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July 10, 2025 41 mins

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

🎙️ WE NEED YOUR HELP! 🎙️

We’re in the running for Best Technology Podcast at PodcastAwards.com — and we’d love your vote!

🗳️ Go to https://www.podcastawards.com, register, and vote for Legitimate Cybersecurity in the Technology category.

Your vote helps real, nerdy cybersecurity voices rise to the top!

📌 Like, Subscribe & Share.

🔔 Click the bell to get notified about new episodes (and Frank’s midlife crises).

📎 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

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