Most business owners know they need cyber insurance. Many already have it. But when a breach happens and the policy comes out for the first time in a year, the gap between what was assumed and what is actually covered can be alarming — and expensive. In this episode, host Bill Rountree sits down with Will Bracker, founding partner of Bracker & Holder and a nationally recognized voice on privacy and cybersecurity law. Will spent two decades in information technology — including hands-on cybersecurity work — before becoming an attorney, which gives him a rare perspective on the technical realities behind every clause in a cyber policy. The conversation moves past the surface and into the parts of cyber insurance that most business owners never look at until it’s too late: what first-party and third-party coverage actually pay for, why the application process has quietly become a de facto cybersecurity audit, how nation-state and AI-related exclusions can leave you exposed, and what an independent assessment of your coverage looks like when it’s done right.

Will’s central argument is simple but consequential: cyber insurance has been treated as a procurement activity, when it should be treated as a mission-critical security control — with the same diligence, the same independent review, and the same continuous reassessment that every other piece of your cybersecurity program receives.

What You'll Learn

• Why the cyber insurance application has effectively become a security audit — and what underwriters arenow requiring before they’ll bind coverage
• The major coverage categories every business owner should understand: first-party loss, third-party liability, business interruption, breach response services, and theincreasingly important exclusions
• Why "main chute vs. reserve chute" is the right way to think about cyber insurance — and what it means for how you should be testing your coverage
• How to bring independent assessors into the conversation, and the kinds of findings they typicallyuncover
• What to do right now if it’s been a while since you actually read your policy

If you remember nothing else from this episode: "Know what happens when you pull that reserve chute handle." Cyber insurance is your backup parachute. Treat it with the same diligence you bring to anything else mission-critical — because by the time you find out it’s packed wrong, you’realready falling.