Side Hustle Pro

Nicaila Matthews Okome | Side Hustle Pro Media
  • 5.0 (2)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY

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.

  1. 495: Breaking My Own Glass Ceiling

    3 DAYS AGO

    495: Breaking My Own Glass Ceiling

    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 empowered- and why I’m constantly reminding myself that I’m that girlSteps to take to combat the fear and negative self-talk that often creep inWhat feeds my soul and the lessons I’m learning every day- even as a seasoned entrepreneur Insights from my Podcast Moguls course and how I’ve seen Brittany grow after being a student  Highlights Include: 00:00 Intro 03:30 From corporate to entrepreneur  09:55 The importance of having a side hustle  11:45 Overcoming biases 17:30 How to show up as a working mom 22:00 Getting your mojo back  27:15 Overcoming the limitations of the patriarchy 37:04 Tips to feed your soul 41:15 Beating fear and imposter syndrome Check out episode 495 of Side Hustle Pro podcast out now on Apple Podcasts, Spotify, and YouTube Links mentioned in this episode Brittany’s Instagram: https://www.instagram.com/britthappenshq/ To Tell You The Truth Pod: https://www.instagram.com/totellyouthetruthpod/ Nicaila’s Instagram: https://www.instagram.com/sidehustlepro/ How To Make Money Podcasting Course: https://sidehustlepro.lpages.co/your-first-1000-downloads/ Management Leadership For Tomorrow: https://mlt.org/ Mel Robbins Podcast, Let Go of Negative Thoughts: https://www.melrobbins.com/podcasts/episode-198 Jen Sincero’s Book: https://jensincero.com/ Walk Through Fire: https://www.amazon.com/Walk-Through-Fire-Memoir-Triumph-ebook/dp/B0BXM51HXN Get Good With Money: https://getgoodwithmoney.com/  Click here to subscribe via RSS feed (non-iTunes feed): http://sidehustlepro.libsyn.com/rss Hosted on Acast. See acast.com/privacy for more information.

    51 min
  2. 494: Owning Manhattan’s Tricia Lee: From Beauty Mogul to Real Estate Titan

    24/12/2025

    494: Owning Manhattan’s Tricia Lee: From Beauty Mogul to Real Estate Titan

    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 successfully managed the pivot from beauty to real estate and television Why she makes it a point to share her journey while also marketing her businessHow content creation has helped her close real estate dealsHow she has stayed true to herself and blocked out opinions, jobs, and people who don’t align with her goalsAnd so much more! Highlights Include: 00:00 Intro  03:14 Discovering identity 13:00 Navigating real estate 16:50 Polish Bar success 23:08 Transferring skills from previous industries 34:19 Navigating real estate and running a business 40:48 Building confidence through successful selling 50:00 Personal branding through authenticity  1:00:00 Power of partnership 1:11:00 Tips for entrepreneurs  Check out episode 494 of Side Hustle Pro podcast out now on Apple Podcasts, Spotify, and YouTube Links mentioned in this episode Tricia’s Website: https://serhant.com/agents/tricia-lee-riley Tricia’s Instagram: https://www.instagram.com/lovetricialee/?hl=en Team Tricia Lee: https://serhant.com/agents/tricia-lee-riley Bed-Stuy Restoration: https://www.restorationplaza.org/  Click here to subscribe via RSS feed (non-iTunes feed): http://sidehustlepro.libsyn.com/rss AnnouncementsJoin 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 Hosted on Acast. See acast.com/privacy for more information.

    1h 17m
  3. 493: How To Make Content For Your Business In Less Than 1 Hour A Week

    19/12/2025

    493: How To Make Content For Your Business In Less Than 1 Hour A Week

    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 YouTube Links mentioned in this episode Free Side Hustle Guide: https://www.sidehustlepro.co/startyourhustle/Register for my next FREE Podcast Masterclass: https://www.podcastmoguls.com/Favorite Ring Light: https://amzn.to/3KaMiGNNicaila’s Instagram: https://www.instagram.com/sidehustlepro/Content Tools Amazon List: https://www.amazon.com/shop/influencer-37ba1da3/list/WQ7ES8GSRRBH?ref_=cm_sw_r_cp_ud_aipsflist_aipsfinfluencer-37ba1da3_P22F9MBGA63FZKWR7V1WClick 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 Side Hustle Pro – @sidehustlepro #SideHustlePro Hosted on Acast. See acast.com/privacy for more information.

    22 min
  4. 492: Rebuilding My Business After Burnout

    11/12/2025

    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 MEInstagram:https://www.instagram.com/sidehustlepro Podcast: Side Hustle Pro Business inquiries: hi@sidehustlepro.co CHAPTERS00:00 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.

    17 min
  5. 491: 9 Side Hustles You Can Start Today That Could Replace Your 9-5

    04/12/2025

    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 9-5The side hustles former guests of Side Hustle Pro have had major success withWhy closing the gap between your ideas and actually starting is the key to your business Highlights include: 01:45 Cleaning services06:22 Faceless podcast07:57 Virtual assistant12:16 Social media marketing15:25 Short-form video editor 21:15 Podcast/YouTube channel manager22:30 AI integration specialist26:34 Corporate training and coaching29:40 Done-for-you service provider32:30 Why you should start now Check out episode 491 of Side Hustle Pro podcast out now on Apple Podcasts, Spotify, and YouTube Links mentioned in this episode Schedule a clarity call with Nicaila: https://buy.stripe.com/5kQ8wQegpaMW8YR72ZgrS0bJhanilka’s Cleaning Business Episode: https://www.youtube.com/watch?v=KuN8j7YEDFg Kimberly’s Corporate Training Episode: https://www.youtube.com/watch?v=A672riddr1E Nicaila’s Instagram: https://www.instagram.com/sidehustlepro/ Nicaila’s LinkedIn: https://www.linkedin.com/in/nicailamatthewsokome  Click here to subscribe via RSS feed (non-iTunes feed): http://sidehustlepro.libsyn.com/rss AnnouncementsJoin 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 InfoSide Hustle Pro – @sidehustlepro #SideHustlePro Hosted on Acast. See acast.com/privacy for more information.

    35 min
  6. 490: She Left Corporate and Built a 7-Figure Business

    26/11/2025

    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 AmericaHow she and her sister built ISee Technologies into a 7-figure consulting firmWhy public speaking became a core revenue driver in her businessHow personal healing shaped her approach to leadership and entrepreneurshipHer framework for helping organizations and individuals thrive without burning out Highlights Include00:00: 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 ISee Technologies: https://www.iseetechinc.com/Achieve Work Life Alignment by Dr. Lakila Bowden http://www.lakilabowden.com/  Click here to subscribe via RSS feed (non-iTunes feed): http://sidehustlepro.libsyn.com/rss Guest Social Media InfoLakila'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.

    55 min
  7. 489: How to Start a Side Hustle with AI (feat. Nadeen Matthews Blair)

    19/11/2025

    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 entrepreneurshipWhy early consulting and workshop opportunities found her before she officially launchedHow AI tools like Perplexity, Gamma, Looka, and Namelix helped her build her brand, website, and business foundation fastWhy AI is the most powerful leverage tool for side hustlers in 2025How redefining success around flexibility, family, and purpose shaped her new chapterWhat 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 InfoSide 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.

    58 min
  8. 488: The Power in the Pivot: How Keewa Nurullah Is Rebuilding After Closing Her Dream Business

    12/11/2025

    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 boundariesThe realities of pivoting after successHow she’s creating new pathways for community-minded entrepreneurs Highlights Include00:00 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 Keewa Nurullah Instagram:@kiwimercuryKeewa’s website: https://www.keewanurullah.com/Side Hustle Pro: https://sidehustlepro.co Click here to subscribe via RSS feed (non-iTunes feed): http://sidehustlepro.libsyn.com/rss AnnouncementsJoin 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 InfoInstagram: @kiwimercury Hosted on Acast. See acast.com/privacy for more information.

    52 min
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About

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.

Information

  • Creator
    Nicaila Matthews Okome | Side Hustle Pro Media
  • Years Active
    2016 - 2025
  • Episodes
    503
  • Rating
    Explicit
  • Copyright
    © 2025 SIDE HUSTLE PRO
  • Show Website
    Side Hustle Pro

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