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/
Check out our upcoming events: https://www.hackervalley.com/livestreams
Join our creative mastermind and stand out as a cybersecurity professional: https://www.patreon.com/hackervalleystudio
Love Hacker Valley Studio? Pick up some swag: https://store.hackervalley.com
Continue the conversation by joining our Discord: https://hackervalley.com/discord
Become a sponsor of the show to amplify your brand: https://hackervalley.com/work-with-us/
Popular Podcasts
Stuff You Should Know
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.
Dateline NBC
Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com
On Purpose with Jay Shetty
I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!