Fortune Warns of Strategy’s Financing Structure Risks as Bitcoin Premium Narrows

On June 9, according to TechFlow citing a Fortune report, a new analysis of Strategy’s Bitcoin treasury model led by Michael Saylor warned that the company’s current financing structure may face growing pressure as its stock premium to underlying net assets continues to narrow.

The report estimated that Strategy currently holds around 844,000 Bitcoin. Based on a Bitcoin price of $60,500, the holdings would be worth roughly $51.1 billion. Including the company’s software business and cash assets, total assets were estimated at around $53.6 billion. After deducting liabilities such as approximately $6.7 billion in convertible debt and $15.5 billion in preferred stock, the net assets attributable to common shareholders were estimated at around $31.8 billion. However, as of June 5, Strategy’s market capitalization was still about $41.6 billion, implying a premium of roughly 31%.

The core issue raised by the analysis is not whether Strategy still holds a large amount of Bitcoin. Instead, the question is whether the market is still willing to pay a high valuation for its so-called Bitcoin appreciation flywheel.

In the past, investors were willing to assign MSTR a significant premium partly because the company could continue raising capital through equity, convertible debt, and other financing tools to buy more Bitcoin. This effectively turned Strategy into a highly liquid public-market vehicle for leveraged Bitcoin exposure. Now, as Bitcoin has pulled back and MSTR’s share price has weakened, that premium appears more fragile.

Fortune’s concern centers on the company’s preferred stock financing chain. The analysis suggested that, in order to cover rising preferred stock dividends, Strategy may need to keep issuing more preferred stock or, under pressure, sell part of its Bitcoin holdings. This could create a negative feedback loop of issuing preferred stock, paying dividends, and refinancing again.

It is important to note that the phrase “death spiral” is a risk description used in media analysis, not an official financial conclusion disclosed by the company. Different sources may use different wording, and the related information still requires further confirmation from Strategy.

For now, the market is paying closer attention to whether MSTR’s valuation logic as a “Bitcoin proxy asset” is beginning to shift. If investors are no longer willing to pay a premium for its capital structure, Strategy’s financing efficiency, its ability to keep accumulating Bitcoin, and common shareholders’ tolerance for a highly leveraged structure could all be tested.

Why It Matters

This issue matters because Strategy is not just a company holding Bitcoin. For years, it has been treated by the market as one of the most representative vehicles for gaining Bitcoin exposure through traditional capital markets. If its high-valuation logic is repriced, the impact could extend beyond MSTR itself and challenge the broader narrative of using listed companies to amplify BTC exposure.

Another key issue is capital structure. Bitcoin volatility itself is nothing new. But when that volatility is combined with preferred stock dividends, convertible debt obligations, and refinancing needs, risk can move from the asset-price level to the liability side of the balance sheet.

At this stage, most public information still comes from media analysis. Questions around future financing plans, dividend coverage, and whether there is potential pressure to sell Bitcoin still require clearer communication from the company.

WEEX View

The core market debate is no longer simply “How much BTC does Strategy hold?” It has shifted to “Can the financing capacity of this listed-company structure continue to outperform its liability costs?”

If MSTR’s premium to net asset value continues to narrow, common stock issuance may become less efficient first. Once equity financing becomes harder, the market will quickly turn its attention to preferred stock dividend coverage, the company’s ability to issue further credit instruments, and whether Strategy may need to use part of its BTC position to maintain capital structure stability.

For front-line CEX trading businesses, this is not just a sentiment-driven headline. The real signal to watch is whether the correlation between MSTR, spot BTC, and related derivatives strengthens during U.S. equity trading hours, especially whether traders begin reinforcing a “MSTR pressure leads BTC lower” transmission path.

The second layer is the potential shift in capital flows. In the past, some traditional finance investors used MSTR-like U.S.-listed equities to gain leveraged BTC exposure because the compliance, settlement, and account infrastructure were more familiar. But if the structural discount risk of these proxy assets begins to rise, capital may rotate back into spot Bitcoin ETFs, convertible bond arbitrage strategies, or more direct BTC spot and futures combinations.

For exchanges, the most direct impact would be whether cross-market arbitrage boundaries start to widen. If MSTR volatility, ETF creation and redemption expectations, CME basis, and spot market depth all move abnormally at the same time, it would suggest that the market is beginning to reprice the risk of the listed-company Bitcoin treasury model.

The next three signals worth watching are clear. First, whether Strategy continues to expand preferred stock or other credit-based financing tools. Second, whether management gives a clearer response on the possibility of selling part of its Bitcoin holdings. Third, whether MSTR’s premium to net asset value compresses further.

If all three move in a negative direction, market confidence in Strategy’s “finance-to-buy-Bitcoin flywheel” could weaken significantly, potentially affecting the pricing of institutional products built around BTC exposure.

Timeline

• 2026-03-27: Strategy’s perpetual preferred stock STRC was reported to be around 80% held by retail investors. It pays monthly dividends with an annualized yield of about 11.5% and has been used to raise funds for Bitcoin purchases.
• 2026-05-07: Michael Saylor said Strategy is turning Bitcoin into digital credit through STRC and digital equity through MSTR, reinforcing its strategy of expanding Bitcoin exposure through capital market instruments.
• 2026-05-21: Saylor said the company aims to expand the scale of STRC in order to buy more Bitcoin and increase BTC holdings per share.
• 2026-05-23: Saylor suggested that the company would not rule out selling part of its Bitcoin this year, which further fueled discussion around potential Bitcoin sales under financing pressure.