Insurance Town

This week in Insurance Town, I got to sit down with Francisco Lopes of Sonant.AI for a conversation about one of the fastest-growing technologies in the insurance industry: voice AI.

Artificial intelligence has become one of the biggest topics in our business, but with all the excitement comes plenty of skepticism. Francisco and I discussed where voice AI has come from, why today's technology is dramatically different than the autom...

There are some interviews you enjoy... and then there are conversations you genuinely don't want to end. This was one of those.

Recorded live from the iconic Santa Monica Pier during InsuranceFest 2026, I had the opportunity to sit down with Christina Lucas of Google Cloud, and what a fantastic conversation it turned out to be.

While many people know Christina for her work at Google Cloud, what really stood out was her incredible jou...

In this weeks episode i interview my new friend Jerry Ye, we explore how AI is transforming the insurance industry through the lens of Jerry Ye, in this engaging episode. Learn about the practical applications of AI in streamlining workflows, enhancing client relationships, and the future agency model.

• The journey of Jerry Ye into the insurance and AI space, including his background in machine learning and entrepreneurship
• How AI...

In this weeks episde here in Insurance Town I got to interview my friend Jackson Rollo. In this episode Jackson, president of Rollo Insurance Group, shares how a second-generation family agency achieved remarkable growth by embracing unorthodox strategies rooted in community focus, technological innovation, and strong culture. Discover how intentional investment in people and purpose can transform an agency into a leading industry ...

In this episode of Insurance Town, we've got a Mayor Solo episode. No guest this week, just me and my fellow citizens of Insurance Town.

Today, we're tackling a topic that I think has become way more complicated than it needs to be: personal branding.

I'm going to challenge some of the biggest buzzwords in business and marketing today. What if "personal branding" is really just your reputation? What if authenticity is simply being tr...

Most insurance agencies are still using AI like a search engine.

They open ChatGPT.
 They ask a question.
 They get an answer.

That’s useful.

But it’s also reactive.

The next generation of AI doesn’t wait to be told what to do.

It monitors activity, organizes information, surfaces opportunities, flags missing data, drafts communications, and helps move work forward before anyone even asks.

That’s t...

In this week’s episode of Insurance Town, I had the privilege of sitting down with my good friend Kelly Smith.

Kelly is one of those people who has truly lived the insurance industry from every angle. She grew up in a family agency, spent time at the front desk, worked in personal lines, commercial lines, agency operations, underwriting, carrier sales, and now helps independent agencies grow through her work with FirstChoice.

W...

In this week's episode of Insurance Town Podcast, I sat down with my good friend Mariah Gates. Mariah has become one of the insurance industry's leading voices on automation, technology adoption, and helping agencies work smarter. What makes her perspective unique is that it is grounded in service, faith, and a genuine desire to help others succeed.

During our conversation, we discussed how agencies can stop viewing technology as a ...

In this week's episode of the Insurance Town Podcast, I got to sit down with my good friend Carl Ziade, co-founder of Gaia, for a conversation about innovation, entrepreneurship, AI, and what it really takes to drive meaningful change inside an insurance agency.

One of the things I appreciate most about Carl is that while he's a technologist at heart, he understands that technology alone doesn't solve problems. Process comes first. ...

In today’s episode of Insurance Town, Heath sits down with Paul Riemer, CEO of Riemer Insurance Group and Panther Insurance. Paul shares how his agency has grown through a commitment to relationships, community involvement, strategic niche markets, and a willingness to embrace innovation while maintaining a personal touch.

As a second-generation insurance professional, Paul discusses the lessons learned from starting at the gr...

In this episode of Insurance Town, I get to interview my good friend Casey Armstrong of Canopy Connect. We dive into the innovative ways Canopy Connect is revolutionizing data collection for insurance agencies. Casey shares insights on how their platform simplifies client interactions, enhances data accuracy, and integrates seamlessly into existing workflows. Join us for an engaging discussion on the future of insurance technology ...

In this week’s episode of Insurance Town, I had the privilege of interviewing my friend Ema Roloff of Roloff Consulting. Ema and I dive deep into what it really means to lead in today’s digital world, especially in an industry built on relationships, trust, and communication.

Ema shares her journey from education into digital sales and consulting, along with the lessons she learned during the COVID era that completely tr...

In this episode, Jay Wolfberg shares his remarkable journey from a small Connecticut town to leading a $32 million agency in Florida, and discusses his insights on scaling, client relationships, and franchise models in the insurance industry. Whether you're an aspiring agent or an industry veteran, Jay’s strategic approach to responsiveness and authenticity offers valuable lessons for growth and success.

Timestamps

00:00 - Intr...

In this episode, Tyler Brown shares a grounded and practical look at what actually drives success in insurance sales. Drawing from his upbringing and career journey, Tyler explains why authentic listening is still the most underrated skill in the business. He breaks down how emotional connection influences buying decisions, how to ask better questions, and why consistent follow-up separates top producers from everyone else.

The conv...

In this episode of Insurance Town, Kevin Deutsch joins the show to unpack what’s really happening in the health insurance space right now. From the growing role of AI to the emergence of ICHRA as a disruptive model, Kevin brings a practical perspective on where the industry is headed and what it means for agents, brokers, and agencies.

The conversation digs into how technology is reshaping distribution, why data management is ...

This Week In Insurance Town, we uncover practical insights and inspiring stories with Chelsea Bell Carpenter as she shares her journey through the insurance industry, mental health strategies, and the importance of intentional living to combat burnout. This conversation empowers listeners to redefine success, build confidence, and prioritize well-being amidst today's fast-paced world.

• Chelsea's diverse insurance career and lesso...

 In this episode, Jason Peacock shares invaluable insights from his nearly three-decade career in insurance, emphasizing the importance of relationships, niching, and strategic follow-up. Whether you're just starting out or a seasoned pro, you'll find practical tips on building lasting client and carrier partnerships, navigating industry changes, and avoiding common pitfalls.

Key Topics:

•  The evolution of industry techn...

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 businesses with...