

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 "The Budgetnista" Aliche, and more! Hosted on Acast. See acast.com/privacy for more information.
Episodes
Mentioned books

Nov 19, 2025 • 58min
489: How to Start a Side Hustle with AI (feat. Nadeen Matthews Blair)
Nadeen Matthews Blair, founder of Crescent Advisory Group and former corporate executive, shares her transformative journey from the corporate world to entrepreneurship. She emphasizes the power of AI tools like ChatGPT, Namelix, and Looka in building a business quickly. Nadeen discusses how offering free workshops helped validate her services and highlights AI as a game changer for side hustlers. She also reflects on redefining success to prioritize flexibility and impact while encouraging others to engage with technology constructively.

Nov 12, 2025 • 52min
488: The Power in the Pivot: How Keewa Nurullah Is Rebuilding After Closing Her Dream Business
In this engaging discussion, Keewa Nurullah, an artist and small-business strategist known for founding the culturally rich children's boutique Kiddo, shares her entrepreneurial journey. She bravely closed her shop after significant success, reflecting on the emotional and financial factors behind that decision. Topics include adapting to post-pandemic customer behavior, the challenges of funding for small businesses, and her new initiative, Circulate, aimed at supporting local retailers. Keewa emphasizes the importance of community connection and redefining success on one's own terms.

Nov 5, 2025 • 27min
487: Mindset Hacks For Every Business Owner
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 share:The mindset hacks I use, like reframing limiting beliefs, to conquer my goals How to break down your goals into actionable steps to avoid overwhelm My experience with imposter syndrome and how I continuously overcome itHighlights include:00:00 Intro01:00 Battling imposter syndrome04:14 Breaking free from overthinking08:05 Confidence is key14:05 Master Instagram Challenge17:50 Building mental resilience 21:28 Actionable steps to a mindset changeCheck out episode 487 of Side Hustle Pro podcast out now on Apple Podcasts, Spotify, and YouTubeLinks mentioned in this episodeSide Hustle Pro YouTube: https://www.youtube.com/@SideHustlePro Side Hustle Pro Instagram: https://www.instagram.com/sidehustlepro/ SHP Done Is Better Than Perfect Episode: https://www.youtube.com/watch?v=naMuG3Abzmo SHP Denise Woodard Episode: https://www.youtube.com/watch?v=wjQqNBd8-xA Click here to subscribe via RSS feed (non-iTunes feed): http://sidehustlepro.libsyn.com/rssAnnouncementsJoin our Facebook CommunityIf you’re looking for a community of supportive side hustlers who are all working to take our businesses to the next level, join us here: https://sidehustlepro.co/facebookGuest Social Media InfoSide Hustle Pro – @sidehustlepro#SideHustlePro Hosted on Acast. See acast.com/privacy for more information.

Oct 29, 2025 • 26min
486: How to Side Hustle With a Full-Time Job
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 could reclaim. Here’s how you can do the same.In this episode I share about:The time you’re losing and how to identify your top time wastersThe 3-Step Hustler’s Time Plan: how to maximize your timeHow to build a system and schedule that work for youHighlights include: 00:00 Intro01:45 Identify your biggest time traps06:42 Reclaim your time12:35 Power hour: get more done in less time16:15 Leverage your days off18:30 Protect your side hustle hours21:20 Choose a schedule that fits your life23:40 Final thoughts and recapCheck out episode 486 of Side Hustle Pro podcast out now on Apple Podcasts, Spotify, and YouTubeLinks mentioned in this episodeNicaila’s Website: https://sidehustlepro.co/Nicaila’s Instagram: https://www.instagram.com/sidehustlepro/ Nicaila’s LinkedIn: https://www.linkedin.com/in/nicailamatthewsokome Brown Ambition Podcast: https://brownambitionpodcast.com/ Click here to subscribe via RSS feed (non-iTunes feed): http://sidehustlepro.libsyn.com/rssAnnouncementsJoin our Facebook CommunityIf you’re looking for a community of supportive side hustlers who are all working to take our businesses to the next level, join us here: https://sidehustlepro.co/facebookGuest Social Media InfoSide Hustle Pro – @sidehustlepro#SideHustlePro Hosted on Acast. See acast.com/privacy for more information.

Oct 24, 2025 • 23min
485: How to Turn Your Skills Into a Side Hustle
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 Intro02:00 Three key steps05:30 Monetizable skills09:30 How to get paid sooner, not later15:00 Actionable homeworkCheck out episode 485 of Side Hustle Pro podcast out now on Apple Podcasts, Spotify, and YouTubeLinks mentioned in this episodePortia Obeng SHP episode: https://youtu.be/4qkgObsQ7pA?si=BySviTQaeTqgVa01 Nicaila’s Instagram: https://www.instagram.com/sidehustlepro/ Nicaila’s LinkedIn: https://www.linkedin.com/in/nicailamatthewsokome FREE Survey Template: https://sidehustlepro.lpages.co/side-hustle-survey/ Click here to subscribe via RSS feed (non-iTunes feed): http://sidehustlepro.libsyn.com/rssAnnouncementsJoin our Facebook CommunityIf you’re looking for a community of supportive side hustlers who are all working to take our businesses to the next level, join us here: https://sidehustlepro.co/facebookGuest Social Media InfoSide Hustle Pro – @sidehustlepro#SideHustlePro Hosted on Acast. See acast.com/privacy for more information.

Oct 16, 2025 • 42min
484: Demetria Lucas on Taking Career Risks and Embracing Pivots
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 travel company, and more gives her freedom to enjoy life outside of workingThe enormous impact traveling the world has had on her work, leading her to author three books on travel How she stayed resilient through personal challenges and self-doubtHighlights Include:00:00 Intro03:36 Breaking into the book industry08:20 Streams of steady income13:45 Building a personal brand and podcast24:08 Traveling the world27:00 The ups and downs of finances in freelancing36:15 Tips for entrepreneurs Check out episode 484 of Side Hustle Pro podcast out now on Apple Podcasts, Spotify, and YouTubeLinks mentioned in this episodeDemetria’s Website: https://www.demetriallucas.com/ Demetria’s Instagram: https://www.instagram.com/demetriallucas Demetria’s Facebook: https://www.facebook.com/demetriallucas Ratchet and Respectable Podcast: https://podcasts.apple.com/us/podcast/ratchet-respectable/id1449001372 TikTok: https://www.tiktok.com/ Click here to subscribe via RSS feed (non-iTunes feed): http://sidehustlepro.libsyn.com/rssAnnouncementsJoin our Facebook CommunityIf you’re looking for a community of supportive side hustlers who are all working to take our businesses to the next level, join us here: http://sidehustlepro.co/facebookGuest Social Media InfoSide Hustle Pro – @sidehustlepro#SideHustlePro Hosted on Acast. See acast.com/privacy for more information.

Oct 10, 2025 • 23min
483: The First 3 Moves I’d Make If I Were Starting a Side Hustle Today
Discover the key first moves to kickstart a side hustle, focusing on the problem you solve and your target audience. Learn why validation calls are crucial for testing your ideas and adjusting your approach. Uncover the difference between a website and a funnel, and why a simple funnel can boost your sales. Find out how launching an initial low-cost offer helped build confidence and client engagement. Embrace the 'Do It Ugly' philosophy to gain experience and credibility quickly!

Oct 4, 2025 • 28min
482: 7 Side Hustles That Pay When You’re Unemployed
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-term business. Momentum builds confidence, and confidence builds opportunity. In this episode I share:Seven side hustles you can start right now if you’re unemployed or need extra cash—from digital products to service-based opportunities.How to use your existing skills and everyday tools like Canva, ChatGPT, and social platforms to quickly generate income.Why momentum matters more than perfection, and how even a small win can rebuild your confidence.The importance of direct outreach—emails, texts, and personal asks—when you need to make money fast, instead of relying solely on social media.Highlights include:00:00 Intro02:20 Side Hustle #1: Career Story Studio04:40 Side Hustle #2: Digital Templates Shop07:06 Side Hustle #3: TikTok Shop Seller09:29 Side Hustle #4: Airbnb Co-Host13:59 Side Hustle #5: UGC Creator16:20 Side Hustle #6: AI Consultant18:44 Side Hustle #7: Fractional Ops Manager23:28 Final thoughts on making money now25:32 Closing thoughts + live class inviteLinks mentioned in this episode:Register for my free class: Start the Podcast That Builds Your Exit Plan: https://sidehustlepro.co/freetrainingSide Hustle Pro – @sidehustleproSide Hustle Pro Nicaila Matthews Okome Hosted on Acast. See acast.com/privacy for more information.

Sep 26, 2025 • 25min
481: Why Pivoting Isn’t Failure (My Real Story)
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 failureHow every pivot stacks and nothing is wastedThe dangers of comparison and how to release shameWhy pivots prepare you for your next expansion seasonHighlights include: 00:00 Intro 02:20 What pivoting really means 07:05 Why I applied for a new role 11:45 Lessons from past pivots that shaped Side Hustle Pro 16:20 How comparison creates false shame 20:59 Why pivots keep you in motion 25:00 The role of podcasting in creating new opportunities 28:00 Closing thoughts + live class inviteWatch episode 481 on YouTube and listen on all podcast appsLinks mentioned in this episodeRegister for my free class: https://sidehustlepro.lpages.co/your-first-1000-downloads/AnnouncementsIf you’re looking for a community of supportive side hustlers who are all working to take our businesses to the next level, join us here: http://sidehustlepro.co/facebookClick here to subscribe via RSS feed (non-iTunes feed): sidehustlepro.libsyn.com/rssSocial MediaSide Hustle Pro – @sidehustlepro#SideHustlePro Hosted on Acast. See acast.com/privacy for more information.

Sep 19, 2025 • 25min
480: My Life Was Running Me Until I Took This Step
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 control. I’m still in the process myself, but I know these insights can help you start running your life, too.In this episode I share:Why focusing on the muscle you’re building matters more than the resultHow to fall in love with the process and romanticize the mundaneThe importance of tracking the process, not just the outcomesHow to recognize and adjust for your shortcomingsWhy letting go of rigid expectations opens the door to more winsHighlights include:00:00 Intro02:26 Lesson 1: Focus on the muscle, not the results07:12 Lesson 2: Fall in love with the process11:24 Lesson 3: Track the process, not the result16:05 Lesson 4: Adjust for your shortcomings21:16 Lesson 5: Let go of expectations & celebrate small wins25:32 Closing thoughts + invitation to my live classLinks mentioned on this episodeRegister for my free class: https://sidehustlepro.lpages.co/your-first-1000-downloads/Click here to subscribe via RSS feed (non-iTunes feed): http://sidehustlepro.libsyn.com/rssAnnouncementsIf you’re looking for a community of supportive side hustlers who are all working to take our businesses to the next level, join us here: http://sidehustlepro.co/facebookSocial Media InfoSide Hustle Pro – @sidehustlepro#SideHustlePro Hosted on Acast. See acast.com/privacy for more information.


