Loeb is one of the last of New York's "Our Crowd," the city's nineteenth- and twentieth-century Jewish establishment. His maternal uncles included New York Governor Herbert Lehman and Irving Lehman, Chief Justice of the New York Court of Appeals. On his paternal side, grandfather Carl M. Loeb and father John L. Loeb Sr. founded Loeb, Rhoades. And his brother Arthur founded New York City's beloved Madison Avenue Bookshop. Loeb's confessions are an open and moving account of the blessings and burdens of growing up in his family's circle of expectations.