#248: From Pro Snowboarder to Hospitality Innovator | with Bradley Steward
Thu Feb 05 2026
How does a pro snowboarder become a hospitality innovator?
Join David Millili and Steve Carran as they sit down with Bradley Steward, Co-founder and President of Caravan Outpost, to explore an extraordinary journey from professional snowboarding to creating one of America’s most unique boutique hospitality experiences.
In this episode, you'll discover:
The transition from sports to media, directing projects for Cartoon Network, Adult Swim, and even influencing early Jackass.How he co-founded Bonfire Snowboarding, turning it into a global apparel brand before selling to Adidas.The inspiration behind Caravan Outpost, and how he and his wife designed it as an experiential travel destination, blending luxury, community, and the outdoors.Tips for independent hoteliers and entrepreneurs on creating a brand that fosters emotional connections rather than just products.Get ready for candid stories, unexpected adventures, and behind-the-scenes moments from snowboarding competitions, Hollywood projects, and a luxury outdoor retreat that feels more like a community than a hotel.
Watch the FULL EPISODE on YouTube: https://youtu.be/leosxe5M0-0
Links:Bradley on LinkedIn: https://www.linkedin.com/in/bradley-steward-7b829a23/Caravan Outpost: https://caravanoutpostojai.com/
For full show notes head to: https://themodernhotelier.com/episode/248
Follow on LinkedIn: https://www.linkedin.com/company/the-...
Join the conversation on today's episode on The Modern Hotelier LinkedIn page
Connect with Steve and David:Steve: https://www.linkedin.com/in/%F0%9F%8E...David: https://www.linkedin.com/in/david-mil.
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How does a pro snowboarder become a hospitality innovator? Join David Millili and Steve Carran as they sit down with Bradley Steward, Co-founder and President of Caravan Outpost, to explore an extraordinary journey from professional snowboarding to creating one of America’s most unique boutique hospitality experiences. In this episode, you'll discover: The transition from sports to media, directing projects for Cartoon Network, Adult Swim, and even influencing early Jackass.How he co-founded Bonfire Snowboarding, turning it into a global apparel brand before selling to Adidas.The inspiration behind Caravan Outpost, and how he and his wife designed it as an experiential travel destination, blending luxury, community, and the outdoors.Tips for independent hoteliers and entrepreneurs on creating a brand that fosters emotional connections rather than just products.Get ready for candid stories, unexpected adventures, and behind-the-scenes moments from snowboarding competitions, Hollywood projects, and a luxury outdoor retreat that feels more like a community than a hotel. Watch the FULL EPISODE on YouTube: https://youtu.be/leosxe5M0-0 Links:Bradley on LinkedIn: https://www.linkedin.com/in/bradley-steward-7b829a23/Caravan Outpost: https://caravanoutpostojai.com/ For full show notes head to: https://themodernhotelier.com/episode/248 Follow on LinkedIn: https://www.linkedin.com/company/the-... Join the conversation on today's episode on The Modern Hotelier LinkedIn page Connect with Steve and David:Steve: https://www.linkedin.com/in/%F0%9F%8E...David: https://www.linkedin.com/in/david-mil.