Podcasts

The Art of Failing: Erika Ayers, CEO of Barstool Sports on Failing Fast and Why It Matters to Drive Success

Nov 16, 2023
Feb 27, 2025
 • 
 min read

“Falling and failing gives you the confidence to succeed.”
— Erika Ayers

Barstool Sports is a prominent name in the media realm. The company has experienced an astonishing 4000% growth in both revenue and audience. It has expanded from five to 220 million unique blogs worldwide and increased its workforce from twelve to 400 employees.

Despite this extraordinary growth, Barstool Sports has managed to successfully preserve and nurture its distinctive cultural DNA. At the forefront of this remarkable journey is Erika Ayers, who joins us to unveil the game-changing elements of a successful company expansion and shed light on the dynamic transformations within the media landscape.

Erika, a trailblazer in the media industry, holds the prestigious title of being the first-ever CEO of Barstool Sports, a renowned media magnate. With a profound understanding of digital innovation, she constantly disrupts the industry and stands as a seasoned executive at the forefront of content creation, distribution, and monetization.

Erika's unwavering commitment to staying ahead of the curve has made her an early adopter of internet culture, propelling digital entrepreneurship and driving substantial revenue growth in esteemed companies like Microsoft, Yahoo, and AOL.

Since taking on the CEO role at Barstool Sports in 2016, Erika has harnessed her expertise to propel the company to unprecedented heights. Her visionary leadership has earned her several accolades, including being recognized as one of AdWeek’s and  Forbes' Most Powerful Women in Sports and receiving the esteemed Crain's Notable Women in Sports Award.

Check out the key takeaways of this episode or the transcript below to discover effective strategies for elevating your media business while preserving your unique cultural identity.

  • Embracing Failure: The Path to Unleashing Confidence - Failure is an essential part of success. Constantly pushing yourself beyond your comfort zone grants you the confidence needed to achieve your goals. It was this very confidence that empowered Erika to seize the opportunity and assume the role of CEO.
  • Scaling Culture and Embracing Change - For Erika, scaling Barstool’s culture proved a formidable challenge. But the key to successful cultural expansion lies in hiring individuals with curiosity, motivation, and initiative. Furthermore, the company's willingness to break away from conventional approaches has been pivotal to its success. Flexibility and a proactive willingness to embrace change are key elements that have propelled Barstool forward.
  • The Unmatched Flavor - Barstool's special sauce lies in its authentic, real, and genuine content. It embraces humor, showcases strong opinions, and welcomes the unexpected, all while maintaining a constant and relentless presence. Barstool's content captures the essence of raw, unfiltered experiences. The uniqueness of Barstool's content also lies in its constant presence, operating 24/7.
  • Navigating the Evolving Media Landscape - The media industry currently faces significant challenges. The distinction between being a creator company and a traditional media company has become blurred. So Barstool focuses on giving its creators the freedom to express their ideas and visions and not dictating what they should create or how they should create it.
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