Issa Rae Talks AI in Hollywood, the Business of Storytelling, & More at Invest Fest

Acclaimed creator, producer, and entrepreneur Issa Rae opened up about her business ventures, journey, and creative process during a live fireside chat moderated by award-winning journalist Selena Hill at Invest Fest 2025.

In this candid conversation, Issa shared unfiltered insights about staying authentic in the spotlight, using influence to open doors for others, and defining success on her own terms.

She also talked about the evolution of storytelling and the impact that AI is having in Hollywood.

00:00 Introduction

01:14 Issa talks about balancing being a creator and a boss

05:15 The challenges of being in business

11:45 Telling diverse stories without compromising integrity

16:20 The cancellation of "Rap Sh*t"

19:29 The business of storytelling

22:12 The disruption of AI in Hollywood

27:50 Issa talks new book, "I Should Be Smarter By Now"

34:46 Issa's business advice to creators