Barstool Sports host Caleb Pressley is leaving the digital media outlet to strike out on his own with the help of Tom Brady’s agency for his Sundae Conversation series.
Pressley announced on social media that he is closing the Barstool Sports chapter of his professional career in an effort to go independent.
In a separate video, Glenny Balls — the Barstool Sports personality who frequently joins Pressley for the conversations with prominent figures — announced he will also exit the digital media company founded by Dave Portnoy and join the new venture with Pressley.
He’ll now produce and distribute all of his content through a recently launched company named Bill Joe Productions in honor of his father.
That new production company will work with Shadow Lion, the creative agency formed by former NFL star Tom Brady, for sales and production of his popular series.
“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 Shadow Lion co-founder Gilad Haas.
The Sundae Conversations — a play on the former SportsCenter segment — has been a popular one for Caleb Pressley and Glenny Balls. The short-form interviews frequently feature Pressley asking humorous questions to his interview subjects or asking questions that intend to back his subject into a corner to say something newsworthy while his co-host eats an ice cream sundae. Individual episodes often reach more than 10 million views on YouTube.
Barrett Media produces daily content on the music, news, and sports media industries. To stay updated, sign up for our newsletters and get the latest information delivered straight to your inbox.
