John says he's always relied on his sister, Caroline Kennedy Schlossberg, even though she did boss him around when they were younger. "We're obviously very close. As a younger brother, you look up to your sister. I was the 'man' of the family, as it were," he says. "I feel so lucky that I have such a close relationship with her."
Like John, Caroline has also worked in publishing. She interned for the New York Daily News and wrote for Rolling Stone. With Ellen Alderman, Caroline co-authored the 1995 book The Right to Privacy.
John says the clash between privacy and fame is a topic he and his sister know all about. "We're used to a certain degree of being watched," he says. "I understand that there's interest, and certainly that interest has given both of us great opportunities, so I can't complain too much. Sometimes I wish it wasn't always that way, but then you wouldn't have invited me on your show if I was just somebody else."