REPORT: One Of The Most Popular Barstool Sports Personalities Is Leaving To Launch His Own Production Company

One of Barstool Sports’ most recognized and beloved personalities is leaving to begin his own production company.

According to a report from Caitlin Huston of The Hollywood Reporter, Barstool Sports “Sundae Conversations” host Caleb Pressley is taking his show and leaving to start a production company. The 32-year-old will get a significant boost off the bat, as he’ll work with Tom Brady’s Shadow Lion agency.

The former North Carolina Tar Heels walk-on quarterback joined Dave Portnoy’s company after graduating in 2015. After hosting several other podcasts/programs, Pressley began hosting “Sundae Conversations” in 2021.

More from Huston:

“Starting this month, Pressley will produce and distribute all of his content, including Sundae Conversation, through his newly launched company Bill Joe Productions. Pressley will partner with Tom Brady’s creative agency, Shadow Lion, on sales and talent production for Sundae Conversation.

The two will also work together on a sports series in collaboration with Underdog Fantasy.”

THANK YOU BARSTOOL 🏴‍☠️

Thanks to my coworkers, the Stoolies, and @stoolpresidente for believing in me and giving me opportunity after opportunity after opportunity pic.twitter.com/yGtEeBNlLy

— CALEB PRESSLEY (@calebpressley) January 7, 2025

A former high school star athlete, the long-tenured Barstool Sports employee attended UNC from 2010 to 2013. He saw some action in the Tar Heels’ 66-0 victory over Idaho on Sept. 29, rushing the ball twice in the contest.

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Pressley left UNC to attend the University of Edinburgh overseas in Edinburgh, Scotland. He was subsequently added to the Tar Heels’ football coaching staff, holding a position called “Supervisor of Morale.”

Another Notable Talent Departs From Barstool Sports

Like any major sports media company/website/network, Barstool Sports has seen several notable talents depart over the last couple of years. Just last January, longtime CEO Erika Ayers Badan resigned and became the new CEO of Food52.

Amid rumors of tension with her Barstool colleagues, “Plan Bri Uncut” co-host Grace O’Malley left the company in December. Now, Portnoy and company have a giant void to fill with Pressley deciding to take his talents elsewhere.

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