Episode 40

Tim Ensmann: The business case for doing hotels differently

What makes a boutique hotel a compelling experience and a strong business? Tim Ensmann, Founder and Managing Partner of Boutique Hotel Fund, joins The Turndown to explain the thinking behind The PineTree Hotel’s transformation, from investing in shared experiences to building direct demand and predictable group revenue. He shares the decisions behind its reported 98% direct bookings, the challenges of financing an independent hotel, and how he’s taking the model into new properties.

 

About the guest

Tim Ensmann

Tim Ensmann

Hotelier, Investor, Founder & Managing Partner of Boutique Hotel Fund

 

Tim Ensmann is the founder and managing partner of Boutique Hotel Fund and co-founder of Second Home Stays, a vacation-rental management company. Known as “The Boutique Hotel Guy,” he began investing in real estate in 2018 and built a portfolio of short-term rentals before expanding into boutique hotels. His approach combines distinctive design, wellness amenities and group experiences with direct-booking and social media strategies. His projects include The PineTree Hotel in Idyllwild, California, and boutique hotel developments in Blue Ridge, Georgia.

AI-generated transcript

Sebastien Leitner



In 2023, a hotel in the mountains above Palm Springs was doing about $100,000 a year. The owners cleaned the rooms themselves. They’d fill in the pool, not to renovate it, but to stop paying the water bill. They were collecting rainwater in it.



Today, that same property does eight times that revenue. This year, it’s on pace for 10. And 98% of those bookings come direct. No OTA, no flag, no loyalty program.



Just a sauna that went viral, a pickleball court somebody had to fight the budget for, and a very deliberate bet that people don’t remember your bathroom tiles. They remember who they were with. My guest today is Tim Ensmann. He and his partners went from 20 short term rentals to buying the Pine Tree Hotel in Idlewild, California, and turning it into a destination.



And they’re about to run the entire playbook again