From $100K Deals to a $1B Real Estate Fund: Institutional Capital, Military Discipline & Unfiltered Truth

In this episode of the Capital Raiser Show, Richard C. Wilson interviews John Lettera, co-founder of Fairbridge Asset Management, a real estate debt platform backed by institutional investors like Oaktree Capital. With 30+ years of experience, John shares his no-nonsense approach to real estate, how military discipline shaped his investing style, and how authenticity and downside risk focus helped him scale from $100K Bronx deals to managing $1B+ nationally.

Topics covered include:

• What institutional investors really look for

• Why walking every property matters more than AI

• Mistakes investors make with equity offers

• The power of saying no and staying in your lane

• Deal flow as your best capital-raising strategy

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