Outsider CEO Deirdre Lester on building a lifestyle brand

Outsider is a media and commerce brand focused on a particular view of “the American lifestyle” that, to me, takes its cues from the South, emphasizing college football, hunting, fishing, wraparound sunglasses and the like. Recently, Deirdre Lester moved from CRO of Barstool Sports to become the CEO of Outsider. The goal is similar to Barstool: Use personality-driven publishing – former NFL QB Jay Cutler is chief design officer at Outsider – to build a deep connection with a like-minded community, then complement the media with commerce operations. Some key takeaways from our conversation:

Finding the sweet spot between individuals and institutions is a big opportunity. The unbundling of publishing has put the focus on individual creators, but there are only so many Mr. Beasts in the world. The more tangible opportunity is the Goldilocks approach with institutional brands that can tap into the power of individuals to establish tight ties with an audience. Outsider is doing that with Cutler and popular podcaster Marty Smith.

Lifestyle publishing brands are more about AOV than CPM. Publishing has been stuck in a default mindset that the audience either pays with data and attention to ads or with money through subscriptions. Commerce – real commerce, not just affiliate links – offers a third way to build product companies with media used for efficient distribution and, ideally, premium pricing power based on the credibility established with customers.

Doing both media and products is hard. These are different businesses with different dynamics. The rough patch hit by Food52, a prime example of publishers pivoting to product, shows how difficult it is to manage both publishing and products. Publishing is all about managing conflicts, and that can get even messier when publishing is in the service of moving products.