Jim VandeHei’s high school guidance counselor laid it out clearly: VandeHei wasn’t cut out for college. In 1990, you could find him proving the counselor’s case emphatically, preferring beer to books and delivering pizzas to mapping out career plans. He attended a two-year school before smuggling himself into the University of Wisconsin-Oshkosh, where after a year he had racked up a 1.4 GPA and was on the verge of getting the boot.