Rerelease: Issa Rae on Brokeness, Making Your Own Art, and Embracing Your Particular POV

So nice we’re releasing it twice! Today we’re revisiting Issa Rae’s Nice Talk episode.Issa Rae truly does it all. Not only is she a multifaceted entertainment powerhouse, but she also runs businesses in various industries—from prosecco to food to haircare. Today on the show, the former Marie Claire cover star joins us to talk about money, power, and style, including how she crowdfunded her early projects like Awkward Black Girl, how she overcame "grateful to be here" energy after partnering with HBO, and what it means to be boldly elegant in her style. She also tells us about her newest projects: her book I Should Be Smarter by Now and her two-part docuseries Seen & Heard. Plus, Rae shares why creativity is not the most important trait to be successful in the entertainment industry.This episode was originally released on September 25, 2025.