Side Hustle Pro
Side Hustle Pro

Side Hustle Pro

Nicaila Matthews Okome | Side Hustle Pro Media

Overview
Episodes

Details

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.

Recent Episodes

492: Rebuilding My Business After Burnout
DEC 11, 2025
492: Rebuilding My Business After Burnout

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 I was. It’s about becoming someone who doesn’t abandon herself on the way to her goals.

If you're feeling depleted, questioning your confidence, or trying to rebuild your business after a hard season, this one’s for you.


Watch this whenever you need a reminder that you can rebuild without rushing yourself.


RESOURCES MENTIONED

Join my newsletter for behind-the-scenes support as you rebuild your business:

https://sidehustlepro.co/newsletter

Register for my next free Podcast Moguls training on how to start the podcast that builds your exit plan:

https://podcastmoguls.com


CONNECT WITH ME

Instagram:https://www.instagram.com/sidehustlepro

Podcast: Side Hustle Pro

Business inquiries: [email protected]


CHAPTERS

00:00 Realizing burnout

01:20 When exhaustion becomes normal

03:05 The power of rest

04:40 Relearning prioritization

06:30 Time boundaries and rebuilding my schedule

09:30 Money, fear, and shrinking my confidence

12:40 Self-care and putting myself back in the budget

15:00 What rebuilding actually looks like

17:00 Your next step


Hosted on Acast. See acast.com/privacy for more information.

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17 MIN
491: 9 Side Hustles You Can Start Today That Could Replace Your 9-5
DEC 4, 2025
491: 9 Side Hustles You Can Start Today That Could Replace Your 9-5

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 brand on side hustling! 


In this episode I share:

  • Nine unique and and high-profit side hustles that can fully replace your 9-5
  • The side hustles former guests of Side Hustle Pro have had major success with
  • Why closing the gap between your ideas and actually starting is the key to your business


Highlights include:

  • 01:45 Cleaning services
  • 06:22 Faceless podcast
  • 07:57 Virtual assistant
  • 12:16 Social media marketing
  • 15:25 Short-form video editor 
  • 21:15 Podcast/YouTube channel manager
  • 22:30 AI integration specialist
  • 26:34 Corporate training and coaching
  • 29:40 Done-for-you service provider
  • 32:30 Why you should start now


Check out episode 491 of Side Hustle Pro podcast out now on Apple PodcastsSpotify, and YouTube


Links mentioned in this episode


Click here to subscribe via RSS feed (non-iTunes feed): http://sidehustlepro.libsyn.com/rss


Announcements

Join our Facebook Community

If 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/facebook


Guest Social Media Info

Side Hustle Pro – @sidehustlepro

#SideHustlePro


Hosted on Acast. See acast.com/privacy for more information.

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34 MIN
490: She Left Corporate and Built a 7-Figure Business
NOV 26, 2025
490: She Left Corporate and Built a 7-Figure Business

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 blends corporate strategy, healing, and public speaking to help organizations and people thrive without burnout.


In this episode, Lakila opens up about the moment she walked away from the “known,” how she rebuilt her identity outside of corporate titles, and how speaking became a major accelerator in her business growth. She also breaks down the inner and outer transformation required to grow with your purpose, honor your well-being, and lead from a place of wholeness.


In This Episode, Dr. Lakila Shares:

  • The pivotal moment she knew she had to leave corporate America
  • How she and her sister built ISee Technologies into a 7-figure consulting firm
  • Why public speaking became a core revenue driver in her business
  • How personal healing shaped her approach to leadership and entrepreneurship
  • Her framework for helping organizations and individuals thrive without burning out



Highlights Include

00:00: Intro

02:10: Starting IC Technologies with her sister Camille

04:30: Becoming a speaker and author and how speaking scaled her impact

08:20: Building a disability-led, wellness-centered company

12:00: How corporate strategy + personal healing became her business superpower

16:15: The growth that came after walking away from the “known”

20:45: Helping organizations cultivate inclusion and sustainable wellness

26:30: Advice for anyone ready to pivot from corporate into purpose


Watch this episode on YouTube and listen on all podcast apps

Apple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323

Spotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8t?si=8daf52a57e054042


Links Mentioned in This Episode


Click here to subscribe via RSS feed (non-iTunes feed): http://sidehustlepro.libsyn.com/rss


Guest Social Media Info

Lakila's Instagram: https://www.instagram.com/lakilaj/

ISee Technologies Website: https://www.iseetechinc.com/

Side Hustle Pro – @sidehustlepro

#SideHustlePro


Hosted on Acast. See acast.com/privacy for more information.

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54 MIN
489: How to Start a Side Hustle with AI (feat. Nadeen Matthews Blair)
NOV 19, 2025
489: How to Start a Side Hustle with AI (feat. Nadeen Matthews Blair)

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 to the whisper, and chose a new path.


That path led her to Crescent Advisory Group, where she now teaches professionals, creatives, and new entrepreneurs how to use AI with confidence. What’s wild is that she built the entire business using just four beginner-friendly AI tools and today, she’s breaking them all down for you.


Whether you’re in a pivot, launching a side hustle, or trying to understand where AI fits into your next chapter, this episode will give you clarity, confidence, and a simple starting point.


In This Episode, Nadeen Shares:

  • How she pivoted from a demanding corporate career into full-time entrepreneurship
  • Why early consulting and workshop opportunities found her before she officially launched
  • How AI tools like Perplexity, Gamma, Looka, and Namelix helped her build her brand, website, and business foundation fast
  • Why AI is the most powerful leverage tool for side hustlers in 2025
  • How redefining success around flexibility, family, and purpose shaped her new chapter
  • What she’s teaching thousands of people in her beginner-friendly AI webinars


If you’ve been feeling the pull to pivot or you’re curious about how to use AI without feeling overwhelmed, this is your episode.


Watch Episode 489 on YouTube and listen on all podcast apps.


Links mentioned in this episode

Crescent Advisory Group: http://crescentadvisorygroup.com

ChatGPT

Perplexity

NameLix

Gamma

Lovable

MIT AI Courses

Alicia Little’s AI Innovation Program


Guest Social Media Info

Side Hustle Pro – @sidehustlepro: https://www.instagram.com/sidehustlepro/

Nadeen Matthews Blair IG: https://www.instagram.com/nadeenmatthewsblair/

Nadeen Matthews Blair LinkedIn: https://www.linkedin.com/in/nadeenmatthews/


Hosted on Acast. See acast.com/privacy for more information.

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58 MIN
488: The Power in the Pivot: How Keewa Nurullah Is Rebuilding After Closing Her Dream Business
NOV 12, 2025
488: The Power in the Pivot: How Keewa Nurullah Is Rebuilding After Closing Her Dream Business

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 truly looks like to evolve as an entrepreneur, navigating economic shifts, changing customer behavior, and the emotional side of letting go of something you built from the ground up. Today she’s channeling those lessons into her work as a strategist and host of Circulate, a monthly community event that “love-bombs” local shops with intentional support and helps other founders build thriving, purpose-driven businesses on their own terms.


In this episode, she shares:

  • The courage to walk away from a business 
  • What retail taught her about leadership, money, and boundaries
  • The realities of pivoting after success
  • How she’s creating new pathways for community-minded entrepreneurs


Highlights Include

00:00 Intro

03:10 Launching Kido and building community through culture

08:45 Getting national recognition (including Barack Obama’s shout-out)

13:20 The moment she knew it was time to close her storefront

17:15 Navigating shifting customer habits post-pandemic

22:40 Starting over as a strategist and redefining success

27:00 Creating Circulate and supporting small businesses

33:15 Lessons on resilience, rest, and rediscovering your "why"

40:00 Advice for entrepreneurs in transition


Watch episode 488 on YouTube and listen on all podcast apps


Links mentioned in this episode


Click here to subscribe via RSS feed (non-iTunes feed): http://sidehustlepro.libsyn.com/rss


Announcements

Join our Facebook Community

If 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/facebook


Guest Social Media Info

Instagram: @kiwimercury


Hosted on Acast. See acast.com/privacy for more information.

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52 MIN