Caleb Pressley and Glenny Balls Depart Barstool, Launching New Series ‘Sundae Conversation’

Caleb Pressley and Glenn Balls, the dynamic duo behind the popular Sundae Conversation interview series on Barstool Sports, are embarking on an independent journey. With Pressley spearheading this transition, he has launched his own production company, Bill Joe Productions.

This strategic shift marks a significant evolution for Sundae Conversation, which will now operate as an independent brand. Pressley will maintain ownership of the series and aims to collaborate with Glenny to produce an exciting lineup of 20 episodes in 2025.

The Motivation Behind Caleb Pressley’s Departure from Barstool

Pressley took to social media to share his thoughts on leaving Barstool, revealing his motivation through a humorous skit where he answered children’s questions. He stated, “Sometimes in life you got to take some risks and you’ve got to go out on your own and do your own thing.” He also reflected on his long tenure, saying, “I’ve been at Barstool for forever, they hired me in college, but my contract is up and, it’s time.”

View this post on Instagram

A post shared by Caleb Pressley (@calebpressley)

Glenny Balls also expressed his gratitude towards Barstool in his Instagram farewell message. He highlighted the important opportunity to work closely with Pressley at Bill Joe Productions, stating, “the chance to be Employee No. 1 at Bill Joe Productions while continuing Sundaes & more is one I simply couldn’t pass up.”

View this post on Instagram

A post shared by Glen (@glennyballs)

He concluded with heartfelt thanks: “I am forever grateful for you all and of course a big thank you to ALL my best buds I’ve made at Barstool and most importantly the boss man, Mr. Portnoy.”

Beyond the continuation of “Sundae Conversation,” Pressley is excited to explore new content avenues through Bill Joe Productions. Notably, this new venture will also collaborate with Tom Brady’s agency, Shadow Lion, focusing on “sales and talent production” for the Sundae Conversation series.

According to The Hollywood Reporter, Pressley’s decision to leave Barstool stems from his aspiration for increased creative autonomy and the chance to broaden his content production beyond the limitations of a single platform.

Commenting on this partnership, Gilad Haas, co-founder of Shadow Lion, remarked, “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.”

Source & Images