Saylor Strategy Bitcoin Bet Hits 2,600% Gain After 5 Years

Saylor’s Strategy started buying Bitcoin 5 years ago. It’s now up 2,600%

Saylor Strategy, formerly MicroStrategy, is celebrating the fifth anniversary of its first Bitcoin purchase. The bold move has driven its share price up nearly 2,600% since 2020, ending a two-decade stagnation.

On Aug. 11, 2020, the company spent $250 million to acquire 21,454 BTC. Founder Michael Saylor called it a “new capital allocation strategy.” Since then, Strategy has invested $46 billion to amass 628,791 BTC — the largest Bitcoin stash held by any public or private company.

These buys have propelled its stock (MSTR) from under $15 in 2020 to over $395 as of last Friday.

Strategy’s accounting scandal in the dot-com era

Founded in 1989, Strategy built its name selling business analytics software. It thrived during the 1990s dot-com boom, debuting on Nasdaq in 1998 and hitting a share price of $313 in March 2000.

That same month, the company admitted to overstating revenue for 1998 and 1999. The stock plunged more than 60% in a single day. The SEC charged Strategy, Saylor, and other executives with fraud. They settled without admitting wrongdoing but paid millions in fines.

The fallout left Strategy’s shares languishing for the next 20 years.

Bitcoin transformed Strategy’s stock performance

After years of trading between $10 and $20, Strategy’s fortunes shifted in 2020. Bitcoin purchases pushed the stock over $70 within a year, mirroring BTC’s surge from $11,500 to $50,000.

The company’s share price now tracks Bitcoin’s movements. It took 24 years to surpass its March 2000 high, finally breaking it in November 2024 when MSTR closed at $340 — the same day Bitcoin crossed $80,000.

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What’s next for Strategy and Bitcoin?

In May, Saylor revealed plans to raise $84 billion over two years to continue buying Bitcoin. Strategy uses share sales and convertible debt to fund these purchases.

Its unrealized Bitcoin profit stands near $28.8 billion, according to StrategyTracker. The company has disclosed it may sell BTC to manage debt, though recent posts from Saylor suggest more buying is likely.

On July 29, Strategy acquired another 21,021 BTC. Saylor hinted at further purchases in an X post on Sunday, stating, “If you don’t stop buying Bitcoin, you won’t stop making money.”