From Search to Discovery — Inside Expedia’s Vision for an AI-Driven Travel World w/ Greg Schulze, CCO of Expedia Group
Greg Schulze has spent more than two decades helping build one of the most influential companies in modern travel — Expedia Group.
But here’s the thing about Greg — he doesn’t talk like a corporate executive. He talks like a traveler.
He’s lived and worked all over the world. He named his dog Kaya after a coconut jam he discovered while living in Southeast Asia. And he still lights up when describing what it feels like to walk through an airport on the cusp of somewhere new.
Greg’s career has spanned from American Airlines in the early 2000s to leading Expedia Group’s global commercial strategy today — a period that’s seen the birth of OTAs, the rise of mobile, and now, the dawn of the AI-powered traveler.
In this episode, Greg and I explore:
How Expedia has evolved from a dot-com upstart to a travel empire spanning Expedia, Hotels.com, and Vrbo.
What he’s learned from 20 years of guiding one of the most complex, global marketplaces in the world.
The real story behind Expedia’s relationship with independent operators — and what “partner forward” actually means.
How the tension between discovery and control will define the next decade of travel planning.
And why he believes the future of OTAs will be built not on ads or algorithms — but on trust, clarity, and flexibility.
Greg’s a global citizen in the truest sense of the word — deeply thoughtful about the human side of technology and the emotional heartbeat of travel itself.
This conversation is the second episode in my new Behind the Stays series, The Future of Travel, recorded live at EXPLORE Connect in Austin, Texas — a gathering of the world’s top vacation rental operators and hospitality leaders.
If you care about where the industry is headed — and how the people behind its biggest brands are thinking about discovery, booking, and guest experience in the years ahead — this is a must-listen.
Connect with Greg: https://www.linkedin.com/in/gregschulze/?originalSubdomain=uk
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.
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Inside Expedia’s Next Move — How Vrbo Plans to Out-Innovate Airbnb with Larry Plawsky, General Manager of Vrbo
Welcome back to Behind the Stays, presented by Journey.
This episode kicks off a special series on the future of travel — conversations recorded live in Austin, Texas, at Expedia Group’s EXPLORE Connect — a gathering that brought together some of the most powerful voices in travel tech alongside the top owners and operators of vacation rental management companies from around the world.
I sat down with several of Expedia’s most influential leaders — the folks guiding brands like Expedia, Hotels.com, and Vrbo — to unpack how they’re reimagining discovery, bookings, and experiences in an AI-powered world.
In this first conversation, I chat with Larry Plawsky, Senior Vice President and General Manager of Vrbo. And get this — this was actually Larry’s first-ever podcast interview.
Larry’s a brand builder who’s spent his career rooting for the underdog — from helping revive Old Spice back in the day to scaling massive two-sided marketplaces like Ticketmaster. And now, he’s leading Vrbo into its next chapter within the Expedia Group ecosystem.
We dive deep into:
How Vrbo plans to take on Airbnb by doubling down on trust and quality — not just scale.
The single biggest opportunity Larry sees to increase traveler confidence when booking a home.
How Expedia’s integrated network of brands — from Hotels.com to One Key — gives Vrbo a unique competitive edge.
And how AI is already reshaping discovery on Vrbo — from smart sorting and review summaries to a vision of what travel planning could look like when chat-based search meets marketplace precision.
Larry’s thoughtful, humble, and sharp — a rare mix of brand soul and analytical rigor — and in this conversation, you’ll hear exactly how one of the most iconic names in alternative accommodations plans to redefine trust and loyalty in the years ahead.
So grab your coffee, settle in, and enjoy this special conversation with Larry Plawsky, SVP and General Manager of Vrbo, right here on Behind the Stays.
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 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.
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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.
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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.
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