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.
What Is a Capital Stack? Simple Breakdown for Real Estate Investors
Derek sits down with multifamily syndicator Randy Langenderfer to unpack his journey from corporate exec to full-time investor and coach. Randy shares the hard-won lessons from starting as an LP, moving into GP roles, structuring deals that align incentives, navigating the interest-rate shock, and where the next opportunities will likely appear. If you want specific questions to vet sponsors, a clear take on 70/30 PREF vs 80/20 “simple stack,” and a realistic read on distressed deals ahead, this one’s for you.
Master Passive Income w/ Dustin Heiner
Derek sits down with investor and podcaster Dustin Heiner to unpack how he went from a government IT job to becoming “successfully unemployed.” Dustin shares the layoff story that sparked his pivot, why he invests strictly for monthly cash flow (not appreciation), and his “build the business first, then buy inventory” framework. They dive into systems, out-of-state teams, market cycles (including the short-term rental glut), and creative deals—plus Derek’s zero-interest win and a live subject-to opportunity that emerged from a tenant call.
How I Made $50,000 With No Money Or Credit!
In this episode of the Generations of Wealth podcast, Derek Dombeck sits down with veteran real estate investor Tony Youngs, who shares the story of how he got started in real estate in the 1980s — from buying his first foreclosure with no money or credit to building a career around uncovering “hidden market” deals. Tony emphasizes the power of direct communication, creative deal structuring, and going the extra mile to solve seller problems — even when that means driving a U-Haul across state lines.
Whether you’re a new investor or a seasoned pro, this episode is packed with practical wisdom on how to find deals others miss — and why the human element in real estate is still the most powerful tool.
Raising Private Money Without Banks
In this episode, Derek sits down with Jay Conner to unpack the art of raising private money for real estate without using banks or institutional lenders. Jay shares his journey from depending on traditional financing to mastering private money strategies since 2009. Together, they walk listeners through mindset shifts, finding and educating lenders, and even turning dead leads into funding opportunities.
What Happens to Your Home Loan When You Move Out?
In this Podcast Episode 66, Derek Dombeck interviews mortgage expert Kevin Guttman. They explore Kevin’s journey from real estate upbringing to ministry work, and eventually into the mortgage industry. The core of the discussion centers around reverse mortgages—how they work, who they’re for, and why they can be an overlooked but powerful financial tool. The two also dive into market trends, economic outlooks, and how investors can creatively use reverse mortgages to fund deals and generate wealth.