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