Brad Steward didn’t just ride snowboarding’s first wave—he helped make it. As a teenage builder-rider-organizer, he pushed the sport from outlaw to organized, working alongside Jake Burton and Tom Sims, lobbying the Forest Service when resorts said no, and helping pave the path that led to Nagano. He co-founded one of the early camps where an eight-year-old Shaun White showed up—years before the world knew his name.

Then Brad jumped lanes: into the Spike Jonze era of skate-culture filmmaking—directing spots for Cartoon Network (Powerpuff Girls), Adult Swim, AMC, and music work that had him shooting bands like Soundgarden and collaborating with UK labels. Today, his canvas is hospitality: Caravan Outpost in Ojai—a film-set-caliber, not-glamping hideaway that’s hosted The Bachelor and a steady stream of celebrity regulars.

Today on the show, I’m joined by Brad Steward—snowboarding’s early architect, director/producer, and co-founder of Caravan Outpost.

In this episode, we cover:

How Brad helped move snowboarding from trespass to televised, shoulder-to-shoulder with Jake Burton and Tom Sims—and why the Nagano moment mattered.
How an eight-year-old Shaun White landed at his camp—and what that signaled about the sport’s future.
How the Spike Jonze pipeline turned a DIY camera habit into gigs with Cartoon Network, Adult Swim, AMC, and major-label music videos.
Why Caravan Outpost is “production design for memory-making,” not glamping—and how it became a magnet for celebrities and The Bachelor.
The throughline: build the culture first, then build the brand.

Connect with Brad on LinkedIn

Visit Caravan Outpost’s website to book and learn more

Behind the Stays is brought to you by Journey — a first-of-its-kind loyalty program that brings together an alliance of the world’s top independently owned and operated stays and allows travelers to earn points and perks on boutique hotels, vacation rentals, treehouses, ski chalets, glamping experiences and so much more.

Your host is Zach Busekrus, Head of the Journey Alliance. If you are a hospitality entrepreneur who has a stay, or a collection of stays with soul, we’d love for you to apply to join our Alliance at journey.com/alliance.