Building the Boutique for the Outdoors - Ben Weinberg

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Masters of Moments

Jake Wurzak

126 episodes

2 weeks ago

Masters of Moments involves conversations with top entrepreneurs and business leaders about hospitality, Real Estate investing, and company building. We explore the ideas, strategies, and approaches that brought them to where they are today. This podcast is for you if you are a seasoned investor, an upstart entrepreneur, or someone looking to break into the real estate and hospitality investing world. Jake Wurzak is the CEO of DoveHill Capital Management and Wurzak Hotel Group, a leading vertically integrated hospitality investment platform. Since 2011, he’s led the investment of $1.5 billion in hotel assets throughout the country. Follow Jake on Twitter: https://twitter.com/JWurzak Take the Hospitality Real Estate Investing Masterclass: https://learn.jakewurzak.com/ Subscribe to the show on YouTube: https://www.youtube.com/channel/UCzvzdJASDiEXhV9VhkaEoWA Learn How to Invest with DoveHill: https://dovehillcos.junipersquare.com/portal/view_lead_capture_form/MzhmOGE4MTUwMjZhNDZkNmU1MGE0NmYwOTdhZjk2MzAxYzE0MjIzMGdBV1ZEUUFBQUFBQUFBQW9UVzhJVFdzTlRrNkpkSlF1 DoveHill: www.dovehillcos.com

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

Masters of Moments

1 hour 14 minutes

1 month ago

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?