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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SPONSORS:

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Metronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That’s why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.com

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Rillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cj

Tabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/run

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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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RELATED EPISODES:

The Coyle Group - Business Insurance

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

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TIMESTAMPS:

00:00:00 Preview and Intro

00:01:53 Sponsors — Abacum | Brex | Metronome

00:05:39 Interview Begins with Gordon Coyle

00:06:23 Gordon Coyle & The Coyle Group

00:07:21 Explaining Insurance on YouTube

00:08:40 Turning Education into Inbound Leads

00:09:40 Content as a Pull Strategy

00:10:53 Insurance Complexity for Tech Founders

00:13:28 Why Investors Require D&O Insurance

00:14:09 What D&O Covers and Why It Matters

00:15:50 Sponsors — RightRev | Rillet | Tabs

00:20:19 Who D&O Covers and Rising Investor Pressure

00:22:37 D&O Limits and Cost Tradeoffs

00:23:21 Panic Calls and Late D&O Purchases

00:24:39 How Defense Costs Erode Coverage

00:25:31 Common D&O Claims and Employment Risk

00:27:08 D&O vs E&O Explained

00:29:12 Cyber Insurance and Social Engineering

00:31:59 AI’s Impact on Cyber Risk

00:33:50 Real-World Ransomware Stories

00:34:17 Cyber Insurance as Money and Response

00:35:29 Business Email Compromise Scams

00:39:43 Why Tech Still Needs General Liability

00:41:16 What a BOP Covers

00:42:32 Convenience vs Proper Coverage

00:44:29 Surprising General Liability Claims

00:46:45 Insurance Costs for Startups

00:47:36 Higher Costs in High-Risk Industries

00:48:26 Balancing Budget, Risk, and Coverage

00:50:39 PEOs, Workers’ Comp, and EPLI

00:54:39 Choosing the Right Insurance Partner

00:56:42 End Credits

#RunTheNumbersPodcast #StartupFinance #BusinessInsurance #RiskManagement #CyberRisk

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

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