Where Automation Ends, Cyber Ingenuity Begins with Phillip Wylie

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/

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/

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Episode 36 - Life and Purpose Mapping Hacks with Craig Filek

Episode 36 - Life and Purpose Mapping Hacks with Craig Filek

Life and purpose hacks with Craig Filek - One of our favorite episodes to record with a friend of the podcast. Craig Filek gives outstanding perspective on mapping purpose with your life.

30 Jan 202039min

Episode 35 - Not a Moment, But a Movement with Makinde Adeagbo

Episode 35 - Not a Moment, But a Movement with Makinde Adeagbo

Inclusion and diversity are areas that we can all make an impact in. Makinde Adeagbo Founder @ /dev/color shares insightful wisdom for making an impact and bringing diversity to Technology

29 Jan 202025min

Episode 34 - Cybersecurity: New to Good to Great with Susan Peediyakkal

Episode 34 - Cybersecurity: New to Good to Great with Susan Peediyakkal

How do you go from good to great? The question is even more tough when you have limited experience in your focus area. In this episode, Susan Peediyakkal joins the podcast to share her background in Threat Intelligence and successful career pivots while strengthening her craft

29 Jan 202032min

Episode 33 - Demystifying the Zero Trust Model with Kathy Wang

Episode 33 - Demystifying the Zero Trust Model with Kathy Wang

What type of data is your organization processing and storing? How sensitive is your organization's data? In this Episode, Kathy Wang CISO @ FullStory shines light on Zero Trust and building successful security teams.

28 Jan 202017min

Episode 32 - Cyber Transformations and Migrations with Talha Tariq

Episode 32 - Cyber Transformations and Migrations with Talha Tariq

Technology enables companies to constantly stay in touch and enable their customers. As opportunity grows, organizations evolve and focus on technology and data-driven results. Talha Tariq CSO of HashiCorp joins Chris and Ron to talk rapidly deploying and securing organizations while enabling employees.

28 Jan 202031min

Epsode 31 - The Future of Work and Your Purpose with Tim Salau

Epsode 31 - The Future of Work and Your Purpose with Tim Salau

The year 2020 marked the beginning of a new decade. Each year we experience evolving roles and responsibilities in the workplace. In this episode, Tim Salau (Mr. Future of Work) joins Chris and Ron to discuss the future of work and applying purpose.

27 Jan 202039min

Episode 30 - Threat Hunting with Data Science - Roberto Rodriguez

Episode 30 - Threat Hunting with Data Science - Roberto Rodriguez

Being an expert Threat Hunter is great, but how do you scale as fast as the adversary? Roberto Rodriguez (cyb3rward0g) joins the podcast and shares experience for breaking into cybersecurity and creating a community around scaling cybersecurity solutions.

15 Jan 202034min

Episode 29 - Road to The SANS CTI Summit with Rick Holland

Episode 29 - Road to The SANS CTI Summit with Rick Holland

Cyber Threat Intelligence is a topic that evolves as the adversary changes Tactics Techniques and Procedures. In this episode, Rick Holland join Chris and Ron to discuss his journey through CTI and the upcoming CTI Summit   We'd love to meet everyone at the SANS CTI Summit in Washington DC on January 20 Link: http://www.sans.org/u/XJ4 Discount Code: CTIPOD20

14 Jan 202018min

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