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. 

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  

Additional Resources

Learn more about Castle Peak Holdings: 

LinkedIn 

Website 

Learn more about Trailborn: 

LinkedIn 

Website 

Connect with Ben 

Connect on LinkedIn 

Connect with Michael  

Connect on LinkedIn

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