The Generations of Wealth

🧾 Summary 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 buyi...

📄 Summary Derek interviews Jeff, his personal VA based in the Philippines, to answer the questions business owners ask most but rarely hear honest answers to. Jeff shares his background, experience working with U.S. clients, and how his role expanded from simple tasks into podcast management, CRM oversight, marketing funnels, real estate support, and operations. The episode dives deep into the hu...

📘 Overview This episode of the Generations of Wealth Podcast explores one of the most misunderstood yet powerful tools available to investors: self-directed retirement accounts . Derek is joined by Henry Yoshida , founder and CEO of Rocket Dollar, a technology-enabled self-directed IRA custodian. Henry shares why most investors even sophisticated, high-net-worth ones—don't understand how self-dir...

🧾 Summary Alan Underwood opens up about losing family members, walking away from a multimillion-dollar business, and rebuilding his life from the ground up. While many chase growth at all costs, Alan emphasizes that success without alignment leads to burnout, emptiness, and regret. This conversation goes far beyond business tactics. Derek and Alan dive into vision, gratitude, identity, legacy, an...

📘 Overview This episode of the Generations of Wealth Podcast takes a deep dive into one of the most misunderstood and risky areas of real estate investing:  raising capital legally . Derek Dombeck is joined by SEC and syndication attorney Nic McGrue , founder of Polymath Legal, who has helped clients raise and acquire over $2.5 billion in assets . Together, they break down how syndications really...

📘 Overview In this powerful 38-minute conversation, Derek and Shawn Moore dive deep into the real story behind a 25-year real estate journey filled with massive wins, devastating losses, personal challenges, and ultimate reinvention. Shawn shares how he survived losing everything twice , rebuilt from scratch, discovered the power of the short-term rental (STR) asset class, and shifted his busines...

📄 Summary In this powerful conversation, Jens shares how he left a long IT career, discovered real estate in his 40s, and grew from small four-unit buildings to thousands of multifamily and industrial square footage. He breaks down current market conditions, the pressure syndicators are feeling, and where he sees opportunities going forward. The heart of the episode centers on personal transforma...

📌 Overview 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 int...

Overview This episode maps a practical path from a professional W-2 to operator and capital raiser. Savannah explains how she identified accessible capital, learned hard lessons from early single-family turns, and pivoted to multifamily for scale. She details how to educate investors (especially healthcare peers), structure compliant raises, and maintain discipline during due diligence—even walkin...

📘 Overview In this episode, Derek sits down with self-storage powerhouse Jacob Vanderslice , who went from flipping houses in the mid-2000s to owning 41 self-storage facilities , 21,000 units , and 3.5M+ sq ft across 15 states. Jacob breaks down: • How he survived multiple market cycles • Why self-storage is still strong despite economic uncertainty • How to raise capital the right way • What inv...

Overview 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...

📋 Overview In this episode of The Generations of Wealth Podcast , Derek Dombeck sits down with Mike Deaton , a former tech executive who left corporate America after a double layoff and built a thriving land-investing business with his wife in the mountains of Colorado. Mike shares how they transitioned from W-2 jobs at Microsoft and Nokia into land flipping and owner financing , creating consist...

Overview 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...

📋 Overview In this powerful episode of the Generations of Wealth Podcast , Derek Dombeck sits down with fellow investor and mobile home park mogul Derek Vickers . What began as a door-to-door insurance hustle turned into a multimillion-dollar mobile home park portfolio spanning the Sunbelt. Vickers shares how he went from making $13,000 his first year in sales to now owning 44 parks and 2,100 lot...

Overview 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 ov...

Overview 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...

Overview 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...

Overview 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 spons...

Overview Derek sits down with Houston-based investor and capital raiser David Priest to unpack two decades of lessons: surviving the 2008 crash, shifting from transactional work to passive/commercial deals, why operator track record and conservative underwriting beat flashy pro formas, and how to protect yourself in today's capital stacks (avoid bridge debt, prefer simple structures with LPs direc...

Overview Derek sits down with David "Dave" Seymour (A&E's Flipping Boston ) for a blunt, no-fluff masterclass on thriving through market cycles. Dave shares his firefighter-to-investor story, the costly lessons behind refis and 2007, how TV fame and hard-money lending actually work, why control of capital beats "cheap" bank money, and the underwriting discipline needed now. They unpack Florida's b...

Overview Derek sits down with investor and podcaster Dustin Heiner to unpack how he went from a government IT job to becoming "successfully unemployed." Dustin shares the layoff story that sparked his pivot, why he invests strictly for monthly cash flow (not appreciation), and his "build the business first, then buy inventory" framework. They dive into systems, out-of-state teams, market cycles (i...

🎙️ Overview In this inspiring episode, Derek Dombeck sits down with his friend and mentor Kyle Wilson —entrepreneur, marketer, publisher, and former business partner of the legendary Jim Rohn. Kyle shares his journey from small-town Texas to building a global platform that promoted world-class thought leaders like Jim Rohn, Brian Tracy, Les Brown, and many more. He reveals his marketing philosophi...

📄 Summary: In this episode of Generations of Wealth , Derek Dombeck sits down with financial advisor and entrepreneur coach Brian Herriot to discuss the concept of time freedom —structuring your work and finances to create a flexible lifestyle now, rather than waiting for traditional retirement. Brian shares his personal journey from chasing early financial independence to designing a life where...

🔎 Overview: In this episode of The Generations of Wealth Podcast , host Derek Dombeck sits down with real estate investor and copywriting strategist Paul do Campo to unpack one of the most overlooked but powerful aspects of investing: lead nurturing and strategic follow-up . Paul shares how his transition from wholesaling and Lonnie deals to becoming a copy expert led him to build OmniDrip , a pr...

🧠 Episode Overview 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 t...