For the first time in this cycle, Wall Street is valuing Michael Saylor’s MicroStrategy (MSTR) at less than the Bitcoin it holds.
The stock slipped to a discount relative to its Net Asset Value (NAV) Thursday, signaling a potential end to the “infinite money” arbitrage that defined its 2024 rally. While Bitcoin reclaimed $92,000 on November 28, MSTR shares languished near $180, failing to match the crypto asset’s recovery.
The Numbers: Smart Money Exits
The premium collapse coincides with a massive institutional exodus. Filings reveal that heavyweights—including BlackRock, Fidelity, and Vanguard—offloaded approximately $5.4 billion in MSTR shares during Q3 2025.
The rotation is clear: institutions are swapping the volatile proxy for spot ETFs.
“Investors are no longer rewarding Saylor’s leverage; they are discounting it,” wrote analyst James Foord in a note to clients. “The high premium that once attracted investors is gone.”
The Mechanism Breaks
This discount is existential for Saylor’s strategy. For years, MicroStrategy traded at a 1.5x to 2.5x premium, allowing the company to sell overpriced stock to buy Bitcoin—an accretive loop that increased Bitcoin-per-share for holders.
With the stock trading below 1.0x NAV, that flywheel jams. Issuing new equity now would be dilutive, effectively punishing existing shareholders rather than rewarding them.
The Outlook
The divergence is stark. Bitcoin is up; MSTR is down. Unless the premium returns, Saylor loses his primary weapon for aggressive accumulation, leaving the company to rely on debt issuance in a high-rate environment. The market is waiting to see if Saylor halts the buying spree—or doubles down at a cost.
