188: Are You Risking Everything? The Insurance Your Business Can't Operate Without (Part 3)

In the compelling finale of this three-part insurance series, host Kirsten Howe and insurance expert Dean Myers tackle the coverage that keeps business owners up at night—cyber insurance. Dean shares fascinating real-world stories, from ransomware attackers offering customer service hotlines to disgruntled employees planting digital "time bombs" in company systems. You'll discover why this isn't just another insurance policy but essential business survival protection that covers everything from system failures to deepfake fraud. Dean reveals the surprising realities about whether companies should pay ransoms, how insurers use "white hat" attacks during applications, and why Silicon Valley startups are outpacing traditional insurance giants. If you think your business is too small to be targeted or that basic IT protection is enough, this episode will be a wake-up call you can't afford to ignore. Time-stamped Show Notes: 0:00 Introduction 1:12 What is cyber insurance, and why it's the broadest coverage for such esoteric risks? 1:48 The comprehensive scope: system failure, ransomware, business email compromise, business interruption, contingent business interruption, and forensics coverage. 2:15 Why cyber claims require hiring attorneys, CPAs, forensics experts, claims adjusters, and legal counsel, unlike traditional workers' comp claims. 2:45 The two key reasons carriers provide such broad coverage: rapid system restoration at the lowest cost and mandatory industry claim reporting. 3:48 How cyber insurance provides both first-party and third-party coverage, protecting you when you accidentally send infected emails to clients. 4:37 Real-world business email compromise: When hackers send fake invoices to your clients from compromised email accounts. 5:10 Why cyber attacks almost always originate overseas in countries with lax cybersecurity laws and accountability. 5:37 Will cyber insurance pay ransoms, and when is it appropriate? 6:42 Real claim story: How a tired CPA two days before tax season fell for a phishing email with a partner's name containing just one extra letter 8:25 Why paying ransoms creates a "bull's eye on your back" and marks you as a repeat target for extortionists. 11:06 Cyber insurance qualification requirements, why multi-factor authentication is now absolutely mandatory across all carriers. 12:15 "White hat" mock attacks: How insurers test your system vulnerabilities during the application process using the "open parking spot" analogy. 14:41 Insider sabotage case study: Bay Area law firm manager discovers her job posted on LinkedIn, teams up with IT brother-in-law for revenge. 15:53 The emerging deepfake threat, how voice cloning technology is creating new fraud risks for fund transfers. 16:25 Protection strategies: Using "trip questions" with personal knowledge to verify client identity during suspicious calls. 17:12 The AI counterbalance: How artificial intelligence may help prevent cyber claims in the future. Take the Next Step in Your Estate Planning Journey If this episode resonated with you, we'd love to help you with your own estate planning needs in California. Schedule a complimentary discovery call with our team at Absolute Trust Counsel. During this no-obligation conversation, we'll: Learn about your unique situation and goals Answer questions about our services Determine if we're the right fit to work together Visit or call 925-943-2740 to schedule your free discovery call today. Follow and Review: We'd love for you to

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188: Are You Risking Everything? The Insurance Your Business Can't Operate Without (Part 3) is an episode from Absolute Trust Talk by Kirsten Howe.

This episode is 16:44 long.

This episode was published on Jul 25, 2025.

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