Alright – so today we’ve got the honor of introducing you to Gabrielle Jackson. We think you’ll enjoy our conversation, we’ve shared it below.

Gabrielle, appreciate you joining us today. Learning the craft is often a unique journey from every creative – we’d love to hear about your journey and if knowing what you know now, you would have done anything differently to speed up the learning process.

How did you learn to do what you do?

I learned what I do through a combination of hands-on experience, relationship-building, figuring things out in real time, and guidance from my mentors. My career in entertainment started as a social media intern, and from there, I moved into talent hospitality and event production roles for Broccoli City. That experience gave me a deep understanding of how live events come together, and I quickly realized that being on the ground and doing the work was one of the best ways to learn.

Over time, I expanded my skill set through roles at Live Nation in media and sponsorship, which gave me a deeper understanding of the business and partnership side of entertainment. Currently, I work at Eighty Five South Media in Booking and Partnerships while also managing talent under Family Business Management. In addition, I manage R&B/neo-soul artist Helen Hailu, so much of what I know comes from working across multiple lanes—comedy, music, and live events—and applying knowledge from where these avenues intersect to create innovative solutions.

Knowing what you know now, what could you have done to speed up your learning process?

Looking back, I would have leaned more into asking for mentorship and support early on. As a first-generation college graduate, I had to navigate a lot on my own and sometimes felt like I had to “figure it out” without asking too many questions. But the truth is, people are often willing to share knowledge if you seek them out. I also would have invested more time in understanding the business side—contracts, negotiations, budgeting—sooner, since those are skills that become critical as you grow in this field.

What skills do you think were most essential?

Relationship-building and communication are at the core of everything I do—whether it’s booking talent, producing events, or managing talent, being able to connect with people and communicate clearly is essential. Organization and project management are also huge, especially when juggling multiple clients, events, and partnerships.

Adaptability has been key because every event, show, or partnership comes with its own set of surprises. From stage managing at Broccoli City Festival to managing comedy tours and music releases, you have to think fast and solve problems on the fly. Also, understanding both the creative and business sides of entertainment has allowed me to be a better advocate for the talent I work with, especially Black creatives.

What obstacles stood in the way of learning more?

As a young Black woman in the entertainment industry, I’ve had to work hard to be taken seriously and to earn trust in spaces where I may be one of few. Being a first-generation college graduate, I haven’t always had a clear blueprint to follow. I’m grateful to have had mentors like Brandon McEachern and Chad Oubre, who’ve poured into me and shared invaluable knowledge, but I’ve still struggled at times with the fear of failure. What they’ve taught me, though, is that some of the most important lessons only come through experience — and sometimes, that means failing.

Financial limitations have also played a role in my career, as many opportunities in entertainment require working long hours for low pay at the entry level, which can make it difficult to grow without additional resources. These obstacles have made me more resourceful and motivated to leverage my environment to work for me.

Gabrielle, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

I’m an entertainment professional with a focus on event production, talent management/booking, and partnerships. As a first-generation college graduate, I earned my marketing degree from Howard University, where I became a proud member of Alpha Chapter, Delta Sigma Theta Sorority, Incorporated. I got my start as a social media intern before moving into talent hospitality and event production at Broccoli City, later expanding my experience in media and sponsorship at Live Nation before transitioning into comedy. Currently, I manage comedians under Family Business Management, independently manage R&B/neo-soul artist Helen Hailu, and lead booking, partnerships, and project management initiatives at Eighty Five South Media, all while staying committed to creating opportunities for Black creatives through entertainment, business, and storytelling. I’m most proud of the opportunities and connections I’ve been able to create—both horizontally and vertically—that uplift and support our community. I believe it’s essential to pay it forward and build with one another as we work toward our dreams and aspirations. ‘Community over competition’ is a value that I’ve been taught by visionaries in this industry, and it’s something I’m committed to practicing intentionally in everything I do.

What do you find most rewarding about being a creative?

For me, the most rewarding aspect of being a creative is seeing the impact of what’s produced — the conversations it sparks and the lives it can change. What’s even more powerful is that those changes extend beyond the artist; they can influence entire communities in meaningful and positive ways. Knowing that something I’ve helped bring to life can inspire, uplift, or open doors for others is what makes it all worth it.

Have any books or other resources had a big impact on you?

A few books that I’ve learned a lot from are Big Magic By Elizabeth Gilbert, All You Need To Know About The Music Business by Donald Possman, and The Alchemist by Paul Coelho.

Contact Info:

• Instagram: https://www.instagram.com/sheeshgabby/
• Linkedin: https://www.linkedin.com/in/gabrielle-jackson-17106916b/
• Other: https://linktr.ee/TheHelenHailu

Image Credits

Jon Logan
Drew Alexander