Where Automation Ends, Cyber Ingenuity Begins with Phillip Wylie

Some tools replace tasks. Others reshape the way we think about security.

In this episode, Ron welcomes back Phillip Wylie, one of the most respected voices in offensive security, author, educator, and longtime friend of the Hacker Valley community. With over 27 years of experience across cybersecurity disciplines, Phillip has guided thousands of professionals through his books, talks, and mentorship.

He shares how AI is reshaping pen testing and red teaming, the value of automating away repetitive tasks, and why the fundamentals of security will always matter. From defining red teaming in 2025 to guiding newcomers on how to break in, Phillip delivers insights that balance cutting-edge innovation with timeless wisdom.

Impactful Moments: 00:00 - Introduction 01:00 - Why Phillip keeps podcasting 03:00 - AI opportunities in pen testing 04:30 - What automation should replace 06:00 - Red teaming vs pen testing in 2025 08:00 - Defining adversary emulation 10:40 - Building the ideal AI assistant 15:00 - The best AI use cases today 18:30 - AI-driven threat modeling 21:00 - Breaking into pen testing now 25:00 - Building a portfolio and personal brand 27:30 - Why in-person networking still matters

Links: Connect with Phillip on LinkedIn: https://www.linkedin.com/in/phillipwylie/

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