In This Episode:
In this episode, Jim welcomes the extraordinary Chris Prefontaine, founder of Smart Real Estate Coach, for a deep dive into the mindset, structure, and discipline required to build financial freedom through creative real estate investing. Prefontaine shares lessons from the 2008 crash, explains why coaching matters, and offers practical pathways for people looking to break free from traditional financial systems and build sustainable wealth.
- Creative real estate is a discipline, not a tactic. Chris outlines a three-step approach to real estate success.
- Coaching is about accountability, not just motivation. Real transformation comes from daily tracking, public accountability, and consistent feedback—not from a one-time seminar.
- Cash flow > Nest eggs. Chris and Jim challenge conventional retirement thinking, offering examples of individuals who liquidated 401(k)s and replaced stagnant savings with income-producing assets.
Let this episode serve as a prompt to evaluate your current trajectory—are you building wealth, or just accumulating hope?
Chapters:
00:00 Intro and Real Estate Crash Lessons
01:45 401(k) to Real Estate: Breaking the Rules
02:54 How to Start in Real Estate
04:55 Commitment: The 3-to-7 Year Rule
07:35 Choosing the Right Coach
11:25 Noise in the Market and Herd Mentality
14:37 Discipline, Accountability, and Coaching Structure
18:33 Building Cash Flow and Passive Income
22:27 How to Engage with Smart Real Estate Coach
28:38 Mindset vs. Nest Egg Thinking
32:18 Best Advice Ever Received
33:21 Book Recommendation: Behind the Golden Arches
34:44 It’s Never Too Late to Build Wealth
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Connect with Chris Prefontaine:
Instagram: www.instagram.com/smartrealestatecoach
Facebook: www.facebook.com/smartrealestatecoach
TikTok: www.tiktok.com/@wickedsmartinc
YouTube: www.youtube.com/@wickedsmartinc
Linkedin: www.linkedin.com/company/wickedsmartinc/
Connect with Jim Oliver:
Facebook: CreateTailwind & Jim Oliver
Website: https://createtailwind.com/
YouTube: CreateTailwind
LinkedIn: Jim Oliver
Join the free CreateTailwind Community: https://community.createtailwind.com/
