It’s been a while since we went anywhere, and the South Bay area continues its sweltering weather (66 Fahrenheit right now in Sunnyvale — how long can a person take that?), so yesterday we flew to Chicago, where we’re going to chill out for about a week.
We do this every year and, as is our tradition, we’ll spend the first few days holed up in a hotel downtown, doing nothing but hanging out, going to movies, and going to great restaurants (including, this year, Charlie Trotter’s — best restaurant in the U.S.? Discuss.). This is typically pretty much the only “romantic” vacation we take all year. Then to suburban Park Ridge for a family Christmas with my parents, my brother’s family (and this year, a broader family reunion).
The Chicago portion of the trip is always a little bittersweet for us. J. and I lived in Chicago a long time – through college, grad school (where we met) and then early clueless attempts at tech entrepreneurship together. We loved the city, but ultimately felt rejected by it professionally, and so bailed for the Valley. I don’t know how much Chicago has changed, but at the time it was not a great place to be a geek. The finance and trading industries do lots of heavy computation, and it’s pretty interesting if you want to go in the “quant” direction, which I did for a while. But to put it bluntly, even when the geek work in those industries is interesting, it’s very clear that you are playing a supporting role, and (to be blunt again) there are a lot of assholes in trading and finance – do you want to work for them? (Not, to be sure, the particular ones I worked with (Hi Chris and Jon! 🙂 ), but I knew enough to realize that they were exceptions to the rule.) And in general the attitude from the business and VC community (such as it is) toward tech ventures is consistent with that.
But I love the city, anyway, and could live there if things had been different or we’d gone down a different professional path. Yes, I know: weather. We’ve become soft and weak since we moved, like everyone else in CA is, but at the time, when we were still hardy Northlanders, the winters were not that bad. (Summers were actually worse – I would not live in Chicago without air-conditioning again…)
Tim Converse 
Hey tim, stumbled across this post, and thought I’d comment that the VC and tech community here in Chicago is pretty much as you describe having left it. There are a few great things going on: 37Signals, TicketsNow is doing extremely well, some of us are at least having fun, but mostly it’s quant stuff at hedge funds like citadel and others. Still, you can’t beat the restaurants here, eh? If you like Trotter’s 13 course degustation approach, next time you need to eat at Alinea, just about a half mile south of Trotters on halsted.