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Episode 208 of The HaltingWinter Podcast – Featuring Mayor Alan Keck of Somerset, Kentucky
Brought to you by Zencity

What if your city’s next big leap forward didn’t come from a strategic plan, but from listening—really listening—to the people who live there?

In Episode 208 of The HaltingWinter Podcast, Mayor Alan Keck of Somerset, Kentucky, joins Seth Winterhalter for an eye-opening conversation on what happens when you lead with bold ideas, entrepreneurial energy, and a relentless commitment to community.

Alan’s story is as unconventional as it is inspiring. He didn’t rise through the traditional public sector ranks. He grew up in a family of entrepreneurs. He lost his first mayoral race—by 24 points. And yet, that failure became the very thing that sharpened his vision, clarified his mission, and set him on a path to transform Somerset from a sleepy lake town into a nationally recognized example of small-city revitalization.

This isn’t just a story of civic innovation—it’s a blueprint for cultural transformation.

Inside the Episode:

  • Why Alan believes the best local leaders think like entrepreneurs but lead like neighbors.
  • What it really takes to earn public trust, especially after a hard loss.
  • How Somerset created momentum by focusing on festivals, downtown vitality, and branding that actually meant something.
  • The emotional toll of leadership through crises—including COVID and an EF-4 tornado—and what it taught him about resilience and presence.
  • Why internal culture matters just as much as external outcomes and how Alan reshaped City Hall from the inside out.
  • The birth of Somerset 2050: a 25-year community-driven plan to guide growth, amplify impact, and keep city leaders aligned with public values, not just political wins.

If you’ve ever wondered how to bring your city back to life—or how to lead boldly without burning out—this is an episode you can’t miss.

Listen to Episode 208: Leading Like an Entrepreneur

Our Founding Sponsor: Zencity
This episode is proudly presented by Zencity—helping local governments turn everyday feedback into real-time insights so leaders can make confident, community-informed decisions. To learn more about how Zencity is helping turn data into action and insight into impact, visit zencity.io.

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.