Episode
Will Brooks - Quantifying Cyber Risk Before Buying Insurance
- Podcast
- Keyboard Samurai
- Published
- Jun 8, 2026
- Duration seconds
- 1755
- Processing state
not_requested
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Summary
Cyber insurance is not a checkbox. It is risk transfer, and the details matter. Host Wil Klu talks with Will Brooks of U.Kon, formerly FifthWall, about how cyber insurance really works, why many businesses are underinsured, and how leaders should connect cybersecurity risk to financial impact. This episode is for business owners, CFOs, CISOs, CIOs, MSPs, and advisors who need to understand cyber policies without getting buried in insurance jargon. Key takeaways: • Why cyber insurance got more serious after COVID and ransomware growth • How to think about policy limits based on actual business loss • Why CISOs often understand the risk, but CFOs need the dollars • What MSPs and consultants can say without trying to sell insurance • Why add-on cyber coverage may not be enough • How comprehensive cyber insurance covers more than one type of incident Follow The Keyboard Samurai for more plain-English conversations on cybersecurity, business risk, and technology leadership. Find Will: https://www.linkedin.com/in/wi1bo/