Dave Portnoy, an American sports media mogul and internet entrepreneur, has accumulated a net worth of $150 million. He became wealthy by founding Barstool Sports, a digital sports powerhouse. Portnoy’s fortune grew as he sold portions of Barstool to various buyers, ultimately completing a deal with Penn Gaming in August 2022, marking a significant turning point in his financial trajectory.
The Journey of Barstool Sports
Portnoy’s entrepreneurial journey began when he founded Barstool Sports in 2003. Initially, the company was a print publication serving the Boston metro area, focusing on fantasy sports predictions and gaming ads. By 2007, Barstool transitioned to an online platform. Over the following decade, Portnoy dedicated long hours to expanding the business, often working 10+ hour days, including weekends.
The Growth of Barstool
Under Portnoy’s leadership, Barstool evolved into a massive sports media entity, blending snarky sports coverage with engaging content. The brand has been compared to a mix of ESPN and “Girls Gone Wild” due to its bold, unconventional content. As the site gained popularity, Portnoy became known as “El Presidente” or “Stool Presidente,” helping Barstool rise to the ranks of one of the top sports sites online.
One Bite with Davey Pageviews
A key moment in Barstool’s growth occurred in 2017 when Portnoy launched the viral pizza review series “One Bite with Davey Pageviews.” The show’s goal was simple: review every pizza place in Manhattan. It quickly became a cultural phenomenon, drawing millions of viewers and further propelling Barstool’s expansion.
Chernin Group’s Acquisition of Barstool
In January 2016, Portnoy sold a stake in Barstool to Peter Chernin’s The Chernin Group for $10-15 million. By 2018, Chernin had increased its stake to 60%, while Portnoy retained control over Barstool’s content, which now included podcasts, TV shows, merchandise, and alcohol brands. Despite the change in ownership, Portnoy remained the face of the company.
In January 2020, Penn National Gaming made a significant move, acquiring a 36% stake in Barstool Sports for $163 million. This purchase valued the company at $450 million. The agreement also included an option for Penn Gaming to increase its stake to 50% by paying an additional $62 million within three years. As a result, Portnoy’s influence within the company remained central, as he continued to oversee content creation.
The Impact of Penn Gaming’s Stock
After Penn Gaming’s initial investment, the company’s stock saw dramatic fluctuations. It surged to $38 per share, only to crash to $7 a share due to the global pandemic. However, by mid-2020, the stock rebounded, eventually peaking at over $130 a share in 2021. During this period, Portnoy’s stock holdings with Penn Gaming became increasingly valuable, contributing to his growing wealth.
Further Penn Acquisitions of Barstool
Over the next two years, Penn Gaming expanded its stake in Barstool, eventually acquiring a total of 50% ownership by 2022. This was followed by a second major deal, which saw Penn acquire the remaining 50% of Barstool for $387 million. These acquisitions culminated in Penn Gaming taking full control of Barstool by August 2022.
In an unexpected turn of events, Portnoy regained full ownership of Barstool Sports in August 2023. Penn Gaming, which had previously acquired Barstool in two separate transactions, sold it back to Portnoy for a nominal fee of $1.00. This move came after Penn’s exclusive betting partnership with ESPN was finalized. The sale was part of a strategic decision, as Penn Gaming took an $850 million loss on its Barstool investments, including both purchase costs and operational expenses.
The Terms of the Deal
As part of the transaction, Portnoy agreed to a non-compete clause and other restrictions, ensuring Barstool’s return to its roots of producing authentic and unique content. Additionally, Penn retained the right to half of any future proceeds should Portnoy choose to sell the brand again. Despite this, Portnoy’s return to full ownership re-established him as the driving force behind Barstool’s success.
The Barstool Fund and Philanthropy
During the COVID-19 pandemic, Portnoy demonstrated his philanthropic side by launching the Barstool Fund in 2020. The initiative, which began with a $500,000 donation, raised over $39 million to support small businesses impacted by the crisis. The fund ultimately helped nearly 350 businesses, showcasing Portnoy’s commitment to giving back to the community during a time of unprecedented challenges.
Personal Life and Relationships
Dave Portnoy’s personal life has also garnered attention over the years. He was married to Renee Satherthwaite from 2009 until their divorce in 2017. In 2021, Portnoy began a relationship with Silvana Mojica. His personal life has not been without controversy, including the leak of a sex tape in December 2019 and allegations of sexual misconduct made by Business Insider. Portnoy denied the accusations and filed a lawsuit against the publication, which was eventually dismissed by a federal judge in 2022.
Financial Troubles in the Early Years
Before his rise to fame, Portnoy faced financial struggles. In 2004, he filed for bankruptcy protection after gambling losses, owing significant amounts to credit card companies and even his father. This setback, however, did not define his future success. Instead, it became part of his broader story of overcoming adversity to build a multi-million-dollar empire.
Real Estate Investments
In addition to his business ventures, Portnoy has made several high-profile real estate purchases. Over the years, he has acquired properties in desirable locations, including a $2.2 million Nantucket home, a $14 million Miami waterfront estate, and a $9.75 million house in the Hamptons. Most notably, in September 2023, Portnoy purchased a waterfront mansion on Nantucket for $42 million. This purchase set a record for the area, surpassing previous sale prices by approximately $5 million.
Dave Portnoy’s rise from a small-town entrepreneur to the owner of one of the most influential sports media brands in the world has been nothing short of remarkable. With a net worth of $150 million, Portnoy’s journey through various acquisitions, challenges, and business ventures has solidified his status as a major figure in sports media. His ability to navigate the complexities of ownership, investment, and content creation has ensured Barstool Sports remains a dominant force in the industry. From his early days in Boston to his latest acquisition of Barstool, Portnoy’s story serves as a testament to resilience, innovation, and the power of unconventional thinking.
