Issa Rae in conversation with Jack Conte

We gathered some of the biggest names in film, podcasting, art, activism, music, and media for Patreon Assembly, an afternoon of storytelling and performances. Through personal stories from their own creative journey, our guests shared how they leveraged entrepreneurial spirit, artistic control and their relationship with their audience to build successful, durable creative careers.

Our very own Jack Conte got to chat with Issa Rae, the creator, writer, and star of HBO’s Insecure and the award-winning web series Awkward Black Girl. Issa is also the founder of two production companies, Issa Rae Productions and ColorCreative, and has over 1,000 patrons on Patreon.

As somebody who works both in front of and behind the camera, Issa Rae wears a lot of different hats. Here’s what we learned about her approach to running a creative business, managing people, and the lessons she’s learned along the way.

How she created her first web series:“I just got my friends together, rented a camera from the library and uploaded it,” says Issa at the 2:30 mark. “It didn’t go viral but it started spreading to other college campuses that were having the same experience and it was an epiphanous moment for me.”

Her approach to creating her own content:At 10:17, Issa says, “I do draw from real-world experiences. It’s the old phrase, ‘write what you know,’ but I take that very seriously in terms of the content I create and the content I want to see. I try to make content that I know my friends would wanna watch, that I would wanna watch.”

Her approach to producing other creators’ content:“I gravitate towards content that people specifically are very passionate about because that says a lot too,” Issa says at the 10:40 mark. “For me, it’s just more interesting when it feels personal.”

How she manages her time:At the 7:15 mark, Issa says: “I’m someone that works with a structure and with a routine, so if I know my day from 10 to 5 or 10 to 6 is going to be in the writer’s room, I can plan to be up at 4 or 5 to get the things I need to get done before then and then I go to bed mad early and I feel refreshed.”

How she works with and manages her team:“Listening and shutting the f*ck up has proven to be so valuable in collaborating with others,” says Issa at 25:38. At 26:18, she adds, “I love working with people who are good at what they do and respecting that and then inserting myself when I feel like it’s necessary.”

And last but not least, the hardest lesson she’s had to learn so far:“It’s so simple, but it’s not all about me at the end of the day,” says Issa at the 20:20 mark. “And when you’re focused on your own work and people are helping you with your work, you can forget that. You gotta make sure that everybody is growing with you.”