A House Of Cards Built On Bitcoin: Why Strategy Inc. Can’t Outrun Its 90-Day Clock
Anndy Lian
A House Of Cards Built On Bitcoin: Why Strategy Inc. Can’t Outrun Its 90-Day Clock
Let me begin by saying this. I have nothing against Bitcoin, but did see flaws in the treasury model. I have also voiced that out in an earlier article, too.
There is a certain seduction in the story of Strategy Inc., the company formerly known as MicroStrategy, that has bewitched investors, pundits, and even seasoned crypto natives for years. On the surface, it appears to be a grand corporate embrace of digital gold: a publicly traded entity hoarding Bitcoin not as a speculative side bet, but as a strategic treasury reserve. In a world drowning in fiat inflation and institutional timidity, Strategy Inc. seemed to offer a rare act of conviction, a bold bet on a post-fiat future. But look closer, and the illusion evaporates. The company reported just 54 million dollars in cash on hand, yet faces more than 640 million dollars in annual preferred dividend obligations. Its legacy software business, once the engine of its existence, remains cash-flow negative. There is no internal engine generating the capital needed to sustain its promises. Instead, Strategy Inc. has built a financial house of cards powered entirely by external capital markets, one that only functions so long as investors are willing to keep buying in.
And for a while, they did. From January through September 2025 alone, the company raised 19.5 billion dollars, not to buy more Bitcoin, but to refinance existing debt. This is not innovation. It is recursion. It is a system where new equity and debt issuances are used to pay dividends to prior investors. The only reason this did not feel like a Ponzi scheme was that Strategy’s stock consistently traded at a significant premium to its Bitcoin net asset value. At a 2x premium, every new share issuance effectively increased per-share Bitcoin ownership for existing holders, a virtuous loop that masked the underlying insolvency of the model. But that premium has now vanished. As of late 2025, Strategy trades roughly at par with its Bitcoin net asset value. The magic is gone. Issuing new shares no longer enriches existing shareholders. It dilutes them.
This shift is catastrophic for a model that depends entirely on perpetual capital inflows. Without a premium, there is no arbitrage advantage to issuing equity. Without equity issuance, there is no way to fund those monstrous preferred dividends, especially now that management has raised the dividend rate from 9.0 percent in July to a jaw-dropping 10.5 percent by November. This is not confidence. It is panic. The structure includes no cap on the dividend rate, meaning that every time the common share price dips below 100 dollars, the yield automatically ratchets higher to attract buyers. It is a feedback loop of compounding desperation: lower price, higher yield, greater capital burn, greater pressure on price. The math is accelerating toward a cliff.
The most immediate existential threat is not market sentiment or macro volatility. It is mechanical. On January 15, 2026, MSCI will implement a rule change excluding any company with more than 50 percent of its assets in digital currency from its indices. Strategy Inc. holds 77 percent of its balance sheet in Bitcoin. This is not a judgment call. It is a binary, algorithmic exclusion. JPMorgan estimates the delisting could force passive funds to dump 2.8 billion dollars in Strategy stock immediately. If other index providers follow suit, the total outflows could swell to 8.8 billion dollars. In a stock where 15 to 20 percent of its market cap is already tied to algorithmic strategies that trade on technicals rather than fundamentals, such a forced selloff could trigger a death spiral.
We got a preview of this vulnerability on October 10, 2025. In just 14 hours, Bitcoin dropped 17 percent, order book depth evaporated by 90 percent, and 19 billion dollars in leveraged positions were liquidated across the ecosystem. The event laid bare a fundamental truth: Bitcoin’s market, for all its headline size, remains structurally shallow. The notion that Strategy Inc. could offload 1 billion dollars of Bitcoin annually without moving the market is pure fantasy, shattered not by theory but by real-time data. If the company is forced to sell even 100,000 of its 649,870 coins to meet obligations, it would not just depress the price. It could ignite a systemic cascade, especially if leveraged players interpret the sale as a signal of institutional capitulation.
This is not a critique of Bitcoin, far from it. Bitcoin, as a decentralized, censorship-resistant, apolitical monetary network, remains as compelling as ever. It will likely outlive Strategy Inc., the Federal Reserve’s current chair, and possibly even the dollar’s global reserve status. The issue is not the asset. It is the attempt to graft Bitcoin’s infinite time horizon onto a corporate entity bound by quarterly earnings, SEC disclosures, and 90-day liquidity windows. Sovereign treasuries have operated for centuries. Corporations operate on credit cycles. You cannot run a company like a nation-state, especially when that company has no real operating income and is leveraged to the hilt on a volatile asset.
Strategy Inc.’s entire thesis rests on the assumption that capital markets will remain infinitely accommodating, that investors will always be there to buy newly issued shares or bonds to fund its preferred dividends. But markets are not infinite. They are cyclical, emotional, and brutally efficient at exposing leverage masquerading as strategy. The moment the premium disappeared, the model broke. The moment the index exclusion became inevitable, the countdown began.
We will know the outcome by March 2026. Either Strategy Inc. will be forced into a humiliating restructuring, slashing its preferred dividend, selling Bitcoin at a loss, and retreating into a shadow of its former self, or it will collapse entirely, taking with it the credibility of the entire corporate Bitcoin treasury narrative. Some will call it bad luck. Others will blame macro headwinds. But the truth is simpler: this was never sustainable. It was a high-risk financial structure dressed in the language of conviction, powered by recursive capital raises and investor FOMO.
The data is public. The mechanics are transparent. The outcome is not uncertain. It is mathematically inevitable. What remains is our collective willingness to finally see the 48 billion dollar illusion for what it is: not a visionary bet on Bitcoin, but a self-reinforcing error that mistook leverage for legacy, and market timing for strategy. In the end, Strategy Inc. will not be remembered as a pioneer of digital treasury management. It will be remembered as the cautionary tale of what happens when financial engineering masquerades as principle, and when a company confuses a bull market for a business model.
Additional Notes:
– Reduce digital assets to 49% to stay in the indices
– Sell short-term, hold long-term
– If the biggest treasury fails, the snowball sell effect
– If the biggest treasury fails, what about the rest of the treasuries
– Additional funding
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