How an Athlete-Turned-Actor-Turned-Entrepreneur Built a $30M Bourbon Trail Hotel
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 Trail Hotel: https://www.thetrailhotel.com
Follow The Trail 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.
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He Helped Put Snowboarding on the Olympic Stage, Directed Shows for the Cartoon Network, and Turned Caravan Outpost into a Celebrity Magnet
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.
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How a Harvard MBA Became an Ai-First Hotelier
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.
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How He Became Hospitality’s Most Interesting Voice on Social Media: The Making of @MrScottEddy
Some people chase clout. Scott Eddy collects humans—and turns conversations into careers. He’s the guy who can turn a DM into a deal, a walkthrough video into a booking, and a dinner into a decade-long partnership. He doesn’t posture. He shows up. Early.
Today, I’m joined by Scott—hard to label by design. A Wall Street closer who hates the word "expert." A self-proclaimed non-golfer in a loud shirt who lives in airports, hotels, and on cruise ships. An early Twitter force who became a breaking-news signal from Bangkok…and then built one of Asia’s first hotel-focused digital agencies before most brands could spell "SEO."
Scott’s story pivots on a single, life-bending moment. He grew up destined for the police academy—until his father was killed in the line of duty weeks before graduation. A decade in finance followed, a firm sale cracked the door open, and a one-way ticket to Thailand blew it off the hinges. Eleven years later, with friendships stitched across Asia, he’d learned the playbook most Western brands skip: brand building starts with humility, and trust is earned at dinner tables, not in boardrooms.
Back in the States, Scott doubled down on what actually moves the needle: reply to every comment, post consistently without trend-chasing, flip OTA guests to direct, and treat service—not tech—as the last true luxury. If you run an independent property or lead a hospitality team, this is a masterclass in building gravity one honest interaction at a time.
Whether you’re building a boutique brand, leading a marketing team, or just love a good "how did they pull that off?" arc, this episode will reframe how you think about social, service, and the business of being unmistakably human.
Connect with or follow Scott
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.
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What Ian Schrager, Andre Balazs & Philippe Starck Taught Her About Hotels That Feel Different (with Erin Hosler)
Picture this: a candlelit living room in New York, a guest list cast like a film, and a host who knows exactly who should meet whom—and why.
That’s Erin Hosler. Before she checks a rate code or a P&L, she curates people.
She trained at The Ritz-Carlton before the Marriott acquisition. Learned stagecraft under Ian Schrager. Honed the five-senses playbook with Andre Balazs. Sharpened her eye alongside Philippe Starck. Then led chapters at The Standard Spa, Miami Beach; THE WELL in New York; Eaton DC; and Soho House Austin.
Her take is simple: the last real moat isn’t marble or mixology. It’s training.
Why this matters for independents:
Turn choreography into rituals your team can actually repeat.
Make being known beat being “bonvoyed.”
Design around human behavior, not developer spreadsheets.
Let tech automate the admin—never the moment.
We’ll talk membership energy and that feeling of “home on demand,” then get painfully practical—guest history, uniforms that fit, and managers who coach.
If you’ve ever wondered how a latte placed at the right table, at the right time, by the right person can outperform any brand campaign—this one’s for you.
Alright friends, without further ado, get ready to meet Erin.
Connect with Erin on LinkedIn: https://www.linkedin.com/in/erinhosler/
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.
Welcome to Behind the Stays — a podcast that shares the stories behind your favorite boutique hotels, short-term rentals, and hospitality brands and the hosts, operators, and entrepreneurs who’ve brought them to life.
Every Tuesday and Friday you’ll meet the military veterans, retired flight attendants, tech entrepreneurs, school teachers, single moms, hoteliers, and real estate investors who are all, in their unique ways, shaping the future of travel and hospitality.
Discover how these visionaries — from all over the world — have built stunning landscape hotels in the mountains, designed bohemian bungalows on the beach, erected eclectic off-grid and nature-immersed escapes, and so much 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.
Behind the States is hosted by Zach Busekrus, Head of the Journey Alliance.
Ireland