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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:
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?
View all episodes
By Jake Wurzak
4.9
3535 ratings
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:
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?
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