In this episode of The Keyboard Samurai, host Wil Klusovsky (aka Wil Klu) sits down with renowned ethical hacker, author, and mentor Philip Wylie — a legend in the offensive security community.Philip shares his journey from IT admin during the dot-com boom to teaching penetration testing and mentoring the next generation of cybersecurity professionals. Together, they explore how modern pen testing has evolved, why assumed-breach testing is critical today, and how M&A (mergers and acquisitions) pose unseen security risks.
💡 You’ll learn:
→ Why pen testing isn’t as simple as “breaking in” anymore
→ How assume-breach scenarios reveal real organizational risk
→ The security pitfalls hiding inside M&A integrations
→ Why mentoring, teaching, and community are vital for the next wave of cybersecurity talent
→ How ethical hacking has changed — and why it’s never been more important
Whether you’re a CISO, security leader, aspiring pen tester, or just curious about what goes on inside the hacker mindset, this episode will leave you with practical insights, industry wisdom, and a renewed sense of why mentorship matters in cybersecurity.
Find Phil: https://www.linkedin.com/in/phillipwylie/
https://www.youtube.com/ @PhillipWylie https://x.com/PhillipWylie
https://www.instagram.com/phillipwylie/