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Kip Boyle · Technology

Cyber Risk Management Podcast

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.

Episodes

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EP 220: Every AI Agent Needs Its Own Name

06 Oct 2026
50m
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Artificial intelligence disrupts traditional cybersecurity by replacing deterministic systems—which rely on predictable rules—with probabilistic models that lack clear, traceable logic. This shift creates a critical vulnerability where control and data planes are inextricably mixed, turning standard threats into comple...

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EP 219: Why Gears Don't Guess

22 Sep 2026
52m
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EP 218: The “Compliance Hammer” Alternative (REPLAY)

08 Sep 2026
45m
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EP 217: When Hospital Systems Go Down, Who Keeps Patients Safe?

25 Aug 2026
48m
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EP 216: When Reasonable Beats Bankrupt

11 Aug 2026
53m
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EP 215: Is Your AI Strategy a Risk Decision in Disguise?

28 Jul 2026
51m
AI processed

The "AI-native" business playbook promoted by Y Combinator offers significant productivity gains by centralizing organizational data and enabling broad access for AI agents, yet it fundamentally conflicts with core cybersecurity and legal governance principles. Implementing this model requires recording all communicati...

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EP 214: AI Agents Don't Behave Like Humans

14 Jul 2026
39m
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EP 213: The Group Writing the Rules for AI Trust

30 Jun 2026
47m
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Generative AI is fundamentally reshaping cybersecurity, moving at a pace that dwarfs previous technological shifts like cloud computing. Jim Reavis, CEO of the Cloud Security Alliance, highlights that this transition grants attackers nation-state-level capabilities through automated vulnerability discovery and chaining...

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

16 Jun 2026
47m
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EP 211: What Sea-Tac’s Ransomware Revealed

02 Jun 2026
47m
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EP 210: How Boards of Directors Are Thinking About Generative AI

19 May 2026
46m
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EP 209: Mythos: When AI Finds More Than We Can Fix

05 May 2026
52m
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EP 208: Flan Recipes and Prompt Injection

21 Apr 2026
52m
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EP 207: Defend the Business from Cybersecurity

07 Apr 2026
45m
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EP 206: Fire Doesn't Innovate. AI Does. Are You Ready?

24 Mar 2026
31m
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EP 205: Making Privacy Compliance Sustainable

10 Mar 2026
42m
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EP 204: Carpets and Diamonds

24 Feb 2026
50m
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EP 203: Cyber Risk Quantification

10 Feb 2026
48m
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EP 202: Why Fortune 500s Still Run on Windows 2003

27 Jan 2026
38m
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EP 201: AI Powered Espionage

13 Jan 2026
44m
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