#582 - Caleb Pressley

48 snips

May 14, 2025

Caleb Pressley, an engaging interviewer and creator known for "Sundae Conversations," shares entertaining insights about his break from Barstool. He humorously dives into the absurdity of a 'Mexican Easter Bunny' and age gap relationships in sports. The conversation includes reflections on independence, college sports dynamics, and the evolving landscape of content creation. With lighthearted anecdotes about tequila and personal growth, Caleb's banter captivates as he bridges the gap between humor and deeper reflections on life.

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ANECDOTE

Caleb's Independent Venture

Caleb Pressley left Barstool to run his own content company with a small team.
He continues producing Sunday Conversation and collaborates on other shows.

ANECDOTE

Theo Von's Jail Night Experience

Theo Von spent a night in jail, singing and praying without sleeping.
First night in jail requires staying alert to avoid trouble and feeling chained.

INSIGHT

Editors Are Media's Unsung Heroes

Editors play a crucial role like the hidden long snappers of media.
They take criticism without ego and shape the final product, often unappreciated.

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