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Security ChipmunksAuthor: Edna
Welcome to Security Chipmunks where we talk about the development of cybersecurity skills. To stay up to date in today's world you need to be resilient, thats why as Advanced Persistent Chipmunks we keep chipping away at it. Language: en-us Genres: Education, How To, Technology Contact email: Get it Feed URL: Get it iTunes ID: Get it |
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From Sysadmin to Ethical Hacker: Phillip Wylie shares Skills, Labs, and Real-World Strategies
Episode 23
Friday, 3 October, 2025
Send us a textWant a real-world map into penetration testing instead of a maze of hot takes? We sit down with Philip Wiley—offensive security veteran, teacher, and author of The Pentester Blueprint—to unpack practical paths that work today. Philip traces his journey from sysadmin to consultant and shows how prior roles become leverage in security: command line fluency, networking instincts, audit rigor, and the ability to translate technical findings into business impact. If you’ve wondered whether you “must” start in IT, you’ll hear why transferable skills matter more than a single prescribed path.We dig into how learning has shifted. Five years ago, home labs were the default; now, cloud-based platforms like Hack The Box, TryHackMe, and Antisyphon accelerate skill-building without the drag of fragile setups. Philip breaks down which certifications best reflect hands-on ability—think PNPT, TCM’s junior pen tester, and OSCP—and how to structure your study with focused reps, thorough enumeration, and disciplined reporting. Expect honest advice about fundamentals over shortcuts, the value of repetition, and why a good methodology beats a bag of tricks.Mentorship and community run through everything here. Philip shares what successful learners actually do, how encouraging guidance can flip hesitation into action, and why showing up at B-Sides, OWASP, and local hacker associations opens doors you didn’t know existed. We also talk personal branding—publishing talks, write-ups, and even books—to make your progress visible and credible to hiring managers. You’ll leave with a weekly cadence you can start immediately: deliberate labs, concise notes, a study group, and one community touchpoint that compounds into opportunities.If this conversation helps you chart your next step into offensive security, follow the show, share it with a friend who’s studying, and leave a review so more learners can find it.Socials Join our Chipmunk community Discord server: https://discord.gg/9yfWP6evYQ Follow us on Twitter: https://twitter.com/SecChipmunk You can find us online at: https://securitychipmunks.com
