“Penetration testers like myself are generally jacks-of-all-trades.”

Twitter: @DHAhole

If you were given the opportunity to tell the world your story in 100 words or less, what would you say? Would you focus on the challenges you’ve overcome and highlight your accomplishments? Or, would you use the platform to advocate for a cause you support? This is the privilege I’ve been granted as a contributor to this book. My choice is to turn the mirror on you, the reader. How would you like your bio to read? Now be that person! If you still want to know my story, then DM me or engage with me in real life.

How did you get your start on a red team?

While I’ve been a hacker my entire life, I started performing security assessments professionally in 1995. My progression has been somewhat typical, transitioning from vulnerability assessments to pentesting to red teaming.

My origin story begins after separating from the Air Force in 1994. I had been stationed overseas, and upon returning stateside everyone was talking about the World Wide Web. The consensus was that it was going to be the next “big thing,” so I signed up for a dial-up account through a local free-net. I had used computers to access bulletin boards as far back as 1982 and was excited to explore this newly connected world that had passed me by while I was in the military.

Having a hacker mind-set, I started ...

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