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Dave Portnoy’s Financial Ventures: From Bankruptcy to Barstool Sports Buyback
Dave Portnoy, the founder of Barstool Sports, has navigated a dynamic financial trajectory, marked by both significant triumphs and considerable setbacks. This article examines key moments in his business dealings, from early financial losses to the subsequent growth and strategic transactions involving his media empire.
Early Career and Financial Challenges
Portnoy established Barstool Sports in 2003, initially as a weekly print publication focused on sports and gambling content. However, the nascent stages of his entrepreneurial journey included financial adversity. According to reports from The New York Times, Portnoy faced substantial gambling losses and filed for bankruptcy protection in 2004, just a year after launching his company.
Digital Expansion and Investment
Barstool Sports transitioned to a primarily online platform in 2010, ceasing its print operations. This pivot to digital media proved transformative, leading to significant expansion and attracting substantial investments. The company garnered financial backing from various equity firms, notably including The Chernin Group, fueling further growth and brand development.
Acquisition and Reacquisition of Barstool Sports
In a major deal in 2020, Penn National Gaming acquired a 36 percent stake in Barstool Sports for $163 million, in a combination of cash and stock. This initial investment was followed by a full acquisition three years later, with Penn National Gaming purchasing the remaining portion of the company for $388 million. However, the partnership was short-lived. Just six months after completing the full acquisition, Penn National Gaming opted to divest from Barstool Sports, selling the brand back to Portnoy for a nominal sum of $1.
Upon regaining sole ownership in August 2023, Portnoy declared his renewed independence and long-term commitment to Barstool Sports. “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 stated in a YouTube video. He further asserted, “By the way, I’m never going to sell Barstool Sports. Ever.”
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Portnoy’s Philanthropic and Business Perspectives
Charitable Initiatives: The Barstool Fund
During the COVID-19 pandemic, Portnoy launched the Barstool Fund, a philanthropic endeavor aimed at providing financial assistance to restaurants and small businesses struggling due to pandemic-related restrictions. Portnoy personally contributed $500,000 as seed money for the fund.
“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,” Portnoy affirmed in a December 2020 video shared on X. “But once you’re in our program we will pay whatever you need.”
Insights on Selling Barstool Sports
In a March 2023 appearance on Logan Paul’s “Impaulsive” podcast, Portnoy discussed the financial outcomes of selling Barstool Sports. He stated that he personally made $100 million from the sales and distributed a portion of this wealth to early employees.
“We’ve sold twice,” Portnoy recounted. “The first time, I took my equity and I gave away about 15 percent of it to my early guys so they had equity.”
Investment in College Athletics
An alumnus of the University of Michigan, Portnoy has publicly expressed interest in financially supporting his alma mater’s football program, particularly in securing top-tier quarterbacks. He jokingly suggested a willingness to invest significantly in attracting talent.
“Michigan, I will be your quarterback guy … I will sign them $1 million, $2 million, $3 million — whatever it is,” he remarked during a September 2024 appearance on Barstool Pickem. “I can get a quarterback, we don’t have a quarterback.”
Financial Relationship with Ex-Wife
Portnoy drew attention in December 2024 when he revealed that his former wife, Renee, maintained access to his finances despite their separation since 2017. He explained the unconventional arrangement on “The Sage Steele Show” podcast.
“We met when Barstool was nothing, so she rode the grind up with us,” he explained. “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 clarified that their divorce proceedings in Massachusetts were complicated due to their financial circumstances. “Her and I have a very fluid relationship with our finances,” he added. “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.’”
Charitable Donation to Local Business
During a visit to a pizzeria in Baltimore, Portnoy was moved to provide financial assistance to TinyBrickOven pizzeria, donating $60,000 to support its operations.
“That’s the number, you’ll have it before Christmas,” Portnoy told the shop owner in a December 2024 Instagram video. “It should keep you open for a year … the pizza was good too.”
Employee Compensation at Barstool Sports
Following the departure of Grace O’Malley from Barstool Sports, Portnoy discussed employee compensation practices within the company. In a January 2025 TikTok video, he disclosed O’Malley’s base salary as $175,000, with opportunities for additional earnings.
“She got another $75,000 in 2024 that way,” he stated. “[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 further detailed the revenue-sharing model at Barstool, explaining, “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 asserted.
Impact of New Tariffs on Finances
In the wake of new tariffs implemented in the United States in April 2025, Portnoy acknowledged experiencing financial repercussions due to declines in the stock market. He referenced a previous statement about significant financial losses.
“I went super viral when I said I lost $7 million,” Portnoy mentioned during an episode of his “Davey Day Trader” livestream, referring to comments made three days prior. “I’d kill to be back to losing $7 million.”
While initially citing a $7 million loss, Portnoy indicated the actual financial impact was considerably more substantial. He speculated that his estimated net worth of $150 million had decreased by approximately 10 to 15 percent.
“If I had to guess, I’m down in these last three days probably close to [$20 million],” he estimated.