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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