Issa Rae Built a Hollywood Career on Her Own Terms. Next, She'll Build an Empire

It’s a Friday afternoon in late August, and Issa Rae—the creator, star and executive producer of HBO’s Insecure—is leaving the bar at The London hotel in midtown Manhattan. But before she can make her way back to her room, a nervous woman stops her. Apologizing, the woman says that she never asks celebrities for photos, but on this particular occasion, felt compelled to make the effort.