Bitcoin News: Barstool Sports founder Dave Portnoy said he is facing millions in unrealized losses after buying bitcoin near the $100,000 level, adding that he now plans to hold the position even if it falls to zero rather than risk mistiming the market again.

Speaking on Varney & Co., Portnoy’s remarks underscore a familiar pattern in his trading—buying at elevated levels, selling prematurely, and re-entering at higher prices. Bitcoin climbed above $126,000 in October 2025 before retreating to around $62,870, leaving him down roughly 37% from his entry.

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

His stance reflects a behavioral shift rather than a valuation-driven view. Instead of arguing fundamentals, Portnoy is responding to repeated timing errors by adopting a hold-through-volatility approach.

His history with bitcoin mirrors a broader retail investing trend. He initially entered the market in late 2020 with about $2 million at roughly $11,000 but exited quickly, missing a potential sixfold gain as prices surged to $60,000 in early 2021.

He later rebuilt his exposure at higher levels, with his position reportedly peaking near $15 million before market declines eroded its value.

In the current cycle, Portnoy said he committed most of his available capital and averaged down during the downturn, resulting in significant paper losses. His exact bitcoin holdings remain undisclosed.

The repeated cycle of buying high, selling low, and re-entering at higher prices highlights why many retail traders underperform a simple buy-and-hold strategy.

Portnoy’s experience reinforces a broader market lesson: in highly volatile assets like bitcoin, attempts to time entry and exit points often lead to weaker outcomes than long-term holding.