Phillip Wylie Show

How is AI changing penetration testing, bug bounty hunting, and offensive security?
In this episode of The Phillip Wylie Show, Phillip sits down with Herman Zubenko to explore how artificial intelligence and automation are transforming the way security professionals discover and validate vulnerabilities.
Herman shares his unconventional journey from quality assurance and software development into cybersecurity, including how ...

In this episode of The Phillip Wylie Show, Phillip welcomes cybersecurity community member Moo for an inspiring conversation about breaking into cybersecurity, building a career through persistence, and giving back to others along the way.
Moo shares his unconventional hacker origin story, from being inspired by *The Matrix* and DEF CON videos as a teenager to eventually speaking at DEF CON and earning his first National Cyber L...

In this episode of The Phillip Wylie Show, Phillip Wylie sits down with offensive security researcher, educator, and entrepreneur Casey Smith (SubTee) to discuss his journey into cybersecurity, the evolution of offensive tradecraft, and why deception technology is becoming one of the most effective defensive strategies in today's threat landscape.

Casey shares how he transitioned from systems administration into security through...

Detection engineering doesn't always get the attention it deserves, but it's one of the most important parts of a mature security program.

In this episode of The Phillip Wylie Show, Phillip Wylie is joined by detection engineer and content creator Alex Hurtado to discuss why this growing specialty is becoming essential for modern security teams.

Alex shares how she went from monitoring enterprise networks early in her career to help...

In this episode of The Phillip Wylie Show, Phillip Wylie sits down with offensive security researcher Milton Valencia, better known in the cybersecurity community as wetw0rk. Known for his exploit development research, educational content, and commitment to mentoring others, Milton shares the remarkable journey that took him from a curious student fascinated by hacking to discovering zero-day vulnerabilities and working on elite of...

Mike Ortiz joins Phillip Wylie to discuss his journey from the early BBS and IRC days to the U.S. Marine Corps, global defense contracting, and ultimately becoming a red team operator specializing in adversary emulation and red team engineering. Along the way, Mike shares how his background in networking and enterprise infrastructure helped shape his approach to offensive security and why understanding both attack and defense is cr...

In this episode, Jason Faulhefer shares his hacker origin story, discusses his innovative threat intelligence platform Threat Spire, and explores the evolution of cybersecurity from early phone hacking to modern cloud and OT security.
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Connect with Jason Faulhefer:
LinkedIn - https://linkedin.com/in/jasonfaulhefer
X - https://x.com/jasonfaulhefer
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Connect with yo...

## How AI-Powered Penetration Testing Is Transforming Security Validation with Andy Simpson**Sponsored by Ridge Security**In this sponsored episode of The Phillip Wylie Show, Phillip Wylie welcomes Andy Simpson, founder of Cipher Security, for an in-depth discussion about the future of penetration testing, continuous security validation, API security, and the growing role of AI in offensive security.What makes this conversation uni...

What happens when hacking moves beyond computers and into devices that can keep people alive?
In this episode of The Phillip Wylie Show, Phillip Wylie welcomes Sean Satterlee to discuss the rapidly growing field of medical device security. Sean explains how security researchers evaluate connected healthcare technology, the skills needed to transition into hardware hacking, and why traditional pentesting knowledge is still incred...

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 i...

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 edu...

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 ear...

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 c...

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 ho...

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 ...

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...

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...

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 cybersec...

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, ...