Barstool Sports’ Erika Ayers on Scaling Culture, Creators & Media

8 Jun 2026 · 32 min
31:48

In this Speed of Culture interview, Matt Britton talks with Erika Ayers, CEO of Barstool Sports, about her personal journey from a brand‑obsessed kid to a tech‑advertising professional at Microsoft, Demand Media and AOL, and ultimately to the helm of Barstool in 2016. Ayers explains how she won the CEO role by bypassing traditional hiring channels, the confidence she built through continual failure, and the hiring "DNA" she looks for—curiosity, initiative, and authenticity. She details the challenges of scaling Barstool from 12 to over 400 employees, emphasizing the need to constantly reinvent product strategy (from early blogs to podcasts to short‑form video) and to stay frugal. The conversation moves to Barstool’s diversified revenue mix—advertising, commerce, licensing, live events, pay‑per‑view—and the "authentic" content style that fuels audience loyalty. Ayers contrasts Barstool’s creator‑first model with legacy media, noting the importance of giving talent freedom and data‑driven feedback. The discussion covers the 2020 investment and 2023 full acquisition by Penn Entertainment, the regulatory constraints it introduced, and how the partnership has shaped betting‑related content. Looking ahead, Ayers sees a fragmented, attention‑scarce landscape where creator‑driven, live‑sports‑adjacent experiences will dominate, and she stresses curiosity, risk‑taking, and relentless feedback as advice for young professionals aspiring to leadership.

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