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.

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.

What does it really take to scale from your first hotel acquisition to managing a hospitality portfolio worth tens or even hundreds of millions?

In this episode, Michael and Nate sit down with Suraj Bhakta, CEO of NewGen Advisory, a leading hospitality brokerage with offices across 12 states and transactions in 44. Suraj brings over two decades of commercial real estate experience, having closed $850 million in hotel deals and facilitated nearly $500 million in capital raises. He’s also Chief Legal Counsel at NewGen Worldwide and a former managing partner of his own law firm.

Together, we dive deep into the real-world playbook for growing a hotel investment business - whether you’re acquiring your first property or trying to exit a $15 million deal.

We cover:

– What makes a hotel market worth investing in

– How to raise capital beyond friends and family

– Why the real pros plan their exit before they even buy

– SBA loans vs CMBS vs local banks: financing pros and cons

– The risks and rewards of boutique hotels vs flagged properties

– Why extended-stay hotels are gaining momentum

– How top investors scale and what separates them from the rest

If you’re serious about building wealth through boutique hotels and experiential hospitality, this episode will help you play the game like a pro.

Connect with Suraj:

Email: suraj.bhakta@newgenadv.com
Website: https://newgenadv.com/
Linkedin: Suraj Bhakta
Instagram: @newgenadvisory

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 special Saturday edition, we’re flipping the script. No guest today — just Mike and Nate giving you a behind-the-scenes look at what’s going on inside Malama Capital.

After a listener reached out asking to hear more about our journey, we decided to hit record and share where we’re at, what we’re focused on, and how we’re thinking about the road ahead.

We cover:
Why Q2 is all about acquisitions and our $10M purchase goal

How we’ve restructured our team to create more bandwidth

Using ChatGPT to refine our buy box and narrow in on target markets

Our take on the current investment climate — and why uncertainty might be the window of opportunity

If you’re building your own hospitality investment business (or thinking about it), this is a real-time look at what that actually looks like.

Click here to submit a deal

Click here to get the Time / Energy Audit

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.

What do you do when you get fired from your job and get escorted out with a cardboard box? If you’re Sky McLean, you build one of the fastest-growing hospitality brands in Canada.

In this episode, we sit down with Sky McLean, founder and CEO of Basecamp Resorts, owner of 14+ resorts, and operator of over half a billion in real estate. From bootstrapping her first hotel with a BMW loan to raising $40 million through Instagram, Sky’s story is a masterclass in grit, creativity, and bold vision.

We dig into how she scaled her adventure-focused hospitality brand, her unique capital raising strategy, why she avoids big-name hotel flags, and how she balances leading 500+ employees with being a full-time mom and mountain sports junkie.

Whether you’re just getting started or looking to scale your hotel portfolio, this episode is packed with insight, inspiration, and practical wisdom from someone who’s actually done it.

Connect with Sky:

Instagram: @skymclean

Linkedin: https://www.linkedin.com/in/sky-mclean-2299a420/

Website: https://invest.basecampresorts.com/

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.

What if you could double your money in one season with glamping tents? Zac Willms is pulling it off — and building a profitable outdoor brand in the process.

In this episode, Mike and Nate talk with Zac Willms, co-owner of a thriving glamping resort in Tobermory, Ontario. Zac shares how he turned a neglected trailer park into a profitable outdoor hospitality destination, the simple formula behind his success, and why buying an old campground might be the real cheat code.

We unpack everything from startup costs, seasonal cash flow, and staffing — to marketing strategy, zoning hacks, and influencer partnerships that built a 70% direct booking rate.

If you’re looking to create high-margin hospitality experiences without the complexity of hotel development, this one’s for you.

Connect with Zac:

Linkedin: Zac Willms

Website: Grotto Getaway

Instagram: @zacwillms

Facebook: Zac Willms

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.