Building the Boutique for the Outdoors - Ben Weinberg - Co-Founder & Co-CEO at Trailborn

In this episode, Jake Wurzak sits down with Ben Weinberg to discuss the intersection of entrepreneurship, hospitality, and real estate. Ben shares his journey from investment banking into building Trailborn, a brand focused on transforming three-star properties into four-star experiences in iconic outdoor destinations.

The conversation covers the strategy behind unlevered value creation, the complexities of scaling hospitality businesses, and the importance of design, culture, and people in creating memorable guest experiences. Ben also reflects on raising institutional capital, balancing investment returns with brand-building, and the lessons learned from operating across multiple properties.

They discuss:

• How Ben transitioned from finance to hospitality entrepreneurship
• The evolution of unlevered value creation in today’s higher interest rate environment
• Trailborn’s approach to converting underperforming assets into distinctive four-star experiences
• The importance of design, unified branding, and thoughtful guest touchpoints
• Building a scalable team, culture, and reporting structure to drive growth

Links:

Ben on LinkedIn -https://www.linkedin.com/in/ben-weinberg-29644156/

Trailborn - https://www.trailborn.com/

Connect & Invest with Jake:

Follow Jake on X: https://x.com/JWurzak

1 on 1 coaching with Jake: https://www.jakewurzak.com/coaching

Learn How to Invest with DoveHill: https://bit.ly/3yg8Pwo

Topics:

(00:00:00) - Intro
(00:01:00) - Ben’s background and career
(00:03:25) - How unlevered value creation has changed
(00:05:48) - Learning the operating chops
(00:08:33) - Making the transition into entrepreneurship and hospitality
(00:15:02) - The Trailborn strategy
(00:24:13) - Site selection criteria + conversion example
(00:33:29) - Design theory and vertical integration
(00:37:22) - Learning timing and budgets the hard way
(00:39:34) - Keeping a pulse on the business
(00:44:37) - Staffing strategies
(00:48:03) - The power of thoughtfulness
(00:53:40) - Balancing investment returns and building an incredible brand
(00:56:32) - Raising capital
(01:03:00) - Investing in people
(01:12:41) - What is your favorite hotel?