In Part Two, Bob shifts from storytelling to reflection, opening up about the lessons he learned through decades in comedy, business, and community life. He talks about humility, resilience, the grind of the road, and why chasing curiosity can change everything. This episode is filled with wisdom, heart, and the kind of perspective that only comes from a lifetime of experience.

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In Part One of our conversation with longtime Side Splitters owner Bob Jewell, we trace his unlikely path from a casual open mic to running one of Florida’s premier comedy clubs. Bob shares stories from the club’s early days—18-hour workdays, last-second remodels, and the comedians who helped shape its identity. From Ray Romano to Billy Gardell, this episode offers a funny, revealing look behind the scenes of life in stand-up.

Rob Semerano and Jessica Curtis sit down with Ray Negron—author, former Yankees executive, and one-time teenage graffiti artist whose life changed the day George Steinbrenner caught him in the act. Negron shares the extraordinary twists that took him from a Bronx holding cell to the Yankee clubhouse, where players and mentors shaped his faith and purpose. His story is a testament to second chances, gratitude, and the unexpected places where true transformation begins.