From Ink to Circuits

I still remember sitting in my friend's room in his parent's house sometime in the late 90's listening to NAS as we all drew in each other's "Black Books." The Black Book was a traveling graphic novel that the owner would start, and other artists would follow until the book was full. Black Books are such an underground subcultural aspect of graffiti not a lot of people are even aware that Black Book artists are also graffiti artists.

Black Books were magical in the way that they would always find their way back. There was a built-in system that made this possible. When you got someone's book you gave them your book. If you didn't give their book back then… well you can finish that thought. This night was so meaningful because my friend had been away at college and I was recently back home from basic training.

We were always an odd friendship, an Irish redhead in Paterson New Jersey and a curly haired hip-hop skateboarder. Graffiti and Underground hip-hop were our common ground. We loved graffiti, but we also loved our sleep and not getting arrested so Black Books where all we did until the one time a year when the city allowed the basketball court walls to be painted.

Spending time with a few close friends was already great, but the night was about to get better. Computers were not a common thing for us at that time, which would explain why I didn't notice his in the corner. I was slumped over a page with my fitted Yankees hat resting just below my eyebrows when Terra stepped over me to get to his desk. I assumed he was going there to draw until I heard the clicking of his keyboard.

In the city if you are not told to look at something, you don't see nothing… I didn't bother looking and refocused on Mad Skillz — Nod Factor which was scratched into something else on the new DJ Kid Capree mix tape. Eventually Terra called me over and showed me what he was working on. He did a real 3D graffiti mural in Bryce 3D. He had real graffiti that he moved, and it was instantly a drug to me.

I had gone into the Air Force as a mechanic, Environmental & Electronics Systems Specialist for the KC-10 airframe. It was worlds away from residential or commercial construction, but I convinced a guy that owned an electrical company it would be enough to do anything they could do and more. I didn't know it then but that was the first real indication that I have a way with words and selling. It wasn't the safest work, and I would often find myself in NYC working under the table electrical jobs and hiding from the Electrical Unions.

All my work was for one goal… a computer I could do art on. I didn't spend money on anything fun and finally had enough to buy a Mac Power PC. I still laugh at how little I knew about computers. I ordered it from a magazine using my Military Star Card. The weeks that passed made me feel like I got scammed, guess that's why I'm still impatient with online purchases.

I raced over to my then girlfriend, now wife's parents place. I needed the computer to be signed for so I had it shipped to her father's job because he worked in a mailroom. When he got home from work and handed me the box, I must have had a look that stained his memory because he just smiled the biggest smile I had ever seen from him. I carefully opened it and smelled everything. The box was so big I thought that the monitor and keyboard was in it too. I was wrong, it was just the computer.

Not having a monitor, or keyboard meant that all I could do was turn it on and watch the fan spin up, listen to the transformer power the motherboard, and enjoy the blinking lights. The following day my girlfriend called me to come over for dinner and let me know that her father wanted to talk to me. Hearing that is never a good thing, so I steadied myself for a bad night for something I did that I was unaware of, but when I walked into their house I saw that same smile again, then he said "Look behind you." He had gotten me a monitor, keyboard, and mouse. I almost broke out in tears. It took me three trips to get all the gear back to my place.

I eventually got fired from work because I was too engaged with my computer. It didn't come with any of the programs Terra had… Matter of fact, it only came with CDs to restore the OS if it crashed. Through opening everything I could click that would open I found the modem, then Terminal and the fateful word "help" that opened a new world to me. From help I learned a command called man which would eventually unlock the operating manual and user guide in command line. I read everything that popped up.

I learned how to operate the modem, then how to connect to the internet, then I learned code cracking that complimented phreaking. Eventually I had all the programs I needed, eBooks weren't a thing at that time, but I had more .txt files than my computer could store. This taught me another skill of file system management. I contributed as much or more than I consumed, and art turned into my second love, the new first was cracking. It was never about getting or pirating software it was the rush of seeing the login prompt change to an application window.

Most times it was friends sending me things they were making. Today this would be called application pen-testing, but back then we never gave it an official name. I eventually started working again and bought Photoshop, PageMaker, Illustrator, and Flash. Word got around that I would design for club tickets, this put art back into the number one slot and I lost contact with all the crackheads I knew.

Somewhere along the lines I became a father and the Air Force Reserves turned into Active Duty in October 2001. I hadn't understood that the skills I learned would be unforgettable foundations for what I do today. I was a young father with a new marriage that never came with a honeymoon who was now working wartime hours without ever leaving New Jersey.

The hours I once had to learn and test turned into a broken me, broken marriage, and forgotten skill. Had it not been for a career ending injury I got while working on the flightline I would never have found my way back into the world of computers and eventually cyber security. The cartilage behind my kneecap was blasted away but x-rays never saw that. I was taken off the flightline for two years before I was retrained into cyber, and I had to fight tooth and nail not to get discharged to secure the retraining.

I skimmed over the natural skill of selling earlier, and I'll tease it again now. I knew how to sell myself. I had been accepted into Parson's School of Design, had an impressive graphics design portfolio from club flyers and magazine work, plus I knew how to work computers. This led into me getting special permission from the Pentagon to work on maps, but a series of events and politics killed that dream so in the heat of anger I told them if they wanted me out of the Air Force they'd have to fail me out.

A few days later I'm called into the education and training building and handed orders to Keesler Air Force base to learn information systems. The person handing me the papers had a smirk I wanted to punch of their face and said "We won't be seeing you again. Wasn't nice having you around." I missed honor grad by two points. They were right, I wouldn't be going back to New Jersey.

After getting out of the military I chased everything that was interesting. My first job was in mobile telecommunications where I helped transition a major provider from analog to digital. Then I moved into a startup that went under during the global financial crisis. I ended up working as a cook until a random call from a friend led into a job working on high-speed low-latency networks. After that came IP routing and switching. That last one kept me interested enough to get a few really important certs. Life changed the day I went to BSides. As soon as I saw that all the work I was doing on the perimeter did nothing I left everything I had worked on for a decade to commit to cybersecurity.

I had worked my way into being known as the go-to guy for all things perimeter network security when I got a call to join a team selling Managed Security Service Provider services. They had heard that I had a way with getting people to understand really complicated technical problems in easy-to-understand ways. The line that sold me was "we're on a Rocketship with blinders." This was my first corporate sales job, and it changed my life forever.

Fighting with trolls, and all the other online chaos of the early internet trained me in ways that school educated brain bullies couldn't compete with. I earned my stripes, literally and figuratively, I knew that my flight leaders didn't care about "nerd nob shit" and figured CEOs would be no different. Getting into professional sales teleported me back to my room where I saw the daylight leave and comeback as my trusty command line and I floated through all the emotions you could imagine before sleep finally forced me to lay down.

Twenty-some-odd years later I find myself still with the same curiosity of a city boy who didn't know you need a monitor, mouse, and keyboard to go along with the computer. The self-confidence of a ghetto graffiti skateboarder stayed too. As I type on a DYI split-key Ortholinear keyboard I soldered together with the skills I learned as an aircraft mechanic, programmed using what I learned reverse engineering network exploits, and the Carpal tunnel syndrome from all of those collective years I'm only certain that I will never stop learning, because the more I learn the more I know that I still don't know shit!

Originally published at https://thesuccessfulfailure.blog on August 6, 2026.