Barstool Sports founder Dave Portnoy announced this week that he will hold his bitcoin position all the way down to zero after purchasing near $100,000. According to reports from FOX Business, Portnoy told Stuart Varney on Varney & Co. that he is "holding. I'll hold this thing down to zero." He explained his rationale, stating "I know if I sell it, it's going to go nuclear again. I'd rather go down with the ship this time." Portnoy's exact bitcoin holdings remain undisclosed to the public, but his latest entry near the $100,000 level puts his unrealized loss at roughly 37% from cost basis, with the peak-to-trough drawdown from his buy point exceeding $60,000 per coin. As per 99Bitcoins, Bitcoin is currently trading at $61,600, roughly 37% below Portnoy's entry point and about 50% off the cycle peak of $126,000 reached in October 2024.
Portnoy's bitcoin investment has resulted in significant losses, as reported by CoinDesk data. BTC peaked above $126,000 in October 2024 before halving to its current level around $62,870. Portnoy acknowledged his poor timing track record, stating "Every time I sell it, it goes nuclear. Every time I buy it, it tanks." He noted that "there's nothing I've been wrong about more than Bitcoin" and expressed regret over his $100,000 purchase decision. His history with Bitcoin reads as a case study in retail FOMO compounding, with his first entry in late 2020 at around $11,000, followed by immediate selling that would have returned roughly 6x had he held through BTC's early 2021 run to $60,000. As per 99Bitcoins, Bitcoin began the week trading at around $61,600, up 1.8% on the day, with the leading digital asset continuing to hold above $60,000, sparking belief that a run toward $70,000 is on the way in Q3.
Portnoy's latest cycle repeated the same pattern at a higher dollar magnitude, with his peak Bitcoin position reportedly reaching around $15 million before market declines cut that substantially. He has publicly stated he exhausted most of his available cash, averaging down through the drawdown, and his BTC losses now run into the millions on an unrealized basis. The pattern of buy high, capitulate, re-enter higher is precisely what distinguishes retail investors who underperform a simple buy-and-hold strategy across cycles. Research consistently shows that retail investors who attempt to time entries and exits in volatile assets like Bitcoin generate returns well below passive holders over equivalent periods. As recently as late June 2024, he said he would consider deploying $5–10M of Barstool corporate funds into Bitcoin if the price fell to $40,000, while explicitly declining to buy at $60,000, as reported by 99Bitcoins.
Portnoy's commitment to hold to zero represents a behavioral rather than analytical decision, as he is not making a valuation case for Bitcoin but reacting to his personal track record of selling before every major rally. His self-diagnosis is unusually blunt for a public figure with a position still on the books, with the logic being behavioral rather than analytical. The risks that accompany prominent Bitcoin holders who buy in size and then face sustained drawdowns are not unique to Portnoy, but his public commentary makes the behavioral traps unusually visible. The uncomfortable truth his story illustrates is that market timing is reliably destructive for most participants, not just celebrities. Portnoy's public losses, broadcast in real time across FOX Business and social media, underscore a lesson that takes most traders years to learn: entry-price discipline and an exit strategy matter more than conviction in the asset itself. Whether his new holding strategy will align with bitcoin's trajectory over coming cycles remains uncertain, but his candor about the challenges of market timing highlights a lesson many retail investors learn the hard way.
