Episode Summary Jeff Gregory is a third-generation Elizabethtown native, a 22-year Kentucky State Police veteran, and the mayor of Elizabethtown, Kentucky — a city that has grown from 14,000 residents to nearly 37,000 on his watch. In this episode, Andrew Schory and Jeff sit down for a candid conversation about what a mayor actually does, how Elizabethtown navigates the growing pains of a city that serves as the regional hub for ten surrounding counties, how city and county government differ, and what Jeff has learned about leadership, humility, and getting out of good people's way. It's a conversation about city building, public trust, and the principle that's driven eight years in office: stay humble, and remember you're only as strong as your team. Guest Information Guest Name: Jeff Gregory, Mayor, City of Elizabethtown, Kentucky Bio: Jeff Gregory is the Mayor of Elizabethtown, Kentucky, first elected in November 2018 and now serving his second term. A third-generation Etonian with deep roots in Hardin County — Jeff spent 22 years in law enforcement, retiring from the Kentucky State Police in 2018 before stepping into the mayor's office. Under his leadership, Elizabethtown has grown to nearly 37,000 residents, built a Steel Grove Amphitheater (opening spring 2027), expanded its industrial base to more than 12,000 jobs, and invested in the public safety, infrastructure, and nonprofit partnerships that serve both residents and the tens of thousands of daily visitors from surrounding counties. Jeff is married to Melissa and is the father of four children: Jay, Ryder, Harper, and Emerson. City of Elizabethtown: elizabethtownky.gov Episode Outline From Trooper to Mayor: Why Jeff Gregory Ran for Office (00:35) Jeff traces a path rooted in three generations of Elizabethtown civic life. He always assumed he'd run for sheriff — until John Ward, his State Police post commander and close friend, had that role well in hand. When the mayoral opportunity emerged, he ran in 2018 and won. He describes the transition from law enforcement to elected office as a natural one: both roles, at their core, are about dealing with people, finding solutions, and making a community safer. The main difference? In law enforcement, he could dictate where a difficult encounter ended. In the mayor's chair, sometimes you just have to take what you get and keep working. 14,000 to 37,000: What Growth Really Costs a City (02:20) Elizabethtown has more than doubled in population since Jeff was a teenager, and the pace has accelerated. Growth brings amenities — the Etown Sports Park, the Steel Grove Amphitheater, expanded retail, regional healthcare, and a community college — but also genuine infrastructure strain. Stormwater is the challenge Jeff names first: Elizabethtown sits in a historic valley with streams and creeks woven throughout, and microburst rains of five inches in two hours are now arriving three to four times a year. Systems designed for a smaller city aren't keeping up, and infrastructure investment is a constant priority. Mt. Pilot to Ten Mayberries: Understanding E-Town's Regional Role (05:29) Jeff's most clarifying framing of the episode: Elizabethtown is the Mt. Pilot to ten surrounding Mayberries. Meade, Breckenridge, Grayson, Nelson, Hart, Larue, and other counties come to Elizabethtown for healthcare, education, employment, and the amenities that residents of those communities once drove to Louisville to access. The city's official population is roughly 37,000 — but its daytime population is estimated at close to 100,000. Traffic congestion is not simply a growth problem; it is a regional hub problem, and the distinction matters for how city leadership plans and communicates. CEO and Board of Directors: How the Mayor and City Council Work (07:47) Jeff's framing is clear and practical: the mayor is the CEO; the city council is the board of directors. The council passes ordinances and signs off on municipal orders; the mayor executes and leads the team that implements. What makes it work is communication — Jeff makes a point of ensuring every council member hears about upcoming decisions before a formal meeting, so they have time to form a position rather than being surprised. His principle: when the legislative body and the executive body are not getting along, the whole organization is unproductive. He will not let that happen. Homelessness, Food Insecurity, and the Limits of Government (12:51) Elizabethtown invests approximately $550,000 annually in local nonprofits — Helping Hand of Hope, Hope Academy, Feeding America, Warm Blessings, Room in the Inn, and others — to address homelessness and food insecurity. Jeff is candid about two things: throwing money at a problem rarely makes it go away, and managing the political divide between constituents who want more intervention and those who see it as wasteful is a constant challenge. His frame is economic as well as humanitarian: the goal is to move people from below the tax bracket to above it, so they are contributing rather than drawing. A coordinated plan for how the city, police department, and nonprofits will work together is close to being announced. "Let Them Eat": How Jeff Builds and Leads His Team (23:37) Jeff's philosophy of leadership comes through clearly in how he deflects credit. He describes his city clerk, city administrator, city attorney, marketing director, and business development director as among the best in the state — and says the one thing he can genuinely take credit for is going out and finding them. His analogy: a great coach's job is made easy by great players. Once you have them, you let them eat — you get out of their way and let them use their talents. Andrew and Jeff connect this to their shared experience as teammates, and to the coaches who modeled it for both of them growing up. Trust the Process: What Jeff Asks of Elizabethtown's Citizens (27:57) Jeff's ask of the community is direct: participate, and trust. His record includes no scandals, no misappropriation, and a clear commitment to saying what they will do and doing it — and owning it when they get something wrong. In a national environment where distrust of government is at an all-time high, Jeff believes that consistent honesty and transparency are the only long-term answer. If you have a concern, come see him. If you don't like something after it's done, come see him. He'll explain the process. Andrew adds the frame: assume positive intent. Speed Round Highlights (25:44) Books Mentioned • Good to Great by Jim Collins — Jeff's most impactful leadership read; he keeps a copy on his desk and applies its principles to city government, aiming for great while knowing perfect is the real target How to Get Involved in Elizabethtown • Serve on a city board or commission • Volunteer at city events — the event staff can always use help, especially as the city's calendar continues to grow. • Bring your skills to the table — call the mayor's office and let them know what you can offer. • Trust the process — and if you have concerns, go directly to the source. Jeff's door is open. Learn more about the City of Elizabethtown at elizabethtownky.gov Host & Show Info Host: Andrew Schory, Business Coach About the Host: Andrew Schory is a business coach dedicated to helping leaders build momentum through small, intentional actions. Each episode of the Small Stones Podcast features conversations with business and thought leaders to uncover the habits and decisions that move life and business forward — one small stone at a time. Podcast Website: smallstonespodcast.com Community • Rate & Review on Apple Podcasts — The most impactful way to support the show and help other listeners find it. • Work with Andrew: Interested in one-on-one or group business coaching? Visit smallstonespodcast.com to schedule a session. • Join the Mailing List: Get tools, insights, and episode updates at smallstonespodcast.com Share this episode with anyone who lives in or loves Elizabethtown, or with any leader who needs a reminder that the best thing you can do for a great team is get out of their way and let them go.
