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 deal structuring, the 3 Paydays strategy, market shifts, mindset, ethics, and why today’s market presents massive opportunity for investors who know how to operate outside traditional financing.
This episode blends experience, humor, strategy, and real-world insight—making it one of the most valuable conversations in the series.
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🧾 Summary
Chris Prefontaine recounts his early career, losing everything in the 2008 crash, and how that experience reshaped the way he approaches real estate and business. Out of that adversity came the 3 Paydays model, a creative strategy that allows investors to generate income upfront, monthly, and long-term without relying on banks.
Derek and Chris discuss why creative financing is more important now than ever, how uncertainty in the market creates opportunity, and why ethical deal structuring matters. They also touch on the dangers of misinformation in real estate education, the importance of integrity, and how the right mindset separates long-term winners from short-term speculators.
This episode also marks a major milestone 100 episodes of Generations of Wealth and highlights how relationships, not transactions, are the foundation of lasting success.
⭐ Key Takeaways
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Creative financing thrives in uncertain markets — especially when banks tighten lending.
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The 3 Paydays model creates income upfront, monthly cash flow, and long-term backend profits.
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You don’t need perfect credit or bank loans to build wealth in real estate.
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Seller financing and subject-to deals are powerful tools when done ethically.
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Market shifts create opportunity, not fear, for prepared investors.
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Doing deals the right way protects buyers and sellers long-term.
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Mindset and consistency matter more than tactics.
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The best investors adapt instead of quitting.
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Relationships outperform transactions every time.
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Success comes from action—not overthinking.
📚 Relevant Topics Discussed
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Creative real estate investing
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Seller financing & subject-to deals
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The 3 Paydays strategy
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Market cycles and opportunity
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Ethical real estate practices
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Coaching and mentorship
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Building long-term wealth
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Mindset for investors
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Avoiding common real estate pitfalls
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Creating win-win deals
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Scaling without banks
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Community-based learning
🎧 Why Should You Listen?
You should listen to this episode if you:
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Want to invest without relying on banks
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Are curious about creative real estate strategies
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Want to understand how to thrive in uncertain markets
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Feel stuck or overwhelmed by traditional investing
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Want to learn from someone who rebuilt after failure
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Value ethics, long-term thinking, and sustainable wealth
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Want real-world insight, not theory
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Are serious about building generational wealth
This episode is equal parts strategy, mindset, and real-life experience perfect for new investors and seasoned pros alike.
Important Links:
About Chris Prefontaine
Chris Prefontaine is the Chairman and Founder of Smart Real Estate Coach®, a 4x best-selling author. He is a Forbes Business Council Member and a 3-time Inc 5000 Honoree for Fastest Growing Company. Wicked Smart Community operates all over North America and has successfully completed hundreds of transactions, assisting students in doing the same.
Alongside his achievements, Chris hosts the Smart Real Estate Coach® Podcast, which ranks in the top 0.5% globally. Having navigated through challenges such as the crash of 2008, 9/11, a near-death experience with his son, and the impact of COVID, Chris reengineered his entire business to weather all storms and economic cycles.
Understanding these challenges, he helps students navigate the constantly changing real estate waters. Chris, his family, and his team’s mission focus on transforming dedicated individuals into Wicked Smart real estate investors. Chris and his wife Kim have been married for 37 years, and their adult children Nick and Kayla participate in the family business while also pursuing their own entrepreneurial ventures.