The Millionaire Real Estate Agent | The MREA Podcast

91. From Local Team to Expansion Titan With Brandon Napolitano & Jeremy Wilson

Jul 14, 2025

Jeremy Wilson and Brandon Napolitano from Chucktown Homes share their journey to a booming real estate business aiming for 2,200 transactions and $850 million in sales. Jeremy discusses his shift from the restaurant industry, emphasizing resilience and adaptability. Together, they reveal the power of effective lead conversion and the role of virtual assistants. With a focus on servant leadership, they highlight how a people-first culture can transform lives and build a successful, scalable business.

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ANECDOTE

Jeremy's Restaurant to Real Estate Journey

Jeremy Wilson started in the restaurant business from age 16 and rose to director of operations over 30 restaurants.
A poker game conversation in 2006 sparked his entry into real estate, marking a major career change.

INSIGHT

Partner with Established Local Offices

Expanding to multiple markets failed until partnership with Keller Williams for local office infrastructure.
Leveraging existing local offices and agents enabled faster scalable growth with culture and value propositions.

ADVICE

Respond Fast and Set Appointments

Respond to internet leads within two minutes; top agents respond within 30 seconds.
Set appointments immediately by asking when the lead wants to see a property to boost conversions.

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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.

Resources:

Follow Up Boss – CRM used by Chucktown Homes
Sisu – Real estate tracking and accountability platform
Homeward – Cash offer and alternative listing solutions
Listen: Episode 43. Go Small to Go Big With Tim Heyl
Order the Millionaire Real Estate Agent Playbook | Volume 2

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