I don't remember. Did Kottke link to it back in the Olden Days? Apparently I joined on 09 August 2002, but I was reading it long before then. Metafilter was where I turned for news on 9/11, so even then it was a regular visit for me. I didn't read it from Day One, but certainly from 1999 or 2000.
A blog is born
This one's easy. On 14 March 2006, I askmeed for personal finance web sites. Based on feedback from the AskMe community, I started a new project. That project exploded into something more than I'd ever dreamed of. It turned into Get Rich Slowly, a popular personal finance blog, and led me to publish a book, land some magazine-writing gigs, and more. Much more. It helped me get out debt, build savings, and now, believe it or not, it's led to a travel blog. (See what I can spend my money on when I don't have to pay my credit card bills?) Matt knows how grateful I am for Metafilter's role in my life. I wouldn't be where I am today without it.