Leaving Corporate America: The Real Estate Investing Journey Nobody Talks About
In this episode of the Generations of Wealth Podcast, Derek sits down with Jon Weiskopf, a former Apple engineering leader who walked away from a successful corporate career to build his own path through real estate investing, private lending, and entrepreneurship.
Jon shares his transition from designing and managing projects for Apple around the world to building a portfolio of multifamily investments, assisted living facilities, and a specialized private lending business.
The conversation explores risk, freedom, entrepreneurship, lending, real estate operations, and what it really takes to leave the security of a paycheck behind.
The Truth About Multifamily Investing in Today’s Market
In this episode of the Generations of Wealth Podcast, Derek sits down with multifamily investor and entrepreneur Matt Buchalski to discuss market cycles, distressed multifamily opportunities, raising capital during uncertainty, and the mindset required to survive difficult markets.
Matt shares his journey from corporate America into real estate investing, scaling from single-family rentals into a portfolio of over 200 units across Texas while navigating one of the most challenging multifamily environments in recent history.
This conversation is raw, honest, and packed with lessons on resilience, leadership, underwriting, and staying in the fight when markets shift.
From Direct Mail to AI: How Data is Changing Real Estate Investing
In this episode of the Generations of Wealth Podcast, Derek sits down with real estate investor and tech entrepreneur Jason Macht to break down how AI, data, and automation are transforming the way investors find and close deals.
Jason shares his journey from engineering and fintech into real estate, where he now helps investors leverage direct mail, segmentation, and AI tools to improve marketing performance and scale their businesses.
This episode blends real estate fundamentals with cutting-edge technology, showing how even non-tech investors can start using AI to create efficiency and increase deal flow.
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.
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.