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.
--------
52:01
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.
--------
1:03:06
How to Build Hotels With a Pulse: Carolyn Schneider, Co-Founder of Casetta Hotels, on Ditching the Copy-Paste Approach
Before founding creative studio Corner Booth, Carolyn co-founded Casetta Group, the acclaimed boutique hospitality brand known for transforming forgotten roadside motels into soulful, design-forward stays that actually reflect the communities they’re in. But her journey started far from the boardroom — as a cocktail server at the Ace Hotel in New York, where she first experienced the magic of what a hotel could be when it’s built with intention and feeling.
In this conversation, Carolyn unpacks how her background in the art world shaped her creative vision, how she approaches brand-building from the inside out, and why some boutique hotels manage to feel deeply personal — while others fall flat. You’ll hear her thoughts on balancing timelessness with trendiness, her approach to embedding local artists and narratives into each property, and what she’s learning as she advises clients across the U.S. and Europe through her studio.
Plus:
The real reason the front desk might be the most important brand ambassador of all
Why copy-paste design is the death of boutique hospitality
How to create a “microcosm of the community” — even in a space you didn’t build from scratch
Her thoughts on parent brands vs. standalone hotel brands — and where Cassetta fits in
The importance of building with soul — and what gets lost when you cut the “extras”
If you’re building a hospitality brand or dreaming up your next project, this episode is a masterclass in curating space, story, and soul.
Connect with Carolyn on LinkedIn
Learn more about Corner Booth
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.
--------
52:28
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.
--------
1:00:07
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.
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