The Hotel Investor Playbook
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.
The Hotel Investor Playbook
From CEO of Days Inn to Launching Marriott’s Autograph Collection | Richard Kessler E47
Few people have left a mark on hospitality like Richard Kessler.
He started his hospitality career by helping scale Days Inn into a household name as the early CEO
Then he founded the Kessler Collection, one of the leading boutique hotel portfolios in the U.S., which ultimately helped launch Marriott’s Autograph Collection.
In this episode, Richard shares the biggest lessons from his 50-year career, including:
• How to lead through downturns and find opportunity in distress
• Why reputation as an operator attracts financing and partners
• The role of vision, teamwork, and conviction in building lasting brands
• Why his mother’s advice, “Don’t take the elevator, take the stairs”, shaped his approach to success
This is a rare chance to learn directly from one of hospitality’s true icons.
About Richard
Richard C. Kessler is a visionary hotelier and entrepreneur with more than 50 years of experience in hospitality, best known as Chairman and CEO of The Kessler Collection. He previously served as President and Chairman of Days Inns of America and later pioneered the boutique luxury movement, restoring historic properties like Casa Monica Resort, The Mansion on Forsyth Park, and Savannah’s Plant Riverside District. Kessler co-launched Marriott’s Autograph Collection, becoming its largest U.S. franchise operator, and remains deeply involved in the design and development of each property. Beyond hospitality, he is a committed philanthropist, supporting faith-based initiatives, education, and the arts through scholarships, cultural collections, and community projects.
Connect with Richard
LinkedIn: Richard Kessler - Chairman and CEO at The Kessler Collection | LinkedIn
Website: The Kessler Collection
Connect with Mike and Nate:
Invest with Mike & Nate: malama-capital.com/invest
Submit a deal: https://www.malama-capital.com/deal-submission
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Contact Us: info@hotelinvestorplaybook.com