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.
The Psychology of Wealth: Avoiding the Mistakes That Destroy Fortunes
In this episode of the Generations of Wealth Podcast, Derek sits down with wealth advisor Jonathan Blau, a seasoned financial planner with decades of experience helping affluent families grow and preserve wealth.
Rather than focusing on picking investments, Jonathan explains why behavior — not intelligence — is the biggest driver of financial success or failure. The conversation dives into behavioral finance, investor psychology, inflation risk, volatility myths, generational wealth, and why many investors sabotage themselves without realizing it.
Jonathan challenges traditional industry thinking, offering a fresh perspective on risk, forecasting, emotional decision-making, and long-term investing.
This episode is less about tactics — and more about mastering the mindset required to build lasting 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.
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.
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.