Michael Saylor: A Zealous Evangelist for Bitcoin

At the intersection of traditional finance and cryptocurrency, Michael Saylor’s name has become a legend. 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 with an almost obsessive belief in Bitcoin, sparking a global discussion on corporate capital allocation and the value of crypto assets.

From software vendor to Bitcoin whale: a disruptive transformation

Michael Saylor’s career began in 1989 when he founded MicroStrategy, a company that initially focused on business intelligence software services but faced long-term competition from giants such as Microsoft and Oracle. In 2020, the global monetary easing policy triggered by the COVID-19 pandemic prompted him to re-examine asset allocation logic. Saylor believes that Bitcoin is the “digital gold,” with its anti-inflation properties and scarcity reshaping the global financial system. In August of the same year, MicroStrategy announced the first purchase of Bitcoin for $250 million, officially embarking on the transformation journey.

Over the next four years, Strategy cumulatively invested over 27.7 billion US dollars through its own funds, issuing convertible bonds, equity financing, and other means, purchasing 555,450 Bitcoins at an average price of 67,373 US dollars (as of May 2025). The total holding value once exceeded 37 billion US dollars, making it the ‘King of Hodlers’ among global listed companies. This aggressive strategy not only caused the company’s stock price to surge by 2,350% in four years but also pushed its market value to surpass 100 billion US dollars in 2025, overtaking tech giants such as NVIDIA and Meta.

“Unlimited Capital Flaws”: The Magic of a Financial Engineering

Saylor’s Bitcoin strategy is not simply asset allocation, but a precise capital game, known to supporters as the “infinite money loophole.” The core logic is to leverage the frenzy of the capital market for Bitcoin, forming a closed loop of “financing - buying coins - price increase - refinancing”.

1. Low-cost financing: attract institutional investors such as hedge funds by issuing convertible bonds with interest rates as low as 0% - 0.75%, and even raise funds through equity issuance (ATM) to avoid traditional debt pressure.
2. Premium arbitrage: Due to the long-term premium of the Strategy stock price over its Bitcoin net asset value (the premium rate once reached 90%), the company can leverage $1 funding to leverage $2 purchasing power of Bitcoin, creating a leverage effect.
3. Market feedback loop: Bitcoin price Rising boosts the company’s stock price, further strengthens its financing capabilities, and forms a self-reinforcing growth flywheel.

This strategy has been particularly effective in bull markets: In 2024, the stock price of Strategy surged by nearly 400% annually, far exceeding Bitcoin’s 122% increase, and is even considered by Wall Street as ‘leveraged Bitcoin call options’.

The game of faith and risk: hidden worries under high leverage

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

• Debt risk: The company has unpaid debts amounting to billions of dollars. If the Bitcoin price remains below $16,364 in the long term (2022 critical point), it may face insolvency risk. However, the current debt-to-equity ratio is only 0.208, much lower than traditional investment banks like Goldman Sachs, and short-term pressure is manageable.
• Market fluctuations: The high volatility of Bitcoin prices directly impacts the stock price of Strategy. In early 2025, Bitcoin once dropped by 25%, leading to a $6 billion loss on the company’s books, highlighting the fragility of the strategy.
• Competition Impact: The launch of Bitcoin spot ETF has diverted some institutional funds, weakening the uniqueness of Strategy as an ‘indirect investment tool’.

In response, Saylor showed extreme firmness, claiming to ‘never sell Bitcoin,’ and predicting that Bitcoin will surpass 1 million US dollars within 10 years. He even renamed the company to Strategy to demonstrate his determination to completely transform into a ‘Bitcoin Treasury Company.’

Revelations Behind the Controversy: A New Paradigm for Cryptocurrency and Corporate Strategy

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

• Asset securitization: The company converts the value of Bitcoin holdings into equity premiums to attract investors seeking exposure to encrypted assets.
• Decentralized narrative: By using metrics such as ‘Bitcoin Yield KPI,’ the enterprise value is directly linked to the crypto market, breaking the traditional valuation framework.
• Regulatory Game: Despite multiple warnings from the SEC in the United States about the speculative risks of Bitcoin, Strategy, as a publicly listed company, provides institutional investors with a compliant channel to participate in the crypto market.

Conclusion: A financial experiment that has not yet ended

Michael Saylor’s Bitcoin gamble with Strategy is not only the ultimate expression of personal belief, but also a high-risk financial innovation. Its success depends on the long-term rise of Bitcoin prices and the sustained frenzy in 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 puts it: ‘This is not just an investment, but an epic about faith and market frenzy.’