Side Hustle Pro

Nicaila Matthews Okome | Side Hustle Pro Media
  • 4.7 (1.8K)
  • 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. 499: How to Make Your First $1K Side Hustling

    5D AGO

    499: How to Make Your First $1K Side Hustling

    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 clarity, confidence, and momentum. In This Episode, I Share: Why the first $1,000 changes everything mentally and strategicallyHow to choose a simple offer you can confidently deliver right nowHow to identify who your offer is really for and why frustration mattersWhy clarity, consistency, and conversations matter more than perfection Highlights Include: 00:00 – Why you don’t need a million dollars to change your life — you need your first $1,00001:35 – How your mindset shifts after you make your first $1K and why proof matters more than theory02:31 – What actually counts as an offer and why your first one should be useful, not fancy03:52 – Why starting with what you’re already confident in is the fastest way to get paid05:16 – How to decide who your offer is really for and why specificity matters07:27 – The difference between a painkiller and a vitamin offer (and why frustration drives sales)08:55 – How to package your offer simply without a website, logo, or brand11:22 – Why offering your service is the most important step people delay12:48 – How confidence and customer focus directly impact whether you make your first $1K14:04 – Why you don’t need a massive audience — just real conversations and feedback15:37 – How to use feedback as information instead of taking it personally17:47 – Why overbuilding and “perfecting” keeps side hustlers stuck19:21 – Breaking down the math behind $1,000 so it feels achievable20:45 – Why fewer clients at a higher price can reduce burnout21:34 – Why most people earn their first $1K from conversations, not content22:19 – How I made my first $1,000 and what actually worked26:03 – When to start building your email list and why simple free resources convert better28:54 – How to use a 12-week sprint to stay focused on your first $1K29:38 – What to do when your first offer feels slow or doesn’t land immediately31:08 – What changes after you hit your first $1,000 — and the mistake to avoid next31:49 – Final action steps to start building your first $1K offerLinks Mentioned in This EpisodeSide Hustle Pro Website: https://sidehustlepro.co/ Watch & ListenWatch this episode on YouTube and listen on all podcast platforms: Apple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323Spotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8tYouTube: https://www.youtube.com/sidehustlepro Hosted on Acast. See acast.com/privacy for more information.

    33 min
  2. 498: How to Start a Side Hustle Without Quitting Your Job

    JAN 22

    498: How to Start a Side Hustle Without Quitting Your Job

    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 first. I’m walking you through my five rules for side hustling the Side Hustle Pro way, plus a bonus rule to help you decide when you’re actually ready to leave your job on purpose, with a plan, and on your own terms. If you’ve been feeling the pull to build something but don’t want to move out of panic or pressure, this episode will help you build quietly, strategically, and stress-free. In This Episode, I Share: Why keeping your job can actually give you leverage and clarity as you buildThe mindset shift that turns your paycheck into startup capitalHow to choose a side hustle that fits your real life, energy, and capacityHow to decide in advance what “ready to leave” really looks like backed by numbers and a plan Highlights Include00:00 Introduction to Side Hustling 01:00 The Importance of Stability 02:24 Five Rules for Side Hustle Success 04:39 Rule 1: Keep Your Day Job 06:26 Rule 2: Choose a Suitable Side Hustle 08:53 Rule 3: Set Non-Negotiable Time Boundaries 12:37 Rule 4: Build Basic First 17:11 Rule 5: Protect Your Job While You Build 20:48 Bonus Rule: Decide What 'Ready to Leave' Means 24:01 Conclusion and Next Steps Links Mentioned in This EpisodeSide Hustle Pro Website: https://sidehustlepro.co/Goal Getter Action Plan: https://side-hustle-pro.teachable.com/p/goal-getter-action-planWatch & ListenWatch this episode on YouTube and listen on all podcast platforms: Apple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323Spotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8tYouTube: https://www.youtube.com/sidehustlepro Hosted on Acast. See acast.com/privacy for more information.

    23 min
  3. 497: 7 Side Hustles That Can Make Real Money

    JAN 15

    497: 7 Side Hustles That Can Make Real Money

    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 real problemsSeven proven, service-based side hustle ideas — from home operations and career pivots to podcast booking and fractional COO workHow to move from idea to action by getting your first client through simple, focused next steps Highlights Include00:00 Why your side hustle should be treated as leverage, not a hobby 02:10 The two rules to follow before choosing a side hustle 04:30 How to stop collecting ideas and start building a real business 06:30 Side Hustle #1: The local “fix-it” project manager (home ops manager) 10:15 Side Hustle #2: Career Pivot Studio for job seekers and career switchers 14:45 Side Hustle #3: Podcast guest booking agency for founders and experts 18:50 Side Hustle #4: Compliance, privacy, and admin cleanup for small businesses 22:30 Side Hustle #5: Elder care concierge for busy adult children 26:30 Side Hustle #6: Micro-business events producer for pop-ups and workshops 30:00 Side Hustle #7: Fractional COO and operations command center builder 35:20 How to pick one side hustle and take action this week 38:10 Simple next steps to land your first client Links Mentioned in This EpisodeSide Hustle Pro Website: https://sidehustlepro.co/ Watch & ListenWatch this episode on YouTube and listen on all podcast platforms: Apple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323Spotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8tYouTube: https://www.youtube.com/sidehustlepro Hosted on Acast. See acast.com/privacy for more information.

    28 min
  4. 496: The 12-Week Sprint Approach That Changed My Side Hustle Results

    JAN 9

    496: The 12-Week Sprint Approach That Changed My Side Hustle Results

    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 your goals quietly drift away by February, this episode gives you a simple and realistic framework you can start using right now. In This Episode, I Share: Why yearly goal setting gives side hustlers too much room to procrastinate and how 12 week sprints create clarity and momentumHow I choose just three goals per sprint with one clear focus per monthThe simple way I break monthly goals into realistic weekly tasks that actually get doneWhy daily five minute reviews and one weekly self accountability day keep my goals from driftingThe recalculation rule that helps me keep going when life gets messy without guilt or quitting Highlights Include00:00 Why annual goals do not work for busy side hustlers 02:50 How 12 week sprints eliminate procrastination 05:55 The rule of only three goals with one focus per month 10:20 Why writing my goals down is non negotiable 12:40 How I break goals into simple weekly tasks 14:45 The recalculation rule that keeps me moving forward 17:00 Choosing a weekly self accountability day 21:00 Your 12 week sprint challenge Links Mentioned in This EpisodeGoalgetter Action Plan: https://sidehustlepro.co/goalgetterSide Hustle Pro Website: https://sidehustlepro.co/ Watch this episode on YouTube and listen on all podcast platforms: Apple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323Spotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8tYouTube: https://www.youtube.com/sidehustlepro Hosted on Acast. See acast.com/privacy for more information.

    22 min
  5. 495: Breaking My Own Glass Ceiling

    12/31/2025

    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
  6. 494: Owning Manhattan’s Tricia Lee: From Beauty Mogul to Real Estate Titan

    12/24/2025

    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
  7. 493: How To Make Content For Your Business In Less Than 1 Hour A Week

    12/19/2025

    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
  8. 492: Rebuilding My Business After Burnout

    12/11/2025

    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 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
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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 - 2026
  • Episodes
    507
  • Rating
    Explicit
  • Copyright
    © 2025 SIDE HUSTLE PRO
  • Show Website
    Side Hustle Pro

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