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/

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.

In this episode, we sit down with Ian Joseph, founder of Branch, a luxury micro resort in the hills of West Virginia, to talk about building boutique hospitality with a soul.

Ian’s not only creating a set of luxury cabins, he’s crafting a guest experience rooted in community, design, and nature. And he's doing it all with a lean team, a USDA loan, and a strategic eye for scale.

What You'll Learn:

• Why Ian pivoted from short-term rentals to commercial micro resorts
• How he found and secured the perfect property for $600K
• The exact financing structure, including a rare 97% LTV USDA rural development loan
• His 3-unit design strategy and pricing model for $400+ ADRs
• How Branch partners with the local economy instead of building on-site restaurants and spas
• The marketing game plan used to pre-sell resort stays through crowdfunding
• How to find hidden gem towns perfect for experiential hospitality

Connect with Ian:

Email: ian@staywithbranch.com

Website: https://staywithbranch.com

Instagram: @staywithbranch

Facebook: Staywithbranch

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.

In this episode of the Hotel Investor Playbook, we sit down with Suraj Desai, a hospitality finance expert who has helped close hundreds of hotel deals, to unpack everything you need to know about financing your next acquisition, renovation, or ground-up development.

Suraj breaks down the full capital stack, from SBA 7a and 504 loans to bridge, CMBS, and mezzanine debt. He explains which types of financing work best for boutique hotels vs. flagged assets, why banks are pulling back, and what it really takes to get a deal funded in 2025.

We also cover:

• The difference between good collateral and great sponsorship (and why you need both in today’s market)
• How to use bridge and mezzanine loans to scale faster, even with limited equity
• The truth about SBA loans: how they work, who they’re for, and the major difference between 7a and 504
• What CMBS lenders really look for (and why they’re not always the bad guys)

If you’re serious about buying your next hotel or just want to understand what lenders are looking for right now, this episode is a must-listen. It’s a masterclass in real-world hotel financing.

Connect with Suraj:

Website: https://bbcp-llc.com/

Email: sdesai@bbcp-llc.com

Phone: 773-314-7659

Linkedin: https://www.linkedin.com/in/suraj-desai-4276ba24

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.