Garlinghouse Sees Bitcoin Upside, Questions Saylor’s Effect on Market

For years, Strategy traded at a sizable premium to the value of its bitcoin holdings, giving the firm broad flexibility to raise capital — a dynamic Michael Saylor and his team capitalized on.

That premium has now vanished. Strategy’s (MSTR) enterprise multiple to net asset value (mNAV) has slipped below 1, marking a significant shift in investor perception.

With the stock hovering around $82 — roughly 85% below its November 2024 peak — enterprise value has fallen to about $50.4 billion. By comparison, its bitcoin holdings are valued near $51.1 billion at a $60,000 BTC price. The market is effectively pricing the company below the value of its underlying assets, meaning any new share issuance would be dilutive.

Enterprise mNAV is calculated by dividing enterprise value — including market cap, debt, and preferred equity, minus cash — by the value of the firm’s bitcoin reserves.

While Strategy still has the option to issue equity, doing so at current levels could trigger further criticism. Its recent bitcoin purchases have already drawn backlash for diluting existing shareholders.

There is growing concern that the company is being valued more like a closed-end fund than an operating business. Similar vehicles, such as the Grayscale Bitcoin Trust before its ETF conversion, historically traded at premiums during periods of strong demand but later shifted to persistent discounts as sentiment weakened. These discounts tend to persist due to the lack of a redemption mechanism linking share prices to underlying asset value.

Still, Strategy maintains greater flexibility than traditional closed-end funds. It can raise capital through debt or equity when accretive, refinance liabilities, generate cash flow from its software operations, and actively manage its capital structure.