Behind the Stays

How They're Building the Next Great American Hotel Brand: The Story of Trailborn with Co-Founders Mike & Ben

What happens when two childhood friends trade finance careers for a crack at building the next great American hotel brand? You get Trailborn.

In this episode, I sit down with Mike Weiss and Ben Weinberg, co-founders and co-CEOs of Trailborn — a vertically integrated hospitality brand reimagining what it means to travel to America’s most iconic outdoor destinations.

Mike and Ben didn’t just set out to build better hotels — they’re building an experience-driven brand from the ground up, one that actually reflects how modern travelers want to explore the wild. We unpack the white space they saw in markets like Mendocino, Wrightsville Beach, and Highlands, why they chose the “harder path” of vertical integration, and what it really takes to operate with excellence in places that don’t always show up on institutional investors’ maps.

You’ll also hear:

• Why building brand and operating company and real estate platform was a bet they were willing to lose sleep over
• How their new partnership with Marriott gives Trailborn scale — without sacrificing soul
• The early seeds of personalization in hospitality — and how Trailborn plans to lead with both human intuition and machine intelligence
• Why AI won’t replace great service — but it might finally deliver on it

This one’s for the founders, the place-makers, and anyone who’s ever tried to do something the “harder, but better” way.

Learn more about Trailborn

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. 

Why Vibe-Driven Hotels and Restaurants Are Failing (And What Actually Works)

Cory Schisler isn’t just building beautiful hotels and restaurants — he’s rethinking what hospitality actually feels like.

He’s worked with brands like Proper and Viceroy, co-founded The Madrona in Healdsburg, and has a sharp eye for the subtle — and not-so-subtle — ways hospitality has evolved (and where it still needs to catch up).

In this episode, we unpack:

– The early experiences that shaped Cory’s hospitality worldview
– How to balance timeless service with modern guest expectations
– The tech that actually enhances hospitality (and the kind that kills it)
– Why QR code menus might signal the beginning of the end
– What’s next: the rise of micro-resorts and the white space between STRs and hotels

Cory also shares how he approaches concept development, the difference between good and great creative partners, and what it really takes to build a team culture where guests feel seen — and staff feel proud.

This one’s packed with insight for anyone thinking about the next generation of hospitality brands.

Learn more about Cory here.
Explore The Madrona

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. 

Why Hotel Booking Engines Are Dying — And How AI Agents Will Replace Them, with Selfbook Founder Khalid Meniri

Khalid Meniri didn’t come from hospitality — but maybe that’s exactly why he was able to see its most obvious blind spot so clearly.

A designer and technologist by trade, Khalid is the founder of Selfbook, the beautifully elegant booking platform that’s quietly powering the next generation of high-end hotels.

In this episode, you’ll hear the remarkable story of how a glass cube on Fifth Avenue (yes, the Apple Store) first inspired Khalid’s obsession with design — and how years later, that obsession led him to reimagine the broken booking experience plaguing even the most beautiful hotels.

We unpack:

• Why the legacy booking flow is fundamentally broken — and why most hoteliers don’t even realize it

• How Selfbook is thinking about dynamic pricing, personalized rates, and the future of “invisible tech”

• Why the most exciting guest journeys of the next decade won’t start on a hotel website — they’ll start in a chat window

• And how Selfbook’s new partnership with Perplexity could reshape hotel discovery at the point of inspiration

If you care about hospitality tech, design-led products, or the future of direct booking, this is a must-listen.

Learn more about Selfbook

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 Sales Guy to Hospitality Media Mogul: The Modern Hotelier Story with Steve Carran

Steve Carran never set out to become one of the most recognized voices in hospitality media. But what started as a scrappy experiment to engage hoteliers during his time in sales has now blossomed into The Modern Hotelier — one of the industry’s most beloved podcasts and a new video media brand that’s putting a fresh lens on hospitality storytelling.

In this episode, you’ll hear the fascinating backstory behind how Steve and his co-host David Millili launched the podcast, how they bought it back from a startup, and how it has completely reshaped Steve’s career. We also dive into the biggest trends he’s seeing across the hotel industry — from how AI and design are converging to address labor shortages, to the rise of "bleisure" lobbies, to why apartment-style hotels like Mint House are quietly winning the loyalty of the next generation of travelers.

Plus:

- Why hotel lobbies are becoming the new coworking spaces
- How podcasts have become the secret weapon for hospitality networking
- Why giving guests a choice in how they interact with your brand is the future of service
- Steve’s vision for the Modern Hotelier Media group — including their "MTV Cribs"-style hotel video tours

If you’re building a hospitality brand or just love geeking out on where the industry is headed, this episode is for you.

Connect with Steve on LinkedIn
Listen to The Modern Hotelier

 

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 Ash Hotels Became the Coolest Brand You’ve Never Fully Defined

If you’ve scrolled Instagram or Design Milk anytime in the last few years, you’ve probably come across a hotel that made you stop scrolling. Not because it was just beautiful, but because it felt like a world. A story.

And chances are... that hotel was built by Ash.

In this episode, I sit down with Ari Heckman, founder & CEO of Ash — one of the most distinctive hospitality brands redefining how hotels, neighborhoods, and even guest memories are made.

Ari’s story is a masterclass in world-building. We explore how growing up in post-industrial Providence sparked his obsession with places that transform.

Why he didn’t study hospitality at Cornell (even though he was a stone’s throw from the world’s most famous hotel school). And how Ash went from a small design studio to an experiential powerhouse shaping properties from Baltimore to New Orleans.

We get into why modern travelers don’t just want design anymore — they want mythology, meaning, and discovery.

We unpack how Ash thinks about cinematic storytelling, why boutique hoteliers must learn to master revenue as much as aesthetics, and what Ari believes is the next great unlock for independent brands scaling today.

If you care about hospitality, placemaking, or just building things that matter — this one’s for you.

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 the Bloomberg of Travel: The Story of Skift with Rafat Ali

What if the future of storytelling isn't about bigger platforms — but sharper taste?

What if the real shift happening in media isn't just economic... but moral?

Today, you’re about to meet Rafat Ali — founder and CEO of Skift, one of the most respected travel media brands in the world. But his story didn’t start there.

Rafat grew up in India, a shy kid who stuttered — and somehow rewrote his future with nothing but words and a relentless eye for what others missed.

He went from studying engineering to working for tech media icon Jason Calacanis during the first dot-com boom...to later building Skift into a brand so trusted that today, CEOs and world leaders cross conference halls just to get a bro hug from him.

In this conversation, Rafat shares why legacy media is collapsing, what too many creators get wrong about influence, and how AI and independent media are re-drawing the map faster than most realize.

We talk about why design — not data — will be the real differentiator in the next chapter of content.

We dive into the hidden risks of "audience capture" — and why building something truly enduring requires the courage to be misunderstood for a while.

And we explore why Rafat believes the next great media empires won't be built by corporations — but by people, building with instinct, action, and radical authenticity.

If you care about the future of media, if you're trying to build anything magnetic, or if you just want a rare look inside the mind of one of the industry's true visionaries...you're in the right place.

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 Instagram Fame to Industry Change: JourneyMore, Mike Will Travel, and the Rise of Creator-Led Hospitality

When the COVID-era short-term rental boom hit, a new class of creators quietly redefined hospitality marketing — and today, three of the best in the business join me for a conversation you won't want to miss.

In this episode, I sit down with Hayden Hughes, Nicky Hughes, and Mike Iannetta — three pioneers who helped transform treehouses, A-frames, and glamp-sites from hidden gems into viral, booked-out brands. We unpack how they redefined marketing in the short-term rental world, where the future of creator-driven hospitality is headed next, and why they’ve partnered to launch a new guided course to help hospitality brands partner with the right creators.

We get into it:

• Why short-form video changed everything for independent operators
  
  
• What still actually works on social today — and why trends alone won’t save you
  
  
• Why UGC (user-generated content) isn’t enough anymore — and what’s replacing it
  
  
• The hidden burnout creators are facing, and how the next generation of hospitality marketing will be built differently
  
  
• The big opportunity no one's talking about (yet) for boutique hotels and micro-resorts
  
  
• How the best operators are thinking differently about working with influencers
  
  
• And why creators who want to build real businesses are starting to think beyond content
  
  

You'll also hear the story behind the Journey More Collective, a potential new playbook for scaling authentic creator-driven marketing and get all the details on the value of The STR Influencer Guide Hayden, Nikki, and Mike just released. 

If you're an operator wondering how to actually work with creators (the right way) — or a creator dreaming about building a business with staying power — this one’s for you.  Oh, and if you’re interested in accessing The STR Influencer Guide for Operators, you can do so in the show notes below!

Alright friends, without further ado, get ready to meet Mike, Nikki, and Hayden. 

Purchase The Influencer Guide

Connect with JourneyMore

Connect with Mike from Strive Hospitality (MikeWillTravel)

Watch a Roundtable Discussion with Zach, JourneyMore, Mike, and other Unique Stay Builders

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 joinjourney.com/alliance.

Is This the End of Direct Bookings? Everything You Need to Know About Airbnb’s New Off-Platform Policy

In this episode, I’m joined by Arthur Colker, Founder of StayFi, and Philip Kennard, CEO of FutureStay, to unpack one of the most talked-about moves in short-term rental history: Airbnb’s newly sharpened Off-Platform and Fee Transparency Policy.

Depending on who you ask, it’s either a long-overdue consumer protection measure... or a strategic power grab designed to lock in lifetime guest value at all costs.

Arthur and Philip bring firsthand insights — and a healthy dose of reality — to a conversation that’s been fueled by fear, misinformation, and a whole lot of LinkedIn hot takes.

In this episode, we dive deep into:

• Why this "new" policy might actually be less revolutionary than most hosts realize — and what’s really different this time

• The two “buckets” Airbnb is focused on: protecting guests (good) and protecting their margins (more complicated)

• How vague language, selective enforcement, and the threat of guest complaints create a new dynamic hosts must navigate

• Why operators building brands off-platform shouldn't panic — but should pay attention to regulatory winds (especially in Europe)

• What might come next: services marketplaces, tighter control over payments, and the looming specter of pricing parity

• The psychological game: How vague rules might cause small operators to self-police harder than Airbnb could ever enforce

If you’re a rentalpreneur, a professional operator, or someone who’s betting their future on brand-building in the STR world, this episode is a must-listen.

We break down not just what’s happening — but what it means for the future of independent hospitality, ownership, and guest relationships in an increasingly walled-garden world.

Because as Arthur and Philip both point out: the real battle isn’t about moving one booking — it’s about who owns the guest relationship in the long run.

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.

7 Non-Obvious Lessons Shaping the Future of Hospitality (And What To Do About Them)

In this solo episode, Zach shares seven powerful, non-obvious lessons shaping the next era of hospitality—insights drawn from conversations with some of the most forward-thinking operators, creatives, and strategists in the space.

From the rise of emotional loyalty and transformational stays to the power of digital atmosphere and placemaking over property management, this episode challenges traditional assumptions and inspires fresh thinking for hotel owners, experience designers, and anyone shaping the future of guest experience.

You’ll walk away with:

• Questions to ask your team (and yourself) right now

• Real-world examples of brands already doing this well

• Execution ideas you can implement this quarter

Whether you’re a boutique hotelier, a vacation rental operator, or a hospitality creative, this episode will push your perspective and deepen your purpose.

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. 

She Built a Luxury Resort Around the Moon — And It’s Working. This is the Story of Stellara.

You’ve heard of luxury glamping. You’ve seen treehouses and mirror cabins. But you haven’t seen anyone doing it like this.

In this episode, I sit down with Meredith Garrett — founder of Stay Minty and Stellara — to explore how she’s redefining what it means to deliver luxury in nature. You may know her for her wildly creative short-term rental brand Stay Minty, with its kaleidoscope of high-design vacation homes and glamping domes. But with Stellara, Meredith is pushing the envelope even further — into the stars, quite literally.

We discuss:

• How she transformed treehouses and mirror cabins into immersive, astrology-inspired sanctuaries that change with the moon.

• Why she believes experiential hospitality is moving from “boutique” to “transformational.”

• The math behind scaling nature-based resorts — and how many units it actually takes to make something like Stellara work.

• Whether food & beverage is the missing link in micro-resort hospitality — and her hunt for the elusive private chef who can bring lunar dinners to life.

This conversation is for the dreamers, the builders, and the operators who believe luxury can be intimate, immersive, and wildly imaginative. Meredith is one of the most creative minds in this space — and I think you’re going to leave this episode feeling more inspired (and more curious) than you were before.

Connect with Meredith
Book a stay at Stellara
Follow Stellara on Instagram 

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.