First off, congrats on building a site that a lot of people use and respect. I've definitely heard of it and I'm not from Chicago, so it must have gotten coverage somewhere.
The first question is probably a dumb one: Have you actually asked any of the journalists you work with to get you some coverage?
Also, you may have some success following up with the many reporters and bloggers who are covering the whole "new journalism" and "death of newspapers" beat. Talk to Dave Winer (http://www.scripting.com).
You're in Chicago. Do you have any contacts at Medill? Reach out to them and do a partnership ... you should definitely get some coverage that way.
Thanks. You've probably heard about me on Hacker News. I post here way too often.
A few notes:
1. I've asked a few times, and sent out press releases now and then. It's an intellectual challenge though for me to pitch people I consider my friends. Frankly, I think it's unethical and it puts them in a really tough spot where I'm just another person asking them to write about them.
2. Funny you should mention those cats. I've sent a few of those guys updates on a regular basis over the last 16 months, after all, I'm trying something new and seeing some results, but I've never heard back from any of them. I've not tried Mr. Winer and will send him a note, but I've grown pretty skeptical as to whether the "death of newspaper" guys are actually interested in new ideas, or just ideas that conform to their own. Part of the reason I spend so much time on Hacker News is because the journalism community isn't so interested in startups, but in saving their existing brands in my opinion. I don't really fit into that. I've got more in common with the Bingo Card guy then with someone starting a non-profit news organization supported by rich friends of his and foundations.
3. I went to Medill and consult for them on occasion. For this reason, they've more or less said their student reporters can't write about me, though I guess I made the alumni magazine this month (LOL). The school's had me in to speak to students pretty regularly, which has been a great source of interns.
Try some more to get a story in the Northwestern paper (or UChicago, UIC, etc.). You probably know some people who go there--get them to contact their friends who work at the paper.
I've seen lots of stories that originally got picked up by college newspapers and then appeared in the NYT, SJ Mercury News, etc.
The first question is probably a dumb one: Have you actually asked any of the journalists you work with to get you some coverage?
Also, you may have some success following up with the many reporters and bloggers who are covering the whole "new journalism" and "death of newspapers" beat. Talk to Dave Winer (http://www.scripting.com).
You're in Chicago. Do you have any contacts at Medill? Reach out to them and do a partnership ... you should definitely get some coverage that way.