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Index/Startups & Founders/Radical Hospitality Show
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Scale Faster with Direct Bookings and Group Stays with Tim Ensmann

Radical Hospitality Show · 2026-07-29 · 53 min

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Topics in this episode

Real estate investingDirect bookingsboutique hotelsgroup stayshotel investing

Episode notes

In this episode, host Zeke Freeman sits down with Tim Ensmann, founder of the Boutique Hotel Fund and managing partner of the Pine Tree Hotel. Tim shares how he went from investing in short-term rentals to building a fast-growing boutique hotel business. Many investors start with short-term rentals, but Tim Ensmann believes boutique hotels create a better path to long-term wealth. In this conversation, he shares how his team transformed an underperforming hotel into a profitable business using strong branding, direct bookings, social media marketing, and group experiences. He also talks about the mistakes they made during renovations, why marketing should start before opening day, and how they are applying those lessons to build an even bigger boutique hotel portfolio.

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