I got out of the Army in 1992, and started working for a rather large rent-a-car company. I got hired because they were deploying a VSAT satellite network to connect all of their offices. Well, in 1995, our satellite gear vendor's control software converted over to run on SunOS 4.1.3U1, so we bought a bunch of Sparc IPXs, and a Sparc 20 as the server. (as an aside, the Sun pizza box is one of the best case designs ever...)
I was helping/learning from our sysadmin, basically being his minion. Old gray-beard, and the best piece of advice he ever gave me is "I don't care what editor you prefer, you had better at least learn basic functionality of vi...Because when the place is on fire, barbarians are at the gates, and you are in single user mode, that's all you're going to have." Well, he went on to another department, and I volunteered to take over sysadminning the network. The company didn't want to send me to training, so I decided to go it on my own. I couldn't afford a Sparc box (ironically enough, I now have a sparcstation 1+, 2 sparc 20s, a couple of ultra-5s retired in my basement that I can't give away), so I started looking for an alternative. A buddy of mine recommended Linux, and gave me a Yggdrasil book, but in the end, I downloaded and installed the 50 floppies of Slackware 184.108.40.206 (kernel 1.2.3) that I dual-booted with either OS/2 Warp or Windows 95 on my 386DX16. Learned quickly how to compile the kernel, and quickly upgraded to 1.2.8. (kernel compiles took 4 hrs on my hardware)
Ran Slackware, and when RedHat 3.0.3 came out, started playing with that. I ended up losing a hard drive, and flipped a coin. RedHat won. So windows or os/2 and Slackware were no longer welcome on my hard drives.
I stuck with RedHat until 6.0 (circa 1999?), when the quality control was at it's worst. Consistent problems, RPM hell, etc, contributed to my dissatisfaction. At the time, the RH 5 series was arguably the pinnacle of the RH distro. Since then, probably 7.3 and 6.2. I still know of companies that are running those two releases...
So in 1999 or so, I got tired of RH, and had a couple of Debian Devs that worked in my group. They walked me through a Debian install (dselect, pre-apt), and I have been a happy Debian user. I strayed and decided to try out Ubuntu, I guess, around the days of Feisty Fawn. When Gutsy came out, encryption was broken in the installer. That, combined with other things, like the whole "moving the buttons to the left" controversy, and that was the period that you had to nuke-and-pave between releases, I went back to Debian, and there I have stayed. I'm one who does a nuke and pave every 5 to 7 years when hardware or architecture changes make it a good idea. I started running Debian on my workstation in 1999, and have done complete rebuilds maybe 3 times since then. Oh, I've played with other distributions, mint, fedora, opensuse, but they are mostly done in virtualbox these days, and we do run Ubuntu server at work.