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

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Continue the conversation by joining our Discord: https://hackervalley.com/discord

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Episode 12 - Physical Red Teaming: No Lock Left Secured

Episode 12 - Physical Red Teaming: No Lock Left Secured

Robert Pingor is the equalizer to Physical and Network Red Teaming. Chris has had the opportunity to moonlight his career with Robert and witness him obtain mastery at his craft. During this interview, Chris, Ron, and Robert share red team stories and resources for Red Team Alliance.

13 Aug 201915min

Episode 11 - Selling Cybersecurity: Doing Business in an Increasingly Connected World

Episode 11 - Selling Cybersecurity: Doing Business in an Increasingly Connected World

Information Security vendors offer a wide variety of products and services that can enable success for organizations. Derek Eid joins us this episode to share wisdom in selling products and services. Derek is an expert communicator and leverages technical and non-technical conversations to capture necessities for existing and potential customers. Derek's most effective tool in his repertoire is his ability to listen. Tune in and learn how he uses this powerful tool to help enable his success.

23 Juli 201937min

Episode 10 - Breaking Barriers, Gatekeepers, and Glass Ceilings

Episode 10 - Breaking Barriers, Gatekeepers, and Glass Ceilings

Neelima Rustagi joins Chris and Ron in this episode to share her experiences creating valuable work to dissolve barriers, gatekeepers, and glass ceilings. While transitioning from Software Engineer to Cybersecurity Product Manager, Neelima provided value to her stakeholders, mentors and advocates to position herself as a key resource in the industry. Neelima celebrates a decorated background in startups and Fortune cybersecurity companies.

16 Juli 201939min

Episode 9 - The Intelligence Easy Button

Episode 9 - The Intelligence Easy Button

In this Episode, Ron and Napoleon put Chris in the hot seat and reviewed his EASY framework for making an impact in threat intelligence.   - Elicit Requirements - Assess Collection - Plan Strive for Impact - Yield to Feedback   All four pillars are vital for ensuring success during each phase of providing threat intelligence as a service

7 Juli 201919min

Episode 8 - Serverless Threat Intel Bot

Episode 8 - Serverless Threat Intel Bot

New Member Alert 🚨! Napoleon Bing joins forces with Chris and Ron and present a Serverless Threat Intel Bot. As organizations mature and scale their security infrastructure, it's vital that analysts, engineers, and other team members are able to query and enrich data on demand. Additionally, application features are being introduced at an increasing rate, creating the need for software defined infrastructure. In this project, we'll be exploring scaling automation efforts - with a focus on Threat Intelligence. This project can serve as a guide for when to leverage an interactive bot, creating API endpoints, serverless architecture, and applying actionable threat intelligence.

7 Juli 201913min

Episode 7 - Layer 8 - Vulnerability And Diversity

Episode 7 - Layer 8 - Vulnerability And Diversity

How important is being vulnerable in life and in your career? In Episode 7, our guest of honor - Charles Nwatu (https://www.linkedin.com/in/cnwatu/) joins Ron and Chris in starting the conversation about vulnerability and diversity. Charles Nwatu celebrates a decorated infosec career - and has built security teams at companies such as Twilio, Stitch Fix, and Netflix.

7 Juli 201944min

Episode 6 - MITRE ATT&CK™ Matrix Overview

Episode 6 - MITRE ATT&CK™ Matrix Overview

In this episode, Chris Cochran and Ronald Eddings review the MITRE ATTACK Matrix and discuss related threat actors, TTPs, Threat Intelligence, and vendor evaluations.

7 Juli 201921min

Episode 5 - What legacy do you want to leave

Episode 5 - What legacy do you want to leave

In this episode, Chris presents a deep question to Ron during a live recording. What legacy do you want to leave? This can have many meanings for people. Do you want to leave a legacy with your family? Your career? Life in general? In this video, Ron and Chris also share future episode topics

7 Juli 201917min

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