Phillip Wylie
Phillip Wylie Show | Cybersecurity & Pentesting Podcast
The Phillip Wylie Show is a premier cybersecurity podcast and media source for offensive security professionals. Hosted by Phillip Wylie, globally recognized ethical hacking expert, keynote speaker, and co-author of The Pentester Blueprint, the show features elite red team operators, penetration testers, and security leaders sharing real-world tradecraft, advanced tactics, career strategy, and insights on AI-driven cyber threats.
Author
Phillip Wylie
Category
Podcast website
Latest episode
Jul 7, 2026
Where to listen?
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Episodes
From BBS to Mastering Red Team Operations with Mike Ortiz 07.07.2026 32:54
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 understa...
From Phone Phreaking to Cloud Security: Jason Faulhefer's Cyber Journey 02.07.2026 44:09
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. ========================= Connect with Jason Faulhefer: LinkedIn - https://linkedin.com/in/jasonfaulhefer X - https://x.com/jasonfaulhefer =========================...
Ridge Security in the Real World: An Offensive Security Practitioner's Perspective 23.06.2026 58:46
## 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 securi...
From Hacker to Medical Device Pentester: Sean Satterlee on Securing Life-Critical Technology 17.06.2026 30:47
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 pent...
From Mischief to Mastery: Christian Gonzalez's Cybersecurity Journey 09.06.2026 23:33
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 aspi...
Creating Content That Matters: Cybersecurity, Authenticity, and Building Your Brand with Eva Benn 02.06.2026 32:08
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 profe...
Jeremiah Grossman: The Future of Vulnerability Management 26.05.2026 27:52
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 vulnerab...
Hacking Then and Now: Ed Skoudis on AI, Pen Testing, and the Future of Cybersecurity 19.05.2026 32:34
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...
Winn Schwartau: Hacker Culture, Cognitive Security, and the Human Element 12.05.2026 31:46
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 cybersec...
Amar Sonik: Why Cybersecurity Fundamentals Still Matter 05.05.2026 26:47
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 practi...
Zach Tackett: How Hands-On Experience and Networking Open Doors in Cybersecurity 28.04.2026 37:06
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 NA...
Marie Hamilton: From Rejections to Success 21.04.2026 38:25
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 journe...
From Pro Wrestler to Pentester: My Cybersecurity Origin Story 08.04.2026 33:07
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'...
Jamy Casteel: From Small Town IT to Offensive Security 31.03.2026 31:58
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 betw...
Travis Stein: Mastering Cybersecurity: Hands-On Skills and Networking Strategies 24.03.2026 47:42
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 sta...
Gregory Carpenter: Beyond the Network | Threat Modeling, AI, and Real-World Pen Testing 17.03.2026 40:22
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-rel...
Allie Mellen: Code War 10.03.2026 28:55
In this episode of the Phillip Wylie Show, Allie Mellen shares her journey from a computer engineering student to a cybersecurity expert and industry analyst. She discusses the importance of hands-on experience in cybersecurity, the evolution of cybersecurity tools, and the significance of a hacker mindset. Allie also emphasizes the need for clear communication in cybersecurity for non-technical a...
Eve Maler: The Evolution of Identity Security 03.03.2026 31:39
In this episode of the Phillip Wylie Show, host Phillip Wylie speaks with Eve Maler, a prominent figure in identity security. They discuss the importance of community in cybersecurity, Eve's journey into the field, the evolution of identity technologies like SAML and OAuth, advancements in authentication methods, and the impact of AI on identity management. Eve also shares insights from her up...
Sudhanshu Chauhan: Navigating the New Landscape of Cyber Threats 24.02.2026 33:50
In this episode, Sudhanshu Chauhan discusses the transformative impact of AI on the cybersecurity landscape. He explains how AI has introduced new attack vectors and the dual nature of AI in cybersecurity, serving both as a tool for attacks and as a target for attacks. The conversation emphasizes the need for security professionals to adapt to these changes and explore innovative approaches to pen...
Dorota Kozlowska: Empowering Women in Cybersecurity 17.02.2026 43:48
In this episode of the Phillip Wylie Show, Dorota Kozlowska shares her inspiring journey from a hesitant high school student to a successful professional in offensive security and content creation. She discusses her challenges in breaking into the male-dominated field of cybersecurity, her passion for pen testing, and her commitment to empowering other women in tech through her podcast, 'The W...
Keelan Knox: Breaking Things to Building Defenses 10.02.2026 27:34
In this episode of the Phillip Wylie Show, host Phillip Wylie welcomes cybersecurity expert Keelan Knox, who shares his fascinating hacker origin story. Keelan recounts his early curiosity about technology, which led him to dismantle various devices and eventually discover the world of hacking and cybersecurity. He emphasizes the importance of social engineering in the field and how it became a na...
Michael Farnum & Sam Van Ryder: Building CYBR.SEC.Community 03.02.2026 29:27
In this episode of The Phillip Wylie Show, Phillip Wylie sits down with Michael Farnum and Sam Van Ryder to discuss the growth of CYBR.SEC.Community, formerly known as HOU.SEC.CON. They share their hacker origin stories and how a grassroots conference evolved into a national, community-driven cybersecurity movement. The conversation covers the expansion of CYBR.SEC.Community to include OT.SEC.CON,...
Travis Weathers: From Military to Physical Security Expert 27.01.2026 30:33
In this episode of the Phillip Wylie Show, host Phillip’s guest is Travis Weathers, a seasoned professional in cybersecurity and penetration testing. Travis shares his unique journey from military service to becoming a successful entrepreneur in the cybersecurity field. He discusses the importance of specialized training, the differences between red teaming and traditional pen testing, and offers...
Unpacking Cybersecurity: Stories from the Cyber Distortion Podcast 20.01.2026 44:45
Summary In this episode of the Phillip Wylie Show, Phillip welcomes Jason and Kevin from the Cyber Distortion Podcast, diving deep into their hacker origin stories and the evolution of their podcasting journey. Kevin shares his unconventional path from marketing and graphic design to IT, highlighting how a conversation about salaries led him to pursue Microsoft certifications and a long-standing c...
Shubham Khichi: Journey The Future of AI in Cybersecurity 13.01.2026 37:14
Summary In this episode of the Phillip Wylie Show, Phillip Wylie interviews Shubham Khichi, a cybersecurity expert and entrepreneur. They discuss Shubham's journey from a computer science student to the founder of CyberAGI, a company focused on enhancing cybersecurity through AI. The conversation covers the importance of human involvement in cybersecurity, innovative threat modeling techniques...
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