Fortune Says Strategy Preferred-Stock Approach Could Increase Downside Pressure on Shares

Fortune reported that Strategy’s preferred-stock-backed Bitcoin buying strategy could add downside pressure to the shares. With Bitcoin prices weakening, the company is facing scrutiny over both the dividend burden from preferred stock and the premium at which the stock still trades relative to net asset value.

On June 9, Fortune said Strategy continues to trade at a substantial premium to the value of its assets. The company’s holdings are made up mostly of Bitcoin, and after deducting debt and preferred-stock obligations, the underlying value attributable to common shareholders is below the current market capitalization.

Fortune said Strategy holds 844,000 BTC. Assuming a Bitcoin price of $60,500, those holdings would be worth about $51.1 billion. Adding roughly $1.5 billion for the legacy software business and about $1 billion in cash brings total liquid and saleable assets to an estimated $53.6 billion.

The company also carries obligations tied to convertible notes and preferred stock. Fortune estimated that Strategy has about $6.7 billion in convertible notes, translating to roughly $6.2 billion in debt obligations at market value. Adding $15.5 billion in preferred stock brings total debt and preferred-stock obligations to about $21.8 billion.

After subtracting those obligations, net asset value attributable to common shareholders comes to about $31.8 billion. As of June 5, however, Strategy’s market capitalization stood at $41.6 billion, leaving the shares trading at roughly a 31% premium to net asset value, Fortune said.

Fortune described that premium as the so-called “Saylor magic premium.” In the past, Executive Chairman Michael Saylor used the company’s elevated share price to raise capital and buy more Bitcoin, increasing Bitcoin holdings per share. More recently, though, Strategy’s stock has swung more sharply than Bitcoin itself, testing the sustainability of that structure.

Expanded preferred-stock issuance has also been identified as a source of pressure. Fortune said Strategy has sharply increased preferred-share issuance since early 2025, effectively raising its leverage to Bitcoin prices. The report also highlighted a structure that requires the company to pay about $1.5 billion in preferred dividends each year.

Cash holdings are estimated at about $1 billion. That would cover less than one year of annual preferred dividends, according to Fortune. If the dividend burden persists, the company could become more likely to issue additional preferred shares or sell Bitcoin.

Strategy previously sold some of its Bitcoin to fund preferred dividend payments. The sale was limited in size, but it raised concerns in the market about whether Saylor’s long-term holding principle was starting to weaken.

Still, Strategy later said it bought an additional 1,550 Bitcoin, bringing its total holdings to 845,256 BTC. The company also said it increased its dollar reserves to $1 billion. The move was seen as an effort to manage both its Bitcoin accumulation strategy and its preferred-dividend structure.

Fortune said Strategy shares could face a steeper correction if Bitcoin falls further. As Bitcoin declines, the value of the company’s holdings shrinks while debt and preferred-stock obligations remain fixed.

Because Strategy remains the leading example of a Bitcoin treasury company, the market is watching whether its preferred-stock strategy and dividend-paying capacity will affect sentiment across Bitcoin-related stocks. Bitcoin’s price trend, the dividend structure of STRC, and whether the company raises additional capital are the key variables ahead.