Dave Portnoy has been wrong about Bitcoin more times than he can count, and he’s done pretending otherwise. The Barstool Sports founder told FOX Business this week that he plans to hold his BTC position “all the way down to zero” after buying near $100,000 and watching the asset shed nearly 40% of its value.
“I know if I sell it, it’s going to go nuclear again,” Portnoy said on Varney & Co. “I’d rather go down with the ship this time.”
The admission is remarkably candid for a media personality who built his brand on bravado. But Portnoy’s frustration reflects something almost every retail investor has felt at some point: the maddening experience of consistently being on the wrong side of volatile markets. His solution, whether by exhaustion or enlightenment, is to simply stop trying.
Portnoy’s $100K Entry and the 50% Drawdown
Bitcoin peaked above $126,000 in October 2025, capping a furious rally that followed the approval of spot ETFs and a pro-crypto shift in Washington. Portnoy apparently bought somewhere around the $100,000 mark, a price that felt like a reasonable entry after months of bullish momentum.
Then came the correction. BTC has since halved, trading around $63,000 as of this weekend. For Portnoy, that translates to a 37% haircut from his entry, and he’s hinted the dollar figure runs into the millions. His exact holdings remain undisclosed.
“Yeah, I got regrets,” he said. “I bought the thing at $100,000. There’s nothing I’ve been wrong about more than Bitcoin.”
The timing couldn’t have been worse. Bitcoin just posted back-to-back quarterly losses for only the third time in its history, with the first half of 2026 down 34%. What looked like an unstoppable run toward $150,000 has instead become a grinding retracement that’s tested even long-term holders.
The Classic Retail Investor Trap
Portnoy’s lament, “every time I sell it, it goes nuclear; every time I buy it, it tanks,” is so common among retail traders that behavioral economists have a name for the phenomenon: disposition effect meets recency bias. Investors tend to sell winners too early (locking in small gains before bigger moves) while holding losers too long (hoping to break even). When they finally capitulate on a losing position, the relief of exiting often coincides with a market bottom.
The result is a pattern where the same person manages to buy high and sell low repeatedly, even when they know better intellectually. Portnoy is just willing to say it out loud.
His experience also highlights the structural disadvantage retail faces against institutional players. Large funds employ quantitative signals, risk management frameworks, and diversified portfolios that smooth out the emotional swings of individual positions. A retail trader watching their net worth fluctuate by millions of dollars in a matter of weeks is fighting biology as much as markets.
The crypto market’s 24/7 trading hours and extreme volatility amplify these pressures. Unlike stocks, where a bad day ends at 4 p.m., Bitcoin can crash 8% while you’re asleep and recover before you wake up. The constant accessibility encourages over-trading, and over-trading almost always destroys returns.
The “Hold to Zero” Strategy: Capitulation or Clarity?
Portnoy’s new approach, holding indefinitely regardless of price, represents a psychological capitulation more than a strategic pivot. He’s not holding because he’s calculated Bitcoin’s long-term value proposition; he’s holding because he’s exhausted from getting it wrong.
“I’ll hold this thing down to zero,” he said. The framing is defeatist on its surface, but there’s an accidental wisdom buried in it.
Research on retail trading outcomes consistently shows that the best performers tend to be the most inactive. A famous Fidelity study reportedly found that its best-performing accounts belonged to investors who had either forgotten they had accounts or were deceased. The point isn’t that death is a trading strategy, but that the instinct to act, to time, to optimize, usually backfires.
Bitcoin specifically has rewarded holders over almost any multi-year time horizon despite brutal drawdowns along the way. From the 2018 crash to 83% below the 2017 peak, from the 2022 collapse below $16,000, from every “death” the asset has supposedly suffered, long-term holders who didn’t sell have outperformed those who tried to trade the swings.
Whether Portnoy’s forced patience will align him with that historical pattern remains to be seen. A lot depends on whether Bitcoin recovers from its current slump or enters a prolonged bear market that tests even the most stubborn holders.
How Deep Could This Drawdown Go?
The current 50% decline from October’s highs is painful but not unprecedented. Bitcoin has historically experienced 70% to 85% drawdowns during major bear cycles. If this correction follows that pattern, prices could theoretically fall to the low $30,000s before bottoming.
That’s not a prediction, just a reminder that Portnoy’s “hold to zero” pledge might face a more severe test than he’s anticipating. At $63,000, his $100,000 entry is underwater by 37%. At $40,000, he’d be down 60%. At $30,000, 70%. The psychological difference between those levels is enormous.
On the other hand, BTC has already reclaimed $63,000 after touching lower levels at the end of June, suggesting the worst of the selling pressure may have passed for now. Volume remains thin in early July, which cuts both ways: thin markets can snap higher quickly, but they’re also vulnerable to sharp drops if selling resumes.
The Fear & Greed Index has been oscillating between fear and extreme fear territory for most of the past quarter, a condition that historically precedes rebounds but can persist for months before sentiment turns.
Portnoy’s Memecoin Warning and Broader Crypto Skepticism
Portnoy’s Bitcoin struggles haven’t made him a blanket crypto believer. Speaking at Consensus 2025, he declared that the memecoin scene is “ultimately unsustainable,” a notable statement given his own history of promoting various internet phenomena to his massive audience.
Memecoins have been one of the few bright spots during the broader market downturn, with tokens tied to political figures, cultural moments, and pure speculation attracting billions in trading volume. But Portnoy appears to view them as a flash-in-the-pan dynamic rather than a lasting market segment.
His skepticism tracks with the lifecycle of most retail crazes in crypto. The memecoin boom of 2021, led by Dogecoin and Shiba Inu, left most late buyers with catastrophic losses when prices collapsed. The 2024-2025 wave, including politically-themed tokens, has followed a similar pattern. According to data referenced by CoinDesk, buyers of Trump’s crypto token are collectively down $3.8 billion.
Portnoy’s willingness to distinguish between Bitcoin (which he’s holding despite losses) and memecoins (which he views as unsustainable) suggests a more nuanced perspective than his self-deprecating comments might indicate. He’s not dismissing crypto entirely; he’s making an implicit argument that Bitcoin’s long-term thesis is more defensible than speculative tokens designed for short-term trading.
What Retail Investors Can Learn From Portnoy’s Candor
There’s something refreshing about a public figure admitting, on national television, that they’ve been repeatedly wrong about an asset class and have no special insight into its future direction. Most pundits prefer to memory-hole their bad calls or reframe them as “early” rather than wrong.
Portnoy’s honesty exposes the reality that market timing is extraordinarily difficult even for people with resources, information access, and financial cushion to absorb mistakes. If a wealthy media entrepreneur can’t time Bitcoin successfully, what chance does the average person have?
The implicit lesson, one Portnoy seems to have internalized through pain, is that time in the market beats timing the market for most participants. This doesn’t mean Bitcoin is guaranteed to recover or that holding blindly is always the right choice. It means that the transaction costs of active trading (both financial and psychological) tend to exceed the benefits for retail investors.
A few practical takeaways from Portnoy’s experience:
- Dollar-cost averaging, buying fixed amounts at regular intervals regardless of price, reduces the risk of making one catastrophically-timed lump-sum purchase.
- Position sizing matters. Portnoy can afford to lose millions on Bitcoin; most people cannot and should size accordingly.
- The assets you can hold through a 50% drawdown are the ones worth owning. If watching a position halve causes you to panic-sell, you were probably overallocated.
- Public commentary from celebrities, including Portnoy himself, is entertainment, not investment advice. His track record proves the point.
Bitcoin’s path from here depends on macroeconomic conditions, regulatory developments, and factors no individual can predict. Portnoy has made peace with that uncertainty by removing his own judgment from the equation. For better or worse, his next Bitcoin trade will be his last: either the asset recovers and he eventually sells at a profit, or it doesn’t and he rides it to zero.
“There’s nothing I’ve been wrong about more than Bitcoin,” Portnoy admitted. Whether that streak continues or finally breaks, he’s decided to stop fighting the tape and let the market deliver its verdict.
