The world's largest corporate holder of Bitcoin, Strategy, is gradually moving away from its long-held principle of "never selling any Bitcoin holdings." After accumulating Bitcoin valued at $67 billion, Michael Saylor, Co-founder and Chairman of Strategy, stated on Tuesday that the company would consider selling Bitcoin if such a move improves the firm's capital structure or enhances its "Bitcoin per share" metric—a key indicator used to promote the stock to investors.
Saylor compared Strategy to a real estate developer, outlining a potential future scenario involving Bitcoin sales. He explained that if a company buys land for $10,000 per acre and later sells it for $100,000, using the proceeds to acquire more land or to pay down debt interest, no one would view this as detrimental to real estate value or as evidence of a failed business model. "A real estate development company exists to buy low and sell high," Saylor said. "We are like a Bitcoin development company." He added, "You use credit to buy back Bitcoin, let it appreciate, and then sell Bitcoin to pay dividends. As long as the credit issued exceeds the break-even point, this business model can continue to operate and grow."
This so-called "digital asset treasury" (DAT) business model, pioneered by Saylor, has faced pressure since cryptocurrency prices fell sharply last October. Saylor's comments on Tuesday highlight Strategy's evolution from a simple Bitcoin accumulation strategy to a more complex balance sheet management approach influenced by debt costs, preferred stock obligations, and shareholder preferences.
In a 2024 interview, when asked when the company might sell its Bitcoin holdings, Saylor had stated there was "no reason to sell the winner." However, in recent months, Strategy began hinting that it might eventually need to sell some Bitcoin to fulfill dividend commitments. Last November, Strategy CEO Phong Le indicated that selling Bitcoin would be considered a last resort. In the latest earnings call, Le's stance became more explicit: "If selling Bitcoin for dollars, or using Bitcoin sales to purchase debt, enhances the Bitcoin per share, we would consider doing so in the future. We won't just sit here and say we will never sell Bitcoin."
In October last year, S&P Global Ratings assigned Strategy a junk-level credit rating, citing high business concentration among its reasons. The rating agency noted that Strategy's convertible debt could mature during periods of Bitcoin price pressure, potentially forcing the company to sell tokens at "depressed prices." Derek Lim, Head of Research at crypto market maker Caladan, suggested this rating marked the beginning of a shift in Strategy's "never sell" position, with Le's recent remarks "simply making the change more explicit, though hints were already there."
Former Goldman Sachs trader Rich Rosenblum argued this does not signify a permanent shift for Strategy. He noted, "The weakening of Strategy's premium, coupled with Bitcoin's underperformance relative to gold, may have brought about a 'sobering moment.' Now, he is willing to realize some profits and lock in a higher cost basis in case prices fall again before the crypto bear market ends."
Signs of this strategic shift were already apparent. In December, the company established a dollar reserve, now totaling $2.25 billion, specifically to ensure it can meet preferred dividend payments and debt interest obligations. Previously, Strategy funded Bitcoin acquisitions solely through issuing new shares and bonds. Against the backdrop of significant Bitcoin price declines, a strategy reliant purely on passive accumulation without active management has clearly placed increasing financial strain on the company.
The core of this strategic adjustment is a change in Strategy's performance evaluation metrics—shifting focus from "how much Bitcoin is held" to "how much Bitcoin each share represents." This shift implies that selling some Bitcoin under specific circumstances could align with the company's long-term interests if it boosts the Bitcoin value per share.
Strategy has previously navigated severe challenges. As early as February 5th, Bitcoin prices had halved from their all-time highs, and Strategy's common stock, used to raise funds for Bitcoin purchases, fell even more sharply. The company reported a net loss of $12.5 billion for the first quarter, directly reflecting the impact of Bitcoin's price decline on its book value at the start of the year.
However, as Bitcoin prices recovered to $80,000, Strategy's stock price rebounded. This recovery is largely attributed to a hybrid security Strategy began issuing last year—perpetual preferred shares. These dividend-paying securities are used to finance Saylor's current Bitcoin buying spree. Market observers believe that, amid overall market uncertainty fueled by military conflicts in the Middle East, Strategy—which purchased over $4 billion worth of Bitcoin in April—has helped support demand for the cryptocurrency.
This niche type of security is typically used by banks, utilities, and real estate companies to meet regulatory capital requirements and is mainly issued to institutional investors. Strategy, however, has marketed its product, called "Stretch preferred shares," to retail investors through platforms including Robinhood and Charles Schwab, promoting its high yield—approaching junk bond levels—as an alternative to money market funds.
Michael Youngworth, Head of Global Convertibles and Preferred Securities Strategy at Bank of America, commented, "They found an audience. These people trust 'Strategy Bank.' You need to be able to tolerate risk, but if you understand it, this product is attractive to retail investors. That explains why they can keep issuing."
Before Strategy's common stock plummeted nearly 50% last year, Saylor was able to leverage the premium between the stock price and Bitcoin's value, raising funds through stock issuance without causing significant dilution during the bull market. When this premium nearly vanished, skeptics, including prominent short-seller Jim Chanos, began betting against the stock, arguing the strategy was unsustainable. The premise of this Bitcoin accumulation strategy is that the cryptocurrency's price will continue to rise, attracting more investors afraid of missing out. If demand wanes, Strategy risks being unable to continue financing purchases, disrupting its "flywheel effect."
Nevertheless, Saylor stated at the Bitcoin 2026 conference in Las Vegas last week, "Ultimately, the reason we can do this is because we are not relying on cash flow from operating businesses to fund it. We are accomplishing this through capital investment. The key question is, can you achieve an 11.5% return on capital investment over the long term?"
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