Behind the Stays

We’re live at Skift with a builder proving the future isn’t generic search; it’s purpose-built marketplaces for travelers who already know their stay type—a lake house. I’m Zach, and today I’m joined by David Ciccarelli, co-founder of lake.com. After a startup exit during the pandemic, David and his wife (and co-founder) Stephanie bought a lake house—he grew up on Lake Superior, she on Lake Erie. A few months in, they hosted a 25-person family reunion to put the place to use—and that’s when the opportunity snapped into focus: the nearby hotel was priced for peak season, and the close-enough rentals you’d want for a shared trip weren’t surfacing. Conversations with local trades who service waterfront homes confirmed the pattern—plenty of beautiful, generational places sitting unused most of the year.   Instead of optimizing for everyone, David optimized for the traveler who already knows the experience they want. He acquired lake.com, built discovery around thousands of lakes and parks, and set a simple rule—on the water or within 15 minutes—so results stay on-vibe. On the back end, he scaled supply by integrating directly with property management systems so calendars and pricing stay in sync; on the business side, he kept incentives clean with shared success (a flat commission only when hosts get booked). The result: a fast-growing, lake-first inventory measured in the tens of thousands. In this conversation, you’ll hear: How that reunion turned a personal headache into a thematic OTA Why curated, stay-type discovery beats generic search in a GenAI world The domain-as-distribution bet behind lake.com The PMS integration play that actually scales supply (and prevents double bookings) What “within 15 minutes of the water” does for expectations, filters, and conversion   Explore Lake.com at, you guested it... www.lake.com ;) Connect with David on LinkedIn: https://www.linkedin.com/in/davidciccarelli/   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.

It’s 2008. The financial world is crumbling, Wall Street is bleeding jobs, and a brand-new finance grad named Andreea Grigore is staring down a recession with no clear path forward. Then, at a birthday party in Montreal, everything changes. She meets the founder of Luxury Retreats, one of the world’s first platforms for high-end villas, private islands, and over-the-top vacation rentals. A casual conversation turns into an unexpected offer — and what was supposed to be a stopgap job becomes a nine-year masterclass in luxury travel, entrepreneurship, and scaling a global brand that Airbnb would eventually acquire to form its Luxe division. Fast forward, and Andreea is now the CEO of Gather Vacations, a company reshaping the playbook for property management. Instead of asking local managers to give up their independence, Gather powers them with the back-end systems, tech, and support they need so they can focus on what matters most: homeowners and guests. In this conversation, you’ll hear: How a recession detour became a once-in-a-lifetime break into luxury hospitality The inside story of scaling Luxury Retreats and watching it become part of Airbnb Luxe Why Hawaii was the perfect test bed for rethinking property management How Gather’s model challenges the franchise status quo and sets a new standard for partnership What the future of vacation rentals looks like when brand, consistency, and local expertise collide   Explore Gather Vacations: https://gathervacations.com/staff/andreea-grigore/ Connect with Andreea: https://www.linkedin.com/in/andreea-grigore-081a6418/   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.

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.

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.

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.

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.

Some people chase opportunities. Ben Uyeda manufactures them from thin air. He’s the kind of mind who can turn a single YouTube video into a global audience, a shipping container into a home, and an empty stretch of desert into a 65-room design-forward hotel. His career isn’t a straight line — it’s a series of bold leaps, each one bigger and riskier than the last. Today, I’m joined by Ben — a man who defies simple titles. He’s an architect who never got licensed… yet co-founded an award-winning design firm. A YouTube creator who has racked up millions of views… yet never set out to be an influencer. A DIY experimenter who built his first video around making a vase… and somehow found himself co-developing the first ground-up hotel in Joshua Tree in over a decade. Ben’s story is one of intentional pivots and unexpected escalations — the kind that start with a single idea, and through grit, ingenuity, and a willingness to share the messy middle, grow into something extraordinary. From sustainable design classrooms at Cornell to steel-frame modular hotel rooms shipped from Canada to the California desert, his career reads like a blueprint for blending creativity with entrepreneurship. In our conversation, we cover: How prolific demonstration of process can be more powerful than perfection — and why that’s catnip for potential partners. Why sharing “warts and all” content beats polished mystery every time. The real reason most ambitious hotel projects in Joshua Tree fail — and how patience and risk tolerance become the ultimate competitive advantage. The economics of design decisions, and how a $6,000 bench became a $900 triumph. Why the future of hospitality may mean curating less, not more — and creating spaces for reflection instead of constant stimulation. Whether you’re a builder, a dreamer, or just someone who loves a good “how did they pull that off?” story, this episode will make you see the intersection of design, content, and business in a whole new way. Ben’s website: https://www.benuyeda.com/ Hotel RESET website: https://www.stayreset.com/ Follow Ben on Instagram: https://www.instagram.com/benjaminuyeda/ 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.

What would possess two brothers — with no hospitality background — to open a luxury hotel in a city where no new hotel had been built in three decades? In a word: vision. In this episode, I sit down with Shamim Ehsani, co-founder of Tribe Hotel and one of the most intentional hoteliers I’ve ever met. What started as a need for a conveniently located place for business travelers became something much bigger — a cultural reset for what luxury means in Kenya. We dive into: Why Tribe wasn’t designed to mimic what was trendy abroad — but to reflect the energy of modern Nairobi How art, music, fashion, and food became the foundation of the brand’s identity The unexpected call from Design Hotels — after they initially said “not interested” What today’s travelers actually want, and how his team is designing for access, not just aesthetics This episode is a masterclass in designing hotels with soul — and staying true to your vision when everyone else is playing it safe.   Connect with Shamim on LinkedIn   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.

In today’s episode of Behind the Stays, we’re diving into one of the biggest mysteries plaguing modern hospitality entrepreneurs — how do you take all that beautiful, buzzworthy content that’s racking up views on Instagram and actually turn it into real bookings? My guest today is Dustin Baker, the quietly brilliant force behind Hidden Gem Media — a performance-driven marketing agency that’s helping some of the most design-forward vacation rental and boutique hotel brands in the world unlock direct booking revenue from their social media presence. Now, I don’t say this lightly — within the last week alone, two different people in the space told me, “Zach, you need to talk to Dustin.” So we got him on the mic fast. In this conversation, we talk about the difference between content that looks great and content that converts, why creators (not influencers) are the most underutilized asset in the industry, how Dustin and his team are proving ROI on social in a way most operators didn’t think was possible, and why the real power play in 2025 might just be an email list, not a viral reel.  If you’ve ever wondered what happens after someone likes, saves, or shares your content — and how to turn that attention into actual revenue — this episode is for you.   Learn more about Hidden Gem Media Connect with Dustin on LinkedIn   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.