In this episode of the Hotel Investor Playbook, we sit down with Keir Weimer, founder of Weekender Hotels, to unpack how he’s building a boutique hospitality brand designed for the long haul. Keir shares how he aligned his business with his personal lifestyle, his on-the-road strategy for sourcing deals, and the frameworks he’s using to scale Weekender into a generational hospitality company.

We dive into why building a recognizable brand creates enterprise value beyond just owning hotel assets, how he structures his investments for long-term holds, and why focusing on guest experience drives lasting financial results. Keir also breaks down his approach to acquisitions, how EOS has helped him step out of day-to-day operations, and how he’s setting up Weekender to inspire over a million guests a year.

Whether you’re an investor, operator, or aspiring hotel owner, you’ll walk away with practical insights on scaling strategically, building brand equity, and creating a hospitality company that stands the test of time.

Connect with Keir:

Email: keir@weekenderhotels.com

Instagram: @weekender_hotels

Website: https://weekenderhotels.com/

LinkedIn: https://www.linkedin.com/company/weekender-hotels

Connect with Mike and Nate:

Instagram: @the_hotel_investor_playbook

Contact Us: info@hotelinvestorplaybook.com

Invest with us: Visit Malama-Capital.com for more information.