Side Hustle Pro

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.

Episodes

January 15, 2026 27 mins

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 rules I want you to follow before c...
Mark as Played

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 idealiz...

Mark as Played
December 31, 2025 51 mins

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:

  • M...
Mark as Played

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 househ...

Mark as Played

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 quicker
  • My favorite content creation tech and tools, and much more!

Check out this episode and others on Apple Podca...

Mark as Played
December 11, 2025 17 mins

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 fou...

Mark as Played

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 marketin...

Mark as Played

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, an...

Mark as Played

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...

Mark as Played

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...

Mark as Played

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 ...

Mark as Played

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...

Mark as Played

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 strengths
  • Different service-based ideas you can launch today
  • How to valida...
Mark as Played

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 ...

Mark as Played

In this solo episode, I’m sharing the first three moves I’d make if I were starting a side hustle today and it’s not what you think.


Over the years, I’ve seen so many new side hustlers get caught up in the wrong things (logos, websites, Instagram aesthetic), and miss the real work that actually builds momentum and income. So I’m breaking down what I’d focus on right now if I had to start all over again.


These are the same fou...

Mark as Played

Being out of work can feel scary, the bills don’t stop, and self-doubt creeps in. But here’s the thing: this doesn’t have to be the end of your story. It can be the beginning of your expansion. Today, I’m sharing seven side hustles you can start right now to rebuild your confidence, earn income, and remind yourself that you have options.

Each of these hustles has the potential to bring in quick cash this month or grow into a long-te...

Mark as Played

For a long time, I believed pivoting meant I had failed. But now, I’ve learned that pivoting is actually proof that you’re still growing, still expanding, and still in motion.


In this episode, I open up about why I recently applied for a job, how it connects to everything I’ve built with Side Hustle Pro, and the lessons I’m learning in this new season.


In this episode, I share:

  • Why pivoting is feedback, not failure
  • How ever...
Mark as Played

In this solo Expansion Era episode, I’m opening up about a turning point in my journey: when I realized my life was running me, not the other way around. I share the step I took to shift that dynamic and the five powerful lessons that continue to guide me today. From building discipline like a muscle, to falling in love with the process, to tracking effort over outcomes, these lessons are helping me reclaim balance, confidence, and...

Mark as Played

This week, I’m back in the Expansion Era to go deeper into how to slow down without quitting, especially when business (or life) feels heavy. I’m sharing my own experiences navigating tough seasons in entrepreneurship, what it means to identify and pull your levers, and how I stabilize myself before getting back into action. From sponsorship slowdowns to shifting income streams, I walk you through the real strategies I use to find ...

Mark as Played
September 5, 2025 39 mins

This week in the guest chair is… me! I’m kicking off a new season with a solo episode to share what I’m calling my Expansion Era.

In this deeply personal and vulnerable episode, I open up about how I lost my mojo, what I’ve been navigating as a mom and entrepreneur, and the steps I’m taking to rebuild my confidence, health, and business.


In this episode I share:

  • The reality of postpartum depression, business setbacks, and navi...
Mark as Played

Popular Podcasts

    I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!

    Stuff You Should Know

    If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.

    The Joe Rogan Experience

    The official podcast of comedian Joe Rogan.

    The Breakfast Club

    The World's Most Dangerous Morning Show, The Breakfast Club, With DJ Envy, Jess Hilarious, And Charlamagne Tha God!

    SmartLess

    "SmartLess" with Jason Bateman, Sean Hayes, & Will Arnett is a podcast that connects and unites people from all walks of life to learn about shared experiences through thoughtful dialogue and organic hilarity. A nice surprise: in each episode of SmartLess, one of the hosts reveals his mystery guest to the other two. What ensues is a genuinely improvised and authentic conversation filled with laughter and newfound knowledge to feed the SmartLess mind. Subscribe to SiriusXM Podcasts+ to listen to new episodes of SmartLess ad-free and a whole week early. Start a free trial now on Apple Podcasts or by visiting siriusxm.com/podcastsplus.

Advertise With Us
Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2026 iHeartMedia, Inc.