Cyber Risk Management Podcast

Hosted by Kip Boyle

Business Management Technology

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Episodes

216

Latest episode

Aug 2026

Language

EN-US

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.

Listen to episodes

60 recent

August 11, 2026Episode 21653 min

EP 216: When Reasonable Beats Bankrupt

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 company spent its money on cybersecurity, not fines. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates. LinkedIn: https://www.linkedin.com/in/chris-cronin-351416/ "Fire Doesn't Innovate" by Kip Boyle: https://a.co/d/0bYatohy Learn more about DoCRA: https://docra.org

July 28, 2026Episode 21551 min

EP 215: Is Your AI Strategy a Risk Decision in Disguise?

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. So, which controls are we turning off to get this speed, and are we allowed to? Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates. Y Combinator's AI native playbook video -- https://youtu.be/B246K_G7mHU AIR-MAP website -- https://air-map.io/

July 14, 2026Episode 21439 min

EP 214: AI Agents Don't Behave Like Humans

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 works at the front edge of how machines get access to systems. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates. LinkedIn profile profile: https://www.linkedin.com/in/wangnancy/ 1Password: https://1password.com/

June 30, 2026Episode 21347 min

EP 213: The Group Writing the Rules for AI Trust

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 can do, and walks through the tools his team built so you can adopt AI without guessing. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates. Cloud Security Alliance: https://cloudsecurityalliance.org/

June 16, 2026Episode 21247 min

EP 212: The AI Worked. The Process Didn't.

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 with Cyber Risk Opportunities. Subscribe to Inflection Point -- https://cr-map.com/inflectionpoint/ SecureWorld AI Security PLUS course -- https://www.secureworld.io/events "Gears Don’t Guess: The Executive’s Practical Guide to Thriving in the Face of AI Hype and Risk" (forthcoming book, Fall 2026) AIR-MAP AI Risk Assessment -- https://air-map.io

June 2, 2026Episode 21147 min

EP 211: What Sea-Tac’s Ransomware Revealed

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, who lived through that attack and came out the other side with hard-won lessons about executive decision-making under pressure. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates. LinkedIn profile – https://www.linkedin.com/in/stephanie-warren-0746343/

May 19, 2026Episode 21046 min

EP 210: How Boards of Directors Are Thinking About Generative AI

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, and Jake Bernstein, Partner with K&L Gates. LinkedIn profile – https://www.linkedin.com/in/vanessapegueros Website – https://vanessapegueros.com

May 5, 2026Episode 20952 min

EP 209: Mythos: When AI Finds More Than We Can Fix

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, and why most advisors skip data sovereignty. Hosts: Kip Boyle, CISO, Cyber Risk Opportunities; Jake Bernstein, Partner, K&L Gates. Anthropic Claude Mythos Preview https://red.anthropic.com/2026/mythos-preview/ AISLE / Stanislav Fort, "AI Cybersecurity After Mythos: The Jagged Frontier" https://aisle.com/blog/ai-cybersecurity-after-mythos-the-jagged-frontier AIR-MAP overview https://air-map.io/

April 21, 2026Episode 20852 min

EP 208: Flan Recipes and Prompt Injection

A Stripe employee hid a message in his LinkedIn profile telling any AI that read it to include a flan recipe. A month later, an AI recruiter emailed him one. It's funny until you realize the same technique can exfiltrate data, generate phishing content, or hijack automated business processes. What is prompt injection, why does OWASP rank it as the number one risk to large language models, and what should you do about it? Let's find out. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates. OWASP Top 10 for LLM Applications -- https://genai.owasp.org

April 7, 2026Episode 20745 min

EP 207: Defend the Business from Cybersecurity

What happens when a cybersecurity team designs controls without asking the business what they need? And what role exists specifically to prevent that? Let's find out with our guests Brian Shea and Maggie Amato, former Business Information Security Officers at Salesforce. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates. Brian Shea's LinkedIn profile -- https://www.linkedin.com/in/brianshea/ Maggie Amato's LinkedIn profile -- https://www.linkedin.com/in/maggie-amato-021624164/