From Mortgage Broker to Fund Manager: Real Estate Lessons That Matter
In this episode of the Generations of Wealth Podcast, Derek sits down with investor and lender Will Harvey to discuss hard money lending, private funds, underwriting risk, and the importance of staying humble in changing market cycles.
Will shares his journey from mortgage lending into flipping houses, apartment syndications, and eventually launching his own lending fund. Together, Derek and Will break down the realities of leverage, underwriting, investor protection, and why many people underestimate risk during strong markets.
This episode is packed with practical insight for anyone interested in private lending, raising capital, or building long-term wealth through real estate.
Inside the Condo Market: Inventory, Interest Rates & What’s Coming Next
Nico James-Bach began his real estate journey assisting his mother in commercial and industrial transactions before transitioning into residential real estate. Recognizing a major gap in accessible, organized condo data, he built CondoWiz, a platform designed to centralize information on multi-unit communities including condos, rentals, hotels, and long-term care facilities.
The discussion highlights Toronto’s housing dynamics — a highly dense market where vertical development dominates due to limited land availability. Nico explains how recent years have created a “perfect storm” of high condo inventory, rising interest rates, and investor pullback, leading to short-term price softening.
However, he emphasizes that this is cyclical. With fewer new projects being started, the market could face a future supply shortage within 2–3 years, potentially driving prices back up.
Derek and Nico also compare U.S. vs Canadian lending structures, interest rates, leasing regulations, and condo ownership rules. They explore how government policies shape investment strategies and why understanding local market dynamics is critical.
The episode closes with Nico’s vision for expanding CondoWiz across Canada and into major U.S. cities, along with insights into his personal passions and long-term goals.
Market Cycles, Creative Deals & What Most Agents Don’t Understand
Teresa DeMark shares her journey as a long-time Florida broker managing sales, rentals, and commercial properties. Having survived multiple real estate cycles—including the 2007 crash—she offers a grounded perspective on what’s happening today.
Derek and Teresa explore the tension between creative investors and traditional agents, unpacking misunderstandings around assignability, wholesaling, subject-to transactions, and lease purchases.
They also address:
The new real estate commission laws
Steering concerns and compliance issues
Why many agents lack deeper real estate knowledge
The importance of ethics and integrity in investing
Creative ways to help sellers get full value
Why now may be the time to buy in certain markets
The episode highlights the power of collaboration between knowledgeable agents and ethical investors.
Think Like an Investor: Market Cycles, Smart Deals & Building Real Wealth
What separates investors who survive from those who thrive? It’s not just deals it’s how they think.
In this powerful conversation, Derek Dombeck sits down with veteran investor and former Wall Street trader Joel Kraut to unpack decades of experience navigating market crashes, rebuilding wealth, and mastering the psychology of investing.
Joel shares lessons from losing millions during the housing collapse, why relationship capital matters more than ever, and how today’s investors can position themselves to win in shifting markets. From creative deal structuring to partnership strategy and leveraging technology, this episode delivers real-world wisdom that applies whether you’re new to investing or scaling a serious portfolio.
If you want to build a life you love not just survive this episode is a must-watch.
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 to Survive a Real Estate Crash in 2025
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 boom-bust dynamics, pivoting plays (from land to pickleball to flex), building real networks (and a strict “no-a**hole policy”), and Dave’s 2025–26 plan: scalable education + cherry-picked commercial deals—grounded in faith, family, and service.
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.