Erika Ayers Badan grew up in New England without a lot of money and in a household without a TV, but what the CEO of Barstool Sports did have was access to print media. Her childhood bedroom was plastered with Benetton and Absolut Vodka ads.

Barstool CEO Erika Ayers Badan sat down with ASI President and CEO Tim Andrews for a Q&A keynote.

“Brand really, really matters because it’s the crystallization of what you stand for,” Ayers Badan said during an energizing keynote Q&A at the ASI Power Summit on Monday, Oct. 23, held at the Langham in Pasadena, CA.

That keen understanding of the power of bold branding helped Ayers Badan as she forged a career in the freewheeling days of the early internet. Initially, she said, she thought she wanted to be a lawyer and joined the law group of Fidelity Investments, but it wasn’t a good fit.

“It was about constraining things,” Ayers Badan said. “I wanted to create things.”

So, she took a significant pay cut to work in the company’s advertising group, noting that the career pivot was the best decision she ever made. “I liked that nobody cared about the internet [back then], and everyone left me alone,” she said. “I could work really hard and screw up a lot.”

But, she added, “If I could harness an engineer and a marketing idea and a little bit of money, I could make something great.”

Ayers Badan went on to hold leading roles at Microsoft, AOL, Demand Media and Yahoo before taking the reins at Barstool Sports in July 2016, winning the CEO gig over 74 male candidates. She’s led the unapologetically authentic brand through explosive growth, expanding it from a regional blog with a staff of 12 to a national powerhouse with hundreds of employees. Under her leadership, Barstool has become a top 10 podcasting publisher in the U.S., with the world’s number-one sports, hockey, golf and music podcasts. Barstool drives 5 billion monthly video views and 216 million social followers.

The key, she said, wasn’t to change the company that was created in Boston by Dave Portnoy in 2003 as a free subway newspaper. “It was really about evolving it,” she added.

When she became CEO, Ayers Badan said, Barstool “was a mess.” There was no P&L, and she wasn’t even sure whether all the people who had Barstool in their Twitter handles were paid staffers or not. “It was very chaotic,” she added. “There was nothing but a great brand, and a lot of passion to create. … They knew they had to blog every 30 minutes and had a deep core of productivity. Beyond that, everyone was allowed to do their thing.”

During the Q&A with ASI President and CEO Tim Andrews, Ayers Badan fielded questions about Barstool Sports’ many accusations of misogyny, noting that it’s “the least sexist place I’ve ever worked” because everything is out in the open and “come as you are.”

“Wearing all your mistakes is disarming and authentic,” she said. “Every single day our creative team starts with a blank page, and they have to make people laugh. That’s hard to do. Doing that and being good at that comes with a lot of mistakes.”

She also acknowledged that the media landscape has changed dramatically in the last two decades, noting that what you could post about in the early aughts is not OK in 2023. Rather than apologize for every crass or rude post Barstool Sports created before her tenure, Ayers Badan chose to focus her time on “creating something new” and making the brand bigger and better.

“I’m not spending all my time cleaning up the floor, but really focusing on elevating the ceiling instead,” she said.

ASI Media Editor-in-Chief C.J. Mittica talks with Erika Ayers Badan after her keynote.

Ayers Badan addressed the media company’s two recent sales: In February, casino and racetrack company Penn Entertainment acquired Barstool for $550 million. By August, Portnoy had bought back Barstool from Penn for $1. The initial acquisition by Penn wasn’t a good fit, and Ayers Badan and Barstool “were kind of contorting ourselves” to make it work.

“We were about 2% of their revenue but 2,000% of their headaches,” Ayers Badan said, adding that she feels good about Portnoy buying the brand back because everyone knew the deal with Penn wasn’t working.

Ayers Badan also spoke about the power of merch and licensing, particularly as a passive income stream. “If my ad business faltered, I need a business to fall back on,” she said. During her time with the company, Barstool has launched several successful products, including flavored vodka Pink Whitney, Big Deal Brewing’s golden ale, Pirate Water malt beverage and Stella Blue Coffee.

Ayers Badan brought smiles to attendees’ faces with a premium plush dalmatian she received from public safety company Axon; she sits on the board. At a recent police chief convention, she said, Axon gave away the stuffed dogs – each wearing a branded bandanna around its neck.

“You walked out of the convention center, and all you saw were dalmatians,” Ayers Badan said. “That’s the power of a great item. It brands you instantly. … Whether it’s a T-shirt or a stuffed animal, if it’s part of a bigger story and something that’s compelling, the power of that is just remarkable.”

As far as the future of Barstool Sports is concerned, Ayers Badan said it’s a fool’s errand to try to predict where the brand will go. But, she added, Barstool will continue to meet its fans where they are.

“The internet is so delicious in that it changes all the time, and we’ll change with it,” she said.