Nicaila - Side Hustle Pro | Makers Series

Over the past few weeks, you’ve learned more about the creative processes behind soap making, upholstering, and candle making! While today’s featured maker doesn’t create a physical product, what she does create has impacted many fellow creative entrepreneurs-

I would like to introduce you to Nicaila Matthews Okome of the Side Hustle Pro podcast!

A few years ago I came across the Side Hustle Pro podcast and I loved it! I really enjoyed hearing the stories of other Black women entrepreneurs- how they started, what hurdles they encountered along the way, and how they became successful. So of course I wanted to know more about the woman behind the podcast!

This window into their process wouldn’t have been possible without the foresight of Nicaila and her process. I was interested in learning more about her and what motivated her side hustle! There is something for everyone in her insightful answers and I’m so glad we could make time to put this together for you!


How did the shift from digital marketing to full-time podcasting take place? 

It started very gradually, with me tipping my toe into the waters of entrepreneurship. The first six months after I launched my podcast, I focused solely on consistency (releasing an episode each and every Wednesday and promoting that episode across all of my social media platforms). I leaned on my digital marketing background to build the Side Hustle Pro brand across social media and connect to my listeners outside of the podcast. I started to test out monetization and explore turning my podcast into a business at the six-month mark. That meant forming an LLC, opening a business bank account, launching my first paid product. Then, I started to put my plan together. The first step was SAVING to cover my living expenses for several months. Then I spent the next year working that plan: learning, growing, refining my revenue streams and deciding on a realistic date to go full-time. I set a quit date of September 2017. I had to push it back a bit, but in December 2017 I made the shift to full-time podcasting.

What ignited your passion for black women entrepreneurs? 

I can't think of a particular moment that ignited that passion. I am that girl following random people on Instagram just because I think you're fly and liking all your photos. I have always been drawn to badass black women who are not afraid to walk in their purpose. So talking to black women entrepreneurs who were able to start out as side hustlers and then grow their hustle into their own business inspired me during a time when I felt rejected and lost. Talking to them reminded me that there is unlimited magic inside of me, and I don't have to wait on anyone else to give me permission to unleash that. 

Walk us through your creative process. What does it look like from idea to finished podcast episode? 

Well, it starts with moments where I'm just able to sit in a coffee shop and do one of my favorite activities (stalk dope black women on the internet, LOL). I sit down and scroll through my episode management sheet, taking a broader look at the upcoming episodes and themes. I look for gaps or redundancy and keep note of what I think is missing (as far as industries I haven't covered or perspectives/lessons I want the show to teach). Then I move on to researching Black women entrepreneurs, scouring the latest news stories, the top business and entrepreneurship websites, etc. I have an endless list of names that I'm "researching." Once someone moves from "researching" to the desired guest, my assistant reaches out and we begin the booking and reminder process. When it's episode day, I clear my calendar. I want to devote all my time to get into the right mental zone to be completely engrossed in my guest's stories. I've learned from experience that when I have too much on my to-do list my mind is scattered and it's not fair to the guest, nor is the conversation as fruitful as it can be. Once we're done recording, I send all files to my producer and he handles the editing and mixing. Once it's ready, I schedule and on release day it's time to promo! Most importantly, I batch these processes. So I only record on Mondays and Tuesdays (because of the mental focus it requires of me and since I actually need to do other things the rest of the week—like coach my Podcast Moguls students!).

What is the most fulfilling aspect of running Side Hustle Pro? 

The most fulfilling aspect is knowing the show is having such a positive impact on so many people's lives. Knowing that people are starting side hustles, upgrading their businesses, learning new strategies and resources, and learning about black women entrepreneurs they may not have heard of, means everything to me. Just today, a listener came up to me in the street to tell me how much she loves the show and how she started her side hustle shortly after she discovered the podcast. How amazing is that?!


As an entrepreneur, sometimes motivation can ebb and flow. What slows you down and how do you overcome it? 

What slows me down is when my energy is off. Energy is real and I do everything in my power to protect it. To overcome it, first I really took inventory of my working style this year (and I no longer compare it to anyone else's). Then, I started doing these 90-day sprints (I call it my Goal Getter Action Plan) and it helps me to set ridiculously small goals so I get things done and push past feelings of overwhelm and mental blocks. I know I need off days to let my creative juices flow. So I remind myself that if I knock out all my action items by a certain day, I get to take Friday and Saturday off. All of this has been extremely helpful in keeping me moving forward.

What's been your favorite entrepreneurial highlight so far? 

My favorite entrepreneur highlight was in summer 2018 when I was able to take an impromptu trip to join my sister and her husband, kids, and our parents at Disney World. When they were booking their tickets, I wasn't sure what my schedule would be like at the time so I thought I would have to pass on the trip. But then a week before I realized I had nothing pressing and could clear my schedule and book a last minute ticket and join them. Getting to spend those priceless moments with the fam was everything to me. Entrepreneurship allowed me that flexibility and freedom to get up and go and for that, I am forever grateful.

What's the most important thing you've learned so far about yourself as a maker?

That I can do it! I can do this crazy thing called entrepreneurship! I've learned that I can trust myself to find my way no matter what occurs. I've had so many moments in the past where I was lost and confused, and I look back at it all like, that had to happen for me to be here today. So why wouldn't I trust that things will continue to work out? Through all the ebbs and flows, every mistake is here to teach me something. So I can breathe, and focus on living and enjoying this life, rather than waiting for some ultimate moment of success to exhale. Most importantly, I know God's got my back.

Dopeness all around. Let me know what you thought of Nicaila’s feature! It was a pleasure getting to know more about her and the process behind bringing this amazing podcast to life.

Keep up with Nicaila online: Listen to SIde Hustle Pro on Apple Podcast or Stitcher. Visit her websites:, and give her a follow on instagram, facebook, and twitter- she’s @sidehustlepro everywhere. Also check out the coloring app she created with her husband- Color Noir!

Miss the first 3 makers features? Check them out here!

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Stay tuned for the next Makers Monday feature on July 1!