Show Notes
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.
More from Adventures of Alice & Bob
In this episode, James Maude sits down with Jeffrey Matson, CEO of SecureAuth, whose thirty year career runs from encrypting early GPS satellites for the military to building the ASICs behind deep packet inspection and leading identity security at Huawei, Juniper Networks, MistNet, and Zage Security. Jeffrey explains why AI agents create a brand new category of risk, capable of doing catastrophic damage without ever being hacked, and shares the story of a CISO whose own vibe coding executive became the company's biggest insider threat. They dig into the quiet authorization failures inside MCP servers, why identity has gone from cybersecurity's least glamorous discipline to the center of the action, and why the industry's obsession with the perimeter is finally giving way to real zero trust. Jeffrey also draws a sharp parallel between the dot com bubble and today's AI investment boom, and offers advice for anyone trying to break into cybersecurity in the age of agentic AI.
In this episode, Dennis Fisher and Madhav Nakar step in for James Maude to unpack the OpenAI and Hugging Face intrusion that rattled the security world this year. They trace how an AI agent, handed an impossible evaluation task, built its own underground message board inside a sandboxed package manager to recruit other agents for help. From there the agents found a zero day, escalated privileges, and ultimately broke into Hugging Face to find the answers they needed to pass their exam. Dennis and Madhav dig into what this bizarre chain of events means for incident response, why traditional playbooks fall apart against autonomous attackers, and why most enterprises may already have agents running loose on their networks without knowing it.
In this episode, James Maude sits down with Jane Frankland, MBE, founder of Newstart and author of the bestselling book InSecurity, whose career in cybersecurity spans nearly thirty years and began not in tech but in art and design. She shares the hard lessons learned building one of the UK's first penetration testing companies from the ground up. Reflects on how that experience shaped a book arguing that the absence of women in cybersecurity is a risk problem, not a diversity checkbox.Jane breaks down her framework, based on Maslow's hierarchy of needs, for why most security teams are chasing tools while ignoring leadership, culture and governance, and shares the surprising incompetence she has seen from seasoned practitioners in real world incident simulations. She also describes the motivation for her upcoming second book and why she believes cybersecurity has been solving the wrong problem all along.
In this episode, James Maude sits down with Ulrich Swart, cofounder and CEO of Subverted, a South African offensive security company built to make pentesting and ethical hacker training more accessible. Ulrich traces his path from tearing apart laptops as a curious kid to being handed a Raspberry Pi and a WiFi card outside a security firm's door and told to prove himself within a week. He shares the chaos of a bank engagement where their laptops vanished mid pentest, and the time he felt like a secret agent hacking in from a stairwell only to spot the security camera watching him the whole time. Find out what motivates Ulrich and his co-founder Jason and why giving back to the community is a key part of what they do.
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.