Bitcoin News: Dave Portnoy, founder of Barstool Sports, said on Fox Business that he is currently sitting on millions in unrealized losses after buying bitcoin near the $100,000 level, adding that he plans to hold the position even if it falls to zero rather than sell again.
The statement, made during an appearance on Varney & Co., highlights a recurring pattern in Portnoy’s trading behavior: buying near market peaks, exiting before major rallies, and re-entering at higher prices. Bitcoin reached a high above $126,000 in October 2025 before declining to around $62,870, according to CoinDesk data. Based on his entry point, Portnoy is facing an unrealized loss of roughly 37%, with the decline from his purchase price exceeding $60,000 per coin at its lowest point.
Portnoy was candid in his remarks. “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 surges. Every time I buy, it drops,” he said.
His comments reflect a behavioral rather than analytical approach. Instead of making a valuation-driven case for bitcoin, Portnoy appears to be reacting to his own history of mistimed trades. His decision to hold to zero effectively represents a self-imposed discipline after repeatedly failing to time exits successfully.
Portnoy’s history with bitcoin spans multiple market cycles and illustrates a broader retail investing pattern. He first entered the market in late 2020 with about $2 million at roughly $11,000 per coin but exited quickly—missing a potential sixfold gain as bitcoin surged to $60,000 in early 2021.
He later rebuilt his position at higher levels, with his exposure reportedly peaking near $15 million before market declines reduced its value.
In the current cycle, the same pattern has played out at a larger scale. Portnoy has indicated that he deployed most of his available capital and averaged down during the downturn, leaving him with substantial unrealized losses. His exact bitcoin holdings remain undisclosed.
This sequence—buying at elevated prices, selling during declines, and re-entering at higher levels—mirrors the behavior that often causes retail investors to underperform a simple buy-and-hold strategy.
Portnoy’s experience underscores the broader challenge of market timing, particularly in volatile assets like bitcoin. Research consistently shows that investors attempting to actively time entries and exits tend to generate lower returns than long-term holders. While such risks are common among large, high-conviction investors, Portnoy’s public commentary offers a clear view into the behavioral pitfalls that can erode returns over time.Bitcoin News: Dave Portnoy, founder of Barstool Sports, said on Fox Business that he is currently sitting on millions in unrealized losses after buying bitcoin near the $100,000 level, adding that he plans to hold the position even if it falls to zero rather than sell again.
The statement, made during an appearance on Varney & Co., highlights a recurring pattern in Portnoy’s trading behavior: buying near market peaks, exiting before major rallies, and re-entering at higher prices. Bitcoin reached a high above $126,000 in October 2025 before declining to around $62,870, according to CoinDesk data. Based on his entry point, Portnoy is facing an unrealized loss of roughly 37%, with the decline from his purchase price exceeding $60,000 per coin at its lowest point.
Portnoy was candid in his remarks. “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 surges. Every time I buy, it drops,” he said.
His comments reflect a behavioral rather than analytical approach. Instead of making a valuation-driven case for bitcoin, Portnoy appears to be reacting to his own history of mistimed trades. His decision to hold to zero effectively represents a self-imposed discipline after repeatedly failing to time exits successfully.
Portnoy’s history with bitcoin spans multiple market cycles and illustrates a broader retail investing pattern. He first entered the market in late 2020 with about $2 million at roughly $11,000 per coin but exited quickly—missing a potential sixfold gain as bitcoin surged to $60,000 in early 2021.
He later rebuilt his position at higher levels, with his exposure reportedly peaking near $15 million before market declines reduced its value.
In the current cycle, the same pattern has played out at a larger scale. Portnoy has indicated that he deployed most of his available capital and averaged down during the downturn, leaving him with substantial unrealized losses. His exact bitcoin holdings remain undisclosed.
This sequence—buying at elevated prices, selling during declines, and re-entering at higher levels—mirrors the behavior that often causes retail investors to underperform a simple buy-and-hold strategy.
Portnoy’s experience underscores the broader challenge of market timing, particularly in volatile assets like bitcoin. Research consistently shows that investors attempting to actively time entries and exits tend to generate lower returns than long-term holders. While such risks are common among large, high-conviction investors, Portnoy’s public commentary offers a clear view into the behavioral pitfalls that can erode returns over time.
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