "Mathematical Model of a Renaissance Italian City-State," showed his early interest in applying computer simulations in strategic decision-making.

The Creation of MicroStrategy

After graduating from MIT, Saylor began his career in the consulting industry, working for companies like DuPont, Dow, and Exxon, focusing on building computer simulations to support their strategic decisions. In 1989, at the age of 24, he founded MicroStrategy, combining his passion for technology and business and the application of computer simulations in corporate strategy.

Under his leadership, MicroStrategy established itself as a leader in business intelligence software solutions, offering innovative approaches, including relational online analytical processing (ROLAP). The company quickly gained popularity, going public in 1998 (NASDAQ: MSTR). Today, MicroStrategy offers data analytics, mobile technologies, and cloud computing solutions to thousands of organizations worldwide.

Bitcoin Discovery

In 2020, Saylor made a big leap when he decided to invest part of his company’s cash reserves into Bitcoin. This move became known as one of the first major corporate bets on cryptocurrency. Initially, MicroStrategy bought $250 million worth of Bitcoin, completely changing the company's financial strategy and deciding to invest a significant portion of its assets into crypto.

By 2021, MicroStrategy owned over 100,000 bitcoins, and by 2025, the company held more than 538,000 bitcoins worth approximately $47 billion. This made MicroStrategy the largest corporate holder of Bitcoin in the world.

Saylor actively spoke out in defense of Bitcoin, referring to it as a "primary asset" for the modern economy. To him, Bitcoin is "the best financial solution for the new generation."

Saylor's DCA Strategy

Michael Saylor is a strong proponent of the Dollar-Cost Averaging (DCA) strategy, which involves regularly purchasing assets at set intervals regardless of market conditions. According to Saylor, this strategy is ideal for investors who want to reduce the risk of large price fluctuations by making small, regular purchases instead of trying to time market highs and lows. Saylor uses this strategy for purchasing Bitcoin for MicroStrategy, buying cryptocurrency every 1-2 weeks with a focus on long-term results.

Bitcoin Purchases Over the Years

This strategy is convenient as it doesn’t require investors to monitor market movements daily. Instead, they regularly buy Bitcoin at a fixed amount, thereby building their position without worrying about short-term price fluctuations. Saylor believes that Bitcoin is an asset that will continue to increase in value in the long term, and by regularly purchasing Bitcoin with the DCA strategy, MicroStrategy will amass significant assets.

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MicroStrategy Rebranding

In line with his strategic vision for Bitcoin’s future and its role in the financial industry, in 2025, MicroStrategy underwent a significant shift in its corporate identity, rebranding itself as Strategy. This is not just a name change, but a completely new concept for the company. MicroStrategy’s strategy is now focused primarily on Bitcoin as a core asset, and the rebranding reflects the company’s commitment to positioning itself as a leader in the Bitcoin industry. Strategy’s mission is now to be a global hub for Bitcoin purchases and management, while continuing to offer innovations in technology and software solutions.

This rebranding is part of a larger strategy by Saylor to make MicroStrategy/Strategy a major player in the cryptocurrency market, continuing to increase its Bitcoin holdings and encouraging other institutional investors to follow suit. The rebranding highlights the company’s goal to become a key active participant in the cryptocurrency market, now entirely focused on Bitcoin and its future as a "primary asset."

Interest in MicroStrategy Shares

Although MicroStrategy is known for holding significant amounts of Bitcoin, interest in its shares is growing for another reason. Many crypto enthusiasts and institutional investors are buying shares of MSTR (MicroStrategy’s ticker on the stock exchange) because the company is much more profitable than Bitcoin itself.

This gives investors the opportunity to gain exposure to Bitcoin without taking on the risks associated with directly holding the cryptocurrency. Investing in MicroStrategy’s shares allows crypto enthusiasts to benefit from Bitcoin’s price movements but also from the profits the company generates through its software solutions and business intelligence. This makes MicroStrategy’s stock attractive to investors looking to combine stability and growth with crypto exposure.

Innovations and Patents

Michael Saylor is the inventor of over 48 patents and is credited as a pioneer in relational analytics. Under his leadership, MicroStrategy developed a number of innovative technologies in web analytics, mobile applications, cloud services, and the Internet of Things (IoT). He is also a co-founder of Alarm.com (NASDAQ: ALRM), one of the first home automation and security companies, and Angel.com, which was later sold for $110 million to Genesys Telecommunications Laboratories.

Books and Philanthropy

In 2012, Saylor published the book The Mobile Wave: How Mobile Intelligence Will Change Everything, which predicted the impact of mobile technologies, cloud services, and social networks on political and economic development. The book foresaw the rise of tech giants like Apple, Amazon, Facebook, and Google and their influence on industries and political structures worldwide.

In 1999, Saylor created The Saylor Foundation, which has donated millions of dollars to various philanthropic causes, including child healthcare, refugee assistance, education, environmental conservation, and support for the arts. The foundation also runs Saylor Academy, which offers free education and professional development courses to students around the world. To date, over 2 million students have used the academy's services.

Michael Saylor is an example of an entrepreneur who not only creates innovations in the business world but also has the courage to change his strategies to adapt to new technologies. His vision for the future of Bitcoin and his decision to invest in it is an example of strategic thinking and bold entrepreneurship. MicroStrategy’s holdings in Bitcoin continue to be a foundation for the company’s growth and stability, establishing it as a leader in the cryptocurrency industry.