Normally wouldn't self-reply, but I felt I could do a lot better than what I'd just written. I grew up in Chicago and attended Urbana-Champaign (UIUC) engineer

Normally wouldn't self-reply, but I felt I could do a lot better than what I'd just written. I grew up in Chicago and attended Urbana-Champaign (UIUC) engineering for college. I headed out to SF to see what all the hype was about. I also have a long-term girlfriend in Chicago. I've flown back and forth between the two cities 12x in the past year, so I feel I have some room to comment on the differences. Chicago and SF are both great cities. Both have huge populations and deep business networks spanning back generations. Also, both have plenty of capital. Chicago's capital tends to be old-money, industrialist capital, whereas SF is more pro-risk and institutional, but both have money. And I actually think Chicago has a stronger overall "business" culture with numerous family-owned small businesses dating back to the 1800s. Whereas the SF tech crowd always chases what's new and shiny, I think there's a much greater willingness to invest for the long term and build patient, long-term empires in Chicago than in SF. Also, while SF/Bay Area is often praised for its deep engineering talent base, Chicago has quite a lot of engineers. People often forget it's been a rail and telecom hub for 150 years, three major financial exchanges (CBOE, CME, and CBOT) call it home, tons of broadcasting and media (Ogilvy) types work there, and lest we not forget, patio11, tptacek, and 37signals all grew up there. What Chicago lacks is entrepreneurs. Eric Ries hits the nail on the head calling entrepreneurship a "management science". The process of systematically identifying opportunities, measuring and de-risking them, and then putting a team together and raising capital isn't as common in Chicago as it is in SF. I think the Bay Area has achieved a critical mass at this point, where nothing intrinsic about it leads to entrepreneurial success (and in fact, much about California is downright hostile to business) -- but everyone's here these days. From my office in Soma, I can walk 3-4 blocks and be at Crittercism, Twitter, Square, Stumbleupon, Lyft, Zendesk, Smule, Coinbase, and dozens more. The sheer proliferation of people, and of entrepreneurial expertise, means the density of opportunities coming from here is unrivaled, anywhere. I may yet move back to Chicago but it will come at a cost. I'm encouraged to see Lightbank get more SV press/mindshare but let's not kid ourselves; it's hard to be a one-city fund when your city isn't a global destination for software entrepreneurs the way it is here.