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Insurance Town

Heath Shearon·330 episodes

BusinessEducationHow ToInsurance industryExpert interviewsAgency growthSales strategyWeeklyCasual business talk

Welcome to Insurance Town! Your host is the Mayor of Insurance Town, Heath Shearon. After many years in different parts of the insurance world, Heath wants to share his experience with you. Join in on conversations with Heath and many of the friends he's made along the way. Insurance Town is a production of Insurance Town LLC! Find more info at http/://www.Insurancetownpodcast.com Music: "Mornin, Noon, and Nite" by Daddy Long Legs

Why listen

Insurance Town gives insurance professionals a friendly, practical seat at the table with host Heath Shearon, who frames the show as conversations with people from across the industry. Episodes mix sales advice, agency operations, insurance technology, leadership, mental health, and relationship-building, usually through relaxed interviews with agents, consultants, founders, and carrier-side voices. It is especially useful for independent agents, producers, agency owners, and insurance vendors who want field-tested ideas without a stiff corporate feel.

Episodes

47 min
Jun 4, 2026Episode 334
What Separates This Growing Agency from Everyone Else?

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• Opportunities emerging in challenging insurance markets• Growing through niche markets and specialized expertise• Creating a culture that attracts and retains great people• Balancing technology, AI, and personal service• Lessons learned from a family-owned insurance businessEpisode TimelineIntroduction & Sponsors (0:01 - 1:57)Paul’s Introduction & Market Insights (2:19 - 4:13)Personal Background & Family Business (6:04 - 8:01)Challenges & Learning in Insurance (9:33 - 13:02)Agency Growth & Team Dynamics (13:52 - 15:21)Community Engagement & Relationship Building (19:29 - 20:57)Innovation & Maintaining the Personal Touch (43:00 - 44:28)Conclusion & Contact Information (47:43 - 49:35)Thanks to our Sponsors:1fort AICanopy ConnectMavThe Sassy Happy

44 min
May 28, 2026Episode 333
How Is AI Transforming Insurance with Data Accuracy and Efficiency

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 evolved.The simplicity of using QR codes and custom referral links to streamline prospect interactions.How Canopy Connect’s Trailhead feature offers flexible, choose-your-own-adventure insurance pathways.The real-world impact of instant loss runs and deck pages extracted directly from carriers’ systems.The role of AI in automating mundane tasks, freeing agents to focus on trusted advisory.Unique marketing strategies like limo rides and conference appearances to connect with customers creatively.The importance of human oversight in AI solutions to ensure accuracy and trust.Case stories illustrating premium increases through correct coverage and client advocacy.Practical tips for agencies new to Canopy Connect, including the ease of integrating it into current workflows.Casey’s heartfelt message on gratitude, technological progress, and the future of insurance. Timestamps: 00:00 - Welcome to Insurance Town & Casey Armstrong intro 00:29 - Canopy Connect: The one-click solution for agencies 00:58 - The benefits of automation and the Trailhead feature 01:26 - AI for insurance: saving time and improving accuracy 02:23 - Exploring innovative marketing strategies and conference fun 03:00 - Casey’s background, biking stories, and Northwest Arkansas 07:28 - How Canopy Connect transforms prospect engagement 08:08 - The value of instant carrier data and loss runs 09:39 - Bringing human oversight to AI automation 10:34 - The manual effort saved by AI and data accuracy 12:23 - How deck pages from carriers eliminate errors 15:08 - Commercial accounts insights and loss history access 16:13 - Simplified onboarding for new users of Canopy Connect 16:53 - Embedding Canopy into existing agency workflows 20:16 - Real-world client stories: under-insured homes & premium impacts 24:28 - Trailhead: The flexible, customizable journey paths 28:23 - The speed and efficiency benefits of Canopy Connect 30:34 - Lead tracking and prospect management dashboard 36:37 - Creative marketing: conference limos & branded experiences 38:35 - Heartfelt messages to existing customers and prospects 42:08 - Casey’s call to action: har

1 hr 3 min
May 21, 2026Episode 332
How can I use Content to Build Relationships and Grow my book?

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 navigate change without losing authenticity along the way.We talk about the power of educational content, why relationship-building still wins, how to use AI intentionally, and what it means to become a true digital leader inside your organization.If you’ve ever struggled with showing up online, wondered how to balance authenticity with innovation, or felt overwhelmed by the pace of change in business today, this episode is for you.Timestamps 00:00 – Introduction and episode overview  07:25 – Overcoming sales challenges through content and education  09:33 – Why relationship-building beats traditional sales tactics  11:45 – Long-term trust development and sales cycles  13:09 – Creating authentic, value-driven content for B2B success  22:06 – Change management and decision fatigue  24:24 – Moving from product-focused to problem-focused content  26:55 – The mindset of serving and educating through social media  31:36 – Balancing authenticity with experimentation and technology  36:31 – Intentional implementation of AI and tech solutions  46:33 – Avoiding hype cycles and focusing on purposeful growth  54:32 – Reflecting on COVID as a catalyst for growth and innovation  59:10 – Ema’s current work and how to connect with her And as always, thank you to our amazing sponsors: Canopy Connect  MAV  1Fort AI Be sure to subscribe, leave a review, and share this episode with someone in the insurance industry who could benefit from the conversation.--------------------------------------------------------

41 min
May 14, 2026Episode 331
How Does Hyper-Responsiveness Set Top Insurance Agencies Apart?

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 unique value proposition 11:37 - Handling commoditized auto coverage and understanding customer needs & growth y to a $32 million book14:40 - The secret to hyper-responsiveness and proactive customer service 18:48 - Creating an effortless, customer-centric experience 22:41 - Building and leading a franchise with WeInsure 37:21 - The structure and benefits of the WeInsure39:00- how to find JAY1Fort: AI for insurance agencies, automating submissions, quoting, and binding to save time and win more commercial PNC.Canopy Connect: The one-click solution for getting deck pages needed to quote prospects.MAV: AI-powered insurance expert managing unlimited leads with friendly text to qualify, quote, and connect prospects to agents.Resources & LinksWeInsure GroupJay Wolfberg’s emailConnect with Jay WolfbergLinkedInTwitter

33 min
May 1, 2026Episode 330
Am I Listening Enough to Close More Deals?

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 conversation also explores how tools like AI, including platforms like Nova Intel, can sharpen sales performance without replacing the human element. If you are looking to improve close rates, build stronger client relationships, and bring more intention into your sales process, this episode offers a straightforward roadmap.A quick thank you to our sponsors who make conversations like this possible: 1Fort, Canopy Connect, and MAV.What You’ll Learn: Why listening is more powerful than pitching in today’s sales environment  How emotional triggers influence buying decisions  Practical ways to improve your follow-up process  The art of asking deeper, more meaningful questions  How AI can support, not replace, strong sales habits  Why trust is built through honesty and transparency, not pressure Key Takeaways:Tyler makes a strong case that most sales problems are not pipeline problems, they are communication problems. Agents often talk too much, assume too much, and follow up too little.One of the biggest shifts discussed is moving from surface-level conversations to deeper discovery. When you slow down and truly understand what matters to a client, your recommendations become more relevant and your close rate improves naturally.Another important theme is consistency. Follow-up is not complicated, but it does require discipline. The agents who win are the ones who stay in front of prospects in a thoughtful and helpful way.On the technology side, AI is positioned as a tool for refinement. Whether it is helping analyze conversations, suggest better questions, or improve messaging, it gives agents an edge if they are willing to use it.Notable Quotes: “If you listen long enough, people will tell you exactly how to sell to them.”  “People don’t buy policies, they buy peace of mind.”  “Follow-up isn’t about being pushy, it’s about being present.” Canopy Connect If you’re still chasing down dec pages and playing email tag with clients, you need to check out Canopy Connect. It’s a simple tool that lets your clients securely share their current insurance information in minutes. That means faster quoting, cleaner data, and a much better client experience. It takes friction out of the process, which i

56 min
Apr 23, 2026Episode 329
How can you capitalize on this shift to personalized Health Insurance?

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 becoming a competitive advantage, and how personalization is moving from buzzword to reality. If you’ve ever felt like health insurance is overly complex, this episode helps simplify what matters and where to focus.Key Takeaways: Health insurance remains overly complex, but simplification is coming through better technology and data use  AI is only as effective as the data behind it, making data organization critical for agencies  ICHRA is creating new opportunities and challenges for brokers in the benefits space  Commission structures and distribution models are continuing to evolve  Personalization is not a future idea, it is actively shaping how coverage is designed and delivered today  Agencies that understand and adapt to these shifts will be better positioned for long-term growth  00:00 – Introduction 09:02 – Changes in Health Insurance Distribution 12:05 – The Role of Brokers in Health Insurance 15:06 – The Shift in Commission Structures 18:10 – The Impact of ICRA on Health Insurance 24:10 – Future of P&C Agencies in Health Insurance 29:57 – Understanding ICRA and Its Value 32:29 – Adoption of AI in Health Insurance 38:05 – Data Management for AI Utilization 40:26 – Trends in Personalization of Health Insurance 43:21 – Preparing for Personalized Benefits 44:42 – The Rise of Provider Sponsored Health Plans  48:59 – Softheon Mission and ServicesSponsorsCanopy ConnectMav1Fort AI Goli

22 min
Apr 16, 2026Episode 328
Lazy River Files Part 3

In this weeks episode we release more from the Lazy River, Casey Nelson's idea that has been such an amazing addition to the show. I appreciate all of the feedback I have gotten from these, so I will leak a few more out over time!  This clip is a continuation of the part 2, where we get into mental health, and leadership principles etc. sponsored by:Canopy ConnectMAV1Fort AI

59 min
Apr 9, 2026Episode 327
How do I know if I am burned out or just stressed out?

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 lessons learnedRecognizing and managing burnout in a hyper-connected societyStrategies for building confidence and resilienceThe importance of boundaries, alone time, and intentional activities Generational shifts in attitudes toward work, health, and life balance Practical tools to reconnect with yourself and reduce stress In this episode You will also hear...  Chelsea's unexpected journey from insurance rookie to industry leaderHow wildfires and claims transformed her understanding of service and empathyThe true definition of burnout and how to identify its symptomsWhy organizations play a role in employee burnout and how individuals can take controlSimple somatic tools to calm your nervous system during stressful momentsThe cultural shift away from "busy as a badge of honor" toward conscious livingTips for carving out quality family time and developing passions outside of workAddressing fears of AI and automation: embracing technology as an allyThe importance of vulnerability and authentic leadership Timestamps00:00 - Welcome to the episode and introduction of Chelsea Bell Carpenter 06:29 - Wildfires, service, and the human side of insurance claims 16:22 - Developing confidence and overcoming fear of failure 21:59 - Managing stress responses in our technology-driven world 24:29 - Building stronger family and personal boundaries 26:42 - The impact of social media and constant connectivity 34:52 - How to distinguish between stress and burnout 37:14 - Strategies for organization, work-life balance, and hobbies 42:13 - The power of solitude and true rest in a busy society 46:42 - Addressing generational differences and future outlooks on burnout 53:33 - Organizational vs individual responsibility for burnout 55:57 - How to work with Chelsea for consulting, speaking, or events Chelsea Bell Carpenter — Connect and explore coaching and speaking servicesChelseaBellCarpenter.com — Website for programs and contactDerek Streep's Comedic Bit — Humorous take on taking breaks Connect with Chelsea<a href="https://www

54 min
Apr 2, 2026Episode 326
What Are the Secrets to Long-Term Success in Insurance?

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 technology from paper directories to AI-powered tools The critical role of relationship-building with carriers and clients for long-term success How niching in specific industries can accelerate growth and simplify prospecting The importance of response time and follow-up in maintaining client trust Strategies to identify ideal clients and develop a targeted marketing approach The value of maintaining a well-structured system to prevent deals from falling through the cracks Lessons learned from setbacks, including the importance of asking tough questions early How to leverage existing relationships and reputation to find repeat business The significance of saying “no” to class types or clients that don’t align with your goals Practical advice for new producers and agency owners to accelerate their learning curve Timestamps:  02:08 - Industry changes: from directories to digital 07:23 - The evolution of email and accessibility in insurance 12:00 - The irreplaceable value of personal client interactions 13:12 - Building and maintaining strong carrier relationships 15:36 - The importance of niching 27:36 - Niching and client profile optimization 30:41 - After securing clients: how to maintain and expand relationships 35:30 - Going where your best clients are and leveraging environments 40:30 - Systems to prevent follow-up failures and keep deals alive 45:17 - Handling clients outside your niche and collaborative referral networks 50:00 - Mentoring young producers and industry training 53:56 - Closing remarks and appreciation for industry peers SponsorsCanopy Connect Goli Nutrition MAV Insurance AI Connect with Jason Peacock: Website: JasonCPeacock.com LinkedIn: Jason Peacock Twitter: @JasonCPeacock Note: This episode is packed with actionable insights that cut through industry noise—great for agents, carrier reps, and aspiring producers alike.

54 min
Mar 26, 2026Episode 325
Choose Africa - Re-Visit

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 talented professionals from the continent. Introduction[03:15] Valerie's JourneyValerie shares her adventurous backpacking trip across Africa How her experiences led to the founding of Cradle[10:45] The Cradle MissionDiscussion on ethical outsourcing and creating sustainable jobs The importance of fair wages and supporting African talent[18:30] Bridging the GapHow Cradle connects African professionals with global businesses Success stories and client experiences[25:00] The Role of AIValerie's insights on AI's impact on virtual assistants How AI tools enhance the capabilities of offshore teams[32:15] Tips for Hiring Offshore TalentValerie's advice for businesses looking to hire from Africa Best practices for onboarding and training virtual assistants[40:00] Closing ThoughtsValerie's vision for the future of outsourcing Final words and how to connect with Valerie and CradleSponsors:Canopy Connect: Revolutionizing the way agencies handle client data with their innovative intake form platform. Learn more at usecanopy.com.MAV- Ditch the call center and Hire Mav. Goli- GoGoli.com/MayorWant to work with Crdle ?want to contact Valerie Bowden

42 min
Mar 19, 2026Episode 324
Are You Truly Connecting with Your Clients or Just Talking at Them?

You know that room in grandmas house that was that room that you didn’t sit in the furniture, you didnt touch anything? It was just pretty and you gotten threatened every time you went into that room?In this weeks episode, Monica Adwani, CPIA and I talk about that, and tie it into something that makes us cringe in the insurance industry. She also shares her extensive journey through the insurance industry, her insights on client communication, the importance of relationship-building, and how leveraging data and technology can transform agency operations. Discover practical tips on serving diverse communities, embracing AI, and enhancing efficiency to grow your insurance business.We discuss role of client education in building long-term trust. Monica breaks down how taking the time to truly educate clients not only strengthens retention, but positions you as a true advisor, not just a policy seller.And of course, we laugh a lot , we talk about our teenagers , life , Karate, and all kinds of other random topics too!!00:00 Reunion and Reflections03:01 Monica's Journey in Insurance06:01 Understanding the Carrier Perspective08:59 The Importance of Insurance Education12:08 Cultural Sensitivity in Insurance14:58 Effective Communication Strategies18:03 Adapting to Generational Differences18:37 Generational Communication Shifts21:49 Building Trust in Client Relationships24:38 The Role of Agents in a Digital Age27:50 Operational Efficiency in Agencies31:41 Time as the New Currency35:00 Leveraging AI for Better Decision MakingJump in and check it out Sponsored by:Canopy Connect Mav Goli Nutrition

34 min
Mar 12, 2026Episode 323
Are You Ready to Enhance Your Agency's Cybersecurity and Tech Efficiency?

In this episode, Lamar Garrett from Redbird Security delves into the critical importance of agency-specific cybersecurity tailored for insurance businesses. He discusses how proactive hardware and software maintenance can significantly reduce downtime, while the integration of AI streamlines operations and enhances security protocols. Lamar highlights the differences between general IT providers and insurance-specific MSPs, emphasizing the need for compliance with state and federal data regulations. He also shares best practices for integrating new technology, managing shiny objects, and preventing breaches through layered security and cyber awareness training. Additionally, Lamar addresses the impact of legacy hardware on security vulnerabilities and the importance of building strong relationships and trust within the insurance industry, along with strategies to improve communication about cybersecurity to agency owners.Lamar emphasizes that tailored cybersecurity, proactive hardware management, and clear communication are crucial for insurance agencies to protect their data and scale efficiently. His insights highlight that investing in industry-specific IT solutions is not just smart but necessary in today’s digital landscape.Timestamps:00:00 - Introduction to Lamar Garrett and Redbird Security06:25 - The importance of insurance-specific IT solutions08:41 - How cybersecurity breaches impact large organizations and why agencies are at risk12:48 - Common misconceptions about insurance cybersecurity needs16:41 - Optimizing agency tech stacks for efficiency and compliance24:23 - Response times and minimizing downtime for agency management systems28:40 - How AI is transforming insurance IT security and operations32:38 - The hidden costs of aging hardware and legacy systems37:40 - Final thoughts on securing agency data and building industry trustResources & Links:Redbird SecurityRedbird Security on LinkedInApplied Epic MSP PartnershipMicrosoft CopilotEZLinks SoftwareCybersecurity Awareness CartoonsBook: "The Art of Cybersecurity" by David S. TanenbaumConnect with Lamar Garrett:LinkedIn - Lamar GarrettRedbird SecuritySponsors:MavCanopy ConnectGOLI

36 min
Mar 5, 2026Episode 322
More from the Lazy River Files

It's another episiode of Insurance town from the Lazy river!! With Ben Morrow, Brenden Corr, Marques Ogden, Jessica, Casey Nelson, Caleb Cramer, etc. Its FunSponsorsCanopy Connect MAVGoli= Go.Goli.com/Mayor

46 min
Feb 26, 2026Episode 321
How to stop being overlooked! (warning this one is High Octane)

In this episode of Insurance Town, the Mayor sits down with his good friend, Emily Merola. Emily Merola is an executive presence expert, speaker, and founder of The Blazer Society who helps leaders go from overlooked to unmistakable. Through her work in Image + Impact and identity-first leadership, Emily equips leaders to bridge the gap between who they are and how they lead so they communicate with clarity, step into alignment, and own every room they enter. With more than 20 years of executive leadership experience and as a Maxwell Leadership Certified Speaker, Trainer, and Coach, Emily has influenced over 10,000 professionals worldwide through keynotes, retreats, and global leadership forums. She is trusted by organizations and event leaders to open and close high-stakes conversations, and is known for delivering high-energy, high-impact experiences that blend strategic insight with powerful personal transformation. She joins us to day and shares her inspiring journey from the early days of her insurance career to becoming a trusted leader and coach. We explore the importance of authenticity, self-awareness, and faith in building genuine relationships and impactful careers.In this episode:Emily's beginnings in New York City insurance and her rapid rise through different sectorsThe power of self-awareness in discovering your strength zoneHow authenticity and vulnerability foster real relationshipsNavigating confidence challenges and stage frightThe role of faith and core values in decision-makingBuilding a leadership brand that empowers women through The Blazer SocietyThe significance of having a coach and mentors (including John Maxwell) for growthStrategies for overcoming feeling overlooked or stuck in your careerHow inner work and community create resilience in uncertain marketsTimestamps: 00:00 - Welcome and introduction to Emily Morolla 02:08 - Emily’s professional background and journey into insurance 04:33 - Early lessons from the insurance industry and career milestones  10:31 - The through line: Trust and relationship-building in insurance 12:20 - Balancing confidence, vulnerability, and industry norms 16:46 - Seasons in career and embracing change 122:28 - Faith as a guiding force in personal and professional life 25:33 - Authentic relationships and maintaining consistency 28:46 - Introducing The Blazer Society and empowering women leaders The motivation behind creating a space for growth and impact 33:21 - The power of personalized branding and leadership identity 36:57 - Overcoming stage fright and building presentation confidence  Resilience, storytelling, and embracing vulnerability 43:20 - Practical steps for those feeling stuck or overlooked and importance of coaching, environment, and community 45:32 - Final reflections and gratit

53 min
Feb 19, 2026Episode 320
From SEO to GEO: Navigating the Marketing and Search optimization game!

The Future of AI in Marketing & Insurance: Insights with Cameron LaboudiIn this week's episode, the Mayor Heath Shearon sits down with Cameron LiButti of BidView Marketing. These two dive into the transformative power of artificial intelligence in reshaping marketing strategies and customer engagement, particularly within the insurance industry. They explore practical advice and emerging trends, offering listeners insights on how to adapt and thrive in this rapidly evolving landscape. Explore how artificial intelligence is transforming marketing strategies, SEO, and customer engagement, especially within the insurance industry. Cameron Libutti shares practical advice, emerging trends, and how professionals can adapt to this rapidly evolving landscape.Key TopicsThe evolving role of AI commercials in Super Bowl marketing and industry impactsHow AI platforms like ChatGPT, Claude, and Gemini are changing search behaviorsThe importance of local community positioning over broad claimsDifferentiating your business through brand imagery and reviewsThe shift from traditional SEO to AI-focused citations and content strategiesTactical tips for small agencies on landing pages and content structureHow interest graph algorithms influence short-form and long-form contentThe emerging concept of GEO (Generative Engine Optimization) and AI rankingsPractical steps for professionals to optimize their presence in AI-driven searchesThe power of AI in rapid prototyping and business data intelligenceTimestamps00:00 - Welcome and episode overview: AI's impact on marketing and insurance 07:11 - Cameron’s journey from engineering to marketing and digital strategy 12:22 - The importance of local community positioning in professional services 14:36 - Creative outreach ideas: giving away cookies to nurture leads 17:13 - How to position yourself as the best in your local market 18:04 - Using imagery and reviews to build trust and credibility 21:24 - The relevance of SEO in an AI-powered search landscape 22:51 - The disruptive influence of generative AI like ChatGPT on traditional search 26:11 - Tracking AI-driven leads and measuring success 28:22 - How local agencies can succeed with traditional SEO 35:41 - Navigating social media algorithms: long vs. short-form content 39:20 - Introduction to GEO: Generative AI engine optimization 40:11 - Understanding AI rankings and data personalization 42:31 - Practical steps for agencies to improve AI visibility  44:45 - Citation strategies across platforms and directories  48:25 - Cameron’s AI soapbox: Power, capability, and rapid development in AI tools  53:11 - Closing remarks and contact info for Cameron LibuttiSponsors:Smart Choice Agency Network<a href="https://us

49 min
Feb 12, 2026Episode 319
The “hold my beer” of insurance !

This week in Insurance town the Mayor sits down with  Sarah Koolhof, a dynamic insurance professional whose journey spans theater, rugby, and underwriting. Discover how embracing discomfort and versatility has shaped her career and passion for relationship-driven insurance work. She has been with Commonwealth Undewriters for a dozen years and not going anywhere any time soon, She loves her team and her clients. I loved this conversation and I think you will too.In this episode:Sarah's unexpected transition from theater major to insurance underwriterHow rugby taught her resilience and the value of teamworkThe importance of building trust in E&S and surplus lines marketsNavigating industry changes over 12 years, especially in ENSStrategies for agency and carrier partnerships rooted in responsivenessInsights on managing industry burnout and maintaining mental healthPractical tips for agents choosing E&S brokers and understanding underwriting authorityThe culture of collaboration and relationship building at Commonwealth UnderwritersTimestamps:00:00 - Welcome and episode overview00:30 - Sarah's background: from theater to insurance02:00 - The role of rugby in building resilience and confidence04:30 - How her diverse experiences shape her industry perspective08:00 - Navigating industry changes and the evolution of E&S markets12:00 - Building trust in surplus lines and the importance of partnerships16:00 - Commonwealth Underwriters: location, services, and company culture20:00 - Response times, setting expectations, and fostering client relationships24:00 - Managing industry burnout and mental health awareness28:00 - Tips for agents on selecting E&S brokers and understanding underwriting terms33:00 - Partnering in the insurance ecosystem and the value of relationships36:00 - Final thoughts: embracing versatility, teamwork, and continuous learningResources & Links:Commonwealth UnderwritersSarah Kulhoff - LinkedInCanopy ConnectMAV Insurance PlatformConnect with Sarah:LinkedInEmail

19 min
Feb 6, 2026Episode 318
The Lazy River Files!

In this episode, we are doing something a little different. Casey Nelson and I hosted an open call live one day and we called it the lazy river. WE wanted to invite people to "float in and hang out ad float out. Ive provided a few clips here for you guys to check out. WE will release the whole 2 hours some day soon... but for now this clip is about authentic leadership, engaging communication, and innovative work practices that can transform organizations. Whether you're speaking on stage, building relationships, or managing teams remotely, these insights provide practical strategies to lead with confidence.You'll hear familier voices ; Casey NelsonCaleb CramerCiara GravierJessica HolderBen MorrowRyan HanleyKey Topics:The importance of genuine interactions and how authenticity impacts leadership credibilityStrategies for modularizing content to adapt in dynamic speaking environmentsMemorable name drop stories and their impact on personal brandingTips for effective networking at high-profile events like Bill Gates's houseHow to test and engage audiences during keynote speechesThe role of diversity and gender dynamics in leadership credibilityFuture workplace trends: remote work, flexibility, and the four-day workweekLeveraging your unique strengths and circumstances to attract and retain talentPractical tips for transitioning from traditional to hybrid or virtual formatsTimestamps:00:00 - The value of authentic interactions and sharing personal stories02:24 - Memorable name drops and their role in networking04:41 - Insights from high-profile meet-and-greets and leadership impressions06:03 - Authenticity as a female CEO and gender dynamics in leadership08:28 - The power of candid panel discussions and last-minute updates09:28 - Modularizing content for impactful speaking engagements11:20 - Testing audience engagement in real-time during speeches12:50 - Perspectives on remote work, office culture, and flexibility14:45 - The future of work: four-day weeks and employee well-being16:20 - Strategies for small businesses to compete with large organizations17:13 - Wrapping up with humor and connecting through genuine communicationSPONSORS:Smart ChoiceCanopy ConnectMAV

31 min
Jan 30, 2026Episode 317
AI in your business!!

In this weeks episode,  release my virtual course in Bob Dietrich and Pamela Dunn's virtual program called "Unlease AI in your Business" that released this week. Hope you enjoy it. Let me know what you think... Sponsored by:Smart ChoiceCanopy ConnectMAV

41 min
Jan 22, 2026Episode 316
What should you be paying attention to in 2026?

In this week episode, Heath Shearon and Casey Nelson discuss the importance of standardizing processes in agencies, the impact of AI on business, and the potential societal reset from reducing screen time. They explore the challenges of implementing consistent procedures, the role of AI in modern companies, and the cultural shift towards more face-to-face interactions. The conversation also touches on the hypothetical scenario of shutting down the internet for six months and its potential effects on society. Additionally, they delve into personal anecdotes, the significance of setting goals, and the evolving landscape of the insurance industry.TakeawaysStandardizing processes is crucial for agency efficiency.AI is transforming business operations significantly.Reducing screen time could lead to a societal reset.Consistent procedures help in minimizing wasteful practices.Face-to-face interactions are becoming more valued.The internet shutdown could have profound societal effects.Agencies should focus on their most profitable clients.Building processes should involve employee input.AI tools can be both time-saving and time-consuming.Cultural shifts are moving towards more personal interactions.Setting personal goals can drive professional growth.Understanding industry trends is key to staying competitive.Chapters00:00:00 Introduction and Technical Issues00:01:00 Standardizing Processes in Agencies00:01:55 AI's Impact on Business00:15:55 Cultural Shifts and Screen Time00:20:19 Hypothetical Internet Shutdown00:25:00 Personal Goals and Anecdotes00:30:00 Insurance Industry TrendsSponsors:Smart ChoiceCanopy ConnectMAV

35 min
Jan 15, 2026Episode 315
Insurance Agency ownership looks a little different these days

This week in Insurance Town I get to catch up with my old friend, and former colleague, Therese Potter of Envela. We have a fun conversation we get to catch up on what she has been up to all the hats she currently wears, from teaching Tai Chi to selling Insurance and everything in between, and she is able to do all that, because of the culture and technology over at Envela. Check it out, and let me know what ya think...Sponsors:Smart Choice-Go to Smartchoiceagents.com Canopy Connect- Usecanopy.com/heathMAV- Hiremav.comThank you for being a wonderful and loyal citizen of Insurance Town! I love you all! from the bottom of my heart I truly do, and I appreciate your support all these years!!

1 hr 6 min
Jan 8, 2026Episode 314
Fair creates new opportunities and revenue streams for your agency!

In this episode of the Insurance Town Podcast, I sit down with Clint Houke for a wide ranging, high trust conversation to kick off the new year the right way. This is one of those talks that feels like two industry vets standing at the whiteboard, talking honestly about what is working, what is changing, and where the real opportunities are.Clint and I dig into the trends he is seeing across the insurance landscape, especially around MGAs and why they continue to play such a critical role in today’s market. We talk about speed, specialization, and why MGAs are not just filling gaps, but actively shaping the future of distribution.From there,  how agencies, MGAs, and carriers can think about AI as a tool to enhance relationships, not replace them. The conversation then turns to Clint’s newest chapter and his work with FAIR. We talk about what FAIR is building, why it matters, and how it is creating real opportunity in the insurance space. This is not just another product. It is a business model that opens up meaningful new revenue streams while staying aligned with transparency and customer experience.What stood out most in this conversation is Clint’s perspective on timing. The industry is changing fast, but the fundamentals still matter. Relationships. Trust. Doing right by the client. FAIR feels like one of those companies that understands both sides of that equation.If you are an agency owner, producer, MGA leader, or anyone looking to add smart, sustainable growth to your business, this episode is worth your time.Pull up a chair, grab a cup of coffee, and join us in Insurance Town for a conversation about trends, technology, and finding opportunity in a changing market.Welcome back to town.Sponsors:Smart Choice- the Fastest growing agency Network hands downMAV- Ditch the Call center and Hire Mav the AI solution to engaging your clients Canopy Connect - The One Click Solution to getting dec pages you need to quote your clients.

44 min
Jan 1, 2026Episode 313
Out Of Service Keynote from IIANC

HAPPY NEW YEAR!! Thank you so much for yet another amazing year in Insurance Town!! This weeks episode is a little different, No Guest. This week i am releasing one of my keynote presentations from a conference I spoke at this year, IIANC, thank you to my friend AUBE KNIGHT and his amazing staff in North Carolina for hosting me and helping me to learn and grow in a big way!! THAT CONFERENCE HAD a major impact on my life personally and Professionally!! This is my keynote, OUT OF SERVICE, I hope you enjoy! SponsorsSmart ChoiceCanopy Connect MAV

59 min
Dec 18, 2025Episode 312
Let's talk about influence!!

In this episode of Insurance Town, the Mayor sits down with Brian Ahearn to unpack the difference between social media influence and true leadership influence, while also sharing a meaningful conversation around faith, family, and the responsibility that comes with leading well. Brian reflects on how becoming a grandfather has reshaped how he thinks about legacy, humility, and the kind of influence that truly matters, both at home and in leadership.The conversation also dives into Brian’s new book, Influenced From Above, a business parable that blends leadership principles with faith driven purpose. Together, Brian and the Mayor discuss what it means to be influenced from above in their own lives, leading with empathy, serving others, and aligning values with action. The takeaway is clear: real influence is not about getting people to say yes, but about building trust, relationships, and a legacy that lasts.Key TakeawaysWhy social media influence is not the same as true leadershipHow faith and family shape the way leaders influence othersLessons from Influenced From Above on humility and serviceWhy empathy and trust are the foundation of lasting leadershipSponsorsSmart Choice – The fastest growing agency network hand down, no fees, higher commissions, lower premium thredhholdCanopy Connect – A one click solution to getting dec pages to quote your prospect and now they have intake platofrmMAV – Ditch the call center and hire MAV, the AI powered text messaging agent to qualify, quote& connect your prospects to your producers

44 min
Dec 11, 2025Episode 311
Is Self-Insuring the Future for Business Owners?

In this episode of Insurance Town, host Heath Shearon welcomes Van Carlson to discuss the evolution of risk management and the importance of self-insuring for businesses. They explore the 831B tax code, its history, and its application in modern business risk management. Van shares insights from his career in the insurance industry, highlighting the challenges and opportunities in self-insuring and the role of traditional insurance. The conversation also touches on the impact of economic downturns and the need for innovative risk management solutions.TakeawaysVan Carlson emphasizes the importance of self-insuring for businesses.The 831B tax code offers a way to manage business risks effectively.Traditional insurance may not cover all business risks.Economic downturns highlight the need for innovative risk management.Van Carlson shares his journey in the insurance industry.Self-insuring can provide financial stability for businesses.The conversation explores the history and application of the 831B tax code.Van Carlson discusses the challenges of transitioning from traditional insurance.Heath Shearon highlights the role of education in risk management.The episode provides insights into modern business risk management strategies.Sound bites"Self-insuring is the future of business risk management.""The 831B tax code is a game changer.""Traditional insurance doesn't cover all risks.""Economic downturns demand innovative solutions.""Education is key in managing business risks.""Self-insuring provides financial stability.""The 831B code offers unique advantages.""Transitioning from traditional insurance is challenging.""Risk management requires continuous learning.""Modern businesses need modern risk solutions."Chapters00:00:00 Introduction and Sponsorship00:00:00 Van Carlson's Background00:00:00 The 831B Tax Code Explained00:00:00 Challenges in Traditional Insurance00:00:01 Innovative Risk Management Solutions00:00:01 The Future of Business Risk ManagementSponsors:Smart Choice Canopy Connect MAV

57 min
Dec 4, 2025Episode 310
Can you lock in rates for your customers with the carriers you have in your agency?

In this weeks episode I sit down with Dylan Dimarchi of Eventual to talk about A product that is super cool

36 min
Nov 20, 2025Episode 309
Why blindly trusting technology can lead to significant risks...

In this engaging conversation, Heath Shearon and Alex Rodov explore the vibrant culture of Toronto, the evolution of technology and quality assurance, and the critical role of testing in the insurance industry. Alex shares his journey from humble beginnings to becoming a leader in the tech space, emphasizing the importance of methodology and the pressures faced in quality assurance. They discuss the challenges of trusting technology, the significance of consumer education, and the future of QA technology, including Alex's new book on testing.TakeawaysGrowing up in Toronto inspired Alex's passion for technology.Quality assurance has evolved significantly over the years.Pressure in QA is a constant, especially in critical industries.Methodology is essential for effective software testing.Consumer education is vital for understanding technology's reliability.The insurance industry heavily relies on quality assurance processes.Alex's book aims to educate consumers about testing.Investing in QA technology is crucial for future advancements.Chapters00:00 Exploring Toronto: A Cultural Hub06:03 The Evolution of Quality Assurance in Tech13:48 The Importance of Methodology in QA22:02 The Role of QA in the Insurance Industry30:12 Investing in the Future of QA TechnologySponsors:Smart Choice- the fastest growing agency network hands down Canopy Connect- your 1 click solution for all things dec pages, intake platforms etc MAV- the AI-powered insurance expert that engages unlimited leads with text messaging

36 min
Nov 13, 2025Episode 308
How did this agency use social media to fuel their growth in middle of nowhere Oklahoma?

in this weeks episode I sat down with my good friend Poppy Danker and have a blast talking about this small down agency and how she has just exploded in growth using social media. Yes you heard that right. Its wild to see!! Ive been watching this agency since the beginning from 500 followers to now over 25k followers and viral videos and the whole thing. its so fun. You just gotta hear this one ...sponsored by :Smart Choice Canopy Connect MAV

53 min
Nov 6, 2025Episode 307
No such thing as a bad lead... here's why...

This week in Insurance Town I sat down with my friend Evan Smith of Mav. We had an incredible conversation about growing your sales with leads and building an inside sales team . We discussed the importance of recognizing that you have to have a vision and a plan before working with leads and not try to scale too quickly We discussed the idea of there is no “bad lead” and what that means. We discover ways to write any lead . The numbers game that is leads and why MAV is THE go to for scaling and growing you business with online leads. Check this one out and hear his three pillars of working with leads successfully. And so much more Sponsors:Smart Choice® the fastest growing agency network hands down and now with 11,000 agencies across the country Canopy Connect -THE one click solution to getting the dec pages you need to quote your prospects and get loss runs and driver lists , and vehicle lists and , and and… check it outActivate to view larger image,

46 min
Oct 30, 2025Episode 306
AI in Insurance: Beyond the Buzzword

In this episode of the Insurance Town Podcast, Heath Shearon hosts Christopher Frankland to discuss the intersection of technology and insurance, focusing on AI's impact on the industry. They explore the concept of the 'bionic agent,' the role of AI in transforming insurance processes, and the future of human interaction in a tech-driven world. The conversation also touches on personal anecdotes, the importance of adapting to technological changes, and the potential for AI to enhance customer experiences.Takeaways:AI is transforming the insurance industry by automating processes and enhancing customer experiences.The concept of the 'bionic agent' combines human expertise with AI technology.Adapting to technological changes is crucial for staying relevant in the industry.AI is no longer just a buzzword; it's a fundamental shift in how we work.The insurance industry is fragmented, with varying levels of AI adoption.Human interaction remains essential, even as automation increases.AI can help solve real problems and tackle industry challenges.The future of insurance involves a blend of technology and human touch.AI's role in insurance is evolving, with potential for real-time risk assessment.Education and upskilling are vital for embracing AI in the industry.Sound Bites:AI is transforming insurance.The bionic agent is the future.Adapt to tech changes or fall behind.AI is a fundamental shift.Human interaction is still key.AI solves real industry problems.The future blends tech and human touch.Real-time risk assessment is coming.Education is key for AI adoption.AI is beyond just a buzzword.Chapters:00:00:00 Introduction and Guest Introduction00:00:00 AI's Impact on Insurance00:00:01 The Bionic Agent Concept00:00:02 Adapting to Technological Changes00:00:03 Future of Human Interaction in InsuranceSponsors:Smart Choice Agents Program- the fastest growing agency network hands down. Canopy Connect: Your one click solution for getting everything you need to quote your prospects

24 min
Oct 23, 2025Episode 305
Who would you invite to your block party?

This is an episode recorded at the PIA VADC conference in Virginia Beach with my man Byron Roberts.  It is a fast, on-the-ground conversation about how Openly built for independent agents, why speed still matters, and how data is shifting from rearview mirror to windshield. Quick recapOpenly’s origin story is agent-first. Founders Ty Harris and Matt Duffy asked agents what they actually needed, then shipped a three-question quote experience built to find “diamonds in the rough,” not write everything in sight. The company doubled down on listening loops like ACE, its Agency Council of Excellence, to sanity-check product decisions, fix friction fast, and keep writing business during a stubborn hard market. They are rolling into PL Rating in key states to cut keystrokes, and they see the next frontier as forward-looking data that helps carriers price for tomorrow’s weather, not yesterday’s. Key takeawaysBuilt by and for independent agents, not DTC. Choice and counsel are the strategy. Three inputs to quote, then verify details to bind accurately and quickly. Think seconds, not hours. ACE council gives Openly real-time agent feedback and a promise to report back on changes. Smart underwriting beats growth at any cost. Openly tightens or tweaks instead of pulling out. PL Rating integrations are in motion to reduce double entry and speed comparisons. Data is shifting from historical to predictive. Actuaries need “crystal balls,” not just rearview mirrors. Notable quotes“Tell me I can’t, I’ll show you I will.” Byron on persistence. “Three questions, name, date of birth, and address. We can get it.” On the quoting thesis. “We’re staying open for these agencies. We don’t tighten everything down or pull out.” On disciplined appetite. “We used to look at historical data. Now we need crystal balls.” On forward-looking pricing. Sponsor Smart Choice- The fastest growing insurance network, with 10,000 agencies, 11 billion in written premium written its incredibleCanopy Connect- your 1 click solution to getting the deck pages you need to quote your prospects.

54 min
Oct 16, 2025Episode 304
Grit, Growth and Gumption , Revisted

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 scary that might be. This episode is a really really good one. I couldn’t do this show without my amazing sponsors Smart Choice – the fastest growing agency network hands-down. With over 10,000 agencies across the country, trusting them and over 11 billion written premiumCanopy connect – you’re one click solution to getting the deck pages you need to quote your prospects

1 hr 2 min
Oct 9, 2025Episode 303
Hard to Place, Easy to Profit: The Art of Captives

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 taking chances, trusting data, and transforming the way independent agents think about risk.In this episode, we discuss:The evolution from retail broker to MGA and carrierWhy most agents misunderstand captives (and how to use them right)Building programs for high-risk industries like towing and hempHow to niche down without boxing yourself inThe role of AI in underwriting and program innovationKey Takeaways:Don’t fear the hard-to-place — that’s where opportunity lives.Captives aren’t restrictive; they empower growth and control.Niche success is built on relationships and risk awareness.AI is a tool, not a replacement — human insight still wins the day.Connect with Jeff Kleid:LinkedIn: linkedin.com/in/jeffkleidEmail: [email protected]: eliterisk.comSpecial Thanks to Our Sponsors: 🧡 Smart Choice – The fastest-growing agency network helping independent agents write more business and earn more income. 🔗 Canopy Connect – The easiest way to collect your client’s insurance information in seconds.

52 min
Oct 2, 2025Episode 302
The best tech make great service feel effortless (re-visit)

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 innovation. He provides perspective on how to stay ahead amidst these changes.Staying Connected in a Changing World: The conversation shifts to the importance of maintaining relationships in the insurance world, especially in a post-pandemic landscape. Patrick talks about his strategies for staying connected with colleagues and clients while continuing to adapt to the evolving industry.Customer Service and Technology: The conversation digs deep into how the evolution of technology has transformed customer service in the insurance world. Patrick emphasizes the need for agencies to use tech to enhance the client experience—whether it's through automation or more personalized service. They discuss tools like AI chatbots, data analytics, and client portals, which not only make processes faster but allow for a more tailored approach. As Patrick points out: "The best tech makes great service feel effortless."Patrick shares a few stories where tech simplified otherwise complex processes for clients, noting how a quick turnaround and personalized communication helped retain customers. The duo also touches on the challenge of finding a balance between automation and the human touch. "At the end of the day," says Patrick, "clients still want to know there’s a real person behind the scenes who cares about them."Rapid Fire Questions Segment: In a fun and fast-paced part of the episode, Heath puts Patrick in the hot seat with rapid-fire questions. Get ready for some hilarious and insightful moments as Patrick reveals:Favorite tech tool for improving customer service.Worst business advice he ever received.Favorite networking event (besides Indy Tech, of course!).Go-to grilling recipe—yes, there’s a little cooking talk!And much more!Customer Service Tech Takeaways for Insurance Pros:Speed & Efficiency with Tech: Use technology to streamline repetitive tasks like policy changes, claims processing, and FAQs to free up more time for personalized client interactions.Human Touch: While automation is a game-changer, it’s crucial to maintain a human connection for the moments that matter. Clients value tech for convenience but trust is built through real relationships.Data-Driven Personalization: Tools that provide data ins

37 min
Oct 2, 2025Episode 302
Is technology in your agency helping you close more deals? (return visit)

In this episode of the Insurance Town Podcast, Mayor Heath Shearon sits down with the dynamic Keith Harrison to talk about fun in the workplace, the importance of passion, and the journey that led Keith to where he is today. From LinkedIn connections to the power of networking, Heath and Keith dive deep into the sales process and the ideas and strategies he trains on all over the world.   Keith shares insights on finding joy in daily tasks, the philosophy of providing value over price, and some practical advice for making work feel less like work. Check this one out and hear more about:Building a Career on Passion – Both Heath and Keith explore the idea that if you love what you do, “you’ll never work a day in your life.”Keith shares practical sales tips that work Keith workings with agencies all over the world to bring sales game changing sales process to the tableHow his simple and easy steps can help you turn your CRM into an even more valuable member of your sales teambuilding a sales culture in your agency second to noneEpisode Sponsors:Smart Choice – Helping independent agents grow and succeed with tools and support that make running an agency easier.Canopy Connect – The ultimate insurance verification tool, allowing agents to streamline data collection and focus on building client relationships.Olde School Marketing – Your go-to partner for customized marketing solutions in the insurance space, from print to digital.

47 min
Sep 25, 2025Episode 301
What are the biggest data challenges in Insurance right now?

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 introspection and personal growth. The conversation also touches on the role of AI in solving business problems and the significance of building strong teams.Introspection is key to personal and professional growth.Data integration is more complex than it seems.AI should solve business problems, not just be a buzzword.Clean data is crucial for effective business operations.Building strong teams is essential for success.The insurance industry faces unique data challenges.Consulting offers diverse experiences but lacks depth.Startups require adaptability and resilience.Effective communication is vital in tech and insurance.Pilot programs can help improve data quality.Chapters00:00:02 Introduction and Jamie's Background00:00:36 Exploring Africa and Personal Growth00:03:01 Journey Through Startups00:05:26 Introspection and Personal Development00:08:20 Leadership and Team Building00:14:17 Data Integration Challenges00:18:41 AI in Business00:26:25 Consulting and Current Projects00:30:51 Future Plans and Team BuildingSponsors:Smart Choice Agents - The Fastest growing agency network hands downCanopy Connect- The one click solution to getting the information you need to quote your prospects

54 min
Sep 18, 2025Episode 300
How AI is continuing to evolve and change the game for agencies that embrace it!!

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, highlighting the innovative solutions his company, OneFort, is developing to streamline operations and enhance client relationships.TakeawaysAI is transforming the insurance industry by automating processes.Understanding client needs is crucial for effective insurance solutions.Technology can attract new talent to the insurance field.OneFort focuses on independent insurance agents to maximize impact.Manual processes in insurance are time-consuming and need automation.Cross-selling and upselling are key strategies for insurance growth.AI can help identify underinsured clients and recommend solutions.The insurance industry faces a talent shortage that technology can address.OneFort integrates with existing tools to streamline insurance workflows.Toby emphasizes the importance of continuous innovation in tech solutions.Chapters00:00:02 Introduction and Greetings00:00:05 Discussing Upcoming Events00:00:20 The Role of Magic in Trade Shows00:03:23 Toby's Journey in Insurance and Tech00:07:55 Miscommunication in Insurance and Tech00:16:21  Focus on AI for producers, and CSR's 00:29:01  AI Solutions for Insurance00:32:04 Cross-Selling and Upselling with AI00:39:32 Future Plans and Industry GrowthSponsors:Smart Choice The Fastest growing agency network in country! Hands DownCanopy Connect - Your 1 click solution to getting the dec pages you need to quote your prospects

39 min
Sep 11, 2025Episode 299
Mayor Solo

This one is a Mayor Solo! Mail bag episode! STICK AROUND and hang out with me. If you dont want to hear a solo episode , I get it , Go check out another one of your favorite shows, no hurt feelings here. But if you wanna hang out with me, I look forward to the next 39 minutes with you itll be fun Sponsors:Smart ChoiceCanopy Connect

59 min
Sep 4, 2025Episode 298
Intake Without the Headache - Town Hall Meeting

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 intake platform. They're one click solution that I've been talking about for 5 years now.  Thanks to Ray Huang for making the visit to Insurance Town and Showing us behind the scenes.  If you did miss this episode live, this is your chance to check it out. If you would like to learn more about Canopy Connect,  please go to usecanopy.com\ health and take advantage of the discount, book a demo, check it out. If you want to watch this episode go to our Youtube channel and check it out.  Sponsors Smart Choice- The fastest growing agency network hands down. 10,000 agencies nationwide trust them with over 11 BILLION  in written premium. Canopy Connect- Your One Click Solution to getting dec pages you need to quote your prospects.

54 min
Aug 28, 2025Episode 297
Choose Africa !

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 talented professionals from the continent. IntroductionHost introduction and episode overview Shoutout to sponsors: Smart Choice and Canopy Connect[03:15] Valerie's JourneyValerie shares her adventurous backpacking trip across Africa How her experiences led to the founding of Cradle[10:45] The Cradle MissionDiscussion on ethical outsourcing and creating sustainable jobs The importance of fair wages and supporting African talent[18:30] Bridging the GapHow Cradle connects African professionals with global businesses Success stories and client experiences[25:00] The Role of AIValerie's insights on AI's impact on virtual assistants How AI tools enhance the capabilities of offshore teams[32:15] Tips for Hiring Offshore TalentValerie's advice for businesses looking to hire from Africa Best practices for onboarding and training virtual assistants[40:00] Closing ThoughtsValerie's vision for the future of outsourcing Final words and how to connect with Valerie and CradleSponsors:Smart Choice: The fastest growing agency network, offering a wide range of services to help agencies thrive. Visit smartchoiceagents.com for more information. Canopy Connect: Revolutionizing the way agencies handle client data with their innovative intake form platform. Learn more at usecanopy.com.Want to work with Crdle ? want to contact Valerie Bowden

41 min
Aug 21, 2025Episode 296
Nothing fully launches unless it's in a process.

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 tech decisions."Nothing is fully launched until it's embedded in a process.""You should design your processes and your tech stack around the customer journey.""The greatest piece of tech that ever existed is just going to be a drain on the P&L if your people don't use it."Key Topics:The evolution from agency to tech operations Importance of aligning technology with agency processes Avoiding shiny object syndrome in tech adoption The role of team involvement in tech decisions Insights on building a cohesive tech ecosystemConnect with Thomas Mann on LinkedIn or visit agency-focus.com to book a call and explore how to enhance your agency's tech and operations.Link in first comment.

57 min
Aug 14, 2025Episode 295
Which ships are you riding in?

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 for listening. Thank you for subscribing. Thank you for helping me achieve my dreams.Thank you to my sponsorsSmart Choice® fastest, growing agency network, hands-down. Canopy Connect - the one click solution to getting dec pages,loss runs, but now they have a new intake platform you’ve got to check out

35 min
Aug 7, 2025Episode 294
Should Young, Married, and Divorced People Approach Life Insurance the Same way ?

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 personal passion in entrepreneurship. We also hear about iCover's unique approach to life insurance The role of community insurersThank You to Our Sponsors:Smart Choice: Your partner in insurance solutions. Canopy Connect: Simplifying insurance verification Olde School Marketing: Bringing traditional marketing into the digital age.

58 min
Jul 31, 2025Episode 293
Can Community and Innovation Reshape the Insurance industry?

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 importance of authenticity in content creation, the power of community in driving industry change, and his vision for the future of insurance. He also opens up about his personal experiences, from his family's influence on his career to his innovative strategies for marketing and growth. Whether you're an industry veteran or new to the field, Craig's insights offer valuable lessons on leadership, resilience, and the art of building a lasting brand.Chapters:0:00 - 5:00- Introduction to Craig Bender-Heath introduces Craig Bender and his accomplishments. -Discussion on Craig's bi-coastal lifestyle and recent award. 5:01 - 15:00Early Beginnings and Family Influence-Craig's introduction to the insurance industry through his family. -The impact of his mother's career and his early experiences. 15:01 - 30:00- Marketing Innovation and Insure U2-Craig's pivot to marketing and the creation of InsureU2. -The philosophy behind the brand and its community focus. 30:01 - 45:00 Content Creation and Industry Impact-Craig's approach to content creation and its influence on the industry. -The importance of authenticity and consistency in marketing. 45:01 - 60:00 Future Vision and Community Building-Craig's vision for the future of Insure U2 and the insurance industry. -The role of community and collaboration in driving change.Quotes:"Unity is everything... it shows that we're all together and on the same page." - Craig Bender "If I want something, I need money for it. How do you get money? You work." - Craig Bender "The content is what's going to live forever... it's the message that I'm saying." - Craig Bender "It's not about speed to market when you're building a longevity company." - Craig Bender "I love insurance, but I also love seeing other people win." - Craig BenderTune in to hear more about Craig's inspiring journey and his plans for the future of the insurance industry. Don't miss out on the insights and strategies that can help you grow your own brand. Subscribe now for more episodes!Sponsors:Smart Choice Agents Program Canopy Connect Olde School Marketing

54 min
Jul 24, 2025Episode 292
What secrets does he share on building personal brand?

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 building personal connections in business.00:02:00 Introduction to Draye Redfern and his background in insurance 00:10:30 The power of direct mail in modern marketing. 00:22:15 Draye discusses the ANKR framework for business growth.00:35:45 The importance of personal branding and social media presence.00:48:00 Understanding business metrics and their impact on success. 1:05:00 Closing thoughts and Draye's upcoming projects.Memorable Quotes:"Good marketing is really, really impactful." – Draye Redfern "The riches are in the niches." – Draye Redfern "It's five times to 25 times more expensive to go get a new customer than it is to simply retain an existing one." – Draye Redfern "The sweetest sound of someone's ears is the sound of their own name." – Draye RedfernGuest Information: Draye Redfern is the founder of Redfern Media and a seasoned marketing consultant. Connect with him on social media @DrayeRedfern or visit fractionalcmo.com for more insights.Explore Draye's book, "The Recession Survival Guide," available on Amazon and Audible, and stay tuned for his upcoming release on the ANKR framework.Sponsors:Smart ChoiceCanopy Connect Olde School Marketing

31 min
Jul 17, 2025Episode 291
IB FutureFest Recap !!

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 Monica Pier created a vibrant, festival-like atmosphere with activities like yoga, putt-putt, and live music. Attendees enjoyed a unique blend of professional development and leisure. Engaging Sessions: The event featured diverse sessions on AI, cybersecurity, and leadership, with industry experts like Christopher Franklin sharing their insights. The sessions catered to both agencies and carriers, offering valuable content for all attendees. Networking Opportunities: Future Fest fostered meaningful connections, allowing attendees to engage in deep conversations and build lasting relationships. The atmosphere encouraged networking in a relaxed and enjoyable setting. Sponsors & Support: A special thanks to sponsors Smart Choice, Canopy Connect, and Old School Marketing for their continued support, enabling such enriching experiences.Key Quotes:"If you do what you love, you never have to work another day in your life." "Future Fest was like adult summer camp, with new friendships and meaningful conversations." "The atmosphere was phenomenal, the backdrop was phenomenal, the speakers were phenomenal."Shout Out: A big thank you to Insurance Business and Key Media for organizing such a groundbreaking event. Their dedication to creating a unique and engaging experience truly set Future Fest apartCall to Action: Don't miss out on next year's Future Fest! Visit insurance.myfuturefest.com to join the waitlist for 2026.Sponsors:Smart ChoiceOlde School marketingCanopy Connect

55 min
Jul 10, 2025Episode 290
Exceeding expectations with Xceedance

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 insurance companies Insights on AI's impact on personal lines and customer service The evolving landscape of the E&S and MGA markets The importance of partnerships in the insurance ecosystemKey quotes "Exceedance does everything an insurance company does except for take risk and distribute products.""We tend to overestimate the impact of technology in the near term and underestimate it in the long term.""If I were to invest my capital in taking risks right now, I'd want to do it on an E&S basis.""I don't want to be called a vendor, I want to be a partner."Sponsors:Smart ChoiceCanopy ConnectOlde School Markting

56 min
Jul 3, 2025Episode 289
what is your plan for carriers 4-7?

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 statesHow to write the business others shy away from — without jumping through hoopsWhy MGAs and non-traditional carriers might just be your new best friendsThe critical importance of relationships — not just for quoting, but for long-term successBuilding your book with depth, not just volumeWhether you're a seasoned agency owner or a producer looking to grow smarter, Spencer delivers actionable insights that’ll challenge the way you think about growth  A big THANK YOU to the amazing folks who keep the lights on in Insurance Town:  Smart Choice – Helping agents grow their book without adding overhead  Canopy Connect – Making gathering client info as easy as pie  Olde School Marketing – Bringing you hand-written, high-touch prospecting that works Make sure to like, subscribe, and leave a review! New episodes drop weekly — straight from the heart of Insurance Town.

39 min
Jun 26, 2025Episode 288
This Agent Uses AI to WOW Every Client… Here’s How

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 example after example of how he's using ChatGPT right now to:✅ Personalize client interactions✅ improve your team's experience✅ build your own in house They ask you answer intranet ✅ Simplify complex insurance language ✅ Improve response times ✅ Drive more leads ✅ And yes… actually close more businessIf you’ve ever said, “I don’t have time to figure out this AI stuff,” this is the episode you can’t afford to skip. Chris lays out a playbook so practical, you’ll be tempted to pause and try it mid-episode.🔥 Brought to You By:💥 Smart Choice – The fastest-growing agency network in the game. More markets, less headaches. 💥 Canopy Connect – The one-click solution for collecting insurance data without all the back and forth. 💥 Olde School Marketing – Direct mail that actually works. Get noticed, get leads, get growing.🎧 Listen Now and Learn:

31 min
Jun 19, 2025Episode 287
How Do You Build a Thriving Agency Without Losing Your Marriage—or Your Mind?

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 have a great balance of community involvement and innovative technology at their fingertips, and lastly, they have a great balance of work and fun in their agency. We talk about:The delicate balance of marriage and co-ownership of a growing agencyHow human touch and community involvement is possible with the right technology in your agencyHow the emphases on educating their community on the intricacies of insurance is so valuable to their growthTheir powerful message of staying true to yourself and not sacrificing authenticity Get ready to be inspired and educated by this episode. It's a good thing there is a rewind button, this one is full of impactful moments.A special shout out to Vertafore for letting me reuse this episode : vertafore.com  A Special Thanks to Our Sponsors:🛠️ Smart Choice – Your partner for market access without the headaches. Whether you're a new agency or a seasoned vet, Smart Choice helps you stay independent while expanding your carrier options.🔐 Canopy Connect – The one-click solution for collecting insurance data. Save time, improve your close rate, and give your clients a seamless experience—because the quoting process shouldn’t feel like pulling teeth.📬 Olde School Marketing – Direct mail that actually works. Handwritten postcards, real human touch, and just the right dose of nostalgia to stand out in a digital world.

24 min
Jun 5, 2025Episode 285
Specialization in the insurance industry....Live from Virginia Beach !!

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 agents and the necessity of niche specialization to compete in a changing market. The episode concludes with advice for both new and seasoned agents on how to adapt and thrive in the evolving insurance landscape.takeawaysInformation sharing is essential for independent agencies.AI can streamline processes and improve efficiency.Niche specialization helps agencies stand out in the market.Independent agents are seeing a resurgence in demand.Proactive communication with carriers fosters better partnerships.Understanding carrier appetites is crucial for success.Technology can significantly enhance agency operations.Specialization allows for better training and support for staff.The insurance market is evolving, requiring adaptability.Building relationships with carriers can lead to better opportunities.Chapters00:00Welcome to Insurance Town02:123 people you would invite to your block party dead or alive?03:53what peice of tech could you not live without?4:45The Importance of Information Sharing5:00Embracing Technology in Insurance05:14Niche Specialization in Insurance12:25The Resurgence of Independent Agents14:26Advice for New and Existing Agents20:25Leveraging Technology for Efficiency