VF Hive editor Jon Kelly begins his conversation with Graydon asking how he got his start at Vanity Fair. They discuss Carter's early days at Spy magazine and The New York Observer, and the initial offer from S.I. Newhouse to come to Vanity Fair.

Carter describes the challenges he faced in the first two years at the magazine, and how he worked to align with the staff. He reveals the techniques he used to reinvent the magazine, despite the lack of any real plan out the outset. Carter also talks about the origins of Vanity's Fair's famous Oscar parties, as well as the magazine's iconic Hollywood issue. He describes how the parties grew over the years, and how they and the Hollywood issue became embedded in the culture.