Written by Lisa D. Tinsley
At this year’s InvestFest, award-winning actress, writer, and entrepreneur Issa Rae shared her evolution from a creative storyteller to a powerful business leader. Best known for Insecure, Rae now oversees ventures across television, film, music, hospitality, and lifestyle.
Rae revealed that she did not initially see herself as a businesswoman. “I thought the business side was the worst part,” she admitted. Building companies and partnerships soon became a way to expand opportunities for others. Today, her portfolio includes a music label, a management company, coffee shops, restaurants, and a wine brand.
Partnerships, Rae emphasized, have been central to her success. “I don’t pretend to know more than I do,” she said. “I know what I bring to the table, and I know where I need to listen.” She cautioned, however, that choosing partners requires intention — friendships don’t always translate into successful business relationships.
Rae also discussed the importance of taking risks and learning from mistakes. Early in her career, she invested her own money in projects before she was ready. “Even the failures taught me what to do better next time,” she said.
Looking at Hollywood, Rae voiced concerns about the dominance of sequels and reboots and the growing role of artificial intelligence in entertainment. She warned that without regulation, AI poses risks to creators’ ownership and intellectual property.
Still, Rae remains focused on opportunities ahead, particularly in Africa and the Caribbean, where she sees potential for global storytelling and infrastructure development.
Her final message to InvestFest attendees was simple: “Your future co-founder, your future collaborator, even your future investor could be sitting right next to you. Partnerships have been everything for me.”