Why Your Real Estate Strategy Is Failing (It’s Not The Math)
In this episode of the Generations of Wealth Podcast, Derek talks with Denis Shapiro, founder of SIH Capital Group, about the hard lessons he learned moving from single-family landlord to limited partner to full-time syndicator — and why he believes charismatic marketing, crowdfunding platforms, and even AI will never replace the relationship-driven side of real estate.
How to Legally Pay Only 2% Tax
In this episode of the Generations of Wealth Podcast, Derek talks with Mike Milligan, CFP and founder of One Oak Financial, about why most people don’t actually have a financial plan — they have a pile of products disguised as one. Mike also opens up about relocating to Puerto Rico for a legal tax structure that’s dropped his effective tax rate to around 2% on exported business income.
Tax Deed Investing: How to Find Hidden Off-Market Deals
In this episode of the Generations of Wealth Podcast, Derek sits down with John Bonillas, a real estate investor, contractor, and tax deed specialist from San Antonio, Texas.
John shares how he transitioned from coaching, teaching, and the fitness industry into real estate investing through tax delinquent foreclosure auctions. He breaks down the process of finding tax deed opportunities, researching properties, understanding redemption periods, avoiding costly mistakes, and identifying areas poised for future growth.
This episode is packed with practical insights for investors looking to find off-market opportunities, purchase properties below market value, and create more freedom through real estate investing.
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.
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.