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Dave Portnoy Purchased Barstool Again. Can Erika Ayers Badan Maintain His Pirate Ship on Course?

Erika Ayers Badan kicked off her heels and sank into the quiet of her Connecticut house. It’s February in 2023, thick into the spring dash for Barstool Sports activities, the corporate she’s run for seven years. There was the Tremendous Bowl, March Insanity. After which there was the take care of Penn Leisure, a on line casino and racetrack firm, to completely purchase Barstool, after shopping for a 3rd of the enterprise years earlier, with plans to tackle the entire thing. She knew it was coming, however these previous few weeks had been full of trivia. She paid visits to all the cable enterprise channels to discipline questions on what this is able to imply for the corporate, which has revolutionized the best way media corporations construct neighborhood and earn money even whereas stepping in shit by being unapologetically themselves. (Barstool being itself meant being relentlessly chaotic and behaviorally tough.) She led city halls with tons of of workers. She recorded episodes 260 and 261 of her podcast, Token CEO (on Barstool, after all). She purchased David Portnoy a bottle of wine from 2003—the 12 months he based Barstool as a free hometown subway newspaper in Boston, backed by $25,000 from his mother and father, for different Purple Sox bros commuting. (“The individuals at Barstool Sports activities are a bunch of common Joes, who, like most guys, love sports activities, playing, {golfing},” he wrote in his first concern, “and chasing quick skirts.”)

Ayers Badan, who lately remarried and adjusted her title (dropping the Nardini she’d been identified by), is an promoting vet from her Microsoft and AOL days, and was already one of many highest rating girls in sports activities media. She received the Barstool gig over 74 male candidates. Again then, the employees labored out of an outdated dentist’s workplace in Milton, Massachusetts, with a squirrel dwelling within the radiators and consuming their web cables, trash that nobody would take out piling up within the nook. The one approach individuals communicated was via textual content message. There was one lavatory and no payroll. Portnoy paid his employees with private checks, which generally competed together with his playing losses.

On this February day in 2023, the Penn deal closed for $550 million, netting Portnoy and Ayers Badan every round $100 million, in line with Portnoy on Logan Paul’s podcast. “What are you doing to have a good time?” she texted Portnoy and Barstool’s first worker, Paul Gulczynski (referred to as Gaz), as soon as she lastly sat down that night time. Nothing, they responded. What was she doing to have a good time, they requested. Nothing, she replied. There have been issues to really feel happy with and exhausted by, positive. And, if she was being sincere, slightly grief too. “It felt like the top of an period, this challenger model that got here out of nowhere,” she mentioned on the time, “that by no means ought to have made it, and but right here we had been, true to ourselves, making it.”

Barely six months later, Ayers Badan and Portnoy had been seated throughout from one another for dinner at Zero Bond, the members-only membership in NoHo with a no-photo coverage, and, as such, a mecca for celebrities. It was a celebration of kinds, however the tone was totally different, and so was the aim. It was the canine days of August in New York, a couple of hours after the information broke that Portnoy had purchased again Barstool from Penn for $1. The deal, which Ayers Badan mentioned got here collectively over two weeks, was the results of a separate $2 billion alliance between Penn and ESPN. Penn had been desirous to faucet into the $220 billion People have guess because it was legalized 5 years in the past, and hoped that Barstool was its ticket to competing with giants like FanDuel and DraftKings. Barstool is huge, however ESPN is greater, a scaled behemoth that had but to completely dive into that market itself. ESPN can be a part of Disney, whose family-friendliness can be business-friendly in a extremely regulated business. Barstool, against this, represents roughly 2% of the playing market share. And, largely, by the character of who they’re and what they do, the lion’s share of the complications.

“We underestimated how punitive the regulatory surroundings was and the way stringent it was going to be,” Ayers Badan instructed me the morning after the deal was introduced. “Actually, on the core, what Barstool is about—leisure, satire, comedy, opportunistically capturing and creating viral conversations on the web—that’s so antithetical to what a extremely regulated business needs, or what the inventory market likes, that [Penn] simply turned a spot the place this simply was not working.”

To its credit score, she added, Penn embraced Barstool for what it was. They by no means requested for change. However they hit hurdles nearly instantly. For instance, certainly one of Barstool’s largest personalities, Dan “Huge Cat” Katz, who hosts “Pardon My Take,” launched “Can’t Lose Parlay,” which, to his viewers, was a little bit of a joke, as a result of, as Ayers Badan identified, he’s “arguably one of many worst bettors of all time and he at all times loses the parlay.” The gambit landed them in a regulatory listening to in entrance of the Massachusetts gaming fee, who claimed that the title was deceiving prospects by utilizing the language “can’t lose,” though it was very possible that they might. Moreover, so long as they had been speaking about soccer within the context of betting, state laws wouldn’t permit Barstool to do reveals on any faculty campus, which is a demographic linchpin for Barstool’s progress technique. After which there was the difficulty with how Penn’s inventory dipped with every article, together with Enterprise Insider, that detailed allegations of sexual misconduct and playing money owed about Portnoy. On the information of the ESPN deal, Penn’s inventory surged greater than 20% after hours.

“All of this put Barstool in a tricky spot,” Ayers Badan instructed me. “It put Penn in a tricky spot. It additionally put me in a tricky spot as a result of I’m making an attempt to develop a sturdy and rowdy and meandering model the place I don’t know what we’re going to be speaking about subsequent week, subsequent month, subsequent 12 months, however I do know that, to develop Barstool and to have Barstool be related, and vibrant, and significant, it has to have the ability to discover comedy, and leisure, and life-style and issues that, truthfully, simply are actually tough in a extremely regulated, extremely punitive surroundings.”

And so Penn offered its possession again to Barstool in trade for 50% of Portnoy’s proceeds on any future sale of the media model, and a noncompete within the playing house, which business consultants mentioned would possible final simply via the approaching soccer season, and different restrictive covenants. Portnoy, for his half, mentioned that he received’t promote the corporate once more. “I’ve no intentions of ever actually promoting Barstool,” he instructed me the morning after the announcement. “I believe we’re in an excellent state of affairs and until we’re whole idiots, we shouldn’t have to fret concerning the backside line anytime quickly.”

Properly, Ayers Badan may fear about it, as a result of that’s her job, and one she has accomplished for seven years with outstanding ability and success, together with even the August U-turn. (And he or she says she has no plans to go anyplace else.) However when you requested most individuals who’s answerable for Barstool, they might say Portnoy. He goes by El Presidente—or “El Pres”—for starters. And he’s a god to cancel-culture-bemoaning, pizza-loving, red-blooded Robinhood merchants. He’s Donald Trump with out the politics (so, actually, Donald Trump) for the Everyman within the web age and has described Barstool Sports activities as “a localized Maxim” for “younger middle-class white guys who like sports activities.”

However Barstool ballooned nicely previous his wildest intentions. By the numbers, Barstool has greater than 100 podcasts, YouTube reveals, and social media collection; 95 personalities; 65 advertisers; 17 content material verticals; numerous merchandise offered; and greater than 230 million followers throughout social media. Its 1.2 million annual items of content material and 5 billion month-to-month video views attain a 3rd of 18-to-34-year-olds. The place it stands to essentially degree up, so far as Penn noticed it: on-line gaming, a $63.53 billion business, amongst rivals like DraftKings, now a publicly traded firm value round $14.11 billion.

“Everyone seems to be all centered with their mouths hanging open over what Dave Portnoy’s doing,” Ayers Badan had instructed me earlier this spring within the firm’s midtown Manhattan places of work, “and I’m over right here constructing a enterprise.”

Ayers Badan grew up in Gilford, New Hampshire, the daughter of a vocational faculty instructor and a superintendent who noticed no want for tv in the home. On the primary of every month, she would name the cable firm to attempt to arrange an account in her mother and father’ title. “I’d be like, ‘Hello, my husband made me cancel my TV, and I’d wish to deliver it again this month,’ ” she instructed me. “My mother would determine it out, after which I’d simply do the entire thing over once more.”

She describes her younger self as “supercompetitive”: Every day, she counted the variety of steps between house and faculty; the following day, she would attempt to make it in fewer. She lower her enamel in a handful of huge advertising jobs at Constancy, Microsoft, and Yahoo, amongst others, however hit a ceiling. When she heard that Barstool was hiring a CEO, she pounced. She had been an enormous fan for years, as a New England woman who rocked a couple of Barstool T-shirts, which she pursued even if she had to purchase them on “this horrendously janky web site the place your bank card was one hundred pc going to get stolen.” She begged a Barstool guide she knew for a gathering with Portnoy, which he believed was a spontaneous run-in. He’s already met with dozens of what she referred to as “white guys in vests and blue button-ups with an MBA.” She turned as much as the assembly in an Isabel Marant gown with cutouts and kitten heels.