Municipal Leaders: Develop Faster, Lead Stronger, Build Better
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Featuring Boone Bowling, Mayor of Middlesboro, KY
Episode 214 of The HaltingWinter Podcast
What do you do when you’re 22 years old, barely out of college, and have never been to a city council meeting but you love your town enough to fight for it?
If you’re Boone Bowling, you run for office.
Raised in Middlesboro, Kentucky, Boone didn’t set out to become mayor. In fact, he didn’t even plan to enter public service. But a single moment in high school, overhearing classmates speaking poorly of his hometown, planted a seed. Years later, that quiet conviction turned into bold action.
In this episode, Boone shares his remarkable journey from construction management grad to the youngest mayor in Middlesboro’s history. But this isn’t just a story about age. It’s about what happens when someone decides to stop waiting to be qualified and starts leading with heart, humility, and a willingness to learn on the job.
You’ll hear how Boone grew up doing homework in the conference room of his father’s tarp company (which became the #1 tarp business in the world), how he started showing up at community meetings just to listen, and how he’s now managing a city of 10,000 that serves over 37,000 people every day.
He talks about running for office without a roadmap, staying grounded through criticism, and choosing not to change who he is—long hair, beard, and all—for the sake of politics. And he opens up about the tension of serving both residents and regional visitors in a town that punches far above its weight in economic activity.
If you’ve ever wondered what it takes to lead in a small city, especially when you’re not “supposed” to be the one in charge, this episode is your playbook. It’s honest. It’s encouraging. And it’s proof that trust is earned the old-fashioned way: by showing up, listening deeply, and staying true to who you are.
Listen now: Episode 214 – Show Up, Listen, Lead
This episode is made possible by our partners at Zencity, who believe the voices of our local government leaders, and the communities they serve, deserve to be heard.
Zencity helps public sector leaders engage with the full voice of their community, not just the Same Ten People (STPs) who always show up. Through real-time data and actionable insights, Zencity empowers cities and counties to make informed decisions, respond with confidence, and build trust through transparency.
Learn more about how Zencity is transforming community engagement at zencity.io or schedule a live demo of their amazing tools at the link below.
The HaltingWinter Podcast celebrates and elevates the people who power local government. Through in-depth conversations with leaders from cities, counties, and communities of all sizes, host Seth Winterhalter explores the journeys, challenges, and innovations happening in municipal leadership across America.
