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MicroStrategy’s Bitcoin Bet Backfires as Shares Plunge to Multi-Month Lows

Felix Baarz by Felix Baarz
September 27, 2025
in Analysis, Bitcoin, Crypto Stocks, Market Commentary
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MicroStrategy Inc., the publicly-traded company most closely associated with Bitcoin, is witnessing a severe downturn in its share price, erasing all its gains for the year. The firm’s aggressive strategy of converting its corporate treasury into the cryptocurrency is now facing a critical test as a market-wide crypto sell-off triggers a steep decline in its equity value.

A Leveraged Bet Turns Sour

The company’s shares have entered a pronounced downward trajectory, recently tumbling 7% in a single session to touch their lowest point since April. This sharp drop is part of a broader retreat; MicroStrategy’s stock has now declined 45% from its peak in November 2024. The direct catalyst for this collapse is the recent correction in the digital currency market. As Bitcoin’s price falls, it drags down the entire crypto ecosystem, and MicroStrategy’s position as a leveraged proxy for the asset magnifies the losses. The same mechanism that propelled the stock to impressive heights during bull markets is now dramatically accelerating its descent.

Investor Confidence Erodes as Premium Shrinks

A key metric signaling waning investor confidence is the dramatic contraction of the stock’s premium to its net asset value (NAV). This premium, which reflects the market’s valuation of the company’s Bitcoin acquisition strategy beyond its mere holdings, has collapsed. It has dwindled from a high of 2x in January to just 1.44x, indicating clear signs of investor fatigue.

Should investors sell immediately? Or is it worth buying Strategy?

Compounding the pressure are reports of regulatory scrutiny. U.S. watchdogs, including the SEC and FINRA, are said to be examining MicroStrategy for unusual trading activity. The investigations are reportedly focused on elevated trading volumes observed prior to the company’s major cryptocurrency purchase announcements.

Share Dilution Strategy Meets Market Resistance

The company’s method of funding its Bitcoin acquisitions is also drawing criticism. Its most recent purchase of 850 BTC was financed through an “at-the-market” equity offering, a tactic that dilutes the ownership stakes of existing shareholders. This approach has been met with significant market disapproval, contributing to the stock’s fall to a five-month low. Investors are showing clear signs of exhaustion with the strategy of repeatedly issuing new shares to accumulate more digital assets, particularly during a market downturn. What was once hailed as a masterstroke in corporate Bitcoin strategy is now revealing its potential downsides.

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Tags: Strategy
Felix Baarz

Felix Baarz

My name is Felix Baarz, and I look back on over fifteen years of experience as a business journalist. I have always been fascinated by the mechanisms and dynamics of global financial markets as well as the complex economic and political interconnections that shape our world. With this passion, I have made a name for myself as an expert on international financial markets and dedicate myself with great commitment to making even the most complex topics understandable and accessible to my readers. My roots lie in Cologne, where I was born and raised. Early on, my curiosity about economic topics and international developments sparked my interest in journalism. After completing my studies, I began my career as a business editor at a respected German trade publication. Here I laid the foundation for my professional career, but my curiosity soon drew me out into the wider world. A turning point in my life was moving to New York, where I lived for six years and gained insight into leading media houses. In this vibrant metropolis, I was able to report firsthand from the heart of the global financial world. From daily developments on Wall Street to major economic policy decisions that make waves worldwide, I had the opportunity to write about central topics that move people and markets alike. This time shaped my perspective and sharpened my view of global interconnections.

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