Veteran fund manager predicts MicroStrategy is headed for bankruptcy

Veteran fund manager predicts MicroStrategy is headed for bankruptcy

At the Bitcoin Conference 2025, legendary Bitcoin critic Peter Schiff found himself in a light-hearted exchange with crypto influencer @LaDoger21, a vocal supporter of Michael Saylor and a self-described Strategy shareholder, Saylor portraitist, and digital artist.

The moment went viral after @LaDoger21 posted a video on X (formerly Twitter), showing a candid confrontation with Schiff, who is well known for his unwavering belief in gold and deep skepticism of Bitcoin.

“Oh my god, guys, I’m with Peter Schiff, the number one Bitcoin bear out there,” the video begins, with @LaDoger21 setting the stage. “Why are you so bear on Bitcoin, Peter?”

Schiff replied bluntly:

“Because I understand it. I know that it’s not worth anything. So I know eventually people are going to figure that out.”

The conversation quickly turned to Saylor’s company, MicroStrategy, which holds one of the largest Bitcoin treasuries in the world.

Schiff is a veteran fund manager, economist, and vocal critic of Bitcoin. He’s best known as the CEO of Euro Pacific Asset Management and a long-time gold advocate. Schiff has consistently argued that Bitcoin has no intrinsic value and is destined to collapse.

“But Strategy stock is like a number one stock in the US,” said @LaDoger21.

“For now,” Schiff retorted. “Actually, it’s not at its highs. I mean it’s well off its peak, so maybe that bubble has popped too, and I think eventually Strategy is going bankrupt.”

Trying to keep things cheeky, @LaDoger21 fired back:

“I think you’re just jealous. I think you’re jealous of Michael Saylor soon becoming a trillionaire, a quadrillionaire.”

Schiff laughed it off and made his own prediction:

“I’ll probably end up richer than Michael Saylor.”

But the Bitcoin supporter wasn’t done yet:

“You’ll be richer in gold, but you’ll not be richer in Bitcoin no matter what. Right? No matter what. You’ll not be richer in terms of Bitcoin. Right?”

Schiff ended the conversation on his terms, throwing one last jab:

“Well, you know what I mean. Eventually he might not have any Bitcoin because I think Strategy is going bankrupt. But I think he’s probably selling Bitcoin. But anyway, I got to go.”

At the time of writing, MicroStrategy (MSTR) was trading at $364.25, down 12.42% over the past five days. The stock is still up 21.41% year-to-date despite recent volatility. In pre-market trading, MSTR was up 1.75% to $370.62.

Veteran fund manager predicts MicroStrategy is headed for bankruptcy first appeared on TheStreet on May 29, 2025

DJ Kamal Mustafa

DJ Kamal Mustafa

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