HN user
Their VC firm is Lightbank is run by two sleazy people. They are the same people behind Groupon. Their founders are notorious for their sleazy tactics, which are solely aimed at scamming investors out of their money. Never work for a company or get investment from Lightbank.
I should clarify. It is more the mentality of quick cash at any cost. This style of business can work in some work under some circumstances.
Orbitz does some cool stuff, but it isn't a startup. It was a spinoff from various megacorps.
37signals manages to work within the Chicago paradigm. However, they are run more like a small business than a high-growth startup.
Grubhub would be more a Chicago success story.
Groupon is the typical Chicago-based startup. After experiencing enough sleazy startups in the mold of Groupon, I decided I've had enough with Chicago. That type of business plan is typical of many Chicago startups.
The same investors behind Groupon are funding many other startups. They've got plenty more ponzi startups waiting in the wings.