How Failing Fast Drives Success

Barstool Sports is a prominent name in the media realm. The company has experienced an astonishing 4,000% growth in both revenue and audience since its founding in 2003. It has expanded from five to 220 million unique blogs worldwide and increased its workforce from 12 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, CEO of Barstool Sports, who joins Suzy founder and CEO Matt Britton on the latest episode of The Speed of Culture to unveil the game-changing elements of a successful company expansion and shed light on the dynamic transformations within the media landscape.

Ayers, 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. Her 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, Ayers has harnessed her expertise to propel the company to unprecedented heights. Her visionary leadership has earned her several accolades, including being recognized as an honoree for Forbes’ Most Powerful Women in Sports, receiving the esteemed Crain’s Notable Women in Sports award, and being honored as one of Adweek’s Most Powerful Women in Sports.

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

Key takeaways:

  • 07:07 – 10:09 – 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 Ayers to seize the opportunity and assume the role of CEO.
  • 10:09 – 13:21 – Scaling Culture and Embracing Change For Ayers, 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.
  • 15:09 – 15:52 – 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.
  • 15:58 – 18:35 – 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 rather than dictating what they should create or how they should create it. 

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