Five years ago, MicroStrategy $MSTR shares were trading around $61.80 each. Today, January 23, 2026, it's closed at $163.11—a solid 164% gain that largely tracks its bold strategy of holding massive amounts of Bitcoin as a treasury asset, turning the company into a leveraged play on crypto prices. The chart shows sharp swings: a huge run-up in 2024-2025 as Bitcoin surged, followed by pullbacks in late 2025, with after-hours steady at $163.11.

That 52-week high of $457.22 (reached during the peak Bitcoin rally) stands as proof of the explosive upside when crypto momentum aligns. In plain terms, the compound annual growth rate (CAGR) over the past five years is 21.43%. That's the average yearly increase—calculated by raising the total growth factor to the 1/5 power and subtracting 1. It means growing your money by about 21% each year, on average.

Dollar-cost averaging (DCA) handles the volatility well: Invest $500 every month for five years, totaling $30,000. You buy more shares during pullbacks and fewer during spikes, which smooths out the wild rides tied to Bitcoin's price.

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Projecting forward at the same historical pace, with a monthly growth rate of about 1.63% from $163.11, your shares accumulate steadily. After 60 months, your portfolio could reach $49,998. That's a gain of $19,998—a 67% return on your investment. The early buys get the full benefit of compounding, while later ones still participate in any sustained uptrend.

This projection follows past performance, which is no guarantee of future results—MicroStrategy is essentially a Bitcoin proxy, so its stock price moves sharply with crypto markets, regulatory news, or shifts in Bitcoin sentiment. A P/E ratio of 7.58 reflects low earnings relative to price (typical for a holding-company structure focused on asset appreciation), and there is no dividend. With that 52-week high of $457.22 as a recent peak and a $47.76B market cap, the upside is tied to Bitcoin's trajectory.

If DCA suits your long-term view and tolerance for volatility, it could turn your $500 habit into a meaningful position by 2031. Stay the course?