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Chase Mitchell is a TV writer who has written for The Tonight Show Starring Jimmy Fallon. He hears a call with Chip and his dad, Billy.

Philly-bred Tommy Pope is a comedian an actor who has appeared on Comedy Central. Chip talks with his Pop, Steve, who gets in the pocket with the zen wisdom of a top coach.

Matt Nedostup is a writer at TruTV, former Senior Editor at Someecards, and stand-up comedian. He hears a call with Chip and his brother Nick.

Ashley Bez is an actress and writer that has written for the TV show Younger and is a former editor at Someecards. She hears Chip interview her sister, Elizabeth.

Mike Hall is an anchor on the Big Ten Network, and the host of Sports Lite who also spent three years as an anchor with ESPN. Mike hears Chip's interview with his dad, Jim.