Despite a 12% Stock Market Drop, Strategy Explodes Michael Saylor's Fortune

Is crypto a scam or a fortune factory? The question keeps coming back, fueled by the market’s roller coaster. Sometimes it strips small investors, sometimes it turns daring gamblers into millionaires. But one constant remains: the big names in the sector keep stacking up profits. Whether it’s Binance’s CZ, Sam Bankman-Fried before his fall, or Michael Saylor with Strategy, history proves that massive accumulation of bitcoins and altcoins eventually pays off, at least for those who know how to wait.

Michael Saylor, from the 2000 crash to a billionaire comeback

Twenty years ago, Michael Saylor was already among the tech giants. Co-founder of Strategy (formerly MicroStrategy), he had amassed more than $7 billion thanks to the Internet bubble. But his glory was brief: a dispute with the SEC forced him to revise his accounts and his empire collapsed. The man could have vanished from the radar; instead, he chose to reinvent himself.

In 2020, he turned Strategy into a bitcoin treasury, initially investing $250 million in the asset. Five years later, the company holds 659,739 BTC, or more than 3.4% of the global supply. These reserves are worth about $73 billion, making Strategy the largest publicly listed company holding bitcoins.

This bold bet pushed Saylor back up in the global rankings. In early September, Bloomberg revealed his entry into the Billionaires Index, with a fortune of $7.37 billion. Like a spectacular return to the circle of the powerful, two decades after his first vanished fortune.

Wealth fueled by bitcoin and Strategy shares

Michael Saylor’s fortune is not diversified. It is almost entirely tied to bitcoin and Strategy. According to Bloomberg, he owns about 8% of the company’s capital through 19.6 million B shares and 382,000 A shares. This represents $6.72 billion, plus $650 million in cash from stock sales.

This dependency makes Saylor a fragile billionaire. When bitcoin soars, he earns billions. When it falls, he loses just as much. In recent months, Strategy’s stock rose 12% since January but fell 12.4% over the last 30 days. This did not stop Bloomberg from including Saylor in its ranking, while excluding his personal 17,732 BTC holdings, as their ownership could not be verified.

Shirish Jajodia, Strategy’s treasurer, recalled that their massive BTC purchases do not disrupt the market:  

The way we buy bitcoin is that we don’t move its price.

Michael Saylor and his “Bitcoin standard” gospel

For Michael Saylor, bitcoin is not just a speculative asset. He makes it a societal project. At the BTC Prague 2025 conference, he sent a message that made waves: 

Anyone who invests in bitcoin today will be incredibly wealthy in the future.

His goal is clear: to impose what he calls the “Bitcoin standard,” a new global financial architecture. According to him, traditional currencies are doomed. The dollar, boosted by favorable laws like the Genius Act signed in July 2025, and bitcoin would form the backbone of the future system.

Key figures marking the trajectory

• Current fortune: $7.37 billion, +15.8% since January;
• Strategy reserves: 659,739 BTC, or $73 billion;
• Cumulative investments: $47 billion in bitcoin since 2020;
• Bloomberg ranking: 491st place on the Billionaires Index.

As a tireless missionary, Saylor continues to multiply conferences, tweets, and BTC purchases. For his supporters, he is the visionary leading finance towards the future. For his detractors, a casino player with billions in digital tokens.

Michael Saylor’s glory, very real today, still finds its limit in the shadow of bitcoin’s creator. Satoshi Nakamoto, the supposed holder of over one million BTC, would possess more than $130 billion if his keys were still active. An extraordinary fortune attributed to a phantom being whom some even suspect to be an artificial intelligence. A reminder that, despite current fortunes, the true master of the game remains invisible.