Erika Ayers Badan kicked off her heels and sank into the quiet of her Connecticut home. It is February in 2023, thick into the spring sprint for Barstool Sports, the company she’s run for seven years. There was the Super Bowl, March Madness. And then there was the deal with Penn Entertainment, a casino and racetrack company, to fully acquire Barstool, after buying a third of the business years earlier, with plans to take on the whole thing. She knew it was coming, but these last few weeks were filled with minutiae. She paid visits to all of the cable business channels to field questions about what this would mean for the company, which has revolutionized the way media companies build community and make money even while stepping in shit by being unapologetically themselves. (Barstool being itself meant being relentlessly chaotic and behaviorally tricky.) She led town halls with hundreds of employees. She recorded episodes 260 and 261 of her podcast, Token CEO (on Barstool, of course). She bought David Portnoy a bottle of wine from 2003—the year he founded Barstool as a free hometown subway newspaper in Boston, backed by $25,000 from his parents, for other Red Sox bros commuting. (“The people at Barstool Sports are a bunch of average Joes, who, like most guys, love sports, gambling, golfing,” he wrote in his first issue, “and chasing short skirts.”)
Ayers Badan, who recently remarried and changed her name (dropping the Nardini she’d been known by), is an advertising vet from her Microsoft and AOL days, and was already one of the highest ranking women in sports media. She won the Barstool gig over 74 male candidates. Back then, the staff worked out of an old dentist’s office in Milton, Massachusetts, with a squirrel living in the radiators and eating their internet cables, trash that no one would take out piling up in the corner. The only way people communicated was through text message. There was one bathroom and no payroll. Portnoy paid his staff with personal checks, which sometimes competed with his gambling losses.
On this February day in 2023, the Penn deal closed for $550 million, netting Portnoy and Ayers Badan each around $100 million, according to Portnoy on Logan Paul’s podcast. “What are you doing to celebrate?” she texted Portnoy and Barstool’s first employee, Paul Gulczynski (known as Gaz), once she finally sat down that night. Nothing, they responded. What was she doing to celebrate, they asked. Nothing, she replied. There were things to feel proud of and exhausted by, sure. And, if she was being honest, a little grief too. “It felt like the end of an era, this challenger brand that came out of nowhere,” she said at the time, “that never should have made it, and yet here we were, true to ourselves, making it.”
Barely six months later, Ayers Badan and Portnoy were seated across from each other for dinner at Zero Bond, the members-only club in NoHo with a no-photo policy, and, as such, a mecca for celebrities. It was a celebration of sorts, but the tone was different, and so was the purpose. It was the dog days of August in New York, a few hours after the news broke that Portnoy had bought back Barstool from Penn for $1. The deal, which Ayers Badan said came together over two weeks, was the result of a separate $2 billion alliance between Penn and ESPN. Penn had been eager to tap into the $220 billion Americans have bet since it was legalized five years ago, and hoped that Barstool was its ticket to competing with giants like FanDuel and DraftKings. Barstool is big, but ESPN is bigger, a scaled behemoth that had yet to fully dive into that market itself. ESPN is also part of Disney, whose family-friendliness is also business-friendly in a highly regulated industry. Barstool, by contrast, represents approximately 2% of the gambling market share. And, largely, by the nature of who they are and what they do, the lion’s share of the headaches.
“We underestimated how punitive the regulatory environment was and how stringent it was going to be,” Ayers Badan told me the morning after the deal was announced. “Really, at the core, what Barstool is about—entertainment, satire, comedy, opportunistically capturing and creating viral conversations on the internet—that is so antithetical to what a highly regulated industry wants, or what the stock market likes, that [Penn] just became a place where this just was not working.”
To its credit, she added, Penn embraced Barstool for what it was. They never asked for change. But they hit hurdles almost immediately. For example, one of Barstool’s biggest personalities, Dan “Big Cat” Katz, who hosts “Pardon My Take,” launched “Can’t Lose Parlay,” which, to his audience, was a bit of a joke, because, as Ayers Badan pointed out, he is “arguably one of the worst bettors of all time and he always loses the parlay.” The gambit landed them in a regulatory hearing in front of the Massachusetts gaming commission, who claimed that the name was deceiving customers by using the language “can’t lose,” even though it was very likely that they would. Additionally, as long as they were talking about football in the context of betting, state regulations wouldn’t allow Barstool to do shows on any college campus, which is a demographic linchpin for Barstool’s growth strategy. And then there was the issue with how Penn’s stock dipped with each article, including Business Insider, that detailed allegations of sexual misconduct and gambling debts about Portnoy. On the news of the ESPN deal, Penn’s stock surged more than 20% after hours.
“All of this put Barstool in a tough spot,” Ayers Badan told me. “It put Penn in a tough spot. It also put me in a tough spot because I’m trying to grow a robust and rowdy and meandering brand where I don’t know what we’re going to be talking about next week, next month, next year, but I do know that, to grow Barstool and to have Barstool be relevant, and vibrant, and meaningful, it has to be able to explore comedy, and entertainment, and lifestyle and things that, honestly, just are really difficult in a highly regulated, highly punitive environment.”
And so Penn sold its ownership back to Barstool in exchange for 50% of Portnoy’s proceeds on any future sale of the media brand, and a noncompete in the gambling space, which industry experts said would likely last just through the coming football season, and other restrictive covenants. Portnoy, for his part, said that he won’t sell the company again. “I have no intentions of ever really selling Barstool,” he told me the morning after the announcement. “I think we’re in a very good situation and unless we’re total idiots, we shouldn’t have to worry about the bottom line anytime soon.”
Well, Ayers Badan might worry about it, because that’s her job, and one she has done for seven years with remarkable skill and success, including even the August U-turn. (And she says she has no plans to go anywhere else.) But if you asked most people who is in charge of Barstool, they would say Portnoy. He goes by El Presidente—or “El Pres”—for starters. And he is a god to cancel-culture-bemoaning, pizza-loving, red-blooded Robinhood traders. He’s Donald Trump without the politics (so, really, Donald Trump) for the Everyman in the internet age and has described Barstool Sports as “a localized Maxim” for “young middle-class white guys who like sports.”
But Barstool ballooned well past his wildest intentions. By the numbers, Barstool has more than 100 podcasts, YouTube shows, and social media series; 95 personalities; 65 advertisers; 17 content verticals; countless merchandise sold; and more than 230 million followers across social media. Its 1.2 million annual pieces of content and 5 billion monthly video views reach a third of 18-to-34-year-olds. Where it stands to really level up, as far as Penn saw it: online gaming, a $63.53 billion industry, among competitors like DraftKings, now a publicly traded company worth around $14.11 billion.
“Everyone is all focused with their mouths hanging open over what Dave Portnoy’s doing,” Ayers Badan had told me earlier this spring in the company’s midtown Manhattan offices, “and I’m over here building a business.”
Ayers Badan grew up in Gilford, New Hampshire, the daughter of a vocational school teacher and a superintendent who saw no need for television in the house. On the first of each month, she would call the cable company to try to set up an account in her parents’ name. “I’d be like, ‘Hi, my husband made me cancel my TV, and I’d like to bring it back this month,’ ” she told me. “My mom would figure it out, and then I’d just do the whole thing over again.”
She describes her young self as “supercompetitive”: Each day, she counted the number of steps between home and school; the next day, she would try to make it in fewer. She cut her teeth in a handful of big marketing jobs at Fidelity, Microsoft, and Yahoo, among others, but hit a ceiling. When she heard that Barstool was hiring a CEO, she pounced. She had been a massive fan for years, as a New England girl who rocked a few Barstool T-shirts, which she pursued despite the fact that she had to buy them on “this horrendously janky website where your credit card was 100 percent going to get stolen.” She begged a Barstool consultant she knew for a meeting with Portnoy, which he believed was a spontaneous run-in. He’s already met with dozens of what she called “white guys in vests and blue button-ups with an MBA.” She turned up to the meeting in an Isabel Marant dress with cutouts and kitten heels.