Who is Michael Saylor? The legendary guru with a $9 billion fortune betting on Bitcoin.

Michael J. Saylor is a renowned entrepreneur, corporate executive, and Bitcoin advocate, co-founder and executive chairman of Strategy. After purchasing $250 million worth of Bitcoin in August 2020, he led the company to become the largest Bitcoin holding institution in the world. As of the third quarter of 2025, Strategy holds over 600,000 BTC.

From MIT Genius to the Early Journey of Internet Bubble Collapse

Michael Saylor was born in 1965 in Nebraska, USA, and grew up in an Air Force officer family, moving with his parents between various military bases during his childhood, leading to a disciplined lifestyle. This military family background cultivated his execution ability and discipline, qualities that played a crucial role in his future entrepreneurship and Bitcoin investments.

He was admitted to the Massachusetts Institute of Technology (MIT), majoring in Aerospace Engineering and Scientific Engineering, and was one of the top-performing students at the time, graduating with the highest honors from MIT. The engineering training at MIT provided him with rigorous logical thinking and systematic analysis skills, enabling him to understand the revolutionary nature of Bitcoin from a mathematical and technical perspective. In 1989, he co-founded Strategy (formerly MicroStrategy) with partners, focusing on the development of enterprise data analytics and business intelligence (BI) systems, at a time when large-scale data management and reporting tools were rapidly emerging.

In the late 1990s, driven by the internet technology stock bubble, the share price of Strategy skyrocketed, and Saylor's personal net worth reached its peak in 1999, surpassing 7 billion USD and making it onto the Forbes billionaire list. However, the good times did not last long; in 2000, the internet bubble burst, and Strategy was investigated by the US SEC (Securities and Exchange Commission) due to financial reporting errors, leading to a dramatic drop in the company's stock price by 90% in a short period, causing Saylor's personal wealth to nearly vanish.

Despite the widespread skepticism from the outside, he did not resign but chose to stay, restructuring the company's governance framework and transforming Strategy into a niche enterprise software company focused on serving specific industries, gradually restoring operational stability. This process of falling from a peak to a trough and then slowly climbing back up has given him a profound understanding of the capital markets, risk management, and corporate financial structures, laying the foundation for his “non-speculative” perspective when entering the Bitcoin world.

2020 Transformation: From Tech CEO to Bitcoin Evangelist

In 2020, during the pandemic, global central banks printed money to rescue the markets, and Saylor's doubts about the fiat currency system reached a peak. At that time, Strategy had over 500 million dollars in cash positions, facing the risks of the Federal Reserve's ultra-loose policies and the rapid devaluation of fiat currency. Saylor believed that the purchasing power of the dollar was being systematically eroded, and traditional cash reserves and short-term government bonds could no longer provide effective hedging.

He made an unprecedented decision: to convert cash assets into Bitcoin as a reserve asset for the company. In August 2020, Strategy purchased its first Bitcoin worth 250 million dollars. Saylor defended this investment, stating that Bitcoin is not just another digital trend, but also “digital gold,” which can protect wealth from inflation and provide long-term value.

Since that year, he transformed a solid tech company into one of the largest Bitcoin holders in the world; he himself went from being an outsider on Wall Street to becoming a spiritual leader in the crypto space. Over the past 5 years, through persistent purchases of Bitcoin, Strategy has accumulated over 600,000 Bitcoins, and the company's stock price has grown more than 20 times. As of November 2024, Strategy holds 331,200 Bitcoins, valued at over 32.5 billion USD, acquired at approximately 16.5 billion USD, with an average cost per BTC of nearly 50,000 USD.

**Strategy of Leveraging to Purchase Bitcoin: **

End of 2020: Raised 650 million USD, all used to purchase Bitcoin

2021: Issued $500 million in secured notes to continue buying coins.

October 2024: Announce plans to raise $42 billion over the next three years to purchase more Bitcoin.

November 2024: $3 billion raised through priority convertible bonds, with a maturity date in 2029.

The real difference between Strategy and other companies involved in Bitcoin lies in its bold strategy of purchasing BTC through debt. The company raised billions of dollars by selling convertible corporate bonds, which are essentially promissory notes that investors can later exchange for cash, Strategy stock (MSTR), or a mix of both. Many consider this strategy to be quite risky, but Saylor believes it is worthwhile, as Bitcoin is the “most scarce asset” in the world. He likens it to owning “digital real estate,” emphasizing its ability to hedge against inflation.

Michael Saylor's Bitcoin Faith Core

In a ten-thousand-word interview with CoinDesk in 2025, Saylor clearly expressed his faith in Bitcoin. He does not see it as a technological tool, but rather as “the economic immortality mechanism created by Satoshi Nakamoto.” He often refers to Bitcoin as “the highest property of humanity,” superior to gold or any other traditional store of value. According to him, Bitcoin is the safest and most portable asset you can own, as it has the ability to withstand inflation and government intervention.

Saylor's core viewpoints can be summarized in three aspects. The first is Bitcoin's positioning as digital gold: scarcity (with a limit of 21 million coins), decentralization (no central issuer), and censorship resistance, positioning it as the next generation form of global value storage in comparison to gold. The second is the judgment that fiat currency will eventually depreciate: central banks around the world have been continuously expanding the money supply through loose monetary policies (such as quantitative easing QE) for many years, leading to a long-term weakening of the purchasing power of currency. Saylor believes that cash is not an asset, but rather a type of “liability that will continuously lose value.”

The third is the investment philosophy of long-termism against short-term volatility: “Don't try to time the market, focus on holding time.” For Bitcoin, four years is a cycle, ten years is a revolution. He even proposed a highly controversial view: “Permanently destroying private keys is the ultimate form of decentralized charity.” He believes that individuals can choose to “return wealth to the Bitcoin network” after their death, creating a depersonalized, sustainable capital donation. In January 2025, during an interview with Fox Business, Saylor announced that he would destroy all Bitcoin private keys after his death.

This concept, which blends mathematics, faith, economics, and philosophy, has made him a highly controversial and influential figure both within and outside the coin circle. Saylor's Bitcoin actions are not asset allocations on financial statements, but rather a wealth revolution built on philosophy and belief. For him, Strategy is a “Bitcoin Operating Company,” turning Bitcoin into the main entity on the balance sheet, leveraging the power of shareholders and creditors.

90 billion USD wealth and market influence

According to Forbes estimates, as of August 2025, Michael Saylor's personal wealth is approximately $9 billion, ranking 362nd on the Forbes wealth list. His financial status is primarily composed of “Strategy Holdings” and “personally held Bitcoin,” which have a very strong correlation with Bitcoin's price performance. Strategy Holdings consists of approximately 20,000,000 shares, valued at about $6.88 billion based on a share price of $344, and he personally holds 17,732 Bitcoins (as per public data from 2020), valued at approximately $2.04 billion based on $115,000 per Bitcoin, totaling about $8.92 billion.

Saylor's candid advocacy has sparked a chain reaction throughout the corporate world. By demonstrating the feasibility of holding Bitcoin as a treasury reserve, he has inspired other companies to explore cryptocurrency investments. Tesla, Square, and other companies have also followed a similar path, providing feasibility for Bitcoin as an institutional asset. The large-scale acquisitions by Strategy have also influenced the market price of Bitcoin, as the company's purchase volumes are typically substantial, sometimes leading to price surges and increases in market activity.

It is worth noting that Strategy's active purchase of Bitcoin has been one of the driving forces behind MSTR stock rising over 450% in 2024. This astonishing stock performance has transformed Strategy from a traditional tech company into a star player in the crypto market, attracting a significant amount of speculative capital and institutional investors. However, this also means that Strategy's financial health is closely tied to Bitcoin's price fluctuations, and when Bitcoin's price falls, some are concerned that the company's loans may face the risk of “margin calls.”