The Giggs Podcast: #29 Josh Castle | “Tour Dad” - Managing Quality of Life On The Road

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Josh Castle is currently on tour with Dierks Bentley as the Quality of Life Manager, and we get into what that job really is…For over 17 years, Josh Castle has worked on some of the biggest shows in entertainment, including the Super Bowl Halftime Show, the Academy Awards, CMA Awards, and ACM Awards. His roles have ranged from production assistant to talent manager and everything in between, but no matter the title, his mission remains the same—to bring joy and improve the day of everyone around him.

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From Golf Cart Disasters to the Super Bowl Stage

Josh’s story starts at the CMA Fest—just two weeks after graduating high school—where he was a volunteer driving artists in golf carts through Nashville’s stadium tunnels. Cue a torrential storm, panicked evacuations, and one very stuck golf cart. He and three strangers had to physically lift and turn it around in a sea of steel chairs, all while chaos unfolded around them. It was embarrassing, sure, but also the beginning of a wild ride in live events.

From there, Josh worked his way through the ranks: talent wrangler, dressing room assistant, green room manager, and eventually, talent manager. He’s worked on some of the biggest shows in entertainment, including the Super Bowl Halftime Show with Beyoncé, the CMA Awards, and the Academy Awards.

The Job You Didn’t Know Tours Needed

Josh’s role as Quality of Life Manager didn’t exist until it did—coined by Dierks himself after watching Josh go above and beyond to make tough days more bearable. Whether it’s remembering someone’s favorite snack, organizing themed crew days like “Christmas in July,” or simply bringing a framed picture of Kermit the Frog to make his desk feel like home, Josh has turned the concept of hospitality into an art form.

His job blends production coordination, PA responsibilities, morale boosting, and logistics mastery. One day he’s ordering 60 burritos from Chipotle (days in advance, of course), the next he’s leading a snowball fight with plush toys after a hot summer show.

The Mental Game of Touring

Touring isn’t glamorous every day. It’s grueling: 18-hour days, three hours of sleep, constant travel. Josh shared that getting into “touring shape” starts weeks before hitting the road—early wake-ups, Peloton rides, cutting fried food (which rarely lasts once tour starts). The emotional toll is real too. When things go sideways, Josh finds a secret “rage room” in each venue to let it all out, reset, and return with a smile.

Kindness Is the Cornerstone

More than anything, Josh believes in kindness. “Kindness is free,” he says. Even when exhausted, he’s committed to making everyone from the headliner to the local venue runner feel seen and appreciated. It’s this ethos that makes him indispensable. As he puts it, “I’m replaceable, and that’s why I try so hard.”

Finding Your Spark

One of Josh’s biggest takeaways for anyone entering the touring or live event world: find a way to insert yourself into the job. What makes you unique? For Josh, it’s humor, creativity, and an innate sense of empathy. Whether it’s making parody videos or bringing Halloween decorations from home, his personal touch turns everyday gigs into something memorable.