Michael Saylor’s $18M Bitcoin Bet: 5 Years of Unshakable HODLing Pays Off

MicroStrategy's Bitcoin gambit hits a milestone—proving Wall Street's goldbugs wrong one satoshi at a time.

The original $18 million purchase now stands as a masterclass in conviction investing—while traditional finance still struggles to spell 'blockchain'.

Five years later, Saylor's playbook remains unchanged: accumulate, hold, and let the skeptics seethe.

(Bonus jab: Meanwhile, your bank's 'innovative' 0.01% APY savings account just got a 2-cent monthly bonus.)

Strategy’s Bold Moves Keep the Momentum Going

Even in a year of record-breaking purchases, this latest buy is one of Strategy’s smallest. Earlier this year, the smallest was 130 BTC for $10.7 million. On the other end of the spectrum, just last week the firm scooped up 21,021 BTC for $2.46 billion. These moves show a clear pattern—whether the buy is big or small, Strategy is always adding to its bitcoin position.

Saylor had hinted at this latest purchase in an X post, fueling speculation before the official announcement. He remains one of Bitcoin’s loudest corporate advocates, often linking BTC ownership to long-term wealth creation. The company has even filed a $4.2 billion stock offering, with the goal of using the proceeds to buy more Bitcoin. This aggressive stance sets Strategy apart from traditional public companies.

Bitcoin Price Surge Boosts Strategy’s Profile

The timing of this purchase is no accident. Bitcoin has been testing new highs, breaking above $122,000 in recent trading. This surge has also lifted Strategy’s stock (MSTR), which is now up around 31% year-to-date. In fact, MSTR has outperformed BTC in 2025 so far. The stock recently bounced from $395 to about $406 on the news of the latest buy.

The close correlation between BTC price moves and MSTR performance is no surprise. Strategy’s balance sheet is so heavily weighted toward Bitcoin that its stock reacts directly to market swings. As BTC climbs, Strategy’s position—and its market value—grow stronger.

Saylor’s Vision Shapes Long-Term Strategy

Michael Saylor is playing the long game. He has pledged to keep buying Bitcoin regardless of price, predicting that BTC could reach $21 million over the next 21 years. While that forecast is bold, his track record makes it hard to ignore. Since the first purchase in 2020, the strategy has brought massive returns and put the company in the spotlight as the largest public Bitcoin holder.

The numbers speak for themselves—74 separate BTC buys over five years, with no signs of slowing down. For Saylor, Bitcoin is more than just an asset; it’s the core of the company’s financial identity. His consistent execution has turned Strategy into a benchmark for corporate crypto adoption.

The Future of Strategy and Bitcoin

Looking ahead, Strategy’s playbook seems set. Keep raising capital, keep buying BTC, and keep holding for the long term. This approach has already reshaped how investors view corporate treasury management. In a market where most firms still shy away from large-scale crypto exposure, Strategy stands alone.

If Bitcoin continues its climb, the rewards could be historic. But even if volatility strikes, Saylor’s unwavering stance suggests the company won’t back down. For both BTC believers and market watchers, Strategy remains one of the most important players in the global crypto game.