Phillip Wylie Show | Cybersecurity & Pentesting Podcast

In this episode of The Phillip Wylie Show, Phillip sits down with longtime friend, former student, and offensive security professional Christian Gonzalez.
Christian shares his journey from curious teenager and network engineer to penetration tester, mobile application security specialist, and AI security researcher.
The conversation explores career growth, certifications, AI security, and how aspiring pentesters can stay relevant in an increasingly competitive cybersecurity landscape.

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Connect with Christian Gonzalez:
LinkedIn: https://www.linkedin.com/in/christian-g-672104160/
Educational AI Pentesting Lab: https://www.aipwn.me/
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Connect with your host, Phillip Wylie:
LinkedIn: https://linkedin.com/in/phillipwylie
X: https://x.com/PhillipWylie
Instagram: https://www.instagram.com/phillipwylie

In this episode of The Phillip Wylie Show, Phillip Wylie welcomes back cybersecurity leader, content creator, and self-described "Cybersecurity Bestie," Eva Benn. Eva shares her journey from growing up in rural Bulgaria with no access to technology to becoming a cybersecurity leader, red team professional, and influential content creator. The conversation explores how cybersecurity professionals can leverage content creation to educate others, grow their careers, and make a meaningful impact on the community.
Rather than focusing on followers or personal branding, Eva discusses why successful content creation starts with helping others. She offers practical advice for aspiring creators, explains how she built her Security Mondays series, shares lessons learned from producing cybersecurity content, and discusses the importance of authenticity in an AI-driven world.
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Connect with Eva Benn:
LinkedIn: https://www.linkedin.com/in/evabenn/
YouTube: https://www.youtube.com/@evabennofficial
Instagram: https://www.instagram.com/evabennofficial/
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Connect with your host, Phillip Wylie:
LinkedIn: https://linkedin.com/in/phillipwylie
X: https://x.com/PhillipWylie
Instagram: https://www.instagram.com/phillipwylie

In this episode of The Phillip Wylie Show, Phillip Wylie sits down with legendary application security pioneer and entrepreneur Jeremiah Grossman to discuss the evolution of web security, vulnerability management, cyber insurance, AI-driven software development, and the future of offensive security.Jeremiah shares his hacker origin story, from hacking his ISP as a teenager to discovering vulnerabilities in Yahoo Mail during the early days of the web. That experience eventually led him to Yahoo and later to founding WhiteHat Security, one of the first SaaS-based web application security companies.The conversation dives deep into how application security evolved from manual testing and early vulnerability scanners into scalable AppSec programs, as well as why modern vulnerability management is still fundamentally broken. Jeremiah explains why only a tiny percentage of CVEs ever lead to real financial loss and how his latest company is approaching vulnerability prioritization differently.

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Connect with Jeremiah Grossman:
LinkedIn: https://www.linkedin.com/in/grossmanjeremiah
Website: https://www.jeremiahgrossman.com
Root Evidence: https://www.rootevidence.com

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Connect with your host, Phillip Wylie:
https://linkedin.com/in/phillipwylieX
https://x.com/PhillipWylieInstagram
https://www.instagram.com/phillipwylie

Chapters

00:00 Introduction to Content Creation Journey
02:15 Eva's Hacker Origin Story
05:03 Career Advice for Aspiring Cybersecurity Professionals
06:19 The Importance of Skills Over Certifications
07:44 Motivation Behind Content Creation
10:00 Navigating Misinformation in Cybersecurity Education
12:57 The Role of AI in Content Creation
13:41 Mindset Shifts for New Content Creators
16:38 Types of Content and Finding Your Niche
18:20 The Importance of Experience in Content Creation
20:41 Balancing Structure and Authenticity in Content
24:44 Equipment Recommendations for Beginners
28:18 Final Thoughts on Content Creation
31:44 Phillip Wylie Show Outro

In this episode of The Phillip Wylie Show, Phillip Wylie sits down with legendary security expert Ed Skoudis to discuss his hacker origin story, the evolution of penetration testing, and how AI is transforming offensive security.
Ed shares how he got started hacking on early home computers like the Commodore VIC-20 and Timex Sinclair 1000, his journey into professional penetration testing, and the early days of DEF CON and the cybersecurity industry. The conversation also dives deep into AI-assisted penetration testing, vulnerability discovery, the future of CTFs, certifications, home labs, and what aspiring hackers should focus on to succeed in today’s rapidly changing landscape.
From classic hacking stories to cutting-edge AI research, this episode is packed with insights for anyone interested in ethical hacking, red teaming, and the future of cybersecurity.
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Connect with Ed Skoudis:
LinkedIn: https://www.linkedin.com/in/edskoudis
Website: https://www.counterhack.com/
SANS Holiday Hack Challenge: https://www.sans.org/cyber-ranges/holiday-hack-challenge
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Connect with your host, Phillip Wylie:
LinkedIn: https://linkedin.com/in/phillipwylie
X: https://x.com/PhillipWylie
Instagram: https://www.instagram.com/phillipwylie

Computer security analyst and author Winn Schwartau joins Phillip Wylie for a deep conversation on hacker culture, cognitive security, information warfare, and the evolution of cybersecurity from the early days of computing to today’s AI-driven world.
Winn shares stories from his early days bypassing locked telephone systems as a child, his transition from the live recording industry into cybersecurity in the 1980s, and how his engineering mindset shaped his approach to systems hacking. The conversation explores the rise of cloud computing, the increasing specialization required in cybersecurity, and why human behavior remains one of the industry’s biggest vulnerabilities.
The episode also dives into Winn’s groundbreaking work around cognitive security, misinformation, disinformation, and “critical ignoring” — the idea that filtering out noise is becoming just as important as critical thinking in today’s information-overloaded society.
Listeners will also hear Winn’s thoughts on hiring practices in cybersecurity, why failure is essential for growth, and how the industry still overlooks talented people who do not fit traditional hiring molds.
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Connect with Winn Schwartau:
LinkedIn: https://www.linkedin.com/in/winnschwartau
Website: https://www.winnschwartau.com/
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Connect with your host, Phillip Wylie:
LinkedIn: https://linkedin.com/in/phillipwylie
X: https://x.com/PhillipWylie
Instagram: https://www.instagram.com/phillipwylie