Phillip Wylie Show | Cybersecurity & Pentesting Podcast

The Phillip Wylie Show is a premier cybersecurity podcast and media source for offensive security professionals. Hosted by Phillip Wylie, globally recognized ethical hacking expert, keynote speaker, and co-author of The Pentester Blueprint, the show features elite red team operators, penetration testers, and security leaders sharing real-world tradecraft, advanced tactics, career strategy, and insights on AI-driven cyber threats.

Phillip Wylie Show | Cybersecurity & Pentesting Podcast is a technology podcast hosted by Phillip Wylie, with 193 episodes on record and a Required Pod Score of 84.

Phillip Wylie hosts Phillip Wylie Show | Cybersecurity & Pentesting Podcast, a technology show with 193 episodes published.

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  Episode #38

  Drones, RF, and the Hacker Mindset with Luke Canfield

  Sep 28, 202631 minS4

  Luke Canfield came up the way a lot of hardware hackers do, the geeky kid in high school everyone came to when the school's computers broke, tinkering with Windows XP and war driving with homemade Yagi antennas built out of Pringles cans. That fascination with the hardware side never left him, and today he runs Reconnaissance Drone Consulting, teaching people about a threat surface most of the security world still isn't looking at. Phillip and Luke met at KernelCon, and this conversation is a wide tour through the corners of security that live outside the usual enterprise conversation. They get into the resurgence of war driving and how a headless Kali Pi has replaced a car full of gear, why AI is reshaping RF and CTF competitions and what that means for people who still want to learn things manually, and Luke's real focus, drones as a multi-domain problem spanning the cyber, operational, and physical. From there it opens up into the stuff that makes you rethink physical security entirely, the six-week drone iteration cycle coming out of Ukraine and how much of it ends up freely available online, why the cartels have run in-house drone design teams for over a decade, prison contraband as the biggest domestic misuse case, and the simple reason nobody looks up - as Luke puts it, humans evolved to avoid being eaten by big cats, not big birds. He also shares his current build, an open source unmanned ground vehicle named Tortuga, made from two donated power wheelchairs, that's headed into Texas cattle pastures to spot parasite outbreaks with thermal imaging. ========================= Connect with Luke Canfield:LinkedIn: https://www.linkedin.com/in/luke-a-canfield/ ========================= Connect with your host, Phillip Wylie:LinkedIn: https://linkedin.com/in/phillipwylieX: https://x.com/PhillipWylieInstagram: https://www.instagram.com/phillipwylie

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  Episode #37

  From Law Degree to AI Cyber Defense with Zack Korman

  Sep 21, 202631 minS4

  Zack Korman came into cybersecurity from about as far outside the field as you can get, a UK law degree and a master's in law and finance, and he now spends his days on the AI defense problems most of the industry is still catching up to. His outsider path is exactly what makes his take on the current AI moment worth hearing. Based in Norway, Zack got into code to win an argument with a professor, worked his way up to running a media company's tech department, then spent four and a half years as CTO of an Oslo cybersecurity startup building AI phishing simulations and AI insider threat detection. That work pulled him deep into the defensive side of security and into a conviction that detection is one of the most underserved areas of the field. Phillip and Zack get into why the "thousand crap alerts" model of detection is broken, the blind spots that let obvious insider threats slip past a SOC that was never even receiving the data, and Zack's work on AI agent security, including the malicious MCP server he built to prove how completely an agent can exfiltrate a company. From there the conversation turns to the thing Zack has become known for online, pushing back on inflated AI risk claims, the fallout from the Hugging Face incident, and why so many of the loudest warnings about AI in cybersecurity are coming from people who have never worked in security. They also cover frontier versus local models, why smaller models could reshape defensive work, model guardrails and offensive testing, and Zack's straightforward advice for anyone trying to fold AI into their day to day. ========================= Connect with Zack Korman: LinkedIn: https://www.linkedin.com/in/zacharyakorman/ X: https://x.com/ZackKorman ========================= Connect with your host, Phillip Wylie: LinkedIn: https://linkedin.com/in/phillipwylie X: https://x.com/PhillipWylie Instagram: https://www.instagram.com/phillipwylie ========================= Sponsored by Suzu Labs ========================= All the ways to connect with Suzu Labs https://suzulabs.com https://x.com/suzulabs https://www.linkedin.com/company/suzu-labs/

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  Episode #36

  Cloud Security, Shadow IT, and Breaking Into the Field with rekdt

  Sep 14, 202642 minS4

  Most advice about breaking into cybersecurity tells you to follow the path. rekdt makes the opposite case: the path is exactly what makes you look like everyone else. In this episode he shares a candid, sometimes contrarian view of the field, shaped by nearly two decades in it. rekdt runs a cloud security tower for a large enterprise operating across multiple clouds, and he came up through the professional cloud world during his time at AWS. He is also a longtime fixture in the hacker community, volunteering with the DEF CON Social Engineering Community and helping out at Red Team Village. His start in tech goes back to a teenage fascination with dial-up, the piracy and IRC scene, and picking apart malicious code on early MySpace pages, before a winding route through bartending and help desk work led him into engineering and eventually security. In this episode, rekdt and Phillip get into why the most interesting security conversations happen at cloud and developer conferences rather than security echo chambers, how cloud and containers upended traditional defenses, and why shadow IT and vibe coding are making things harder. rekdt explains why cybersecurity is really a people problem, what actually makes a candidate stand out when everyone has the same resume, and why he sometimes asks people why they want to get into security at all. He closes with honest, practical advice on building a career with an actual plan instead of just chasing the title. ========================= Connect with rekdt: https://x.com/rekdt ========================= Connect with your host, Phillip Wylie: LinkedIn: https://linkedin.com/in/phillipwylie X: https://x.com/PhillipWylie Instagram: https://www.instagram.com/phillipwylie

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  Episode #35

  From Cyber Warfare to AI-Powered Defense with Dave Kennedy

  Sep 7, 202634 minS4

  Dave Kennedy was a skeptic. After 28 years in the field, he had heard every claim about the next technology that was going to change cybersecurity, and he assumed AI was more of the same. Then it changed his mind, and now he is building some of the most advanced defensive AI in the industry. Dave is the founder of TrustedSec and Binary Defense. He got his start on the military intelligence side as a U.S. Marine in cyber warfare. He is a well-known name in the cybersecurity community through his work on BackTrack Linux, the Social-Engineer Toolkit, and Metasploit. Dave is also, by his own description, obsessed with cybersecurity as both a career and a hobby - he can't get enough of it. In this episode, Dave breaks down how AI has re-energized his work and, in his words, made this feel like the early 2000s all over again. He walks through Night Beacon, the AI system his team built to transform the security operations center, and explains why they train their own models instead of relying on frontier models, how they keep a human in the loop for every final determination, and why his teams now ship more than a million lines of code a week. Phillip and Dave get into what AI means for offensive work at TrustedSec and Binary Defense, concerns about autonomous hacking and cheaper zero days, and why Dave believes AI will create more work in cybersecurity rather than eliminate it. ========================= Connect with Dave Kennedy: https://www.linkedin.com/in/davidkennedy4 https://x.com/HackingDave https://binarydefense.com https://trustedsec.com ========================= Connect with your host, Phillip Wylie: LinkedIn: https://linkedin.com/in/phillipwylie X: https://x.com/PhillipWylie Instagram: https://www.instagram.com/phillipwylie

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  Episode #34

  Vulnerability Research, AI Slop, and Why Fundamentals Still Win with Stephen Sims

  Aug 31, 202635 minS4

  AI can now hand someone a working Linux kernel privilege escalation exploit, even if that person cannot explain a single line of how it works. Stephen Sims joined the show to talk about what that shift means for offensive security, and why the fundamentals matter more now, not less.Stephen is the curriculum lead for SANS Institute's Offensive Operations program, where he has spent more than 15 years as an author and instructor, and he is a co-founder of Off by One Security. He is a longtime exploit developer and vulnerability researcher who came up through game hacking, network engineering, and years of binary exploitation, reverse engineering, and weaponizing bugs in browsers and the kernel.In this episode, Stephen and Phillip get into how AI is reshaping vulnerability research and exploit development. Stephen explains why human validation is still doing the heavy lifting behind the big vulnerability-count headlines, how AI tends to overstate or understate severity, and why so many submissions are now AI slop or duplicates. He makes the case that logic bugs remain the hardest thing for AI to find, walks through his roadmap for anyone serious about learning exploit development, and shares why he tells students to do the work manually before letting AI do it for them. Stephen also offers grounded advice for breaking into the field, from building a real technology foundation first to staying curious and paying your dues, and gives his honest read on where the opportunity is heading.=========================Connect with Stephen Sims:LinkedIn: https://www.linkedin.com/in/stephen-sims-2788091/X: https://x.com/Steph3nSimsOff by One Security: https://offbyonesecurity.com/YouTube: https://www.youtube.com/@OffByOneSecurity=========================Connect with your host, Phillip Wylie:LinkedIn: https://linkedin.com/in/phillipwylieX: https://x.com/PhillipWylieInstagram: https://www.instagram.com/phillipwylie

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