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

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/

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 defeated every technical control on the dashboard. Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Get Kip's book, "Fire Doesn't Innovate" 2nd Edition -- https://a.co/d/0bYatohy

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 Bernstein, Partner with K&L Gates.

Jordan Fischer's website: https://jordanfischerlaw.com

Shoshana Zuboff's book: https://en.wikipedia.org/wiki/The_Age_of_Surveillance_Capitalism

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 Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

LinkedIn: https://www.linkedin.com/in/jamesdavidwheeler/

"Fire Doesn't Innovate" by Kip Boyle: https://a.co/d/0bYatohy

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, Partner with K&L Gates. 

LinkedIn profile -- https://www.linkedin.com/in/scott-stransky-92659095/

Top 12 Report -- https://www.marsh.com/en/services/cyber-risk/insights/cybersecurity-signals.html                       

Marsh Cyber Risk Intelligence Center -- https://www.corporate.marsh.com/solutions/cyber-resilience/cyber-risk-intelligence-center.html  

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.

LinkedIn profile -- https://www.linkedin.com/in/chuvakin/

Podcast -- https://cloud.withgoogle.com/cloudsecurity/podcast/

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

AI can supercharge your security team. But it can also supercharge attackers. So how do you stay ahead in an AI-powered threat landscape? Let's find out in our special 200th episode! Your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.

Kip's keynote address -- https://youtu.be/DNRNbT0IaKM

"Fire Doesn’t Innovate: Thriving in the Face of Evolving Cyber Risks"

In this ROCon 2025 keynote, Kip Boyle challenges audiences to rethink how they approach modern threats in the age of AI. Using the metaphor of fire — a static risk that hasn’t changed for millennia — Kip explores how cyber adversaries are innovating daily while many organizations remain trapped in outdated mindsets. He closes with a compelling call to action: adapt like firefighters did with fire — or risk being left behind.

How has GenAI turned phishing Into a speed war? And what should we do about it? Let's find out with your hosts are Kip Boyle, CISO with Cyber Risk Opportunities, and Jake Bernstein, Partner with K&L Gates.