Steve Olson honed his skateboarding expertise sneaking into swimming pools across Southern California while growing up in the 1970s. His skating was wedded to a surf-centric childhood at a time when the crossover between the two was at its height. Olson earned a sponsorship by Santa Cruz Skateboards in 1979 and quickly became notorious for introducing a punk rock aesthetic and cool defiance to the skate scene. He’s also lived outside of surf-skate norms as an actor, artist, musician, and father, blending all those interests into a singular personality. In this episode, Olson sits down with Jamie Brisick to talk about their first encounters, his contemporary art practice, the art of trespassing, the surf-skate connection, cat-and-mouse thrills, his greatest moments on a skateboard, extreme individualism, and the memories that have stuck with him.