Why Is Caleb Pressley Leaving Barstool Sports?

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As a devoted fan of Barstool Sports, I can’t help but wonder why Caleb Pressley is departing the company. His charisma and insightful interviews on Sundae Conversation have always been a highlight, so his decision to leave has left many of us curious about his future endeavors.

Here is everything you need to know about Pressley’s exit from the popular blog website.

Here’s why Caleb Pressley is leaving Barstool Sports

Caleb Pressley is leaving Barstool Sports to start his own production house.

In a creative approach, Pressley shared his decision on social media via a skit involving questions from children. Essentially, he conveyed that sometimes it’s necessary to step out of your comfort zone and pursue your own ventures – a sentiment he expressed as taking calculated risks. He also thanked Barstool for providing him an opportunity during college, but clarified that his contract with them has now concluded.

Caleb Pressley is venturing out on his own to establish a new production company called Bill Joe Productions. According to The Hollywood Reporter, he aims to produce content free from the constraints of a singular platform.

As a gamer, I’m excited to announce that I still hold the rights to the Sundae Conversation, which will now be streaming under my new firm. My trusty co-host, Glenn Ball, has also decided to leave Barstool and join me in this venture. Together, we’ll be producing and planning for a total of 20 episodes this year! Stay tuned for more updates on our show.

In a goodbye message on Instagram for Barstool, he announced a fresh chance presented by Mr. Pressley, where he becomes the first employee at Bill Joe Productions, all while still managing Sundaes & more. Such an opportunity was too tempting to ignore.

Alongside Caleb Pressley, the creative agency known as The Shadow Lion (headed by Tom Brady), will team up for projects like Sundae Conversation and new material. Moreover, the pair of production companies are intending to join forces with Underdog Fantasy to develop a sports-themed series.

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2025-01-15 13:10