What do a high school jock turned Danny Zuko, a lung-collapse survivor in the middle of the 2008 crash, and a bourbon-country hotelier have in common? Will Hardy.

In this episode, Zach sits down with Will — a creative entrepreneur, real estate maverick, and placemaker behind The Trail Hotel in Bardstown, Kentucky — to unpack a life defined by bold pivots, relentless grit, and audacious vision.

From sneaking into a high school audition that would change his trajectory, to flipping 800+ homes, to nearly losing it all during the housing collapse, Will’s story is a masterclass in resilience and reinvention. You’ll hear how desperation sharpened his creativity, how a hustler’s spirit turned $100 into a flipping empire, and how faith, grit, and a little bourbon fueled his latest masterpiece: a $30M boutique hotel on the Bourbon Trail that’s redefining Kentucky hospitality.

But this isn’t just a story about bricks, bourbon, and business. It’s about a man who refused to be boxed in — who chased acting gigs in LA, launched a film production company, produced a feature on Milton Hershey, and still found the courage to start over (multiple times) with his wife and kids by his side.

If you’ve ever wondered what it takes to chase audacious dreams, survive catastrophic setbacks, and build something truly lasting — this conversation will light a fire under you.Expect stories of mimosa-fueled negotiations, clown costumes that saved real estate deals, and the kind of visionary thinking that transforms abandoned Holiday Inns into Napa Valley–level destinations for bourbon lovers.

Explore The Trial Hotel: https://www.thetrailhotel.com

Follow The Trial Hotel: https://www.instagram.com/thetrailhotel

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.

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.

He grew up in the Cook Islands, left for business school, and planned on a career far from home—until a family visit collided with a national crisis. The government was broke, tourism was collapsing, and the prime minister asked him to help. Tata Crocombe wrote a recovery plan, stepped in as an accidental hotelier, and rebuilt from the ground up—stabilizing a flagship on Rarotonga and later growing a portfolio that now includes an acclaimed private-island resort on Aitutaki. Along the way, the destination rebounded from roughly 20,000 annual visitors to about 180,000, with ownership and hospitality rooted in the local community.

Today on the show, I’m joined by Tata Crocombe, owner-operator of The Rarotongan and Aitutaki Lagoon Private Island Resort in the Cook Islands—and a self-described AI-first hotelier. For Tata, AI isn’t branding; it’s throughput. His teams now co-pilot with models every day: wedding quotes that used to take three hours take thirty minutes, reservations productivity has doubled, and direct conversions are up more than 100%—millions steered from OTA commissions back to the P&L. The goal isn’t fewer humans; it’s better work for more humans. AI clears the paperwork so staff can deliver the moments guests actually remember.

We also zoom out. Tata sees leisure shifting from “bed + breakfast” to membership-style communities built around passions—outrigger canoeing today, thousands of micro-affinities tomorrow. Big flags will splinter from dozens of brands to hundreds; independents will sharpen identity; and individual properties will matter more than the mothership. Social will spark desire, AI will personalize and convert, and owner–brand contracts will get far more flexible. Underneath it all sits a broader scorecard: guest joy, staff wellbeing, operational efficiency, profitability—and being a good neighbor to the island and the environment.

Visit The Rarotongan’s website to book and learn more.

Visit Aitutaki Lagoon Resort’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.