Dave Portnoy has seen both success and setbacks in his journey to build his financial empire. He founded Barstool Sports in 2003 as a weekly print publication but filed for bankruptcy in 2004 due to significant gambling losses. Over the years, Barstool Sports transitioned primarily to digital operations and saw significant growth, attracting investments from equity firms such as The Chernin Group. In 2020, Penn National Gaming acquired 36 percent of the company for $163 million, and later purchased the remaining stake for $388 million. However, six months after completing the full acquisition, Penn National Gaming decided to part ways with Barstool Sports, prompting Portnoy to buy back the company for $1 and declare he would never sell it again.
Portnoy’s financial endeavors have also included giving back to the community. Amid the COVID-19 pandemic, he established the Barstool Fund to support struggling restaurants and small businesses. He contributed $500,000 of his own money to the fund and pledged to do whatever it takes to help those in need. Additionally, in December 2024, he made a generous donation of $60,000 to a local pizzeria in Baltimore to help keep its doors open.
In a podcast appearance in March 2023, Portnoy claimed to have made $100 million by selling Barstool Sports and shared the wealth with his colleagues. He also joked about investing in athletics, offering to support his alma mater, Michigan, by providing funds to secure an elite quarterback for their football team. Furthermore, he revealed in a podcast interview in December 2024 that his ex-wife still had access to his finances, despite their separation in 2017, due to their fluid financial relationship and pending divorce issues in Massachusetts.
Portnoy has been transparent about the financial aspects of Barstool Sports, discussing employee salaries and revenue distribution. He revealed details about the base salary of one of the company’s personalities, Grace O’Malley, and emphasized that Barstool treats its creators fairly. Portnoy also addressed the impact of new tariffs in the United States in April 2025, admitting to significant financial losses and expressing frustration over the declining stock market. Despite initially claiming a $7 million loss, he later estimated his net worth had decreased by 10 to 15 percent, potentially amounting to around $20 million lost.
Through his entrepreneurial ventures, charitable contributions, and openness about financial matters, Dave Portnoy continues to make a mark in the business world. His journey with Barstool Sports reflects a mix of ambition, challenges, and resilience. As he navigates the complexities of entrepreneurship and engages in philanthropic efforts, Portnoy remains a prominent figure in the media landscape, showcasing his commitment to both business success and community support.
