Show Notes: Boone Bowling-Show Up, Listen, Lead: How to Build Trust from Scratch

Episode 214 of The HaltingWinter Podcast Brought to you by Zencity

Overview

What happens when a 22-year-old with no political background or formal training decides to run for city council? In Middlesboro, Kentucky, it leads to transformation.

In this episode, Seth Winterhalter sits down with Mayor Boone Bowling to explore his unexpected rise from small-town kid to small-town CEO and the messy, meaningful leadership journey in between. From growing up in the office of his father’s tarp company to walking into community meetings uninvited “just to listen,” Boone’s story is a masterclass in how trust is built one room, one relationship, and one risk at a time.

With a construction management degree and a strong belief that “no one really knows what they’re doing at first,” Boone now leads a city of 10,000 that regularly serves over 37,000 people a day. His insights are practical, disarming, and full of heart and he reminds us that real leadership isn’t about polish or pedigree. It’s about showing up.

Episode Highlights:

• A Mousetrap and a Tarp: How Boone’s father turned an idea into a global tarp company and how that work ethic shaped Boone’s leadership style.

• “One Day I Might Run for Mayor”: How a frustrating moment in high school became a future calling.

• No Plan, Just Passion: What it’s really like to file for city council without knowing how a meeting works and why that kind of courage matters.

• Leadership as Listening: Why Boone walked into every community meeting he could find and what it taught him about serving people first.

• Youth Isn’t a Liability—Arrogance Is: How Boone navigated criticism about his age and chose to lead with humility and consistency.

• From Local to Regional Impact: Why a town of 10,000 can drive $452 million in commerce and how Boone is leveraging that momentum for economic growth and revitalization.

• Uncomfortable on Purpose: Why Boone believes the best leaders stay uncomfortable and why that’s a sign of progress, not weakness.

Connect with Boone Bowling

City of Middlesboro: www.cityofmiddlesboro.com

About Our Sponsor: Zencity

This episode of The HaltingWinter Podcast is made possible by Zencity—a trusted partner to hundreds of local governments around the world.

Zencity is a software that enables local government leaders to gather, understand, and act on resident feedback, going beyond the "same ten people" to actually reach residents where they're at, and incorporate that feedback into decisions large and small. To learn more about how Zencity is helping turn data into action and insight into impact:

Learn more at Zencity.io

Connect with Seth Winterhalter:

LinkedIn: www.linkedin.com/in/sethwinterhalter Website: www.HaltingWinter.com

About HaltingWinter Municipal Solutions

At HaltingWinter, we help local government leaders build thriving teams and resilient workplace cultures through keynotes, workshops, and leadership development programs rooted in the ABCs of Impactful Municipal Leadership. 

Learn more at HaltingWinter.com

Seth's Upcoming Keynotes:

2025 Kentucky League of Cities Annual Conference & Expo September 23-26 | Owensboro, KY Details at KLC

ELGL 2025 Conference | Camp Govlife October 1-3 | Santa Rose, CA Details at ELGL

2025 City Clerks New Law and Elections Seminar November 12-14 | Los Angeles, CA Details at CalCities

2025 Kansas City/County Management Association Annual Conference December 3-5 | Manhattan, KS Details at KCMA