The steady life only gets you so far, but in the end, the pragmatism is both Chicago's greatest asset and its greatest liability. Which really is the entire problem with the Midwest Mentality. Midwesterners have their priorities straight, but nothing generationally disruptive comes out of being conventional.
So you'd rather have the Valley where "businesses" have millions of users but no path to profitability than the Midwest where pragmatism requires you to make money? I think the latter idea is actually quite disruptive in Silicon Valley.