Strategy's enterprise multiple-to-net-asset value fell to 0.99 on Friday June 26, below 1.0 for the first time, meaning the market priced the company's total capital structure at a discount to the bitcoin it holds, according to The Block and Crypto Briefing.
Enterprise value was estimated at $50.3 billion against bitcoin holdings worth roughly $50.6 billion. Strategy holds 847,363 BTC. MSTR fell to $82.16 on the day, a 3.5% drop to a yearly low, as bitcoin traded near $60,000.
The break below 1 mNAV matters because Strategy's bitcoin accumulation model depends on issuing equity and preferred instruments above net asset value, then using the proceeds to buy more bitcoin. Below that threshold, new issuance becomes structurally dilutive: each share or preferred instrument sold raises capital below the per-share value of the bitcoin already on the balance sheet.
That leaves the capital engine idle unless the premium returns.
STRC falls 26% below par
STRC, Strategy's Variable Rate Series A Perpetual Stretch Preferred Stock, carries an 11.5% annual dividend. It hit an intraday low of $71.40 Friday before closing at $74.72, approximately 26% below its $100 stated par value, per The Block.
The full five-series preferred stack, STRC, STRK, STRF, STRD, and STRE, carries total annual dividend obligations of approximately $1.2 billion, per Strategy's own filings and reporting by Globe and Mail. Annual rates across the series run from 8% on STRK to 11.5% on STRC. STRF and STRD each carry 10%.
Strategy's legacy software business generates approximately $477 million in annual revenue, less than half the preferred payout. If the company cannot cover those distributions through new issuance or operations, it must either draw on its roughly $1.4 billion cash reserve or liquidate bitcoin. Both paths stop accumulation; the second reverses it.
Garlinghouse criticizes Saylor's model
Ripple CEO Brad Garlinghouse told CNBC on June 26 that "financial engineering does not drive long-term value ... long-term value of any digital asset is going to be driven by utility," adding that "team Michael Saylor wasn't focused on the right stuff and that has hurt the overall market," per The Block.
Saylor responded the same day on X: "Volatility tests every capital structure. Strategy remains focused on Bitcoin, disciplined capital allocation, credit quality, and long-term value creation. We appreciate our investors and will continue to execute with transparency and resolve," per Bitcoin Magazine.