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

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

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