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Phillip Wylie Show | Cybersecurity & Pentesting Podcast

Phillip Wylie
Cybersecurity
Penetration Testing
Offensive Security
Networking
Personal Branding
Hacking
Red Teaming
Social Engineering
Artificial Intelligence
Content Creation
Mentorship
Podcasting
Ethical Hacking
Bug Bounty
Threatlocker
Job Market
Soft Skills
Hack the Box
Ransomware
Certifications

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 ins... more

PublishesWeeklyEpisodes204Founded3 years ago
Number of ListenersCategory
Technology

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Latest Episodes

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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## 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-... more

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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 expla... more

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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... more

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Recent Guests

Andy Simpson
Consultant and user of Ridge Security tools
Cipher Security
Episode: Ridge Security in the Real World: An Offensive Security Practitioner's Perspective
Christian Gonzalez
Cybersecurity professional with a background in pentesting and red teaming
Episode: From Mischief to Mastery: Christian Gonzalez's Cybersecurity Journey
Eva Benn
Cybersecurity content creator and educator
Episode: Creating Content That Matters: Cybersecurity, Authenticity, and Building Your Brand with Eva Benn
Jeremiah Grossman
Founder of WhiteHat Security
WhiteHat Security
Episode: Jeremiah Grossman: The Future of Vulnerability Management
Ed Skoudis
Avid cybersecurity educator and founder of CounterHack; former Bellcore incident response professional
CounterHack
Episode: Hacking Then and Now: Ed Skoudis on AI, Pen Testing, and the Future of Cybersecurity
Winn Schwartau
Cybersecurity expert and author discussing hacker origin and cognitive security
Cognitive Security Institute / CyberCircus Network
Episode: Winn Schwartau: Hacker Culture, Cognitive Security, and the Human Element
Zach Tackett
Penetration tester at Secure Ideas
Secure Ideas
Episode: Zach Tackett: How Hands-On Experience and Networking Open Doors in Cybersecurity
Marie Hamilton
Guest on cybersecurity and entrepreneurship journey
Episode: Marie Hamilton: From Rejections to Success
Jamy Casteel
Offensive security professional specializing in infrastructure testing, red team engagements, and cloud pentesting
Independent consultant / security professional
Episode: Jamy Casteel: From Small Town IT to Offensive Security

Host

Phillip Wylie
Host of The Phillip Wylie Show | Cybersecurity & Pentesting Podcast; cybersecurity expert and educator

Chart Rankings

How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.

Apple Podcasts
#69
Russia/Technology
Apple Podcasts
#72
Ukraine/Technology

Talking Points

Recent interactions between the hosts and their guests.

Creating Content That Matters: Cybersecurity, Authenticity, and Building Your Brand with Eva Benn
Q: What advice do you have for someone starting out with content creation, especially around equipment and setup?
She advocates starting with low-cost gear, filming from a phone, and upgrading only as needed; focus on value to the audience, and use simple setups to reduce friction as you learn.
Creating Content That Matters: Cybersecurity, Authenticity, and Building Your Brand with Eva Benn
Q: What gets you interested in content creation, and what's your approach to making content valuable?
Eva discusses starting as a joke, the importance of authentic, helpful content, avoiding paywalls, and using a combination of AI-assisted prep with strong human judgment to deliver practical, credible guidance.
Creating Content That Matters: Cybersecurity, Authenticity, and Building Your Brand with Eva Benn
Q: What is your best career advice for someone wanting to break into cybersecurity in 2026?
She emphasizes mentorship, community support, and learning from established creators; highlight practical skills and projects over certifications, and build a network by sharing free content and roadmaps.
Creating Content That Matters: Cybersecurity, Authenticity, and Building Your Brand with Eva Benn
Q: Before we get started, if you wouldn't mind sharing your hacker origin story, how did you start out?
Eva explains growing up in Bulgaria, moving to the US, initially pursuing marketing, then stumbling into cybersecurity through a bootcamp and leadership roles, earning multiple certifications and awards, and eventually focusing on red teaming and content creation.
From Mischief to Mastery: Christian Gonzalez's Cybersecurity Journey
Q: What certifications did you find most valuable and why?
OSCP helped me gain hands-on lab experience and sparked practical penetration testing skills; CRTO with Red Team labs complemented that by teaching traversal and post-exploitation techniques.

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Frequently Asked Questions About Phillip Wylie Show

What is Phillip Wylie Show about and what kind of topics does it cover?

The show centers on high-skill offensive security topics, practical tradecraft, and career strategies in cybersecurity, with frequent discussions of vulnerability management, AI-driven threats, red teaming, and real-world pentesting workflows. Episodes feature seasoned practitioners, educators, and industry leaders who share deep technical insights, hands-on techniques, and personal career journeys—often tying technical concepts to business risk, regulatory implications, and evolving cyber threats. A notable strength is the emphasis on actionable tradecraft and career development within a security-focused ecosystem, making it a strong fit for listeners who want to translate complex security topics into practical, client-impactful takeaways.... more

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Which podcasts are similar to Phillip Wylie Show?

These podcasts share a similar audience with Phillip Wylie Show:

1. Simply Offensive
2. Hacker And The Fed
3. Darknet Diaries
4. Cybersecurity Today
5. SANS Internet Stormcenter Daily Cyber Security Podcast (Stormcast)

How many episodes of Phillip Wylie Show are there?

Phillip Wylie Show launched 3 years ago and published 204 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on Phillip Wylie Show?

Recent guests on Phillip Wylie Show include:

1. Andy Simpson
2. Christian Gonzalez
3. Eva Benn
4. Jeremiah Grossman
5. Ed Skoudis
6. Winn Schwartau
7. Zach Tackett
8. Marie Hamilton

To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.

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