Erika Ayers Badan Thought the Time Was Right to Leave Barstool Sports (2024)

As Erika Ayers Badan was commuting into New York City to work as chief executive officer of Barstool Sports, she noticed that her DMs were being flooded with inquiries from industry professionals and driven newcomers with different work-related questions. Whether it was about workplace culture, meetings or having the confidence to fail in the quest for success, she recognized the inquisitive probe amid an altered paradigm in which full-time, in-person roles have rendered themselves more seldom to find.

Ayers Badan found time on her commute to review these questions and began to compile her analysis pertaining to the theory behind work and its evolution over several years. The work environment looks different from the time she began in the business, and this exercise, which functioned as a creative outlet, effectively permitted her to devote time to her passion and expertise amid a turbulent time in the office. This project evolved into a new book titled “Nobody Cares About Your Career: Why Failure Is Good, the Great Ones Play Hurt, and Other Hard Truths” set to be released on June 11.

Barstool Sports has built a legion of consumers with its ability to attract and retain an audience while the media ecosystem continued to innovate towards digital platforms. The company previously sold a 36% stake to then-branded PENN National at a valuation of $163 million in 2020, making PENN its official gaming partner. Under the terms of the deal, PENN would increase its ownership to approximately 50% the following three years; however, it ended up purchasing the remaining stake for almost $390 million last February. PENN Entertainment owned and operated Barstool Sportsbook, which made Barstool Sports part of a public venture in a highly regulated environment.

“That was a complete 180 from where we had been and was challenging,” Ayers Badan said. “And I also think it was challenging for PENN because PENN wanted Barstool to be Barstool, but not in a way that risks their relationships with the street or their relationships with the regulators, and that was challenging across the board, I think, for everybody.”

Throughout her eight-year tenure as chief executive officer of Barstool Sports, Ayers Badan was aware of the company’s ability to straddle the proverbial line and controversial nature of the brand. As a result, she knew that the entity needed multiple revenue streams to protect against objectionable events and occurrences. For example, if someone wrote a blog post that disconcerted advertisers, Barstool would have a lucrative commerce business to recoup the losses.

Over time, the company added several verticals to its offering, including areas surrounding pay-per-view events, subscriptions and content licensing. The company abstained from being obstinate in its mindset but also stretched itself thin, made mistakes and was able to always remain dynamic and optimize its process to deliver results.

“There was so much tension inside of Barstool, which I really argue is what kept it very sharp is there was a tension of trying to do too much,” Ayers Badan said. “There was a tension of what the advertisers wanted versus what the content people wanted, [and] there was a tension of resources.”

Ayers Badan learned of the job opening in the first place while meeting with The Chernin Group, an investment firm that purchased a majority stake of Barstool Sports in 2016. The conversation was part of a fundraising process for Bkstg, a startup company focused on music artists creating content directly for fans. Although the acknowledgment of such an investment came off to her as a throwaway comment, she opened the application and spoke about what she loved about the brand and what could be fixed. She left the meeting with a sentiment of anxiety, assuming that the company would find someone with an MBA working in sports that fit the profile.

“The way that Dave [Portnoy] would write a blog and then create a T-shirt was, I thought, really smart and very captivating,” Ayers Badan said, “and he brought people along with his journey, and then they wore and promoted his journey for them, and I thought that was incredibly powerful and incredibly captivating.”

Prior to joining Bkstg, Ayers Badan was the chief marketing officer of AOL and had responsibilities pertaining to business-to-consumer and business-to-business work. Even though she had realized a dream job, she perceived herself not to be fulfilling her potential, nor enjoying the work itself. Possessing the fortitude and courage to move on came from previous experience and lessons learned, and the willingness to pivot proved beneficial to her career.

Through a friend, Ayers Badan was introduced to company founder and president Dave Portnoy and met him in the West Village. It was evident that Portnoy was looking for a business partner, something that Ayers Badan knew was not always the case with company founders, and she actively pursued the job. Nearly two months later, Portnoy was in Times Square wearing a tuxedo and announcing Ayers Badan as the first chief executive officer of Barstool Sports.

“What was really interesting about Dave was that while he had this larger than life, wild, raucous personality, he was really rational and he was very thoughtful about what he was building and also really honest about what he was looking for and what he knew and what he didn’t know,” Ayers Badan said. “No one hid anything about Barstool, so when I got there, it was a little bit of a gong show for a while, but that’s actually what made it so special, and that’s really what I loved about it because Barstool had all of the right things, and it just needed to have honestly like scaffolding built around it.”

Surpassing 74 men vying for the job, Ayers Badan was maligned and disgraced by several women executives in the business world. Some people indicated that she was engaging in career suicide, but she was confident that it was the best thing she had ever done before starting. The rejection was difficult and the company offended many people, resulting in the brand being stigmatized and castigated on numerous occasions.

“No one was coming to help me and no one really cared if we succeeded or not, and frankly they would have been just as happy, if not happier, if we didn’t succeed,” Ayers Badan said, “and so the only way to earn respect was really to set [out in]… building Barstool and to stop worrying about what everybody else thought about what I was doing or what we were doing or who I was or who we were, and I think that focus was really important.”

Ayers Badan views herself as a collaborative leader who enjoys seeing people challenge and push one another. Earning the pseudonym “Token CEO,” of which she hosted a podcast by the same name, she sought to understand the processes within Barstool and make improvements without sacrificing the identity of the brand.

“I don’t think what was unique about me as a candidate was that I was a woman,” Ayers Badan said. “I think what was unique about me was I didn’t think it should change who it was. A lot of times, that meant protecting our content people and the creative.”

The varied revenue stream gave Barstool more latitude to fail without sacrificing the stability of its business or the bottom line. Over her time as chief executive officer, the company built out its digital media platforms and accrued large followings on several different outlets. Throughout the process, she remained vigilant and patient in crafting an entity that would withstand challenges and capitalize on opportunities.

“I think media companies are so desperate for the revenue and they put too much cost going in if that makes sense, and they’re also not diversified the way they need to,” Ayers Badan explained. “It’s almost like, ‘If cable’s going well, why learn the internet?,’ and it’s like, ‘Well, cable’s going okay,’ but we always wanted to be everywhere. We were so ambitious about growing audience that we followed the audience first – we didn’t follow the business model first.”

Barstool Sports has demonstrated a penchant for creating and maintaining a community of invested devotees who have genuine interest pertaining to the company itself. Although the brand was first founded in 2003 as a weekly sports publication, it has added coverage of entertainment, pop culture and other subject areas within its portfolio through podcasts, digital series and special events. The company has thrived in brand conversion among those in the younger demographic with an ensuing capacity to move product and generate positive return on investment for advertisers. An aspect of that success is attributable to its programming and personalities, some of whom include Dan “Big Cat” Katz, PFT Commenter (Eric Sollenberger), Ria Ciuffo and Kevin “KFC” Clancy.

“Barstool found Frank The Tank on ranting about New Jersey Transit,” Ayers Badan said. “You look at Brandon Walker; you look at Miss Peaches. I think Dave really has the ability to find people who are inherently funny, even if not intentionally so.”

Even though she never intended to be a talent for Barstool Sports, Ayers Badan was frequently on camera by virtue of being in the office. In fact, she launched a podcast during the pandemic and also appeared on select Barstool programming. Barstool Sports, which has offices in New York City and Chicago, frequently captures content outside of the studios and creates moments surrounding the workplaces themselves. One series in particular, titled Surviving Barstool, traps employees in the office as they battle to win a cash prize.

“I remember meeting with Dave before I even took the job, and Dave’s vision for New York was one part like instead of going to Saturday Night Live, you came to Barstool Sports if you were a really funny, talented person, which happened,” Ayers Badan said. “And then the second was The Truman Show where the camera was just on 24/7, and the camera was on 24/7 and I was there, so it kind of happens organically.”

Beyond the office walls, Barstool records a plethora of content around different locales, including Portnoy’s popular One Bite pizza review series. The company has also thrived in the live event space, serving as the exclusive title sponsor and broadcast partner of the Arizona Bowl for several seasons, purchasing the Rough N’ Rowdy boxing promotion and calling the Battle of the Badge NYPD-FDNY hockey game. When PENN Entertainment owned Barstool and was considering its own media strategy, Ayers Badan believes that the company could have taken the approach on bidding for media rights with a professional sports league.

“Barstool can produce live sporting events in a way that is uniquely Barstool and incredibly funny and comical,” Ayers Badan said. “I think the way Barstool promotes live sporting events has all the requisites, and it has a lot more.”

Live sports broadcasts, Ayers Badan presumes, represent the only viable outlet in broadcast and cable television concurrent with the rise of streaming platforms. Because of the storylines and drama within the games, it is oftentimes appointment viewing for fans. As a result, she is optimistic about the future of the business.

“I think you’ll watch sports in places perhaps you hadn’t before,” Ayers Badan said. “You’ll get commentary in a way that’s decentralized. You won’t watch the pregame show – you’ll go on TikTok – so I think it’ll become more disintermediated, but I think the business will always be strong because the audience is there.”

The partnership with PENN Entertainment, while it had some beneficial moments, caused Barstool Sports to have to adhere to the demands of the parent company. This occurred when Ben Mintz was fired after using derogatory language on a show despite Ayers Badan, Portnoy and Katz trying to save his job. Since then, there have been examples of media companies embracing irreverent, nonconformist behavior and licensing programming from independent content creators.

“Audience is more fragmented than ever, and traditional media and the gatekeepers have been more disruptive than ever, and when there is such intense fragmentation – I think you’re seeing it really this year in the TV Upfront, which is the erosion of cable is here,” Ayers Badan said. “It’s not starting to erode; it’s eroding, and I think companies are having to make bets on people because the driving forces in media right now are individuals and influencers.”

PENN Entertainment ultimately entered into a 10-year agreement with The Walt Disney Company to launch ESPN BET and subsequently sold Barstool Sports back to Portnoy for $1, along with various provisions related to revenue sharing and market competition. It represented the second company sale within a year, and Ayers Badan felt that she had achieved her purpose in being brought on.

“I think that Dave is the right steward of Barstool, I felt great about Barstool being back under Dave and I felt like we built something that’s going to last the test of time,” Ayers Badan said. “The infrastructure and the system and the energy inside of Barstool is so strong, and I feel so good about that.”

At the beginning of the year, it came as a surprise to many people that Ayers Badan resigned her position as chief executive officer of Barstool, and she ended up leaving the sports media industry entirely. Ironically enough, it was when she was writing the chapter, “Do I Stay or Do I Go?,” in which she began considering leaving the company. All of this was occurring as Portnoy was in the process of reacquiring ownership of the company.

In the end, she felt that nothing would surpass what Barstool Sports did in 2023 and was confident in the direction of the company under Portnoy. Moreover, Ayers Badan was looking for a new challenge with a startup brand in a new category, substantiated in joining Food52 as its chief executive officer.

“I was getting approached a lot by sports betting companies, sports companies [and] sports leagues, and I was like, ‘If I’m going to stay in sports, there’s no place better than Barstool, and if I’m going to stay in entertainment, there’s no place better than Barstool,’” Ayers Badan said, “but I also was like, ‘Gosh, I have all this energy and I really am a student of the game and I’d like to see if I [can]… play a different sport or [if I] can play on a different field,’ and that really was the driver.”

The process of building companies and making an impact in the marketplace energizes Ayers Badan and keeps her invested in her career. Although it was an arduous decision to leave Barstool, she felt staying too long would be a disservice both to herself and to her colleagues. While she is enjoying her new role with Food52 and anticipating the release of her book, Ayers Badan could return to sports media in the future as the industry aims to continue driving profits amid market segmentation and a demand for niche offerings.

“It’s a real challenge – it’s a completely different space,” Ayers Badan said. “It’s foreign in some ways and familiar in others, but I really loved my time in sports and I love the energy of sports. I would love at some point to come back. I’m still on the board of the PLL – I’m really passionate about what they’re doing – so yeah, I’d love to come back.”