Phillip Wylie Show

What happens when a red teamer spends years sitting side by side with defenders, watching every EDR and SIEM on the market up close?

Trey Bilbrey has spent 18 years in IT and cybersecurity, from helping build the U.S. Marine Corps cyber program to red teaming industrial control systems for the Army Corps of Engineers, building Hack The Box Academy content and leading purple team engagements at Scythe, and he just launched his own consultancy.

Trey returns to the show two years after his first appearance as episode 100, and this time he shares why he now often recommends a detection over a fix, the moment leadership finally takes a pen test seriously, and how often organizations should really be running purple team exercises. He also gives a candid look at where AI fits into red teaming and threat emulation, including how far it can actually get from threat intelligence to a usable test plan, why a confident AI-built Sigma rule fooled no one, and his honest timeline for when AI could run a full red team engagement on its own.

Whether you’re trying to land your first cyber role, weighing Hack The Box against a degree, or curious about how purple teaming changes security culture, this episode is packed with real-world insight. Stick around to hear why Trey left big enterprise work behind to protect the small businesses in his own backyard, and how his Tampa nonprofit, the Neon Temple, is helping people break into the field.

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Connect with Trey Bilbrey:
LinkedIn: https://www.linkedin.com/in/georgebilbrey/
X: https://x.com/TCraf7

BSides Tampa Keynote: https://youtu.be/TBkzFBYU5vU?si=EtHqSUnAxIIv10yO

Trey's first appearance on the Phillip Wylie Show: https://www.youtube.com/watch?v=3n0BKLaqDvs

The Neon Temple (Non-Profit): https://www.theneontemple.com/https://www.youtube.com/@theneontemple/videos
Trey's Website: https://www.treycraft.com/

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Connect with your host, Phillip Wylie:
LinkedIn: https://linkedin.com/in/phillipwylie
X: https://x.com/PhillipWylie
Instagram: https://www.instagram.com/phillipwylie

What happens when someone who knows exactly how applications are built decides to start breaking them? Jarrod Rizor went from writing code and running DevOps to hacking web and mobile apps for a living, and he recently joined TrustedSec as a penetration tester. His path is a real-world playbook for anyone trying to break into offensive security.

Jarrod shares what actually gets someone hired as a pen tester, why being stubborn can matter more than being the smartest person in the room, and how putting your work out there can open doors a certification alone never will. He also gives an inside look at how AI is changing ethical hacking, including what happened when he turned Claude Code loose on an iOS app with Frida, and lays out a low-cost way to start learning mobile application security on Android before you ever spend money on iOS gear.

Whether you’re working toward the OSCP, grinding through Hack The Box, curious about mobile app pen testing, or wondering where AI fits into offensive security, this episode is full of practical insight from someone who has walked the path. Stick around to find out why the volunteers at his local wildlife rehab center say nobody else can handle Grimble the great horned owl.

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Connect with Jarrod Rizor:
LinkedIn: https://www.linkedin.com/in/jarrod-rizor-7270a832
X: https://x.com/Jr0dR87

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Connect with your host, Phillip Wylie:
LinkedIn: https://linkedin.com/in/phillipwylie
X: https://x.com/PhillipWylie
Instagram: https://www.instagram.com/phillipwylie

Tim MalcomVetter has spent 26 years moving between offense and defense, and his biggest takeaway is that the future of security comes down to speed - whoever has the fastest software wins.
Tim got his start by offering to work for free at a hospital in the early days of HIPAA, which turned into his first security job. From there he moved into pen testing, including work on the point-of-sale system behind roughly one in three U.S. credit card transactions, and then into red teaming at Walmart, where engagements could run as long as eight months. Today he is the co-founder of Wirespeed and General Manager of Coalition Security.
Recorded in person at Cybr.Sec.Con in Houston, this conversation with Phillip gets into what separates real red teaming from pen testing, what cyber insurance data reveals about which security controls actually work, and why so many in the industry misjudge risk. Tim also shares how his red team experience shaped his approach to automation, and why he sees the next era of attack and defense being decided in milliseconds.
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Connect with Tim MalcomVetter:
LinkedIn: https://www.linkedin.com/in/malcomvetter
WireSpeed: https://wirespeed.co
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Connect with your host, Phillip Wylie:
LinkedIn: https://linkedin.com/in/phillipwylie
X: https://x.com/PhillipWylie
Instagram: https://www.instagram.com/phillipwylie

License plate readers, police drones and fake cell towers are spreading fast, and two hackers are proving that anyone can detect them with about ten dollars of hardware and some open source firmware.
Colonel Panic is a malware researcher and hardware builder whose hacking started with AOL dial-up and stacks of 2600 Magazine. After years in restaurants and grocery retail, he went back to school during COVID, earned his certs and turned his love of rapid prototyping into privacy tools like OUI Spy. Cooper got his start on a hand-me-down 286 in fifth grade, spent his early years teaching privacy and security to activists, and has been a public interest technologist at the Electronic Frontier Foundation for almost thirteen years, where he works on Rayhunter.
Building on their DEF CON talk, "ESP32 as a Counter-Surveillance Platform," this episode covers:
- How OUI Spy uses an ESP32-S3 and a buzzer to alert you when specific Bluetooth or Wi-Fi devices or drones are nearby, and what changed when Flock updated its firmware
- Mesh Detect, which sends alerts over Meshtastic networks to build a sensor net for tracking drones
- Rayhunter, EFF's open source firmware that turns a cheap Orbic mobile hotspot into a cell-site simulator detector
- Why "I have nothing to hide" falls apart, including a Flock misread that put an innocent woman in jail for weeks
- The national security risk of ALPR data piling up with vendors who have a track record of vulnerabilities
- The current surveillance boom and EFF's work on litigation, activism, Privacy Badger and Certbot
- Why war driving is legal, and how to get involved by building tools or showing up at city council meetings
DEF CON 34 - ESP32 as counter-surveillance platform:
https://www.youtube.com/watch?v=PcK-TDmzshcEFF
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Connect with Colonel Panic:
Website: https://colonelpanic.tech
https://x.com/_colonel_panic
https://colonelpanic.tech/
Connect with Cooper:
https://bsky.app/profile/cooperq.com
EFF: https://www.eff.org
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Connect with your host, Phillip Wylie:
LinkedIn: https://linkedin.com/in/phillipwylie
X: https://x.com/PhillipWylie
Instagram: https://www.instagram.com/phillipwylie

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.

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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