For years, the company commanded a premium well above the value of its bitcoin holdings, giving it wide latitude to raise capital — a strategy that Michael Saylor and his team fully exploited.

That dynamic has now shifted, with Strategy’s (MSTR) enterprise multiple to net asset value (mNAV) falling below 1.

This is a notable change for the firm, which had long benefited from valuations exceeding its bitcoin reserves. That premium once enabled easy access to funding, but the advantage has now reversed.

With shares trading near $82 — roughly 85% below their November 2024 peak — the company’s enterprise value has dropped to about $50.4 billion. In contrast, its bitcoin holdings are valued at approximately $51.1 billion at a $60,000 BTC price. As a result, the market is now pricing the company below the value of its bitcoin assets. At this level, issuing new equity would be dilutive, as shares would be sold for less than the underlying asset value.

Enterprise mNAV is calculated by dividing total enterprise value — including market cap, debt, and preferred equity, minus USD reserves — by the value of bitcoin holdings.

While Strategy still has the option to issue shares, doing so under current conditions could trigger further criticism. Its recent bitcoin purchases have already diluted existing shareholders, drawing negative reactions from the market.

There is also rising concern that the company is being valued more like a closed-end fund than an operating business. Similar structures have historically traded at premiums during bullish periods, only to fall into persistent discounts as sentiment weakened, often due to the absence of effective redemption mechanisms.

Even so, Strategy retains more flexibility than traditional closed-end funds. It can issue debt or equity when conditions are favorable, refinance liabilities, generate cash flow from its core software business, and actively manage its capital structure.