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

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

October 8, 2025 · 38 min · Season 2 · Episode 67

About this episode

Trent Miller discusses how genuine friendships and community make pentesting enjoyable and help avoid stress.

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, ...

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