#66 The #1 Thing That Makes Pentesting Fun (Not Stressful) ft. Trent Miller

The Hacker's Cache

In this episode of The Hacker’s Cache, I sit down with penetration tester and security researcher Trent Miller (AzureAD) to talk about the one thing that makes pentesting fun instead of stressful: genuine friendships and community. We discuss how learning from other hackers, sharing experiences, and joining groups like DEF CON DC608 can accelerate your growth far beyond certifications or labs. Trent opens up about work-life balance, avoiding burnout, and the value of teaching what you learn, while I share my own perspective on grinding, AI in cybersecurity, and lessons from real client engagements. Whether you’re an aspiring pentester or already working in offensive security, this conversation reveals practical insights and a fresh way to look at learning in cybersecurity.

Connect with Trent Miller on LinkedIn: https://www.linkedin.com/in/azureadtrent/

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Music by Karl Casey @ White Bat Audio
Attention Listeners: This content is strictly for educational purposes, emphasizing ETHICAL and LEGAL hacking only. I do not, and will NEVER, condone the act of illegally hacking into computer systems and networks for any reason. My goal is to foster cybersecurity awareness and responsible digital behavior. Please behave responsibly and adhere to legal and ethical standards in your use of this information.
Opinions are my own and may not represent the positions of my employer.

فصول

1. Welcome & Guest Intro (00:00:00)

2. Work-Life Balance in Pentesting (00:02:38)

3. Improving Skills & Filling Knowledge Gaps (00:08:22)

4. Security Mad Libs Challenge (00:09:55)

5. The Internet’s Impact & Rise of AI (00:11:19)

6. Pentest Fumbles & Lessons Learned (00:16:09)

7. Building & Growing DEF CON Groups (00:19:02)

8. From Professional to Expert (00:28:03)

9. Overcoming Fear & Sharing Knowledge (00:31:17)

10. The Future of Cybersecurity Careers (00:34:16)