The Hotel Investor Playbook

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.

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!

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.

We’ve all dreamt of quitting our bland corporate jobs to buy a hotel in Costa Rica… well, today’s guest did that.After leaving a private equity career in San Francisco, Bill Graf traded suits for surf towns and founded Onda, a hospitality brand in Costa Rica that blends the style of a boutique hotel with the social energy of a hostel.You’ll learn:How to uncover hidden opportunities in small hotels that big players ignoreWhat U.S. investors should know about buying real estate in Costa RicaHis unique strategy for keeping his properties full year-roundThis episode is a blueprint for spotting opportunities where others see risk… and will certainly have you daydreaming by the end of it!Follow along with The Hotel Investor Playbook to discover how to invest in hospitality assets the right way.About BillWilliam “Bill” Graf is the founder and CEO of ONDA, a hospitality collective in Costa Rica that blends boutique hotel comforts with the social energy of a hostel. A former investment banker and private equity professional, Bill left Wall Street in 2016 to travel the world, visiting over 50 countries and experiencing firsthand the challenges of inconsistent accommodations. Inspired to create a better model, he launched ONDA to deliver reliable, community-driven stays in lifestyle destinations where major hotel brands won’t go. Today, Bill is building ONDA into a global hospitality brand focused on culture, connection, and transformational guest experiences.Connect with BillWebsite: www.stayonda.comLinkedIn: linkedin.com/in/williamgrafInstagram: @billygoat_graf and  @findyourondaConnect with Michael: Invest with Malama Capital: malama-capital.com/investSubmit a deal: https://www.malama-capital.com/deal-submissionInstagram: @the_hotel_investor_playbookContact Us: info@hotelinvestorplaybook.com

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.

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.

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.

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.

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.

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.