Barstool Founder Portnoy Loses Millions on Bitcoin but Vows Not to Sell

Dave Portnoy, founder of sports media company Barstool Sports and jokingly described on social media as a contrarian crypto indicator, has had a turbulent history investing in Bitcoin. He has often sold at a loss during price crashes, only to see Bitcoin surge immediately afterward. His experience highlights the psychological pressures retail investors face in cryptocurrency markets and the influence of celebrity investors, making it a notable gauge of crypto investment sentiment.

Portnoy disclosed in July 2026 that he had bought Bitcoin when its price was approaching a peak of $100,000, leaving him with several million dollars in unrealized losses. Despite the steep decline in the value of his holdings, he said publicly that he was prepared for the investment to fall to zero and would not sell, fearing the price would rebound immediately after he cut his losses.