I’ve been watching Michael Saylor and MicroStrategy for years, and right now the company is in the most precarious spot it’s ever been in since this whole Bitcoin corporate treasury experiment began.

As I write this on November 23, 2025, Bitcoin has plunged hard in recent weeks, trading down around 25–30% from its most recent all-time high. That’s dragged MicroStrategy’s stock (MSTR) down with it – at one point yesterday the shares were off more than 50% from their peak – because everyone knows the balance sheet is basically one giant leveraged bet on BTC.

Here’s the part that actually matters: the company is not about to implode tomorrow. They’re not FTX. They’re not Celsius. The balance sheet isn’t at immediate risk of collapse the way people are screaming on X. But they are getting uncomfortably close to the line where things start to get very ugly very fast, and the margin of error has shrunk to almost nothing.

Let me break it down the way I see it.

MicroStrategy currently holds roughly 252,000–260,000 BTC (depending on which recent purchase updates you trust). They’ve been buying with a mixture of convertible notes, straight debt, and ATM equity offerings. Almost all of those converts have strike prices well above where the stock is trading right now. That’s the core problem.

When the stock is below the conversion prices (and it is – badly), those noteholders have zero incentive to convert into equity. That means every single one of those debt instruments stays as debt – senior, interest-bearing debt – that eventually has to be repaid or refinanced in cash.

The big maturity wall doesn’t actually hit until late 2027 and 2028 (most of the converts are 0% or 0.625% notes maturing 2027–2031), which is why I keep saying the real test is roughly 18–24 months away, not next quarter. But here’s what changes between now and then if Bitcoin doesn’t recover meaningfully:

1. They lose the ATM equity “free money” machine. They’ve raised tens of billions by continuously selling stock slightly below NAV while the shares traded at a massive premium to the Bitcoin holdings. That spigot just turned off. Hard.

2. Interest coverage starts looking ugly. Even with low coupons, hundreds of millions a year in cash interest is real when software revenue is only covering a fraction of it.

3. Refinancing becomes comically expensive (or impossible) if the stock stays this low and Bitcoin doesn’t rally. Who is going to underwrite another multi-billion-dollar convert when the last five rounds are all underwater?

Saylor’s entire playbook has been: Bitcoin goes up → stock premium expands → issue more cheap debt/equity → buy more Bitcoin → repeat. That flywheel works great on the way up. On the way down it goes in reverse and grinds your face off.

People keep asking me if this is “the end” for MicroStrategy. No, it’s not the end. They could muddle through a prolonged bear market if they just stop buying and hunker down. The software business still throws off some cash, and the debt doesn’t mature tomorrow.

But let’s be crystal clear: if Bitcoin spends the next 18 months bumping around between $60k and $80k, MicroStrategy will be forced into major surgery – massive dilution at terrible prices, asset sales, or some kind of painful restructuring. And if we get a real crypto winter again (sub-$40k), then yeah, things could get existential.

The market is currently pricing in something close to that nightmare scenario, which is why the stock is getting obliterated even though the actual bankruptcy risk is still a ways off.

Bottom line: Saylor’s conviction hasn’t wavered one bit – the guy is still out there tweeting laser-eye memes – but conviction doesn’t pay coupons. The balance sheet is stretched thin, the equity ATM is broken, and the clock is ticking louder than it’s ever ticked before.

We’ll know in the next 18 months whether this was the greatest corporate capital allocation story of all time… or the most spectacular example of over-leveraged hubris in modern market history.

I know which side I’m betting on long term. But that doesn’t mean the next couple of years won’t be absolutely brutal if Bitcoin doesn’t cooperate.

Buckle up.