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

May 23, 2025

Mike Weiss and Ben Weinberg, co-founders of Trailborn, discuss their ambitious journey shifting from finance to creating an experience-driven hospitality brand. They explore the untapped potential in lesser-known markets and the benefits of vertical integration. The duo shares how their partnership with Marriott enhances their reach while maintaining their core values. They delve into the intersection of AI and personalized service, arguing that technology will elevate, not replace, the human touch in hospitality.

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ANECDOTE

Founders' Lifelong Friendship

Mike and Ben have known each other socially since childhood and reconnected as adults wanting to start a business.
They spent extensive time aligning philosophies and goals to build a strong, enduring partnership.

INSIGHT

Combining Passion with Opportunity

Passion and spotting an unmet opportunity drove Mike and Ben to build Trailborn.
They saw a clear white space in outdoor hospitality that others ignored or missed.

INSIGHT

Filling Outdoor Travel White Space

Outdoor travel demand is booming but lacks high-quality, experience-driven hotels near iconic destinations.
Trailborn aims to fill this gap by building a vertically integrated brand and management company.

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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.