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

Strategy has just marked five years since its first ever Bitcoin purchase, a starting move that’s helped its share price surge nearly 2,600% since 2020 and revive it from a 20-year lull.

MicroStrategy Inc., which now does business as Strategy, bought its first batch of Bitcoin (BTC) on Aug. 11, 2020, spending $250 million to scoop up 21,454 BTC in what founder Michael Saylor called its “new capital allocation strategy.”

The company has since spent a total of $46 billion buying 628,791 BTC, the largest Bitcoin holdings among any public or private company, and has inspired countless firms to copy its Bitcoin buys.

Those buys have propelled MicroStrategy, Inc. (MSTR) shares to gain over 2,595% over the last five years, having closed trading on Friday at over $395 compared to under $15 it was trading at half a decade ago.

Today marks 5 years since we adopted a $BTC strategy. pic.twitter.com/wZa1NJGeS1

— Strategy (@Strategy) August 10, 2025

Strategy suffered an accounting scandal

Saylor founded Strategy in 1989 and the company — still to this day — sells business analytics software and consulting services.

The firm was a darling of the mid-1990s dot-com bubble, where businesses related to the then-new and widely adopted World Wide Web exploded in value, and it debuted on the Nasdaq in mid-1998.

Strategy’s stock climbed over the next few years and shot to a closing high of $313 in early March 2000, which would remain its peak price for 24 years as later that month, Strategy admitted that a review of its accounting practices found it had overstated its revenues for 1998 and 1999.

Its share price fell by over 60% in a day with the announcement and led to a slew of lawsuits, which many consider a pivotal event in bursting the dot-com bubble.

The Securities and Exchange Commission charged Strategy, Saylor and other executives with fraud and they later settled without admitting wrongdoing and paid millions in fines.

Bitcoin revived Strategy shares from 20 year flatline

Strategy’s share price didn’t recover after the accounting saga, and briefly went as low as under 50 cents, but mainly floated around $10 and $20 for the next twenty years.

That was until it started buying Bitcoin — which helped its share price more than quadruple in the 12 months after its first purchase to over $70 for the first time in 20 years, as the cryptocurrency went from around $11,500 to $50,000 in the same period.

Strategy’s vast Bitcoin holdings mean its share price largely follows the ups and downs of the cryptocurrency, and it took 24 years for the company’s stock to beat its March 2000 peak, after MSTR closed trading on Nov. 11, 2024, at $340 — the same day Bitcoin crossed $80,000 for the first time.

What’s next for Strategy and Bitcoin?

Saylor said in May that Strategy will look to raise $84 billion over the next two years, mostly to continue buying Bitcoin, which doubled a previously announced plan to raise $21 billion.

The company uses a variety of ways to raise capital, such as convertible debt notes and share sales, to fuel its Bitcoin buys.

Related: Michael Saylor is not sweating the rise of Ethereum treasury companies

It’s currently sitting on an unrealized profit of around $28.8 billion on its Bitcoin investments, according to data from StrategyTracker. Strategy has said in regulatory disclosures that it could sell its holdings to pay off billions of dollars of debt.

On Sunday, Saylor posted to X a chart showing Strategy’s past Bitcoin buys, adding, “If you don’t stop buying Bitcoin, you won’t stop making Money.”

Similar posts have preceded Strategy announcing further Bitcoin purchases. The company last bought Bitcoin on July 29, scooping up 21,021 BTC.

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