Being from Chicago, reading this was great. But I was wondering:

"Mr. Leshner thought MelonCard wouldn’t be able to put together a deal in Chicago nearly as fast: “Chicago moves slower. It takes seven meetings (to make a deal), and there’s more of an old-school focus."

Why do you think this the case? Is it Chicago's financial background? Is it the Midwest thing? What keeps it from being one of the startup hubs? All the factors are here: Close to excellent universities, tons of money floating around, culture, etc. (maybe not so great weather). People used to say that it lacked a big, successful startup to act as an anchor, now we have Groupon. So what gives?