When Erika Ayers Badan joined Barstool Sports as the company’s first chief executive officer in July 2016, she was entering a flourishing operation and helped to actualize more of its potential. Ayers Badan had previously served as president and chief revenue officer of Bkstg and immediately noticed distinct aspects of the Barstool Sports business once she started on the job. In fact, she was doing work for the company from the start of the interview process, assimilating into the environment and sentiment among employees. Ayers Badan remained at Barstool Sports until this past January when she left the company and joined Food52 as its new chief executive officer a few months later.
On the day Ayers Badan was hired by Barstool Sports, Ayers Badan remembers watching the Barstool Rundown broadcasting live from founder Dave Portnoy’s apartment. After the show guest made several racial slurs live on the air, she remembers questioning what she was walking into working for the company. During a recent appearance on The Colin Cowherd Podcast, Ayers Badan discussed her early years with Barstool Sports and how she stabilized parts of the venture, including determining which people were employees of the company.
“Dave wasn’t exactly sure who was on the payroll or not,” Ayers Badan said. “It was a lot of like – there were a lot of guys in Boston with Barstool J.J. and Barstool ‘insert first name here,’ and they seemed like they worked for Barstool, [but] they didn’t work for Barstool. Dave wasn’t clear if they paid them or not, so there was a lot of like, ‘Who is this person and do they actually work here?’”
In her time as a new employee when the company was smaller, Ayers Badan became cognizant of the tightrope that Barstool Sports was walking with its content. Portnoy, along with other personalities such as Dan “Big Cat” Katz and Kevin “KFC” Clancy, are people that Ayers Badan described as being affable but also shrewd. Staggering the line of comedy through their content was part of the role she found difficult amid trying to perform her role and position the company for sustained success.
“I had worked at startups and at big companies,” Ayers Badan explained. “Barstool was just very, and still is, very alive in that it was real time. It was building a company [in] real time in the public eye.”
Aside from hosting his eponymous podcast and television program, The Herd, Cowherd is an entrepreneur and operates The Volume, a digital sports media brand with various content offerings. Amid his conversation with Ayers Badan, he recalled a story of befriending Nike founder Phil Knight while working in Oregon and remembers his opening manifesto when the company began. Cowherd has recently spoken to his staff at The Volume about one of these points, which is “It won’t be pretty,” which remains true and has been something he has experienced in business.
“That’s something I think as younger people tend to be a tad more fragile and easily offended, I’ve talked to some people and said, ‘I’m not sure you’re a good fit for my company,’” Cowherd said. “I view fragile as a weakness and relentless as the ultimate strength; that we all step in shit and you’ve got to get over it fast and don’t let one interception become two and one bad day become a week.”
Ayers Badan concurred with this point and described it as encapsulating the essence of her forthcoming book, “Nobody Cares About Your Career: Why Failure Is Good, the Great Ones Play Hurt, and Other Hard Truths,” which is set to be released on Tuesday, June 11. Careers, she elucidated, are built over several mundane and ugly days with many mistakes, and there is a fundamental nature of understanding how to fail and overcome it.
“What was brilliant about Barstool was that it was always trying to understand the line, and that’s what made it so interesting and so alive and so captivating to fans, but also so difficult on the business where I always had to have multiple lines of revenue because I didn’t know,” Ayers Badan said. “Tuesday afternoon, we could be offending an advertiser; we could have said something that’s flaring up in the New York Post. I never knew what was going to happen, so safety and calm could come from having multiple levers to keep payroll going and the business happening.”
Through the process of audience adoption, which comes from having a message, attracting and retaining listeners and then having them advocate on behalf of the entity, she believes there is burgeoning pent-up demand that is extremely palpable in scope. Over the years, Barstool Sports has cultivated brand equity partly through its personalities and the relationship with the audience.
“I am a highly impatient person, but if you put talent on a platform or create content for a platform, and it gets traction, you’ve got to get – the longer you do that, the more you let that marinate, the further you explore with it – I will wait weeks, months,” Ayers Badan said. “I would wait years because the reality is the more audience you grow – and if you find, you’ve got to.”
Conversely, some companies eventually choose to sell for lucrative profit, including Barstool Sports when it completed a transaction that gave PENN Entertainment full ownership of the entity over two deals worth $551 million. Portnoy purchased the company back from PENN Entertainment last summer for $1 as it prepared to enter a deal with The Walt Disney Company and rebrand its sportsbook to ESPN BET. Ayers Badan believes that once entities secure fiscal windfall in this manner, it can cause them to become more indolent.
“The best years at Barstool, I think, were probably the earliest years, and then they were the beginning of my years because it was such a grind,” Ayers Badan said. “We didn’t know if we would make it; we still had so much road to climb. The best years were not after the PENN acquisition, so I think getting the bag also comes with responsibilities and changes things, and that’s hard for a mission-driven, passion-driven brand.”
