When Toby Alfred was applying to college, her mother told her, “You figure out the best place you can get into and I’ll figure out a way to pay for it.” In retrospect, she says, that was “a tremendous gift.” Neither of her parents were college graduates; her mother was a bookkeeper; her father worked as an office manager and money was tight. Alfred got a scholarship to Carnegie Mellon and took out loans to pay for her MBA from the University of Chicago.