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.
Episodes
Friday May 23, 2025
Friday May 23, 2025
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
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.
No comments yet. Be the first to say something!