This episode is a repost of Jake's appearance on the Street Smart Success Podcast, hosted by Roger Becker. You can learn more about Street Smart Success here - https://www.streetsmartsuccess.com/

Jake shares his journey from working in his family's hotel business to building a portfolio of unique, experience-driven hotels. The conversation explores why commoditized limited-service hotels have become riskier assets, and why independent lifestyle hotels are now some of the most defensible real estate investments. Jake also explains DoveHill’s current focus on preferred equity and bespoke equity investments, the operational insights that drive performance, and the long-term value of brand, location, and customer experience in the hospitality sector.

We discuss:

Why limited-service hotels are becoming riskier due to oversupply and commoditization
How Jake evaluates hotel investments through revenue, profit, and guest satisfaction
The value of great operators and how they can distinguish themselves with food and beverage, accounting, and margin control
Why DoveHill is shifting away from new development and instead prioritizing preferred equity and opportunistic repositioning
The importance of humility, persistence, and attention to detail in long-term success

This episode is ideal for anyone investing in or operating within the hospitality space who wants a deeper understanding of today’s market dynamics.

Topics:

(00:00:00) - Intro
(00:01:40) - Jake's journey in the hospitality industry
(00:04:18) - The evolution of hotel investments
(00:05:29) - Challenges and opportunities in boutique hotels
(00:08:53) - Focus on independent lifestyle hotels
(00:15:59) - Preferred equity investments in hospitality
(00:17:34) - Development and operational strategies
(00:21:46) - Vetting partners in hotel investments
(00:27:45) - Key metrics for hotel success
(00:28:32) - Challenges in hotel operations
(00:28:43) - Financial management in hotels
(00:29:28) - Efficiency and profitability
(00:30:22) - Value add strategies in hospitality
(00:34:07) - Third party management in hotels
(00:41:44) - Impact of external factors on hotels
(00:44:51) - AI and innovation in hotel management
(00:46:47) - Lessons learned and personal insights
(00:50:11) - Conclusion and contact information

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