Cybersecurity has survived cloud, mobile, and a dozen other "biggest disruptions of our lifetime," and each one felt unprecedented in the moment. In this episode, Ron sits down with Alyssa "Dr. Jay" Abdullah, Deputy CISO at MasterCard, who started her career as a radio DJ and has since worked inside the White House, Lockheed Martin, Stryker, and Xerox before landing in payments security.

Ron and Dr. Jay trace her path from spinning records to securing global payment infrastructure, and dig into why she'd argue cloud, not AI, was the real turning point in her career. They cover what convergence actually looks like when AI, cloud, and synthetic identity start overlapping, why curiosity matters more than fast answers, and what it means when employees start bringing their own trained AI agents to work.

The conversation closes on something most teams haven't fully reckoned with yet: AI agents that carry their own identity, independent of the humans who built them, and what that shift demands from the people responsible for securing them.

Impactful Moments

00:00 - Introduction 02:25 - Busting the AI hype myth 04:40 - From radio DJ to Dr. Jay 06:10 - A day in the life as Deputy CISO at Mastercard 07:25 - Why AI hasn't disrupted her world 08:50 - White House tech through the decades 12:30 - Smartphones, wearables, and what's next 13:30 - Defining convergence for 2026 14:50 - When AI meets quantum computing 17:20 - Bring your own AI agent to work 19:00 - Negotiating salary in tokens 21:05 - Teaching curiosity over answers 23:50 - Overhype equals overtrust 27:10 - The future of tier one and autonomous SOC 29:50 - Hot take: AI in the SOC 31:35 - Predictions: AI identities and the human outside the loop

Links

Connect with Alissa "Dr. Jay" Abdullah on LinkedIn: https://www.linkedin.com/in/dralissajay/

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Security teams spent decades begging for more logs. Now the enterprise is generating petabytes a day, and the thing drowning in it isn't just the SOC anymore, it's your AI agents too. In this episode, Ron sits down with Myke Lyons, CISO at Cribl, who cut his teeth in telemetry and logging decades ago and has landed right back there in the age of AI.

Ron and Myke dig into why most telemetry failures aren't data problems at all, they're decisions nobody made about why the logs are being collected in the first place. Myke breaks down what to track on every agent in your environment, why token spend belongs on the security team's plate, why dashboards are quietly dying, and why treating an AI agent like just another employee is a mistake that's going to bite security teams hard.

Underneath it all is one question Myke keeps circling back to: do you actually know what normal looks like for every agent in your environment?

Impactful Moments

00:00 - Introduction 01:50 - Myth Busting: AI Agents Aren't Just Another User Account 04:25 - Meet Myke Lyons, CISO at Cribl 05:05 - What it means to run security at a telemetry company 06:10 - From gigabytes of logs at GE to petabytes today 07:45 - MITRE ATT&CK, Cribl's new APEX framework, and orienting telemetry 10:20 - Why most telemetry problems are decision problems, not data problems 13:20 - OCSF and how security teams are rethinking their schemas 14:25 - Why the dashboard is dying 17:35 - What Myke wants to track about every AI agent 20:10 - How to spot an agent going rogue 23:15 - Making your data AI-ready and the case for schematizing everything 27:10 - Tokenomics: treating AI spend as a security responsibility 29:05 - The non-negotiable logs every org should be collecting 31:50 - Hot takes: build vs. buy, tier two to three, and Myke's daily AI briefing 33:35 - Closing thoughts and outro

Links

Connect with Myke Lyons on LinkedIn: https://www.linkedin.com/in/mykelyons/

Learn more about Cribl: https://cribl.io/

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A year ago, the average employee held about 30 OAuth grants. Today that number has risen to 88, and it isn't slowing down. Ron sits down with Russell Spitler, co-founder and CEO of Nudge Security, and Richard Penshorn, a senior security engineer at a top financial services company, to talk about the AI already living inside your business.

Ron, Russell, and Richard dig into why shadow AI doesn't behave like shadow IT, how one forgotten grant became the door into a real world breach, and whether AI agents should ever get access to a corporate inbox.

Underneath all of it is the one thing Russell and Richard keep coming back to: ownership. Give an AI agent access with no owner attached and it becomes invisible. Give every employee an approved, low-friction path to use AI and they stop wandering off it. Find out how you can get ahead of the AI already running inside your walls.

Impactful Moments

00:00 - Introduction 02:00 - Busting the "shadow AI is just shadow IT" myth 03:45 - Meet Russell Spitler and Richard Penshorn 05:50 - The surprising long tail of AI tool usage 07:00 - Entertainment vs. finance: build vs. buy culture 08:50 - How 30 OAuth grants became 88 in 2026 10:25 - Why manual OAuth audits became untenable 11:30 - The Canva example: what "click to connect" really grants 15:20 - Benign vs. malicious: how a stolen OAuth grant gets exploited 17:00 - Shadow IT vs. Shadow AI: what's actually different now 21:00 - Hot take: should AI agents ever touch corporate email? 25:10 - The three buckets of AI agent discovery 27:55 - Russell's best practices for locking down agents 31:00 - Fundamentals for the next 18 months: visibility and easy paths

Links

Connect with Russell Spitler on LinkedIn: https://www.linkedin.com/in/russell-spitler/

Connect with Richard Penshorn on LinkedIn: https://www.linkedin.com/in/richardpenshorn/

Learn more about Nudge Security: https://www.nudgesecurity.com/

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