The Smarter Way to Be a Landlord: Property Management, Sustainability & Scale
David Holman shares how his real estate journey began after realizing traditional employment wouldn’t provide the lifestyle or financial security he wanted for his growing family. Starting with single-family rentals, David gradually scaled into mixed-use and small commercial properties, learning firsthand the importance of management, tenant relations, and long-term thinking.
A major theme of the conversation is treating tenants as assets, not liabilities. David explains how maintaining properties, investing in energy efficiency, and creating livable spaces leads to better tenants, fewer vacancies, and higher long-term returns.
He also walks through his experience with mixed-use buildings, triple-net leases, and why smaller commercial units can often outperform large single-tenant properties. Derek and David discuss the realities of historic buildings, the risks of deferred maintenance, and why many investors underestimate renovation and compliance costs.
The episode wraps with a deep dive into environmental upgrades insulation, heat pumps, energy efficiency, and grants showing how smart improvements can significantly increase NOI while also improving tenant quality of life.
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.
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.
From Rentals to 10,000 Units with Lane Kawaoka
In this episode, host Derek Dombeck interviews Lane Kawaoka, a former engineer turned real estate syndicator and the creator of the Wealth Elevator framework. Lane shares his journey from purchasing his first rental property while working a demanding job, to building a massive portfolio of over 10,000 multifamily units. He dives into how he transitioned from single-family investing to large-scale syndications, what to look for in deals, and why understanding your stage in the “wealth elevator” is crucial for long-term financial success.