Home Podcasts Side Hustle Pro
Side Hustle Pro

Side Hustle Pro

Nicaila Matthews Okome | Side Hustle Pro Media 524 Episodes Aug 21, 2026

Side Hustle Pro spotlights bold black women entrepreneurs who have scaled from side hustle to profitable business. Join Chief Side Hustler turned full-time entrepreneur Nicaila Matthews Okome for your weekly installment of Side Hustle Pro and learn actionable strategies to start small and get going–wherever and whoever you are. The podcast features interviews with inspiring Black women entrepreneurs who started out as side hustlers, including Myleik Teele, Morgan DeBaun, Tiffany "The Budgetnista" Aliche, and more.

Episodes

How Karen Young Built OUI the People
How Karen Young Built OUI the People Aug 21, 2026 1:14:01 In this episode, I sat down with Karen Young, founder of OUI the People, a fine fragrance and body care brand born out of her own struggle with razor burn and ingrown hairs. Karen walks us through her path from fashion, where she interned at Dolce and Gabbana, to becoming an executive at Estee Lauder, to eventually building a beauty brand now sold in Sephora.But Karen's story starts before OUI the
She Left Corporate Law, Went Back to Work, and Still Built a Global Fashion Brand
She Left Corporate Law, Went Back to Work, and Still Built a Global Fashion Brand Aug 14, 2026 1:11:27 In this episode, I sat down with Busayo Olupona, founder and creative director of Busayo, the Brooklyn- and Lagos-based fashion brand known for its bold prints and textiles created with artisans in Nigeria. Busayo shares how she went from corporate finance law to bringing handmade pieces home in suitcases, selling them at scrappy pop-ups, and eventually landing in major retailers including Saks Fi
How Her Wine Became the Obama Presidential Center’s Official White Wine
How Her Wine Became the Obama Presidential Center’s Official White Wine Aug 7, 2026 51:33 After a devastating flood forced Chrishon Lampley to close her Chicago art gallery and wine bar, she turned that loss into the foundation for Love Cork Screw, a nationally distributed wine brand that has sold more than two million bottles.In this episode, Chrishon shares how she broke into the wine industry with no upfront capital, got her products into major retailers, and navigated the realities
7 Things I Had to Unlearn Before Leaving My Corporate Job
7 Things I Had to Unlearn Before Leaving My Corporate Job Jul 31, 2026 43:40 If this resonated with you, here are additional resources:⭐ APPLY TO SHIFT: https://sidehustlepro.co/shiftIn this episode, I'm sharing the seven beliefs I had to unlearn before I could finally leave my corporate job and build Side Hustle Pro full time. I spent decades in corporate America, working at places like HBO, MTV, Google, and NPR, and even though I knew I wanted to leave, I wasn't mentally
Why She Pulled Her Brand Out of Whole Foods After 26 Years | Dawn Fitch, Founder of Pooka Pure and Simple
Why She Pulled Her Brand Out of Whole Foods After 26 Years | Dawn Fitch, Founder of Pooka Pure and Simple Jul 30, 2026 52:12 If this resonated with you, here are additional resources:⭐ APPLY TO SHIFT: https://sidehustlepro.co/shiftIn this episode, I sat down with Dawn Fitch, founder of Pooka Pure and Simple, to talk about the winding road that took her from designing album covers in the music industry to building a natural beauty brand rooted in her own health journey. Dawn opens up about the years it took to get an MS
How Roxy Couse Replaced Her Corporate Title With Her Personal Brand
How Roxy Couse Replaced Her Corporate Title With Her Personal Brand Jul 24, 2026 49:42 If this resonated with you, here are additional resources:⭐ APPLY TO SHIFT: https://sidehustlepro.co/shiftIn this episode, I sat down with Roxy Couse, the creator behind Millennial Manager, to talk about how she built a thriving personal brand while climbing the corporate ladder. Roxy spent almost 15 years in corporate, working her way up to senior director, before stepping away to run her content
She Emptied Her Retirement to Open a Tea Brand (Jamila Wright, Founder of Brookyn Tea)
She Emptied Her Retirement to Open a Tea Brand (Jamila Wright, Founder of Brookyn Tea) Jul 17, 2026 1:00:11 If this resonated with you, here are additional resources: APPLY TO SHIFT: https://sidehustlepro.co/shiftIn this episode, I sat down with Jamila Wright, co-founder of Brooklyn Tea, to trace the full story of how she and her husband Ali turned tea dates into a business. Jamila walked me through leaving a career in education, emptying her retirement savings, and fighting a two year trademark ba
How Real Housewives of Atlanta's Cynthia Bailey and Co-Founder Dana Hill-Robinson Built Glowissima Skincare
How Real Housewives of Atlanta's Cynthia Bailey and Co-Founder Dana Hill-Robinson Built Glowissima Skincare Jul 14, 2026 1:02:15 If this resonated with you, here are additional resources:⭐ APPLY TO SHIFT: https://sidehustlepro.co/shiftIn this episode, I sat down with longtime friends and business partners Cynthia Bailey and Dana Hill-Robinson to talk about how a friendship that started in a New York hair salon in the 1990s turned into a skincare brand thirty years later. Cynthia shares her path from an eighteen year old mod
520: How Jotaka Eaddy Built a Movement of 44,000 Black Women Overnight
520: How Jotaka Eaddy Built a Movement of 44,000 Black Women Overnight Jul 7, 2026 1:03:42 If this resonated with you, here are additional resources:⭐ APPLY TO SHIFT: https://sidehustlepro.co/shiftIn this episode, I sat down with Jotaka Eaddy, founder of Full Circle Strategies and Win With Black Women, for a conversation about power, purpose and resilience. We talked about her childhood in Johnsonville, South Carolina, a town of under 1,400 people that taught her the value of community
519: After 10 Million Downloads, Here’s What I Learned
519: After 10 Million Downloads, Here’s What I Learned Jun 20, 2026 25:47 If this resonated with you, here are additional resources: ⭐ APPLY TO SHIFT: https://sidehustlepro.co/shiftWhen I launched Side Hustle Pro, I thought success would be measured by downloads, rankings, sponsorships, and audience growth. And while reaching 10 million downloads is a milestone I'm incredibly grateful for, I've learned that the true value of podcasting has very little to do with the num
518: The ONE skill you need to learn before you QUIT
518: The ONE skill you need to learn before you QUIT Jun 12, 2026 30:12 If this resonated with you, here are additional resources: ⭐ APPLY TO SHIFT: https://sidehustlepro.co/shiftIn this solo episode, I am getting real with you about the one skill that changed everything for me and that I believe every woman needs to develop right now: learning how to make money directly for yourself. I am sharing why the leap from employee to entrepreneur is so hard, how our entire l
517: After Quitting My 6-Figure Job to Launch My Own Business Here’s What I Learned
517: After Quitting My 6-Figure Job to Launch My Own Business Here’s What I Learned Jun 5, 2026 26:05 If this resonated with you, here are additional resources: ⭐ APPLY TO SHIFT: https://sidehustlepro.co/shiftIn this solo episode, I'm pulling back the curtain on my entrepreneurial journey and sharing the six most important lessons I've learned since leaving my corporate job in 2017. Most people assume that quitting was my biggest risk, but the truth is, the scariest steps happened long before I ev

Recommended