Barstool Sports founder Dave Portnoy on Wednesday told Anthony Pompliano he once held $15 million in Bitcoin (CRYPTO: BTC) and has lost most of it. And yet, Portnoy still refuses to sell.

Portnoy Says He’s Always On The Wrong Side Of Bitcoin

In the interview with Pompliano, Portnoy traced his crypto history back to a meeting with the Winklevoss twins, who pitched him on Bitcoin at $11,000. 

He bought $2 million worth and sold immediately after the meeting, calling their explanation about Elon Musk mining gold from outer space nonsensical. Bitcoin went from $11,000 to $60,000 in roughly six months.

He got back in later at much higher prices, eventually building a position worth roughly $15 million at peak. 

“I’m not going to sell it,” Portnoy said. “It may go to zero. I may lose millions again.” He added that while the position is large enough that he checks it daily, it isn’t a material enough portion of his net worth to force a change in behavior.

Portnoy Still Doesn’t Understand Bitcoin And Doesn’t Pretend To

Dave Portnoy said he dabbled in meme coins during the last cycle, calling it one of the craziest experiences of his 20 years at Barstool Sports.

He picked a coin called SafeMoon out of a hat on camera, telling his audience it was probably a scam, and still got named in a lawsuit alongside influencers accused of undisclosed promotions. 

He lost the money and had to hire a lawyer before being dismissed from the case.

On the current market, Portnoy said he has no edge. “You got Saylor selling it saying it’s good that he’s selling it. Who knows?” he said, referencing Strategy Inc.’s (NASDAQ:MSTR) recent Bitcoin sales. 

He said his current stock portfolio is deliberately conservative and managed through a broker, with nothing speculative beyond his Bitcoin position.

From $2M Missed Trade To $15M Position: The Full Portnoy Bitcoin Timeline

The original $2 million buy at $11,000 in late 2020 and immediate sale would have been worth roughly $12 million at Bitcoin’s $60,000 level just six months later. 

Portnoy got back in at various higher prices over the following years, building to a peak position of around $15 million before losses brought it down significantly. 

He declined to give an exact current figure but confirmed the position is substantially smaller than its peak.

Image: Shutterstock