Childhood friends turned hotel founders, Ben Weinberg and Mike Weiss built Trailborn from a shared belief that nature should be both inspiring and accessible. For them, adventure isn’t just a slogan but a way of life, one now woven into the DNA of their growing outdoor hospitality brand.
Honing Their Skills
Palm trees frame the exterior of Trailborn Surf & Sound
Before reuniting to launch Trailborn, both had carved out successful careers of their own. Weinberg began in a traditional finance role at Goldman Sachs, where he gained a deep understanding of capital markets before joining Alan Waxman’s Special Situations Group, and later TPG’s Sixth Street, a global investment firm Waxman cofounded after leaving Goldman. There, Weinberg refined his expertise in real estate and platform creation—a skillset that would later prove useful.
Weiss, a Cornell graduate with a degree in psychology and business, also began his career at Goldman Sachs, where he moved from investment banking to real estate private equity. He discovered an interest in building ventures when he helped launch the nonprofit Pencils of Promise. That drive led him to Stanford Business School and then to a series of high-impact roles: He was there during the early days of Airbnb, cofounded Compass, and later joined Maple, a tech-driven food delivery startup.
Taking the Leap
La Duna Paradiso restaurant at Trailborn Surf & Sound in Wrightsville Beach, North Carolina, designed by Post Company
Eventually, their desire to create something new and shared sense of adventure brought them back together. “Building a business is hard enough—there’s no reason to do it by yourself,” Weiss says. Before taking the leap, they spent six months testing their partnership, flying between New York and San Francisco to simulate working together. “For us, it was partner before idea,” says Weiss. “Businesses and economic environments evolve, but we didn’t want to change partners. We wanted to be in this together for the longterm.”
Those early months of conceptualization were a blur of long days and late nights. They remember 14-hour brainstorming sessions in an empty office, sketching concepts across a whiteboard, searching for the right white space in the market. In May 2018, their commitment solidified. Weinberg flew to New York on a Friday, and the next morning, the two found themselves in Thrive Capital’s office—thanks to an offer from founder Josh Kushner—where the seed of Trailborn officially took root. The vision: to inspire people to get outside and reconnect with nature.
“We think about Trailborn as the official hotel of the great outdoors,” Weinberg says. It’s about capturing moments like “sitting outside a cabin with no cell service with people you love, having a glass of wine, and thinking about something you don’t often think about,” he adds. “Or you’re with your wife—in my case—4,000 feet deep into the Grand Canyon at 125 degrees and it’s an adventure you’ve never had before. We’re trying to productize these moments and share it with people but keep it authentic.” Weiss adds, “The mission is to bring people to bucket list places they already know they want to go while also introducing them to new outdoor markets.”
Fast Track
A lobby seating area at Trailborn Grand Canyon, designed in collaboration with Lake Flato
By late 2023 and into 2024, their vision came to life with a string of openings: Trailborn Rocky Mountains and Trailborn Rocky Mountains Outpost in Estes Park, and Trailborn Highlands in North Carolina. “To call it chaos is an understatement,” Weinberg says. “It’s a special type of chaos. It’s fun and exciting, and you’re figuring out things you can’t possibly simulate.”
Since those debut properties, Trailborn’s momentum has only accelerated. The brand now boasts five properties—including Trailborn Surf & Sound in Wrightsville Beach, North Carolina and a location at the Grand Canyon that launched this year—with two more underway in Mendocino, California and Jackson Hole, Wyoming.
The company has grown to more than 40 corporate team members and several hundred on property, with offices in Park City, Utah and New York. Yet, Weiss and Weinberg remain deeply involved. “We are largely in an analog business in a digital world,” Weinberg notes. “You have to be there on property. Mike and I are on the road every week making sure the business plan, culture, and guest experience is there.”
Designing Connection
The lobby at Trailborn Highlands, with interiors by LOVEISENOUGH
This hands-on attention carries through every aspect of Trailborn’s identity, from design to programming. Each project begins internally, with Weiss and Weinberg developing a concept before partnering with design firms like Post Company, Electric Bowery, Lake Flato, and LOVEISENOUGH.
“We don’t use the same designer for everything, and we felt this was important for what we’re trying to create, which is something that feels localized,” Weiss explains. As a result, each hotel feels rooted in place, from the relaxed coastal interiors in Wrightsville Beach to the warm, earthy palette and local craft that defines the Highlands property.
Programming is equally thoughtful, made up of meaningful, site-specific experiences like morning yoga, Nordic spa rituals, and forest bathing to surf lessons and night sky packrafting. “Making the outdoors approachable has always been important to us,” Weiss points out. “The way we define the outdoors is bringing people to destinations where they can take a step back and experience something beautiful. It doesn’t need be hardcore, and we try to work that into our programming and the way we design our properties.”
A signature across each property is Après Hour, a nightly gathering where guests are invited to raise a glass, share stories, and connect. It’s about “bringing people together in a way that is natural and authentic,” says Weinberg. Such programming reflects their constant drive to improve the guest experience. “There has to be an openness to complete and total failure,” he adds. “We’re trying to take a shot on goal every time someone checks in—to create a memory they hold onto for the next 50 years. To expect to deliver that for every guest, every day, is unrealistic. But to take a shot at that every time is a powerful thing for us, and we care about it a lot.”
Built to Last
Highlands Supper Club at Trailborn Highlands in North Carolina
Much of their success stems from their dynamic as partners. Weiss is measured and analytical, while Weinberg is more forward-leaning, creating a balance that’s just right. “Figuring out how to work with someone is an art,” says Weinberg. “We work 15 hours a day, with a group of people who are enormously committed to our business, and figuring out how to work together—when to push each other and when to apologize—builds trust and foundation,” Weinberg adds.
Now, with its portfolio growing, the company continues expanding its reach through a longterm agreement with Marriott, one that has evolved into a partnership positioning Trailborn as a founding partner of the new Outdoor Collection by Marriott Bonvoy. “We have the largest hotel company in the world saying they like our product,” says Weiss. “To be a part of that is a huge validation for us and all the work that our team has done.”
The pride runs deep. “It’s personal,” says Weinberg, reflecting on the journey. “I feel a strong sense of loyalty to our team, who work so hard on what we set out to create.” Weiss echoes the sentiment: “I feel tremendous pride every time I step into our office or onto a property and see the vision we had five years ago happening in front of us. To be able to show my [family] and say, ‘This is what we created’—those moments are where I’m most proud.”
The lobby at Trailborn Surf & Sound
The retail market at Trailborn Grand Canyon
A guestroom at Trailborn Surf & Sound
An outdoor firepit at Trailborn Highlands
Trailborn founders Ben Weinberg and Mike Weiss are Boutique Design’s 2025 Up-and-Coming Hoteliers, and will be celebrated at the Gold Key Awards gala on November 10th in New York. Purchase tickets now!
