38Jayson E. Street

“If you want to get a really good red team job and be effective as a red teamer, understand all the details of how the blue team functions, and that will make you a way better adversary.”

Twitter: @jaysonstreet

Jayson E. Street is a co-author of the Dissecting the Hack series. He is also the DEF CON Groups Global Ambassador and the VP of InfoSec for SphereNY. Jayson has spoken on a variety of information security subjects, including events at DEF CON, DerbyCon, GrrCon, and several other cons and colleges.

How did you get your start on a red team?

I believe I’ve always had that red team mentality, even when I was in physical security, patrolling a new building or starting at a new site. I would always look at the defenses and check to see whether the camera placements were correct to make sure that the perimeter was secured. I made sure that the doors were locked and there was no way to circumvent the door, so I was always thinking with that mentality—how I would break in and be the bad guy. I didn’t actually start doing the official red team role until probably midway through my career. When I started looking at the physical aspects, partly being inspired by watching some other red teamers give talks at conferences, I realized, “Wow, that’s a whole other avenue I could start looking at,” so I started doing red teaming in my organization. They were very ...

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