
#66 The #1 Thing That Makes Pentesting Fun (Not Stressful) ft. Trent Miller
From The Hacker's Cache by Kyser Clark - Cybersecurity
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, ...
People in this episode
Host: Kyser Clark
Guest: Trent Miller
Topics covered
- pentesting
- cybersecurity
- community
- work-life balance
- burnout
- learning
- friendships
Keywords
- pentesting
- cybersecurity
- community
- friendships
- work-life balance
- burnout
- learning
Mentioned in this episode
Organizations: DEF CON DC608, AzureAD
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