The Generations of Wealth

📘 Overview In this episode of the Generations of Wealth Podcast , Derek sits down with Jason Wright , founder of Intentionally Inspirational, digital marketing strategist, and AI enthusiast, to discuss what actually works when it comes to marketing, raising private capital, and building meaningful relationships online. Jason shares his entrepreneurial journey from leaving the traditional 9-to-5 w...

📄 Summary Lee Yoder began his career as a physical therapist but quickly realized he was more passionate about leadership, entrepreneurship, and building businesses than practicing medicine. After reading Rich Dad Poor Dad , he recognized there was another path to financial freedom and began investing in real estate while maintaining his W-2 job. Starting with house flips and small multifamily pr...

📘 Overview In this episode of the Generations of Wealth Podcast , Derek sits down with Eric Choo , CEO of Trader Securities and a veteran of Wall Street, fintech, and capital markets, to discuss how AI is transforming investing, financial markets, and the future of decision-making. Drawing from nearly two decades in capital markets and data center investing, Eric shares lessons from the 2008 fina...

📄 Summary Todd Heitner's journey started far from real estate. Raised on a cattle ranch in Oklahoma, he found himself more interested in technology than agriculture and began learning web design during the early days of the internet. Through relationships with real estate educators and investors, Todd eventually specialized in building websites and marketing systems specifically for the real esta...

📘 Overview 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 opportunit...

📄 Summary Jon Weiskopf's career started in mechanical engineering before spending nearly two decades designing building systems and eventually leading engineering initiatives for Apple's retail real estate division. After years of corporate success, COVID and personal reflection pushed Jon to evaluate what he truly wanted from life. He realized he was building someone else's dream instead of his...

📄 Summary Trevor Thompson's career began far from real estate. He spent decades helping build and scale major entertainment brands, including Ripley's Believe It or Not, Guinness World Records, haunted attractions, and iFLY Indoor Skydiving. Despite always being interested in real estate, Trevor believed commercial real estate investing was only for millionaires. That changed when he discovered s...

📄 Summary Matthew Buchalski started his real estate journey while working for Hewlett Packard Enterprise, searching for something that gave him more ownership, freedom, and entrepreneurial fulfillment. After purchasing a successful Section 8 single-family rental on Long Island, Matt quickly realized the power of cash flow and real estate investing. Over time, he scaled into multifamily investing...

📘 Overview 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...

📘 Overview 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, De...

📄 Summary Jason Macht began his career in engineering and product management, helping build large-scale financial systems — including direct mail campaigns sending millions of pieces per month . After transitioning into real estate, he applied that same data-driven mindset to investing, focusing on scaling through multifamily properties and eventually building systems to support other investors....

📄 Summary Sean McCloskey, founder of Leadership Boardroom, shares his 19+ years of experience coaching entrepreneurs and leaders on how to align their personal vision with their business goals . A major theme in this episode is that most people: 👉 Skip vision and jump straight to strategy. Sean explains why this leads to burnout, frustration, and ultimately a lack of fulfillment — even for peopl...

📄 Summary Shaun Farr shares his journey from coaching real estate investors to working with Landvoice, where his focus shifted from teaching people how to find deals to providing the data that helps them find deals faster . The episode highlights the importance of targeted lead lists , specifically: For Sale By Owners (FSBOs) Expired listings Pre-foreclosures Distressed homeowners Shaun explains...

📄 Summary Alaric Ong shares his entrepreneurial journey, starting at age 19 and building multiple businesses before scaling his coaching and seminar business to over $1.2 million in just 18 months — without any upfront capital. A key focus of the episode is high-ticket sales , where Alaric explains why selling higher-priced offers makes it easier to become profitable compared to low-ticket produc...

📄 Summary Michael Liuculano shares his journey into lending, starting in 2002 and transitioning into hard money in 2009. With a strong background in math and finance, he built a career focused on structuring deals, underwriting risk, and helping investors succeed — while protecting capital. A major theme in this episode is risk management . Michael explains that lenders aren't partners — they are...

📘 Overview In this episode of the Generations of Wealth Podcast , Derek sits down with investor Ben Allgeyer to break down what it really takes to find and close deals in today's market. From flipping hundreds of houses to pivoting into wholesaling and novations , Ben shares the hard lessons learned through business growth, partnership mistakes, and adapting to changing market conditions. The con...

📘 Overview In this episode of the Generations of Wealth Podcast , Derek sits down with Toronto-based real estate expert Nico James-Bach to break down the evolving condo market and how it compares between Canada and the United States. Nico shares his journey into real estate, the creation of his platform CondoWiz , and how data-driven insights help investors and buyers navigate complex multi-unit...

📄 Summary Jon Lontai began his career in traditional brokerage at TD Ameritrade before transitioning into alternative investments with a fiduciary RIA. Through working with higher-net-worth clients, he discovered that traditional investment tools were no longer enough to provide meaningful value. This led him into the world of alternative investments , particularly private real estate, private de...

📘 Overview In this episode of the Generations of Wealth Podcast , Derek sits down with real estate investor and note expert Jay Redding to discuss a powerful but often overlooked strategy: creating and investing in real estate notes . Jay shares how he transitioned from fix-and-flips and rentals into the note business and why notes can produce significantly higher cash flow with fewer headaches t...

Overview: What really happens behind the scenes between investors and realtors? In this candid and insightful episode, Derek sits down with seasoned Florida broker Teresa DeMark to talk about market cycles, creative financing, assignability, lease purchases, and the realities of today's housing market. Teresa brings over 25 years of experience navigating multiple real estate cycles in Brevard Coun...

What if the biggest deal-killer in real estate wasn't price… but uncertainty? In this episode, Derek sits down with Jeremy Henley , founder of The Quick Fix, to discuss how artificial intelligence is solving one of the most frustrating parts of real estate transactions: the home inspection process. Jeremy combines years of real estate investing experience with a deep background in predictive model...

📘 Overview In this episode of the Generations of Wealth Podcast , Derek sits down with wealth advisor Jonathan Blau , a seasoned financial planner with decades of experience helping affluent families grow and preserve wealth. Rather than focusing on picking investments, Jonathan explains why behavior — not intelligence — is the biggest driver of financial success or failure . The conversation div...

🧾 Summary Joel Kraut's journey began on Wall Street, where he spent over two decades trading through major economic cycles — including the historic crash of 1987. After transitioning into real estate, he rapidly scaled a large portfolio using leverage before the 2008 crash wiped out millions and forced a hard reset. Instead of quitting, Joel rebuilt smarter — focusing on disciplined investing, st...

📘 Overview In this milestone 100th episode of the Generations of Wealth Podcast , Derek Dombeck welcomes back long-time friend, mentor, and creative real estate expert Chris Prefontaine . Chris shares his journey from losing everything in the 2008 crash to building one of the most respected creative real estate education platforms in the country. Together, Derek and Chris dive deep into creative...

📄 Summary 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 th...