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 em...

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-propa...

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 i...

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 t...

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,...

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...