Skate, Grit, and the Long Road: Jack Smith’s Cross‑Country Story

#185 - Before longboards hit storefronts and GoPros hit helmets, Jack Smith and two friends pointed a 1969 Firebird toward the horizon and skated into history. Jack Smith talks about how a simple leapfrog relay turned a wild idea into the first recorded skateboard crossing of the United States—and how that journey shaped everything that came after.We trace the arc from clay “crumble” wheels to first‑gen urethane and on to the big trucks and 70mm wheels that made 1980s distance skating faster and safer. Jack breaks down the daily cadence—early pushes, midday pool stops, evening miles—and the small-town moments that still stick: a Minnesota marquee that read “Welcome skateboarders,” a West Virginia diner that wasn’t sure what to make of three long‑haired kids, and strangers in Ohio who handed over house keys and dinner plates without hesitation. He tells the story that stays with him most: a rain delay at Yellowstone, a missed geyser, and a roadside rescue that, decades later, circled back through a single email to confirm a life saved.We also explore how purpose and technology reshaped the ride. Jack’s 2003 crossing raised awareness for Lowe syndrome after the loss of his son; his 2018 electric skateboard traverse with his wife leading a camper van turned battery swaps into a moving pit crew. Along the way, he argues for the slower road—South Dakota’s rolling Highway 212, atlas pages over pure GPS—and why the “real America” lives beyond freeway exits. Jack shares updates on his feature screenplay and novel, plans for a 50‑year retrace in an electric VW, and a shout‑out to the new generation of cross‑country pushers proving that momentum beats perfection.Hit play to learn how to design a relay that works, dial your long‑distance skate setup, and rethink what’s possible when you stop waiting for perfect conditions. If this conversation moves you, follow the show, share it with a friend, and leave a review to help more curious listeners find the road. Which back road would you choose next?To learn more about Jack give him a follow on Instagram @jack_smith_morro_bay. Want to be a guest on Journey with Jake? Send me a message on PodMatch, here: https://www.podmatch.com/hostdetailpreview/journeywithjake Xploreum connects you with authentic wilderness expeditions led by trusted local experts. Browse real adventures, book directly with experienced guides, and get $200 off your first trip using code HumanAdventure2026 at xploreum.io/humanadventure.