The Math That Makes MicroStrategy Beat Bitcoin

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Grab a coffee, settle in, and think beyond the daily price swings of Bitcoin. What if the story isn’t about timing the market, but about how a company’s structure quietly compounds value over the years? That’s the argument Strive CIO Jeff Walton is making about MicroStrategy (MSTR), a stock that, on the surface, moves with crypto, but underneath, he says, operates like a machine steadily increasing Bitcoin exposure per share.

Crypto News of the Day: Strive CIO Jeff Walton on Why Buying MSTR at 2.5x mNAV Still Beats Spot Bitcoin

Jeff Walton, Chief Risk Officer at Strive and founder and CEO of its subsidiary True North, says most investors fundamentally misunderstand MicroStrategy (MSTR).

Reflecting on his own 2021 purchases, Walton argues the stock should not be viewed as a leveraged Bitcoin proxy. Rather, investors should view MSTR as a capital markets engine designed to increase Bitcoin exposure per share over time.

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Walton revealed he began buying MSTR in June 2021 at roughly 2.5x mNAV, believing the stock was already down 50%.

By late 2022, the company was trading near 1.3x mNAV, holding 129,999 Bitcoin while its notional debt briefly exceeded asset value. Despite being “down bad on paper,” Walton said the underlying math never broke.

By mid-2023, Walton said he went “all in,” convinced the capital structure, not price action, was the real thesis.

That conviction, he argues, is what allowed long-term holders to survive one of the harshest drawdowns in crypto equity history.

How Time and Structure Changed the Risk Equation for MicroStrategy

Fast forward to late 2025, Walton notes that MicroStrategy now holds 672,497 Bitcoin. Notably, this is more than 12 times the size of the next-largest publicly traded corporate holder.

More importantly, he says, the risk profile of his original shares has undergone a fundamental change.

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In his view, capital market activity steadily de-risked common equity while amplifying Bitcoin exposure per share.

From this point forward, Walton argues his 2021 shares can structurally outperform Bitcoin even if the company acquires zero additional BTC.

That framing drew support from market commentators, who argued investors were buying a system, not leverage.

In Walton’s view, volatility itself became an input, effectively serving as fuel for accretion rather than a threat to the thesis.

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But Is It A Structural Edge or a Cycle-Dependent Trade?

Strive CEO Matt Cole has echoed Walton’s view, recently stating that MSTR has outperformed Bitcoin and gold over five years. According to Cole, this could remain true even at $75,000 BTC or 1x mNAV.

However, not everyone agrees that the structural edge is guaranteed going forward. Contrarian narratives argue that while five-year outperformance was real through mid-2025, MSTR materially underperformed Bitcoin during the second-half drawdown. Further, it has traded near or below 1x mNAV in recent weeks.

Elsewhere, Barchart indicates that MicroStrategy was the worst-performing Nasdaq-100 stock of 2025, down roughly 65% from its peak amid a broader crypto winter.

Critics like Peter Schiff dismissed the strategy entirely, arguing that Strategy’s average Bitcoin cost implies modest annual returns.

Others warned that sustained sub-1x mNAV conditions could theoretically prompt Bitcoin sales, a scenario CEO Phong Le has acknowledged would make “mathematical” sense, although management has stressed that it is unlikely.

Still, signs of institutional interest persist. According to industry commentary, large US banks are now exploring partnerships with Strategy, with Michael Saylor framing bank adoption, not price, as the defining Bitcoin narrative for 2026.

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Will MSTR’s structure prove cycle-proof? Walton argues that time and capital structure do the real work, not timing.

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