Nicaila Matthews Okome | Side Hustle Pro Media
Side Hustle Pro
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. Side Hustle Pro features interviews with inspiring Black women entrepreneurs who started out as side hustlers, including interviews with Myleik Teele, Morgan DeBaun, Tiffany "The Budgetnista" Aliche, and more! Hosted on Acast. See acast.com/privacy for more information.
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Nicaila Matthews Okome | Side Hustle Pro Media
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23 жов 2026
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Why Everyone and Their Mother Has a Podcast 23.10.2026 33:22
In this solo episode, I break down why so many people are starting shows right now, drawing on 10 years of running Side Hustle Pro, which I launched in 2016 and have grown past 10 million downloads. I walk through three things a podcast can be: a networking tool, a bridge from where you've been to where you want to go, and a launch pad. I share how I grew the show with a small paid promotion b...
Life Update: How I'm Rebuilding My Business Around My Life 16.10.2026 37:14
I kept putting off this solo episode because I did not want to get camera-ready. So I took the camera out of the picture. This audio-only life update is about the changes that helped me feel like myself again, a year after sharing that I was burned out. I share how I started building my business around my life as a mother, why I am focused on Podcast Moguls and SHIFT, and what I learned from launc...
5 Simple Ways to Get Paid for What You Already Know 30.09.2026 23:58
One of the biggest misconceptions I see when it comes to making money is the belief that you need to start from scratch. A new certification, a brand new idea, or a completely different skill set. But the truth is, most of us already have everything we need. The real problem is not a lack of knowledge, it is not knowing how to package and position what we already know. In this episode, I break dow...
She Got Laid Off…Then Built a YouTube Income to Pay Her Bills 25.09.2026 56:35
This week in the guest chair, Symone’ Austin shares her powerful journey from being laid off to building a thriving YouTube platform. After recording and posting her layoff conversation, her video went viral and became the turning point in her entrepreneurial journey. In this episode, she breaks down how she built multiple income streams through YouTube ad revenue, brand partnerships, digital prod...
From a Food Blog to a $500K-a-Year Media Business: How Jannese Torres Built Yo Quiero Dinero 18.09.2026 53:17
In this episode, I sat down with Jannese Torres, host of the Yo Quiero Dinero podcast, to talk about how she went from a corporate career in engineering, pharmaceuticals, and consumer manufacturing to building a $500K-a-year media business. Jannese shares how getting laid off pushed her to take entrepreneurship seriously and how her food blog, Delish D'Lites, became her first profitable side hustl...
How to Make Your First $1K Side Hustling 11.09.2026 33:20
If this resonated with you, here are additional resources: ⭐ APPLY TO SHIFT: https://sidehustlepro.co/shift You do not need a million dollars to change your life, you need your first $1,000 . In this solo episode, I’m breaking down why the first $1K is such a pivotal milestone for side hustlers and how it shifts everything from theory to proof. I walk you through the exact decisions and actions t...
From YouTube Exec to Full-Time Creator: How Chanel Tyler Turned Content Creation Into 5-Figure Passive Income 28.08.2026 1:09:20
If this resonated with you, here are additional resources: ⭐ APPLY TO SHIFT: https://sidehustlepro.co/shift This week in the guest chair is Chanel Tyler, a strategist, creator, and self-described “contentpreneur” who has worked across investment banking, luxury marketing, and YouTube before stepping fully into entrepreneurship. Chanel built her reputation online by sharing trusted product recomme...
How Karen Young Built OUI the People 21.08.2026 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 th...
She Left Corporate Law, Went Back to Work, and Still Built a Global Fashion Brand 14.08.2026 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 07.08.2026 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 realitie...
7 Things I Had to Unlearn Before Leaving My Corporate Job 31.07.2026 43:40
If this resonated with you, here are additional resources: ⭐ APPLY TO SHIFT: https://sidehustlepro.co/shift In 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 menta...
Why She Pulled Her Brand Out of Whole Foods After 26 Years | Dawn Fitch, Founder of Pooka Pure and Simple 30.07.2026 52:12
If this resonated with you, here are additional resources: ⭐ APPLY TO SHIFT: https://sidehustlepro.co/shift In 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...
How Roxy Couse Replaced Her Corporate Title With Her Personal Brand 24.07.2026 49:42
If this resonated with you, here are additional resources: ⭐ APPLY TO SHIFT: https://sidehustlepro.co/shift In 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 cont...
She Emptied Her Retirement to Open a Tea Brand (Jamila Wright, Founder of Brookyn Tea) 17.07.2026 1:00:11
If this resonated with you, here are additional resources: APPLY TO SHIFT: https://sidehustlepro.co/shift In 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...
How Real Housewives of Atlanta's Cynthia Bailey and Co-Founder Dana Hill-Robinson Built Glowissima Skincare 14.07.2026 1:02:15
If this resonated with you, here are additional resources: ⭐ APPLY TO SHIFT: https://sidehustlepro.co/shift In 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...
520: How Jotaka Eaddy Built a Movement of 44,000 Black Women Overnight 07.07.2026 1:03:42
If this resonated with you, here are additional resources: ⭐ APPLY TO SHIFT: https://sidehustlepro.co/shift In 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 communi...
519: After 10 Million Downloads, Here’s What I Learned 20.06.2026 25:47
If this resonated with you, here are additional resources: ⭐ APPLY TO SHIFT: https://sidehustlepro.co/shift When 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 n...
518: The ONE skill you need to learn before you QUIT 12.06.2026 30:12
If this resonated with you, here are additional resources: ⭐ APPLY TO SHIFT: https://sidehustlepro.co/shift In 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...
517: After Quitting My 6-Figure Job to Launch My Own Business Here’s What I Learned 05.06.2026 26:05
If this resonated with you, here are additional resources: ⭐ APPLY TO SHIFT: https://sidehustlepro.co/shift In 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...
516: From Caregiver to CEO: How Camille Joy Turned Her Son’s Diagnosis Into a Movement 29.05.2026 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 22.05.2026 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 15.05.2026 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 08.05.2026 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...
512: How Leah Collins Turned Financial Mistakes Into a TV Show, Multiple Income Streams, and a Purpose-Driven Career 01.05.2026 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 sh...
511: Monica Cornitcher’s Journey From Personal Loss to Non-Alcoholic Cocktail Success 24.04.2026 43:42
I sat down with Monica Cornitcher, CEO and co-founder of Medase Cocktails, a premium non-alcoholic beverage brand redefining what it means to drink without alcohol. What started as a simple desire for a real cocktail experience without the after-effects turned into a six-figure investment and a fast-growing brand that’s now catching the attention of major retailers. Monica shares how she and her c...
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