ANDIAMO - Mike Weiss

Co-Founder & Co-CEO at Trailborn and Castle Peak Holdings

Before Trailborn and Castle Peak, you worked across investment banking, real estate private equity, and several startups, from Compass to RISE Brewing to Maple. What inspired you to pivot toward hospitality?

Starting Trailborn Hotels & Resorts and Castle Peak Holdings was a natural evolution of everything I’d worked on up to that point. I’ve invested in hotels, worked at Airbnb in its early days, and created a more seamless real estate experience during my time at Compass. At Rise and Maple, I focused on developing great F&B products and experiences that connect people through hospitality. In many ways, there’s been a real estate and hospitality component of every chapter of my career–and Trailborn brings it all together. We saw an opportunity to elevate the way people experience extraordinary outdoor destinations by bringing design-forward, high-touch hotels to places that have never had them before.

Trailborn promises that guests will leave with “new stories to tell.” What makes a journey unforgettable in your eyes, and how do you design for that?

A truly memorable stay is about more than where you sleep or where you go–it’s about the experiences that stay with you. The scent of salt air after learning to surf in Wrightsville Beach. Your daughter’s laughter as your daughter rides a horse through the Rockies for the first time. The golden light, the warmth, the shared stories that linger long after. At Trailborn, we design for those moments. Every element–from the interiors and gathering spaces to the activities and amenities–is intentionally crafted to bring people together and connect them to the beauty of the place.

Trailborn’s mission feels deeply personal, it’s about reconnection, nature, and storytelling. Was there a specific trip or place that first made you fall in love with the outdoors?

Growing up, my family took annual ski and snowboard trips. We’d travel to different mountain towns across the country, chasing fresh snow and time together. I remember waking up with the sun to catch the first tracks, the quiet stillness of the slopes before the day began, and the way the mountains seemed to stretch endlessly around us. In the evenings, we’d soak in outdoor hot tubs and enjoy fun meals as a family. Those trips sparked a lifelong love of nature–the beauty, the freedom, and the way being outside connects you to the people you’re with and the place you’re in.

Your portfolio spans from Route 66 roadside hotels to spa hideaways in the Blue Ridge Mountains. How do you maintain a cohesive brand identity while celebrating each location’s individuality?

Trailborn’s identity is unified by a belief that beautiful, inspiring design should be accessible in extraordinary outdoor destinations. Each property reflects that core philosophy and follows our brand standards. We maintain the same quality, brand pillars, and experiential design no matter the destination, while leaving room for localization in the execution and implementation.

Last year, Trailborn entered a long-term strategic agreement with Marriott International as part of its new Outdoor Collection. How do you see this collaboration redefining what outdoor hospitality can look like in the years ahead?

As a founding member of the Outdoor Collection by Marriott Bonvoy, Trailborn remains proudly independent while gaining access to millions of travelers through Marriott’s global network. Such a strategic agreement that amplifies our mission to make elevated, nature-driven hospitality more accessible. We’re redefining what it means to stay close to the outdoors, combining thoughtful design, exceptional food and beverage, and curated experiences like guided hikes, surf lessons, and fly fishing. Together, Trailborn and Marriott are shaping a new category of outdoor travel that blends comfort, authenticity, and adventure.

You’ve said your team actually embeds itself in the communities where you invest. How does that level of involvement help you see potential differently?

Our approach begins with a deep respect for each destination. Before we start designing anything, we spend time on the ground getting to know the people, the culture, and the rhythm of daily life. This helps us understand not just what travelers seek, but what the community values. When we build something the community loves, it naturally becomes “of the place” — locals frequent our restaurants, bars, and events, and often become our biggest advocates, sharing Trailborn with others. To strengthen that connection, we also partner with local guides and businesses to lead excursions and deliver authentic on-site activities.

The Keep Extraordinary initiative donates a portion of every stay to local land conservation. What inspired that model, and how do you ensure it creates measurable impact in the communities you operate in?

Our goal–and one of our greatest responsibilities as stewards of the land–is to leave every place better than we found it, so future generations can experience our markets as our guests do today. Through our Keep Extraordinary initiative, a portion of every reservation booked directly on our website is donated directly to conserving and protecting the landscapes our guests come to enjoy.

What is your favorite Bellino product and why?

We’re big fans of Bellino’s BOND line because it strikes the perfect balance between luxury and practicality. The linens have an elevated look that aligns with our hotels’ design standards, but they’re also incredibly adaptable, resisting wrinkles across a variety of laundry setups. That flexibility is key for us, since many of our properties are located in rural or outdoor destinations where laundry capabilities can vary.

Castle Peak’s recent $315 million raise sets the stage for Trailborn’s continued expansion into extraordinary outdoor destinations. What’s the dream project or location you can’t wait to bring to life?

It’s been an incredible year of growth, with five Trailborn properties already open and more on the horizon in Mendocino, California, and Jackson Hole, Wyoming. Jackson, in particular, is a dream market. With its proximity to Grand Teton and Yellowstone National Parks, world-class skiing, and rich culture, it perfectly embodies what Trailborn stands for. We’re currently transforming our forthcoming Jackson Hole property into a four-star mountain retreat that balances design, adventure, and connection. It will become our first true ski destination, complete with reimagined dining, family-friendly amenities, and spaces that bring people together after a day outdoors.

Hospitality is, at its heart, about people. What’s a moment with a guest, a team member, or a local community that’s stayed with you personally?

One of the best parts of this work is being surrounded by people who instinctively step up when it matters most. That spirit was on full display when Hurricane Helene hit Western North Carolina shortly after opening Trailborn Highlands in September 2024. Our team immediately jumped into action–protecting our guests, safeguarding the property, and finding ways to support the local community. Moments like that test you, but they also bring out the best in people. Whether it was battening down the hatches together during a once-in-a-thousand-year storm or sleeping in the back of a truck when flooding left colleagues stranded, everyone looked out for one another. It reminded me that great hospitality starts with great people–the kind who show up, work hard, and care deeply.

Outside of work, what activities or hobbies bring you joy and help you recharge?

I love getting outdoors as much as possible, especially hiking with my wife and two daughters, whether it's the trails near my home or Trailborn’s properties. Highlands, North Carolina, is one of my favorite areas to hike, with its moderate summers, gorgeous autumns, and incredible views of the Blue Ridge Mountains. I’ve also golfed and snowboarded for many years, and that’s always been a great way to get outdoors, recharge, and clear my mind. 

Who has been your biggest inspiration throughout your career?

My dad has always been my biggest inspiration. He was a successful entrepreneur and company builder who achieved a great deal professionally. While he wasn’t in hospitality, he loved what he did and excelled at it. Most importantly, he managed to do it all while being an exceptional husband, father, friend, and person. 


What advice would you give to someone new to the hospitality industry?

Hospitality is equal parts creativity, operations, and human connection. My advice is to stay flexible and curious. Every property, guest, and market will teach you something new if you’re willing to learn. At Trailborn, no two projects are the same, and that’s the beauty of our brand. Building something meaningful requires resilience, collaboration, and a genuine passion for creating experiences that matter and provide memories that last a lifetime. If you lead with that, everything else falls into place.