Dave Portnoy: The Man Behind The Barstool Empire

What Exactly is Dave Portnoy's Net Worth?

Alright, let’s break it down. Dave Portnoy, the guy who turned a small print publication into a digital sports media empire, is worth a cool $150 million. That’s right, $150 million. His rise to fame began with the creation of Barstool Sports, a digital powerhouse that changed the game for sports media. Over the years, Dave sold parts of Barstool to investors like The Chernin Group and Penn Gaming, with the final transaction occurring in August 2022. But here's the twist: Dave re-acquired Barstool from Penn Gaming in August 2023—for the princely sum of one dollar. That’s not a typo, folks. Let’s dive deeper into how he built this empire and how his net worth stacks up.

Back in 2016, The Chernin Group purchased a majority stake in Barstool. Then, in January 2020, Penn Gaming bought a 36% stake for $163 million, with an option to buy more later. By August 2022, Penn Gaming exercised its option to buy Barstool outright for $390 million. That’s a total of $550 million over the years. But Dave wasn’t done yet. He retook full ownership of Barstool, giving him complete creative control once again. We’ll unpack the details of this deal later, but trust me, it’s a fascinating story.

Early Beginnings: From Swampscott to Michigan

Let’s rewind the clock. Dave Portnoy was born on March 22, 1977, in Swampscott, Massachusetts. Growing up in a small coastal town, he developed a love for sports and entrepreneurship early on. After graduating from Swampscott High School, Dave headed to the University of Michigan, where he earned a degree in education in 1999. But education wasn’t his only focus—Dave was already thinking about business ideas that would shape his future.

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Post-graduation, Dave moved to Boston, where he worked for an IT market research firm called Yankee Group. While it wasn’t exactly his dream job, it gave him valuable experience in the business world. It was during this time that the seeds for Barstool Sports were planted. Dave had a vision, and he wasn’t afraid to chase it.

Barstool Sports: From Print to Digital Dominance

In 2003, Dave founded Barstool Sports as a print publication focused on the Boston metro area. The paper was filled with fantasy sports predictions, gaming ads, and sports coverage. But Dave had bigger plans. In 2007, he launched the Barstool website, and things really took off. Over the next decade, Barstool grew into a sports media juggernaut, thanks to Dave’s unique blend of humor, sports analysis, and a touch of controversy.

On Barstool, Dave goes by the nickname “El Presidente” or “Stool Presidente.” The site is known for its snarky sports coverage and its mix of attractive women, a combination that some have described as “ESPN meets Girls Gone Wild.” Despite the controversy, Barstool has become one of the most popular sports sites on the internet. Dave’s dedication to the brand is unmatched—he was known to work 10+ hour days, even on weekends, in the early days of Barstool.

In 2017, Dave launched a pizza review series called “One Bite with Davey Pageviews.” The goal? To review every pizza place in Manhattan. It’s just another example of how Dave keeps things interesting and engages his audience in unexpected ways.

The Chernin Group Acquisition: A Turning Point

In January 2016, Dave sold a stake in Barstool to The Chernin Group for $10–$15 million. By 2018, The Chernin Group had invested an additional $20–$25 million, increasing its stake to 60%. Despite this, Dave remained in full control of the content, which expanded to include podcasts, gambling content, merchandise, alcohol brands, TV shows, and more. The Chernin Group’s investment gave Barstool the financial backing it needed to grow even further.

Penn National Acquisition #1: The Big Deal

In January 2020, Penn National Gaming made a major move, acquiring a 36% stake in Barstool Sports at a valuation of $450 million. The deal involved an initial cash payment of $163 million and an option for Penn to buy an additional 14% stake for $62 million within three years. This transaction diluted The Chernin Group’s 60% stake to 36%, matching Penn National’s stake. The remaining 28% was owned by Dave and a few key executives, including CEO Erika Nardini.

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Penn Gaming Stock: A Rollercoaster Ride

When the deal was announced, Penn Gaming’s stock surged to an all-time high of $38 per share. But then the Coronavirus pandemic hit, and the stock plummeted to $7 per share by March 17, 2020. By May, it had rebounded to around $20 per share, and by August, it had more than doubled to $50 per share. By January 2021, the stock had reached $100 per share, and by March 2021, it hit $130 per share. It was a wild ride, to say the least.

Portnoy’s Stock Holdings: A Closer Look

According to a Penn Gaming Q1 2020 10-Q SEC filing, of the $163 million in cash, roughly $23 million was given as convertible preferred stock, and $3 million was set aside for “forward arrangements.” The convertible stock could eventually be converted into approximately 0.50% of Penn Gaming’s market cap, or about 883,000 shares. When Penn Gaming’s market cap was $10 billion, a 0.50% stake was worth $50 million. Dave reportedly owned one-third of that stake, which worked out to around $16 million. Combine that with his remaining stake in Barstool and previous transactions, and Dave’s net worth was estimated at $100 million.

Penn National Acquisition #2: The Final Chapter

At some point, Penn National acquired an additional 14% of Barstool, bringing its total ownership to 50%. Then, on August 17, 2022, an SEC filing revealed that Penn Gaming had exercised its right to buy the remaining 50% of Barstool for $387 million. This marked the end of Dave’s partnership with Penn Gaming—temporarily, at least.

Penn Sale Back to Portnoy: A Surprising Move

On August 8, 2023, the same day Penn announced a long-term exclusive betting partnership with ESPN, Dave revealed that he had re-acquired full ownership of Barstool. In a statement, Penn Gaming’s CEO said, “The divestiture allows Barstool to return to its roots of providing unique and authentic content to its loyal audience without the restrictions associated with a publicly traded, licensed gaming company.”

So, why would Penn agree to sell Barstool back to Dave for just $1? Well, first, Barstool’s value is heavily tied to Dave’s involvement, and it’s unlikely he would have worked under a new owner. Second, Penn retained the right to half the proceeds if Dave sells Barstool again. Third, Penn Gaming planned to take an $850 million loss on Barstool, which includes the $550 million it paid over the years and $300 million in costs and investments. Finally, the deal includes a non-compete clause and restrictions on Dave working for a competing betting company or disparaging ESPN or Penn Gaming.

As Penn Gaming’s CEO put it, “PENN sold 100% of the outstanding shares of Barstool to David Portnoy in exchange for a nominal cash consideration ($1.00) and certain non-compete and other restrictive covenants.”

The Barstool Fund: Giving Back During a Crisis

In 2020, during the height of the COVID-19 pandemic, Dave donated $500,000 to the Barstool Fund, a charity launched to help small businesses impacted by the crisis. Over time, the fund raised $39 million, which was distributed to nearly 350 small businesses. It’s a testament to Dave’s commitment to giving back and supporting the communities that have supported him.

Personal Life: Love, Scandal, and Real Estate

Dave Portnoy’s personal life has been just as eventful as his professional one. He was married to Renee Satherthwaite from 2009 to 2017. In 2021, he began dating Silvana Mojica. But it hasn’t all been smooth sailing. In December 2019, a sex tape of Dave leaked, and Business Insider alleged sexual misconduct against him. Dave denied the allegations and sued the publication. In November 2022, a federal judge dismissed the lawsuit, and Dave dropped the appeal in February 2023.

Back in 2004, Dave reportedly filed for bankruptcy protection after racking up gambling debts, owing $59,000 to credit card companies and $18,000 to his father. But that didn’t stop him from bouncing back and building one of the most successful media brands in the world.

Real Estate: Dave’s Luxurious Lifestyle

Dave Portnoy has made some serious real estate moves over the years. In 2023, he paid a record-breaking $42 million for a waterfront mansion on Nantucket, set on 1.2 acres. Other notable purchases include a $2.2 million Nantucket home, a $14 million Miami waterfront home, a $9.75 million house in the Hamptons, and a $1.4 million property in Saratoga Springs. It’s safe to say Dave knows how to live the high life.