Callan Harrington sits down with Lyndon Block, President & CEO of Block's Agencies, Prairie Insurance, Mello Insurance, and Rosthern Agencies, to explore his unconventional path to building 7 insurance brokerages across Saskatchewan. Lyndon shares how a chance encounter with marketing expert Chris Paradiso at a conference sparked a relentless pursuit of digital marketing mastery that changed everything. After being called out for doing "nothing" with his marketing efforts, Lyndon's persistence led to a life-changing mentorship in Connecticut, where he learned the fundamentals of digital growth.

The conversation reveals Lyndon's dual strategy of building both a self-funded digital insurance platform and acquiring struggling small-town agencies. He explains why distressed assets in rural communities represent hidden opportunities and how his boots-on-the-ground approach builds the trust necessary to turn around declining agencies.

This episode offers practical insights for anyone looking to grow through acquisition or build authentic community connections in their business.

Key topics covered:

[00:00] Intro
[02:09] Wake up call from insurance marketing guru
[03:32] Flying to Connecticut for free training
[05:55] Persistence as a competitive advantage
[08:00] Self funding a digital insurance agency
[09:27] Gary Vaynerchuk's cannibalization strategy
[11:19] Building API bridges for online insurance
[12:02] Old school door knocking for lead generation
[14:17] Two minute tenant insurance buying process
[16:37] Small town community strategy explained
[18:58] Why buy struggling insurance agencies
[21:33] Small town loyalty creates sticky clients
[25:02] Turning around distressed agencies
[28:40] Being present at hockey games and pancake breakfasts
[31:17] Using comedy to generate insurance business
[34:44] Digital versus community agencies coexisting
[36:56] Never say no to opportunities

Connect with Lyndon Block on LinkedIn: https://www.linkedin.com/in/lyndonblock/

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Curtis Barton didn't take the traditional path to building a large platform agency. He convinced six agency owners to merge their businesses, raise private equity capital together, and build something that had never been done in the industry. ALKEME is now ranked 21st on the Insurance Journal top 100, with over $2 billion in premiums written, $122 million in EBITDA, and 83 acquisitions completed.

Callan Harrington sits down with Curtis to break down how ALKEME was built from the ground up, why they moved every agency onto a single integrated system before anyone was talking about it, and how they use AI today to turn account managers from reactive paper pushers into proactive mini-salespeople.

This episode is a blueprint for any agency owner thinking about what it actually takes to scale past a lifestyle business and build something that lasts.

Key topics covered:

[00:00] Intro
[01:18] Skiing teaches business adaptation skills
[04:24] Why leaders must explain change
[06:48] Building agency from zero revenue
[09:02] Lifestyle business versus generational wealth
[11:00] Constant reinvestment beats traditional playbooks
[12:36] Eight agencies merge into platform
[17:19] Roadblocks to starting agency platforms
[22:23] Pick niche then hyper niche
[25:18] Organic growth fuels acquisition capacity
[28:58] AI automates workflow from inbox
[32:16] Blind scoring acquisition targets
[36:22] Scale beats growth every time
[40:07] Maturity means leading with intelligence
[44:49] Building forever company not exit

Connect with Curtis Barton on LinkedIn: https://www.linkedin.com/in/curtisbarton

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Callan Harrington sits down with Andy Cohen, President and COO of Snapsheet, to dive into why claims operations represent the biggest opportunity left in insurance, and what it actually looks like when carriers get it right. Andy brings perspective from both the carrier side and Snapsheet's work with over 180 carriers, including 16 of the top 20 P&C carriers.

Andy covers why loss adjustment expenses have barely moved even as premiums have surged, what modern claims operations actually look like when they're working, and what brokers and agents should be asking their carrier partners to hold them accountable on performance.

This episode provides actionable insights for anyone looking to understand how claims technology can drive better outcomes and competitive advantage in today's insurance market.

Key topics covered:

[00:00] Intro
[01:15] Change Management Takes 3 Years at Carriers
[03:02] AI Moving Fast in Insurance
[06:16] Snapsheet's 180 Carrier Network
[08:10] Claims Tech Overnight Success 14 Years Later
[10:59] Brokers Haven't Paid Attention to Claims
[15:28] Agents Can Vote With Their Feet
[18:03] Questions Agents Should Ask Carriers
[21:07] Best Practices from Top Carriers
[24:08] Key Questions About Loss Adjustment Expense
[26:28] Modern Claims Process Breakdown
[30:40] Where Agents Insert Themselves
[32:49] The Next 10 Years of Claims
[36:03] Modernization vs True Transformation
[38:31] Claims as Competitive Advantage

Connect with Andy Cohen on LinkedIn: https://www.linkedin.com/in/andrewjustincohen

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