Cyber Risk Management Podcast

Kip Boyle
  • 5.0 (1)
  • Technology
  • Updated Biweekly

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.

  1. 3d ago

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

    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 the "memory hole," and what leaders should demand as proof. Paper is not the same as proof. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.   LinkedIn: https://www.linkedin.com/in/mark-yoffe-md-cissp-a9927956/   "Fire Doesn't Innovate" by Kip Boyle: https://a.co/d/0bYatohy     LinkedIn post:   Questions: Here are audience engagement questions for this episode, organized by segment:   Segment 1 – When the Hospital Goes Analog Have you ever worked through a system outage — at a hospital or anywhere else? What was the first thing that broke down?Does your organization have any setting where "no news is bad news" during downtime — where information stops coming to you and you don't immediately notice? Segment 2 – Ownership Who owns your clinical downtime workflow right now — not IT, but the clinical side? Can you name them?If your systems went down tonight, is there a single person accountable for whether patient care workflows hold up — or would people be figuring it out as they go? Segment 3 – Workability Does your downtime policy actually get used, or does it live in a binder somewhere? When did anyone last open it?What's one task your team assumes staff can improvise during downtime — that they probably can't? Segment 4 – The Memory Hole After your last outage, how confident are you that everything documented on paper actually made it into the record? Did anyone check?Has a gap in documentation during downtime ever affected a patient's care — or nearly did? Segment 5 – Leadership Oversight If your CEO asked today, "Can you show me that our clinical downtime controls actually work?" — what would you hand them?When did your organization last run a tabletop exercise specifically for clinical downtime — not just IT recovery? Closing poll question: Does your organization have a named, clinically credible owner for downtime workflows — yes, no, or "I genuinely don't know"?

  2. Aug 11

    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

  3. Jul 28

    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/

  4. Jul 14

    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/

  5. Jun 30

    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/

  6. Jun 16

    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

  7. Jun 2

    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/

  8. May 19

    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

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About

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.

Information

  • Creator
    Kip Boyle
  • Years Active
    2025 - 2026
  • Episodes
    217
  • Rating
    Clean
  • Copyright
    © 2026 Cyber Risk Opportunities
  • Show Website
    Cyber Risk Management Podcast

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