Michael Weiss

Michael Weiss is the Co-Founder and Co-CEO of Trailborn, a boutique hotel brand focused on outdoor destinations.12 He founded Trailborn with Ben Weinberg in 2021 through their hospitality investment and development company, Castle Peak Holdings.24

Weiss has a background in investment banking and real estate private equity.2 He attended Stanford University Graduate School of Business.1 Prior to Trailborn, Weiss worked at Goldman Sachs.3

Trailborn aims to provide experiential and design-forward accommodations in nature-centric locations, such as National Park gateway towns and beach destinations.4 The brand's first property, Trailborn Rocky Mountains, opened in Estes Park, Colorado, in 2023.4 Weiss and his team are expanding the brand, with additional locations announced at the Grand Canyon, Highlands (North Carolina), Wrightsville Beach (North Carolina), and Mendocino (California).4

Weiss emphasizes the importance of vertical integration in Trailborn's operations, allowing them to control the guest experience and align it with their vision.34 He believes in creating authentic, location-specific experiences that make guests feel part of the natural landscape.3

In November 2023, Trailborn Highlands won the Boutique Design | BDNY Gold Key Award for Emerging Hotel Concept5, demonstrating the brand's growing recognition in the hospitality industry.