208: Alan Keck: Leading Like an Entrepreneur: Risk, Resilience, and Reinventing Local Government
Release Date: 07/29/2025
212: Steve Dalton: Debt-Free Isn’t Growth: Infrastructure, Integrity, and the Impossible Annexation
The HaltingWinter Podcast
Show Notes: Steve Dalton: Debt-Free Isn’t Growth: Infrastructure, Integrity, and the Impossible Annexation Episode 212 of The HaltingWinter Podcast Brought to you by Overview In this episode, Seth Winterhalter sits down with Steve Dalton, City Administrator of Branson West, Missouri—a small town with 500 residents, million-dollar infrastructure, and a story that defies every assumption about rural government leadership. From a childhood on a farm with no running water to a reluctant entry into law enforcement, Steve’s journey is anything but traditional. After years in narcotics...
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211: Kathy O'Nan: Beyond the Tornado: Presence, Pressure, and the Power of Local Leadership
The HaltingWinter Podcast
Show Notes: Kathy O'Nan: Beyond the Tornado: Presence, Pressure, and the Power of Local Leadership Episode 211 of The HaltingWinter Podcast Brought to you by Overview In this powerful episode, Seth Winterhalter sits down with Kathy O’Nan, Mayor of Mayfield, Kentucky, a retired teacher turned public servant whose life was forever changed on December 10, 2021, when a catastrophic EF-4 tornado ripped through the heart of her city. What followed was a story of leadership under fire, community resilience, and a fierce refusal to give up. Kathy shares the emotional and practical realities...
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210: Book of the Week: Who Moved My Cheese?
The HaltingWinter Podcast
Show Notes: Book of the Week – Who Moved My Cheese?Episode 210 of The HaltingWinter Podcast (Part 1 of 5: Who Moved My Cheese? Series) Episode Title: When Change Catches Municipal Leaders Off Guard Episode Overview The federal grant you've relied on for three years just got eliminated. Your most experienced department head announced retirement. The state passed new regulations that completely change how you deliver services. Your first instinct might be frustration, analysis, or hoping things return to normal but what if these moments are actually opportunities to become a more...
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209: Laura Philpot: Vision Over Ego: A Shift from Big Projects to Real Impact
The HaltingWinter Podcast
Show Notes: Laura Philpot: Vision Over Ego: A Shift from Big Projects to Real Impact Episode 209 of The HaltingWinter Podcast Brought to you by Overview In this episode, Seth Winterhalter sits down with Laura Philpot, City Manager of Maple Valley, Washington, to explore how a career rooted in public works evolved into a leadership philosophy centered on people, not prestige. Laura’s journey began with a love for math, a concrete canoe competition, and a fascination with big infrastructure projects. But over time, through building bridges, programming traffic lights, and stepping into...
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208: Alan Keck: Leading Like an Entrepreneur: Risk, Resilience, and Reinventing Local Government
The HaltingWinter Podcast
Show Notes: Alan Keck: Leading Like an Entrepreneur: Risk, Resilience, and Reinventing Local Government Episode 208 of The HaltingWinter Podcast Brought to you by 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...
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207: Book of the Week: Orbiting the Giant Hairball
The HaltingWinter Podcast
Show Notes: Book of the Week – Orbiting the Giant HairballEpisode 207 of The HaltingWinter Podcast (Part 1 of 5: Orbiting the Giant Hairball Series) Episode Title: When Your City Hall Becomes a Giant Hairball: Breaking Free from Bureaucratic Gravity Episode Overview Your organization is accumulating policies faster than it's eliminating them, and this bureaucratic mass is quietly undermining your ability to serve your community effectively. In this kickoff episode of our series, Seth Winterhalter explores how municipal governments become trapped in what Gordon MacKenzie called...
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206: Sandra Fournier: Filling Potholes in Heels: What it Takes for Bold Leadership in the Face of Bureaucracy
The HaltingWinter Podcast
Show Notes: Sandra Fournier: Filling Potholes in Heels: What it Takes for Bold Leadership in the Face of Bureaucracy Episode 206 of The HaltingWinter Podcast Brought to you by Overview In this episode, Seth Winterhalter sits down with Sandra Fournier, the remarkable Town Manager of Mapleton, Castle Hill, and Chapman, Maine. From a teenage mother without a high school diploma to leading not just one, but three municipalities at the same time, Sandra’s story is one of grit, growth, and grounded leadership. She opens up about growing up in poverty, the power of second chances, and the pivotal...
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205: Daron Jordan: Grants, Grit, and the Quiet Wins That Build Cities
The HaltingWinter Podcast
Show Notes: Daron Jordan: Grants, Grit, and the Quiet Wins That Build Cities Episode 205 of The HaltingWinter Podcast Brought to you by Overview In this episode, Seth Winterhalter sits down with Daron Jordan, City Manager of Paducah, Kentucky, to explore a career that started poolside and led all the way to the city manager’s seat. From selling boat stickers as a teenager to becoming the first full-time program and aquatics director in his hometown, Daron’s story is a masterclass in how local government leaders are formed, not in textbooks, but in the trenches. Daron opens up about the...
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204: Book of the Week: Reality-Based Leadership
The HaltingWinter Podcast
Show Notes: Book of the Week – Reality-Based LeadershipEpisode 204 of The HaltingWinter Podcast (Part 1 of 5: Reality-Based Leadership Series) Episode Title: Beyond City Hall Drama: Leading with Reality Instead of Stories Episode Overview Your team's energy is being drained by something you can control, but most municipal leaders don't recognize it's happening. In this kickoff episode of our series, Seth Winterhalter explores how drama, blame, and resistance consume the energy your organization needs for serving your community. Drawing from Cy Wakeman's helpful research, we...
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203: Wesley Young: From Comfort to Calling: Choosing the Hard Path of Local Impact
The HaltingWinter Podcast
Show Notes: Wesley Young: From Comfort to Calling: Choosing the Hard Path of Local Impact Episode 203 of The HaltingWinter Podcast Overview In this episode, Seth Winterhalter welcomes Wesley Young, City Administrator of Willard, Missouri, for a conversation that’s part memoir, part masterclass on finding purpose in public service. Wesley’s journey spans continents, careers, and courageous decisions, from growing up in England and overcoming dyslexia to building a life of service in the American Midwest. Along the way, he chose the hard path: leaving the safety of state government for the...
info_outlineShow 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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