I worked at Canterbury School from 2001-mid 2004, splitting my time between teaching, building tools for teachers, and IT work (networking, getting machines imaged, and yes, sigh, help desk). At the time Canterbury required all high school freshmen to take a quarter of computer programming. When I started working at Canterbury mid-year, the class was taught in Java, which had superseded C and Pascal over the years.
In the summer of 2001 Naomi and I went to LinuxWorld and attended Guido van Rossum's Python tutorial. (I think the presentation was nearly identical to the one he presented in 2002 in NYC). On the flight home Naomi started drafting what Intro exercises would look like in Python, and the conclusion was obvious: this was a much better language to teach in, especially when this was the last programming course many of our students would take. I worked on it some more when we got home, and in the fall we rolled out one section of a Python-based Intro class.
We were rolling out Linux servers running Samba as backup domain controllers, and our home-rolled imaging system was strung together with bash, if memory serves.
I spent a lot of time reading Slashdot. (Tuition dollars well spent, no doubt.) And that's probably how CC first crossed my radar.
In the fall of 2003 Mike Linksvayer, CC's CTO, posted a list of "technical challenges" on the Creative Commons blog. These were projects they wanted to do, but simply didn't have the capacity for. Things they thought would help support the ecosystem, and hoped people in the community would work on.
In a pattern that's repeated itself since then, I started poking at one to see if I could make it dance. I started with a license validator web application, and announced it in October 2003. This is in the midst of back to school, both for Canterbury and myself -- I'd gone back to college that fall, and I was in that making zone where I'd work on figuring out CGI headers while watching TV with my partner, or try to fix "just one bug" over lunch at work, and look up to realize it was 2 in the afternoon. I was having fun.