Michael Saylor: A Bitcoin Enthusiast Evangelist

At the intersection of traditional finance and cryptocurrency, Michael Saylor’s name has become legendary. As the co-founder and chairman of the business intelligence company MicroStrategy (now renamed Strategy), he transformed a software company on the brink of bankruptcy into the world’s largest Bitcoin holding institution, driven by an almost obsessive belief in Bitcoin, and sparked a global discussion on corporate capital allocation and the value of crypto assets.

From Software Vendor to Bitcoin Whales: A Disruptive Transformation

Michael Saylor’s career began in 1989 with the founding of MicroStrategy, which initially focused on business intelligence software services but faced long-term competitive pressure from giants like Microsoft and Oracle. In 2020, the global monetary easing policies triggered by the COVID-19 pandemic prompted him to reassess asset allocation logic. Saylor believes that Bitcoin is “digital gold,” and its anti-inflation properties and scarcity will reshape the global financial system. In August of the same year, MicroStrategy announced its first purchase of Bitcoin for $250 million, officially starting its transformation journey.

In the following four years, Strategy invested over $27.7 billion through its own funds, issuing convertible bonds, equity financing, and other means, purchasing 555,450 Bitcoins at an average price of $67,373 (as of May 2025), with the total value of holdings once exceeding $37 billion, becoming the “King of Holdings” among listed companies worldwide. This aggressive strategy not only caused the company’s stock price to soar by 2,350% over four years but also allowed its market capitalization to exceed $100 billion in 2025, surpassing tech giants like Nvidia and Meta.

“Infinite Capital Loophole”: A Financial Engineering Magic

Saylor’s Bitcoin strategy is not merely a simple asset allocation, but a sophisticated capital game, referred to by supporters as the “infinite funding loophole.” The core logic is to leverage the capital market’s frenzy for Bitcoin to create a closed loop of “financing - purchasing coins - stock price increase - refinancing:”

1. Low-cost financing: By issuing convertible bonds with interest rates as low as 0% - 0.75%, attracting institutional investors such as hedge funds, and even raising funds through equity issuance (ATM), avoiding traditional debt pressure.
2. Premium Arbitrage: As the price of Strategy has long been above its net asset value of Bitcoin (the premium rate once reached 90%), the company can leverage $1 in financing to gain $2 in Bitcoin purchasing power, creating a leverage effect.
3. Market feedback loop: The rise in Bitcoin prices boosts company stock prices, further strengthening financing capabilities, creating a self-reinforcing growth flywheel.

This strategy performs remarkably well in a bull market: in 2024, the price of Strategy saw an annual increase of nearly 400%, far exceeding Bitcoin’s 122% increase, and was even regarded by Wall Street as “a leveraged Bitcoin call option.”

The Game of Faith and Risk: Hidden Worries Under High Leverage

Despite the significant unrealized gains from Bitcoin holdings of Strategy, Saylor’s aggressive approach has always been accompanied by controversy:

• Debt Risk: The company’s unpaid debts amount to billions of dollars, and it may face insolvency risk if the price of Bitcoin falls below $16,364 (the critical point in 2022) for a prolonged period. However, the current debt-to-equity ratio is only 0.208, which is much lower than traditional investment banks like Goldman Sachs, indicating that short-term pressure is manageable.
• Market Volatility: The high volatility of Bitcoin prices directly affects the stock price of Strategy. At the beginning of 2025, Bitcoin once dropped by 25%, resulting in a paper loss of 6 billion dollars for the company, highlighting the fragility of the strategy.
• Competitive Impact: The launch of the Bitcoin spot ETF has diverted some institutional funds, weakening Strategy’s uniqueness as an “indirect investment tool.”

In this regard, Saylor showed an extremely firm attitude, declaring “never to sell Bitcoin” and predicting that Bitcoin will surpass $1 million within 10 years. He even renamed the company to Strategy to highlight his determination to completely transform it into a “Bitcoin treasury company.”

Insights Behind the Controversy: A New Paradigm of Crypto Assets and Corporate Strategy

The case of Strategy has disrupted the logic of traditional corporate financial management. By deeply binding the balance sheet with Bitcoin, Saylor has created a new model of capital operation:

• Asset Securitization: The company converts the value of its Bitcoin holdings into equity premiums to attract investors seeking exposure to crypto assets.
• Decentralized Narrative: By linking corporate value directly to the crypto market through indicators such as “Bitcoin Yield KPI” and breaking traditional valuation frameworks.
• Regulatory Game: Despite the SEC’s repeated warnings about the speculative risks of Bitcoin, Strategy, with its status as a publicly listed company, provides institutional investors with a compliant way to participate in the crypto market.

Conclusion: A Financial Experiment That Has Not Yet Ended

Michael Saylor’s bet on Bitcoin with Strategy is both an extreme expression of personal belief and a high-risk experiment in financial innovation. Its success relies on the long-term rise in Bitcoin prices and the continued fervor of the capital markets, and any black swan event could disrupt this fragile balance. However, it is undeniable that this experiment has redefined the boundaries of corporate asset allocation and provided a key case for the mainstreaming of crypto assets. As the Financial Times documentary states: “This is not just an investment; it’s an epic tale of faith and market frenzy.”

Author: Blog Team *This content does not constitute any offer, solicitation, or recommendation. You should always seek independent professional advice before making any investment decisions. *Please note that Gate may restrict or prohibit some or all services from restricted areas. Please read the user agreement for more information, link: