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

Leron Gray is a man of many talents. Not getting really into computers until much later in life, but always having a creative side, he now finds himself as a pentester working from home and nerdcore rapper producing amazing beats!


Leron is currently a penetration tester and a ten year Navy veteran with four years experience as a Cryptologic Technician (Networks), focusing primarily in 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 sister 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 pyt hon could help… it could be anything you do.. .often enough to warrant not to do it manual.”
  • “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 you merit. But…”
  • “Maybe the person can’t get OSCP, but maybe they have the skills or knowledge…”
  • “The idea of aptitude… raises too many borders.”


Leron on Twitter:

Leron’s Blog:

Leron’s GitHub:

Class that Leron Is Mentoring:

Visual Studio Code:


IPython Notebook:

San Antonio’s Hackers Association:


Intro Music: Cascadia by Trash80 – (Released under Creative Commons)

Outro Music:

Getting Into Infosec

I made it on a Top 5 list!




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