Show Notes: Alan Keck: Leading Like an Entrepreneur: Risk, Resilience, and Reinventing Local Government

Episode 208 of The HaltingWinter Podcast Brought to you by Zencity

Overview

In this episode, Seth Winterhalter sits down with Alan Keck, Mayor of Somerset, Kentucky, to unpack what happens when you bring an entrepreneurial mindset into City Hall. From a teenage calling into public service to losing his first election by 24 points, Alan’s journey is anything but conventional—and that’s exactly why it’s so compelling.

Alan shares how growing up in a family of business owners shaped his approach to leadership, why failure was his greatest teacher, and what it really takes to earn trust from the inside out. He doesn’t shy away from the political grind, the emotional cost of leading through tornadoes and pandemics, or the challenge of bringing vision to life in a city that once feared change.

This is a conversation about bold moves, public humility, and the cultural transformation that happens when leaders stop asking for permission and start building something better. If you're a city manager looking to create momentum, a mayor navigating pushback, or anyone wondering what reinvention looks like in real time, this episode is for you.

Episode Highlights:

When Vision Meets Resistance Alan opens up about the heartbreak of losing his first election and how it fueled a comeback that rewrote Somerset’s future.

From Private Sector to Public Seat What entrepreneurs bring to local government and what they have to unlearn to lead well in the public square.

Campaigns Are Culture-Building Why running for office is the ultimate leadership litmus test and how it changes how you see your residents forever.

From Festivals to Fiber How Alan turned “Light Up Somerset” into more than just events—it became the heartbeat of a cultural revival.

COVID, Tornadoes, and Community Lessons in presence, pressure, and perspective when the playbook gets ripped up and the city still needs answers.

Trust Over Control Inside the leadership philosophy that turned 300 city employees into city ambassadors.

Planning with Purpose Why Somerset 2050 isn’t just a comprehensive plan—it’s a community blueprint designed to outlast any one administration.

Connect with Alan Keck

LinkedIn: www.linkedin.com/in/alan-keck Somerset 2050 Plan: www.cityofsomerset.com/2025

About Our Sponsor: Zencity

This episode of The HaltingWinter Podcast is proudly sponsored 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, click the link below.

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 24 | Owensboro, KY Details at KLC

2025 Kansas City/County Management Association Annual Conference December 4 | Manhattan, KS Details at KCMA

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