A combination of:

• I was very curious about computing and trying different applications
• I liked customizing and tinkering with my setup: Launcher, window manager, icons, etc.
• I was a poor teenager

On the windows side, there were neat apps like Stardock Windowblinds, for the most part, everything was paid and expensive for someone with no disposable income.

Mind was blown when I realized everything I wanted was available for free! My first install was actually from a CD that came with a book I checked out from the public library

Would be hilarious if he walked into a job interview and got grilled about it. “yeah, so it says here you worked on the web? do you have a portfolio? what frameworks did you use?”