Reasons not to choose the biggest cities: 1. More traffic than you think you can handle. 2. Demographics don't match the mainstream that you will be selling t

Reasons not to choose the biggest cities: 1. More traffic than you think you can handle. 2. Demographics don't match the mainstream that you will be selling to later. 3. Competition already has a lock on those cities. I'm sure there are others as well. Edit: the Chicago/$25 billion comments refer to Groupon's HQ being in Chicago (and their Potenial IPO valuation[1]). [1] http://www.bloomberg.com/news/2011-03-17/groupon-is-said-to-discuss-ipo-valuation-of-up-to-25-billion.html http://www.bloomberg.com/news/2011-03-17/groupon-is-said-to-...