Adventures of Alice & Bob

• Ep. 93 - From Pwn2Own to Pwning AI // Aaron Portnoy

  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."

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• Ep. 92 – Births, Badges, and Breaches // Chris Neuwirth

  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.

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• Ep. 91 - Inside the Target Breach War Room // Charles Herring

  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.

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• Ep. 90 - The History of L0pht : The Winnebago Incident and Testifying Before Congress // Chris Wysopal

  In this episode, we sit down with Chris Wysopal (aka Weld Pond), co-founder of the legendary L0pht Heavy Industries and CTO/co-founder of Veracode. Chris takes us on a journey from programming BASIC on cassette tapes in the 1970s, through the golden age of BBS culture and phreaking, to testifying before the U.S. Senate as one of the first hackers to bring security concerns to Capitol Hill. You'll hear the untold story of an early penetration test gone spectacularly right—involving command injection, a manhole fire, voicemail hacking, and one very confused executive wondering why hackers wanted a Winnebago. Chris shares what it was like building the first hacker space in America, the challenges of turning hacking from hobby to business, and why creating a new security category took over a decade.

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• Ep.89 - The Hollywood Hacker: Album Leaks and NSA Whistleblowers // Ralph Echemendia

  In this episode, James Maude talks with Ralph Echemendia “the ethical hacker” whose journey from Miami phone phreak to Hollywood’s top cybersecurity consultant is stranger than fiction. Ralph shares how hacking printers and hospital records jump-started his career, why tracking down an Eminem album leak turned into an international manhunt, and what Oliver Stone learned about the NSA at DEF CON. From securing the Snowden film against nation-state attacks to uncovering that studios store entire movies in Dropbox, Ralph exposes Hollywood’s biggest security blind spots and the rise of AI-powered deepfake heists worth hundreds of millions.

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