Today, I have the privilege of sitting down with a remarkable individual who I have been friends with for a while now, a former armored recon patrol commander, she has traded the battlefield for the digital frontier, wielding her skills in C# and Python to fortify systems against potential threats.
But that’s not all—beyond the lines of code and encryption algorithms lies a fascinating personal story. Embracing her authentic self, our guest is a proud trans woman who walks her own path, challenging stereotypes and inspiring change. Known to embark on a daily 21 km hike, she brings the same resilience and determination to her professional endeavors.
Leigh is such a lovely woman who I have been following along with for a while now since she started training with Occupy the Web.
Hope you enjoy the interview as much as i enjoyed giving it.
Can you tell me about your experience as an Armored Recon Patrol Commander, what were some of the tasks and things you done in the role, I am always fascinated by the military as an anti-monarch in the UK it’s not something I ever would have considered?
I was an armoured crewman in the Canadian forces for 15 years. I served as an armoured reconnaissance crew member in Yugoslavia, and as a leopard main battle tank commander in Afghanistan. I ended my career as an armoured recon patrol commander.
How did you transition from being a military commander to becoming a Red Team hacker?
My last tour in Afghanistan was particularly rough. Living with all the humans I had killed and 10 months of war; I was diagnosed with PTSD a year after I got home. Suddenly I was a civilian again, not adjusting well at all. At my lowest my once supportive spouse told everyone I was trans (was living as a man) and filed for divorce. I lost everything it felt at the time.
Green’s harbour the town I was living in gave me nothing but harassment, threats and bullying for being trans. I had no family outside of parents, who I was trying to appear strong for. In that total isolation I started programming.
I did a C# bootcamp and fell in love. Suddenly I was creating things instead of destroying as I had done all my life. Out of nothing more than my imagination and VS code. I took a python bootcamp and that’s when my programming really took off.
I started building hacking tools just for the coolness factor. It was just a fun puzzle for me. I found myself making simple viruses and malware that I would share on #100daysofcode on Twitter. It started getting a lot of attention.
I applied for university and got ready to start software engineering. However, with PTSD and the abuse I was going through in my “community” my doctors and I decided it wasn’t a good time. Suddenly the modular nature and self-study nature of hacking really appealed to me. I was approached by OTW at that time and began his series of lectures. I haven’t looked back.
What inspired this change in career path?
It’s kinda who I was before I joined the army really. I was a nerdy 17 yr old. Editing our cog files in Jedi Knights to make our own cheats. Using CdC Back orfice to hack our friends. Ping attacks on ICQ. Then I ran off and joined the army at 18.
What programming languages, specifically Python and C#, do you find most useful in your hacking endeavors, and why and also do you know PowerShell as I am currently using both PowerShell and Python and want to take one further but can’t decide which one?
Python, and bash is mostly what I use regularly. Bash I’ve just been learning on the fly out of necessity. Ruby comes up quite a bit with exploits. C for Ghidra.
Can you share some interesting or challenging projects you’ve worked on as a programmer or hacker?
I helped Ukraine on some projects that I’m very proud of. That’s the highlight for sure.
How has your identity as a transwoman influenced your experiences in the tech and cybersecurity fields?
I joke with other trans women hackers that being trans really should never be an issue. If you know my identity red teaming; I’ve really messed up. Not good!
Honestly, I call industry experts friends and have never experienced transphobia from anyone who mattered. I truly believe just by nature of the infosec field; people must be open to change.
I’ve been thanked by trans hackers who see me representing out there. I give them confidence to do the same. I have very conservative people reach out to tell me they’ve changed their minds about trans people due to my hacking.
Being trans rarely comes up in my real life. I’m living a very happy life as a straight woman. All I ever desired in life. I’m also a huge nerd first and foremost. I identify as a hacker.
Programmers were the first people who showed me I could actually have a place in the world as trans woman. I could have dignity which is important to me.
What aspects of Viking culture or history resonate with you, and how do they influence your life today?
I come from a long line of boat builders of Viking descent. I’ve built two myself. It’s a culture of exploration and conquest. Science. I’ve continually awoke on battlefields for a large portion of my life.
What led you to become interested in cybersecurity and ethical hacking, we share a friend in common and I am SO jealous you are getting taught by him but how did you come to be trained from Occupy the Web?
OTW approached me about joining his platform 15 months ago and I haven’t looked back. He taught me everything I know. His classes are amazing and the rabbit holes I find myself tossed down into are the absolute best.
How do you stay up to date with the latest trends and developments in both the cybersecurity and programming worlds?
Hackers arise discord. Reddit is probably the best source, surprisingly.
What advice do you have for individuals interested in pursuing a career in ethical hacking or cybersecurity?
I would focus on the hacking itself before the certifications. Share what you’re doing with the tech world online. Networking on twitter has landed me all my roles. I honestly don’t even a have resume.
Be wary of how much mental energy things like news media can take away from you. I found me knowing about a major world event didn’t do anything to fix it. I just wasted my own mental energy. Although hard sometimes; I avoid media and just focus on hacking and studying. Things that develop and build me up.
Are there any specific tools or resources you recommend for aspiring hackers or programmers like is Python a must?
I think having some web app programming and backend developer skills is a must have for hackers. When someone starts learning Linux and networking along the hacking journey, they should start programming too. I’ve found my projects programming with MySQL for example really helpful.
What are your long-term goals and aspirations, considering your diverse background and skill set?
Red team at a major company with flexible hours so I can hike a few hours in the morning. 150,000 a year. A job where I can stay constantly studying and practicing the cutting edge of hacking things.