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Side Hustle Pro

Nicaila Matthews Okome | Side Hustle Pro Media
Side Hustle Pro
Latest episode

506 episodes

  • Side Hustle Pro

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

    2026/1/22 | 22 mins.
    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 build
    The mindset shift that turns your paycheck into startup capital
    How to choose a side hustle that fits your real life, energy, and capacity
    How to decide in advance what “ready to leave” really looks like backed by numbers and a plan

    Highlights Include
    00:00 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 Episode
    Side Hustle Pro Website: https://sidehustlepro.co/
    Goal Getter Action Plan: https://side-hustle-pro.teachable.com/p/goal-getter-action-plan
    Watch & Listen
    Watch this episode on YouTube and listen on all podcast platforms:
    Apple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323
    Spotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8t
    YouTube: https://www.youtube.com/sidehustlepro
    Hosted on Acast. See acast.com/privacy for more information.
  • Side Hustle Pro

    497: 7 Side Hustles That Can Make Real Money

    2026/1/15 | 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 choosing a side hustle: don’t try everything at once, and focus on solving real problems
    Seven proven, service-based side hustle ideas — from home operations and career pivots to podcast booking and fractional COO work
    How to move from idea to action by getting your first client through simple, focused next steps

    Highlights Include
    00:00 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 Episode
    Side Hustle Pro Website: https://sidehustlepro.co/

    Watch & Listen
    Watch this episode on YouTube and listen on all podcast platforms:
    Apple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323
    Spotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8t
    YouTube: https://www.youtube.com/sidehustlepro

    Hosted on Acast. See acast.com/privacy for more information.
  • Side Hustle Pro

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

    2026/1/09 | 21 mins.
    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 momentum
    How I choose just three goals per sprint with one clear focus per month
    The simple way I break monthly goals into realistic weekly tasks that actually get done
    Why daily five minute reviews and one weekly self accountability day keep my goals from drifting
    The recalculation rule that helps me keep going when life gets messy without guilt or quitting

    Highlights Include
    00:00 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 Episode
    Goalgetter Action Plan: https://sidehustlepro.co/goalgetter
    Side 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/id1126021323
    Spotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8t
    YouTube: https://www.youtube.com/sidehustlepro

    Hosted on Acast. See acast.com/privacy for more information.
  • Side Hustle Pro

    495: Breaking My Own Glass Ceiling

    2025/12/31 | 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:
    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 girl
    Steps to take to combat the fear and negative self-talk that often creep in
    What 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.
  • Side Hustle Pro

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

    2025/12/24 | 1h 17 mins.
    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 business
    How content creation has helped her close real estate deals
    How she has stayed true to herself and blocked out opinions, jobs, and people who don’t align with her goals
    And 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

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

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About 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.
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