Michael Saylor is an American entrepreneur, business executive, and prominent advocate for Bitcoin. He is the co-founder and Executive Chairman of Strategy Inc. (formerly MicroStrategy), a publicly traded business intelligence firm that gained global recognition for adopting Bitcoin as its primary treasury reserve asset.
Saylor is widely regarded as one of the most influential institutional proponents of Bitcoin, credited with pioneering the corporate adoption of digital assets through his “Bitcoin Strategy.”
Overview
Saylor is best known in the cryptocurrency space for his thesis that Bitcoin serves as the ultimate store of value and “digital energy.” Under his leadership, his company began aggressively acquiring Bitcoin in August 2020, citing concerns over monetary inflation and the devaluation of fiat currency. In early 2025, the company officially rebranded from MicroStrategy to Strategy Inc. to reflect its dual focus on enterprise analytics and Bitcoin accumulation.
As of December 2025, Strategy Inc. holds over 671,000 BTC, making it the largest corporate holder of Bitcoin in the world. Saylor’s approach involves leveraging capital markets—issuing equity and convertible debt—to purchase Bitcoin, a tactic he describes as “accretive” to shareholders.
Early Life and Education
Born in Lincoln, Nebraska, in 1965, Saylor grew up in a military family and spent his childhood on various U.S. Air Force bases. He attended the Massachusetts Institute of Technology (MIT) on an Air Force ROTC scholarship, graduating in 1987 with dual degrees in Aeronautics and Astronautics, and Science, Technology, and Society.
Although he intended to become a pilot, a medical diagnosis prevented him from flying. He subsequently focused on computer simulation and technology, eventually founding MicroStrategy in 1989 at the age of 24.
Career and MicroStrategy
Saylor took MicroStrategy public in 1998. The company became a leader in the data mining and business intelligence sectors. Saylor garnered significant attention during the dot-com boom, though the company faced severe challenges during the market crash in 2000, including an SEC investigation regarding financial reporting which was settled without admitting wrongdoing.
In August 2020, Saylor initiated the company’s pivot to a Bitcoin standard, converting its cash reserves into BTC. This move revitalized the company's stock (MSTR), transforming it into what many investors view as a leveraged Bitcoin proxy.
In August 2022, Saylor transitioned from CEO to Executive Chairman to focus exclusively on the company’s Bitcoin acquisition strategy and advocacy. In February 2025, the company rebranded to “Strategy” to emphasize its commitment to the digital asset ecosystem.
Philosophy and Advocacy
Saylor is known for his rhetorical style and conviction regarding Bitcoin's role in the future of finance. He argues that Bitcoin is superior to gold, real estate, and equity as a long-term store of value due to its scarcity, portability, and immutability.
- “There is no second best”: A famous catchphrase emphasizing his belief that Bitcoin has no legitimate competitors in the crypto asset class.
- Digital Energy: Saylor frequently uses physics metaphors, describing Bitcoin as a battery that preserves economic energy over time without dissipation (inflation).
- Saylor Academy: A non-profit initiative he founded in 1999 that provides free education to millions of students globally. The academy offers courses on Bitcoin economics and history.
Controversies and Risks
Saylor’s career has not been without controversy. The 2000 dot-com crash resulted in significant personal wealth loss and regulatory scrutiny. More recently, in 2024, Saylor and his company settled a tax fraud lawsuit with the District of Columbia for $40 million. The suit alleged that Saylor had evaded taxes by misrepresenting his residency status over a period of several years.
Critics of his corporate strategy argue that leveraging a publicly traded company to buy volatile assets poses systemic risks to shareholders. However, Saylor maintains that volatility is the price of high performance and that the long-term appreciation of Bitcoin will validate the strategy.
