An Interview with Ben Weinberg

The BLLA Team sat down with Ben Weinberg, Co-Founder & Co-CEO of Trailborn and Castle Peak Holdings to chat about the upcoming Boutique Hotel Investment Conference taking place on June 5 at Florence Gould Hall in NYC.

BLLA: Can you describe the journey from your experiences at Goldman Sachs and TPG to co-founding Trailborn and Castle Peak Holdings, particularly in the context of identifying the gap in the market for boutique accommodations in outdoor destinations? 

BW: Before founding Trailborn, I was fortunate enough, at Goldman Sachs and TPG, to work with and learn from a very special group of leaders and CEOs. I am, at heart, a company-builder. I spent many years observing others, and in 2021, felt the moment was right to take the leap myself and start Trailborn and Castle Peak.

I’ve always felt that life should be an adventure– from building a company, to building a family, to exploring the extraordinary natural wonders we have in this country. Several years ago, Mike and I were struck in our travels together by a whitespace in the great outdoors that we couldn’t ignore. Domestic drive-to travel and national park visitation was increasing, consumer preferences were shifting towards experiences and boutique hospitality, yet the level of design and thoughtfulness in urban markets didn’t exist in these markets. So we set out to build a brand that would bring people to these destinations, in a way that provided more beautiful and comfortable accommodations and a more thoughtful hospitality experience.

BLLA: How does Trailborn differentiate itself from traditional hotel chains, and what unique value propositions does it offer to guests seeking accommodations in America's extraordinary outdoor destinations?

BW: Trailborn is the first vertically-integrated hospitality brand that specializes in designing and operating boutique hotels with full-service restaurants and bars, exclusively located in the country’s most extraordinary outdoor destinations. 

As owners, operators, and developers, we craft every detail to create a memorable guest experience. No two Trailborns are the same– each is rooted in its distinct locale. 

For example, in the Rocky Mountains, we designed a modern mountain lodge, pulling in colors and materials from the surrounding landscape. In Highlands, we built a property inspired by the region’s wildflowers, history of quilting, and a historic log cabin. In all our destinations, we feature local brands in our retail markets and guest rooms and develop restaurant and bar concepts that reflect our locations.

Trailborn hotels are more than just places to stay. We serve as trusted adventure guides– offering custom Field Guides and exclusive experiences. Whether it's a fly fishing excursion or a mixology class, there's something for everyone. Trailborn provides a new way for travelers to experience the great outdoors.

BLLA: As co-founder of Castle Peak Holdings, what factors do you consider when evaluating potential investment opportunities in boutique hotel development projects?

BW: First and foremost, we only look for opportunities in iconic outdoor destinations. These include top-tier national parks and regional gems that millions of people are traveling to today. Specifically, we invest in markets that have high barriers to entry and in which demand is outpacing supply. 

Then it’s all about finding the right properties. All of our hotels are located in the center of the action, walking distance from lively towns and with easy access to our natural surroundings. We acquire unique properties that can be renovated and repositioned into Trailborns, with comfortable guest rooms, lively indoor and outdoor gathering spaces, and full-service restaurants and bars. The combination of these factors allows us to develop quality assets with attractive returns and set us up to scale to many more destinations.

BLLA: Given your background in conservation and climate change advocacy, how does Trailborn incorporate sustainable practices into its hotel design and operations, and how does this impact your investment decisions?

BW: Trailborn is focused on sustainability every step of the way. Instead of building ground up, we take an adaptive reuse approach to development to minimize our environmental footprint and reinvigorate historic spaces. On-site amenities and the guest experience are designed to limit waste– reducing throw-away collateral like WiFi cards, providing paper keycards, and offering fresh water refill stations. Trailborn takes a long-term approach to hospitality, reinvesting in the communities and natural environments surrounding each of our hotels. Our “Keep Extraordinary” initiative donates a percentage of every reservation to support local land conservation and preserve the great American outdoors. As our brand grows, so will its impact – with Trailborn guests playing their part in helping to preserve our outdoor destinations.

BLLA: How do you envision the future of boutique hotel investment intersecting with outdoor recreation and conservation efforts, particularly in light of Trailborn's mission and your personal passion for the outdoors?

BW: The increasing demand for outdoor and experiential travel shows no signs of slowing down, and younger consumers care more and more about protecting our planet for the future. Castle Peak Holdings’ acquisition of eight properties in the past 18 months reflects a strategic response to this trend. We’re betting on this continuing to be a compelling space for boutique hotel investment. We see this as a 25-year project to expand our portfolio and create a business that will outlive us. We love the great outdoors, we love to travel, and we believe there are many extraordinary places that everyone needs to see. 

BLLA: Why are you excited to attend the Boutique Hotel Investment Conference?

BW: I always enjoy sharing a bit about the Trailborn story and learning from our peers. I’m excited and flattered to be speaking alongside talented, innovative leaders in our space, and look forward to connecting with them at the event.

Come see Ben Weinberg speak on a panel we call “Emerging Markets and Opportunities” alongside Alex Levin of Liquid Crystal and Jason Liebman of Auric Road on June 5 at Florence Gould Hall in NYC!

Register for your tickets today!

This article was originally published on the Sincerely, BLLA blog