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Mar 30, 2026 38 min

Legacy Is Not What You Leave Behind

from Commercial Real Estate School Hosted by Kyle Inserra

Gino Barbaro was shoveling snow outside his restaurant at midnight — no gloves, no customers, no paycheck, when he looked up and saw a light on in the apartment above. His mother was home, asleep, getting paid. He wasn't. That was the moment. From that parking lot, Gino went on to co-found the Jake and Gino platform, scale over 1,500 multifamily units in under five years, and transact north of $350 million in assets all anchored to a framework that fits in three words: buy right, manage right, finance right. In this episode, Kyle and Gino get into: Why the restaurant business is the best and worst training ground for real estate The buy right, manage right, finance right framework — and exactly where operators violated every tenet of it in 2021 and 2022 Why no deal is better than a bad deal, and how hope became the most expensive underwriting assumption in the last cycle The "I'm-a mentality" — why the instinct that gets you started is the ceiling that caps you Values-based investing: the deal Gino walked away from that would have made him over half a million dollars What Gino learned as a Certified Money Coach about why some investors close and others — with better balance sheets — never do Legacy as something you activate today, not something you leave behind If you've ever wondered whether the grind is worth it, whether the timing is right, or whether you're building something that actually lasts — this one's for you. 🔗 Jake & Gino: jakeandgino.com🔗 Barbaro 360: barbaro360.com🔗 Follow Gino: @ginobarbaro on social Follow CRE School on Social LinkedInhttps://www.linkedin.com/company/commercial-real-estate-school/?viewAsMember=true Instagramhttps://www.instagram.com/creschoolshow/

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Legacy Is Not What You Leave Behind

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This episode was published on March 30, 2026.

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