Episode 71: The Property Boss: A Lifetime of Lessons in Real Estate with Paul Carassone

Seth Glasser and Matt Gault sit down with Paul Carassone, known on the internet as The Property Boss, for a wide-ranging conversation on a lifetime spent owning, operating, and investing in multifamily real estate. Paul shares how his early years working in his family’s grocery business and alongside his father in Bronx apartment buildings shaped the hands-on approach that eventually helped him build a prolific multifamily portfolio in the Hudson Valley. He shares the practical lessons that come from decades of experience, from understanding buildings and managing tenants to controlling costs and navigating the day-to-day realities of operating real estate, a business that's not as "passive" as many people think. Paul also weighs in on today’s NYC multifamily market, why he believes current Bronx pricing represents a generational buying opportunity, and why investors willing to ride out the current political cycle could see significant upside. The conversation then turns to the other side of investing: knowing when to sell, planning an exit strategy, navigating 1031 exchanges and DSTs, and deciding what life will look like after selling This episode offers an unfiltered look at what it actually takes to build wealth in real estate—and how to prepare for the next chapter. Get the latest updates on Instagram: https://www.instagram.com/newyorkmultifamily https://www.newyorkmultifamily.com Reach out to us at: seth.glasser@marcusmillichap.com