Should I base my start-up in Chicago, Austin, Portland or Silicon Valley?

You are not giving Chicago a fair shake. I bootstrapped one company in Chicago and raised money from local angels and funds and coastal angels and funds.

Venture funding in Chicago has become significantly easier to come by than a few years ago, and much of your analysis of the city is a perpetuation of rather old stereotypes.

Sittercity, Grubhub, Braintree, GiveForward, Fango, Scholarpro, FeeFighters, Inventables, IfByPhone, BrightTag, PVPower, Centro, Vibes, Groupon and all the lightbank companies, Pawngo, Poggled, SproutSocial, Where I've Been, Local Offer Network, SoCore, TapMe, RedFoundry, yCharts, AnalyteMedia, Appolicious, FutureSimple, RedFoundry, CleverSafe, HoneyApps all raised real money at an early stage in Chicago.

Also, I don't understand why corruption would be a concern at all. If you are a tech company you are never going to need to bribe an alderman.

Honestly, I never get these posts about "where should I go to do X…?"

Seems like a funny thing to worry about when you're in the early stages of starting a business.

I've lived in both NY and (currently) Chicago for a number of years, but I'm from Kansas City. When I go back to Kansas City I see two things:

1. People doing amazing work. 2. People making excuses for why they can't do amazing work in KC.

In Chicago and New York I see the same thing. People doing amazing work and people complaining about how x, y and z are holding them back.

If you have a great company, you could be in Boondock, Iowa for all I care. Likewise, if you're the type to make excuses, there isn't a city in the world that will make up for that.

It doesn't matter where you are, it's what you're doing that counts.

As a current Portland resident, I can say that the rain has one advantage: Your employees will have nothing else to do but stay inside and work. I know I've found myself trudging through work on multiple occasions just because it was so crummy outside. Of course, that's probably not ideal in the long term...