The Hotel Investor Playbook
Michael Russell & Nathan St Cyr
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.
Episodes
Mentioned books
Jul 8, 2025 • 1h 11min
$187M Hotel Portfolio by Age 30: How to Choose the Right Deals, Brands, and Ops Model | Sujay Mehta E39
Sujay Mehta, a dynamic hotel entrepreneur who built a $187M hospitality portfolio by 30, shares his journey from neuroscience to real estate. He discusses how to smartly select hotel brands and operational models, drawing on personal triumphs and setbacks. Sujay reveals the secrets to competing with major chains and maximizing hotel value without extensive renovations. He also emphasizes the significance of culture in operations and the pitfalls of third-party management versus self-management. His insights provide a roadmap for budding hotel investors.
11 snips
Jul 1, 2025 • 44min
Turning Passion into Profit in Rural Hospitality | Dave Cook E38
Dave Cook, the founder of Barn Door Hostel in Rumney, New Hampshire, shares his remarkable journey from a volunteer to a successful hostel owner. He reveals how he transformed an old chicken coop into a bustling basecamp for climbers and adventurers using sweat equity. The conversation dives into strategies for attracting guests to a seasonal market and navigating the complex regulations of rural hospitality. Dave candidly discusses the emotional toll of entrepreneurship, the balance between personal values and business growth, and his vision for the future.
5 snips
Jun 24, 2025 • 37min
Bootstrapped Hospitality: Scaling Your Hotel Portfolio Without Major Capital | Austin Phippen E37
Austin Phippen, the dynamic owner of Chama Trails Motel and Turquoise Antler Hospitality, shares his journey of transforming a small roadside motel into a successful brand. He discusses the 'Motel Hack' mindset, emphasizing seller financing and the importance of positive reviews over immediate renovations. Austin explains how bundling properties enabled full staffing and highlights effective rural marketing strategies that drive direct bookings. His insights into navigating challenges in small-town hospitality make this a must-listen for aspiring investors.
Jun 17, 2025 • 1h 1min
Building a Scalable Outdoor Hospitality Brand Through Franchising | Brian Linton E36
Brian Linton, co-founder of Finding Promised Land and a former $20M apparel CEO, discusses his pivot to outdoor hospitality. He reveals how a COVID-era motel purchase blossomed into a booming glamping brand. Linton shares insights on navigating zoning challenges, selecting prime land, and the benefits of owning business outright versus raising capital. His franchise model aims to expand Ferncrest to over 100 locations. Plus, he highlights the power of social media for brand growth, amassing 350K followers while keeping creativity alive in the hospitality sector.
Jun 10, 2025 • 51min
How to Know If Your CPA Is Helping You or Holding You Back | Kelly Tate E35
Kelly Tate is a seasoned CPA and Co-Founder of KTA Financial Services, specializing in tax strategies for real estate investors. In this engaging discussion, she reveals the difference between Section 179 and bonus depreciation, and how cost segregation can elevate your tax savings. Learn the criticality of entity structure in liability protection and tax treatment. Kelly also emphasizes the importance of finding the right CPA and when to seek a second opinion on your tax strategy, ensuring you maximize your financial outcomes.
Jun 3, 2025 • 37min
Why Hostels Are an Untapped Investment Opportunity in the U.S. | Mike & Nate E34
Explore the exciting world of hostel investments and discover why they're an untapped goldmine in the U.S. market. Learn how to transform underperforming assets into thriving destinations with innovative guest experiences. Uncover the secrets of successful marketing strategies that fuel growth, especially targeting Gen Z travelers who crave community. Delve into the financial advantages of rethinking revenue models and why flawed properties can be lucrative. This insight could reshape your view on hospitality investments!
May 27, 2025 • 45min
The Strategic Power of Third-Party Hotel Management | Bryan Fish E33
Bryan Fish, CEO of Reliance Hospitality, shares insights from his extensive experience in hotel management and development. He emphasizes the power of aligning with third-party operators to transition from small-scale to institutional investors. Bryan discusses common pitfalls owners face during acquisitions and sheds light on the complexities of franchise agreements. He also highlights the importance of building a strong team and makes a compelling case for strategic brand alignment in creating a successful hospitality portfolio.
May 20, 2025 • 47min
He Managed $320M for a Family Office - Then Walked Away to Build His Own Empire | Reilly Brennan E32
Reilly Brennan, founder of the Trailside Hotel in Duluth, previously scaled a family office's real estate portfolio from $3M to $320M. He shares his bold transition to boutique hospitality, discussing how he acquired two hotels and the creative seller financing used. Reilly highlights his decision-making strategies in fast-paced deals, the emotional journey of entrepreneurship, and the significance of design in crafting guest experiences. Listeners gain insights into the hidden potential of small deals and the fulfillment that comes from pursuing one's vision.
May 13, 2025 • 48min
Building a $6M Micro Resort with Only 3% Down Using a USDA Loan | Ian Joseph E31
Ian Joseph, founder of Branch, shares insights on leveraging USDA Rural Business Development loans to fund a $6M micro resort in West Virginia with just 3% down. He discusses the often-overlooked financing strategies for boutique hospitality projects and the importance of community partnerships. Ian also explores the design of high-ADR resort cabins, effective marketing techniques for pre-selling stays, and the economics behind luxury micro resorts versus typical short-term rentals. His journey highlights innovative approaches in hospitality development.
May 6, 2025 • 54min
The Ultimate Guide To Financing Your Next Hotel Deal | Suraj Desai E30
Suraj Desai, a hospitality finance expert leading the practice at Black Bear Capital Partners, shares invaluable insights on hotel financing. He dissects crucial funding options, from SBA loans to CMBS lending, and clarifies why some banks are hesitant now. Suraj emphasizes the importance of good collateral and strong sponsorship while navigating complex financing landscapes. Listeners will learn strategic uses of bridge and mezzanine loans, and the differences between predominant SBA loans, making this a must-listen for aspiring hotel investors.
