What if the discipline it takes to fly a commercial jet could also help you build a cash-flowing real estate empire?
Meet Chad Freeman — a full-time airline pilot who turned his aviation playbook into a real estate framework, scaling from single-family flips to owning mobile home parks across the Midwest. He didn't come from a trust fund or a fancy investment firm, but he used systems and smart partnerships to get him there.
In this episode of The Journey, Leo uncovers:
🧠 The mental frameworks Chad borrowed from flying planes to manage risk, checklists, and chaos in deals
💸 How he structures creative mobile home park deals for outsized returns (even when cap rates suck)
🔍 The overlooked niche he’s targeting where older operators are aging out — and how you can, too
🚫 The biggest myths about passive investing that keep high-income earners stuck
⚡ The single question he asks before every deal that filters out 90% of bad partnerships
Chad doesn’t talk like a guru. He talks like a guy who figured it out — and is still flying planes while stacking long-term wealth.
This one is for:
✅ Investors who want freedom but don’t know where to start✅ Professionals stuck in golden handcuffs looking for a smarter escape plan✅ Real estate nerds who want the real playbook (not TikTok tips)
// TIMESTAMPS
00:00 Introduction to Chad Freeman: Pilot and Investor
03:09 The Journey from Aviation to Real Estate
06:19 Lessons from Early Investments
09:16 The Changing Landscape of Mobile Home Parks
11:59 Surviving Market Cycles in Real Estate
15:40 Debunking Myths about Mobile Home Parks
17:10 The Importance of Mentorship and Coaching
21:12 Strategies for Growth in Mobile Home Parks
24:53 Implementing Systems and Checklists
29:38 Building a Team and Delegating Tasks
35:06 Hiring Virtual Assistants Effectively
40:43 Shifting Mindsets: From Scarcity to Abundance
43:17 Lightning Round: Quickfire Questions
🤝 CONNECT WITH CHADLinkedIn: https://www.linkedin.com/in/chad-freeman-90967411a/
👋 CONNECT WITH LEO1) LinkedIn: https://www.linkedin.com/in/leo-young/2) Instagram: https://www.instagram.com/leoyoungrealestate/3) Want to invest with us? https://tidycal.com/leoyoungrealestate/investor-alignment-callDisclaimer: This content is for educational and informational purposes only. It is not financial, legal, or tax advice and should not be relied upon as such. All investments carry risk, and past performance is not indicative of future results. Any mention of investment opportunities is not an offer to sell or a solicitation to buy securities. Offers, if any, will be made only through official offering documents and only to qualified, accredited investors in jurisdictions where permitted by law. Consult your own financial, legal, and tax advisors before making investment decisions.
Keywords: Chad Freeman, mobile home parks, real estate investing, aviation, mentorship, financial education, market cycles, virtual assistants, abundance mindset, investment strategies