Scale Faster with Direct Bookings and Group Stays with Tim Ensmann

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.

In this episode, you'll learn:
Why Tim shifted from short-term rentals to boutique hotels
How direct bookings increase profit and reduce OTA dependence
The marketing strategy that filled hotel bookings before opening
Why group bookings create more predictable revenue
How to use social media to grow a hospitality brand
The biggest renovation mistakes to avoid
Why investor expectations matter during hotel development
How to decide whether boutique hotels fit your investment goals

Connect with Tim Ensmann
LinkedIn: https://www.linkedin.com/in/tim-ensmann/
Website: https://boutiquehotelfund.com/
Zeke Freeman's new book, Radical Hospitality, is coming this September.
The book explores how to build cool stuff, serve a lot of people, and create lasting wealth, and how hospitality can be the vehicle for all three.
Join the waitlist: https://radicalhospitality.life/join
Grab the free Radical Hospitality Starter Kit → root-ad.com/starter

Connect with Zeke Freeman:
Instagram: @zekefreeman_rootarchitecture and @rootarchitecture
YouTube: @rootarchitecture
Facebook: @RootArchitectureandDevelopment
LinkedIn: Zeke Freeman
X/Twitter: @zfreemanroot

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