Barstool Sports founder Dave Portnoy has showcased a remarkable knack for business, evolving Barstool from a simple blog into a media powerhouse valued at hundreds of millions of dollars. In two significant deals, one in 2020 and another in 2023, he sold the company to PENN Gaming for a staggering $551 million, which undoubtedly positioned him among the elite in the sports media landscape.
This lucrative transaction didn’t just make headlines; it also enabled Portnoy to make history with the largest residential real estate purchase in Massachusetts, acquiring a home that has since become a centerpiece of his extravagant real estate portfolio. While it’s likely that Portnoy could have managed to amass his properties over time, the funds from PENN’s acquisition certainly accelerated his journey into luxury living.
Fast forward to August 2023—just months after PENN completed its acquisition of Barstool—Portnoy made a surprising move. He bought Barstool back for just one dollar. Yes, you read that correctly. One single dollar was all it took for him to reclaim his empire, a story he shared during an engaging appearance on Shannon Sharpe’s podcast, *Club Shay Shay*. His decision wasn’t merely a whimsical act; it was driven by a combination of his competencies and the shifts in PENN’s corporate strategy.
Portnoy elaborated on this during the podcast, explaining the dynamics involved: “Barstool Sports was sold to PENN Gaming. Gambling is super regulated. You need licenses. I’m a controversial guy, and that was creating challenges for PENN in securing those licenses. They faced an opportunity to partner with ESPN, and they realized they weren’t the right holder for Barstool. They couldn’t simply hand it over, so it had to be an official sale.”
He recognized that he had the timing on his side. “A bunch of factors all came together for me at the right time,” he said, highlighting how the stars aligned for this unique situation. The deal was also advantageous for PENN; they could leverage Barstool’s extensive database to better connect with their dedicated customers.
Interestingly, this wasn’t Portnoy’s first rodeo with selling Barstool; he previously sold the company to Chernin Media in 2016 before ultimately selling to PENN. However, now that he’s regained control, he has no plans to let go again anytime soon. If he decides to sell in the future, the terms dictate that PENN would receive 50% of the proceeds. “That, right off the bat, probably prevents it,” Portnoy stated. Still, he admitted, “If you want to write me a check for a billion [dollars], never say never. I reserve the right to change my mind.”
Barstool remains a dominant force in the podcasting sector with some of the most popular shows in the sports realm, like *Pardon My Take* and *Spittin Chiclets*, which are consistently featured in Spotify’s top 10 sports podcasts. In contrast, Sharpe’s *Club Shay Shay* sits just below them at 16th place on the Spotify charts.
Unless a billion-dollar offer comes Portnoy’s way—highly unlikely yet still possible—it seems he’s firmly in the driver’s seat at Barstool, steering the company into what could be an exciting future. As a man who has navigated the tumultuous waters of media and entrepreneurship, Portnoy’s journey resonates with anyone who understands the rollercoaster of building something they’re passionate about. It’s a testament to the idea that with the right mix of grit, timing, and maybe just a bit of luck, even a dollar can make a monumental difference.
Image Source: Shannon Sharpe @ Instagram
