Insurance Town

This episode is live from the Santa Monica Peir at Insurance Fest 2026. Sponsors:Canopy Connect -Making it easier for agencies to collect insurance information directly from clients and prospects, helping speed up the quoting process and improve the customer experience.Bind AI-  An AI-powered digital teammate built to help insurance professionals automate repetitive work, increase efficiency, and give their teams more time to focus on the human side of the business. V!VA-  Helping insurance agencies scale with trained virtual professionals who can support service, operations, marketing, and more giving your team add...

This week in Insurance Town, Mayor sits down with longtime friend and fellow insurance leader Heath Barnett, co-owner of Legacy, for a conversation about growth, culture, ownership, and building a business people actually want to be part of.Heath Barnett is an insurance agency leader and co-owner of Legacy. After beginning his career in the captive insurance world, Heath transitioned into the independent channel and helped build Legacy into a multi-state insurance organization.His leadership philosophy centers on developing people, creating opportunities for ownership, giving local leaders autonomy, and building an organization where professional success...

in this weeks episode, Heath Shearon sits down with Rob Lopez, CEO of V!VA, for a wide-ranging conversation about insurance, outsourcing, virtual assistants, and AI. Rob shares how his path from broadcast journalism and sports radio led him back into the insurance world, and why his focus has always been on building real departments not just filling seats.They also dig into what makes V!VA different: process-driven onboarding, bilingual support, nearshore staffing in El Salvador, and a consultative approach that helps agencies document workflows before adding talent.https://vivateams.com/insurancetown<...

In this weeks episode the Mayor talks with Dave Rose, an agency operator at Bolt and former Liberty Mutual and Travelers leader, about what independent agents can learn from captive carriers, how connected distribution works, and how agencies can start using AI without overhauling everything. Dave brings a practical, operator’s perspective from both the agency side and the tech side, with a focus on real-world implementation rather than hype.In this episode, they cover the process discipline of captive agencies, the power of referrals and centers of influence in the independent channel, and why AI adoption is more ab...

This week in insurance town Heath Shearon sits down with Martin Mashalov, co-founder of Gridpull, to unpack why buying more leads is not the same as getting more business. They dig into how appetite matching, renewal timing, and trigger-based prospecting can help agencies spend producer time more efficiently and improve conversion rates.Martin explains how his background in applied math and insurance analytics led him to build tools for finding better prospects, not just more prospects. The conversation stays practical throughout, with examples from restaurants, commercial real estate, and new business triggers.00:00 - Welcome...

This week Drake Lawhead comes to visit us in Insurance Town to talk all things conference , and maximizing the conference experience. We get into what all goes into building a major industry event and how attendees can actually get value from showing up. They also dig into how ITC evolved from an investor-focused conference into a broader experience for agents, brokers, carriers, and the tech vendors serving them.We discuss why in-person networking still matters, how to prepare before a conference, and what makes ITC’s agent and broker programming different from a typical trade show. 0...

In this weeks Episode, I got the chance to talk to my brother, my homie, my main man, Casey Nelson of Agency X and Eclipse Insurance. We talked about a major career shift, returning to the agency side with Eclipse Insurance, and why that move is giving him a new lens on what  works and what doesnt inside an agency. They also dig into Agency X, Casey and Jessica Holder’s upcoming behind the scenes podcast about fixing real agency problems in real time. Think, Reality TV meets VLog, meets Podcast, and all rolled into some entertaining and Educational Con...

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 automated phone systems of the past, and how agencies can begin using AI in ways that improve both customer experience and operational efficiency.We also...

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 journey. From leading teams across the United States to living and working around the world, her experiences have shaped a unique perspective...

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 entrepreneurshipHow AI is helping agencies automate manual tasks like policy checks, renewals, and COI generationThe importance of integrating AI deeply into agency workflows versus superficial useThe myths and realities of A...

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 force.Main Topics Covered: The evolution and rapid growth of Rollo Insurance over the past five years, doubling its offices despite a 26-year historyThe agency’s dedication to community involvement, including vol...

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 true to yourself? What if networking is nothing more than making genuine friends?As a 90's kid, I...

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 the difference between using AI as a tool and working alongside an AI Digital Teammate.In this episo...

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.What I loved about this conversation is that Kelly’s story is not just about insurance. It is about curiosity, hard work, education, fami...

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 burden and start seeing it as a strategic advantage. Mariah shares practical advice for building an effective technology ecosystem, implementing AI without overwhelming your team, and creating...

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. People come first. Technology simply helps great organizations execute better.Carl's journey is a fascinating one. As a Lebanese immigrant and Stanford-trained computer scientist...

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 ground level, building trust with clients, developing strong teams, and navigating today’s rapidly changing insurance marketplace.Key Topics Discussed:• Building a successful agency through relationships and community engagement• Op...

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 and how agencies can leverage these tools for growth and efficiency..In this episode: Casey shares his journey with Canopy Connect from its inception in 2020 and how agency data collection has e...

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 transformed the way she approached content, technology, and leadership. This conversation is packed with practical insights for insurance professionals, business owners, marketers, and anyone trying to navi...

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.Timestamps00:00 - Introduction and episode overview 02:24 - Meeting Jay Wolfberg and intro06:17 - The importance of selling on value versus price09:02 - How Jay figured out his agency’s uniqu...