Phillip Wylie Show

Phillip Wylie

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.

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Phillip Wylie Show

Episodes (192)

Mar 31st Jamy Casteel: From Small Town IT to Offensive Security
Mar 24th Travis Stein: Mastering Cybersecurity: Hands-On Skills and Networking Strategies
Mar 17th Gregory Carpenter: Beyond the Network | Threat Modeling, AI, and Real-World Pen Testing

Phillip Wylie Show

Mar 31, 2026
33¾ minutes
29 MB

In this episode of The Phillip Wylie Show, host Phillip Wylie sits down with offensive security professional Jamy Casteel to discuss his journey from small-town IT technician to penetration tester and red teamer. Jamy shares how an early exposure to social engineering and physical pentesting sparked his interest in security and shaped his career path. The conversation explores the differences between pentesting and red teaming, the value of consulting experience, and why understanding business risk is just as important as technical skill. Jamy also shares his thoughts on certifications versus real-world experience, the emerging role of AI in...

Phillip Wylie Show

Jamy Casteel: From Small Town IT to Offensive Security

Phillip Wylie

00:00 -31:58