#959 Payments to Properties: Charles Carillo's B-Class Multifamily Playbook
Real Estate Investing for Cash Flow with Kevin Bupp
Kevin Bupp
4.8 • 679 Ratings
🗓️ 27 October 2025
⏱️ 33 minutes
🧾️ Download transcript
Summary
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:
- Accredited Investors, you're invited to Join the Cashflow Investor Club to learn how you can partner with Kevin Bupp on current and upcoming opportunities to create passive cash flow and build wealth. Join the Club!
- 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.
Transcript
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| 0:00.0 | You've been searching for the best way to generate passive income in your life and heard that real estate is a great way to do it. |
| 0:09.4 | But you're tired of all the so-called gurus who are all talk and no substance. |
| 0:15.2 | Get ready to celebrate because Kevin Buck has spent 14 years successfully making it happen. |
| 0:21.7 | This is the Real Estate Investing for Cash Flow podcast. |
| 0:25.2 | Now, here's Kevin Bup. |
| 0:30.3 | Hey guys, Kevin Bup here, and I want to welcome it to another episode of the Real Estate |
| 0:33.8 | Investing for Cashflow podcast. |
| 0:35.6 | Our mission is to help you build and maintain massive amounts of cash flow through income |
| 0:39.7 | producing real estate investments. |
| 0:41.9 | Now, today, guys, I'm excited to welcome Charles Carrillo to the show. |
| 0:45.5 | Charles is the founder and managing partner of Harborside Partners. |
| 0:48.5 | And since 2006, Charles has been involved in over $200 million worth of real estate transactions. |
| 0:55.3 | Now, he's got extensive experience in renovating and repositioning multifamily and commercial |
| 1:00.1 | properties, while also passively investing across diverse asset classes from just general |
| 1:05.7 | commercial real estate to ag tech startups. |
| 1:08.4 | Now at Harborside, Charles oversees acquisitions, investor relations, and strategic |
| 1:12.8 | partnerships. He's also the host of the popular global investors podcast where he interviews |
| 1:18.7 | successful investors from around the world. Now, we'll get into this here today. Before he |
| 1:23.4 | got into real estate, Charles co-founded an online payment processing company that |
| 1:28.6 | went on the handle over a billion dollars in payments across five continents. And so, you know, |
| 1:33.2 | really, guys, his entrepreneurial journey and diverse investing experience really give him, |
| 1:37.7 | you know, what I'd say is a global perspective on building wealth, scaling businesses, |
... |
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