Why You Should Never Buy Real Estate Abroad Without Knowing This?
In this episode of the Generations of Wealth Podcast, Derek talks with Ladislas Maurice, founder of The Wandering Investor, about building a decade-long career investing in real estate across emerging markets — and how buying property overseas can also get you a second residency or even citizenship for your entire family.
Why Your Real Estate Strategy Is Failing (It’s Not The Math)
In this episode of the Generations of Wealth Podcast, Derek talks with Denis Shapiro, founder of SIH Capital Group, about the hard lessons he learned moving from single-family landlord to limited partner to full-time syndicator — and why he believes charismatic marketing, crowdfunding platforms, and even AI will never replace the relationship-driven side of real estate.
How to Legally Pay Only 2% Tax
In this episode of the Generations of Wealth Podcast, Derek talks with Mike Milligan, CFP and founder of One Oak Financial, about why most people don’t actually have a financial plan — they have a pile of products disguised as one. Mike also opens up about relocating to Puerto Rico for a legal tax structure that’s dropped his effective tax rate to around 2% on exported business income.
Why Your Kids Might Inherit a Mortgage, Not a Home
In this episode of the Generations of Wealth Podcast, Derek talks with David Bacon, Head of Marketing at WellStreet Financial, about a very different way to invest in real estate: housing bonds. David breaks down how everyday investors — accredited or not — can put as little as $10 into a diversified, real-estate-backed portfolio earning 9-10% annually, without ever becoming a landlord.
“We Own Nothing”: The Conversation That Built a Real Estate Empire
Anton left a $250K corporate job after his girlfriend pointed out they “owned nothing,” pushing him into a real estate mastermind and, soon after, wholesaling. His first deal took six months of cold calling and a last-minute $20,000 renegotiation to net just $7,500 — but it taught him negotiation, underwriting, and persistence. A later flip his wife talked him into netted $94,000 and got 1031-exchanged into more properties, snowballing into 16 rental properties today, managed remotely by his wife while Anton splits time between Miami and Medellín, Colombia. Frustrated by how slow lead generation was, Anton built a team of 150 overseas cold callers and turned it into REI Lead Pros, a company that now sources off-market deals for investors while staying carefully compliant with TCPA/do-not-call regulations. The conversation also covers his podcast, Still Building, which focuses on the unfiltered struggles behind entrepreneurship, and closes on Anton’s own current struggle: whether to pursue his dream of building wellness hotels despite warnings from people already in that business.
Don’t Lose Your Principal: 3 Mistakes Killing Real Estate Deals
Paul Shannon joins Derek Dombeck to discuss his journey from medical device sales into full-time real estate investing and multifamily operations.
Paul shares how he built his investor network, raised capital outside of the traditional friends-and-family approach, and developed his philosophy around protecting investors’ capital. The conversation dives into investor trust, communication, risk management, market cycles, institutional capital, floating-rate debt, and why every real estate deal needs multiple exit strategies.
Paul also discusses his experience as both a General Partner and Limited Partner, along with his book, Both Sides of the Table
Cowboy Capital: Raising Millions From Ranchers, Farmers & Blue-Collar Millionaires
In this episode of the Generations of Wealth Podcast, Derek sits down with Joe Rinderknecht, co-founder of Cowboy Capital, a multifamily investment firm targeting ranchers, farmers, and blue-collar investors across Montana, Idaho, and Utah. Joe shares how the work ethic and values he learned growing up on his grandfather’s cattle ranch — combined with years of hands-on construction experience — became the foundation for a multifamily portfolio that has grown to over 400 units in just the last two years.
How to Survive (and Profit From) the Next Market Downturn
In this episode of the Generations of Wealth Podcast, Derek sits down with Brandon Rickman, an experienced real estate investor with more than two decades in the business and over 500 successful house flips, to discuss what it really takes to survive—and thrive—through changing market cycles.
Brandon shares how he and his wife built a real estate business from the ground up, navigating market crashes, funding challenges, development losses, and business pivots. Together, they explore flipping, wholesaling, private lending, self-storage, masterminds, company culture, and why long-term wealth comes from adapting instead of standing still.
Turnkey Investing vs Traditional Real Estate | What Actually Works
In this episode of the Generations of Wealth Podcast, Derek sits down with Zach Lemaster, founder of Rent to Retirement, to discuss how turnkey real estate investing has evolved and why new construction is becoming an increasingly attractive strategy for long-term investors.
Zach shares his journey from serving as an Air Force Captain and practicing optometry to building one of the nation’s largest turnkey investment companies. Together, they explore market selection, passive investing, new construction versus rehabs, financing strategies, and why successful investing starts with understanding your long-term goals—not simply buying properties close to home.
Subject-To Deals Keep Failing—Here’s the Real Problem
In this episode of the Generations of Wealth Podcast, Derek sits down with Caleb Christopher, creative finance expert, consultant, and owner of Creative Title, to dive into one of the most misunderstood areas of real estate investing—creative finance.
Together, they unpack subject-to transactions, wraparound mortgages, land trusts, contract-for-deed agreements, lease options, title insurance, due-on-sale clauses, and why having the right title company can make or break a deal.
Whether you’re new to creative finance or have years of experience, this conversation is packed with practical knowledge that can help investors structure deals more safely, legally, and ethically.