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Barstool’s Dave Portnoy Doubles Down on Bitcoin, Despite Track Record of Missed Calls

Barstool Sports founder Dave Portnoy said he is willing to hold his bitcoin position all the way to zero after buying near the $100,000 level.

Speaking this week, Portnoy admitted he has repeatedly struggled to time the market and now plans to stay invested regardless of further downside.

“I’m holding. I’ll hold this thing to zero,” he said on FOX Business’ Varney & Co. “Every time I sell, it takes off. I’d rather stick with it this time, even if it sinks.”

Portnoy said he bought bitcoin around $100,000 and is currently facing losses in the millions. The cryptocurrency previously climbed above $126,000 in October before dropping to about $63,000, according to CoinDesk data.

“I have regrets. I bought it at $100,000. There’s nothing I’ve been more wrong about than bitcoin,” he said. “Whenever I sell, it rallies. Whenever I buy, it falls.” His exact holdings are not publicly disclosed.

His comments reflect a broader challenge in volatile markets: the difficulty of consistently timing entry and exit points. Many traders end up selling ahead of rallies and buying before pullbacks, leaving them on the wrong side of market moves.

While it remains unclear whether his decision to hold will align with bitcoin’s long-term direction, Portnoy’s remarks underscore a common lesson for retail investors: attempting to time the market often proves more costly than simply holding through cycles.