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

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…

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From Cyber Warfare to AI-Powered Defense with Dave Kennedy - Phillip Wylie

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.…

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

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…

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

YouTube video by Phillip Wylie

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Purple Teaming with Sarah Hume: Turning Threat Intelligence Into Actionable Testing - Phillip Wylie

Penetration testing tells you where the vulnerabilities and misconfigurations are. Purple teaming asks a different question: when an attacker is actually operating inside your environment, what can your tools see, and what slips right past them? Sarah Hume has built her career around that second question. Sarah leads the Purple Team program at Security Risk…

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Phillip Wylie

Phillip is a passionate offensive security professional with over 28 years of information technology and cybersecurity experience. His specialties include penetration testing and application security....

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From English Teacher to OSINT Investigator: Lindsey Yagi-Hatake on Breaking Into Cybersecurity - Phillip Wylie

In under a year, Lindsey Yagi-Hatake went from teaching English in a public school classroom to working as a professional OSINT investigator. Her path into cybersecurity did not start with a certification or a computer science degree. It started with survival. Lindsey spent six years as a public school English teacher and holds a master’s…

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AI, Automation, and the Future of Penetration Testing with Herman Zubenko - Phillip Wylie

How is AI changing penetration testing, bug bounty hunting, and offensive security?In this episode of The Phillip Wylie Show, Phillip sits down with Herman Zubenko to explore how artificial intelligence and automation are transforming the way security professionals discover and validate vulnerabilities.Herman shares his unconventional journey from quality assurance and software development into cybersecurity, including…

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From First-Generation Graduate to DEF CON Speaker: Moo's Cybersecurity Journey - Phillip Wylie

In this episode of The Phillip Wylie Show, Phillip welcomes cybersecurity community member Moo for an inspiring conversation about breaking into cybersecurity, building a career through persistence, and giving back to others along the way.Moo shares his unconventional hacker origin story, from being inspired by *The Matrix* and DEF CON videos as a teenager to…

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Casey Smith (SubTee): Living Off the Land, Deception Technology, and the Evolution of Offensive Security - Phillip Wylie

In this episode of The Phillip Wylie Show, Phillip Wylie sits down with offensive security researcher, educator, and entrepreneur Casey Smith (SubTee) to discuss his journey into cybersecurity, the evolution of offensive tradecraft, and why deception technology is becoming one of the most effective defensive strategies in today’s threat landscape. Casey shares how he transitioned…

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Casey Smith (SubTee): Living Off the Land, Deception Tech, and the Evolution of Offensive Security

YouTube video by Phillip Wylie

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The Future of Detection Engineering with Alex Hurtado - Phillip Wylie

Detection engineering doesn’t always get the attention it deserves, but it’s one of the most important parts of a mature security program. In this episode of The Phillip Wylie Show, Phillip Wylie is joined by detection engineer and content creator Alex Hurtado to discuss why this growing specialty is becoming essential for modern security teams.…

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From Curiosity to Zero Days: Milton Valencia (wetw0rk) on Exploit Development, Research, and Giving Back - Phillip Wylie

In this episode of The Phillip Wylie Show, Phillip Wylie sits down with offensive security researcher Milton Valencia, better known in the cybersecurity community as wetw0rk. Known for his exploit development research, educational content, and commitment to mentoring others, Milton shares the remarkable journey that took him from a curious student fascinated by hacking to…

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From BBS to Mastering Red Team Operations with Mike Ortiz - Phillip Wylie

Mike Ortiz joins Phillip Wylie to discuss his journey from the early BBS and IRC days to the U.S. Marine Corps, global defense contracting, and ultimately becoming a red team operator specializing in adversary emulation and red team engineering. Along the way, Mike shares how his background in networking and enterprise infrastructure helped shape his…

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From Phone Phreaking to Cloud Security: Jason Faulhefer's Cyber Journey - Phillip Wylie

In this episode, Jason Faulhefer shares his hacker origin story, discusses his innovative threat intelligence platform Threat Spire, and explores the evolution of cybersecurity from early phone hacking to modern cloud and OT security.========================= Connect with Jason Faulhefer:LinkedIn – https://linkedin.com/in/jasonfaulheferX – https://x.com/jasonfaulhefer========================= Connect with your host, Phillip Wylie: LinkedIn: https://linkedin.com/in/phillipwylieX: https://x.com/PhillipWylieInstagram: https://www.instagram.com/phillipwylie========================= I’m excited to…

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Web Application Pentesting and the Importance of Specialization with Tib3rius - Phillip Wylie

About The Guest:Tib3rius is a penetration tester with over ten years of experience, specializing in web application security. He is the creator of the popular tool Autorecon, which is widely used for enumeration in the OSCP exam and CTF challenges. Tib3rius also offers courses on Udemy and Hackers Academy, focusing on privilege escalation techniques for…

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Shenetworks: Leveraging Content Creation to Build a Career in Cybersecurity - Phillip Wylie

About The Guest:Shenetworks is a content creator and cybersecurity professional known for her educational videos on TikTok. She has built a following by sharing technical content and leveraging various social media platforms to educate and engage with the cybersecurity community. Summary:Shenetworks discusses her journey as a content creator and how she has leveraged brand building…

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Jessica Barker: The importance of cybersecurity culture and awareness - Phillip Wylie

About The Guest:Jessica Barker is a cybersecurity expert and co-founder of Cygenta, a company that focuses on the human, technical, and physical aspects of cybersecurity. With a background in sociology and civic design, Jessica brings a unique perspective to the field of cybersecurity. She is the co-author of “Cybersecurity ABCs” and “Confident Cybersecurity,” and is…

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Lilly Chalupowski's Journey Into Malware Analysis - Phillip Wylie

About The Guest:Lilly Chalupowski, also known as Cerberus, is a malware reverse engineer specializing in criminal malware. She has extensive experience in analyzing various malware families and has developed open-source projects to aid in the detection and extraction of intelligence from malware. Lilly is also a talented musician and often incorporates guitar playing into her…

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Bat: The Evolution of a Threat Hunter - Phillip Wylie

Summary In this episode of the Philip Wylie Show, Bat shares her journey from a childhood fascination with computers to a career in cybersecurity, specifically in threat hunting. Bat discusses her early experiences with hacking, the transition from wanting to be a pen tester to discovering a passion for digital forensics, and the day-to-day responsibilities…

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Casey Cammilleri: From Hacker to CEO - Phillip Wylie

Summary In this episode of the Phillip Wylie Show, host Phillip Wylie speaks with Casey Camilleri about the evolution of offensive security, the importance of continuous penetration testing, and the role of automation and AI in the cybersecurity landscape. They discuss Casey’s hacker origin story, the shift in mindset required for modern security practices, and…

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