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.
Author
Nicaila Matthews Okome | Side Hustle Pro Media
Category
Podcast website
Latest episode
Jul 7, 2026
Where to listen?
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Episodes
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...
510: How I'm Rebuilding After A Hard Season (feat. Monique Shields) 17.04.2026 49:49
In this episode, I’m joined again by Monique Shields, and this conversation felt like therapy, coaching, and truth-telling all in one. We went deep into something I’ve personally been navigating: what it actually looks like to move out of survival mode as a high-achieving woman, especially when life has been life-ing. We talked about the invisible weight many of us carry, from parenting to busines...
509: Opening Up About My Journey as an Autism Mom 10.04.2026 32:02
This episode is one of the most personal and vulnerable conversations I’ve ever shared. I’m opening up about my journey as an autism mom, from the early days of pregnancy and motherhood during the pandemic to navigating the realities of developmental delays, diagnoses, and advocacy. What started as subtle concerns about speech delays turned into a life-changing journey through early intervention,...
508: The Tax Mistakes Side Hustlers Make That Cost Them Thousands (And How to Avoid Them) 08.04.2026 34:11
If you’re a side hustler or solopreneur, taxes can go from simple to overwhelming real fast and the truth is, many entrepreneurs are quietly losing thousands of dollars just by not knowing what they don’t know. In this episode, I sat down with CPA and TurboTax Expert Lisa Greene-Lewis to break down the most common tax mistakes side hustlers make, from choosing the wrong business structure to...
507: The Hidden Cost of Waiting Until You're Ready 27.03.2026 28:46
If you’ve been waiting for the perfect moment to finally start that thing you said you’d do this year, this episode is your wake-up call. Because the truth is, that moment isn’t coming. This week, I’m pulling back the curtain on a very real, very messy week in my life and sharing why I decided to hit record anyway. From sick kids to mental clutter to a house that is far from organized, I had every...
506: 5 Simple Ways to Get Paid for What You Already Know 20.03.2026 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...
505: From YouTube Exec to Full-Time Creator: How Chanel Tyler Turned Content Creation Into 5-Figure Passive Income 13.03.2026 1:09:20
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 recommendations and insights from her background in beauty marketing. But after years of consulting with a creator c...
504: How to Go From Side Hustle to $1 Million | My Coaching Session with Dielle Charon 06.03.2026 1:06:43
This week in the guest chair is sales and business coach Dielle Charon, founder of For the 23% , where she helps women of color build profitable businesses and grow their income through coaching and entrepreneurship. Dielle shares how she went from earning $2,500 a month as a social worker with six-figure student loan debt to building a multi-seven-figure coaching business. Along the way, she expl...
503: She Got Laid Off…Then Built a YouTube Income to Pay Her Bills 27.02.2026 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...
502: My 12-Week Reset: Health, Money & Business 21.02.2026 30:57
This week on Side Hustle Pro, I’m sharing how I’m structuring my year through 12-week sprints, focusing on my health, my money, and elevating my Podcast Moguls program. I open up about navigating motherhood, sleep deprivation, and mindset work while still executing on big goals. Most importantly, I reflect on how my podcast has been the one constant through every season becoming my bri...
501: Laid Off: Now What? 5 Ways to Generate Income While You’re Unemployed 13.02.2026 21:27
In this solo episode, I’m sharing five real, practical ways to generate income during your in-between season. If you’re asking yourself, “I got laid off… now what? This episode will give you grounded, actionable steps to move forward and even some side hustle ideas! Highlights Include 00:00 – If you’ve been laid off, you are not alone 02:30 – Why invisibility is the real danger during unemployment...
500: I've Recorded 500 Podcast Episodes: Here's What I've Learned 06.02.2026 26:41
Side Hustle Pro is officially 500 episodes deep, and in this milestone episode, I’m taking time to reflect on what this journey has really taught me. I share the biggest lessons I’ve learned about consistency, networking, monetization, and why the podcast itself was never the end goal, the platform was. I also talk about what I wish I knew when I started, how podcasting helped me grow as a speaker...
499: How to Make Your First $1K Side Hustling 29.01.2026 33:20
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 that turn preparation into income without overbuilding, overthinking, or waiting until things feel perfect. If...
498: How to Start a Side Hustle Without Quitting Your Job 22.01.2026 22:38
In this solo episode, I’m breaking down how to start your side hustle without quitting your job or putting your paycheck at risk. I’m sharing what I’ve learned from building Side Hustle Pro from two very different places: one, when I was unemployed with plenty of time but no stability, and two, when I was working full-time at NPR with stability but limited time. What I’ve learned is this: there is...
497: 7 Side Hustles That Can Make Real Money 15.01.2026 27:43
In this episode of Side Hustle Pro , I break down seven side hustles you can start this month that have real income potential. This episode is all about building leverage through problem-solving businesses that can grow from side hustle to full-time income. In This Episode, I Share: Why your side hustle should be treated as leverage and a real business, not a hobby or just extra money The two rule...
496: The 12-Week Sprint Approach That Changed My Side Hustle Results 09.01.2026 21:55
In this solo episode, I’m sharing the exact 12 week sprint system that completely changed how I set and complete my goals. Instead of giving myself an entire year to “figure it out,” I learned that shrinking the timeline created clarity, urgency, and momentum. I walk you through how I choose my goals, break them down into manageable weekly actions, and build in a recalculation rule that allows for...
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