Kev sits down with Emmy and Golden Globe nominated actress, writer, and producer Issa Rae for a hilarious and honest conversation about mistakes, growth, and resilience. Issa opens up about overspending as a young creator, her fear that success can disappear at any moment, and the importance of continuously investing in herself.

She also reflects on her pilot, I Hate L.A. Dudes, calling it “the most devastating thing ever,” and shares the invaluable lessons it taught her. To wrap things up, Kev confesses that he once auditioned for Insecure and got rejected.