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.
From Mortgage Broker to Fund Manager: Real Estate Lessons That Matter
In this episode of the Generations of Wealth Podcast, Derek sits down with investor and lender Will Harvey to discuss hard money lending, private funds, underwriting risk, and the importance of staying humble in changing market cycles.
Will shares his journey from mortgage lending into flipping houses, apartment syndications, and eventually launching his own lending fund. Together, Derek and Will break down the realities of leverage, underwriting, investor protection, and why many people underestimate risk during strong markets.
This episode is packed with practical insight for anyone interested in private lending, raising capital, or building long-term wealth through real estate.
The AI Sales Combination Nobody’s Talking About
In this episode of the Generations of Wealth Podcast, Derek sits down with global entrepreneur Alaric Ong from Singapore, who scaled a business from $0 to $1.2 million in just 18 months.
Alaric shares his expertise in high-ticket sales, Facebook marketing, and AI-driven automation, breaking down how entrepreneurs can generate leads, convert sales, and scale their businesses using systems and leverage.
This episode bridges the gap between real estate investing, marketing, and modern AI tools, showing how the same principles apply across industries.
Capital Gains Tax: The Loophole Nobody’s Talking About
If you’re a real estate investor facing large capital gains taxes, this episode could change how you think about selling property.
In this episode of the Generations of Wealth Podcast, host Derek Dombeck sits down with alternative investment specialist Jon Lontai to break down advanced strategies that investors use to defer taxes and create passive income — including 1031 Delaware Statutory Trusts (DSTs), Opportunity Zones, and other alternative investments.
Many investors know about the traditional 1031 exchange, but very few understand how DST investments can provide a passive solution while still deferring capital gains taxes.
Jon explains how DSTs work, who they’re best suited for, and why they’ve become increasingly popular among investors looking to transition away from active property management while still maintaining exposure to real estate.
If you’re thinking about selling investment property, reducing landlord responsibilities, or protecting long-term wealth, this conversation will help you understand the options available to you.
The Note Investing Blueprint Traditional Flippers Miss
Jay Redding has been investing in real estate since 2004, completing over 100 flips and building a rental portfolio before eventually shifting his focus toward note investing. As margins tightened in the fix-and-flip market and operational headaches increased, Jay and his son-in-law Kyle began exploring the note space more deeply.
They discovered that by helping investors structure seller-financed deals correctly, those investors could later sell part of the note and quickly recover capital to fund additional deals. Instead of holding a property long-term, investors could create a performing loan and sell a portion of the payment stream to a note buyer.
Jay explains how partial note purchases work, what note buyers look for, how to properly structure a note, and why interest rates, down payments, and servicing all play a critical role in the resale value of a note.
The discussion also highlights why many investors unknowingly create “bad notes” that force them to take deep discounts when selling. By structuring notes correctly from the beginning, investors can recover capital faster while still earning long-term income.
The episode closes with insights on the changing real estate market, shrinking flip margins, and why notes may be one of the best ways to generate long-term generational wealth.
Think Like an Investor: Market Cycles, Smart Deals & Building Real Wealth
What separates investors who survive from those who thrive? It’s not just deals it’s how they think.
In this powerful conversation, Derek Dombeck sits down with veteran investor and former Wall Street trader Joel Kraut to unpack decades of experience navigating market crashes, rebuilding wealth, and mastering the psychology of investing.
Joel shares lessons from losing millions during the housing collapse, why relationship capital matters more than ever, and how today’s investors can position themselves to win in shifting markets. From creative deal structuring to partnership strategy and leveraging technology, this episode delivers real-world wisdom that applies whether you’re new to investing or scaling a serious portfolio.
If you want to build a life you love not just survive this episode is a must-watch.
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.
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.