Adventures of Alice & Bob

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.

In this special milestone episode of Adventures of Alice & Bob, hosts James Maude and Marc Maiffret take a rare step back from interviews and headlines to celebrate reaching 100 episodes! From the accidental move that launched the podcast before Marc had even agreed to do it, to the guests whose stories stopped them cold - this episode is a love letter to the human side of cybersecurity and all of the great guests who have come on to share their stories.

Marc and James are also joined for the first time on camera by the man who has silently made every episode possible: super producer Jesse Shirley. Expect honest reflections, genuine laughs, podcast highlights, and what's next for Adventures of Alice & Bob.

In this episode, James Maude sits down with Rob Black, founder and CEO of Fractional CISO, who started his career at RSA Security and had a front-row seat to one of the most consequential breaches in cybersecurity history, all while his wife was going into labor with their first child.

From inventing patents at RSA to starting a one-man LinkedIn crusade against "SOC 2 in two weeks" scams, Rob's stories are equal parts entertaining and infuriating. He explains why compliance theater is actively making companies less secure, why your CEO needs to hear things with a dollar value, and why you should think about cybersecurity less like an asteroid and more like a roulette wheel. Plus, why the "Lexus of Fractional CISOs" doesn't own a single IoT device.