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by Outsider

Outsider is a media and lifestyle company that celebrates American culture through the entertainment, sports, and news we cover and the authentic goods we create.

Outsider reaches more than 22 million monthly users and has over 8 million social followers. The lifestyle and media brand was created by former NFL quarterback Jay Cutler, alongside the founders of On3.com, Rivals.com (acquired by Yahoo! In 2007), 247Sports (acquired by CBS Sports in 2015), and Pop Culture Media (acquired by CBS Interactive 2017).


Join the 8 million Outsiders following our social media:

Brand Mission

Outsider provides a place for people to find community through the stories we tell, the clothes we wear, and even the beer we drink. Outsider Media and Lifestyle personifies the identity of American culture: hard work, individuality, and adventure.

Outsiders have a passion for moments shared outside: at football games, on the lake, around the fire, on the patio, or wherever you may gather. 

Yes, this is a media brand, but true Outsiders know it’s more than that: Being an Outsider is a lifestyle. 


Deirdre Lester
Former CRO of Barstool Sports

Jay Cutler
Co-Founder / Chief Design Officer
Former NFL quarterback. Leads Outsider Lifestyle division.

Shannon B. Terry
Executive Chairman / Co-Founder
Former CEO and founder of four digital publishing brands. All exited with acquisitions by publicly traded companies.

Andy Johnson, President — Former CFO of three media brands and one fast-growing eCommerce brand.

Marty Smith, Partner / Talent

Margaret (D’Agostino) McDonald, Sr. Dir. Community Development & Talent Relations

Jameson Brown, EVP / Executive Editor, News Desk

Caroline Bynum, Executive Editor, Original and Social

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