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.
Note Investing Made Simple: Becoming the Bank
Fred Moskowitz shares how the volatility of the tech industry led him to seek alternative income streams and ultimately discover mortgage note investing. Instead of owning properties and dealing with tenants, Fred focuses on owning the debt—collecting payments as the lender rather than the borrower.
Together, Derek and Fred walk through the fundamentals of note investing, including buying performing notes, using partials to deploy smaller amounts of capital, understanding foreclosure timelines, evaluating borrower risk, and navigating state-specific laws. They also discuss taxation realities and why self-directed IRAs and Roth IRAs can be powerful vehicles for note investors.
This episode demystifies note investing and shows how it can fit into both active and passive investment strategies.
Why Smart Investors Are Using IRAs for Real Estate with Henry Yoshida
Henry Yoshida shares his journey from Merrill Lynch and traditional financial services into building Rocket Dollar, a platform designed to make alternative investing inside retirement accounts as easy as buying stocks in a brokerage account. After years in finance, Henry realized that even industry professionals didn’t understand self-directed IRAs—and those who did were often frustrated by slow, unhelpful custodians.
The discussion covers how Rocket Dollar structures IRAs using IRA-owned entities that allow investors to control their own bank accounts, drastically improving transaction speed and flexibility while maintaining compliance. Derek and Henry also dig into the dangers of prohibited transactions, why many custodians overstep their role, and why velocity of capital matters when closing real estate deals.
The episode expands into broader macro insights—why most retirement money is trapped in stocks and mutual funds, why diversification is broken, how required minimum distributions drive government policy, and why Henry believes private investments will overtake public investments within the next decade.
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.
Never Too Late to Start: Jens Nielsen’s Journey to Freedom Through Real Estate
This episode features Jens Nielsen—a Danish immigrant who didn’t begin his entrepreneurial journey until his mid-40s and has since built ownership stakes in 2,500+ multifamily and industrial units across the U.S. Jens reveals the mindset shifts required to leave a W-2 career, overcome limiting beliefs, and pursue real estate and business freedom with clarity and intention.
He and Derek take listeners through market realities, the challenges facing today’s multifamily operators, and why mindset—not mechanics—is the real separator between those who dream and those who act. They also dive into coaching, personal vision, and building a business that aligns with the life you want.
Mastering Passive Wealth: How to Invest Like Institutions with Pascal Wagner
Derek and Pascal explore the world of passive investing, due diligence, long-term wealth strategy, and how everyday investors can model the same approach that major institutions use. Pascal explains how he vetted deals across 23+ investments, the role of understanding inevitabilities, and how his unique experience in venture capital shaped his investment philosophy. They also dive into macro trends affecting real estate, from industrial growth and medical facilities to low-income housing and why Airbnb might be a dangerous play.
How to Turn a W-2 Into 100 Doors: From Nursing to Multifamily & Assisted Living
Savannah Arroyo shares how she parlayed a nursing career into a scalable real-estate portfolio by tapping home equity, moving quickly from single-family to multifamily, and raising capital through relationship-driven 506(b) syndications. She walks through underwriting in uncertain markets, investor communications, deal structures (including no-pref splits), and why she’s expanding into assisted living where her healthcare operations background is a unique advantage.
The Storage Strategy Every Investor Should Know
Derek and guest Jacob Vanderslice dive deep into the mindset and mechanics behind building a durable real-estate business — specifically self-storage. Jacob shares how he went from fighting fires to building a multi-state storage empire by surviving market cycles, raising capital responsibly, and developing systems that scale.
They discuss the current market environment, rising rates, cracks in the economy, deal flow challenges, overpriced assets, and investor fear. Jacob explains why transparency and delivering bad news quickly is critical when managing investor capital, and why operational excellence matters more now than ever.
The conversation also covers sourcing off-market deals, building long-term investor trust, managing a large operations team, navigating overhead, and avoiding the pitfalls that wipe out rookies. The episode ends with timeless advice: take action, take smart risks, and don’t wait for the perfect deal.
How Derek Vickers Built a $20M Mobile Home Park Empire
In this episode of the Generations of Wealth Podcast, host Derek Dombeck sits down with fellow real estate powerhouse Derek Vickers, the founder of Victory Capital.
Vickers went from door-to-door insurance salesman making $13K a year to owning 44 mobile home parks and over 2,100 lots across the Sunbelt — all in just a few years.
They unpack the truth about persistence, negotiation, and scaling, while revealing how mindset and accountability can completely change your financial trajectory. Whether you’re a beginner or seasoned investor, this conversation offers a masterclass in building wealth through discipline, people skills, and problem solving.