Anyone familiar with Barstool Sports founder Dave Portnoy knows that he has never shied away from controversy. His questionable history includes multiple arrests, a failed campaign to become the Mayor of Boston, and countless accusations of racist and sexist remarks. But if you think he’s ever shown remorse for his behavior, we’d like to point you to a June 2020 tweet that reads, “Memo to the cancel cops. I knew this was coming before you did. And I’m ready. You don’t cancel me. I cancel you.”
Perhaps Dave Portnoy’s net worth explains his unapologetic attitude. Being a bad boy has clearly paid off—the 44-year-old is said to be sitting on a fortune, even after blowing much of it on bad bets. Find out what Portnoy is worth in 2021 and how he spends his money today.
Dave Portnoy Grew ‘Barstool Sports’ From A Local Paper To A Media Empire
Portnoy founded Barstool Sports in 2003 in Milton, Massachusetts. Its earliest form was a print publication intended to serve men like himself: red-blooded, testosterone-fueled sports bettors.
“I hated my job, and I wanted to find something I liked doing, and I gambled,” said Portnoy. “So the paper was really hardcore sports, hardcore gambling, fantasy football-and I would hand it out outside subway in Boston… Over time we started going away from just hardcore sports and gambling to have more a lifestyle feel.”
Portnoy never had any intention of using his education degree from the University of Michigan—his only goal was to work for himself. That said, he had no idea that Barstool would blow up the way it did. He moved the paper online in 2007, and his crude, dude-friendly brand quickly attracted millions of readers.
The site’s popularity also caught the attention of big investors. In 2016, Portnoy announced that he had sold 51 percent of Barstool Sports to The Chernin Group, a media company that owns stakes in various brands, including Pandora, Tumblr, and Crunchyroll. The subsequent $10 million payday required Portnoy to relocate headquarters to New York; in exchange, he retained control of the publication’s content and voice.
“Do I like Manhattan? No. Do I want to be in Manhattan? No. Do I like these people looking at me during this press conference? No. But it’s the right move,” Portnoy said at a press conference to announce the acquisition.
Even if the deal made him an overnight multi-millionaire, Portnoy was just getting started. An even bigger financial windfall was just a few years away.
Dave Portnoy Sold ‘Barstool Sports’ To Penn National Gaming
With the help of its new owners, Barstool Sports morphed from a gambling rag to a multi-media lifestyle brand. A report by Vox estimated that in 2019, the company earned between $90 and $100 million in revenue, largely from podcasts, merch sales, and corporate partnerships.
Following the successful growth, the brand was re-sold by The Chernin Group the following year. In January 2020, casino operator Penn National Gaming purchased a 36 percent stake in Barstool for $163 million in cash and stock. In 2023, the corporation will pay another $62 million to raise its total stake to 50 percent. An option to buy controlling ownership will be determined at that time.
Portnoy is among a small group of Barstool execs that maintains 28 percent ownership of the company. Although he has never disclosed exactly how many shares of Penn National Gaming he acquired through the deal, he says it’s “a ton.” Find out what he’s done with that cash during the pandemic.
Portnoy Has Lost Quite A Bit Of Money On Day Trading And Gambling
As a self-described gambler, Portnoy hasn’t let his success (or Covid) get in the way of his own risk-taking tendencies. In March, he deposited $3 million into an E-Trade account and live-streamed his foray into day trading.
“I like betting on sports,” Portnoy said. “Sports ended, and this was something that was still going that I could do during the day.”
A month earlier, he was among the hoards of amateur bettors who invested in shares of meme stocks like GameStop. But his participation in the “Reddit Rally” cost him big when investing app Robinhood restricted trades and caused the market to plummet.
“I have officially sold all my meme stocks. I lost 700k ish,” Portnoy tweeted. “[Robinhood CEO] Vlad [Tenev] and company stole it from me and should be in jail.”
Portnoy wasn’t the only trader to lose a small fortune, but at least he could afford it. Losing sums in the low six figures barely makes a dent in his overall worth. Plus, he’s been in similar situations before. Check out this YouTube video from 2019, where Portnoy bets $10,000 each on 53 March Madness games—all against the favorites to win:
Dave Portnoy’s Net Worth
As of 2021, multiple sources estimate that Dave Portnoy’s net worth is $120 million. Portnoy confirmed a similar nine-figure sum in April 2020. However, he added that market swings—Penn National’s stock price in particular—made his fortune subject to volatility.
“I think my net worth was around $100 million,” Portnoy said just after Penn shares plummeted. “Literally probably cut in half, maybe more now.”
We sense that Portnoy isn’t at risk of losing everything anytime soon. Although he’s no longer CEO of Barstool Sports, he remains the Chief of Content. His brash persona is tied to the brand, which means he will always have a reliable source of income.
But for those who want to follow in his footsteps, Portnoy offers a clear warning: try to mimic his entrepreneurial spirit, not his gambling habits.
“Do not [day trade] thinking you’re going to make money,” Portnoy said. “Do it for entertainment, do it for fun. I would never day trade with money that you can’t afford to lose.”
He continued, “And if you’re looking to invest, it’s long term, not the short. If you’re doing what I’m doing, be prepared to lose.”