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Want 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
Chapters
1. Welcome & Collaboration Payoffs (00:00:00)
2. Philip’s Background in Offense (00:01:23)
3. Breaking Into Pen Testing (00:02:49)
4. Fundamentals Over Shortcuts (00:05:17)
5. Consulting, Variety, and Transferable Skills (00:08:02)
6. Mentoring Mindset That Enables Growth (00:10:45)
7. The Book: Relevance and Updates (00:12:13)
8. Cloud Labs vs Home Labs (00:15:10)
9. Certifications That Matter Now (00:18:10)
10. Why Publish: Access and Credibility (00:20:00)
11. What Successful Learners Do (00:22:06)
12. Conferences, Meetups, and Networking (00:24:14)
23 episodes
