Home Podcasts Cyber Risk Management Podcast
Cyber Risk Management Podcast

Cyber Risk Management Podcast

Kip Boyle 211 Episodes Jun 16, 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 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 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 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 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,
EP 208: Flan Recipes and Prompt Injection Apr 21, 2026 00:52:39 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
EP 207: Defend the Business from Cybersecurity Apr 7, 2026 00:45:16 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 She
EP 206: Fire Doesn't Innovate. AI Does. Are You Ready? Mar 24, 2026 00:31:30 Fire hasn't changed since the dawn of humanity, but our cyber adversaries evolve every single day. What happens when organizations spend $10 on AI transformation for every $1 on cybersecurity? In this special ROCon 2025 keynote replay, Kip shares two stories that changed how he thinks about risk: a "perfect" employee who became an insider threat in four weeks, and a $12M deepfake that defeate
EP 205: Making Privacy Compliance Sustainable Mar 10, 2026 00:42:02 Privacy laws keep multiplying, regulations keep changing, and AI is making everything more complex. How do businesses build privacy compliance that actually sticks instead of just checking a box? Let's find out with our guest Jordan Fischer, Founder and Partner at Fischer Law and Cybersecurity Lecturer at UC Berkeley. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bern
EP 204: Carpets and Diamonds Feb 24, 2026 00:50:05 Most cybersecurity people talk at CFOs instead of with them. What if there were a simple test to know when a CFO wants to learn about cyber risk versus when they just need someone to trust? Let's find out with our guest James Wheeler, a highly experienced CFO who now runs kept.pro, providing fractional accounting teams to businesses across the country. Your hosts are Kip Boyle, CISO with Cybe
EP 203: Cyber Risk Quantification Feb 10, 2026 00:48:31 Can cyber risk actually be measured in dollars? How do you know if your risk data vendor is any good? And is cyber insurance really worth the investment? Let's find out with our guest Scott Stransky, who leads the Cyber Risk Intelligence Center at Marsh and was named 2023 Cyber Risk Industry Person of the Year. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein,
EP 202: Why Fortune 500s Still Run on Windows 2003 Jan 27, 2026 00:38:15 Why do IT organizations cling to ancient technology like Windows 2003, creating dangerous technical debt they don't even recognize? And how do they get out of this trap? Let's find out with our guest Anton Chuvakin, who advises the biggest customers of Google's Cloud services. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.   Lin
EP 201: AI Powered Espionage Jan 13, 2026 00:44:51 AI-driven attacks aren't coming; they're here. A Chinese state-sponsored group just ran cyber espionage operations that were 80 to 90 percent autonomous. What does this means for defenders? Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.   Here's Anthropic's report -- https://www.anthropic.com/news/disrupting-AI-espionage  

Recommended