Barstool’s Portnoy Refuses to Sell Bitcoin, Even if It Falls to Zero

Bitcoin News: Barstool Sports founder Dave Portnoy said he is sitting on millions in paper losses after buying bitcoin near $100,000, adding that he plans to hold the position even if it drops to zero rather than risk selling before another rally.

Speaking on Varney & Co., Portnoy’s comments highlight a recurring pattern in his trading—buying near market highs, exiting too early, and re-entering at higher levels. Bitcoin surged past $126,000 in October 2025 before falling back to around $62,870, putting him roughly 37% below his entry price.

“I’ve got regrets. I bought it at $100,000. There’s nothing I’ve been more wrong about than bitcoin. Every time I sell, it takes off. Every time I buy, it drops,” he said.

Rather than reflecting a valuation-based view, Portnoy’s stance appears rooted in experience. After repeatedly mistiming trades, he is now opting for a hold-through-volatility approach as a form of discipline.

His track record spans multiple cycles and mirrors a common retail pattern. He first entered bitcoin in late 2020 with about $2 million at roughly $11,000 but sold quickly, missing a major rally to $60,000.

He later rebuilt his position at higher prices, with exposure reportedly peaking near $15 million before declining with the market.

In the current cycle, Portnoy said he deployed most of his available capital and averaged down during the downturn, leaving him with significant unrealized losses. His exact holdings remain undisclosed.

The pattern—buying high, selling low, then re-entering higher—helps explain why many retail investors underperform a simple buy-and-hold strategy.

Portnoy’s experience underscores a broader reality: in volatile markets like bitcoin, attempts to time trades often lead to weaker outcomes than staying invested through the cycle.