With 20+ years of cybersecurity work, Tom unpacks the complexities of penetration testing, discussing the roles of vendors, practitioners, and technological advancements.

He also shares his perspective on what makes a good pentester, the value of mentorship, and the ethical challenges in this line of work.

Explore this conversation to learn:

• How pentesting changed over the years and who’s shaping it [03:02]
• How to avoid burnout and deal with imposter syndrome [09:13]
• Why he seeks and values mentorship for personal and professional growth [19:44]
• The importance of constant learning and networking with your peers [23:23]
• How compliance brings down the value of pentesting and what to do about it [30:04]
• How cultivating range can help you in your pentesting career [37:24]
• How to set healthy boundaries to protect your health [41:11]

This episode with Tom is a must-listen if you want to learn how to showcase your work and elevate your thinking and tactics.

• Tom’s personal website
• Tom on LinkedIn
• Tom on Twitter
• The Shared Security podcast
• The People Hacker book by Jenny Radcliffe
• Tom’s journey from offensive security to leadership at the Phillip Wylie Show
• Ethical hackers and the legacy of the hacker manifesto for Cyber Empathy
• Tib3rius
• Jason Haddix
• Dave Kennedy