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. — SPONSORS: Abacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.ai 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 — 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 — RELATED EPISODES: The Coyle Group - Business Insurance https://www.youtube.com/@TheCoyleGroupNY — 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
