In late 2023, the Financial Times ran its annual stock-picking competition — an exercise more rooted in editorial camaraderie than rigorous financial modelling. One columnist, certain that MicroStrategy’s eccentric Bitcoin gamble had run its course, listed it as a short. It was a decision that would see them finish near the bottom of over a thousand participants. Strategy’s shares rose almost 400 per cent in 2024, outperforming tech titans and confounding expectations. The joke, it turned out, was on the FT.

MicroStrategy, now renamed Strategy, no longer pretends to be a software firm in the conventional sense. Its founder and chairman, Michael Saylor, has transformed it into the world’s largest publicly traded proxy for Bitcoin — a listed company whose primary function is to buy, hold, and trumpet the virtues of a single digital asset. As of early 2025, it holds over $50bn in Bitcoin, making it the largest corporate owner globally.

What distinguishes Strategy is not just its exposure to Bitcoin, but how it has financed that exposure. Since 2020, it has employed a range of financial instruments — share issuance, convertible bonds, and more recently, perpetual preferred stock — to raise capital and purchase more Bitcoin. As its share price has soared, so too has its ability to raise further funds. The result is a kind of corporate reflexivity: investor enthusiasm for Bitcoin raises Strategy’s share price, which enables it to issue more equity at a premium and acquire even more Bitcoin, which then feeds back into the enthusiasm. It is this self-reinforcing mechanism that some in the market have begun calling the “infinite money glitch.”

In practice, Strategy can, when trading at a substantial premium to its net asset value, effectively buy Bitcoin at a discount. A share issuance at double NAV allows the company to acquire $1 of Bitcoin for 50 cents — a feat that dilutes shareholders in theory, but adds to the company’s Bitcoin per share in practice. In most cases, such financial engineering would be cause for alarm. In Strategy’s case, it has become a selling point.

This has attracted a particular kind of investor. Strategy’s shareholder base increasingly resembles a community of true believers rather than portfolio managers assessing discounted cash flow models. Michael Saylor is treated less as a CEO and more as a philosopher-king, dispensing Bitcoin gospel on social media, complete with AI-generated imagery of himself clad in digital armour. For some, it is theatre. For others, it is conviction.

And yet, the company’s mechanics are not entirely irrational. Institutions, often wary of hype-driven equities, have participated in Strategy’s bond offerings. Hedge funds have found arbitrage opportunities between the convertible debt and the common stock. The perpetual preferred shares, launched in 2025 under tickers like STRK and STRF, cater to more conservative appetites — a sign of Strategy’s attempts to broaden its investor base.

Still, the business model remains deeply exposed to the price of Bitcoin. During a sell-off triggered by fears of a global trade war in early 2025, Bitcoin dropped sharply. Strategy reported nearly $6bn in unrealised losses that quarter. Although the company’s debt maturities are staggered and interest obligations minimal, its liquidity remains thin. If the Bitcoin price were to fall and stay depressed, Strategy’s ability to service obligations without selling assets — or diluting shareholders further — would come under pressure.

There is also the question of regulatory risk. While Saylor promotes Bitcoin with zeal, he is careful not to directly hype his company’s stock — a fine but important legal distinction. Strategy’s reliance on financial engineering, premium arbitrage, and investor sentiment is not illegal. But it is delicate. The SEC’s past interest in Saylor — including a 2000 accounting settlement involving no admission of wrongdoing — is a reminder that attention cuts both ways.

For now, Strategy thrives in a financial environment increasingly shaped by narrative, momentum, and meme dynamics. It has built a business not just on belief in Bitcoin, but on belief in the belief of Bitcoin — a subtle but powerful distinction.

Whether this model is sustainable remains to be seen. The infinite money glitch works, until it doesn’t. But while it does, it has turned a once-obscure software company into a $100bn enterprise, defied a sceptical press, and left a trail of short sellers reconsidering their assumptions.

Even at the FT.