The Sidewalk CEO
The Sidewalk CEO
Podcast Description
The Sidewalk CEO is an opportunity for local entrepreneurs to share their stories. Sheri and Leo have over 60 years of experience in business and industry, large and small.
Podcast Insights
Content Themes
The podcast focuses on local entrepreneurship, business challenges, and community involvement, with episodes covering topics like innovative business models, personal resilience during COVID-19, and the importance of community support in small business success. For example, episodes discuss the journey of multi-generational businesses like Rebecca Ruth Chocolates and family-run establishments like The Evergreen.

The Sidewalk CEO is an opportunity for local entrepreneurs to share their stories. Sheri and Leo have over 60 years of experience in business and industry, large and small.
In this episode of The Sidewalk CEO, hosts Leo Haggerty (TCHQ Communications) and Sherri Donahue (Commonwealth Sentinel Cybersecurity) sit down with Laura Cullen Glasscock, the editor and publisher of The Kentucky Gazette.
Laura has more than 30 years of experience covering Kentucky politics and state government. From her early days working under the late Lowell Reese to eventually purchasing the Gazette herself, Laura has seen—and shaped—how insider political journalism informs policymakers and citizens alike.
What You’ll Hear in This Episode:
- 🎙️ Laura’s journey from teaching at Kentucky State University to pursuing graduate studies in journalism and stepping into political reporting.
- 📰 The history of the Kentucky Gazette—founded in 1787, before Kentucky even became a state—and its transformation into today’s insider journal on politics and government.
- 🔍 Why the Gazette focuses on analysis and records-driven reporting instead of breaking news.
- 💡 The challenges of running an independent publication in a corporate-media-dominated world.
- 🗳️ Stories of Kentucky politics, from campaign finance investigations to election coverage.
- 📉 How COVID-19 and corporate consolidation have reshaped political journalism in Kentucky.
- 📱 A candid discussion on misinformation, TikTok “news,” and the importance of journalistic ethics.
- 💼 Lessons Laura wishes she knew before buying the Gazette—especially about balancing journalism with the business side of publishing.
- 📣 Advice for small-market media outlets on how to survive: stay hyperlocal, cover what others don’t, and build trust.
Why You Should Listen
This episode is more than a conversation about journalism; it’s a look at the changing landscape of media, politics, and public trust. Whether you’re a business owner, media professional, or simply curious about Kentucky’s political ecosystem, you’ll find insights you won’t get anywhere else.
Resources & Links
- Learn more about the Kentucky Gazette: https://kentuckygazette.com/
- The Gazette on Twitter

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