How to Raise Millions in Real Estate Without Sounding Salesy
In this episode of the Generations of Wealth Podcast, Derek sits down with real estate veteran Adam Gower, who has raised hundreds of millions of dollars throughout a career spanning development, distressed assets, institutional portfolios, and digital capital formation.
Adam shares lessons from decades in real estate — from the savings and loan crisis, to distressed debt sales after 2008, to building digital marketing systems that help sponsors raise capital online.
The conversation dives deep into the psychology of raising money, investor trust, authenticity, and why today’s noisy online environment makes genuine relationships more important than ever.
How to Win in Any Market Using Creative Real Estate
Chris Prefontaine recounts his early career, losing everything in the 2008 crash, and how that experience reshaped the way he approaches real estate and business. Out of that adversity came the 3 Paydays model, a creative strategy that allows investors to generate income upfront, monthly, and long-term—without relying on banks.
Derek and Chris discuss why creative financing is more important now than ever, how uncertainty in the market creates opportunity, and why ethical deal structuring matters. They also touch on the dangers of misinformation in real estate education, the importance of integrity, and how the right mindset separates long-term winners from short-term speculators.
This episode also marks a major milestone—100 episodes of Generations of Wealth—and highlights how relationships, not transactions, are the foundation of lasting success.
The Smarter Way to Be a Landlord: Property Management, Sustainability & Scale
David Holman shares how his real estate journey began after realizing traditional employment wouldn’t provide the lifestyle or financial security he wanted for his growing family. Starting with single-family rentals, David gradually scaled into mixed-use and small commercial properties, learning firsthand the importance of management, tenant relations, and long-term thinking.
A major theme of the conversation is treating tenants as assets, not liabilities. David explains how maintaining properties, investing in energy efficiency, and creating livable spaces leads to better tenants, fewer vacancies, and higher long-term returns.
He also walks through his experience with mixed-use buildings, triple-net leases, and why smaller commercial units can often outperform large single-tenant properties. Derek and David discuss the realities of historic buildings, the risks of deferred maintenance, and why many investors underestimate renovation and compliance costs.
The episode wraps with a deep dive into environmental upgrades insulation, heat pumps, energy efficiency, and grants showing how smart improvements can significantly increase NOI while also improving tenant quality of life.
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.