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Cyber Risk Management Podcast

Cyber Risk Management Podcast

Kip Boyle 211 Episodes Oct 6, 2026

Cyber Risk Management Podcast helps busy leaders understand and manage cyber threats. Hosted by Kip Boyle, author of "Fire Doesn’t Innovate" and CISO at Cyber Risk Opportunities, along with cybersecurity attorney Jake Bernstein, the show breaks down the latest cyber risks in plain English. Each episode provides clear, actionable steps to save money, gain buy-in, and avoid making headlines. No jargon or doom, just practical advice for today's business environment.

Episodes

EP 220: Every AI Agent Needs Its Own Name
EP 220: Every AI Agent Needs Its Own Name Oct 6, 2026 00:50:31 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
EP 219: Why Gears Don't Guess
EP 219: Why Gears Don't Guess Sep 22, 2026 00:52:29 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 t
EP 218: The “Compliance Hammer” Alternative (REPLAY)
EP 218: The “Compliance Hammer” Alternative (REPLAY) Sep 8, 2026 00:45:23 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 -- ht
EP 217: When Hospital Systems Go Down, Who Keeps Patients Safe?
EP 217: When Hospital Systems Go Down, Who Keeps Patients Safe? Aug 25, 2026 00:48:30 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 to keep patients safe during downtime. He covers who owns the clinical workflow, how to make controls workable and tested, how to recover information lost in
EP 216: When Reasonable Beats Bankrupt
EP 216: When Reasonable Beats Bankrupt Aug 11, 2026 00:53:12 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 Care Risk Analysis. Our guest Chris Cronin of HALOCK Security Labs helped build it. Now it's in standards and law. And it shaped a real case where a breached c
EP 215: Is Your AI Strategy a Risk Decision in Disguise?
EP 215: Is Your AI Strategy a Risk Decision in Disguise? Jul 28, 2026 00:51:59 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 ask questions it never could before. But the same moves that create the speed also switch off safeguards that some businesses are not allowed to switch off
EP 214: AI Agents Don't Behave Like Humans
EP 214: AI Agents Don't Behave Like Humans Jul 14, 2026 00:39:44 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 "Shadow AI" already running in your business, and get a handle on it? Let's find out with our guest Nancy Wang, Chief Technology Officer at 1Password, who wo
EP 213: The Group Writing the Rules for AI Trust
EP 213: The Group Writing the Rules for AI Trust Jun 30, 2026 00:47:36 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 world learn to trust the cloud and is now building the standards for trusting AI. Jim explains how AI is changing what attackers, defenders, and governments
EP 212: The AI Worked. The Process Didn't.
EP 212: The AI Worked. The Process Didn't. Jun 16, 2026 00:47:11 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 now? Kip Boyle shares the best takeaways from CRO's AI governance training and explains why the risk of AI isn't the AI itself. Your host is Kip Boyle, CISO
EP 211: What Sea-Tac’s Ransomware Revealed
EP 211: What Sea-Tac’s Ransomware Revealed Jun 2, 2026 00:47:05 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 question to ask after a major incident? Let’s find out with our guest Stephanie Warren, Assistant Director of Information Security at the Port of Seattle, wh
EP 210: How Boards of Directors Are Thinking About Generative AI
EP 210: How Boards of Directors Are Thinking About Generative AI May 19, 2026 00:46:18 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 Pegueros, former CISO at Docusign and U.S. Bank, and current board member at LivePerson and BECU. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, an
EP 209: Mythos: When AI Finds More Than We Can Fix
EP 209: Mythos: When AI Finds More Than We Can Fix May 5, 2026 00:52:31 Anthropic released Claude Mythos Preview. The headline is "AI can now find zero-days." Yes, but the real story is the gap between what AI finds and what organizations can fix. About 99 percent of Mythos findings are still unpatched. We cover what Mythos is in plain English, why the patching gap matters most, what duty of care means when your board knows these tools exist, where AIR-MAP fits,

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