In this episode, I sit down with John Czapko, CEO of CyberSecure, a leader with 26 years of experience in IT before founding a successful commercial insurance firm. That rare blend of technical expertise and risk management insight gives John a unique perspective on one of today’s biggest business challenges: cyber insurance.

John explains why the current cyber insurance landscape is broken—where policies don’t align with real-world tech stacks, brokers can’t translate cyber risk into business terms, and companies are left hoping instead of knowing when incidents occur.

We dive into how CyberSecure is changing the game with trusted carrier partnerships, coverage that stands up to audits and regulatory demands, and proprietary tools like the CyberSecure RiskMeter and Board Brief, which turn complex cyber threats into clear business strategy.

If your business can’t afford to get cyber wrong, this conversation will help you understand how to make cyber insurance make sense—and make sure it performs when it matters most.