In this episode, legendary professional skateboarder Steve Caballero joins the podcast for an in-depth conversation about his storied career and life beyond the board. Steve reflects on his early childhood in San Jose, the transition from BMX to the world of professional skateboarding, and his role in the "third generation" of skaters that defined the 1980s.

Cab shares the technical origins of the "Caballerial" and offers a rare look into the inner workings of the Bones Brigade and the impact of early skate videos. Beyond the technicality of vertical skating, he opens up about the "hidden hours" of his creative process—from his evolution into art and music, to the mental discipline required to overcome self-doubt and longevity in action sports. The discussion also dives into his personal life, covering his relationship with faith, parenting, and his newfound passion for riding motocross.

Whether you’re a lifelong fan of the Bones Brigade or looking for insights on discipline and humility, this episode provides a comprehensive look at one of skateboarding's most enduring icons.