Ten years ago, Strategy was a mid-size business intelligence software company trading at around $18 a share. No Bitcoin. No Michael Saylor on television. No meme stock following. Just a quiet
Ten years ago, Strategy was a mid-size business intelligence software company trading at around $18 a share.
No Bitcoin. No Michael Saylor on television. No meme stock following. Just a quietly struggling enterprise software firm that most retail investors had never heard of.
A $1,000 investment in July 2015 would have bought roughly 55 shares at the split-adjusted price. Today, with MSTR trading around $100, that position is worth approximately $5,600, a 10-year total return of 467%.
Solid. Not spectacular. Until you factor in what that same investment was worth at its peak.
Related: Billionaire who received Trump's pardon predicts Bitcoin to $1 million
Everything changed in August 2020, when Michael Saylor made the call that turned a forgotten software stock into a proxy for Bitcoin. He put $250 million of company cash into Bitcoin, the first major corporate treasury to do so, and then kept going. By late 2024, Strategy had accumulated hundreds of thousands of Bitcoin and the stock had gone parabolic.
The all-time high closing price for MSTR was $473.83 on November 20, 2024. Those same 55 shares bought in 2015 for $1,000 were worth approximately $26,480 at that peak, a return of over 2,500%.
The descent since that peak has been steep. MSTR is down 71.72% over the past 12 months. Strategy now sits on 843,775 Bitcoin, with a digital asset carrying value of $49.67 billion as of June 30, 2026.
But with Bitcoin trading near $60,000 against an average purchase price of around $75,000 per coin, the paper losses run deep.
Trending on TheStreet RoundtableStrategy has also been selling Bitcoin to fund operations, most recently offloading 3,588 BTC for approximately $216 million, a stark departure from Saylor's original never sell pledge.
The $1,000 from 2015 is still worth $5,600 today. That is a decent decade.
But it required holding through an 80% drawdown from the all-time high, watching the company sell Bitcoin it promised to never sell, and trusting that the thesis still holds.
For the people who got out near $473, the story looks very different. For everyone else, the next move in Bitcoin decides what that $1,000 is ultimately worth.
