Issa Rae, the trailblazing creator, writer, and actress, captivated a sold-out Houston audience during her recent appearance. Known for her wit, authenticity, and groundbreaking storytelling, Rae offered attendees an intimate look into her journey from internet sensation to Hollywood powerhouse. The evening was filled with laughter, inspiration, and a glimpse into her unrelenting drive for creativity and excellence.

The Power of Betting on Yourself

During the event, Rae reflected on a pivotal moment early in her career with her web series, Awkward Black Girl. Around the third episode, a non-Black network executive approached her with suggestions that would have drastically changed the essence of her show. “He wanted to replace the characters with celebrities, including me,” Rae shared, shaking her head in disbelief. Instead of compromising her vision, Rae doubled down, funding two more seasons of the show on her own. This decision caught the attention of Pharrell Williams, who backed her series and set the stage for what would eventually lead to her directing the first comedy show for Shonda Rhimes, I Hate L.A. Dudes.

But Rae’s dreams extended far beyond her early web success. Her ultimate goal was to create for HBO, a network she described as her dream collaborator. When the opportunity arose, Rae outgrew Awkward Black Girl and conceptualized Insecure, a series that redefined representation and storytelling in television. Her ability to evolve while staying true to her authentic voice has cemented her place as one of the most influential creatives of her generation.

Balancing Work, Creativity, and Confidence

When asked about her creative process, Rae revealed that solo beach vacations are her go-to space for writing and brainstorming. These quiet moments help her disconnect and reconnect with her artistic vision.

Rae also spoke candidly about confidence. “I’ve never felt more confident than I do right now,” she said. Her confidence stems from executing on her promises to herself. “I find confidence in doing what I say I’m going to do.” She encouraged the audience to trust their instincts and to embrace the lessons learned from failure—a recurring theme in her favorite film, Groundhog Day, which she said resonates deeply with her as “a person who messes up all the time.”

Building Spaces for the Culture

In addition to her contributions to the entertainment world, Rae has made waves in the hospitality industry. Last year, she opened Summerville, a lounge designed to cater to her desire for a chill space where Black people can gather. The event was also sponsored by Viarae, Issa Rae’s prosecco brand, highlighting her entrepreneurial ventures in hospitality. She described it as a place for great drinks, good vibes, and, most importantly, seating—a must-have for those celebrating their 30s with style and comfort. The inspiration came from her frustration with the lack of lounges that catered to her taste. “The music was wack, so I decided to open my own spot,” Rae joked. This venture follows her earlier success with a coffee shop, both of which were made possible through her long-standing collaboration with her business manager.

Advice for Creators and Dreamers

One of the most striking moments of the evening was Rae’s reflection on lessons learned. “I’m more vocal about what I don’t know, what I need to know, and what I know I know,” she said. She shared that deferring to people who didn’t know what they were talking about was one of her biggest mistakes early on. “Now, we’re all embarrassed,” she quipped, earning laughs from the audience. Her advice to creators was clear: trust yourself, advocate for your vision, and surround yourself with people who truly understand your goals.

A Night to Remember

The evening with Issa Rae wasn’t just an event; it was a masterclass in resilience, authenticity, and vision. Adding to the excitement, Rae’s new film, One of Them Days, was released the same weekend, showcasing her continued creative output. As she continues to break barriers in Hollywood and beyond, Rae’s journey serves as a testament to the power of staying true to oneself while boldly pursuing dreams. Whether through her critically acclaimed series, her entrepreneurial ventures, or her words of wisdom, Rae’s impact is undeniable.

For those who couldn’t attend, check out our exclusive video recap and relive the magic of an unforgettable night.