$18 Billion Was Lost in MicroStrategy — Now the Next Wave of Winners Is Positioning. Here's What They're Seeing.

Why this report matters

For months, the market decided MicroStrategy was finished — a broken Bitcoin proxy with no catalysts and an exhausted playbook. Yet beneath the capitulation, something shifted, and catalysts are approaching, with one just days away. A setup like this doesn’t appear often — and when it does, it rarely looks bullish at first glance. The last time sentiment looked this washed-out, the stock went on a multi-month tear. Now, another inflection point is approaching — but this time, the payoff profile looks very different.

Bitcoin (LHS) vs. Microstrategy (RHS) - broken forever? See our trades below

Main argument

We turned bearish on MicroStrategy in May 2025 (here, here, here). We repeatedly highlighted that shares were likely to fall from ~$400 to $330 and potentially to $300, driven by declining Bitcoin volatility and a normalization of the company’s net asset value premium (NAV). While the consensus narrative assumed MicroStrategy could continue raising capital indefinitely through equity and convertible bond issuance, that ability is highly dependent on elevated volatility and strong market sentiment — conditions that faded into the summer. Something big is about to shift for MicroStrategy:

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