Barstool Sports founder Dave Portnoy says he doesn't get how wealthy people go broke. Speaking on a recent episode of “The Unnamed Show,” Portnoy said that once someone has real money, it should be easy to keep making more.
“I don’t know how people lose [money],” Portnoy said. “Once you have money, you just make more.”
‘I'm Just Gambling, I'm Just Living’
Portnoy, who estimates his net worth at around $250 million, said he has a finance guy whose only job is to alert him if things ever get tight. “If you’re getting tight, let me know. Other than that, I’m buying horses, I’m buying houses, I’m just gambling, I’m just living,” he said.
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He added that he doesn’t even know what his monthly mortgage payment is on his $42 million Nantucket property.
At one point in the podcast, one of the co-hosts asked if he was worth $700 million. Portnoy laughed off the idea. “No, no. If I had to guess net worth, I’d probably put it around maybe $250 [million]. I don’t know. That’s a guess,” he said. He acknowledged the number is fluid given his various investments, real estate, and gambling activity.
He also took a shot at other celebrities, including Justin Bieber and Bruno Mars, referencing rumors about financial troubles due to excessive spending or gambling. "I don't know if I believe that stuff. How do you spend that much? Like, are you not investing it?"
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Portnoy's own gambling habits have drawn attention not just for their size, but for rumors that he's not always betting his own money but that DraftKings DKNG gives him an annual check to place bets. On the show, he addressed the speculation head-on.
"Anyone who's been with me placing a bet, which you have, [knows] it's my own money," Portnoy said. "I don’t even know that that’s legal, to be totally honest. You’d have to disclaim what’s going on."
He added that he's not a good enough actor to fake the emotional rollercoaster he goes through during high-stakes games. "There's no shot I can have the emotions that I have doing it," he said.
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One Bet Nearly Matches Clark's Salary
Portnoy’s comments came shortly after a high-profile win: he made $325,000 on a single bet predicting Caitlin Clark would record a triple-double in the Indiana Fever's 2025 season opener. He placed a $25,000 wager with DraftKings at +1300 odds.
That one bet nearly matched Clark's four-year WNBA salary of $338,056.
Portnoy has also been vocal about Clark's performance and the media narratives surrounding her. He's criticized outlets like ESPN and public figures for turning a sports rivalry into a race issue. His co-host, Kirk Minihane, made a good point, saying, "This is about two 23-year-old women basketball players. Who gives a sh*t?"
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