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.

• 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.

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.

• 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.

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 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.

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.