Michael Saylor could flood Twitter with bullish Bitcoin posts, hit every podcast circuit known to man, and even sit down with Joe Rogan for a three-hour rant about fiat being a scam, but none of it changes the hard truth. Strategy’s Bitcoin stash is losing value at an insane pace. The company’s unrealized gains have slipped below the $9 billion threshold, and Bitcoin is still struggling to break past resistance at $87K. And what do you know, Peter Schiff is back on his favorite soapbox, claiming Saylor is on a one-way train to bankruptcy.

Since 2020, Saylor has transformed Strategy from a run-of-the-mill software business into a full-blown Bitcoin accumulator, hoarding nearly 500,000 BTC, which amounts to 2.38% of the total supply. The company buys Bitcoin whenever it has cash to spend, no matter the price, with the average cost basis now sitting at $66,000 per coin. This strategy looks brilliant when Bitcoin is flying high, but when prices stall or dip, things get dicey quick.

Peter Schiff, Bitcoin’s loudest critic and gold’s number one fanboy, is enjoying every second of this. On his latest podcast, he laid out why he believes Saylor’s entire strategy is one bad quarter away from imploding. According to Schiff, the only reason Strategy has been able to keep buying Bitcoin is because its stock has been trading at a premium. That premium allowed Saylor to sell shares, raise cash, and funnel it straight into more Bitcoin. But if the stock starts trading at a discount, that whole cycle grinds to a halt. Schiff didn’t hold back, calling Saylor’s so-called Bitcoin yield “fabricated” and warning that if Strategy ever had to sell Bitcoin, it would set off a chain reaction that tanks the price and drags the company down with it.

For now, the illusion is still holding up. Strategy keeps issuing stock and convertible debt, using the proceeds to stack more Bitcoin, while investors continue to treat its shares like a leveraged bet on BTC. The company’s latest financial move (a $21 billion offering of perpetual preferred stock) comes with a strong 9% yield, payable in either cash or more stock. This kind of aggressive financial engineering only works as long as Bitcoin’s price climbs. If BTC stalls or, worse, crashes, Strategy is left holding a ticking time bomb.

The biggest issue hiding in the background is cash flow. Strategy doesn’t actually generate meaningful revenue from its legacy business, meaning all those stock sales and bond offerings are the only things keeping the engine running. If Bitcoin doesn't skyrocket soon, the company could face serious liquidity issues. Schiff argues that Strategy’s creditors don’t care about Bitcoin… they want cold, hard cash. And if the company can’t produce it, things could spiral quickly.

At the moment, Strategy looks strong on the outside. As long as investors keep buying into Saylor’s vision, Strategy can keep pulling financial rabbits out of its hat. But this whole empire depends on two key things: Bitcoin continuing to rise and Strategy’s stock staying at a premium. If either of those conditions break, the consequences could be catastrophic.

For now, Saylor is still on Twitter, still bullish, still acting like nothing can go wrong. But as the numbers start shifting in the wrong direction, you gotta wonder… are things at Strategy HQ as chill as he makes them seem, or are there a bunch of analysts stress-eating Doritos in a conference room, praying to the Bitcoin gods?

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Stock.News does not have positions in companies mentioned.