The Hotel Investor Playbook

Welcome to The Hotel Investor Playbook, hosted by real estate investors and hospitality experts Michael Russell and Nathan St Cyr. As the founders of Malama Capital and Howzit Hostels, Michael and Nathan have a wealth of experience in owning and operating boutique hotels, hostels, and other experiential lodging properties. With over $30 million in real estate investments, including short-term rentals, long-term rentals, commercial retail, and hospitality properties, they bring a unique perspective on how to turn passion-driven investments into financial freedom.

In this podcast, they share their roadmap for transitioning from traditional real estate investments to boutique hotels, offering listeners the insights and strategies needed to succeed in this niche market. Whether you're looking to learn about identifying the right property, managing operations, or understanding the financial complexities of boutique hotel ownership, The Hotel Investor Playbook has you covered.

Join Michael and Nathan each week as they document their journey towards building a $400 million real estate-based business and bring you along for the ride. Subscribe now and start turning your real estate investment dreams into reality.

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The Hotel Investor Playbook

Buying Hotels Is Just the Start: How to Build a Lasting Hospitality Brand | Keir Weimer E29

April 29, 2025

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