Barstool Sports founder Dave Portnoy has vowed to hold his Bitcoin investment even if it falls to zero after revealing he is down millions on a position bought near $100,000.
According to an interview with Fox Business host Stuart Varney, Portnoy admitted that his history with Bitcoin has been defined by buying at the wrong time and selling before major rallies.
Speaking about his latest position, he said he purchased Bitcoin at around $100,000 and acknowledged that the investment is now deeply underwater after the asset lost more than half its value from its October peak of $126,080 to about $62,162.
Bitcoin and crypto are making me sad.
— Dave Portnoy (@stoolpresidente) June 4, 2026
Instead of exiting the position, Portnoy said he plans to continue holding. He told Varney that previous attempts to sell Bitcoin had repeatedly backfired because the cryptocurrency rallied soon afterward. Having experienced that pattern multiple times, he said he would rather keep the asset regardless of how far the price falls.
Portnoy also described himself as someone who has been consistently wrong on Bitcoin trades. Looking back on earlier market cycles, he recalled panic-selling the cryptocurrency during a price decline in 2021 before it recovered sharply, adding that those experiences shaped his decision not to sell this time.
Bitcoin outlook remains divided
Even as Portnoy remains committed to holding Bitcoin, market participants continue to disagree over where prices could move next.
Earlier this week, as reported by crypto.news, Rich Dad Poor Dad author Robert Kiyosaki’s prediction that Ethereum could reach $95,000 by mid-2027 resurfaced across crypto social media. Kiyosaki argued that a severe global financial crisis could trigger a major repricing of alternative assets.
Under that scenario, he said Ethereum could climb to $95,000 within a year of such an event, while Bitcoin could rise to $750,000 alongside gold reaching $35,000 per ounce and silver advancing to $200.
A day later, Bitwise Chief Investment Officer Matt Hougan wrote that Bitcoin appeared to be entering the final stage of its correction after the STRC-related unwind reduced excess leverage. At the time, he said he expected a new Bitcoin bull market to begin in the fall.
Although he cautioned that identifying the exact bottom is impossible in real time, he said the latest developments suggest the market could be entering the final stage of the current cycle.
Hougan also argued that the next Bitcoin rally is likely to rely less on retail traders and more on institutional investors, including banks, pension funds, sovereign wealth funds, asset managers, financial advisers, and endowments. Based on that view, he said he expects a new Bitcoin bull market to begin in the fall.
Portnoy’s crypto record extends beyond Bitcoin
Beyond Bitcoin, Portnoy has been involved with several high-profile crypto projects over the years. He previously promoted the SafeMoon meme coin and publicly identified himself with the Chainlink community, often referred to as the Link Marines.
His trading activity later expanded into Solana-based meme coins. After revealing his wallet address and facing criticism from some traders who accused him of pumping and dumping tokens, Portnoy publicly embraced JAILSTOOL, a meme coin built around imagery of him behind bars. The token later climbed above a $210 million market capitalization and secured a listing on crypto exchange Kraken. Since then, however, it has lost more than 99.5% of its value and now trades at a market capitalization of just over $1 million.
