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
Dec 9, 2025 • 42min
The 3 Distress Signals That Make the Next 12 Months a Buyer’s Market | Suraj Bhakta E61
Suraj Bhakta, CEO of NewGen Advisory, is a seasoned commercial real estate attorney with a wealth of hotel brokerage experience. He discusses the current market crisis, highlighting how the SBA shutdown is affecting transactions and creating a backlog. Suraj reveals crucial signs of distress that buyers should watch for, such as deferred maintenance and maturing loans. He emphasizes the importance of diligent underwriting, practical buyer strategies, and taking advantage of the upcoming buyer's market while cautioning against seller pricing mistakes. His advice? Build a focused team and be ready to act!
10 snips
Dec 2, 2025 • 59min
7 AI Tools To Help You Buy and Operate Hotels (With No Staff and No Time) | Jake Heller E60
Join Jake Heller, founder of the AI for CRE Collective, as he unveils groundbreaking AI tools tailored for boutique hotel investors. Discover how to swiftly research new markets and streamline processes with innovative tech. Jake shares insights on automating administrative tasks, generating professional investor decks, and reducing legal costs through AI-assisted reviews. Expect to learn practical tips on using AI for effective underwriting and asset management, all aimed at giving small operators a competitive edge without increasing staff.
7 snips
Nov 25, 2025 • 41min
The Private Island Resort Built With Sweat, Not Millions | Odis Martin E59
Odis Martin, owner and captain of the Garifuna family-owned eco-lodge Sindiri on the Reef in Belize, shares his inspiring journey from a graduate thesis to a stunning island resort. He recounts the challenges of hand-digging a swampy island, navigating logistics, and rebuilding after hurricanes. Odis explains why Belize is an attractive option for U.S. investors and details the gritty reality of self-funding without outside investors. His story reveals the passion, resilience, and creativity required to turn a dream into a thriving business.
13 snips
Nov 18, 2025 • 47min
How to Get Brokers to Send You Deals | Hunter Johnson E58
Hunter Johnson, President of Investment Sales at US Hotel Advisors, shares insights on the hotel investment landscape. He discusses how today’s market gives buyers leverage and reveals what lenders prioritize for first-time buyers. Johnson explains the workings of SBA loans and how to creatively structure deals when numbers are tight. He emphasizes the importance of building relationships with brokers to uncover off-market opportunities and advises investors to focus on markets they know for successful transactions.
14 snips
Nov 11, 2025 • 47min
The Husband and Wife Duo that Scaled from 5 Airbnbs to 2 Boutique Hotels (Without Burning Out) | E57
Mitch Ehly and Katie Wanzer, the husband-and-wife team behind Fresh Coast Motel and Spruce & Shore Motel, share their journey of transforming historic motels in Door County into stylish boutiques. They discuss key strategies that helped them scale from Airbnbs to full hotel operations while keeping their relationship intact. Discover their innovative use of technology for guest experiences, the challenges of balancing design with functionality, and how they handled the intricacies of partnership dynamics and staffing in a hospitality-focused business.
21 snips
Nov 4, 2025 • 44min
Hotel Technology You Can Install To Boost NOI | Sue Graves E56
Sue Graves, founder and CEO of Experience Alive, brings over 30 years of hospitality expertise to the table. In this engaging discussion, she reveals how technology can significantly boost hotel profitability. From using conversational AI to decrease front desk calls to implementing delivery robots that enhance service speed, Sue highlights practical tech solutions. She also discusses the impact of RFID tracking on linen costs and smart room technologies that promote sustainability and energy efficiency, making innovation accessible for every hotel owner.
22 snips
Oct 28, 2025 • 50min
How to Replace a Six-Figure Job with Boutique Hotel Investing | Tim Ensmann E55
Tim Ensmann, founder of Boutique Hotel Fund, left a lucrative tech sales career to build a multi-million-dollar portfolio of boutique hotels. He shares pivotal moments that led to his transition and how he used short-term rentals as a stepping stone. Tim reveals valuable insights on identifying the right first project, the financial markers to consider before quitting, and the unexpected success from group bookings that skyrocketed revenue. He also emphasizes the importance of education, strategic partnerships, and hands-on involvement in the renovation process.
13 snips
Oct 21, 2025 • 24min
Real Estate Syndications 101: How Investors and Operators Actually Get Paid | Michael Russell E54
Discover the inner workings of real estate syndications, where investors and operators navigate fees, profit splits, and structures. Michael Russell explains the crucial roles of LPs and GPs, offering insights into preferred returns and the mechanics of financial waterfalls. He emphasizes the importance of simplicity in deals to attract repeat investors. Plus, learn about overlooked syndication risks and practical tools to enhance modeling and operations. This is your go-to guide for mastering hotel investments!
9 snips
Oct 14, 2025 • 55min
What It Really Takes to Buy Your First Hotel in 90 Days | Jacobo Hernandez E53
Jacobo Hernandez, founder and CEO of FreedomVest Capital, shares his bold journey of trading a $10M short-term rental portfolio for a 90-day road trip to acquire a boutique hotel. He discusses uncovering a hidden gem in Eureka Springs for just $1.2M, driven by hands-on market visits and data analysis. Jacobo outlines his unique approach to storytelling for fundraising, which raised over $2.5M. His focus on creating wellness-focused experiences highlights the importance of innovative asset strategies in the hospitality industry.
14 snips
Oct 7, 2025 • 59min
Building a Lifestyle Hotel Brand in Costa Rica | Bill Graf E52
Bill Graf, former investment banker turned founder and CEO of ONDA, shares his inspiring journey of trading Wall Street for a boutique hotel brand in Costa Rica. He discusses uncovering hidden opportunities in small hotels and the unique challenges of buying real estate abroad. Bill offers insights on keeping properties full year-round through innovative strategies and the advantages of investing in Latin America. His vision for ONDA blends the social energy of hostels with boutique comforts, making it a game-changer in the hospitality sector.
