I had built my own news handling systems via the SMF forum software. But that program was never intended for the purpose of handling news, and the interface for it was very awkward.

I saw recommendations online for using various bits of software for this. The most common recommendation was for Joomla. But WordPress looked much simpler to work with and was growing in popularity, whereas Joomla looked like it was on a downward trajectory. Apparently I picked the winning horse in that race :) Then the popularity of WordPress exploded and I've been riding that wave ever since.

WordPress 2.2 was the first one I installed. I installed it on my personal site when version 2.3 came out and it's been running on it ever since.

I probably would have moved all my personal stuff off of WordPress a while back. I'd prefer to custom build my own stuff now, as I can make it do exactly what I need it to do and nothing else. But I keep using WordPress since it's what I use in my professional life and it's useful to demo that I use the product myself as well as work with it for a living.