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PODCAST

Side Hustle Pro

Nicaila Matthews Okome | Side Hustle Pro Media

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

business entrepreneurship

All Episodes

56:35

503: She Got Laid Off…Then Built a YouTube Income to...

Side Hustle Pro ·

2026/02/27

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 products, virtual assistant work, and strategic financial decisions like bringing on a roommate.If you’ve been

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30:57

502: My 12-Week Reset: Health, Money & Business

Side Hustle Pro ·

2026/02/21

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 bridge out of corporate and my foundation for long-term leverage.Highlights Include00:00: Why I use 12-week

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21:27

501: Laid Off: Now What? 5 Ways to Generate Income...

Side Hustle Pro ·

2026/02/13

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 Include00:00 – If you’ve been laid off, you are not alone02:30 – Why invisibility is the real danger during unemployment04:05 – Using content creation as a visibility tool07:20 – Turning alumni and professional networks into

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26:41

500: I've Recorded 500 Podcast Episodes: Here's What...

Side Hustle Pro ·

2026/02/06

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 and business owner, and why playing the long game has paid off in ways I never could have planned.If

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33:20

499: How to Make Your First $1K Side Hustling

Side Hustle Pro ·

2026/01/29

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 you’ve been stuck planning, tweaking, or doubting yourself, this episode will help you move forward with

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22:38

498: How to Start a Side Hustle Without Quitting Your...

Side Hustle Pro ·

2026/01/22

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 no “perfect” situation for side hustling. What matters is how you build, not whether you quit your job

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27:43

497: 7 Side Hustles That Can Make Real Money

Side Hustle Pro ·

2026/01/15

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 moneyThe two rules I want you to follow before choosing a side hustle: don’t try everything at once, and focus on solving

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21:55

496: The 12-Week Sprint Approach That Changed My Side...

Side Hustle Pro ·

2026/01/09

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 real life instead of an idealized version of it.If you have ever started the year motivated only to feel

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51:24

495: Breaking My Own Glass Ceiling

Side Hustle Pro ·

2025/12/31

This week we’re changing it up and I’m sitting in the guest chair. In this special “podcast swap” episode of Side Hustle Pro, I’m sharing an interview from the podcast To Tell You The Truth with host and Podcast Moguls student Brittany Sharpton. We dive into the concept of self-imposed barriers and how they can prevent entrepreneurs, especially Black women, from realizing their full potential.In this episode I share:My journey to reclaiming my power in spaces where Black women aren’t usually

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1:17:05

494: Owning Manhattan’s Tricia Lee: From Beauty Mogul...

Side Hustle Pro ·

2025/12/24

This week in the guest chair we have Tricia Lee, powerhouse real estate broker, star of Netflix’s Owning Manhattan, and founder and leader of the highly talented Tricia Lee Team at Serhant.Tricia sold over $200M in her solo career before joining Serhant and simultaneously joining forces with her partner, Jeffrey St. Arromand. Through the power of partnership, authenticity, and personal branding, Tricia has become a household name in real estate and media.In this episode, Tricia shares:How she

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22:23

493: How To Make Content For Your Business In Less...

Side Hustle Pro ·

2025/12/19

As an entrepreneur, content creation has become a huge part of expanding a business. So this week I’m sharing 4 tips that have helped me take the pressure off creating awesome content while running a business.In this episode I’m sharing:How to optimize your recording sessions to get content done quickerMy favorite content creation tech and tools, and much more!Check out this episode and others on Apple Podcasts, Spotify, and YouTubeLinks mentioned in this episodeFree Side Hustle Guide:

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17:22

492: Rebuilding My Business After Burnout

Side Hustle Pro ·

2025/12/11

Rebuilding my business after burnout wasn’t one big breakthrough. It was a series of small, honest shifts that finally brought me back to myself.Rest. Prioritization. Time boundaries. Financial honesty. And the self-care I kept putting off because I felt guilty investing in myself.In today’s episode of The Expansion Era, I’m sharing what this rebuilding season has really looked like for me as a mom of two, a wife, and a founder trying to get her mojo back. This chapter isn’t about going back to who

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34:50

491: 9 Side Hustles You Can Start Today That Could...

Side Hustle Pro ·

2025/12/04

Are you ready to finally take the leap and start your side hustle, but don’t know where to start? This week we are outlining nine high-potential side hustles that can realistically scale to replace or significantly supplement your full-time income.Now these are not quick-fix ideas, these are long-term businesses that can bring you recurring revenue by leveraging automation tools (especially AI), and refining your marketing so clients find and trust you. Take it from someone who has built an entire

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54:33

490: She Left Corporate and Built a 7-Figure Business

Side Hustle Pro ·

2025/11/26

This week in the guest chair, Dr. Lakila Bowden shares her powerful journey from leading thousands inside Fortune 500 companies to co-founding ISee Technologies, a Black sister-owned, disability-led consulting firm now earning seven figures.After leaving corporate in 2019, Lakila teamed up with her sister, Camille, to build a company trusted by brands like Disney, Kraft Heinz, and the EPA for high-impact training, inclusion, and workforce wellness programs. What makes her work different is how she

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58:25

489: How to Start a Side Hustle with AI (feat. Nadeen...

Side Hustle Pro ·

2025/11/19

This week in the guest chair, we have someone very special, my sister, Nadeen Matthews Blair and her pivot story is going to speak directly to anyone who’s ever felt called to reinvent themselves.After 20 years in banking, management consulting, and C-suite leadership, Nadeen hit a point where the titles, the pressure, and the nonstop demands were no longer aligned with the life she wanted for herself and her family. So she did what so many high-achieving women fear doing: she stepped back, listened

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52:12

488: The Power in the Pivot: How Keewa Nurullah Is...

Side Hustle Pro ·

2025/11/12

This week in the guest chair we have Keewa Nurullah, artist, entrepreneur, and small-business strategist you may remember as the founder of Kido, the beloved South Loop children’s boutique that brought color, culture, and community to families across Chicago.After six powerful years in business, and national recognition that included a shout-out from President Barack Obama, Keewa made the bold decision to close her brick-and-mortar store and start over.In this episode, Keewa opens up about what it

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27:27

487: Mindset Hacks For Every Business Owner

Side Hustle Pro ·

2025/11/05

This week we’re diving into how to shift your mindset to set yourself up for success. Here’s the thing I’ve learned over the years that your mindset isn’t just a nice-to-have; it’s the foundation for everything you’re trying to build. Whether it’s pushing past fear to finally launch your business, staying consistent when sales are slow, or silencing that little voice in your head saying, ‘Who are you to do this?’ it all comes back to how you think and how you show up for yourself.In this episode I

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26:04

486: How to Side Hustle With a Full-Time Job

Side Hustle Pro ·

2025/10/29

Welcome back to the Side Hustle Pro podcast, your headquarters for turning passion projects into profitable businesses! I’m Nicaila, and today we’re talking about how to find (and protect) the time you need to build your side hustle.I get it: Working a full-time job, juggling family commitments, and trying to live your life can make your side hustle goals feel impossible. But trust me, it’s not. I used to think I had zero free hours, but as soon as I did a reality check, I found pockets of time I

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22:39

485: How to Turn Your Skills Into a Side Hustle

Side Hustle Pro ·

2025/10/24

Always wanted to start a side hustle but didn’t know what industry to try? This week I’m breaking down the exact process of identifying the skills you do effortlessly and turning them into a profitable side hustle.In this episode I share:How to pinpoint the skills hiding in your “blind spot”The importance of surveying your network to confirm your strengthsDifferent service-based ideas you can launch todayHow to validate your offers quickly and start getting paid soonerHighlights include:00:00

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42:21

484: Demetria Lucas on Taking Career Risks and...

Side Hustle Pro ·

2025/10/16

This week we’re airing my first ever live podcast! I had the opportunity to sit down with author, journalist, and media powerhouse Demetria Lucas at the On Air Fest in Brooklyn, NY.From launching A Belle in BK to building an empire that spans books, film, podcasting, and more, Demetria has mastered the art of evolving and thriving as a multi-hyphenate entrepreneur. Taking risks and flawlessly pivoting has paid off.In this episode she shares:How prioritizing steady income through podcasting, owning a

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111 results

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