Here's How Dave Portnoy Really Made His Staggering Fortune

Dave Portnoy, aka "El Presidente" of Barstool Sports, is probably best known for his big personality and an even bigger bank account. He's currently estimated to be worth a jaw-dropping $150 million. But make no mistake, it hasn't always been that way. "I used to play like Party Poker to try to win money so Renee could get her nails done," Portnoy once confessed on "Barstool Radio," referencing his ex-wife, Renee Portnoy. File that one under details you probably didn't know about the now larger-than-life personality. 

So, how exactly did Portnoy make his staggering fortune? As it turns out, Portnoy took an alternative one-man newspaper and turned it into a media empire! The story goes, in 2003, Portnoy broke away from a sales job he loathed and started Barstool Sports — only then, it was a free black-and-white newspaper surviving on ad sales from offshore illegal sportsbooks and steakhouses. Although Barstool Sports wasn't an overnight success, eventually, it morphed into an online publication. "It was all word of mouth," Portnoy told the Daily Mail about the company's seismic growth into a media empire. "I never put a penny into it, all the money that was coming in was going back out for Barstool and to find writers," he recalled.

Shortly after Barstool's seismic growth, the investors started calling. Portnoy initially brushed them off, but that all changed in 2016 when he sold The Chernin Group a majority stake in the company while keeping 100% of the editorial control. At the time, Barstool Sports was reportedly valued at somewhere between $10 million and $15 million. "This was not my cash out moment," Portnoy wrote in an open letter to his beloved Stoolies regarding the business deal. "This was our best shot to literally take this thing to the moon. To swing for the fences."

Still, Dave Portnoy's greatest money-making move to date didn't happen until 2023. Way back in 2020, Penn Entertainment purchased a 36% stake in Barstool Sports. Then, in February 2023, the entertainment company forked over another $388 million to acquire the remainder of the company. All in all, they spent a whopping $551 million for the acquisition.

Alas, the investment didn't exactly go as planned. In a jaw-dropping turn of events, Penn struck another deal with ESPN and sold Barstool Sports back to Portnoy for a meager $1 in August of the same year. In true fashion, Portnoy issued an "emergency press conference" video wherein he explained that Barstool and Penn just weren't right for each other. "We got denied [gambling] licenses because of me, you name it," Portnoy lamented. "So the regulated industry [is] probably not the best place for Barstool Sports and the type of content we make."

These days, Dave Portnoy has grown accustomed to the finer things in life. In 2023, the Wall Street Journal reported that the businessman plunked down a staggering $42 million for a waterfront home on Nantucket. "I went from being able to afford renting for a day to a weekend to a week to a month to renting for the entire summer to buying a house to now buying a house beyond even my wildest imaginations. This is now my view," he tweeted about the astronomical real estate purchase on X, formerly known as Twitter. 

Portnoy is adamant, however, that being rich isn't all sunshine and rainbows — namely when it comes to paying taxes. In 2013, as his net worth started to climb due to the success of Barstool Sports, so did the amount Portnoy owed Uncle Sam, and he made it clear he was none too pleased by it. "As I become rich I'm becoming upset at how many taxes I pay. It's really cramping my accent to richville," he fired out in a tweet. Alexa, play "Mo Money Mo Problems" by The Notorious B.I.G.