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Reading: The End of the ‘Never Sell’ Era: Michael Saylor’s Bitcoin Gamble Faces Reality
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News

The End of the ‘Never Sell’ Era: Michael Saylor’s Bitcoin Gamble Faces Reality

News Desk
Last updated: June 29, 2026 10:10 pm
News Desk
Published: June 29, 2026
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Bitcoin has undergone a notable transformation over the past decade, transitioning from a niche digital asset to a mainstream investment, largely due to the influence of Michael Saylor. He revamped his company, Strategy, previously known as MicroStrategy, into what he referred to as a “bitcoin treasury company.” This innovative approach laid the groundwork for many others to follow.

During the peak of Bitcoin’s surge to over $126,000 last year, Saylor’s model appeared to be invincible. However, the recent decline of Bitcoin to approximately $60,141 has led to Strategy’s stock plummeting by around 82% from its peak, illustrating that leverage can have adverse effects in a bear market.

Saylor’s strategy was straightforward: raise capital via stock offerings, convertible debt, and later, perpetual preferred stock, to purchase more Bitcoin. This approach promised amplified shareholder returns as long as Bitcoin’s appreciation outpaced the company’s capital costs. The model gained momentum and was emulated by various firms, including those focusing on Ethereum and Solana.

Now, however, the bullish outlook is fading. Bitcoin has faced substantial declines over the last eight months, recently trading near $58,000, marking a 52% drop from its peak. In stark contrast, the S&P 500 has seen an approximate 72% gain during the same timeframe. Strategy’s dire situation was highlighted by its shares closing around $82, down 82% from highs.

More crucially, a shift in what is termed enterprise mNAV has raised alarms. While some investors monitor market mNAV—comparing the market value of a company to its Bitcoin holdings— the more significant enterprise mNAV takes into account total debt and perpetual preferred stock, subtracting cash reserves. Last week marked the first time enterprise mNAV closed below 1.0, finishing at 0.99. This metric reveals the overall economic burden of Strategy’s capital structure, as debt and preferred stock have increased since 2024, creating obligations that common shareholders must ultimately shoulder.

This decline beneath 1.0 does not preclude Strategy from issuing additional shares; however, it complicates the appeal of doing so, particularly since recent Bitcoin purchases have faced criticism for diluting existing shareholders’ stakes. Furthermore, the ability to accrue additional debt becomes restricted as the company’s leverage increases and investor confidence wanes.

In a significant philosophical shift, Saylor, who once stated that Strategy would “never sell” its Bitcoin, recently sold some of its holdings for the first time. This departure from a steadfast approach indicates an acknowledgment of market realities; no strategy is infallible.

Current analysts have begun predicting Bitcoin could drop to around $50,000, with some bearish outlooks estimating prices could plunge as low as $20,000 amid intensified selling pressure. Should these scenarios unfold, Strategy might have no alternative but to liquidate larger portions of its Bitcoin holdings to meet financial obligations or bolster its balance sheet.

As the company’s debt continues to rise and capital markets tighten, strategic flexibility diminishes. Saylor’s initial vision of a robust treasury model is now under scrutiny as enterprise mNAV reveals the risks lurking beneath what once appeared to be a genius strategy.

Indeed, as the market climate shifts, the truth may echo Warren Buffett’s sentiment: “In a bull market, everybody’s a genius.” When conditions change, the reality of who has been overexposed can become painfully clear. Today’s environment points to the vulnerabilities in Strategy’s enterprise mNAV, revealing what may have been overlooked during a thriving market. Unless Bitcoin rebounds, Strategy may increasingly rely on the asset it once postured it would never sell.

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