Charles Carillo founder of Harborside Partners and host of the Global Investors Podcast joins Kevin to share how he went from building a billion dollar payments company to scaling a B-class multifamily portfolio. He breaks down lessons from early flips, why he exited C-class, refinancing a floating rate deal, and how he's underwriting acquisitions again amid tighter debt and flat rents. Practical, no-hype insights on buying right, protecting downside, and playing the long game in today's market.

Connect with Charles: https://harborsidepartners.com/

Highlights:

02:00 - Startup → Real Estate

04:00 - Flipping Lessons

10:00 - Shift to B-Class

13:00 - Refinancing Floating

24:00 - Debt Reality

Quote: "Real estate is a long-term play—early cash flow is modest, and you really see the fruits when you refinance or sell."

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