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NEW YORK, NEW YORK – JUNE 29: Dave Portnoy and Erika Ayers Badan attend Dave Portnoy In Conversation With Erika Ayers Badan: Cancel Me If You Can at 92NY on June 29, 2026 in New York City. (Photo by Theo Wargo\/Getty Images)<\/p>\n
Getty Images<\/p>\n
Dave Portnoy has lived in the public eye for nearly 25 years as the founder of Barstool Sports, a sports, media, and entertainment company born out of a free sports gambling newspaper in the mid-2000s before hitting mainstream culture on the Internet several years later.<\/p>\n
Portnoy, 49, released a tell-all memoir, \u201cCancel Me If You Can,\u201d earlier this week where he openly shared everything from the Barstool origin story and public and private feuds to the brand\u2019s sale to Penn Entertainment, his disgust with talent agents, podcast superstars, and an alleged secret firing<\/a> by ESPN.<\/p>\n \u201cIt sucked,\u201d Portnoy told me of writing his memoir, which also addressed prior allegations of racism and misogynistic behavior as The Pirate Ship rose in popularity through the late 2000s and 2010s.<\/p>\n \u201cIt\u2019s just an absolute grind. I mean, I originally went on using a ghost author (Barstool Sports blogger Francis Ellis). The ghost author actually wrote the book, probably spent six to eight months writing the book.<\/p>\n \u201cThen, I read the first paragraph and I was like, \u2018There\u2019s no shot I can publish this. It doesn\u2019t sound like me. I\u2019ll do it myself.\u2019 Then, I spent the next six months, six to eight hours a day, writing it because I\u2019m just a slow writer, and I wanted it to be as good as I could make it.\u201d<\/p>\n Portnoy, who quit his tech sales job and a $80,000 salary to launch Barstool in 2003, started with $30,000 in savings and a $20,000 loan from his dad. Fast forward 20-plus years later, and the die-hard Boston sports fan has transformed what was once a small, ragtag operation in Milton, Mass. to one of TIME\u2019s most iconic companies<\/a> in America.<\/p>\n Erika Ayers Badan, the former CEO from 2016 to 2024 who professionalized the brand, attributed Barstool\u2019s growth, overall success, and eventual $650-plus million valuation to its \u201cfearlessness, constant experimentation, and loose controls on everything but money.\u201d<\/p>\n David Sternberg, Head of Media Consulting at Range Sports, called the brand\u2019s impact on the broader sports media industry “massive.\u201d<\/p>\n He added, “It took sports talk and opinion out of the realm of AM radio and brought it to the web, social media, and podcasts in a way that was more accessible to a wider variety of fans. It also pushed the boundaries of what was viewed as acceptable discourse in sports media and created new personalities outside of traditional broadcast platforms.<\/p>\n Barstool\u2019s Signature Move: Drama<\/p>\n As Sternberg noted, Portnoy \u2014 and by default all of Barstool \u2014 has never shied away from controversy. \u201cWith his brazen sports commentary and readiness to feud publicly with anyone, he is the embodiment of the Barstool brand,\u201d said the media consultant.<\/p>\n In Portnoy\u2019s memoir, the polarizing founder called the contract drama with Call Her Daddy \u2014 a sex, dating advice, and comedy podcast co-founded by Alex Cooper and Sofia Franklyn in 2018 \u2014 \u201cthe most viral story” he had ever been a part of during his time leading Barstool. In short, the co-hosts quickly rose to Internet stardom in 2019, but during the coronavirus pandemic, reportedly \u201cturned on each other<\/a>\u201d as they lobbied for new contracts and more money, all while also trying to potentially find a new media home.<\/p>\n \u201cWe have the Barstool audience, which is obviously huge, and then you have the Call Her Daddy audience at the height of their powers, which was just enormous,\u201d said Portnoy. He alleged in his book that the co-hosts, according to a conversation Cooper had with him, concocted a plan to say they were sexually harassed<\/a> while working at Barstool in order to get out of their talent contracts. <\/p>\n \u201cCall Her Daddy was just getting everybody \u2014 guys, girls, their audience, our audience. It was gigantic,\u201d added Portnoy. \u201cIt was juicy, sensationalized. You had two wildly successful women who appeared out of nowhere and now they didn\u2019t like each other at all.\u201d<\/p>\n Meanwhile, Portnoy also highlighted a much less publicized feud between him and The Chernin Group, which originally bought 51% of Barstool in 2016<\/a> for a reported $12.5 million. <\/p>\n In 2020, Penn Entertainment paid $136 million for 36% of Barstool, with a future path to acquire 100% of the brand years later. In 2023, Penn wished to exercise its right to buy all of Barstool, but both he and Dan \u201cBig Cat\u201d Katz \u2014 co-host of top sports and comedy podcast Pardon My Take \u2014 needed to sign long-term deals. <\/p>\n This was Portnoy\u2019s cash out opportunity. Still, the deal didn\u2019t make Portnoy and others, including Katz, rich overnight. It was a \u201cdelayed rich” through a combination of cash and stock, which would vest over time. <\/p>\n Portnoy felt Katz, who joined Barstool full time in the early 2010s, needed to receive some type of \u201cinstant bonus” for his commitment to Barstool as well as to incentivize him to remain with the company post-acquisition. <\/p>\n \u201cI put myself in Dan\u2019s shoes,\u201d Portnoy said in the memoir. \u201cWhat number would make me so happy that this deal would be a no-brainer? I knew that Big Cat needed to be taken care of in a big way. If he didn\u2019t want to do this deal, he could go sign a huge deal with DraftKings, FanDuel, or ESPN. And without Dan there was no deal.\u201d<\/p>\n Portnoy believed the magic number for Katz was $7 million in addition to his equity, and as he wrote, The Chernin Group suggested that they split paying the bonus with Portnoy. <\/p>\n \u201cIf they weren\u2019t going to pay for it, I felt like I shouldn\u2019t have to pay for it,\u201d Portnoy told me, adding that he was \u201c100%\u201d prepared to blow up the Barstool-Penn deal if Katz didn\u2019t receive the bonus money from Chernin.<\/p>\n Ultimately, “it was an absolute no-brainer\u201d for the investment firm to eventually pay the $7 million, according to Portnoy. He continued, \u201cI mean, VC or private equity or whatever you want to call it, they dream of deals where they put in $12 million and get out $250 million a couple of years later.<\/p>\n “That was part of my point. Nobody was getting rich instantly on our end. We had to work for it. We had to pay taxes. There was stock. They\u2019re already rich, but they already made out better than they could have ever dreamed. … It was shocking that this was even a debate.\u201d<\/p>\n Katz confirmed to me the validity of the bonus story as told as by Portnoy. <\/p>\n When asked what it meant for Portnoy to lobby on his behalf as well as how it impacted his future tenure at Barstool, Katz said it \u201cfurther proved how much Dave has my back and always has done right by me.\u201d<\/p>\n He added, \u201cIt\u2019s why I\u2019ll never leave Barstool. We\u2019re a unicorn in the media world because of the way Dave has led over the years. The money was incredible and changed my life, and I think I earned it over the years but more than money, it\u2019s Dave\u2019s loyalty that makes this place so special. I don\u2019t think anyone in the business\/media world is like Dave in that respect.\u201d<\/p>\n Portnoy\u2019s Future At Barstool Sports<\/p>\n When is Dave Portnoy officially calling it quits at Barstool? At the end of his memoir, he left his future open-ended, so of course I had to ask him what\u2019s next.<\/p>\n Portnoy, who said he doesn\u2019t really think in three- or five-year increments, told me he already thought he would be done with Barstool Sports by now, but \u201cgetting the company back was not in my crystal ball<\/a>, so that obviously changed things dramatically.\u201d<\/p>\n According to Portnoy, he\u2019s \u201cstill locked in\u201d to Barstool for \u201cthe next couple of years.\u201d The lease for the Manhattan office goes through 2029, while the Chicago footprint hums along with Katz at the helm. Portnoy told me he\u2019ll return to Big Noon Kickoff \u2014 Fox\u2019s college football studio show \u2014 in the fall.<\/p>\n \u201cYou never know what the future is going to bring,\u201d he said. \u201cDan and I talk about it, like \u2018how much are you still locked in? You still want to do it?\u2019 As long as people still want to do it, I think he and I both feel a responsibility for lots of our employees who have been with us a long time. As long as we can keep this going without feeling like we\u2019re killing ourselves and being able to take advantage of the fruits of our labor, hopefully we can keep it going.\u201d<\/p>\n Portnoy continued, \u201cWe have advertisers, big ones, who are willing to give us good deals and good contracts. A lot of the time, I\u2019m heavily involved in those deals. I\u2019ll probably be involved for the foreseeable future.\u201d<\/p>\n Below are a couple more noteworthy comments from my conversation with Portnoy:<\/p>\n