A staple of Barstool Sports is on the move, with Caleb Pressley announcing that he’s leaving the company.
According to The Hollywood Reporter, the former North Carolina walk-on quarterback is starting his own production company, Bill Joe Productions, where he will continue his popular Sundae Conversation interview series. While independent, Pressley’s newly formed company will partner with Tom Brady’s creative agency, Shadow Lion, on sales and talent production for the series, with the two also teaming on a sports series in collaboration with Underdog Fantasy.
“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,” Shadow Lion co-founder Gilad Halas said, according
In typical Pressley fashion, he announced his departure with a video skit in which he symbolically closed the first chapter of his career while reading to a classroom full of elementary school students. Fellow Barstool Sports personality Glen “Glennyballs” Medoro is also featured in the video and will be joining Pressley in his new venture.
CHAPTER 2 📕 pic.twitter.com/OSeXzvWrC8
— CALEB PRESSLEY (@calebpressley) January 7, 2025
Pressley first received national attention in the mid-2010s for his role as the North Carolina football team’s self-appointed “Supervisor of Morale.” He joined Barstool Sports in 2015 after founder Dave Portnoy offered him a job during an interview and he proceeded to tour college football tailgates and appear on a variety of podcasts, including The Yak and The Caleb Pressley Show.
The 32-year-old Pressley, however, is best known for Sundae Conversation, the satirical interview series that has featured several high profile celebrities, including Drake, Josh Allen, Cardi B, Shane Gillis, Post Malone, Ed Sheeran, Joe Burrow, Kirk Herbstreit and Stephen A. Smith. According to THR, the Sundae Conversation YouTube page lays claim to more than 328 million views on YouTube, with episodes averaging 10 million views across all social media platforms.
Pressley’s departure from Barstool comes weeks after now-former Plan Bri Uncut cohost Grace O’Malley announced she was leaving the company, in what she emphasized was “not a mutual decision.”
