Why insurance feels complex to founders

Gordon explains why business insurance is complex and why founders trying to buy online often miss critical coverages.

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In this episode of Run the Numbers, CJ Gustafson sits down with Gordon Coyle, a 40-year commercial insurance veteran, to demystify one of the most anxiety-inducing topics for founders and CFOs: business insurance. Drawing on decades of experience with startups, scaleups, and regulated industries, Gordon breaks down what leaders need to know about D&O, E&O, cyber, and general liability, why investor pressure is rising, and where “cheap and easy” online policies fail when real risk hits. Through real-world examples, they explore how claims arise, how defense costs erode limits, why cyber insurance is as much about response as reimbursement, and how to balance budget, risk tolerance, and peer benchmarks—treating insurance as a critical layer of protection, not a box-checking exercise.

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LINKS:

Gordon on LinkedIn: https://www.linkedin.com/in/gordoncoyle/

The Coyle Group: https://thecoylegroup.com/

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

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The Coyle Group - Business Insurance

https://www.youtube.com/@TheCoyleGroupNY

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