In the trite bit about what Gary was told to wear to the photoshoot, Howard tells him that when he worked at some advertising agency (how long did Howard work there?), his boss told him to show up for work in a jacket and tie. Hasn't Howard spent 4 hours a day for the last 30 years bragging about how his success is due to the fact that he never listened to any boss he's ever had? So, it's ok for Howard to be a "rebel" and reject management suggestions and directives, but when one of his staff does it (Benjy, anyone?) they're destined for failure.