Adventures of Alice & Bob

• 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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• Ep. 88 - Microsoft Tried to Get Me Fired Weekly // HD Moore

  James sits down with cybersecurity pioneer HD Moore, the legendary founder of the Metasploit framework, whose journey from dumpster-diving teenager to cybersecurity pioneer was anything but easy.   HD recounts how Microsoft called his employer weekly trying to get him fired for releasing exploits — harassment that ultimately motivated him to "drop zero days continuously, forever, until it got normal." He shares tales of accidentally controlling satellite systems after following network hops too far, backdooring 7,000 systems through tainted warez, and spending $80,000 on his personal credit card to build the Rapid7 team when traditional corporate processes moved too slowly. From crawling through school windows at 5 AM to access Apple computers as a poor kid, to discovering that Palo Alto devices were leaking 5,000 customers' domain admin passwords to internet scanners, HD's stories illuminate the wild early days when vulnerability research was considered criminal activity rather than corporate necessity. Discover how he accidently destroyed his first self-built computer, why his ex-wife held a pile of cash as bail money ready during years of FBI visits, and how the Phrack IRC channel became an unlikely recruitment ground for his first cybersecurity job.

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• Ep. 87 - Code Crashes and Vinyl Scratches // Kevin Greene

  In this episode, James Maude sits down with Kevin E. Green, Chief Security Strategist at BeyondTrust, whose 25+ year career stretches from configuring Nokia firewalls in basements to shaping federal research initiatives. Kevin recalls how crashing systems during penetration tests at Ernst & Young was once considered a win - a “capture the flag” moment - and how he crossed paths with future industry leaders like Stuart McClure and George Kurtz, who went on to found Cylance. He shares his pivotal work in mapping NIST 800-53 controls to the MITRE ATT&CK framework, transforming static security catalogs into threat-informed heat maps that show which defenses light up against real-world attacks. Blending technical depth with cultural insight, Kevin also draws unexpected parallels between cybersecurity and hip-hop — from how attacker techniques echo rapper “signatures” to why his alter ego "Kevtorious" and his "Secure Coding by Nature" brand reflect the creativity and pattern recognition needed in both fields.

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