Strive CIO Discusses How MicroStrategy’s Structure Allows Its Stock to Outperform Bitcoin

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Get ready to look beyond Bitcoin’s daily price fluctuations. What if the narrative revolves around a company's structure that steadily boosts its value over time? This is the point Strive Chief Investment Officer Jeff Walton brings forward regarding MicroStrategy (MSTR), a stock that seems to follow crypto trends but, according to Walton, functions like a well-oiled machine that progressively increases Bitcoin exposure per share.

Insights from Jeff Walton on MicroStrategy (MSTR) and Bitcoin

Jeff Walton, who is the Chief Risk Officer at Strive and the founder as well as CEO of its subsidiary True North, believes many investors misunderstand MicroStrategy (MSTR). He reflects on his investments from 2021, arguing that MSTR should not just be viewed as a leveraged Bitcoin proxy. Instead, he suggests it be seen as a capital markets engine aimed at enhancing Bitcoin exposure per share over time.

Walton mentioned that he began acquiring MSTR shares in June 2021 at about 2.5 times market Net Asset Value (mNAV), convinced the stock was already down by 50%. Little did he realize the stock would drop an additional 80% from his purchase price, with MSTR plummeting nearly 90% from its peak in February 2021. By late 2022, the company was trading at about 1.3x mNAV, holding 129,999 Bitcoin, and its debt briefly exceeded its asset value. Despite being “down bad on paper,” Walton maintained that the fundamental numbers remained strong.

He stated, “The company had REAL hard money, and the debt covenants were not extreme," while highlighting several bullish indicators on the horizon for crypto, such as the halving cycle and ETF developments. By mid-2023, Walton went “all in,” convinced that MicroStrategy’s capital structure, rather than fluctuating prices, represented the core investment thesis. He argues that this conviction enabled long-term holders to withstand one of the worst downturns in crypto equity history.

How MicroStrategy Has Altered Its Risk Profile Over Time

Looking ahead to late 2025, Walton notes that MicroStrategy currently holds 672,497 Bitcoin, which is over 12 times more than the next-largest publicly traded corporate holder.

Top 100 Public BTC Treasury Companies. Source: Bitcoin Treasuries

More significantly, Walton points out that the risk profile of his initial shares has fundamentally shifted. The price per share now stands at 160% higher than the 2.5x mNAV shares he bought in June 2021. He believes the continued capital market activity has gradually reduced the risk for common equity while enhancing Bitcoin exposure per share.

Moving forward, Walton asserts that his 2021 shares can structurally outperform Bitcoin, even if no further Bitcoin is acquired by the company. He emphasizes, “There is materially more Bitcoin exposure in EACH share I purchased in 2021 than when I bought them,” noting that additional Bitcoin exposure has come from dilution, preferred equity, and long-term debt rather than just price increases. This perspective garnered backing from market analysts who suggested that investors are buying a complete system rather than mere leverage.

“Bitcoin is a bearer asset, while MicroStrategy serves as an operating system to acquire Bitcoin using public market incentives,” one analyst remarked. In Walton’s opinion, volatility itself became a catalyst for growth, acting as a support mechanism rather than a threat to the investment thesis.

Assessing MicroStrategy's Future: Structural Advantage or Cyclical Trade?

Strive CEO Matt Cole has echoed Walton’s sentiments, claiming that MSTR has outperformed both Bitcoin and gold over the past five years. He asserts this trend could persist even with Bitcoin priced at $75,000 or at 1x mNAV.

“The two crucial terms in investing are 'Total Return,' not 'Average Cost.' $MSTR has outshined BTC and Gold in the last five years, and this will remain true at $75,000 BTC or at a 1x mNAV,” he emphasized.

However, there are dissenting opinions about whether this structural advantage will continue. Critics suggest that while the outperformance over five years was genuine by mid-2025, MSTR significantly lagged behind Bitcoin during the second half of that year. Moreover, it has recently traded near or below 1x mNAV.

Recent reports from Barchart indicate that MicroStrategy was the weakest performer among Nasdaq-100 stocks in 2025, having experienced a decline of about 65% from its highest point amidst a broader crypto market downturn. Critics like Peter Schiff have dismissed the strategy, arguing that MicroStrategy’s average Bitcoin acquisition cost implies only modest annual returns. Some have also cautioned that persistent sub-1x mNAV conditions could eventually necessitate Bitcoin sales, a situation CEO Phong Le acknowledged could make "mathematical" sense, though management has assured that it is unlikely.

Despite the skepticism, ongoing signs of institutional interest remain. Industry discussions suggest that major U.S. banks are exploring partnerships with MicroStrategy, with Michael Saylor framing bank adoption, rather than price movements, as the defining Bitcoin narrative for 2026.

The same Wall Street that coordinated attacks on $MSTR now wants a seat at the table. Major banks are starting to accept Bitcoin as part of their strategy for 2026.

Will MicroStrategy's structural setup prove resilient across different market cycles? Walton argues that time and a solid capital structure are the real game-changers, not just market timing.

Performance Comparison

Strategy Stock MSTR vs BTC Year-to-Date Performance. Source: Bitcoin Treasuries

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