The Insurance Growth Lab

Callan Harrington
  • 5.0 (16)
  • ENTREPRENEURSHIP
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Host Callan Harrington dives into the strategies, decisions, and lessons that have shaped the careers of top marketing and growth leaders in the insurance industry. From bold moves to costly mistakes, each episode uncovers real-world insights that listeners can apply to accelerate growth in their own businesses.

  1. 2D AGO

    Kyle Nakatsuji on What the Future of AI in Insurance Actually Looks Like

    Host Callan Harrington sits down with Kyle Nakatsuji, CEO and Founder of Clearcover and Dearborn Labs, to explore how AI is reshaping insurance from the ground up. Kyle shares his unconventional path from persistent business school dropout to insurance entrepreneur who raised over $500 million and built technology capable of processing claims in 7 minutes. The conversation dives into Kyle's decision to launch Dearborn Labs, essentially bringing a decade of hard-won AI deployment lessons to carriers and agencies who can't afford to wait. Kyle explains why the recent leap in reasoning capabilities from frontier models like Claude Opus 4.6 represents a genuine inflection point, not just incremental progress. He outlines a future where agents interact with AI orchestrators rather than navigating fifteen carrier portals, with context rather than software becoming the true competitive currency in insurance. Kyle's insights on the K-shaped economy emerging from AI adoption offer a clear roadmap for insurance professionals ready to embrace the technology revolution transforming their industry. Key topics covered: [00:00] Intro[03:42] Business school persistence pays off[06:13] Competing against billion dollar ad spends[07:07] Seven minute claim payout achievement[08:15] Why launch Dearborn Labs now[10:27] AI breakthrough moment arrives[12:23] Agent experience transformation begins[15:11] API for AI agents explained[20:11] Who builds the connection layer[24:18] K shaped AI adoption reality[28:34] Start simple with AI tools[31:06] Technology curve never flattens[32:18] Discovery process for carriers[35:58] Building hammers versus finding nails[37:17] Advice to younger self Connect with Kyle Nakatsuji on LinkedIn: https://www.linkedin.com/in/kylenakatsujiSubscribe to The Insurance Growth Lab for more tactical growth strategies from industry leaders.

    39 min

  2. MAR 26

    How Matt Naimoli Built a Referral Network with 1300 Custom Bobbleheads

    Matt Naimoli went from college baseball player to building one of the fastest-growing insurance agencies in America using an unconventional $10,000 bobblehead campaign. What started as a networking attempt became a systematic referral machine generating 500 warm leads monthly with a 75% closing ratio. In this episode, Callan Harrington sits with Matt to break down the exact process behind the campaign that helped his agency capture 7% of all new home sales in Massachusetts. He reveals how they identified centers of influence, created systematic follow-up processes, and built relationships with 100+ referral partners who consistently sent high-quality leads. Matt also shares insights from his current role helping agency owners maximize their business value for acquisition. He explains what buyers actually pay premiums for, why growth matters more than book composition, and how to position your agency in today's market. Whether you're starting an agency or looking to scale, this episode provides a blueprint for building sustainable referral systems that compound over time. Key topics covered: [00:00] Intro[01:17] Baseball to Insurance Career Journey[04:24] Sales Stereotypes vs Reality[06:11] From Liberty Mutual to Agency Success[07:05] The Office Inspired Bobhead Campaign[10:11] Identifying Centers of Influence Strategy[12:08] Building Systematic Networking Processes[16:26] Written Process for Relationship Building[19:47] Modern Bobhead Campaign Revival[23:23] What Drives Agency Valuation Today[27:42] Scale Growth and Leadership Matter Most[32:29] Advice for Next Generation Agency Owners[34:41] How Carriers Can Support Growth[38:39] Long Term Reputation Over Shortcuts Connect with Matt Naimoli on LinkedIn: https://www.linkedin.com/in/mattnaimoli Subscribe to The Insurance Growth Lab for more tactical growth strategies from industry leaders.

    41 min

  3. MAR 20

    Jim Waterwash's Playbook for Retaining Clients After an Agency Acquisition

    Host Callan Harrington sits down with Jim Waterwash, Partner at INSocial Risk Advisors, to get into the details behind their 90%+ retention rate across 5 agency acquisitions, as well as the hard lessons that got them there. Jim traces the arc from running a fully digital agency selling 100% over the phone, to building a traditional operation with 20+ employees, $20M+ in premium, and a repeatable acquisition playbook. The insight that changed everything: the challenge of retaining a client you've never met is the same whether they came through an online lead or a book of business you just purchased. The conversation gets specific on how they identify cross-sell opportunities (they have actual coverage thresholds), how their pod-based service model works in practice, and why trying to build standard operating procedures collaboratively with acquired teams instead of arriving with them already built is big mistake. This episode offers actionable insights for agency owners considering acquisition strategies or looking to improve retention rates across diverse client bases. Key topics covered:[00:00] Intro[01:05] First Policy Double Charge Disaster[03:54] From Digital Leads to Traditional Agency[05:24] Why Digital Strategy Stopped Working[06:40] Acquisition Retention Similarity Insight[08:50] Great Insurance Minds Foundation[10:10] Book Integration Process Walkthrough[11:14] Change Management and Cultural Buyins[12:11] Cross Selling Acquired Books[14:03] Pod Based Service Model[16:51] Early Acquisition Road Bumps[19:42] Standard Operating Procedures Missing[22:17] Proving Systems Before Implementing[24:44] Craft Brewery Cash Deal[27:09] Cultural Alignment During Courtship[29:59] Carrier Support for Acquisitions[31:37] Keep Going Advice Connect with Jim Waterwash on LinkedIn for more marketing insights and strategies: https://www.linkedin.com/in/jwaterwash/ Subscribe to The Insurance Growth Lab for more tactical growth strategies from insurance industry leaders. New episodes every week.

    33 min

  4. MAR 12

    How Jeff Snyder Built Matic to 750K Leads Through Loan Servicing Partnerships

    Callan Harrington sits down with Jeff Snyder, President of Matic, to break down how an “unqualified” first employee built one of the most successful embedded insurance platforms in the mortgage servicing space. Jeff shares the unconventional strategy behind generating 750,000 leads annually by focusing on loan servicing rather than origination, targeting 65 million outstanding mortgages instead of the typical 4 to 6 million new home loans. Jeff walks through the three distinct phases of scaling Matic from an 800 square foot office to over 400 employees and 50 million in funding. He reveals his 3 by 3 relationship grid for partnership management, lessons learned from losing a major partner due to relationship turnover, and why providing value before asking for conversion creates lasting partnerships. The conversation covers everything from making 350 cold calls daily in the early days to building deep integrations with mortgage servicers that prove measurable impact on their core recapture rates. An essential listen for anyone building partnership-driven growth strategies or navigating the challenges of scaling from startup to enterprise. Key topics covered: [00:00] Intro[03:01] Taking Unqualified Opportunities That Change Careers[05:08] Becoming First Employee Twice[07:17] Generating 750,000 Leads Per Year[08:30] Why Loan Servicing Beats Origination[11:32] Triggering Customer Interest Through Data[14:05] Building Revenue Share Partnerships[18:02] Adding Value Without Selling[21:18] Proving Impact on Customer Retention[23:03] Losing a Major Partner[25:05] Building 3x3 Relationship Grids[30:23] Evolving Through 3 Company Stages[32:31] Scrappy Startup Phase Stories[36:37] Scaling Challenges and Bad Hires[38:27] Building Elite Leadership Teams[39:11] What to Stop Doing at Each Stage Connect with Jeff Snyder on LinkedIn for more marketing insights and strategies: https://www.linkedin.com/in/jeffrey-snyder-9189b317/ Subscribe to The Insurance Growth Lab for more tactical growth strategies from insurance industry leaders. New episodes every week.

    44 min

  5. FEB 26

    How Eric Roberts Built the Cross-Sell System Behind His $20M Agency

    Callan Harrington sits down with Eric Roberts, owner of My Insurance Group, to break down the systematic approach behind building a $20 million agency that generates 270 new inbound leads monthly without any cold calling. Eric brings a unique perspective to insurance sales, having spent 15 years on the claims side doing water and fire restoration before transitioning to agency ownership.  The conversation dives into Eric's cross-sell engine, which has more than doubled his policies per household. His team operates under a "respectfully aggressive" motto, focusing on thorough discovery during every client interaction to uncover additional insurance needs. Eric explains his unique team structure that separates new business, renewal, and service teams, with each playing a specific role in the cross-sell process. He also shares the tactical systems his agency uses, from their renewal questionnaire process to their CRM tagging system that tracks every opportunity. Eric's systematic approach shows how independent agencies can compete with the efficiency of captive carriers while maintaining their flexibility advantage. Key topics covered: [00:00] Intro[01:16] Career Journey from Claims to Sales[03:03] Understanding Insurance from Claims Perspective[04:33] 270 Monthly Leads Without Cold Calling[05:21] Respectfully Aggressive Agency Philosophy[06:37] Discovery Process for New Prospects[08:28] Standardized Scripts vs Producer Freedom[10:38] Detailed Renewal Journey System[14:50] Unique Team Structure Strategy[17:47] Why Separate Renewal and Sales Teams[20:07] Service Team Cross-Sell Process[22:17] Building Systematic Cross-Sell Culture[27:11] First Step for Starting Cross-Sell[30:16] Path to 50 Million Premium Connect with Eric Roberts on LinkedIn for more marketing insights and strategies: https://www.linkedin.com/in/eric-roberts-1b819b5b/ Subscribe to The Insurance Growth Lab for more tactical growth strategies from insurance industry leaders. New episodes every week.

    32 min

  6. FEB 19

    How Eddie Knezevich Built a Lead Machine Through Continuing Education Webinars

    Callan Harrington sits down with Eddie Knezevich, President & CEO of NLF Partners, to break down the continuing education lead generation system that transformed his wealth management practice. Eddie shares how he built a machine that generates 2000 qualified leads monthly without relying on friends and family networks or traditional cold calling. Eddie walks through his journey from hosting 3-person events in Newark, Ohio to running virtual webinars with 2500 attendees across multiple states. He explains the tactical details of his process-driven approach, from surveying audiences to create relevant content to converting attendees into scheduled consultations. The conversation covers the compliance challenges of expanding across state lines, the infrastructure required to scale continuing education programs, and how Eddie uses this system to feed his team of 12 advisors who manage billions in assets. Eddie emphasizes focusing on what you know and building systems that work without you, sharing lessons learned from 10 years of refining this lead generation approach. Key topics covered: [00:00] Intro[03:42] From Upper Middle Class to Food Stamps[06:09] Building Momentum After Rock Bottom Years[08:29] Factory Model Approach to Financial Services[10:53] First Continuing Education Event Disaster[12:01] Surveying Clients to Create Better Content[16:15] Building Transactional Relationships First[18:43] Marketing Process and Lead Generation Flow[21:27] Compliance Hurdles Across Multiple States[24:56] Marketing Tactics for Million Person Email List[29:57] Multiple Revenue Streams Beyond Ce Events[31:09] Focus on What You Know Best[33:24] Own What You Sell Philosophy[35:42] Starting Over Lessons Learned[37:08] Hiring People Sooner Despite Impostor Syndrome[40:47] Sacrificing Twenties to Build Lead Machine[42:31] Final Thoughts Connect with Eddie Knezevich on LinkedIn for more marketing insights and strategies: https://www.linkedin.com/in/eddieknezevich/ Subscribe to The Insurance Growth Lab for more tactical growth strategies from insurance industry leaders. New episodes every week.

    43 min

  7. FEB 12

    How Patrick McBride Built an Insurance Agency Targeting Harley Davidson Owners

    Host Callan Harrington sits down with Patrick McBride, founder of The McBride Agency, to explore his unconventional approach to building a successful independent insurance agency. Patrick shares how he transformed his personal passions for motorcycles and cycling into profitable niche markets, targeting high-value clients who own expensive Harley Davidson motorcycles and premium bicycles. Patrick dives into his creative marketing strategy to reach motorcycle enthusiasts and discusses the importance of understanding coverage needs specific to these communities, from accessory upgrades to personal articles floaters. The conversation covers his biggest operational challenges as the agency has grown, including knowledge transfer to new team members and the critical importance of carrier ease of use over pricing. Patrick delivers practical insights on community-based marketing, niche targeting strategies, and the systems needed to scale a scratch-built insurance agency. Key topics covered: [00:00] Intro[01:14] Never Give Clients Your Cell Phone[08:42] Targeting Harley Davidson Owners[12:46] Using Reddit for Customer Acquisition[16:10] Creating Custom Audiences Through Pixelation[18:16] Building Community Through Referrals[20:29] Operationalizing Niche Marketing Strategies[24:35] Launching the Cyclist Community Focus[30:22] Current Agency Growth Challenges[32:42] What Carriers Are Doing Right[35:59] Starting an Agency From Scratch Connect with Patrick McBride on LinkedIn for more marketing insights and strategies: https://www.linkedin.com/in/patrick-j-mcbride/ Subscribe to The Insurance Growth Lab for more tactical growth strategies from insurance industry leaders. New episodes every week.

    40 min

  8. FEB 5

    How Andy Harbut Scaled a Niche Insurance Brokerage in One Year

    Callan Harrington sits down with Andy Harbut, Co-Founder of NewCo Risk, who built a multi-million dollar insurance brokerage in just one year after leaving the big brokerage world. Andy shares how he and his partner, Josh, carved out their own path, focusing on search fund clients and lower middle-market private equity deals. With 75% of their clients being entrepreneurs who bought their own businesses, Andy explains why this niche offers more personal satisfaction than working as a cog in a large institutional machine. Andy breaks down their growth strategy built on old-school relationship building through conference sponsorships, university events, and face-to-face networking within the search fund community. He discusses the challenges of carrier selection across 40 states, why they wholesale specialty lines to true experts, and how they compete against major brokers by offering intimate client relationships and direct accountability. The conversation covers everything from insurance diligence in M&A transactions to why Andy insists on calling himself a broker rather than an agent. This episode offers tactical insights for any insurance professional looking to understand niche market development and independent brokerage growth strategies. Key topics covered:[00:00] Intro[04:26] Why Start Your Own Brokerage[07:51] Extreme Growth in Search Fund Niche[13:14] Unique Competitive Positioning Advantage[16:01] Old School Selling Insurance Strategy[17:32] University Conference Marketing Approach[20:03] Building Messaging Around Unknown Problems[21:58] National Carrier Selection Challenges[24:06] Program Business Growth Strategy[28:20] Leveraging Underwriting Office Arbitrage[32:46] Wholesaling vs In-House Expertise[36:21] Why Broker Not Agent[39:49] Fee Only Model Exploration[42:54] Growing the Team Connect with Andy Harbut on LinkedIn for more marketing insights and strategies: https://www.linkedin.com/in/andyharbut/ Subscribe to The Insurance Growth Lab for more tactical growth strategies from insurance industry leaders. New episodes every week.

    44 min
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5
out of 5
16 Ratings

About

Host Callan Harrington dives into the strategies, decisions, and lessons that have shaped the careers of top marketing and growth leaders in the insurance industry. From bold moves to costly mistakes, each episode uncovers real-world insights that listeners can apply to accelerate growth in their own businesses.

Information

  • Creator
    Callan Harrington
  • Years Active
    2022 - 2026
  • Episodes
    139
  • Rating
    Clean
  • Copyright
    © 2026 Callan Harrington
  • Show Website
    The Insurance Growth Lab