Issa Rae Details Her ‘Insecure’-Like Introduction To Adulthood — ‘We Never Paid Rent For Six Months’

On this episode, Sanders asked the creator of “Rap Sh!t,” as means of inspiration, to introduce the audience to broke Issa. At that moment, she noted that it wasn’t until she got to Harlem that she finally realized how broke she was initially.

“I was in Harlem, and I had just graduated and gotten a stipend to move to New York. And I thought I was balling. It was a $6,000 stipend, and I was living in a slum. I didn’t know I was,” Rae described on the podcast. “This random, like, Jewish dude who must’ve been like 24 had shown me this apartment, and I was tasked with finding it for another girl I knew at Stanford, a Black girl.”