Are you curious about penetration testing, aka legal hacking? In this episode of Legitimate Cybersecurity, Frank and Dustin tear down the myths of hacking, break down real-world pen testing, and share hilarious (and horrifying) war stories from the field.

We cover:

✅ The skills you actually need to get into pen testing

✅ What certs like OSCP, CEH, and GPEN really mean

✅ Why most companies have no idea what’s on their network

✅ Real pen test experiences gone sideways

✅ Why you might still get arrested after a bug bounty

✅ And how to break into the field—even without a degree

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📎 Check the show notes for career resources, links, and our Hack the Box profile recs!

#PenTesting #EthicalHacking #CybersecurityCareers #OSCP #CEH #GPEN #HackTheBox #RedTeam #CyberSecurityPodcast #InfoSec #HackerLife #BugBounty #CybersecurityTraining #CyberMythsBusted #ITSecurity #SecurityTesting #KaliLinux #CyberCareer #podcastawards

Chapter Breaks

00:00 - Intro: What Is Penetration Testing?

01:31 - Myths vs. Reality of Hacking

02:40 - What Kind of People Make Good Pen Testers?

05:33 - You Don’t Need a Degree To Be a Hacker

07:19 - Why AI-Generated Code Is Easy to Hack

09:16 - Cybersecurity Certifications (OSCP, CEH, GPEN)

12:16 - Is CEH Still Worth It?

14:42 - What EC in EC-Council *Actually* Stands For

16:20 - Pen Test Expectations vs. Reality

19:35 - Types of Pen Tests: Internal, External, Web App, Social Engineering

22:12 - Cost, Scope & Asset Prioritization

24:00 - What If You Don’t Know Your Own Assets?

26:58 - Pen Test Reports: Why No One Reads Them

28:55 - Remediation Is Scarier Than the Hack

30:49 - Hacker Teams: Foothold → Escalation → Ransom

32:31 - The Most Hilarious Old Systems We’ve Found

34:28 - You Must *Love* Computers To Hack Well

37:03 - Want to Be a Hacker? Here’s Your Roadmap

39:51 - Military & DOD Paths To Cyber Careers

40:44 - Vote for Us, Subscribe, and Frank’s Midlife Crisis