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.
Stop Wasting Leads! The Secret Follow-Up System That Closes 40% More Deals
In this episode of The Generations of Wealth Podcast, host Derek Dombeck sits down with real estate investor and copywriting strategist Paul de Ocampo to unpack one of the most overlooked but powerful aspects of investing: lead nurturing and strategic follow-up. Paul shares how his transition from wholesaling and Lonnie deals to becoming a copy expert led him to build OmniDrip, a proven system designed to transform stale leads into closed deals through value-based follow-up, powerful copy, and human touchpoints.
From Tactical to Transformational: Real Estate, Conferences & Conversations
In this powerhouse episode, real estate mogul and entrepreneur Ashley Wilson joins Derek Dombeck for a candid, unscripted conversation that dives deep into multifamily real estate, the true value of in-person networking, and her mission to bring transparency and innovation to the conference world. Ashley unpacks her journey from clinical research to managing over $160M in real estate assets, co-founding Apartment Addicts, and launching the platform Conference Connect. The discussion also tackles the current multifamily market, negotiation dynamics, personal accountability, and the future of live events. Whether you’re a new investor, a seasoned operator, or someone passionate about personal growth—this episode hits on all cylinders.