Dave Portnoy has had a lot of success — and some bumps in the road — when building his financial empire.
Portnoy founded Barstool Sports in 2003 as a weekly print publication. One year after forming the company, Portnoy filed for bankruptcy protection in 2004 after large gambling losses, per The New York Times.
Years later, Barstool Sports expanded online and ceased its print operation in 2010. After focusing primarily on the digital aspect, Portnoy saw growth in his company and earned investments from multiple equity firms including The Chernin Group.
In 2020, Penn National Gaming purchased 36 percent of Barstool Sports for $163 million in a mix of cash and stocks. Three years later, the company bought the rest of the network for $388 million.
Six months after fully acquiring Barstool Sports, Penn National Gaming decided to part ways with the brand. Portnoy subsequently bought back the company for $1. After becoming sole owner, Portnoy vowed he’d never sell again.
“For the first time in forever, we don’t have to watch what we say, how we talk, what we do. It’s back to the pirate ship,” he said in an August 2023 YouTube video. “By the way, I’m never going to sell Barstool Sports. Ever.”
Keep scrolling to see what Portnoy has said about money over the years:
Providing Relief
Amid the COVID-19 pandemic, Portnoy established the Barstool Fund to help restaurants and small businesses financially recover. The CEO put in $500,000 of his own money for the effort.
“I don’t care how I get the money. If I need to raise more money, if I have to pay it myself, whatever it is I’ll get creative,” he explained in a December 2020 video uploaded via X. “But once you’re in our program we will pay whatever you need.”
Selling Barstool
During a March 2023 appearance on Logan Paul’s “Impaulsive” podcast, Portnoy claimed he made $100 million by selling Barstool Sports and he distributed the wealth to his colleagues.
“We’ve sold twice,” Portnoy recalled. “The first time, I took my equity and I gave away about 15 percent of it to my early guys so they had equity.”
Investing in Athletics
Portnoy, who is a Michigan alum, joked that he would gladly pitch in to get his alma mater’s football team an elite quarterback.
“Michigan, I will be your quarterback guy … I will sign them $1 million, $2 million, $3 million — whatever it is,” he said during a September 2024 appearance on Barstool Pickem. “I can get a quarterback, we don’t have a quarterback.”
Giving His Ex-Wife Full Access
Portnoy made headlines in December 2024 when he confessed that his ex-wife, Renee, still had access to his money despite being separated since 2017.
“We met when Barstool was nothing, so she rode the grind up with us,” he said on the “The Sage Steele Show” podcast. “Still, currently, basically she has access to all my money. If she just wanted to be like, ‘I’m taking it and gone,’ she could.”
Portnoy explained that he and his ex were still technically married since the state of Massachusetts denied their divorce due their financial situation.
“Her and I have a very fluid relationship with our finances,” he continued. “She’s not like, ‘Give me half,’ and we’ve been separated legally for a long time. The judge said our agreement wasn’t equitable to her. They’re like, ‘He’s worth a lot more you have to give half.’”
A Charitable Offer
While visiting a local pizza shop in Baltimore, Portnoy was inspired to donate $60,000 to the TinyBrickOven pizzeria so it could keep its doors open a little bit longer.
“That’s the number, you’ll have it before Christmas,” Portnoy said to the shop owner in a December 2024 Instagram video. “It should keep you open for a year … the pizza was good too.”
What He Pays His Employees
Portnoy got candid about how much Barstool personalities make after Grace O’Malley parted ways with the company. In a January 2025 TikTok video, Portnoy revealed O’Malley’s base salary was $175,000 with the chance to earn more.
“She got another $75,000 in 2024 that way,” he said. “[Her interview] could have been cut up, misconstrued a little bit, but it does bother me when people make it seem like they’re not getting paid fairly. I think we treated — as I’ve said from the beginning — Grace great.”
Portnoy also explained that once Barstool makes back the personality’s base salary, they “split every dollar fifty-fifty” going forward.
“I just don’t like it when people make it seem like we scam our creators, because we f***ing don’t,” he added.
Tariffs Trouble
After new tariffs were put in place in the United States in April 2025, Portnoy admitted he already took a financial beating due to the stock market decline.
“I went super viral when I said I lost $7 million,” Portnoy said during an episode of his “Davey Day Trader” livestream referring to his comments three days prior. “I’d kill to be back to losing $7 million.”
While $7 million seemed like a lot, the social media personality confessed the loss was actually a lot worse than that amount. Portnoy speculated his net worth — which has been estimated at $150 million — had gone down by 10 to 15 percent.
“If I had to guess, I’m down in these last three days probably close to [$20 million],” he claimed.
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