Career Side Hustle Expert Nicaila Matthews Okome on Joining the Gig Economy

Digital marketer by day, podcaster by night, Nicaila Matthews Okome shares how she turned her side hustle into a full-blown career.

By Brienne Walsh Photographs by Grace Rivera
PUBLISHED 01/20/2023 | 5

Want to hear a story? Perhaps one about Janice Bryant Howroyd, the first Black woman to run a $1 billion business. Or maybe one about Krystle Rowry, the web designer and brand strategist who works with New York Times bestselling authors and Grammy Award-winning artists. And let’s not forget KJ Miller, who grew her cosmetics side hustle Mented into a multimillion-dollar brand, or Tiffany “the Budgetnista” Aliche, who went from unemployed and unable to afford her mortgage to renowned finance expert.

These are just some of the entrepreneurial women who wanted more than a typical 9-to-5 job—and they hustled to get it. 

Nicaila Matthews Okome, host of the Side Hustle Pro podcast, is collecting their stories andturning her own passion project into a full-time career in the process.

When Okome graduated with an MBA from the University of Michigan’s Ross School of Business in 2015, she was ashamed because she didn’t have a job. “I interviewed for everything and anything under the sun,” says Okome, who was born in Jamaica and raised in the Bronx, N.Y..

When she wasn’t submitting résumés, Okome worked on her blog. She wanted to show potential employers that she had marketing skills and figured she could do that by writing quality content. She also began interviewing friends and former colleagues for her column, specifically Black female entrepreneurs.

“I was around a lot of entrepreneurial minds at the Ross School,” she says. “That kind of thinking always appealed to me, even though I didn’t think I could personally handle an entrepreneurial lifestyle.”

Later that year, Okome landed a full-time job as the senior manager of digital marketing at NPR in Washington, D.C., but continued her blog on the side—a sort of side hustle, if you will. But she soon realized, through her conversations with successful women, that her belief that being an entrepreneur meant sacrificing comfort and financial stability (“I like my manicures and pedicures, okay?” she says, laughing) was false. 

So, about a year later, Okome took those interviews and launched her own podcast, Side Hustle Pro.

“Many of the people I spoke to started their businesses as side hustles while still working full-time jobs,” she says. Black women in particular are leading the charge, with an estimated 17% of Black women in the United States currently in the process of starting or running a business, compared with 10% of white women and 15% of white men.

Okome made a wager that people would be interested in hearing about those side hustles and how they transformed into thriving businesses. And she was right. The podcast, which Okome produced with no prior technical experience and marketed herself, was so successful that she was able to quit her NPR job in 2017.

“I wanted to talk about how Black women get the money they need, juggle full-time jobs and don’t get fired,” she says.

To date, the podcast has been downloaded more than seven million times and has been featured in Forbes, Fast Company and Mashable, among other publications. And the guests on the show? Inspiring entrepreneurs—like Myleik Teele of CurlBox, Lisa Price of Carol’s Daughter, Maya Elious of Built to Impact and income strategist Nicole Walters—make appearances every week and talk about everything from starting a hustle and getting funding to marketing yourself and managing multiple businesses.

Side Hustle Pro even offers several educational opportunities, including Podcast Moguls, an eight-week accelerator program that helps people create successful podcasts, and Master the Gram, which teaches business owners how to engage with a dedicated audience on Instagram.

Okome has also appeared on the Today Show and launched a YouTube channel, Nicaila TV. She hopes that her hard work and passion will eventually translate into a thriving lifestyle brand and, perhaps, even her own television show.

“People are always like, ‘Why are you working on that little podcast? Why are you working on that YouTube channel?’” Okome says. “They don’t realize that consistent work on little things yields big results.”

Millie content is licensed from Dotdash Meredith, publisher of Millie, Real Simple, InStyle, Investopedia, The Balance and more.

Brienne Walsh is a writer based in Savannah, Ga. She contributes to Forbes, Rangefinder and MarketWatch, among other publications.


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