Phillip Wylie Show

Latest Episodes:

Jeremiah Grossman: The Future of Vulnerability Management May 26, 2026

Show notes

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

Hacking Then and Now: Ed Skoudis on AI, Pen Testing, and the Future of Cybersecurity May 19, 2026

Show notes

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

Winn Schwartau: Hacker Culture, Cognitive Security, and the Human Element May 12, 2026

Show notes

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

Amar Sonik: Why Cybersecurity Fundamentals Still Matter May 05, 2026

Show notes

In this episode of The Phillip Wylie Show, Phillip sits down with Amar Sonik to talk about what really matters in cybersecurity.
They dig into why fundamentals like networking and Linux still separate good security professionals from great ones, how conferences like B-Sides Singapore and CYBR.HAK.CON. help shape careers, and how AI is changing the way people learn hacking.
Amar Sonik shares practical advice for anyone trying to break into cybersecurity, along with lessons from organizing security events and working in the field.
If you’re trying to get started or level up your skills, this episode keeps it real.
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Connect with Amar Sonik:
LinkedIn: https://www.linkedin.com/in/amarjitsonik/
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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
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Information about CYBR.HAK.CON. and tickets:
https://cybrhakcon.com/

Zach Tackett: How Hands-On Experience and Networking Open Doors in Cybersecurity Apr 28, 2026

Show notes

In this episode of The Phillip Wylie Show, Phillip sits down with Zach Tackett, a listener-turned-guest who carved his path into cybersecurity and pentesting through persistence, hands-on learning, and networking.
Zach shares his unconventional journey from a blue-collar upbringing and early struggles with asthma to discovering programming, cybersecurity, and ultimately landing roles supporting NASA and later becoming a security consultant at Secure Ideas. Along the way, he highlights the importance of real-world experience, building labs, and developing the hacker mindset.
This conversation is packed with practical advice for aspiring pentesters, including how to stand out in a competitive job market, the role of certifications vs. experience, and why networking can be more powerful than submitting resumes online.
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Connect with Zach Tackett:
LinkedIn: https://www.linkedin.com/in/zach-t-4862b487/
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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

Marie Hamilton: From Rejections to Success Apr 21, 2026

Show notes

In this episode of The Phillip Wylie Show, Phillip sits down with Marie Hamilton to explore her unconventional and inspiring path into cybersecurity. From early curiosity about computers and creative problem-solving as a teenager to serving in the military, navigating career pivots, and ultimately launching her own cybersecurity and investigations business, Marie shares a candid look at her journey.
They discuss the realities of breaking into cybersecurity, the value of community and networking, lessons learned from entrepreneurship, and how emerging technologies like AI are shaping the future of the field. Marie also dives into her current work in digital forensics, OSINT, and cyber law, offering valuable insights for anyone looking to enter or grow in the industry.
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Connect with Marie Hamilton:
LinkedIn: https://www.linkedin.com/in/wcymar2/
Opis website: https://www.opis-cybersecurity.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

From Pro Wrestler to Pentester: My Cybersecurity Origin Story Apr 08, 2026

Show notes

How do you go from professional wrestling and powerlifting to a career in cybersecurity and penetration testing?

In this special solo episode of The Phillip Wylie Show, Phillip Wylie shares his personal hacker origin story and the unconventional path that led him from wrestling matches and construction jobs to becoming a penetration tester, security evangelist, author, and podcast host.

If you're trying to break into cybersecurity, transition from IT, or wondering if it's too late to start, this episode shows that there is no single path into security.

Phillip discusses how curiosity, persistence, mentorship, public speaking, and content creation helped shape his career and how you can apply these same principles to your own journey.=========================

Connect with your host, Phillip Wylie:

LinkedIn: https://linkedin.com/in/phillipwylie

X: https://x.com/PhillipWylie

Instagram: https://www.instagram.com/phillipwylie

Jamy Casteel: From Small Town IT to Offensive Security Mar 31, 2026

Show notes

In this episode of The Phillip Wylie Show, host Phillip Wylie sits down with offensive security professional Jamy Casteel to discuss his journey from small-town IT technician to penetration tester and red teamer. Jamy shares how an early exposure to social engineering and physical pentesting sparked his interest in security and shaped his career path.
The conversation explores the differences between pentesting and red teaming, the value of consulting experience, and why understanding business risk is just as important as technical skill. Jamy also shares his thoughts on certifications versus real-world experience, the emerging role of AI in security testing, and why cybersecurity professionals should develop interests outside of technology to maintain balance and mental clarity.
This episode offers practical advice for aspiring cybersecurity professionals along with insights into how offensive security continues to evolve.
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Connect with Jamy Casteel:
LinkedIn: https://www.linkedin.com/in/jamy-casteel
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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

Travis Stein: Mastering Cybersecurity: Hands-On Skills and Networking Strategies Mar 24, 2026

Show notes

In this episode of the Phillip Wylie Show, host Phillip Wylie sits down with cybersecurity professional Travis Stein to discuss practical strategies for breaking into cybersecurity, building technical skills, and advancing from IT into security roles. Travis shares his journey from help desk roles into cybersecurity engineering and offers actionable advice for aspiring professionals looking to stand out in a competitive field.
The conversation highlights the importance of hands-on experience, networking, home labs, certifications, and building a personal portfolio to demonstrate real-world skills. Travis also discusses how soft skills like communication and presentations can accelerate career growth and open new opportunities.
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Connect with Travis Stein:
LinkedIn: https://www.linkedin.com/in/twstein86/
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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

Gregory Carpenter: Beyond the Network | Threat Modeling, AI, and Real-World Pen Testing Mar 17, 2026

Show notes

In this episode, Phillip Wylie sits down with Dr. Gregory Carpenter to explore his journey from early childhood curiosity to a distinguished career in cybersecurity, military operations, and advanced threat modeling.

Greg shares how his early interest in security evolved from physical lockpicking and unconventional problem solving into work involving digital security, NSA operations, and space-related missions.

The conversation dives into what effective threat modeling really looks like and why too many security assessments fail to account for real-world conditions. Greg explains the importance of looking beyond traditional network boundaries to include physical access, RF exposure, social engineering, environmental conditions, and human behavior. He also discusses the limits of narrowly scoped pen tests and why deeper, more realistic engagement is critical for understanding how attackers actually operate.

Phillip and Greg also examine the growing role of AI and automation in offensive security. Greg shares his perspective on how AI can improve security assessments, where automation adds value, and why creativity and adaptability still matter just as much as tools. They also cover dynamic defenses, deception, critical infrastructure risk, and how organizations can use intelligence sources such as MITRE, DOD, FBI, and DHS to strengthen their defensive strategies.

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Connect with Gregory Carpenter:

LinkedIn: https://www.linkedin.com/in/gcarpenter-cso-kbi/

Gregory's book: https://www.amazon.com/Reverse-Deception-Organized-Counter-Exploitation-McGraw-Hill/dp/B00E6T3VRA/

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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