Dave Portnoy, the outspoken founder of Barstool Sports, has publicly committed to maintaining his Bitcoin holdings no matter how far the price falls, even in the event of a complete wipeout. This latest declaration comes amid significant unrealized losses on a recent purchase made near the $100,000 level, as the cryptocurrency has retreated sharply from its prior peaks.
In an appearance on Fox Business’ Varney & Co., Portnoy described his frustration with repeated attempts to time the market.
He noted that his pattern of buying during rallies and selling ahead of recoveries has left him consistently on the wrong side of major moves.
Rather than exit now and risk missing a potential rebound, he has chosen to ride out the volatility, stating he would rather “go down with the ship” than sell prematurely again.
This stance represents a shift toward a more hands-off approach for Portnoy, who has a well-documented history with Bitcoin.
Years earlier, he acquired roughly $2 million worth near $11,000 following discussions with prominent figures in the space.
He exited the position quickly, only to watch the asset surge dramatically in the months that followed.
He later re-entered at higher valuations and built a position that, at its peak, reached approximately $15 million in value before eroding substantially amid recent price weakness.
Bitcoin itself has experienced pronounced swings.
After climbing above $126,000 in October of the previous year, the digital asset has since lost roughly half its value, trading in the low-to-mid $60,000 range in recent sessions.
Portnoy’s latest entry near $100,000 has left him facing multimillion-dollar paper losses, a situation he has described as one of his most consistent missteps in investing.
Portnoy, known for his candid and often humorous commentary on markets through his “Davey Day Trader” content, has embraced a “diamond hands” mentality this time around.
He has indicated that selling now would likely precede another upward surge, based on his past experiences.
By refusing to exit, he is effectively betting on long-term resilience rather than attempting further short-term predictions.
His comments underscore a common challenge for retail participants in highly volatile assets: the difficulty of precise entry and exit timing.
Many investors find themselves buying after significant run-ups or selling before major recoveries, turning potential gains into sources of regret.
Portnoy’s willingness to acknowledge these repeated errors publicly while doubling down on a long-term hold reflects both his personal philosophy and the broader lessons emerging from crypto market cycles.
Whether this approach ultimately proves rewarding will depend on Bitcoin’s future trajectory. For now, Portnoy appears somewhat determined to see the position through to whatever outcome awaits, forgoing active bitcoin and crypto trading in favor of long-term persistence.