Real Estate Investing for Cash Flow with Kevin Bupp #959 Payments to Properties: Charles Carillo's B-Class Multifamily Playbook
Oct 27, 2025
Charles Carillo, founder of Harborside Partners and former payments entrepreneur, scaled from fintech to B-class multifamily investing. He discusses shifting from flips and C-class to B-minus/B assets. Topics include refinancing floating-rate deals, underwriting amid tighter debt and flat rents, protecting downside, and why long-term holds matter.
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Payments Business Fueled Real Estate Start
- Charles built a payments business after college and used its cash flow to invest in real estate.
- His dad's multifamily experience guided him into apartments as a safe place to park capital.
Flipping Taught Limits Of One-Off Deals
- Charles tried house flipping after college and found execution and inconsistent deal flow painful.
- He concluded multifamily scaled better and offered a steadier long-term place to put capital.
Move Up To B-Class To Protect Downside
- Transition from C-class to B-class properties to reduce tenant-credit and operations risk.
- Charles sold C-class assets after COVID-related collections pressure and favored higher-quality assets.