How to Raise Millions in Real Estate Without Sounding Salesy
In this episode of the Generations of Wealth Podcast, Derek sits down with real estate veteran Adam Gower, who has raised hundreds of millions of dollars throughout a career spanning development, distressed assets, institutional portfolios, and digital capital formation.
Adam shares lessons from decades in real estate — from the savings and loan crisis, to distressed debt sales after 2008, to building digital marketing systems that help sponsors raise capital online.
The conversation dives deep into the psychology of raising money, investor trust, authenticity, and why today’s noisy online environment makes genuine relationships more important than ever.
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.
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.
Life on Your Terms: Vision, Leadership & Real Fulfillment
In this powerful episode of the Generations of Wealth Podcast, Derek sits down with longtime mentor and leadership coach Sean McCloskey to dive deep into one of the most overlooked topics in business and life:
👉 Vision.
Sean breaks down how entrepreneurs can align their personal life and business vision, why most people feel unfulfilled even after achieving success, and how understanding the 6 basic human needs can completely change how you make decisions.
This episode is less about tactics… and more about how you think, why you act, and what truly drives fulfillment.
How to Find Real Estate Deals: FSBO, Expired & Pre-Foreclosure Leads
In this episode of the Generations of Wealth Podcast, Derek sits down with Shaun Farr from Landvoice to break down one of the most important parts of real estate investing:
👉 Finding quality deals.
Shaun shares how investors can leverage targeted data — including FSBOs, expired listings, pre-foreclosures, and distressed homeowners — to consistently generate opportunities.
The conversation focuses on lead quality, cost per acquisition, and why better data leads to better results, helping investors stop guessing and start targeting motivated sellers.
The AI Sales Combination Nobody’s Talking About
In this episode of the Generations of Wealth Podcast, Derek sits down with global entrepreneur Alaric Ong from Singapore, who scaled a business from $0 to $1.2 million in just 18 months.
Alaric shares his expertise in high-ticket sales, Facebook marketing, and AI-driven automation, breaking down how entrepreneurs can generate leads, convert sales, and scale their businesses using systems and leverage.
This episode bridges the gap between real estate investing, marketing, and modern AI tools, showing how the same principles apply across industries.
Hard Money Lending Secrets: What Lenders REALLY Look For
In this episode of the Generations of Wealth Podcast, Derek sits down with seasoned lender Michael Liuculano, who brings over two decades of experience in lending and real estate investing.
Together, they pull back the curtain on the hard money lending world — discussing how lenders evaluate deals, common mistakes investors make, and what actually protects both borrowers and lenders when things go wrong.
This is a raw, unfiltered conversation filled with real-world insights, cautionary tales, and practical advice for anyone using (or planning to use) private or hard money.
Finding Deals Before They Hit the Market
Ben Allgeyer shares his journey from leaving the medical path to becoming a full-time real estate investor, building multiple businesses, and completing hundreds of deals.
He explains how his early strategy of helping homeowners remodel before listing became obsolete as the market shifted — forcing him to pivot into flipping at scale. At one point, his team was handling 20–25 flips at a time, but the operational challenges and market changes led to another pivot into wholesaling and novations.
One of the most impactful lessons comes from a failed partnership that resulted in a $250,000 legal battle, highlighting the importance of proper agreements and structure in business.
Ben also breaks down how he built deal flow through door knocking foreclosure leads, turning it into a consistent pipeline generating multiple deals per month.
The episode dives deep into novations, explaining how they bridge the gap between wholesale and retail, allowing investors to capture more value while helping sellers avoid the traditional listing headaches.
Throughout the conversation, one theme stands out:
👉 Success in real estate comes down to action, communication, and doing what others won’t.
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.
Capital Gains Tax: The Loophole Nobody’s Talking About
If you’re a real estate investor facing large capital gains taxes, this episode could change how you think about selling property.
In this episode of the Generations of Wealth Podcast, host Derek Dombeck sits down with alternative investment specialist Jon Lontai to break down advanced strategies that investors use to defer taxes and create passive income — including 1031 Delaware Statutory Trusts (DSTs), Opportunity Zones, and other alternative investments.
Many investors know about the traditional 1031 exchange, but very few understand how DST investments can provide a passive solution while still deferring capital gains taxes.
Jon explains how DSTs work, who they’re best suited for, and why they’ve become increasingly popular among investors looking to transition away from active property management while still maintaining exposure to real estate.
If you’re thinking about selling investment property, reducing landlord responsibilities, or protecting long-term wealth, this conversation will help you understand the options available to you.