When you think of a family business, one of two images probably comes to mind: either the mom and pop shop around the corner or the dysfunctional family from “Succession.” But actually, “it could be anything,” says Jennifer M. Pendergast, family enterprise consultant and professor at Northwestern...

Tracking down the oldest family business in the city is not as easy as it seems. The city’s business records only go back to 2002. Time for a fishing expedition.