Michael Saylor’s Bitcoin Bet Faces Reality Check as Strategy Slips

Strategy, formerly MicroStrategy, is one of the biggest Bitcoin advocates. For years, the business intelligence firm has been buying BTC, adding the digital gold into its balance sheet. So far, MicroStrategy is the largest holder of BTC with over 687,000 BTC worth over $63Bn.

While their strategy has been an inspiration to many other public companies, including MetaPlanet, MicroStrategy is facing challenges: The Bitcoin price has, in recent months, been stalling, even dropping. As a result, the MSTR stock has been under immense selling pressure, dropping at a faster rate than Bitcoin itself.

When writing, the MicroStrategy stock is changing hands above $173. It is down -53% year-to-date. Meanwhile, at spot rates, the Bitcoin price is down just +11% in the last year. Historically, the MSTR stock traded at a 2x+ premium to its Bitcoin holdings.

MicroStrategy MSTR stock has been under immense selling pressure, dropping at a faster rate than Bitcoin itself

(Source: Strategy)

In mid-January 2026, that premium has collapsed, with the stock occasionally trading at a discount to its Net Asset Value (NAV); a rare event that signals investor fear.

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Why is MicroStrategy MSTR Stock Falling Faster Than Bitcoin

Given this divergence, it is no wonder that the Bitcoin-focused public company is under fresh scrutiny. Interestingly, critics are heavy on MicroStrategy just when more public firms are actively buying Bitcoin, adding them to their balance sheets.

This pessimism on MicroStrategy makes sense. While it is a business intelligence firm, it no longer acts like a normal software company. It operates as a Bitcoin treasury company, which means it uses stock sales and borrowed money to buy Bitcoin and hold it long term. Criticism of their plan has intensified due to recent risks that could decimate the firm and their Bitcoin strategy.

Recently, the MSCI reviewed whether “digital asset treasury” firms with more than +50% of their assets in crypto as “funds” rather than “operating companies” should be removed. This reclassification will directly impact MicroStrategy. JPMorgan estimated that a removal from the MSCI index could trigger up to $8.8Bn in passive outflows.

What’s more? To fund its recent purchase of 13,627 BTC in early January, the company issued over $1.1Bn in new stock. While they are buying more BTC, the constant issuance of new shares dilutes existing shareholders. If the Bitcoin price doesn’t grow faster than the share count, the “Bitcoin-per-share” value actually drops.

And it gets worse. In Q4 2025, they reported $17.44Bn unrealized loss. Now, critics are pointing to the company’s legacy software business, which generates only about $125M in operating cash flow. This is nowhere near enough to service the billions in debt used to buy the Bitcoin.

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What’s Next for MicroStrategy?

Despite criticism and obvious pressure, Saylor has remained defiant. In a podcast, he argued that a company losing $10M in operations is “saved” if its Bitcoin gains $30M.Moreover, the founder maintains that MicroStrategy is a “Bitcoin Development Company” and that traditional cash-flow metrics are obsolete in a digital-asset economy.

Bullish as Saylor is, MicroStrategy’s fortunes now squarely depend on how the Bitcoin price and some of the top Solana meme coins evolve. If crypto prices tick higher, the MSTR stock will begin trading at a premium to its net asset value, which is nothing more than its Bitcoin stash. Once this premium increases, the “MSTR flywheel” will begin spinning again, allowing them to issue shares at a high price to buy Bitcoin at a low relative cost.

The higher premium may also allow MicroStrategy to pivot back to using low-interest convertible debt instead of pure equity issuance. When this happens, dilution concerns will fade, boosting their “Bitcoin Yield. By end of 2025, the yield stood at over +22%.

MicroStrategy MSTR stock has been under immense selling pressure, dropping at a faster rate than Bitcoin itself

(Source: Strategy)

Beyond prices, MSCI needs to officially confirm that “Digital Asset Treasury Companies” like MicroStrategy will be part of the index. Once they do, MicroStrategy will find relief, and the threat of the over $9Bn in forced selling removed, stabilizing the MSTR stock price.

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The post Michael Saylor’s Bitcoin Bet Faces Reality Check as Strategy Slips appeared first on 99Bitcoins.

Michael Saylor’s Bitcoin Bet Faces Reality Check as Strategy Slips