Adventures of Alice & Bob

In this episode, James talks to Mark Kreitzman, Chief Cyber Evangelist at Afani and host of the Afani Features podcast, whose thirty year career took him from typing BASIC games into an Apple II to building the email and web security platforms later acquired by Microsoft and Cisco. He shares the story of an email administrator whose t shirt read gave a glimpse into how much power sat behind old email filtering systems long before spam filters moved to the cloud. Mark then walks through the night in 2018 when his phone went dead in the middle of the Arizona desert, the start of a sim swap attack that drained his Bitcoin and hijacked his accounts in just sixty one minutes. He describes socially engineering a carrier employee into revealing who was behind it, and how that ordeal pushed him to co found Afani, a mobile carrier built around preventing sim swapping attacks.

In this episode, James talks to Co-host Marc Maiffret, and Dennis Fisher of Decipher, to mark the 25th anniversary of the Code Red worm, one of the most consequential moments in cybersecurity history. Marc takes us back to the Friday night he and his friend and co-worker Ryan Permeh were playing Tony Hawk Pro Skater when two customer emails changed everything, leading them to discover a self-propagating worm spreading at 2,000 servers per minute and ultimately landing Marc on a call with the White House situation room and in front of Congress.

Together the three of them dig into what Code Red revealed about the state of security in 2001, from the near total absence of patch management to vendors handling vulnerability disclosures through their marketing departments, and why Marc told Congress at the time that the worm was one of the best things that could have happened to the industry. The conversation draws a striking parallel to today, as AI is compressing the vulnerability exploitation window in ways that mirror the chaos of the early internet era, and Marc warns that the industry is drifting back toward insecure by default, the exact mistake that made Code Red possible in the first place.

In this episode, James sits down with Brent White and Tim Roberts, senior principal security consultants and covert entry specialists at Dark Wolf Solutions. They trace a remarkable journey together from teenage hijinks exploring phone phreaking, bump keys and IRC channels in the early 90s to running full-spectrum physical red team operations against some of the most secure government facilities in the world.

Along the way they share the lessons and common mistakes for anyone entering the field, drawn from years of hard-won experience, alongside some unforgettable stories. That includes a creative attempt to infiltrate a facility using a stray cat, the covert card-cloning clipboard they use to lift staff RFID badges in plain sight, and the unique challenge of explaining "weaponized cat" in a report destined for high-ranking officials. They also open up about their quieter work, volunteering to help law enforcement disrupt human trafficking rings and online predators, something they have been doing since they were teenagers.

In this episode James talks to Robert Siciliano, certified speaking professional, bestselling author, private investigator, and creator of the Strategic Human Firewall. A man whose introduction to adversaries didn't come from a classroom but from being beat up in Boston aged 12. He has spent the 35 years since delivering the same uncomfortable truth, the biggest vulnerability in any system isn't the technology, it's the human trusting by default on the other side of the screen.Together they break down why phishing simulation training can cause a compliance trap that makes CISOs feel safe while leaving employees completely exposed, what the "human blind spot" is and why organized crime understands your psychology better than you do. Robert describes how AI has quietly turned pig butchering scams into the most lucrative fraud operation in human history. Taking us inside his personal undercover conversations with scammers, a deepfake video call with a woman named "Gloria," and the devastating real-world cost of these crimes that can cost people everything.

In this episode, James Maude sits down with Jeffrey Wheatman, SVP and Cyber Risk Strategist at Black Kite and former 16-year Gartner VP, whose career started not in a SOC, but behind the counter of a hardware store in New York City. A stack of 2,600 magazines and a Novell NetWare training course later, he found himself in IT but quickly realized there was more than technology involved in security, there was a story to be told.

In his career Jeffrey has coached nearly 500 CISOs on how to walk into a boardroom and actually be heard. Jeffrey explains why Hans Christian Andersen fairy tales make better security training tools than most vendor decks, why your choice of words might be quietly killing your credibility. He also discusses why AI isn't just a threat, it's an imperfect storm that is already tearing through your supply chain whether you're watching it or not.