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The founder of Barstool Sports, Dave Portnoy, recently shared with Anthony Pompliano that at one point he owned $15 million in Bitcoin but ended up losing most of it. Surprisingly, he still chooses not to sell.
Portnoy says he always gets the wrong idea about Bitcoin
During his conversation with Pompliano, Portnoy recounted how he first got involved with cryptocurrencies. He mentioned a meeting with the Winklevoss twins, who sold him Bitcoin for $11,000.
He initially invested $2 million, sold it off almost immediately, and sought clarification from them. Portnoy remarked that, at one point, Bitcoin skyrocketed from $11,000 to $60,000 in just about six months.
He later jumped back in at a much higher price, ultimately accumulating a Bitcoin position worth around $15 million at its peak.
“I’m not going to sell it,” Portnoy stated. “You could go to zero, and you could lose millions.” He mentioned that while the position is significant enough to check daily, it doesn’t constitute a big part of his overall net worth to change his lifestyle or behavior.
Portnoy still doesn’t understand Bitcoin and doesn’t pretend to understand it
Portnoy admitted that he ventured into meme coins during the last crypto cycle, calling it one of the wildest experiences in his two decades at Barstool Sports.
At one point, he even pulled out a coin named Safe Moon on camera, expressing skepticism about it being a scam, yet found himself the subject of a lawsuit alongside other influencers accused of hype promotion.
He faced financial losses and had to hire a lawyer before ultimately being dismissed from the case.
In the prevailing market, Portnoy feels there are no advantages. “You made Saylor sell by telling him he was happy to sell. Who knows?” he said, referring to recent Bitcoin sales by Strategies Co., Ltd.
He shared that his stock portfolio is intentionally conservative and overseen by a broker, mentioning that the only speculative element remains his Bitcoin investment.
From $2 million failed trade to $15 million position: Portnoy Bitcoin complete timeline
If he’d held onto that $2 million investment made at the end of 2020 for $11,000, it would have valued around $12 million when Bitcoin hit $60,000 just six months later.
Portnoy made several returns at increasing highs over the years, ultimately curating a peak position worth around $15 million before suffering notable losses.




