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Industry

“I’ve Got Regrets”: Dave Portnoy Says He’s Down Millions on Bitcoin

Despite the losses, Portney said he has no plans to sell, arguing that every time he exits Bitcoin, its price eventually surges.

Written By Iyiola Adrian Iyiola Adrian
Edited by Shubham Soni Shubham Soni
Published 1 hour ago
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Key Highlights

  • Dave Portnoy revealed that he is down millions of dollars after buying Bitcoin near the $100,000 price level.
  • Despite the losses, Portnoy said he has no plans to sell because he believes Bitcoin could rebound.
  • Portnoy also questioned Bitcoin supporters on X, asking them to explain why they still believe the asset could reach $1 million.

Barstool Sports founder and media personality Dave Portnoy said he is down millions of dollars on his Bitcoin investment after buying the cryptocurrency near its recent high.

Speaking during an interview with Fox Business host Stuart Varney on “Varney & Co.” on Friday, Portnoy said he bought Bitcoin at around $100,000 before its price declined sharply from its all-time high of $126,080 to about $62,162, leaving him with significant unrealized losses.

Portnoy admits costly Bitcoin bet

Portnoy said the fall hit his portfolio hard and admitted that his timing has been wrong many times. He said he is not a professional crypto trader and has never claimed to fully understand the market, but he has still kept trying to trade it over the years. “Yeah, I’ve got regrets,” and also added, “I bought the thing at $100,000, so I mean, right now, I don’t know what’s going on.” He openly said. 

He also spoke about a pattern he has noticed in his trading. According to him, whenever he buys Bitcoin, the price tends to fall, and whenever he sells, it tends to rise sharply. He said, “There’s nothing I’ve been wrong about more than Bitcoin. Every time I sell it, it goes nuclear. Every time I buy it, it tanks.” This shows how he feels stuck in a cycle of bad timing and missed chances.

Why he’s still holding Bitcoin

Still, Portnoy said he is not planning to sell his Bitcoin right now. Instead, he said he will continue to hold it no matter what happens next. He stated, “I’m just holding. I’ll just hold this thing down to $0,” and added that he believes selling now could lead to regret if the price rises again later. 

He said, “I know if I sell it, it’s going to go nuclear again.” For him, holding has become a way to avoid repeating past mistakes.

Questioning Bitcoin supporters during market dip

Earlier this week, Portnoy took to X to challenge strong Bitcoin supporters during another market dip. As Bitcoin fell below the $60,000 level, he questioned long-term price predictions. 

He said, “I need all the bitcoin and crypto people who say it’s going to a million and how it’s the future to tell me why all the people who have always said it’s a scam and going to zero are wrong,” adding, “Cause it seems like it’s going to zero.” 

At the time of his post, Bitcoin was trading around $59,564.

A long history of crypto trades

Portnoy’s history with Bitcoin goes back several years. At one point, he bought around $2 million worth of Bitcoin when it was priced near $11,000 after speaking with Cameron and Tyler Winklevoss.

But he quickly sold it after a small drop because he was unsure about it. That decision later cost him a huge gain when Bitcoin’s price surged. He later re-entered the market during the 2020–2021 crypto boom, but again at much higher prices.

Over time, he has also traded other crypto assets, including XRP, as well as meme coins like SafeMoon and Solana-based tokens. He has also been involved in online crypto communities such as the “Link Marines,” who support Chainlink. At one point, he promoted a meme coin called JAILSTOOL, which rose quickly in value before crashing heavily later.

His trading history reflects an active but volatile approach to cryptocurrency investing, marked by both sizable gains and significant losses.

Also Read: Michael Saylor’s Secret Sell-Off? Unconfirmed 491 Bitcoin Sell Sparks Panic

Disclaimer: The information researched and reported by The Crypto Times is for informational purposes only and is not a substitute for professional financial advice. Investing in crypto assets involves significant risk due to market volatility. Always Do Your Own Research (DYOR) and consult with a qualified Financial Advisor before making any investment decisions.

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TAGGED:Bitcoin (BTC)
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Iyiola Adrian
By Iyiola Adrian
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Iyiola Adrian is a Crypto Analyst at The Crypto Times, based in Lagos, Nigeria. He covers daily cryptocurrency market developments, including Bitcoin and Ethereum price action, altcoin movements, on-chain trends, and fact-check reports on circulating market claims. His analysis emphasizes how African and emerging-market investor behavior interacts with global crypto flows. Before joining The Crypto Times, Iyiola was a contributor at CoinCodex, where he focused on long-form crypto analysis, project reviews, and biographical research on industry figures. He has been writing on digital asset markets continuously since 2022, and his expertise spans market research, chart pattern analysis, technical indicators, and fundamental valuation across the crypto sector. Iyiola holds a Bachelor's degree in Civil Engineering from the Federal University Oye-Ekiti, Nigeria, and is currently pursuing a Master's in Business Administration at Afe Babalola University, Nigeria.
Shubham Soni
By Shubham Soni
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Shubham Soni is the Editor at The Crypto Times, based in Ujjain, Madhya Pradesh. He oversees the editorial desk, reviewing daily news coverage of cryptocurrency markets, US and Indian regulation, institutional adoption, the Solana ecosystem, AI agents, and Real World Assets (RWAs). All policy and markets coverage at The Crypto Times passes through his desk before publication. Before joining The Crypto Times in October 2025, Shubham managed news desks at Sportskeeda and Opoyi, covering global politics, sports, and entertainment for high-volume newsrooms serving the US and Indian markets. His four years in fast-paced newsrooms shaped his approach to fact-checking, source verification, and structural editing on complex stories. Shubham holds a Master's degree in Journalism from Makhanlal Chaturvedi National University of Journalism and Communication (Bhopal) and a Bachelor's degree in Journalism from Amity University Rajasthan. 

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