Cyber Risk Management Podcast

AI made cybersecurity a speed race, so letting AI write your security patches sounds like the fastest way to keep up. New research tested that idea on six real bugs and more than 6,000 patch attempts. Only 26% fixed the bug cleanly. Kip and Jake explain why AI patches pass the tests but miss the flaw, why bad advice makes them worse than no advice, and four moves to get fast fixes that actually hold. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

 

"Frontier Models' Vulnerability Patches are Often F.L.A.W.E.D." by 1Password Off-by-1 Labs: https://1password.com/files/resources/frontier-models-vulnerability-patches-flawed.pdf

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

Your cyber strategy is only as strong as the people who carry it out. Deidre Diamond, founder and CEO of CyberSN, has spent more than 20 years studying the cybersecurity workforce. Learn the executive questions that reveal true capability, why burnout is an execution risk, and how a workforce map turns a headcount plea into a business case. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

LinkedIn: https://www.linkedin.com/in/deidrediamond/

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

CyberSN: https://cybersn.com

Your firewalls, access rules, and least privilege all assume software behaves the same way every time. AI models don't. So what still works, what breaks, and what should you build next? Our guest Dan Stocker, Principal Cybersecurity Architect at JPMorgan Chase and a Cloud Security Alliance contributor, explains why every AI agent needs its own identity, what your assistant's memory costs you in privacy, and where human judgment still matters most. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

 

LinkedIn: https://www.linkedin.com/in/danielastocker/

 

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

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

Tired of swinging the “compliance hammer” and hitting people until they submit to you? Would you rather be influential, and not dictatorial? Let's find out how you can with your hosts Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

 

See our previous episode on the subject of "buy-in" with our guest Michael Gregg, the CISO of North Dakota -- https://cr-map.com/podcast/171/