Why Michael Saylor is stocking up on US dollars

A historical and financial analysis of a dramatic strategic pivot

Michael Saylor has never shied away from sweeping statements about the fate of money. For years he has insisted that the United States dollar behaves like a melting ice cube and that the rational path for companies seeking survival is to accumulate Bitcoin at all costs.

His company Strategy, formally MicroStrategy transformed itself into the flagship of corporate Bitcoin treasuries, raising many billions through equity and convertible debt to buy as much Bitcoin as possible. Supporters saw him as a visionary who discovered a new form of corporate leverage. Critics saw him as the architect of an enormous speculative bubble.

Today that bold narrative has been complicated by a simple and surprising development. Strategy, after announcing yet another purchase of Bitcoin worth roughly one billion US dollars, is now raising substantial amounts of US dollars for defensive purposes. The firm recently issued 1.4 billion US dollars in equity not to buy Bitcoin but to create a cash reserve to meet the dividend obligations on five classes of preferred shares.

At the same time, the company’s volatile stock price continues to slide, erasing much of the premium over its net Bitcoin holdings that powered the speculative cycle. For a man who spent years dismissing fiat currency as a relic of a broken financial order, the decision to build a dollar buffer marks a striking reversal.

This article explores why a long-time critic of the dollar is suddenly stocking up on it and what the shift means for the health of Strategy, its shareholders and the broader crypto-treasury model that emerged during the last two years.

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How the corporate Bitcoin flywheel operated

To understand today’s shift, it helps to recall how the crypto-treasury phenomenon developed. The model began with Strategy. The company issued stock at a time when investor enthusiasm for Bitcoin and for Saylor’s promotion of it ensured that its shares traded at a substantial premium to the value of Bitcoin held on the balance sheet.

The premium created a loop. If the stock traded at 200 US dollars while representing 100 US dollars of Bitcoin, Strategy could issue a new share at 200 US dollars, use the full amount to buy more Bitcoin, and thereby raise the number of Bitcoin per share. What normally would be dilution became accretive. Investors enjoyed Bitcoin exposure plus the psychological comfort of holding a stock rather than a leveraged position on an exchange.

Volatility added another layer. Strategy’s stock behaved with the energy of a meme stock. Hedge funds bought its convertible bonds and hedged their exposure by shorting the stock. Through gamma trading they profited from movements in the share price regardless of the company’s long-term prospects. The arrangement suited Saylor because it delivered inexpensive capital. It suited traders because it delivered volatility. It suited retail investors because they saw their holdings swell when Bitcoin rose and when Strategy issued more shares.

This structure encouraged copycats. Dozens of listed companies began to imitate the strategy with various tokens. The assumptions behind the structure were fragile but simple. The stock needed to maintain its premium. Volatility needed to remain high. Crypto prices needed to trend upward. And the company needed no meaningful business operations beyond buying more crypto.

The breakdown of the premium

By mid-2025 those conditions were weakening. Bitcoin softened. Retail enthusiasm for meme-style trading declined. Shareholders began to question why they should pay two dollars for exposure to a single dollar of Bitcoin when other listed vehicles offered Bitcoin at moderate discounts or at parity. As the premium contracted, the flywheel slowed. Strategy’s stock, which had once magnified Bitcoin gains upward, began magnifying losses instead. Year to date, Bitcoin has slipped a few percentage points, yet Strategy’s stock has fallen by roughly forty percent.

At the same time, the cost of the strategy began to reveal its scale. Strategy must service more than 800 million US dollars each year in dividends and debt interest payments. The firm is exposed to market conditions without the buffer that a diversified operating business usually provides. When the stock traded well above the firm’s net asset value, raising capital seemed almost painless. When the stock trades close to parity, raising capital becomes expensive and dilutive in the conventional sense. The arithmetic behind the miracle starts to resemble the arithmetic behind any highly leveraged asset play.

Mounting pressure and the corporate Bitcoin collapse

The collapse in valuations among similar firms illustrates how precarious the sector has become. Several crypto-treasury imitators are now selling tokens to finance buybacks or to meet debt obligations. A notable example came from a chipmaker that pivoted to a Bitcoin treasury only to liquidate much of the position months later to pay creditors. In Japan, Metaplanet raised loans against their Bitcoin after the stock fell by eighty percent. In the United Kingdom, a once-celebrated company pursuing the model now trades at a discount to its holdings.

In the United States, leveraged ETFs tied to Strategy stock have endured staggering losses. Many are down more than eighty percent for the year. Retail traders who embraced these products now find themselves frozen in positions that have been all but wiped out.

These developments matter because Strategy sits at the centre of this landscape. Its brand, its chairman and its balance sheet helped legitimise the idea that a struggling listed company could transform itself through Bitcoin accumulation and investor excitement. As the model breaks down across the market, confidence in Strategy’s version of it has weakened.

Why Saylor is turning to the US dollar

Against this backdrop Saylor’s dollar accumulation looks less like a philosophical change and more like a necessity. Strategy must ensure that it can meet its preferred dividend obligations and maintain solvency in the absence of the premium that once supported it. If it fails to do so, the entire structure unravels.

The choice to issue 1.4 billion US dollars in stock was an acknowledgment that a period of pure Bitcoin accumulation has ended. A company with debt obligations cannot rely solely on Bitcoin’s price movements to meet its cash commitments.

Saylor himself may still believe that the dollar is weakening over time, but in the short term the dollar remains the global unit in which obligations must be paid. It is liquid, predictable and widely accepted. Bitcoin is neither sufficiently stable nor sufficiently predictable for this purpose.

The decision to hold US dollars also protects the firm from volatility in a period when Bitcoin prices have softened and when Strategy’s stock has lost the violent enthusiasm that once attracted hedge funds. Without a consistent premium there is less scope for issuing powerfully accretive new shares. If the company cannot lean on its equity for effortless leverage, it must rely on conventional liquidity management.

This defensive approach does not negate Saylor’s long-held thesis about Bitcoin as an asset. It reflects the limits of the corporate vehicle he built to pursue that thesis. Bitcoin may be his long-term store of value, yet the dollar remains the medium through which corporate life is conducted. This was always the case. What has changed is the need to acknowledge it publicly.

The political and psychological backdrop

Saylor’s narratives about Bitcoin have been bold, sweeping and sometimes quasi-theological. His famous comparison of the dollar to a melting ice cube resonated with an audience that viewed Bitcoin as a breakthrough in monetary technology. But corporate finance does not operate through slogans. It operates through cashflows, solvency ratios and the ability to meet obligations in the currency that creditors expect.

A large segment of the audience that supported Strategy’s transformation treated the company as a symbol of a new economic order rather than as a balance sheet with real liabilities. They believed that Bitcoin adoption would accelerate, that premiums would persist and that equity markets would reward increasingly bold accumulation. Those beliefs helped sustain the strategy, but they were also fragile.

The current decision to hold dollars invites accusations of contradiction. It does not, however, represent hypocrisy. It represents the collision between ideology and corporate arithmetic. Even an aggressive Bitcoin accumulator must protect his company from bankruptcy and preserve operational flexibility.

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What this means for the future of Strategy

Strategy must now navigate a more complicated environment. The premium that enabled the strategy has shrunk. The company faces significant annual obligations. Its stock has lost its gravitational pull over speculators. And many similar firms are unwinding their positions through forced sales.

At the same time Saylor has continued buying Bitcoin. The company recently added roughly 10,000 coins at a cost of one billion US dollars. This dual move buying Bitcoin while raising dollars tells a story of a firm straddling two priorities. On the one hand Saylor remains committed to Bitcoin’s long-term potential. On the other hand, he recognises the need to defend the company with liquidity that Bitcoin cannot reliably provide in the short term.

The strategy could succeed if Bitcoin prices stabilise and recover while the firm preserves its dollar buffer. It could falter if Bitcoin enters a prolonged downturn or if equity markets lose patience with the dual structure. In the absence of the premium, Strategy must act more like a traditional company that holds a concentrated asset rather than a self-reinforcing financial machine.

A sign of broader structural change

Saylor’s pivot also signals a broader shift. The era of the corporate Bitcoin treasury, which flourished on volatility and easy capital, appears to be closing. This does not mean that companies will stop holding Bitcoin. It means the model in which firms transformed themselves into specialised crypto-holding vehicles for speculative gains is less sustainable without the momentum of retail mania and the premium-based leverage that once accompanied it.

Strategy’s decision to shore up its dollar position is therefore not an isolated event. It is part of a wider cycle in which the most extreme form of corporate crypto speculation is giving way to financial discipline.

Conclusion

Michael Saylor is known for uncompromising language about money, technology and the future. Yet even he must operate within the constraints of corporate finance. The decision to accumulate US dollars during a period of Bitcoin purchases shows how far the environment has shifted. Strategy must now protect itself against a downturn in its stock price, rising obligations and shrinking premiums. The company is still buying Bitcoin, but it must hold enough dollars to survive.

For the many spectators who believed that Strategy had escaped financial gravity, this reversal is significant. It demonstrates that every corporate Bitcoin strategy, no matter how bold, eventually meets the arithmetic of cashflow. If Strategy adapts successfully, the move may be remembered as prudent. If it fails, it will be remembered as the moment the model’s limits became impossible to ignore.

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