Insurance Town

In this weeks episode, the mayor sits down with his good friend Tinsley English to discuss her latest book titled Grit, Growth & Gumption. But this episode is way beyond that we discuss being a leader in this service industry. We discuss the challenges, the customer service, reps face, the challenges that managers face.

We also discuss accepting God’s calling in your life no matter how difficult that might be, or sc...

In this episode, the Mayor sits down with industry veteran Jeff Kleid  a 30-year insurance innovator, MGA, and carrier leader  to talk about the business of hard-to-place risks, the truth about captives, and how brokers can turn complex accounts into profitable opportunities.

From selling insurance on the internet in the ‘90s to building niche programs for cannabis, film, and trucking, Jeff shares real-world lessons about t...

In this weeks episode of Insurance Town, The Mayor welcomes good buddy Patrick McBride to the show. Patrick, a seasoned insurance professional, shares his journey, experiences, and insights on the industry's evolving landscape.

Key Highlights:

• The Last Few Years in the Industry: Patrick reflects on how the last couple of years have been "wicked" due to the rapid changes in technology and the industry's shift towards inno...

In this episode of Insurance Town, the Mayor, Heath Shearon welcomes Jamie Peers  really just to catch up and have a chat, but this lead to hitting the record button, and discussing the evolving landscape of the insurance industry, focusing on data integration, AI, and the challenges of maintaining clean data. Jamie shares insights from his journey through startups and consulting, emphasizing the importance of introspe...

In this weeks episode, the Mayor and Toby discuss the intersection of technology and insurance, focusing on the challenges and opportunities within the industry. They explore the role of AI in transforming insurance processes, the importance of understanding client needs, and the potential for technology to attract new talent to the field. Toby shares insights from his journey in the insurance and tech sectors, highlig...

In this week's episode the Mayor Heath Shearon hosts another town hall meeting. This week we talk about the headaches of intake forms and gathering of prospect information, And the back and forth of gathering pertinent information for underwriters. All of these things can end up being a roadblock. All of these things can sometimes caused bottlenecks in your agency. That is where Canopy Connect comes into play with their in...

In this weeks episode of Insurance Town, The Mayor Heath Shearon, sits down with Valerie Bowden, founder of Crdle, to discuss the evolving landscape of outsourcing and the unique opportunities Africa presents. Valerie shares her journey from backpacking across Africa to establishing a successful outsourcing company that champions fair wages and ethical practices. Discover how Crdle is changing the game by connecting busine...

In this episode, Mayor Heath Shearon, sits down with Thomas Mann to explore the intersection of technology and operations in the insurance industry. Discover how Thomas's journey from a multi-generational insurance background to a tech-focused role has shaped his approach to agency success. They discuss the importance of integrating technology with operations, avoiding common pitfalls, and the value of involving your team ...

In this weeks episode, you are simply eavesdropping in on a fun conversation with me and two of my faves, Lindsay Wallace & Caleb Cramer . It is part goofy, and part serious but it’s all heart and it’s all fun trying out a new format here on this one and I’d love to hear your thoughts.

I am so incredibly lucky I get to do this show every week. It makes me completely happy and it couldn’t be done without you. Thank you f...

In this Episode Our Mayor, Heath Shearon as he sits down with Hari Srinivasan to explore the fascinating world of life insurance. From cricket to Cardinals, and from tech to insurance, Hari shares his journey and insights into making life insurance accessible and meaningful. Discover how iCover is revolutionizing the industry with its innovative platform and community-focused approach. Hari shows us the importance of p...

This week  Heath Shearon, the Mayor of Insurance Town,  sits down with his good friend Craig Bender, the visionary behind InsureU2. In this episode, Craig shares his journey from a  big player in the paintball community as a young "kid" to a leader in the insurance industry. Discover how his unique approach to marketing and community building is reshaping the way insurance is perceived and practiced. Craig discusses the im...

Episode Summary: Join us for an insightful conversation with Draye Redfern, a marketing expert with a rich background in insurance and a knack for innovative strategies. Draye shares his journey from working in his family's insurance agency to founding Redfern Media, a marketing agency that has helped numerous businesses thrive. Discover the power of direct mail, the importance of knowing your numbers, and the value of...

In this Episode of Insurance Town, The Mayor Himself sits down and shares his experiences from IB FutureFest 2025, He shares his exhilarating experience at Future Fest, an innovative insurance festival held on the Santa Monica Pier. Discover the unique atmosphere, engaging activities, and insightful sessions that set this event apart from traditional conferences.

Festival Vibes: Future Fest's outdoor setting on the Santa Mo...

 Join us as we dive into an insightful conversation with Peter Flynn, who leads the personal lines vertical in the Americas for Exceedance. Discover his journey from an underwriting trainee at Chubb to his current role, and learn about the innovative ways Exceedance is transforming the insurance industry.

Peter's career path and experiences in the insurance industry The role of Exceedance in operationalizing insuran...

n this week’s visit to Insurance Town, I had the pleasure of sitting down with Spencer Witcher, a second-generation insurance pro who’s doing big things with Smart Choice. We had a real talk about the challenges agents face in hard-to-place markets — and how finding the right partners can make all the difference.

We peeled back the curtain on:

• What Smart Choice is doing to help agents thrive in California and other tough...

Think ChatGPT is just for writing emails? Think again. In this episode, Chris Green drops real-world prompts and jaw-dropping use cases that will make you rethink how you engage every prospect and client.

Is AI just another shiny object… or the secret weapon your agency has been missing?

In this high-energy episode of Insurance Town, the Flood Guru himself, Chris Green, steps into the Mayor’s office and throws down examp...

In this epsisode of Insurance Town the mayor sits down with two of his favorite people Jessica Holder and Keenan Rice on a previously recorded episode of the VIP Podcast. I am so impressed with these two, their marriage, parenting, agency, etc  this forward-thinking power couple are continuing to rise above and face various challenges head on. Jessica and Keenan have such an amazing balance at home and at the office. They ...

In this episode of Insurance Town, host and Mayor, Heath engages with Allen Hudson at the PIA Virginia DC Conference. They discuss the critical importance of information sharing in the insurance industry, especially for independent agents. The conversation highlights the role of technology, particularly AI, in enhancing efficiency and specialization within agencies. Allen shares insights on the resurgence of independent ag...