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.
The #1 Mistake Syndicators Make When Raising Capital
Nic McGrue shares his journey into securities and real estate law, explaining how his firm helps investors lawfully raise capital through syndications and funds. The conversation exposes how often investors unknowingly violate securities laws, especially through improper joint ventures, social media solicitation, and unstructured capital raises.
Derek and Nic walk through syndications vs. funds, equity vs. debt structures, Reg D exemptions (506(b) and 506(c)), accreditation rules, and the real risks of second-position capital stacks. Nic also explains why PPMs protect both investors and operators, what legal documents are non-negotiable, typical costs and timelines, and what market cycles mean for future capital raising.
This episode is a must-listen for any investor who plans to raise money now or in the future.
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.
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.
From Flips to Multifamily: Building Stability and Wealth with Jimmy Edwards
In this episode of the Generations of Wealth Podcast, Derek Dombeck sits down with Jimmy Edwards, a Texas-based real estate investor who evolved from loan officer and house flipper to multifamily owner and syndicator. Jimmy shares his full-circle journey—from selling high-rise condos before the 2008 crash to navigating lending shifts, flipping foreclosures, and now managing large-scale multifamily properties in the Dallas–Fort Worth area.
Together, Derek and Jimmy dig into market cycles, lessons learned from past downturns, and how to transition from single-family investing to multifamily ownership with confidence. They break down lending trends, rate expectations, government policy shifts, and the role of AI in real estate operations—all while emphasizing relationships, long-term strategy, and community-focused investing.
From Banker to $700M Multifamily Mogul
In this insightful episode, Derek Dombeck sits down with Sam Morris, Partner at Lone Star Capital, to unpack his remarkable journey from corporate banking to managing over 5,000 multifamily units and nearly $750 million in assets under management. Sam reveals how mastering underwriting, surviving major setbacks, and focusing on operational excellence built the foundation for long-term success. Together, they explore lessons learned from past market cycles, the future of multifamily investing, and the mindset required to thrive in shifting economies.
What Is a Capital Stack? Simple Breakdown for Real Estate Investors
Derek sits down with multifamily syndicator Randy Langenderfer to unpack his journey from corporate exec to full-time investor and coach. Randy shares the hard-won lessons from starting as an LP, moving into GP roles, structuring deals that align incentives, navigating the interest-rate shock, and where the next opportunities will likely appear. If you want specific questions to vet sponsors, a clear take on 70/30 PREF vs 80/20 “simple stack,” and a realistic read on distressed deals ahead, this one’s for you.
From Flipping to Freedom: Paul Moore on Boring Investing, Big Losses & Purpose-Driven Wealth
In this powerful episode of the Generations of Wealth Podcast, Derek Dombeck interviews seasoned investor Paul Moore, who shares his 25+ year journey from corporate life to entrepreneurship, house flipping, and finally, to becoming what he calls a “boring investor” in commercial real estate.
Paul opens up about his early mistakes, chasing shiny objects, losing millions, and the critical mindset shift that led to long-term success. The conversation goes deep into topics like investor due diligence, mobile home parks, financial freedom, and even Paul’s heart-led mission to combat human trafficking.
Can You Really Sell Real Estate Without Paying Taxes?
In this powerful and heartfelt episode of the Generations of Wealth Podcast, host Derek Dombeck sits down with Camille Scott-Wiles, a former ICU nurse who turned financial strategist, author, and educator. Camille shares her deeply personal journey through family tragedy, frontline healthcare, and financial uncertainty—leading her to early retirement at 42 by leveraging precious metals, IULs, and advanced wealth strategies.
Her unique take on life insurance as a wealth-building tool, along with her insights on precious metals, mindset, legacy planning, and financial literacy for kids, makes this episode a must-listen for anyone serious about protecting and growing their wealth.
Can You Build Wealth With Just One Step?
In this powerful episode of the Generations of Wealth Podcast, host Derek Dombeck sits down with Mike Zlotnik, also known as “Big Mike,” to unpack the realities of fund management, real estate market cycles, and investment strategy. From dissecting debt vs. equity funds to analyzing when and why to invest in down markets, this episode delivers both technical insights and philosophical wisdom for investors and fund managers alike.