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Side Hustle Pro

Side Hustle Pro

Nicaila Matthews Okome | Side Hustle Pro Media 524 Episodes Jul 24, 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 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
516: From Caregiver to CEO: How Camille Joy Turned Her Son’s Diagnosis Into a Movement
516: From Caregiver to CEO: How Camille Joy Turned Her Son’s Diagnosis Into a Movement May 29, 2026 1:00:33 In this episode, I sat down with Camille Joy, founder of the Moments of Joy Podcast and author of Moments of Joy: 90 Days of Encouragement, published by Penguin Random House. Camille is a trafficking survivor who escaped an abusive situation at 21, became a high school dropout turned executive chef, and fought her way into a six-figure salary by going directly to the CEO. When her youngest son Mas
515: From Corporate to Creative: How Jessica Lane Alexander and Lori Hall McKissic Built Pop’N Creative into a $4M Agency
515: From Corporate to Creative: How Jessica Lane Alexander and Lori Hall McKissic Built Pop’N Creative into a $4M Agency May 22, 2026 59:47 In this episode, I sat down with the powerhouse duo behind Pop’N Creative, Jessica Lane Alexander and Lori Hall McKissic. These two met years ago at Turner Broadcasting and spent years rising through the ranks of some of the biggest names in media and entertainment, including TBS, TNT, UPTV, and TV One, before finally betting on themselves. Their story is one of calculated risk, deep friendship, a
514: From Tutoring Classmates in High School to $1M College Prep CEO w/ Janae Young
514: From Tutoring Classmates in High School to $1M College Prep CEO w/ Janae Young May 15, 2026 1:16:23 In this episode, I sat down with Janae Young, founder and CEO of Young College Prep, who started her first business at just 15 years old, tutoring classmates out of her school library in Wilmington, North Carolina. By the time she graduated high school, she had a team of eight tutors. By the time she graduated from Stanford, she had hit $300K in annual revenue. And by 2025, she crossed her first m
513:  Tiffany Aliche on What the Hard Years Teach You About Money and Resilience
513: Tiffany Aliche on What the Hard Years Teach You About Money and Resilience May 8, 2026 1:06:49 This week in the guest chair is Tiffany Aliche, known to millions as the Budgetnista and the author of the New York Times bestseller Get Good With Money. Tiffany is back for a deeply personal conversation about what burnout actually looks like when you’re at the top of your game, and what it finally took for her to listen to herself.She opens up about the physical and emotional signs she ignored f
512: How Leah Collins Turned Financial Mistakes Into a TV Show, Multiple Income Streams, and a Purpose-Driven Career
512: How Leah Collins Turned Financial Mistakes Into a TV Show, Multiple Income Streams, and a Purpose-Driven Career May 1, 2026 43:39 This week in the guest chair is Leah Collins, financial coach, speaker, and host of Maxxed Out, a powerful series helping people confront their finances and the relationships tied to them. But Leah’s journey didn’t start on TV, it started with a moment of truth: making the most money she ever had… and realizing she had nothing to show for it.In this episode, I sit down with Leah to unpack how she

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