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Caleb Pressley is leaving Barstool Sports, it was announced on Wednesday. The media personality will be taking his show Sundae Conversation with him as he goes independent and forms his own production company.
According to business writer Caitlin Huston of The Hollywood Reporter, “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.”
“In today’s dynamic media world, Caleb stands out as an unparalleled talent. We’re thrilled to partner with him and Bill Joe Productions to take ‘Sundae Conversation’ to new heights, while collaborating on new, bold ideas that push creative boundaries,” said Gilad Haas, co-founder of Shadow Lion.
Caleb Pressley, 32, and his sidekick Glen “Glenny Balls” Medoro shared the news, sort of, in their usual manner with a comedic, nonsensical video on social media.
CHAPTER 2 📕 pic.twitter.com/OSeXzvWrC8
— CALEB PRESSLEY (@calebpressley) January 7, 2025
Pressley, who first gained national attention when he went from a walk-on backup quarterback at the University of North Carolina to an assistant manager role with the team and given the unofficial title of “Supervisor of Morale.”
Since beginning the popular Sundae Conversation series, Caleb Pressley has interviewed numerous celebrities including Morgan Wallen, Drew Barrymore, Post Malone, Ric Flair, Cardi B, Rick Ross, Stephen A. Smith, Ed Sheeran, Ice Cube, Joe Burrow, Deion Sanders, and Drake.
Sundae Conversation has over 933,000 subscribers, and, according to The Hollywood Reporter, has gotten over 328 million views on YouTube, with episodes averaging 10 million views across all social media platforms.
It was also noted that Pressley recently launched Chica Chida, a peanut-butter flavored spirit. He will also be appearing as the host of Druski’s original series, Coulda Been Love, which premieres in February.