Adventures of Alice & Bob
Welcome to the Adventures of Alice & Bob Podcast, where we talk shop with pen testers, hackers, and the unsung heroes of the cybersecurity world about the human element of being on the front lines of cyber attacks. Produced by Merchants Media. For booking inquires, email booking@merchantsmedia.com
Episodes
BeyondTrust's 2025 Microsoft Vulnerability Report dropped—and it’s a wake-up call. With 1,360 new vulnerabilities and elevation of privilege attacks dominating the landscape, even insurance companies are backing away from covering privileged service accounts. In this special episode, cybersecurity veterans James Maude, Paula Januszkiewicz, Sami Laiho, Kip Boyle, and Charles Henderson dig into what the data from the 2025 report real...
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June 20, 2025 • 57 mins
In today’s episode, James Maude chats with Robin Wood—better known as “DigiNinja”—the creator of DVWA and co-founder of SteelCon. Robin shares wild stories from his hacking career, including an infamous SQL injection that accidentally overwrote every customer’s credit card info on a gambling site, how he took down entire client networks with just two packets, and the origins of the UK’s most eccentric security conference, SteelCon—...
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In today's episode, James Maude dives into the world of cyber warfare, espionage, and hacked satellites with the legendary Chris Kubecka—aka the "Chief Hacktress." From grounding overconfident pilots as one of the first female C-5 loadmasters, to investigating mysterious “vampire satellites” that silently disable spacecraft, Chris has lived a life straight out of a cyber-thriller.
She recounts her front-line role in the aftermat...
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May 23, 2025 • 48 mins
In this episode, host James Maude sits down with Runa Sandvik, a cybersecurity pioneer protecting journalists and vulnerable populations worldwide. From hacking wi-fi enabled rifles to creating secure tip systems for The New York Times, Runa shares the fascinating journey that led her from Norway's tight-knit tech scene to the frontlines of digital security.
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May 12, 2025 • 64 mins
In this episode, cybersecurity veteran, Kymberlee Price joins James and Marc for a riveting conversation that traces her unconventional path from public health to becoming a pioneering force at Microsoft Security. Kymberlee opens up about her classified work tracking down the creators of the infamous Zotob worm, and how that experience helped reshape how companies collaborate with security researchers. With clarity and candor, she ...
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April 25, 2025 • 52 mins
In this episode, James Maude chats with industrial cybersecurity expert Lesley Carhart (aka "Hacks for Pancakes"), whose journey from programming on her family farm to protecting critical infrastructure was shaped by curiosity and determination. Lesley reveals how moths accidentally activating a power plant touchscreen led to a late-night "Chinese hackers" investigation, explains why she carries a "marriage counseling" sign when me...
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April 11, 2025 • 58 mins
In this episode, James Maude chats with cyber threat intel pro Brian Kime, whose journey from the Army’s infamous “chemical guy” to security expert was partly inspired by Starship Troopers. Brian dishes on his legendary Dell SecureWorks phishing op that hit a wild 50% click rate—by predicting an IPO years ahead of time. He also unpacks why vulnerability management can stall business and how design thinking can reshape threat intel.
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March 28, 2025 • 53 mins
James Maude chats with Roger Grimes, a 36-year cyber veteran and KnowBe4’s Defense Evangelist. From hacking DOS viruses for John McAfee to catching Chinese APT hackers red-handed, Roger’s war stories are unforgettable. But he’s not just here for the drama—he lays out a bold plan to fix Internet security and reveals why social engineering remains our biggest blind spot. Don't miss this episode—it's a masterclass in cyber warfare, de...
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March 14, 2025 • 53 mins
In this episode, James sits down with Sounil Yu, the mind behind the Cyber Defense Matrix and DIE Triad frameworks that have transformed how organizations approach security. From his early days getting stuffed in lockers as a self-described computer geek to becoming a disruptive force at Bank of America and co-founding Gnostic, Sounil shares the mental models that have guided his three-decade journey in cybersecurity. They discuss ...
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February 28, 2025 • 55 mins
In this episode, James chats with Richard Stiennon—cybersecurity analyst, author, and former aerospace engineer—whose 20+ year journey spans from designing car seats to hacking corporate systems for giants like Dell. Hear how a 1992 magazine article led him to launch his own ISP and rise to prominence at Gartner. Richard shares his personal stories from the frontlines of cybersecurity, his crusade against risk management jargon, an...
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February 14, 2025 • 54 mins
Step into the fascinating mind of Keren Elazari—the first Israeli woman to give a TED Talk and a trailblazing force in cybersecurity. Once rejected by her school’s D&D group, she defied expectations to become a globally recognized security analyst, reshaping the narrative around hackers.
In this episode, we dive into Keren’s remarkable journey—from a curious young girl armed with an encyclopedia and inspired by the movie Hackers t...
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January 31, 2025 • 71 mins
In this episode, James sits down with Tommy DeVoss (aka Doggy G), who went from a teenage hacker dodging federal prison to becoming one of the most successful ethical hackers in the world. Tommy spills raw, unfiltered stories about his wild days in IRC channels, running with the infamous World of Hell hacking group, and somehow managing to turn his life around to rake in over $4 million in bug bounties. You'll hear how a 10-year co...
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January 17, 2025 • 52 mins
Join James as he sits down with Mishaal Khan, a seasoned cybersecurity expert with over 20 years of experience in outsmarting attackers. From his early days hacking PC games to his current mission of safeguarding high-profile individuals, Mishaal offers fascinating insights into the world of open-source intelligence (OSINT) and social engineering. Discover how he’s intentionally erased his digital footprint, including keeping his o...
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January 3, 2025 • 53 mins
Today, James Maude sits down with Dustin Haywood, better known as Evil Mog, Executive Managing Hacker at IBM's X-Force. Together, they talk about Evil Mog's fascinating journey from telemarketing to becoming a globally recognized expert in password security. He shares stories, including how he managed a high-stakes data center crisis, creatively navigated IBM's corporate culture through social engineering, and transformed the lands...
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December 20, 2024 • 53 mins
Join hosts James Maude and Marc Maiffret as they dive into a captivating conversation with industry legend Morey Haber. With over two decades of experience—going back before CVEs were even a thing—Morey delivers a bold look at the security threats of 2025 and beyond. Is AI on the verge of bursting its hype bubble? Are hidden paths to privilege the next battleground? The group discusses how today’s identity-based attacks are reshapi...
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December 6, 2024 • 51 mins
Join host James Maude as he talks all things cryptography with Sophie Schmieg, a Staff Information Security Engineer at Google. In this episode, Sophie shares her journey from pure mathematics to applied cryptography, revealing how her background in algebraic geometry provides a distinctive approach to modern security challenges. From discovering major vulnerabilities in AWS to creating solutions that will last until the year 909,0...
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November 22, 2024 • 48 mins
Today, Marc and James welcome Brooke Denney, a rising star in cybersecurity who brings a dynamic, cloud-first perspective to the ever-evolving industry. Brooke shares her inspiring journey from aspiring veterinarian to accomplished security engineer, offering insights into the fascinating world of AI-powered phishing, modern security challenges, and safeguarding critical infrastructure. As a senior information security engineer and...
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November 8, 2024 • 60 mins
In this episode, Marc and James plunge into the world of identity security with DJ Morimanno. From his early days pf dumpster diving for computer parts to becoming a powerhouse Director of Identity and Access Management Technologies, DJ’s cybersecurity journey is what legends are made of. They dig deep into the evolution of identity security, the pivotal role of human behavior in staying cyber-safe, and how quantum computing could ...
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October 18, 2024 • 53 mins
In today's episode, host James welcomes Anna Aslanishvili, the visionary founder and CEO of Pine Risk Management. Anna takes us behind the scenes of high-stakes security assessments, from testing executive protection during a CEO's morning jog to uncovering faulty panic buttons—and even dealing with the threat of mailed anthrax. With captivating stories and expert insights, Anna reveals how pushing the limits in real-world scenario...
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October 4, 2024 • 52 mins
Today, Marc and James have the pleasure of sitting down with Omar Aviles, a seasoned expert in DFIR, threat hunting, and malware analysis. Omar takes us on a journey through his early days of dismantling computers out of sheer curiosity to the high-stakes world of battling ransomware in real-time. He delves into the growing dangers of corporate espionage, nation-state attacks, and the ever-evolving landscape of cybersecurity. Throu...
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