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Side Hustle Pro

Side Hustle Pro

Nicaila Matthews Okome | Side Hustle Pro Media 524 episodes Latest May 29, 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

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 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 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 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 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 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 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
511: Monica Cornitcher’s Journey From Personal Loss to Non-Alcoholic Cocktail Success Apr 24, 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 co
510: How I'm Rebuilding After A Hard Season (feat. Monique Shields) Apr 17, 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 business
509: Opening Up About My Journey as an Autism Mom Apr 10, 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) Apr 8, 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 too
507: The Hidden Cost of Waiting Until You're Ready Mar 27, 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

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