Adventures of Alice & Bob

In this episode, James sits down with Tim Chase, Principal Technical Evangelist at Orca Security and 20-year cybersecurity veteran. He shares stories from his early days: learning from "Hacking Exposed" books at Barnes & Noble, getting caught with hacking tools an hour after installing them, and how dropping out of college after designing one trebuchet led him from functional testing to CISO roles.But Tim isn't dwelling on the past. He reveals the nation state that manipulated open source binaries because diplomatic channels failed, explains why security awareness training is fundamentally broken, and demonstrates why AI will actually favor defenders over attackers—a refreshingly optimistic take. From acronym overload to the "Negative Nelly" problem, Tim shows why cybersecurity desperately needs a positive mindset shift.

In this episode, James sits down with Silas Cutler, Principal Security Researcher at Census and founding member of Oni Scans, to explore his unconventional journey through threat intelligence and malware analysis. What happens when your first day as a SOC analyst takes down a Fortune 500 company—and Anonymous gets the credit?

From accidentally causing international headlines to going undercover in ransomware gangs, Silas has built a career on creative problem-solving and community building. He's become Facebook friends with hackers he investigates, created Malshare (a community malware repository), and founded B-Sides Pyongyang—a security conference celebrating "Missile Industry Day" that started as a joke but attracted 490 attendees.

In this episode, James and Marc sit down with Aaron Portnoy, Head of Research at MindGuard and founder of Pwn2Own.He shares stories from his early days: learning exploitation from anonymous IRC hackers, getting visits from both the IRS and FBI, a chance meeting with HD Moore at a party, and how his ability to reverse engineer fast led him to become the youngest manager at Zero Day Initiative where he helped create the Pwn2Own competition.

But Aaron isn't living in the past. He reveals how he found a persistent RCE in Google's brand-new Anitgravity IDE within its first 24 hours, explains why AI security is fundamentally broken, and demonstrates how AI agents become insider threats that enterprises can't control or understand. From six-hour firewall exploits to decimal IP bypasses, Aaron shows why the attack surface has become "literally endless."

In this episode, James Maude sits down with Chris Neuwirth, VP of Cyber Risk at Networks Group, whose path into cybersecurity might be the most unconventional you'll ever hear—from delivering babies as a teenage EMT to penetration testing critical infrastructure today.

Chris's journey includes serving as an LAPD officer at Venice Beach, responding to 9/11 at the Pentagon, managing IT during Hurricane Sandy, and running operations as assistant commissioner at New Jersey's Department of Health during COVID-19. Along the way, he's been hacking everything he could get his hands on—from war driving through Manhattan in the early 2000s to conducting sophisticated penetration tests at hospitals and airports today.

Chris discusses the importance of organizations being prepared and shares the uncomfortable truth: sometimes the easiest way past your defenses is just showing up and plugging in.

In this episode, James talks to Charles Herring about what happens when an IT wizard runs away to join the Navy, works on fighter jets, and then gets thrown into cybersecurity right after 9/11? He shares his unconventional journey from the Wild West days of network defense—complete with fighting worms with worms—to being CISO during the Target breach. Plus: why trauma creates silos, why your SOC is like throwing receipts in garbage bags, and what it takes to build a "good neighborhood" in cybersecurity.