Adventures of Alice & Bob

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.

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.

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.

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.

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.

In this episode, James Maude sits down with Brian Wagner, CTO at Revenir, whose cybersecurity story started at just 15, building Microsoft Access databases for a medical hospice. From teenage entrepreneur to AWS security specialist, Brian’s path has been anything but ordinary. He pulls back the curtain on his time with the elite Zipline incident response team where he confronted a catastrophic VPC peering breach that spiraled into data theft and blackmail. Together, James and Brian dissect how vendor network compromises can silently open doors into your cloud and why Brian insists that true security isn’t something you bolt on later - it’s a culture you build from day one.

Join host James Maude for a candid conversation with Matthew Toussaint - founder of Open Security and mastermind behind the legendary Subterfuge framework that once forced Starbucks to overhaul its Wi-Fi security. From his unexpected path as an aspiring Air Force lawyer to becoming a renowned cybersecurity educator, Matthew shares a lifetime of stories: a physical pen test that went spectacularly wrong at a franchise location, a medical clinic investigation that exposed an insider threat with international stakes, and how old-school phone-based social engineering works in the age of identity threats. They dive into why AI is about to make help desk social engineering terrifyingly scalable, how a nervous 21-year-old’s DefCon talk reshaped network security, and why, despite decades of warnings, the industry is still failing at the basics while attackers rapidly scale with artificial intelligence.

Former FBI Supervisory Special Agent Miguel Clarke joins hosts James Maude and Marc Maiffret to reflect on 25 years at the front lines of cybersecurity. From coding in BASIC on his Commodore 64 to helping uncover the digital trail behind 9/11, Miguel shares raw, behind-the-scenes stories of how real cyber investigations unfold. In this episode, you'll hear how a casual beer in Nebraska sparked a career in federal law enforcement, why psychology plays a critical role in executing search warrants, and how early cyber sleuths tracked international hackers with nothing but screen scrapes and UUencoded files. Miguel also takes us deep inside the Swedish secret police operation that caught the infamous Csaba Richter hacker, explores the rise of Eastern Europe’s cybercrime economy, and breaks down the forensic breakthroughs that helped investigators piece together one of the most pivotal events in modern history. 00:00 - Introduction and Welcome 01:32 - Early Technology Interest with Commodore Computers 03:24 - System Shock and the $2,100 Computer Upgrade Nightmare 05:22 - Gaming Influence on Career Path and FBI Power Dynamics 06:42 - The Beer That Started an FBI Career 10:03 - FBI Training and Imposter Syndrome at Quantico 14:11 - Sales Skills Meet FBI Investigation Work 18:04 - Search Warrant Psychology and Family Dynamics 24:08 - The Chaba Richter International Cyber Case 27:38 - Eastern European Cybercrime Economy Theory 31:51 - Evolution from Website Defacements to Nation-State Attacks 36:24 - Digital Aspects of 9/11 Investigation 42:25 - 9/11 Digital Forensics and HTML Tag Discovery 47:56 - Transition from FBI to Private Sector 51:32 - Leadership Philosophy and Closing Thoughts

Tommy DeVoss—aka "dawgyg"—is back for round two, and it’s even wilder. A former black hat who faced prison four times, Tommy turned his life around and became a legend in the bug bounty world. From max-sec prison cells to flexing a championship belt on stage at HackerOne Live, his story is pure hacker folklore. In this episode, he shares how bug bounties bought him mini donkeys, why he still hunts old-school (no tools, no scripts), and how federal judges, rogue AIs, and childhood IRC wars shaped his chaotic path. Expect redemption arcs, sketchy bets, and a surprise detour into Icelandic youth basketball.