From Federal Prison to Real Estate Success
In this episode of the Generations of Wealth Podcast, Derek sits down with Kaliya “Fuzzy” Jardine, a Hawaii real estate investor, builder, entrepreneur, and co-founder of the HUI Mastermind, for a powerful conversation about second chances, resilience, and building a completely different future.
Fuzzy openly shares his journey growing up in Hawaii, struggling with drugs, eventually selling drugs, and receiving an 87-month federal prison sentence. Instead of allowing prison to define the rest of his life, he used those years to reconnect with his faith, educate himself, study real estate, and make a decision that his old life would end there.
Today, Fuzzy owns rental properties, builds new homes in Hawaii, mentors aspiring investors, and uses his story to show others that your past doesn’t have to determine your future.
The Future of Property Management: AI, Automation & Better Systems
In this episode of the Generations of Wealth Podcast, Derek sits down with Dana Dunford, co-founder of Hemlane, to explore how technology, AI, and better systems are changing property management.
Dana shares her journey from working at Apple and Nest to becoming a real estate investor and building a property management technology company now used across approximately 107,000 rental units. Her original vision was simple but ambitious: give real estate investors the ability to know what’s happening with their rentals and manage them from virtually anywhere.
Derek and Dana also go beyond property management, discussing entrepreneurship, choosing the right investors and partners, building high-performing teams, thinking 10X instead of 2X, and why staying actively involved in real estate makes Dana better at building technology for investors.
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.