In 2011, Los Angeles–based writer and comedian Issa Rae launched the YouTube web series The Misadventures of Awkward Black Girl. Shot on a budget and starring Rae as J, a tomboyish office peon with a penchant for profane rap music and a tendency to get into severely awkward social situations, the show became a sleeper hit, garnering nearly a million views on the strength of its low-budget charm and wry narration courtesy of Rae.

With the show’s success, Rae made a bunch of 30 under 30 lists, founded her own web series production company, and nabbed a pilot order for a new show, Insecure, at HBO. She’s also—following in the vein of other hyphenate comediennes before her—written a memoir, The Misadventures of Awkward Black Girl, available now.

Written in the same self-deprecating, invitational tone of soon-to-be peers Mindy Kaling and Lena Dunham (who both contributed dust jacket blurbs), the book’s an easy-to-read compendium of short essays about ’90s chat rooms (“I was a cyberho”), trying to be cool in high school when you can’t dance (“On a scale of Michael Jackson to Drunk White Girl, I come in at Drunk Black Girl”), and unwanted weight gain, among other things. (It’s also surprisingly frank about the dissolution of her parents’ marriage.)

Friday night, Rae sat down with local writer/live lit titan/hilarious woman Samantha Irby—a delightful pairing sponsored by the folks at Women and Children First. The two chatted it up at a sold-out reading and discussion at the Swedish American Museum.

Here are five highlights:

On the success of Awkward Black Girl

“I knew a network channel wouldn’t go for [the show], so I hit up my best friend and was like, ‘you’re my best friend, you have to help me.’ After we shot the first episode, people began to see it as a tangible thing and they were ultimately willing to pay. Kickstarter helped a lot.”

On Rae’s new HBO pilot Insecure

“It’s in progress. We’re locking down a show runner and director. It’s close to my life—about the trials and tribulations of getting closer to 30 in L.A.”

On fear of pissing anyone off about the book

“I do have regrets about the final chapter. I called out an old co-worker. I wrote it after I found out she had been talking shit. But writing the book felt like a diary entry. It wasn’t weird at all until I got the manuscript and then I realized, ‘oh shit, other people are going to read it.’ I gave it to my sister, who told me to give it to my dad. I let him read it. I told him, ‘All your business is out there; I’d be happy to address it.’ I didn't hear from him for three days, and then he was like, ‘We need to talk.’ We had a phone conversation and he was like, ‘Whatever you decide is good.’ It forced us to have a conversation about the divorce.

On her failed ABC pilot, I Hate LA Dudes with Shonda Rhimes

“It was my first experience working with a network and the studios and I wanted to include all of the studio’s notes and criticism and ultimately it was no longer my vision. It showed and they passed on it.”

On being “halfrican”

“My father is Senegalese, my mom is from Louisiana. When we would visit our cousins in Senegal, everything pop culture–wise comes six months to a year later over there. Because I was from L.A., they would ask me if we lived next door to movie stars. And they would all watch Baywatch. We would sit in a circle and watch Pamela Anderson. And then African Americans here would always say, ‘Oh you're African? Do you have a lion?’ ”