Dave Portnoy, 46, Buys Back His $551 Million Company, Barstool Sports, For $1

Dave Portnoy is the founder, president, and as of August 2023, once again owner of the popular sports-media company, Barstool Sports.

Dave Portnoy announces re-ownership of Barstool SportsPhoto bythe author (licensed under CC BY 2.0)

In January 2020, Dave sold the majority stake of his brainchild to Penn Entertainment, an online casino operator, in an attempt to further grow his brand. Dave stayed on as the president and face of Barstool, but nearly 20 years after starting the wildly successful company in his Boston basement, it was no longer his.

Although the partnership was fruitful for both parties, bringing Barstool's valuation up to $551 million by February of 2021, it was clear El Presidente wasn't made for corporate America.

In a video released on Dave's YouTube channel, he explains some of the struggles Barstool faced when partnering with Penn,

"We underestimated just how tough it is for myself and Barstool to operate in a regulated world... where gambling regulators, the New York Times and Business Insider hit pieces, f*cking with the stock price, every time we did something it was one step forward, two steps back."

Admitting Dave's shoot-from-the-hip style of business, communication, and content strategy hindered Penn's ability to grow in the "regulated industry", Dave feels the split was amicable.

This lack of synergy revealed itself in August 2023, when Penn Entertainment inked a $1.5 billion deal with ESPN. With ESPN wanting to enter the gambling space, they partnered with Penn Entertainment to launch their gambling app, ESPN Bet.

To do this, Penn Entertainment needed to rebrand its Barstool sportsbook app to reflect ESPN's app. And, luckily for Dave, this meant he was able to activate a non-compete clause he had negotiated into his original contract with Penn.

Essentially, if Penn ever decided to sell or rebrand Barstool Sports, Dave would be given the option to buy the company back for $1.00.

Yes, you read that right.

For less than the price of a cup of coffee, Dave was able to buy back his half-a-billion dollar company for $1.00 in exchange for "certain non-compete and other restrictive covenants." This means Barstool can't create a competing betting platform. And, if Dave ever decided to sell Barstool, Penn has the rights to half of its gross profits.

But according to Dave, this won't be an issue, as he has no plans to sell the company ever again.

"For the first time in forever, we don't have to watch what we say, how we talk, what we do, it's back to the pirate ship. And by the way, I'm never going to sell Barstool Sports, ever. I'll hold onto it until I die."

Hey, I'm Hudson! I write about social media, marketing, and modern entrepreneurship. Hit follow for more stories like this one.