Barstool Sports founder Dave Portnoy says his latest Bitcoin wager has turned into an expensive lesson in timing — but he’s not throwing in the towel.
On Fox Business’ Varney & Co., Portnoy admitted he bought Bitcoin “at $100,000” and is now “losing millions,” yet insisted he won’t sell. “There’s nothing I’ve been wrong about more than Bitcoin,” he said. “Every time I sell it, it goes nuclear. Every time I buy it, it tanks.” He added bluntly, “I’m holding, I’ll hold this thing down to zero,” acknowledging that dumping now would likely mean missing any rebound.
Portnoy expanded on his on-again, off-again Bitcoin history on The Pomp Podcast, recalling an earlier trade in which he purchased roughly $2 million of BTC around $11,000 after a chat with Cameron and Tyler Winklevoss — only to sell almost immediately because he didn’t understand their long-term thesis. That exit proved costly as Bitcoin later surged, prompting him to re-enter the market at much higher prices.
Despite the losses and his own admitted difficulty predicting crypto moves — “I don't know what the hell's going on with it,” he told Pomp — Portnoy is sticking with the position. His candid remarks underscore a broader theme: the crypto market’s volatility spares few, including high-profile retail investors who have seen gains evaporate and reappear.
Portnoy’s comments came amid wider conversation around crypto policy and markets. Fox Business segments alongside his interview referenced pro-crypto voices in Washington — including Larry Kudlow and former SEC official Paul Atkins — and noted ongoing legislative and regulatory debates, such as GOP proposals to codify a strategic Bitcoin reserve. Other coverage cited in the segment included recent headlines about large crypto holdings disclosed by political figures.
Bottom line: Portnoy’s experience highlights both the emotional roller coaster and the stubborn hold thesis some investors maintain. He’s out millions on paper today, but for now he’s choosing conviction over cutting losses.
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