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.
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.
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.
From Rentals to 10,000 Units with Lane Kawaoka
In this episode, host Derek Dombeck interviews Lane Kawaoka, a former engineer turned real estate syndicator and the creator of the Wealth Elevator framework. Lane shares his journey from purchasing his first rental property while working a demanding job, to building a massive portfolio of over 10,000 multifamily units. He dives into how he transitioned from single-family investing to large-scale syndications, what to look for in deals, and why understanding your stage in the “wealth elevator” is crucial for long-term financial success.