Practice Memorable Brand Storytelling With Nicaila Matthews Okome
Nicaila Matthews Okome is an entrepreneur, digital marketing expert, and creator and host of “Side Hustle Pro,” an award-winning podcast that elevates successful Black women entrepreneurs. Featured on platforms like Today, TED, CNBC, and more, she uses her voice to strategically empower underrepresented stories and make them known all across the world.
1. How has your personal journey influenced your efforts to empower and equip underrepresented entrepreneurs?
My journey from corporate roles at companies like Google, NPR, and MTV Networks to creating Side Hustle Pro has deeply shaped my mission to empower underrepresented entrepreneurs. Growing up in Jamaica and later in the Bronx, I saw firsthand the resilience and creativity it takes to succeed when opportunities aren’t handed to you.
That upbringing instilled a sense of possibility and determination that I channel into my work. When I transitioned from my side hustle to running my business full-time, I realized how important it was to see examples of people who looked like me succeeding. That’s why Side Hustle Pro exists—to spotlight bold, Black women entrepreneurs and provide the inspiration and tools needed to thrive in spaces where we’ve historically been underrepresented.
2. How does your podcast, Side Hustle Pro, serve as a storytelling tool that builds professionals’ career resilience?
Side Hustle Pro is a platform that celebrates real, relatable journeys. By sharing the stories of entrepreneurs who have successfully transitioned from side hustles to thriving businesses, the podcast highlights the perseverance, pivots, and persistence behind success. Each episode is a testament to the fact that obstacles don’t define you—your response to them does. This storytelling not only inspires listeners but also equips them with actionable insights to overcome their own challenges. It reinforces the idea that setbacks are stepping stones and resilience is a skill that can be cultivated.
3. How can entrepreneurs craft unique brand stories that help them stand out in today’s competitive market?
Your unique brand story starts with your “why.” Why are you doing this work, and how does your personal experience connect to the problem you’re solving? People connect with real, human stories—not just polished marketing speak. Share the moments that sparked your business idea and the values that drive you. Don’t be afraid to let people see the passion behind your work. It’s the connection to your audience, the way your story makes them feel seen, that helps you stand out. When you let your journey shine through, you’re not just building a brand—you’re building trust and community.
4. What advice do you have for professionals struggling to craft authentic brand stories that resonate with their audience?
Start by letting go of the idea that your story has to be perfect. It doesn’t. In fact, the real magic happens when you embrace the imperfections and share the journey as it really is. Think about the challenges you’ve faced—those “aha!” moments or even the missteps that taught you something valuable. Share them. People don’t connect to perfection; they connect to honesty and relatability. Also, don’t forget to listen to your audience. What are they struggling with? When you weave their struggles into your story, you’re showing them that you’re not just selling—you’re serving. And above all, take action. Don’t wait until it feels perfect—just start sharing and refine as you go.
5. Why is it crucial to cultivate a reliable brand image for those looking to grow their side hustle?
Your brand image is the first thing people notice—and for side hustlers especially, it has to communicate, “You can trust me” right from the start. When you’re consistent in how you show up—whether it’s through your social media, your customer service, or your product quality—you’re building credibility. And credibility is what gets people to choose you, even if you’re just starting out or don’t have a big budget. At the end of the day, people invest in people they trust. So your job is to show up authentically, consistently, and with a clear message that tells them, “I’m here to help, and I’ve got what you need.”
