Michael Saylor-led Strategy Inc. (NASDAQ: MSTR), formerly MicroStrategy, closed at $143.19, down 9.63%, and later slipped to $139.71 in overnight trading. The plunge is intensifying scrutiny of the company’s aggressive Bitcoin-centric business model. The stock fell into the $143–$149 range this week, as investors reassessed mounting losses, balance-sheet risk, and a growing debate around dividend sustainability.
The sell-off comes amid renewed volatility in Bitcoin (BTC), which remains the dominant driver of Strategy’s valuation and investor sentiment.
The Dividend Dilemma Sparks Fresh Controversy
The latest flashpoint emerged on X (formerly Twitter), where Strategy Chairman Michael Saylor highlighted its 11% annual dividend.
“$STRC delivers the first 11% of BTC ARR with ~85% of the volatility engineered out,” He wrote on X.
That claim immediately drew fire from economist and longtime Bitcoin critic Peter Schiff, who questioned the financial mechanics behind the payout.
Peter Schiff Questions Funding Behind STRC’s 11% Yield
Schiff publicly challenged Saylor, asking: “Yes, but where does the money come from to pay the 11% yeild? MSTR is losing money. Paying the yield just adds to those losses.”
The exchange resonated with investors already uneasy about Strategy’s cash flow profile. Critics argue that because Strategy’s core software business no longer generates sufficient profits, dividends may ultimately be funded through new equity issuance or debt, raising concerns about dilution and long-term sustainability if Bitcoin prices remain under pressure.
MSTR Hits a 15-Month Low as Bitcoin Volatility Bites
Technically, MSTR has entered a vulnerable zone. Shares have dropped to levels not seen since late 2024, reflecting both weakness in Bitcoin and declining confidence in leveraged BTC exposure through public equities.
Bitcoin remains Strategy’s primary treasury reserve asset, and fluctuations in BTC prices have an outsized impact on MSTR compared with traditional tech peers listed on the Nasdaq.
Trading Below NAV: A Rare Discount Raises Red Flags
For the first time in months, Strategy is trading at a discount to its Net Asset Value (NAV). The company’s Bitcoin holdings are estimated to be worth approximately $59 billion, while its market capitalization has fallen below $50 billion.
Historically, MSTR has commanded a premium to NAV due to its leverage, liquidity, and institutional accessibility. The reversal into discount territory is being interpreted by some analysts as a signal of fading confidence in the strategy’s risk-reward profile.
Adding to the pressure are concerns surrounding MSCI, which is reviewing how it classifies companies with large digital asset treasuries. Any unfavorable reclassification or removal could force passive funds to reduce exposure, potentially triggering billions of dollars in additional selling.
Such an outcome would disproportionately impact Strategy, given its size and visibility among institutional crypto-linked equities.
Michael Saylor Doubles Down on Bitcoin Strategy
Saylor has repeatedly stated that Strategy’s mission is to maximize long-term Bitcoin ownership, even at the cost of short-term volatility. With MSTR at a 15-month low, trading below NAV, and facing scrutiny over its 11% dividend, the coming months may prove decisive in determining whether this bold bet delivers asymmetric upside or exposes bigger structural risk.
