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 s...