MicroStrategy Stock Falls Below Bitcoin Holdings, Highlighting Investor Caution

Strategy (formerly MicroStrategy) briefly traded below the value of its Bitcoin holdings this week, signaling growing investor caution toward the world’s largest corporate holder of BTC. The company’s market capitalization slipped to about $65.34 billion, falling under the $66.59 billion value of its 641,692 Bitcoin—a rare occurrence that underscored market unease.

This short-lived negative premium reflected how investors are increasingly pricing in corporate risk and dilution concerns beyond the company’s Bitcoin exposure. Typically, MicroStrategy trades at a premium, with equity investors paying extra for its leveraged Bitcoin strategy. However, as Bitcoin prices hovered between $100,000 and $105,000, MicroStrategy’s shares saw sharper declines, emphasizing the market’s preference for direct Bitcoin exposure over corporate intermediaries.

The divergence came as MicroStrategy continued issuing equity and preferred shares to fund further Bitcoin purchases. The company recently added 487 BTC for $49.9 million, maintaining its aggressive accumulation strategy despite the stock pressure. Yet, this expansion of leverage and dilution risk made some investors wary, temporarily pushing the stock below its net asset value.

Meanwhile, Bitcoin itself showed relative stability amid weak sentiment, with the Fear and Greed Index deep in “extreme fear.” Traders viewed BTC as a cleaner, more straightforward asset compared to MicroStrategy’s complex financial structure. The quick recovery of the stock above its Bitcoin-equivalent value demonstrated resilience, but the episode revealed a shift in institutional behavior.

Markets are now distinguishing between Bitcoin as a decentralized asset and MicroStrategy as a leveraged corporate vehicle. The brief discount highlighted how investors increasingly favor pure crypto exposure, rewarding Bitcoin’s transparency while demanding a risk premium for equity-based alternatives.