What I Learned About Raising Money for Real Estate with John Casmon, Ep. 771

In this guest appearance on the Investor Fuel – Real Estate Mastermind podcast, John Casmon shares his journey from working in corporate advertising to building a $150M multifamily portfolio. He opens up about his employer filing bankruptcy during the 2008 financial crisis, house hacking in Chicago, and discovering the power of mentorship and raising capital. With clarity, honesty, and strategic insight, John lays out a realistic roadmap for transitioning from W-2 work to full-time real estate investing—and how mindset and mission can elevate your ability to serve others through multifamily.

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Key Takeaways

• How the 2008 financial crisis sparked John’s journey into real estate

• House hacking a duplex and scaling to an eight-unit with personal savings

• The financial trap of saving to buy—why John pivoted to raising capital

• The value of mentorship and how one post on BiggerPockets changed everything

• John’s 3 Cs framework for raising capital: Confidence, Credibility, and Connections

• How to build trust with passive investors by educating, not convincing

Topics

Corporate Roots and a Harsh Wake-Up Call

• John’s early career in advertising at General Motors

• How the 2008 financial crisis sparked the need for a financial plan B

From House Hack to Portfolio Growth

• Buying a three-unit with his wife in Chicago

• Scaling to an eight-unit using all of their savings—and realizing it wasn’t scalable

Discovering the Power of Mentorship

• Finding a coach via BiggerPockets and lunch in Cincinnati

• Why mentorship helped shift his mindset, strategy, and results

Learning to Raise Capital

• Moving beyond the myth of needing wealthy friends or family

• The mental shift from “asking for money” to “offering a service”

Education as a Tool for Connection

• Building trust with passive investors through consistent education

• How one friend declined to invest nine times—then came back for the tenth

The 3 Cs of Raising Capital

• Confidence: Built through preparation and market knowledge

• Credibility: Leaning on your experience and team

• Connections: Expanding beyond friends and family to reach aligned investors

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Next Steps

• Clarify your goals before you start raising capital or choosing strategies

• Focus on education and service—not pressure—when building investor relationships

• Use the 3 Cs: Confidence, Credibility, and Connections

• Don’t go it alone—mentorship can accelerate everything

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