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.
How to Navigate Lending, Syndications & Industrial Investing in 2025
In this 37-minute episode, Derek Dombeck sits down with David Hansel, founder of Alpha Funding and Lucerne Capital Partners, for a deep dive into the evolution from single-family flips to commercial and industrial real estate investing. David shares his journey through market cycles, how he built a thriving lending business during the 2008 crash, and how he transitioned into managing over $300M+ in assets through funds and syndications.
You’ll gain first-hand insights into hard money lending, fund management, and small-bay industrial investing — with actionable advice for both new and seasoned investors.
How to Convert Hotels into Apartments (Safely & Profitably)
Derek sits down with Ryan Sudek, CEO of Sage Investment Group, to unpack a repeatable system for converting underperforming hotels/motels into studio apartments—filling an affordability gap while targeting strong returns.
They cover market selection, underwriting, construction (sprinklers, sub-panels, kitchens), property management at 100–200 unit scale, and the capital stack behind Sage’s evergreen fund (quarterly distributions, 1031 within the fund, portfolio diversification). Expect practical detail on risk controls (change-of-use permits before closing, value engineering, local code strategy), tenant quality myths (longer average tenancy than market), and why exterior-corridor assets speed construction. The episode closes with goals (10–15 conversions/year, path to 15k units) and how deals actually reach the team (direct-to-seller, lenders, brokers, 60–70 LOIs out at any time).
Syndications vs. Funds (and SEC Traps): Kevin Kim’s Playbook for Raising Capital the Right Way
Derek sits down with securities attorney Kevin Kim (Fortra Law) to demystify raising capital for real-estate deals—covering when to use a syndication vs. a fund, realistic startup costs, 506(b) vs. 506(c) advertising rules, what actually happens when regulators come knocking, and how note offerings compare to LP/GP fund structures. They also hit modern twists like series LLC funds, why most beginners should avoid tokenization, and a pragmatic outlook for late-2025 across SFR, small multifamily, and shaky commercial sectors. If you raise money (or plan to), this is your compliance-and-strategy cheat sheet straight from a former regulator.