Are You Making This Big Real Estate Mistake?
Shawn Moore recounts his journey from making big money early in real estate, to losing everything in 2009 when the high-end resort development he worked on collapsed after a federal indictment. That moment forced him to rebuild with humility — starting from selling houses, working with investors, then re-entering development and eventually finding long-term success in short-term rentals.
Shawn opens up about infertility struggles, the emotional toll it took, and how becoming a father changed his definition of “legacy.” The episode also digs into the reality of the STR market: why the COVID boom misled new investors, how supply/demand has shifted, why most properties underperform, and why the future belongs to investors who understand hospitality, experience, and proper underwriting.
The conversation ends with deep insights on creative finance, rebuilding after hardship, and living a life built on purpose, resilience, and responsibility.