From Phreaking to Freelancing: 30 Years of Tech Adventures

If you’ve ever been banned from AOL, hacked an ISP by accident, or had a run-in with the FBI before graduating high school, we probably would’ve been friends back in the day. This is the story of how I went from a curious kid with a Macintosh Performa to a lifelong tech nerd, Linux admin, and software company owner.

Bouncing Around Before Tech

Before I got into IT, I jumped between jobs. Car sales, Kirby sales, construction, putting up billboards, and working as a waiter, bartender, cook, and manager. I never really knew anyone who shared my interests, so I just assumed my knowledge was common. Turns out, it wasn’t.

1994: First Taste of Tech: A Macintosh and Dial-Up

My journey into tech started in 1994 when I got a Macintosh Performa, which felt like pure magic at the time. But the real addiction started when I got my first internet connection, AOL.

Back in the 90s, AOL was the internet for most people. Chat rooms, message boards, emailit was all new and exciting. But just using AOL wasn’t enough. I wanted to tinker with it. That led me to my first real hacking experience.

Banned from AOL: My First “Hack”

I discovered that various extensions for AOL 2.5 could unlock hidden admin-level access. These tools let you do things like kick people from chat rooms and manipulate settings you weren’t supposed to touch. Naturally, I had to try it out.

It wasn’t long before AOL caught on and banned me. But getting back on wasn’t hard. They weren’t great at keeping track of bans. A different credit card or hopping between floppies full of free hours did the trick. Instead of deterring me, it just made me more curious.

The Underground: Macfiles, Hacking, and Phreaking

I spent a lot of time in Macfiles (later renamed Zelifcam), a Mac software piracy chatroom and mass mailing group. That’s where I got exposed to hacking, wardialing, and phone phreaking.

I devoured issues and text file of Phrack, 2600, and Cult of the Dead Cow, learning about social engineering, network security, and how systems were supposed to work (or not work). If there was a way to push technology to its limits, I wanted to know about it.

1997: Installing Slackware Linux from Floppies

In 1997, I picked up a book at Hastings that came with Slackware Linux on floppies. That was my introduction to Linux, a completely different world from the friendly Mac GUI.

It took forever to install, and once I had it running, I had no idea what to do with it. But I kept at it, fascinated by the power and openness of the system. That early experience shaped my entire career.

1996: Hacking an ISP (By Accident)

In 1996, I got into wardialing, dialing up random modem numbers to see what was out there. One day, I stumbled upon an ISP terminal. Out of curiosity, I typed root, hit enter… and it let me in.

I knew enough to realize this was not supposed to happen. Thinking I was being helpful, I contacted the ISP to let them know. Their response? Not gratitude. Instead, they were furious that a 12-year-old had hacked their system. Lesson learned: people don’t always appreciate free security audits.

1999-2000: The FBI and My High School Arrest and Getting Banned from School Computers

By high school, I was fully immersed in phone phreaking, using gray boxes to manipulate phone lines. Like any teenage kid with newfound power, my friends and I used it for completely dumb things like calling psychics and adult chat lines for free.

One day, the authorities caught up with us. The local police and FBI picked me up for questioning. I got lucky and was put in “teen court.” The judge clearly didn’t understand what I was doing, and my jury (also high school students) didn’t grasp it either. What started as federal charges resulted in a few months of community service. It could’ve been much worse, but I walked away with a slap on the wrist. Unfortunately, I didn’t learn my lesson right away. Later in high school, I was banned from using the school computers for repeating an old mistake. My high school used NetWare and never updated any of the default users or passwords. I found a share on the network that contained personal details for all students at the school. Thinking I was doing the right thing, I brought it to the system administrator so it could be removed. Instead of thanking me, he went straight to the principal and accused me of being malicious. Just like that, boom, no more computers for me. It was a wake-up call. I had to be more careful with my curiosity.

2009: First IT Job, Helpdesk to System Administrator

When I landed my first IT job in 2009, I started as a helpdesk guy at an oilfield company. Within six months, I was promoted to system administrator because I automated everything using PowerShell.

2011-2013: Rackspace, Linux System Administrator

From there, I got hired at Rackspace as a Linux system administrator, working primarily with XenServer and the VMs customers created on that infrastructure.

2013-2017: System Administrator to Applications Manager

After Rackspace, I moved on to another company where I worked as a system administrator and later as an applications manager. These years were all about learning how IT infrastructure and applications integrate on a larger scale.

2015-2019: IT Director and Burnout

By 2015, I had worked my way up to IT Director. But by that point, I was burned out. So bad that I quit without a real plan and spent a few years trying to find my place in tech without reliving the PTSD of the corporate grind.

2020-Present: Freelancing and Building a Business

Then, I started freelancing on Upwork. That quickly took off in 2020. Over the last five years, my one-man operation has grown into a 14-person team. Now, I focus on making sure we do a great job for our clients and that I do a great job for my team.

From Hacker Kid to Business Owner

Looking back, every experience, from getting banned on AOL to installing Slackware to being questioned by the FBI, shaped who I am today. The curiosity that got me in trouble as a kid is the same curiosity that helped me build a software company.

The tech world has changed a lot since the 90s, but at its core, the spirit of exploration and problem-solving is still the same. And that’s why I’m back to blogging, to document, reflect, and hopefully inspire a few people along the way.