The Hotel Investor Playbook
Michael Russell
Welcome to The Hotel Investor Playbook, hosted by real estate investor and hospitality operator Michael Russell. Michael is the co-founder of Malama Capital and Howzit Hostels, and has built a personal real estate portfolio exceeding $20 million.With an operator-first mindset, Michael brings a practical perspective to hotel investing. On the show, he breaks down what it actually takes to scale from short-term rentals into boutique hotels, covering deal sourcing, operations, capital strategy, and risk.Each week, Michael shares real lessons from the field as he builds toward a $400 million real estate business, giving listeners an honest look at the decisions, challenges, and strategies behind the growth. Subscribe and follow along as he documents the journey in real time.
Episodes
Mentioned books
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.
16 snips
Sep 30, 2025 • 57min
The “Hotel Guru” on Where to Invest Next & How to Fund Deals | Bob Rauch E51
In this discussion, Bob Rauch, known as 'The Hotel Guru,' shares insights from his 45+ years in the hospitality industry. He reveals how to identify hot markets and avoid profit-eating locations. Bob emphasizes the role of AI and robots in hotel operations, boosting productivity rather than immediate cost savings. He shares essential skills for aspiring investors and forecasts market stabilization by 2026. His experiences range from scaling a 20-hotel management company to his innovative strategies at Brick Hospitality, shaping the future of hotel investments.
13 snips
Sep 23, 2025 • 47min
Why 2026 Looks Rocky for U.S. Hotels And Where Smart Investors Can Hit Big | Jan Freitag E50
Jan Freitag, the National Director of Hospitality Analytics at CoStar Group, offers keen insights into the hotel industry's future. He discusses why the market shifted to stagnation and the risks of rising expenses outpacing revenue growth. Jan highlights the luxury segment's resilience and how local market nuances impact recovery. He emphasizes the importance of data analytics in identifying investment opportunities and shares strategies for succeeding in the sub-$10M market amidst a challenging landscape.
18 snips
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.
14 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.
29 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.
