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."
Recommended Resources:
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- If you're a high net worth investor with capital to deploy in the next 12 months and you want to build passive income and wealth with a trusted partner, go to InvestWithKB.com for opportunities to invest in real estate projects alongside Kevin and his team.
- Looking for the ultimate guide to passive investing? Grab a copy of my latest book, The Cash Flow Investor at KevinBupp.com.
- Tap into a wealth of free information on Commercial Real Estate Investing by listening to past podcast episodes at KevinBupp.com/Podcast.
