Michael Saylor, co-founder and Executive Chairman of MicroStrategy, has become one of the most vocal and high-profile Bitcoin evangelists in the world. But before he was known as the “Bitcoin Billionaire,” Saylor was already a tech entrepreneur with a storied career—filled with both meteoric highs and near-fatal lows.
So how did he get rich? And what exactly is his Bitcoin strategy that has Wall Street and crypto Twitter buzzing?
The Rise of Michael Saylor
Michael Saylor made his first fortune in the 1990s. He co-founded MicroStrategy in 1989, a business intelligence company that provided data analytics software to large corporations. In the early days of the dot-com boom, MicroStrategy went public and saw its stock price skyrocket. Saylor’s net worth reportedly reached over $7 billion during this time.
But the good times didn’t last.
In 2000, the SEC charged MicroStrategy with accounting irregularities. The stock plummeted, and Saylor lost billions almost overnight. While the company survived, his personal wealth took a massive hit. He spent the next two decades rebuilding—not through flashy startups or headline-making ventures, but by quietly running and growing MicroStrategy.
Then, in 2020, everything changed.
Enter: Bitcoin
In August 2020, amid growing concerns about inflation and the declining purchasing power of the U.S. dollar, Saylor made a radical move: MicroStrategy used its corporate treasury to buy $250 million worth of Bitcoin. At the time, many on Wall Street called it reckless. But Saylor wasn’t done.
He doubled down—again and again.
Over the next few years, MicroStrategy accumulated over 200,000 BTC (as of 2024), spending billions. Saylor also personally bought hundreds of millions of dollars worth of Bitcoin for himself.
So, what’s the strategy behind this bold move?
Saylor’s Bitcoin Strategy Explained
1. Bitcoin as Digital Property
Saylor doesn’t view Bitcoin as a currency or a short-term investment. He calls it “digital property”—a superior version of gold. In his view, Bitcoin is the scarcest, most secure, and most desirable store of value ever created.
2. Inflation Hedge
Saylor believes fiat currencies are being debased at an accelerating rate. By holding cash, companies are essentially watching their purchasing power erode. Bitcoin, with its fixed supply of 21 million coins, offers a hedge against inflation and monetary debasement.
3. Leveraging the Balance Sheet
One of the most controversial aspects of Saylor’s strategy is using debt to buy more Bitcoin. MicroStrategy has issued convertible bonds and taken on loans to fund BTC purchases. His reasoning? If the interest rates on debt are lower than Bitcoin’s potential returns, it’s a net win. High risk, high reward.
4. Time Horizon: Forever
Saylor isn’t playing for the next bull cycle. His timeline is generational. He frequently says Bitcoin is something to buy and never sell. This long-term conviction is a key part of his strategy—and why he’s willing to stomach volatility that would spook traditional investors.
The result?
Saylor has turned MicroStrategy into a “Bitcoin holding company” in the eyes of many investors. The stock often trades in tandem with BTC price action. And Saylor himself has re-entered the billionaire ranks—thanks largely to his crypto holdings.
More importantly, he’s become a symbol of institutional Bitcoin adoption. Love him or hate him, Saylor’s commitment is unwavering. His bold bet has inspired other companies and investors to reconsider what it means to hold cash—and what the future of money could look like.
In short, Michael Saylor got rich by building a tech company, lost it in a crash, rebuilt it, and then bet big—very big—on Bitcoin. His strategy is simple but aggressive: Buy Bitcoin. Hold it forever. And use every tool possible—cash flow, equity, and debt—to acquire more.
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