“Well, well, well, how the turntables…”

For as long as I can remember, Michael Saylor has been crypto’s most dependable cult leader. Not in a bad way… more like the guy handing out pamphlets titled “Have You Heard the Good News About Bitcoin?” while maintaining unblinking eye contact.

When Bitcoin ripped, his strategy (capital S, trademark pending) became gospel. Borrow money, buy BTC, repeat. The faithful were rewarded, doubt was heresy, and Saylor preached conviction with the confidence of someone who’d already seen the ending. But lately, the congregation is whispering… or should I say shouting?

(Source: Investopedia)

As 2025 limps toward the finish line with Bitcoin stuck below $90,000, the crypto community has gone from “trust the process” to “who let this man borrow the credit card?” And even more folks are floating the question: “does this dude have a clue what he’s even doing?”

For context, Strategy built a self-feeding machine powered entirely by Bitcoin momentum. Issue debt, buy BTC, let rising prices justify the next round. During the upswing, the flywheel spun effortlessly. MSTR became the cleanest way to turn conviction into volatility.

Now the machine is slowing. MSTR is down roughly 60% from its summer highs, underperforming Bitcoin and trading close to the actual value of the coins it holds. That premium everyone loved? Gone. The “visionary” label? Being replaced with words like “overleveraged” and “refinancing risk.” 

And Michael might want to think about disabling comments on his next “you guys are all peasants, I’m a genius” post because social media sentiment has turned into open-season mockery.

And it’s not hard to see why nerves are fraying.

Strategy has stacked years of convertible debt and financing obligations to build its Bitcoin war chest. That leverage cuts both ways. When prices rise, it’s a rocket ship. When prices chop sideways for months, it turns into a very expensive waiting room. 

Then all you have to do is take a look at the numbers. Strategy is staring at roughly $824 million a year in interest and dividend payments, while its actual software business doesn’t throw off enough free cash flow to cover the bill. Bitcoin, famously, does not send quarterly checks (aka dividend checks).

To calm the mob, Strategy recently padded its cash reserves to about $2.19 billion, raised fresh equity, paused Bitcoin purchases, and set aside a $1.4 billion buffer for future payments. Translation: they’re battening down the hatches for a long winter. The market noticed… and not in a reassuring way.

But here’s where crypto gets weirdly familiar.

Historically, this kind of all-out negativity tends to show up near turning points. When sentiment goes full doom mode, when the memes turn cruel and even true believers start questioning the trade, a lot of the weak hands have already left the building. Selling pressure dries up not because things are good, but because everyone who wanted out already hit the exit.

That doesn’t mean Bitcoin is gonna bounce tomorrow and absolutely doesn’t mean Saylor “wins” the argument on a neat timeline. That said, the current hate parade might say more about exhaustion than collapse. Because literally every time we see Bitcoin underperform for a hot minute, it always seems to bounce back… especially when twitter bros start calling Michael Saylor a fraud.

At the time of publishing this article, Stocks.News holds positions in Strategy, Bitcoin, and Ethereum as mentioned in the article.