If there’s one company that has truly mastered the art of turning equity into cryptocurrency, it’s Strategy — formerly known as MicroStrategy. 

Yesterday, the company unveiled its latest gambit: a brand-new $21bn shelf registration to sell common stock via an at-the-market (ATM) offering, having only just burned through the previous $21bn shelf filed in late October 2024. At this rate, the Strategy juggernaut is picking up both momentum and mass and will likely keep doing so for as long as investors are willing to pay a premium to underwrite its crypto crusade. 

And what a crusade it is. Strategy now holds 553,555 bitcoins or 2.64 per cent of total supply, acquired at an average price of $68,459 apiece and currently worth over $53bn. That makes it the undisputed heavyweight champion of corporate bitcoin holders, a title it clearly has no intention of surrendering. 

Why stop now? As long as the market is willing to value Strategy’s shares at more than double the net asset value of its bitcoin stash, executive chair Michael Saylor will keep issuing stock to buy more. It’s a gloriously self-reinforcing loop: every share sold above NAV is, by definition, accretive. The arithmetic is brutally straightforward, and as long as the music plays, Strategy will keep dancing. 

It’s not just common stock, either. Strategy has been merrily tapping the capital markets with convertible bonds and not one but two flavours of preferred stock (dubbed “Strike” and “Strife”) to raise cash to binge on bitcoin. And there’s no reason to think the punchbowl is going away any time soon.

The sheer nerve of Strategy’s pivot — from a dusty enterprise software vendor to a bitcoin-gobbling machine — is frankly astonishing. Since August 2020, when Strategy first decided to bet the farm on crypto, its shares have surged more than 26-fold (that’s not a typo), even though its actual cumulative gain from its bitcoin investments is only 41 per cent. 

The world-beating stock price performance is not just a rerating; it’s a metamorphosis of almost cartoonish proportions. Some may scoff and say Strategy is little more than a leveraged bitcoin ETF wrapped in a corporate disguise, with a capital structure that subordinates the interests of its common stockholders, but try telling that to investors who’ve been surfing this wave since the beginning.

Of course, all of this financial engineering hinges on two rather large conditions: that bitcoin’s price stays elevated, and that the market continues to bless Strategy’s shares with a generous premium. The two are linked, of course — but should either falter, the virtuous loop could unravel with uncomfortable speed.

Whether this all amounts to genius or lunacy rather depends on your opinion of bitcoin itself. But whatever your take, the sheer chutzpah is undeniable. In the grand history of financial reinvention, Strategy’s transformation ranks among the most audacious — and, so far at least, one of the most lucrative. 

Just don’t ask what happens if bitcoin tanks, the premium evaporates, and Strategy has to rustle up cash to redeem that $1bn convertible bond due in 2028 (with an investor put option in September 2027). The company reported only $60.3mn of cash on its balance sheet at the end of the first quarter of 2025.

For now, though, with bitcoin flirting with $97,000 and investor appetite for Strategy’s stock showing no signs of waning, Strategy’s strategy is working. Investors keep betting on bitcoin as a hedge against dollar debasement and keep paying a hefty premium to access the Saylor spectacular.

Further reading:
— If bitcoin is the future, what explains MicroStrategy’s need for speed? (FTAV)
— MicroStrategy’s secret sauce is volatility, not bitcoin (FTAV)
— Examining MicroStrategy’s record-shattering $21bn ATM (FTAV)
— Buy higher, pump harder (FTAV)
— The trouble with strife (FTAV)