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Leron Gray - From Navy E6 to Pentester, SANS Mentor and Nerdcore Rapper!

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Leron Gray is a man of many talents. Although he didn't really get into infosec until much later in life, he always had a creative side. He now finds himself as a pentester working from home and a nerdcore rapper producing amazing beats!


Leron is a penetration tester and a ten-year Navy veteran with four years of experience as a Cryptologic Technician (Networks), focusing primarily on offensive cyber operations. He holds a Bachelor's degree from Dakota State University in Cyber Operations. With a passion for Python, he loves automating tedious daily routine tasks for efficiency and considers himself to always be in a position to learn more and pass on knowledge. He always enjoys competing in as many Capture-the-Flag events as possible and also often performs as a nerdcore rapper.

Leron currently holds eCPPT, eWPT, GPYC, GPEN, GAWN, GCFE, and GICSP certifications. He also maintains a blog and maintains an active Twitter discussing music, information security, and wrestling.


  • Went to a high school that made you choose majors

  • Grew up poor, was not allowed to go out much

  • Technological learning came from school

  • Didn't really get into computers until he was 25

  • Has been in music since Jr. High School (Marching band, jazz band, and concert band... all the bands)

  • Networking is the biggest thing that Leron says would help

  • Leron offers his passionate opinion on "aptitude" (it's a pet peeve of his)


  • "I learned a lot... I made sure not to waste any opportunity for learning."

  • "Job searching, in general, is a pain."

  • "I don't think I would be where I am right now if I hadn't gone out and made that effort."

  • "One of the big deals that people had were degrees. I wasn't really sure why; I have 10 years of IT/Cyber experience."

  • "It turned out the company no longer owned that server. Their DNS was still pointing to it though."

  • "I took Java in high school and was really bad at it and I found out everyone is bad at Java, so it doesn't really matter."

  • "It's so much easier to learn when you have a problem to fix."

  • "It's not even just information security that learning Python could help... it could be anything you do... often enough to warrant not to do it [manually]."

  • "Nobody does a CTF and expects not to learn something by the time they leave."

  • "Job searches shouldn't be like that: they should be based on your merit."

  • "Maybe the person can't get OSCP, but maybe they have the skills or knowledge."

  • "The idea of aptitude... raises too many borders."


Getting Into Infosec

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Getting Into Infosec

Interviews with people who have transitioned and got jobs in #infosec and #cybersecurity so you can  
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