Adventures of Alice & Bob

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...

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 st...

In this episode, James Maude sits down with Dahvid Schloss, CEO of Emulated Criminals who started his career in special operations comms and pivoted into “not defense” cyber operations for the U.S. military. From painting rocks green for the military to accidentally becoming "APT Big Daddy" in industry when his red team tools were detected triggered a security alert Dahvid’s stories are both enter...

In this episode, James sits down with Pete Herzog, co-founder of ISACOM and creator of the OSSTMM — a comprehensive security control testing framework. He shares stories from his early days: hacking cigarettes vending machines to trade for access to computers, building a fake ID operation out of a college gerontology department, and social engineering his way onto the internet before most people k...

In this episode, James sits down with Brandyn Murtagh, founder of MurtaSec and top-ranked bug bounty hunter. He shares stories from his early days: learning exploitation from World of Warcraft at age 9, dropping out of college after three days, and how landing an apprenticeship at 16 led him from blue team analyst to elite penetration tester who's discovered critical flaws in banks, healthcare pro...

In this episode, James sits down with Tim Chase, Principal Technical Evangelist at Orca Security and 20-year cybersecurity veteran. He shares stories from his early days: learning from "Hacking Exposed" books at Barnes & Noble, getting caught with hacking tools an hour after installing them, and how dropping out of college after designing one trebuchet led him from functional testing to CISO roles...

In this episode, James sits down with Silas Cutler, Principal Security Researcher at Census and founding member of Oni Scans, to explore his unconventional journey through threat intelligence and malware analysis. What happens when your first day as a SOC analyst takes down a Fortune 500 company—and Anonymous gets the credit? From accidentally causing international headlines to going undercover in...

In this episode, James and Marc sit down with Aaron Portnoy, Head of Research at MindGuard and founder of Pwn2Own. He shares stories from his early days: learning exploitation from anonymous IRC hackers, getting visits from both the IRS and FBI, a chance meeting with HD Moore at a party, and how his ability to reverse engineer fast led him to become the youngest manager at Zero Day Initiative wher...

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 Hurric...

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 i...

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...

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. F...

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 norm...

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 industr...

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...

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...

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 c...

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...

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...

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 eccen...

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...

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. 

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 researc...

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...

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...