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Jim Broome of Direct Defense has been doing red teaming since before it became a term — back when a "pentest" meant $25,000, no questions asked and walking out with a server under your arm. In this episode, Jim shares wild stories from decades of ethical hacking, including breaking into major tech companies, causing a cardiac event during a physical penetration test, and why he believes soft skills trump technical knowledge for aspiring red teamers. Learn why most companies aren't ready for red teaming, how to transition into cybersecurity from unexpected fields like education or event planning, and what it really takes to succeed in offensive security.

0:00 - Intro to legendary red teamer Jim Broome
1:00 - Cybersecurity Salary Guide
2:58 - From BBS and ham radio to cybersecurity
7:07 - Evolution from network admin to red teaming
12:02 - GPS hacking and testing inflight entertainment systems
15:31 - Hiring teachers and event planners as ethical hackers
23:36 - Breaking into Symantec and stealing servers in the 90s
28:33 - Physical pentest causes cardiac event
34:06 - When companies should (and shouldn't) hire red teams
39:44 - Why red teaming is "a punch in the mouth"
44:09 - How AI is changing offensive and defensive security
48:12 - Essential skills for aspiring red teamers
50:39 - The groundskeeper who got domain admin
52:18 - Best career advice: Be humble

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From stealing servers to saving lives: Working in red teaming | Jim Broome