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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

49:49

510: Why High-Achieving Women Struggle to Outsource...

Side Hustle Pro ·

2026/04/17

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 to unexpected life challenges, and how that impacts the way we show up, make decisions, and even spend

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32:02

509: Opening Up About My Journey as an Autism Mom

Side Hustle Pro ·

2026/04/10

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, therapy, and eventually receiving an official autism diagnosis for my son. Along the way, I’ve had to

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34:11

508: The Tax Mistakes Side Hustlers Make That Cost...

Side Hustle Pro ·

2026/04/08

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 early to missing out on key deductions and failing to stay organized throughout the year. We also unpack what

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28:46

507: The Hidden Cost of Waiting Until You're Ready

Side Hustle Pro ·

2026/03/27

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 reason to wait. But instead, I leaned into a powerful reminder: progress doesn’t require perfection.In

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23:58

506: 5 Simple Ways to Get Paid for What You Already Know

Side Hustle Pro ·

2026/03/20

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 down five simple and practical ways to turn your existing skills, experiences, and knowledge into income

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1:09:20

505: From YouTube Exec to Full-Time Creator: How...

Side Hustle Pro ·

2026/03/13

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 commerce platform that generated over 80% of her income, everything changed when the company suddenly shut

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1:06:43

504: How to Go From Side Hustle to $1 Million | My...

Side Hustle Pro ·

2026/03/06

This week in the guest chair is sales and business coach Dielle McMillan, 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 explains why traditional jobs often undervalue your skills, how to identify the expertise you can monetize,

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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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118 results

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