In the late 1880s, a successful Italian immigrant to Chicago made a return pilgrimage to his native village and on board ship other Italians pressed him on the secret to success in America. He replied, "One rents a store, sets up a lunch counter or some other business, secures customers, and if one is smart, he becomes rich." [1] Many Italian immigrants took these steps, and if they did not become rich, they established themselves in a variety of profitable businesses.

The easiest point of entry into Chicago's commercial life at the turn of the century was to work as a peddler up and down the streets and alleys of Chicago's neighborhoods. Jobs as delivery drivers were also plentiful. Italians quickly cornered the fruit and vegetable trade in Chicago, and peddlers careful with their money might move up to open one of the many small "mom-and-pop" groceries that filled Italian neighborhoods. Restaurants and saloons, as well as specialty food and wine stores, were logical extensions of this Italian predilection for food and drink.

Italian small businessmen also dominated the local barbershops, which served both its utilitarian purpose and a social function as a gathering place for neighborhood men. And increasingly Italians were seen in a variety of local small businesses, from pharmacies to jewelry stores, from bicycle shops to shoe repair businesses. And as businessmen accumulated capital and resources, they expanded into manufacturing enterprises, whether small-scale like the Near West Side's Vesuvio Beverage Company, or the large-scale enterprise of the Chicago Macaroni Company.

[1] Quoted in Rudolph J. Vecoli, "Chicago's Italians Prior to World War I: A Study of their Social and Economic Adjustment," Ph.D. dissertation, University of Wisconsin, 1963 p. 14.