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
Sep 16, 2025 • 1h 3min
How to Craft a Hotel People Will Actually Remember | Bashar Wali E49
Bashar Wali, a seasoned hotelier and founder of This Assembly and Practice Hospitality, shares his remarkable insights from over 30 years in the industry. He emphasizes the importance of emotional intelligence and authentic connections over corporate protocols. The discussion includes critical mistakes first-time hotel owners make and the nuances of different hotel deals. Bashar advocates for unique guest experiences and the value of heartfelt service, reshaping the way we think about hospitality.
4 snips
Sep 9, 2025 • 49min
What Makes a Hotel Succeed or Fail? | Naveed Khan E48
In this conversation with Naveed Khan, COO of London Rock Partners, listeners gain insights into transforming struggling hotels into profitable ventures. Naveed emphasizes that success starts with people, not just financials. He explores the pros and cons of branded versus independent hotels, and how technology is revolutionizing hospitality operations. Additionally, he provides tactical advice for novice investors, highlighting the importance of operational efficiency and location in maximizing returns.
10 snips
Sep 2, 2025 • 1h 6min
From CEO of Days Inn to Launching Marriott’s Autograph Collection | Richard Kessler E47
Richard Kessler, a visionary hotelier with over 50 years in hospitality, shares key insights from his remarkable career. He talks about scaling Days Inn and launching Marriott’s Autograph Collection, focusing on finding opportunities during downturns. Kessler emphasizes the importance of reputation, vision, and teamwork in building lasting brands. He also reflects on how simple advice from his mother shaped his approach to success, proving that hard work and perseverance are essential in overcoming challenges in the industry.
12 snips
Aug 26, 2025 • 56min
How To Use Social Media To Raise Capital And Find Deals | Soli Cayetano E46
Soli Cayetano, a real estate investor and boutique hotel owner, shares her inspiring journey from barista to a $13M portfolio. She reveals how she raised $2.5M in just 60 days using Instagram, highlighting the power of storytelling and personal branding. The conversation dives into the booming wellness trend in hospitality and the nuances of transitioning from residential to boutique hotel investments. Soli emphasizes the importance of building trust and relationships while navigating the challenges of the hospitality sector, making bold moves crucial for success.
Aug 19, 2025 • 52min
Intuition, Joint Ventures, and Building Hotels That Last | Brandon Gore E45
Brandon Gore, a designer and builder with a passion for sustainable construction, discusses his innovative approach to developing The Outlier Hotel in Arkansas. He shares how intuition and data guided his land purchase decision and why he opted for a joint venture model instead of traditional syndication. The conversation dives into the luxury lodging market, unique architectural designs, and the importance of aligning projects with personal values. Brandon also highlights the financial advantages of accelerated depreciation and the power of trusting one’s instincts in real estate opportunities.
15 snips
Aug 12, 2025 • 51min
The Marketing Playbook Every Small Hotel Owner Needs | Steph Weber E44
Steph Weber, a branding strategist and founder of The Weber Co., shares her insights on marketing for small hotels. She reveals how to identify your property's unique selling points and leverage limited resources for maximum results. Steph emphasizes the significance of guest experience as a powerful marketing tool and the shift from merely filling rooms to building a memorable brand. With her real-world experience owning a micro-resort, she provides actionable strategies to stand out in a crowded market.
Aug 5, 2025 • 44min
The Beginner's Guide To Building Wealth In Hospitality | Jonathan Mueller E43
Join Jonathan Mueller, a hands-on real estate investor and hospitality entrepreneur, as he shares his journey transforming neglected motels and campgrounds into thriving community spots. He discusses the importance of taking action instead of waiting for the perfect plan, revealing how he raised $300K in just 72 hours for an RV park deal. Learn about the pros and cons of motels versus RV parks, the nuances of seller financing, and how to navigate the challenges in hospitality investment while balancing risk and personal fulfillment.
Jul 29, 2025 • 45min
Hotel Marketing Decoded: What Every Owner Needs to Know | Anthony Chiaravallo E42
In this engaging conversation, Anthony Chiaravallo, founder and CEO of Vallo Media, shares his expertise in performance marketing for the hospitality industry. He reveals strategies for building effective hotel marketing campaigns that drive real bookings, emphasizing the importance of data analysis and customer engagement. Anthony explains how to identify if your hotel is ready for paid ads and discusses budget-friendly tactics for boutique hotels. He also addresses the impact of AI on advertising and how to adapt in this evolving landscape.
Jul 22, 2025 • 52min
Syndication Simplified: The Strategy That Builds Generational Wealth | Desiree Doubrox E41
Desiree Doubrox, a seasoned real estate investor and CEO of HomWork, shares her expertise in syndication, a powerful strategy for raising capital without personal funds. She discusses how to structure deals and gain credibility as a newcomer, while emphasizing partnerships' importance. Desiree highlights the right mindset for fundraising and the value of mentorship programs. She also reflects on overcoming challenges in real estate, turning setbacks into lessons, and emphasizes the essence of community in building generational wealth.
5 snips
Jul 15, 2025 • 54min
A Masterclass In Experiential Hospitality With The Bolt Farm Treehouse Founders | Tori and Seth Bolt E40
Seth and Tori Bolt, co-founders of the luxury Bolt Farm Treehouse retreat in Tennessee, dive into their journey from music to hospitality. They share how their approach to guest experiences fosters emotional connections, resulting in 100% direct bookings. With a focus on love and intentional design, they discuss building a performance-oriented team culture and tackling industry challenges. Learn about their use of AI for streamlined operations and the impact of storytelling in creating memorable stays that transform lives and strengthen relationships.
