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.
The Hotel Investor Playbook
He Managed $320M for a Family Office - Then Walked Away to Build His Own Empire | Reilly Brennan E32
After helping scale a family office real estate portfolio from $3 million to over $320 million, Reilly Brennan walked away from the comfort of a W-2 job to carve his own path in boutique hospitality.
In this episode, we sit down with Reilly to unpack how he sourced and acquired two independent hotels in Duluth, Minnesota, one through creative seller financing, the other straight off LoopNet. We break down his underwriting process, deal structure, construction strategy, and how he’s building a brand that reflects his values, not someone else’s investment thesis.
You’ll also hear:
- Why Reilly left the multifamily world for experiential hospitality
- How he underwrote a $700K deal in real time, then moved fast to close it
- His approach to FF&E, design, and building a team from scratch
- What it actually feels like to go all-in on your own vision
- The hidden value of small deals when you’re playing a long game
Whether you’re just getting started or thinking about scaling, this episode is full of honest insight about the hard work and fulfillment that come with betting on yourself.
Connect with Reilly:
Website: https://www.thetrailsidehotel.com
Instagram: https://www.instagram.com/the.brennan.buzz/
LinkedIn: https://www.linkedin.com/in/reilly-brennan-258968172/
Have a deal?
Send it to us: https://www.malama-capital.com/deal-submission
Connect with Mike and Nate:
Invest with Mike & Nate: malama-capital.com/invest
Instagram: @the_hotel_investor_playbook
Contact Us: info@hotelinvestorplaybook.com