What does it take to build a billion-dollar real estate business across multiple cities and states? Jeremy Wilson and Brandon Napolitano of Chucktown Homes join us to reveal how they’re pacing over 2,200 transactions and $850 million in annual production—all while keeping their culture fiercely people-first. Jeremy traces his path from the restaurant grind to real estate, sharing how resilience, adaptability, and an “all-in” mindset fueled their rise through short sales, REOs, and beyond. Along with Brandon, his chief of sales, they break down the systems and simple frameworks that let their team convert aggregator leads at the highest level. With a single hub in Charleston, the team runs on a network of local leaders and virtual assistants all connected through strong systems and a culture that feels like family.
But above all, this conversation is about servant leadership and building a business that changes lives—from rookie agents breaking through, to support staff thriving half a world away. If you’re ready to see how the best keep things are simple, scalable, and deeply human, this is the episode you need to hear.
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