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Interview with Nicaila Matthews Okome of Side Hustle Pro

Jul 29, 2021
(updated: Dec 1, 2022)
Max 5 min read

Today we’re speaking with recent Indy partner Nicaila Matthews Okome, the host of the Side Hustle Pro podcast, a top business podcast that spotlights bold, Black women entrepreneurs who’ve scaled their businesses from side hustle to full time entrepreneurs. She is also the founder of Side Hustle Pro, LLC, a podcasting and marketing agency that shines a light on untold narratives. 

An alumna of the University of Pennsylvania (BA) and the University of Michigan (MBA), her work is geared at helping emerging podcasters to create and launch their own podcasts, grow their influence through targeted social media marketing and build a profitable business. Nacaila stays busy as a new mother When not working to expand her multifaceted platform that continues to reach and help other women with their side hustle success, Nacaila stays busy with her new main hustle as a new mom.

W2: Please tell us about yourself

NMO: My name is Nicaila Matthews Okome and I’m a Jamaican born, Bronx bred marketer and side hustler turned full-time podcaster, entrepreneur, mother, and an overall multifaceted person. My professional experience spans digital marketing, ad sales and social media strategy for NPR, Google, MTV Networks and more.

In 2016, I created the Side Hustle Pro podcast. Since launching Side Hustle Pro, my podcast was named “the perfect entrepreneurship podcast” by Mashable, featured on the TODAY show, earned more than five million downloads, and amassed a loyal social media following of aspiring entrepreneurs. 

W2:How do you describe yourself when talking about your business?

NMO: I describe myself as a podcaster, marketer, and online entrepreneur and I am passionate about helping other multi-passionate side hustlers find their voice and share their message with the world. Now, more than ever, people are increasingly interested in being their own boss and I use my platform to help other Black women follow their dreams.

W2: What is it that you do? What’s your business?

NMO: I’m first and foremost a storyteller. On the Side Hustle Pro podcast, I highlight the journeys of Black women side hustlers and entrepreneurs as they navigate the challenges, confusion, and uncertainty of starting their own business.

In addition, as part of my Side Hustle Pro platform, I created the Podcast Moguls accelerator program, in which I work intensively with emerging podcasters to create and launch their hit podcasts, grow their influence through targeted social media marketing, and build a profitable business from podcasting.

W2: Why the name “Side Hustle?” Can you share more about that?

NMO: When I was wrestling with the idea of starting some kind of business, I knew I wanted to do this while also having a full time job. I was not interested in just diving head first into an unproven concept and then being stressed with no income. So I knew I would have to start it on the “side” while I worked. Alas, the name side hustle pro was perfect.

W2:How long have you been indie/side hustling?

NMO: I’ve side hustled ever since my days working at Viacom when I tried to get an indie PR agency off the ground. Side Hustle Pro itself is five years old. Every five years or so I feel a shift and wonder where I’ll be next. I’m an ambitious and multi passionate creative!

W2: What was one of the biggest challenges you faced?

NMO: By far being an entrepreneur and having a new baby during a pandemic. We were in no way prepared for the pandemic and it’s been a challenge learning to navigate working from home and childcare, especially when I have meetings, podcasts or live coaching calls with my Podcast Moguls accelerator students. Also being self-employed, I’m still learning what to pass along, especially now with my baby. I’m still learning to let go of a lot of things. 

W2: Why do you love doing what you do?

NMO: I just love connecting with so many awesome women who are starting amazing businesses and changing the lives of others! I love hearing from listeners about the impact the show has had on their lives and how it inspired them to start their side hustle. I love being able to reach out to my guests after the interview to check in on their businesses, build community, and learn from the growth in their journey.

I also love the flexibility that being an independent business owner gives me—being able to set my own hours, being able to work from anywhere, the ability to have this time with my child. It’s such a blessing to choose how my day will unfold and I’m really grateful for that.

W2: What’s been your biggest achievement to date with your business and where do you hope to go/do next?

NMO: This year has really shifted how I think about achievements, but I am extremely proud of myself for being able to grow my podcast business from a side hustle to a full blown business that gave me the ability to leave my job. There are definitely challenges to entrepreneurship, but it’s been a rewarding and liberating experience for me.

W2:What advice would you give to your former self and/or someone starting out?

NMO: I generate income from multiple streams, including sponsorships and digital products, but I spent time saving my side-hustle earnings before I made the leap to full-time entrepreneur. I recommend stockpiling at least six months of living and business expenses in savings before leaving your job. When your side hustle starts to make as much or more monthly than your day job, start to think about what the future holds.

But really the first piece of advice is that you have to crawl before you can walk. It’s easy to look at others and envy what they have accomplished, but the reality is it takes time, dedication and discipline to get there. You have to go through the growing pains before you get to a more polished place and that's normal. Know that wherever you are in your process, it is natural and it is an experience that is supposed to happen before you get to the next level.

But then you just have to go for it and know you’re gonna kill it!

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