I've had the jtauber.com domain since September 2nd, 1996. It wasn't my first domain (that was the now lost entmp.org) nor was it my first website (that was twenty years ago, in 1994) but it's been my online "home" for almost half my life.
By 2003, I'd gone through multiple technologies: static HTML, static HTML with server-side includes (remember those?), Perl scripts, XSLT.
In 2003 I decided that rather than editing files on disk and processing them to "generate" the site, I wanted something wiki-like where I'd be able to edit in some lightweight markup language directly in the browser.
I built a little system in Python. It carried over the wiki concept to basically have a page for each subject I was interested in, each project I was working on, etc.
In early 2004, when I decided I wanted to try blogging, I implemented some very simple extensions to my code to treat pages under /blog/ slightly differently. On April 21st, 2004, after a couple of people inquired about the code, I open sourced Leonardo. I liked the name a lot because it evoked the notion of a technologist's or scientist's notebook. And it didn't have "Py" in it like every other project written in Python at the time seemed to.
Content was stored on the file system with extra files for metadata.
The markup language was similar to wikis like MoinMoin but I had my own extensions like being able to link to a book on Amazon with just [amazon:{isbn}]. There was also the notion of including the contents of one page in another with [include:{wikiword}].
Some of the stuff I did (and talked about doing) in Leonardo in the couple of years that followed foreshadowed ThoughtStreams. I'll talk about that a little more as I hit those blog posts.