EP 219: Why Gears Don't Guess artwork
Cyber Risk Management Podcast

EP 219: Why Gears Don't Guess

  • E219
  • 52:29
  • September 22nd 2026

Every system you've ever governed is a gear. Same input, same output. AI is the first system that guesses back, and that's why your management instincts misfire on it. Kip's new book, Gears Don't Guess, is out Sept 28th. Jake interviews him on why he wrote it, who it's for (the CFO, the general counsel, the risk manager, and the CISO), and the practical tasks, templates, and self-assessment that make it work on the job. The Kindle version is free through Oct 2. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

 

"Gears Don't Guess" by Kip Boyle (paperback and Kindle):https://www.amazon.com/dp/B0HHTKN8BZ

Free self-assessment and templates:https://gearsdontguess.com

"Fire Doesn't Innovate" by Kip Boyle:https://a.co/d/0bYatohy

Cyber Risk Management Podcast

Cyber risk made clear for busy leaders. Cyber threats move fast. Your business must move faster. In every episode, Kip Boyle—author of "Fire Doesn’t Innovate" and CISO at Cyber Risk Opportunities—joins cybersecurity attorney and CISSP Jake Bernstein to break down the latest cyber risk. You’ll hear plain-English explanations of what's going on and what you need to do about it. No jargon. No doom. Just clear steps you can use today to save money, win buy-in, and stay out of the headlines.