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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Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics
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
RightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.com
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
