Behind the Stays

How Paul Kromidas Took Summer From Asset-Heavy to AI-First—and Built the STR Operator OS of the Future

Paul Kromidas didn’t just pivot a startup—he changed the vehicle mid-race and still pulled ahead. Summer began as an asset-heavy “own an STR without the risk” model: Summer found the house, bought it with their capital, operated it for two years, and sold it back with a book of business. It worked—until the capital stack and rate environment made venture-scale returns incompatible with real estate velocity. So Paul did the brave thing founders talk about but rarely do: he sold the homes, kept the brains, and rebuilt Summer around the software that had quietly powered V1.

That software—Summer OS, now supercharged by Sunny AI—acts like a true asset-management layer for short-term rentals. It stitches market underwriting to unit-level P&L, pipes into your PMS, flags issues before they become reviews, and guides both pros and serious first-timers from “where should I buy?” to “how do I out-operate the comp set?” It’s not a wrapper around generic answers; it’s a working analyst that shows its work.

Today on the show, I’m joined by Paul Kromidas—founder of Summer—on building tools that help operators decide, buy, and perform.In this episode, we:

• Explore why venture returns and deed-on-title don’t rhyme—and how an honest boardroom conversation led to selling the portfolio and doubling down on software.
• Discuss what an STR “asset management system” really is—linking market selection, underwriting, expense modeling, and live ops into one pane of glass.
• Explore how Sunny AI turns fuzzy intent into investable action—guiding you through clarifying questions, surfacing the right comps, and recommending markets you didn’t have on your radar.
• Discuss the difference between high-level market data and operator-grade decisions—and why posting performance back to the model is where comp-set truth lives.
• Explore who it’s for today (multi-market PMs and serious operators) and how the roadmap invites the rising class of under-20-door owners without dumbing anything down.
• Discuss the next frontier: using predictions to fix tomorrow’s dip today—so hosting feels less like firefighting and more like running a dialed business.

If you’re building a portfolio—or rebuilding your ops stack—this one will sharpen how you underwrite, staff, and scale.

How He Built Mews — And Rewired the Modern Hotel Stay (With Richard Valtr, Founder of Mews)

Richard Valtr didn’t just build hotel software—he rewired what a stay could be. Before Mews, he was designing a 60-key hotel in Prague with a brazen brief: make every guest feel five-star without hiring an army. He imagined stays like playlists—moods, moments, choices—then realized the industry lacked the pipes to power it. So he built them: an open-API PMS as the backbone for personalization at scale.

Today on the show, I’m joined by Richard Valtr—founder of Mews, hotelier-turned-systems architect, and one of the sharpest minds pushing hospitality past “heads in beds.”

In this episode, we:

• Explore how that 60-key Prague experiment became a prototype for Mews—and whether a “playlist for your stay” can actually scale.
• Discuss why the real upside may live in the 16 waking hours, and how RevPAG could nudge P&Ls beyond a bed-only mindset.
• Explore what changes when spend is posted to the guest, not the room—and whether that unlocks offers people actually want next time.
• Discuss how personalization might honor your different modes—parent, partner, road warrior—with AI helping dial convenience vs. high-touch.
• Explore what an open-by-default stack could enable—and what the future relationship between OTAs and operators might look like (and how it could benefit everyone).

Connect with Richard: https://www.linkedin.com/in/richard-valtr-79541410/

Explore Mews: https://www.mews.com/en

Connect with Zach: https://www.linkedin.com/in/zacharybusekrus/

Apply to join the Journey Alliance: http://journey.com/alliance/

 

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.

How He Built Europe’s Largest Luxury Home Collection: The Le Collectionist Story

A host who always pushes for “one last drink.” A curator who unlists homes to protect the flag. An operator who builds taste—and then bolts on logistics. That’s Max Aniort.

Max is the co-founder of Le Collectionist, a luxury home brand that chose curation over scale, local operators over generic platforms, and a repeat-guest flywheel over one-and-done bookings. He started by solving for owners—people with extraordinary homes but zero appetite for late-night texts, staffing headaches, or inconsistent standards—then expanded destination by destination, partner by partner, standard by standard.

Le Collectionist now stewards 3,000 handpicked homes across a hundred-plus destinations, but the center of gravity hasn’t changed: taste first, always. They keep a waitlist and aren’t afraid to quietly unlist a house if it drifts from the standard, because the promise is as much about who you let in as where you send them. Guests come back because the experience feels personal—an advisor who remembers the floor plan your kids loved, a fridge that’s stocked the way you actually eat, and a local team with gold-key caliber pull who can turn a last-minute whim into an effortless memory.

In this episode, we cover:

• How Max built Le Collectionist by solving owner pain first—protecting the asset with standards, service, and guests who respect the home—before ever chasing scale.
• Why the brand chooses curation over growth at all costs, keeping a waitlist and telling owners “not yet” when a property doesn’t strengthen the flag.
• How a local-first operating model, including acquisitions of destination experts, unlocks the “impossible” in places like Ibiza through a gold-key caliber concierge team.
• How service is designed to fit the house, with baseline housekeeping and thoughtful touches for every stay and à-la-carte upgrades when “hotel-like” service truly adds value.
• How a single advisor follows a family across trips as a travel PA, building deep profiles and trust that naturally moves guests between destinations.
• Why longer, rooted stays—from multi-week summers to school-year relocations—are reshaping inventory strategy, staffing, and pricing.

Connect with Max Aniort: https://www.linkedin.com/in/maxaniort/

Explore Le Collectionist: https://www.lecollectionist.com/en

Connect with Zach: https://www.linkedin.com/in/zacharybusekrus/

Apply to join the Journey Alliance: http://journey.com/alliance/

 

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.

From Pandemic Lakehouse Purchase to Building Lake.com — How David Ciccarelli is Tapping a $20B Vacation Rental Opportunity

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.

From Luxury Retreats to Building the Future of Vacation Rental Management at Gather with Andreea Grigore

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.

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.

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.

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.

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.

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Connect with or follow Scott

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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 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.