Dave Portnoy Bought Barstool Back. Can Erika Ayers Badan Keep His Pirate Ship on Course?

By Emily Jane Fox

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 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.”

Everyone has their “MOUTHS HANGING OPEN over what Dave Portnoy’s doing,” says Ayers Badan, “and I’m over here BUILDING A BUSINESS.”

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.

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“All of the prior candidates were turning me and our guys off because they were coming in and saying, ‘Here’s what you’re doing wrong,’ and we didn’t really think we were,” Portnoy told me. “She said that she loved what we’re doing, but, my God, there’s so much more here. Who knows what direction you could go in.”

The problem was no one currently knew the answer. They basically just had one ad deal with a local beer company and a handful of bloggers whose only edicts were to post every 30 minutes. They never actually talked, they often weren’t paid, and they all seemed to actually kind of hate each other. “It was like a rock band that should have broken up,” Ayers Badan noted. Devlin D’Zmura—Barstool’s first intern in the Milton office, which makes him “Milton-tough,” he reminds me from his new perch in Barstool’s far posher midtown offices, where he now works as a senior director—put it as, “It was just all stubborn assholes, all working on their own thing. And then Dave at the top, who was poor and fat and not the guy you know today.”

Ayers Badan read early on that if she could listen to Portnoy and all of the Barstool guys and understand the core of what they were thinking, she could make it happen. But if she told them they couldn’t do it, that was certain death. “Dave could be the alpha,” she said. “I didn’t need to be the alpha. I didn’t want to be the alpha. What I could do is say, Oh, you want to go do this? Then I’m going to build it.”

She put cameras everywhere and figured out whatever platform du jour would give audiences a front-row seat. Things started to work, and the company moved down to New York, in a midtown office that housed everyone in one big, loud room. Some of them ended up living on Ayers Badan’s couches—in her office and her home—when they first moved, because they couldn’t afford to live on their own. D’Zmura, who’d left the company, applied to come back once he saw what Ayers Badan was doing to shift the business. “A lot of it was seeing how different Dave seemed to be,” he told me. “He could untether himself to do even more crazy shit because the stuff he wasn’t good at was being taken care of.” At that point, D’Zmura was working for $500 a week, still wearing the hand-me-down Cole Haan loafers and shorts Portnoy had cast off on him five years earlier. The shoes essentially had no soles left. Ayers Badan pulled him aside one day and asked for his shoe size. She ordered him three pairs on the spot and went into their new merch closet to give him a stack of new sweatpants. “It was some Andrew Carnegie vibes or something,” he said. “It made me work even harder and be more committed and believe in this place more.”

The reality of today’s internet is that the people who consistently go viral are not people who would have been sitting at the popular table in the cafeteria (perhaps Alix Earle aside). They’re specific and niche and connect to that little weird fraction inside of you that, IRL, you’d literally never let out, but in the cold, dark cover of internet anonymity, you’re free to follow and like and engage with. Barstool’s offices are, more often than not, described in profiles or in Reddit threads online as Brotopia unbound. That’s fair, both in expectation and reality. Within the two floors that Barstool occupies in the New York offices, there are two full bars, which I’d swear were sticky without daring to touch them. The walls are cluttered with TVs tuned in to all the sports channels and flags reading “viva la Stool” and “Saturdays are for the boys.” There’s a room with eight saggy leather chairs that scream that they’ve seen some things, each with a microphone at its feet, all arranged stadium style in front of about a trillion TV screens. To the right of them is a fist-size hole in the wall, a relic from the time one of the guys punched through it during a playoff game. In the bullpen, there are dozens of desks that have what seem like a minimum of 900 tchotchkes on them—college sports flags or hometown T-shirts or plastic hamburgers. Every single person I came in contact with during my visit encouraged me to “take anything I wanted” off any desk, which felt as much like a generous offering as it did a plea for help as it did a dare. There are cameras rolling everywhere all the time in that place. Everything is content.

I passed Joey Camasta, the cohost of Barstool’s Out & About, going live at his desk to test out a new glitter eye shadow. There had been a big uproar earlier in the morning because, after the long Memorial Day weekend, Barstool personality Frank the Tank had come into the office to find one of his specialty sodas—a limited-edition Mountain Dew—was missing, and everyone in the office was pointing fingers and no one was safe. Ayers Badan walked into her office to find pajamas and a blanket on her couch, making it abundantly clear that someone had been sleeping in her office over the weekend. She barely shrugged. No space, no privacy, no boundary can’t be pushed (D’Zmura still eats half of her leftover lunch every day. “Sometimes she has lobster!” he told me).

When I sat down with Kate Mannion, the Afghanistan war vet who cohosts their military podcast Zero Blog Thirty, she pulled up her Phillies T-shirt to show me that she was holding her jeans together with a hair tie. She’s a few months pregnant with her second son and refusing to buy maternity pants. “I can’t believe I’m showing this to a Vanity Fair reporter,” she confessed. Mannion came to Barstool as so many hopefuls do—by way of a photo she tweeted remarking that the calzone she’d ordered looked remarkably like a vagina. The tweet picked up steam, and people started tagging Uncle Chaps, a Marine and Barstool host who happened to have a running feature centered around objects that resembled genitals. “We ended up talking about how I was in the military and he invited me on his show, and then it just grew from there. It was the calzone that launched my whole everything.”

She came into the Barstool office for the first time in an LC Lauren Conrad for Kohl’s shirt with shoulder pads and her résumé. Everyone was in basketball shorts, she remembered. No one looked at her printout. “If Chaps says you’re good, you’re good,” she remembers Portnoy telling her. She started guesting on Zero Blog Thirty and blogging until they hired her full-time. Until then, she’d read stories about the misogyny within and around Barstool. People warned her. Google warned her. After a few weeks, she says, “I was like, Oh, this isn’t the land of sports bros. This is the land of misfits. This is the land of dorks and nerds like me, who, yes, are super-passionate sports fans who all seem like douchebags. They just do. But they’re authentic. It’s a bunch of creative weirdos who want to make their own content, a million of us with a million very weird personalities.”

The Barstool stamp has meant big business for its stars. Once they make it onto the network, and particularly once they’re tweeted out from the Barstool main account, it’s on. If they understand their audience and if they churn out the kind of content that works at a clip, it’s a rocket ship. That’s what happened with Call Her Daddy, the once unbelievably raunchy sex podcast launched by Barstool in 2018 by two young, hot best friends named Sofia Franklyn and Alex Cooper. Barstool got them cheap and put them front and center. Within about two seconds, the show exploded. Episodes would launch on Wednesday at midnight, and by 1 a.m., there were all sorts of anomalies with download data from Spotify and Apple, because users on college campuses share IP addresses, so everything would short out, Ayers Badan told me. “It broke everything.” The cohosts ultimately had a public falling out. Portnoy publicly sided with Cooper, who signed on with Barstool and retained the podcast. Last year, she made a $60 million deal with Spotify, which Ayers Badan said she deserves every cent of. “I’d rather have an Alex Cooper that screws you at the end, every day of the week. Because you know what? She worked for us, we worked for her, we taught her a lot, she taught us a lot. It’s like a sports team. It’s like you have a star quarterback and her contract is up, and she went to the big leagues.”

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With a fan base this rabid, coupled with a command of the media, a punishing publishing cadence, and control of all of the back-end data and publishing, Barstool is one of the more powerful advertising platforms.

Joanne Bradford, who had hired Ayers Badan at Microsoft and Yahoo, became her customer once she was at Barstool. By that point, Bradford was the president of Honey, the online coupon business, and it became one of the biggest advertisers on Call Her Daddy, which she said was one of the most effective ad buys they ever had. “Erika really, really trusts the authenticity of that fan base and understood the power of Dave’s army in order to build Barstool into the antithetical voice of corporate marketing,” she said. “She built infrastructure for that voice to break through and to get advertisers. And while it’s certainly not for the bluest of chips, for people that want performance and want to really be a part of a community, advertising with Barstool Sports gives you that.”

It may not be for the bluest of chips, as it didn’t work for Penn, because, at any moment, someone at Barstool, from Portnoy on down to any of the hundreds of people who appear on the platform each week, could say or do something that will turn the internet and advertisers against them. Portnoy, to his core, is a self-immolating executive whose devotees get off on his flames. His ascent happened despite, or perhaps because of, the fact that his offensiveness was destined for internet stardom. Like when he wouldn’t take down photos from the blog that showed Tom Brady’s child’s penis until the police literally came knocking, or used the N-word (among other racist behavior), or said that a woman in tight pants “kind of deserved to be raped.” This summer, after rumors of Brady chatting with Kim Kardashian at a party swirled, Portnoy drew a line: Brady shouldn’t deign to date someone like the successful beautiful reality mogul, but he could “fuck her in a motel.” In 2021, Insider published a report in which three women alleged that sexual encounters with Portnoy had turned violent and humiliating. A follow-up story last year reported that a handful of women alleged that Portnoy filmed them without their consent during sex. Portnoy and Barstool denied the claims, and Portnoy sued the publication, its editor, CEO, and the reporters. A federal judge dismissed the lawsuit for lack of evidence of “actual malice.” Portnoy filed an appeal but ultimately dropped it. Portnoy declined requests to comment on this. He framed the reports as a witch hunt, urging Stoolies to fight against the tide. If they supported him and wanted to “beat cancel culture,” then everyone buy as many Barstool-branded frozen pizzas that Walmart carried. Fans flocked to the stores.

Ayers Badan released a podcast at the time defending Portnoy. In our interview, Ayers Badan said that she’s protective of him “to this day, though Dave doesn’t need protecting. I love him. I really do.” They were never perfect, she added. They never said they were. They showed every flaw. The office is The Truman Show. “The DNA is unapologetic, highly authentic, real, fallible, totally human. Everybody here fucks up all the time.” Portnoy said he couldn’t have predicted the amount of backlash they would get over the years. “She doesn’t back down. And if she did, we would’ve been probably dead in the water a long time ago. There’s no way for us or me to have known that she would’ve had the same exact backbone that we do and I do,” he said. Like when she got shit on Twitter for wearing a shirt during an interview that read “Feminine,” which a commenter thought read “Feminist” and took great offense to, given Barstool’s point of view. Ayers Badan responded to that critique: “It’s cashmere, bitch.” A poster of the phrase hangs above her desk.

“It’s a big victory when you get your company back,” said Portnoy. “Not being part of a publicly traded company is probably a relief for everyone.”

“It’s certainly very noisy where I live,” she said when I brought this up. “It also shows that we’re doing something that’s relevant. And I would choose relevance for Barstool every day.”

It’s no wonder that Barstool’s Barstoolness would immediately clash with almost any other ethos. But Penn is a betting company. And now, with fresh cash and no leash, Barstool is spinning it as a win.

Penn, too, will say only good things. “Dave, Erika, Big Cat, and everyone at Barstool have been great to work with over the last 3.5 years and were the ideal partners to help us launch and rapidly scale our digital footprint across 16 jurisdictions in the US,” PENN Entertainment CEO and president Jay Snowden said on the company’s earnings call last week. “We gained a tremendous amount of knowledge and experience with them over the last several years.”

“It’s a big victory when you get your company back,” Portnoy told me the morning after the deal was announced. “Not being part of a publicly traded company is probably a relief for everyone.” Chief among them, he said, is Ayers Badan, who supported him as he led the negotiation to get the company back.

“When you look at most acquisitions, 80% of them fail. And I think there’s a lot of things that happen after an acquisition. The founders check out, everyone cashes out, and you make peace that the thing that you’ve built now belongs to somebody else and it’s not yours anymore,” she told me. “What’s very different in this case is that I stayed in and didn’t opt out and give up. I’m so psyched for Penn and ESPN. I think there’ll be a great match for all the reasons we weren’t. Now this can go back to what made it so genius, which is being comfortable on the edge of something.

“We have a very unique view of the world and go places where our audience is, and to make things for them there. And our eyes are going to be just on that.”

This story has been updated.

A version of this story appears in the September 2023 issue.

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