Dave Portnoy, the outspoken and savvy entrepreneur, has built a net worth of approximately $150 million as of 2025. Best known as the founder of Barstool Sports, Portnoy transformed a small Boston-based print publication into a multimedia empire with millions of fans worldwide. His journey from handing out free newspapers to managing a $550 million business is a testament to his business acumen and unapologetically bold personality. Here’s a closer look at how Dave Portnoy made his fortune and what he does with it today.
Early Life and the Birth of Barstool Sports
David Portnoy was born on March 22, 1977, in Swampscott, Massachusetts. He attended the University of Michigan, where he graduated with a degree in education. However, his passion lay in sports and gambling, which led him to launch Barstool Sports in 2003 as a free four-page print publication in Boston. Focused on sports betting and fantasy leagues, Portnoy personally handed out copies at subway stations, building a grassroots following.
By 2009, Barstool had moved entirely online, expanding its reach beyond Boston to a national audience. Known as “El Presidente,” Portnoy’s irreverent and unfiltered style, combined with edgy humor and a no-holds-barred approach to content, rapidly attracted a loyal fan base.
The Penn Entertainment Deals: From Millions to Billions
Portnoy’s wealth primarily comes from the sale of Barstool Sports to Penn Entertainment (formerly Penn National Gaming). In January 2020, Penn bought a 36% stake in Barstool for $163 million—$135 million in cash and $28 million in convertible preferred stock—valuing the company at $450 million. This deal also gave Penn the option to buy the remaining stake later.
Penn exercised this option in 2023, acquiring the remaining shares for $388 million, bringing the total purchase price to $551 million. During this period, Penn’s stock price saw significant volatility, reaching a peak of $140 per share in 2021. Portnoy’s convertible stock, if cashed out during this high, would have substantially increased his wealth.
By early 2025, Dave Portnoy’s net worth was estimated at $150 million, according to Celebrity Net Worth. His wealth includes proceeds from the Barstool sale, stock holdings, and investments in various sectors.
The $1 Buyback: Why Portnoy Reacquired Barstool
In a surprising twist, in August 2023, Portnoy bought back Barstool Sports for just $1. This unusual deal was tied to Penn’s new partnership with ESPN, which required them to divest Barstool. Despite the nominal purchase price, the agreement included a clause that entitled Penn to 50% of any future sale of Barstool.
Portnoy quickly clarified that he had no intention of selling the brand again, emphasizing that regaining full control allowed him to return Barstool to its unfiltered roots without corporate restrictions.
Davey Day Trader and Stock Market Ventures
During the COVID-19 pandemic, Portnoy launched “Davey Day Trader” on YouTube, live-streaming his stock trading activities and opinions. Known for his brash style, he entertained viewers by making bold trades and dismissing traditional investment advice. His famous motto, “Stocks only go up,” captured his risk-heavy approach.
In April 2024, Portnoy revealed he was down $1 million on Tesla (TSLA) but remained undeterred. His portfolio has included shares in Spirit Airlines (SAVE), ServiceNow (NOW), Estee Lauder (EL), Wynn Resorts (WYNN), and Celsius Holdings (CELH). Portnoy also invested in cryptocurrencies, holding nine Bitcoins as of January 2024, despite the market’s volatility.
His investments in distressed companies suggest a blend of value investing and momentum trading. Portnoy often mocked Wall Street’s institutional practices, referring to the stock market as “the world’s biggest casino.”
Real Estate Investments: The $42 Million Nantucket Mansion
Portnoy’s real estate portfolio mirrors his taste for opulence. In 2023, he bought a $42 million waterfront mansion on Nantucket Island, setting a record for the most expensive home sold in Massachusetts. The estate features extensive harbor views, multiple bedrooms, and high-end amenities fit for a media mogul.
In addition to his Nantucket estate, Portnoy has been linked to properties in Miami, the Hamptons, and Saratoga Springs. His real estate investments reflect a strategy focused on high-value, high-visibility assets.
One Bite Pizza Reviews: A Business and a Brand
Beyond media and investments, Portnoy has turned his love for pizza into a profitable side venture. His “One Bite” pizza reviews, where he samples a single bite and rates it on a scale of 1 to 10, have garnered millions of views on YouTube and social media. His straightforward catchphrase—“One bite, everybody knows the rules”—has become a cultural phenomenon.
Portnoy’s influence even led to the launch of “One Bite” frozen pizzas, available at major retailers nationwide. This brand extension not only increased his wealth but also broadened Barstool’s audience beyond sports fans.
Philanthropy: The Barstool Fund
In 2020, Portnoy launched the Barstool Fund, donating $500,000 of his own money to support small businesses affected by the pandemic. The fund eventually raised $39 million, helping nearly 350 businesses stay afloat. This philanthropic move softened Portnoy’s controversial image and demonstrated his commitment to his community and followers.
Investments in Rumble and Media Expansion
In early 2024, Barstool signed a deal with Rumble (RUM), an alternative social media platform, giving Rumble access to Barstool’s content. Portnoy’s investment in Rumble reflects his interest in platforms that support free speech and less regulated content. He has actively promoted Rumble on his YouTube channel, adding to his diverse investment portfolio.
How Does Dave Portnoy Spend His Money?
Portnoy’s expenditures mirror his larger-than-life personality. He frequently bets on professional and college sports, attends high-stakes horse races, and indulges in luxury cars and lavish trips. His passion for sports gambling extends to personal bets on college basketball, the NFL, and even the Kentucky Derby.
Beyond gambling and real estate, Portnoy’s investments reflect a strategic blend of traditional and unconventional assets, from distressed stocks to cryptocurrency.
What’s Next for Dave Portnoy?
With full control of Barstool Sports back in his hands, Portnoy’s focus is on expanding the brand’s content across new platforms while maintaining its original edgy tone. He has hinted at new podcast series, video projects, and a deeper push into sports betting, despite the non-compete clause with Penn Entertainment.
Portnoy’s financial success stems not only from lucrative deals but also from his willingness to take risks and defy conventional wisdom. As he continues to build his media empire, Dave Portnoy remains a polarizing yet undeniably influential figure in both the business and media worlds.
His story—from handing out free newspapers to managing a multimillion-dollar portfolio—is far from over. With an estimated net worth of $150 million and a growing portfolio of investments, Dave Portnoy’s next move is eagerly anticipated by fans and critics alike.
