Nicaila Matthews, the side hustle pro.
It takes a certain kind of person to risk it all and follow their startup dreams.
A person with a serious safety net, and access to traditional forms of funding, for one.
But dedicating your free time outside your day job is a more accessible way to launch the idea that could eventually become a full-fledged career. That’s why Nicaila Matthews created Side Hustle Pro, a podcast that features black women entrepreneurs explaining how they turned their side hustles into successful businesses.
"When I was thinking about going out on my own, I didn’t see myself reflected in the narrative of entrepreneurship," Matthews said.
She means both representation of black women founders, and representation of people who took the responsible, part-time route to their dreams.
"The reason I didn’t see myself as an entrepreneur is because the narrative of entrepreneurship was of white men," Matthews said on a recent episode celebrating the one-year anniversary of her podcast. "I wanted to gain confidence and motivation from women who look like me. And particularly women who started as side hustlers (because, let’s face it, these student loans are not going to pay themselves)."
Side Hustle Pro—described in each episode as the podcast that teaches you to build and grow a side hustle from passion project to profitable business—features women in media, tech, beauty, and fashion. A year in, Matthews has interviewed Blavity CEO Morgan DeBaun, plus-size designer Monif C., Carol’s Daughter founder Lisa Price, and plenty of other guests. The entrepreneurs who call into the podcast span industries, but they have in common their experiences as founders.
Many of the guests on the show were the first black women to do something in their field, Matthews said.
One year after its launch, Side Hustle Pro gets 400,000 downloads and 65,000 unique listens per month.
Matthews, 33, launched her own side hustle when she graduated with an MBA but no job in 2015. The University of Pennsylvania and University of Michigan Ross School of Business alumna had interned in ad sales at Google, but didn’t secure a full-time offer.
While facing unemployment, she got started on her own idea: a blog, and then podcast, that would have the kinds of entrepreneurship discussions she wanted to hear but couldn’t find in Inc. or Fast Company.
Things didn’t stay down for too long. Now, Matthews works as a senior manager of social marketing for NPR. She knows podcasts from her day job, and it shows in her own side hustle.
The guests on her podcast give advice about raising money from white male investors in Silicon Valley, where only a handful of black women have raised over $1 million. They impart startup wisdom like, "if you can’t make it as a side hustle, you can’t make it as a business," and that you’re the only one who truly understands your own vision. They give purely practical advice too, like how to know when to make the jump from side hustle to full-time business.
"I don’t think that you’re ever going to feel that it’s the right time," curlBOX founder Myleik Teele advised listeners when she appeared on the podcast. "You’re going to feel guilty. There’s not a person who has taken the leap who hasn’t felt guilty."
The podcast’s focus on both black women entrepreneurs and side hustling is connected.
"It’s common for black women or black entrepreneurs to ensure they’re financially grounded in some respects before they go out on their own," Matthews said. "People who risk it, quit their jobs, go out and live in Silicon Valley—that’s not attainable for everyone. Someone who had their job, that’s more attainable."
Side Hustle Pro is special for more than just its topic. A lot of entrepreneurship media out there is, frankly, pretty boring. Matthews’ podcast is fun, accessible, and inspirational for anyone who’s considering starting their own business. Her charisma invites successful entrepreneurs to give their best advice and can easily keep listeners hooked even in an episode where she’s riding solo, reflecting on her own journey.
In every interview, you can tell that Matthews is a fan of her guest. Teele, who said she quit curlBOX three times before she launched it in earnest, has been one of Matthews’ favorite interviews. Her dream guest is, of course, Oprah.
For now, Side Hustle Pro is Matthews’ own side hustle. But like it happened for all her guests, the transition is coming.
"Someone asked me where i see myself in five years: I for sure will be a full-time entrepreneur," Matthews said on a recent episode. "Mark my words."