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Cyber Risk Management Podcast

by Kip Boyle

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Latest episodes

EP 221: Cyber Risk Is Workforce Risk

October 20, 2026 · 46 min

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…
EP 220: Every AI Agent Needs Its Own Name

October 6, 2026 · 51 min

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…
EP 219: Why Gears Don't Guess

September 22, 2026 · 52 min

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…
EP 218: The “Compliance Hammer” Alternative (REPLAY)

September 8, 2026 · 45 min

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…
EP 217: When Hospital Systems Go Down, Who Keeps Patients Safe?

August 25, 2026 · 49 min

When a hospital's systems go down, care does not stop. It goes back to pen and paper, and the first sign is quiet, because the alerts stop. Physician and CISSP Mark Yoffe explains clinical compensating controls: the steps clinicians take…

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EP 216: When Reasonable Beats Bankrupt

August 11, 2026 · 53 min

After a breach, you either pay the fine, or fight the regulator and lose. There's a third path. It comes down to one word: reasonable. A method called DoCRA turns that question into something a court can use. DoCRA is short for Duty of…
EP 215: Is Your AI Strategy a Risk Decision in Disguise?

July 28, 2026 · 52 min

There's a popular new playbook for running an "AI-native" company. Record everything, put all your data in one place, and let an AI agent reach all of it. The productivity story is real. New hires ramp up in days, and the whole company can…
EP 214: AI Agents Don't Behave Like Humans

July 14, 2026 · 40 min

Your cybersecurity tools were built for people: a login, a single sign-on, an email address. But the AI agents now showing up inside your company don't work that way, and most of them slip right past your controls. So how do you find the…
EP 213: The Group Writing the Rules for AI Trust

June 30, 2026 · 48 min

Would you know if the AI tools your team is buying are actually trustworthy to use? Who gets to decide what trustworthy AI even means? Let's find out with our guest Jim Reavis, CEO of the Cloud Security Alliance, the group that helped the…
EP 212: The AI Worked. The Process Didn't.

June 16, 2026 · 47 min

Anthropic, the company that built Claude, just accidentally published the full source code of their most important product. And it was their second data exposure in five days. What does this teach every organization buying AI tools right…
EP 211: What Sea-Tac’s Ransomware Revealed

June 2, 2026 · 47 min

In August 2024, a ransomware attack shut down baggage systems, flight displays, and Wi-Fi at Sea-Tac Airport. What did it reveal about how executives think about cyber investment? And why is “how much more security do we need?” the wrong…
EP 210: How Boards of Directors Are Thinking About Generative AI

May 19, 2026 · 46 min

What does the generative AI conversation actually sound like inside a boardroom? Is the board ready to govern it? And what do board members wish CISOs understood about how they make decisions? Let’s find out with our guest, Vanessa…

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About the show

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.