#72 He Quit His Cybersecurity Job to Start a Pentesting Company ft. Tyler Ramsbey
From The Hacker's Cache by Kyser Clark - Cybersecurity
May 29, 2026 · 47 min · Season 2 · Episode 73
About this episode
Tyler Ramsbey discusses his transition from a cybersecurity job to starting his own penetration testing company and hacking education platform.
In this episode of The Hacker’s Cache Podcast, I sit down with Tyler Ramsbey to discuss why he quit his cybersecurity job to build his own penetration testing company, Kairos Sec, and hacking education platform, HackSmarter. We dive into the reality of cybersecurity entrepreneurship, burnout, work-life balance, OSCP and PNPT certifications, AI in penetration testing, red teaming, OffSec’s “Try Harder” culture, and what it actually takes to succeed in offensive security. If you're interested i...
People in this episode
Host: Kyser Clark
Guest: Tyler Ramsbey
Topics covered
- cybersecurity entrepreneurship
- penetration testing
- work-life balance
- AI in penetration testing
- offensive security
Keywords
- cybersecurity
- penetration testing
- entrepreneurship
- burnout
- red teaming
- certifications
- AI
- offensive security
Mentioned in this episode
Organizations: Kairos Sec, HackSmarter, OffSec
Products: OSCP, PNPT
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