Why Trailborn is Betting On America’s Drive-To Destinations
Trailborn Surf & Sound Guest Room View
Courtesy of Trailborn
The Future of The Great Outdoors
Ben Weinberg and Michael Weiss, childhood friends turned business partners, are threading the needle between nostalgia and innovation with their hospitality ventures Castle Peak Holdings and Trailborn. From the beaches of Wrightsville, North Carolina to the foothills of Rocky Mountain National Park, they’re transforming three-star properties into four-star resort experiences that honor local charm.
Their approach defies conventional hospitality wisdom. Rather than imposing a rigid brand template, each Trailborn property celebrates its unique setting while elevating the standard of outdoor destinations. As founders in the “memory-making business,” they describe how they’ve leveraged demographic analysis and local relationships to create spaces where families return year after year.
Beyond their $100M investment strategy and recent Marriott Bonvoy alliance, this conversation illustrates a larger story about America’s relationship with its outdoor spaces 一 how we experience them, honor them, and create lasting connections with them. For developers and investors, it offers an inside look into discovering value where others only see dated structures hidden off the beaten path.
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“The real magic happens when you find ways to create something special, something that’s one-of-one, without spending enormous amounts of money. We’re doing that based on all the renovations we’ve done today, by bringing in design partners who are really thoughtful, and by getting into every detail and understanding what actually matters for the guests.”
Trailborn Surf & Sound - The Blockade Surf Bar
Courtesy of Trailborn
Credit: Christian Harder
About Ben Weinberg
Before founding Castle Peak and Trailborn, Ben spent his career investing in platforms and advising businesses at Goldman Sachs, TPG ($229 billion under management), and Sixth Street ($75 billion under management). He has worked on over $10 billion of transactions in commercial real estate, restructurings, private equity, and early stage equity investments. Ben is a graduate of Middlebury College. When Ben gets outside, you’ll find him hiking in the Sawatch Range of the Rocky Mountains with his wife Caroline and their son James, or fly fishing on the Eagle River. Ben is a member of the Investment Committee.
About Mike Weiss
Before founding Castle Peak and Trailborn, Mike worked in real estate private equity and investment banking at Goldman Sachs before spending the next 10 years building and operating real estate and hospitality businesses as a co-founder of Compass, co-founder of Rise, and a member of the early leadership team at Maple. He also spent time working at Airbnb in the early days while in business school. Mike is a graduate of Cornell University and received an MBA from Stanford GSB. When Mike gets outside, you’ll find him hiking with his wife Sam searching for the highest peak, or on the golf course in search of his swing. Mike is a member of the Investment Committee.
Trailborn Surf & Sound - La Duna Paradiso
Courtesy of Trailborn
Episode Outline
(6:06) The strategic separation and collaboration between Castle Peak Holdings and Trailborn
(11:56) Why focusing on memory-making drives both guest loyalty and financial returns
(15:10) How they acquired the Wrightsville Beach property through relationship-building
(17:43) Using demographic data to identify markets with untapped potential
(23:24) Trailborn Sound & Surf design decisions that transformed underperforming spaces into dynamic hubs
(35:10) The Marriott Bonvoy partnership and its distribution advantages
(44:54) The capital strategy and fundraising approach that has attracted $100M+
(48:26) A walkthrough of the four Trailborn properties and their unique market positioning
Trailborn Grand Canyon
Courtesy of Trailborn
About your host:
Atif Qadir is a licensed architect and entrepreneur, interested in solving big problems through innovation and technology. He has founded two proptech companies and a real estate development firm, building products ranging from software to workforce housing.
His work has been covered by Technology Review, The Real Deal, Commercial Observer, and Propmodo. He’s also a frequent speaker on the future of buildings and cities on popular industry podcasts and at conferences, including this past year at the Commercial Observer National DEI Conference, Yale AREA Conference, Columbia Real Estate Symposium, Open Data Week NYC and Austin Design Week.
About Michael Graves
The world-famous design firm Michael Graves is also a founding sponsor of American Building. Its namesake, the iconoclastic designer Michael Graves, FAIA was a fierce advocate for people-centric design. His work defines a generation of American architecture and includes the Portland Building, the Humana Building and the Denver Public Library. The 1st season of American Building was filmed live at The Warehouse, his historic home in Princeton, New Jersey:
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