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.
Links & Tools from This Episode:
Follow Up Boss – CRM used by Chucktown Homes:
https://www.followupboss.com/Sisu – Real estate tracking and accountability platform:
https://sisu.co/Homeward – Cash offer and alternative listing solutions:
https://www.homeward.com/Listen to Episode 43. Go Small to Go Big With Tim Heyl:
https://podcasts.apple.com/us/podcast/43-go-small-to-go-big-with-tim-heyl/id1712458115?i=1000665020102Order the Millionaire Real Estate Agent Playbook | Volume 2:
https://kwredlabel.com/products/millionaire-real-estate-agent-playbook-version-2Become your clients’ go-to Airbnb expert
Airbnb has launched a Real Estate Referral Program for agents just like you. When you refer clients to list their properties on Airbnb, you not only earn a referral fee, you also gain access to localized market data that helps you stand out in your market. It’s free to join, includes a quick-start webinar, and gives you real-time insights on booking trends in your area. It’s a win-win-win. Sign up at
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Produced by NOVA:
https://novapodcasting.com/ This podcast is for general informational purposes only. The views, thoughts, and opinions of the guest represent those of the guest and not Keller Williams Realty, LLC and its affiliates, and should not be construed as financial, economic, legal, tax, or other advice. This podcast is provided without any warranty, or guarantee of its accuracy, completeness, timeliness, or results from using the information.
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