Owning the Future of Enthusiast Insurance: A Conversation with Jeff Briglia

As the year comes to a close, it’s time to reflect on what truly moved the needle.

Bryant Kolle and John Gessner look back on a year defined by growth, community, and meaningful industry insight. They’re joined by special guest Jeff Briglia, President of Insurance at Hagerty. Jeff shares his career journey through companies like of Plymouth Rock, and what makes Hagerty genuinely different in insurance.

The conversation explores customer-first culture, shifting generations of car enthusiasts, and what it all means for agents today. 

Here’s what we’ll cover in this episode:

(00:35) Reflections from The Accelerator in 2025

(06:01) Career shift for work-life balance

(06:38) Pivoting to Progressive

(10:47) Plymouth Rock’s market mastery

(16:07) Hagerty’s classic car expertise

(17:14) Building connection through car restoration

(21:52) Enhancing insurance for modern needs

(25:09) Adapting to today’s car owners

(27:26) Cross-functional growth through curiosity

(31:38) Hagerty’s distribution and partnerships

(35:07) Supporting independent agents

(37:07) Specialized car insurance guidance

(42:23) Being a force for good

(44:47) Generational shifts and future solutions

(46:50) End better, be good

Links mentioned in this episode:

Connect with Jeff Briglia on LinkedIn

The Hagerty approach to collector car claims: https://www.hagertyagent.com/resources/hagerty-insights/accelerating-trust-hagerty-claims-team 

The difference between ACV, Stated Value, and Guaranteed Value®: https://www.hagertyagent.com/resources/hagerty-insights/guaranteed-value 

Hagerty’s Cars You Should Know for agents and brokers: https://www.hagertyagent.com/resources/hagerty-insights/cysk-shift-into-high-gear-for-a-winning-year-ahead 

Send your questions and feedback to Bryant and John at theacceleratorpodcast@hagerty.com