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Side Hustle Pro

Side Hustle Pro

By: Nicaila Matthews Okome | Side Hustle Pro Media
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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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Episodes
  • 519: After 10 Million Downloads, Here’s What I Learned

    519: After 10 Million Downloads, Here’s What I Learned
    Jun 20 2026

    If this resonated with you, here are additional resources:


    ⭐ APPLY TO SHIFT: https://sidehustlepro.co/shift


    When I launched Side Hustle Pro, I thought success would be measured by downloads, rankings, sponsorships, and audience growth. And while reaching 10 million downloads is a milestone I'm incredibly grateful for, I've learned that the true value of podcasting has very little to do with the number itself.


    In this episode, I share the biggest lessons I've learned after more than 500 episodes and 10 million downloads. From building meaningful relationships and creating opportunities I never could have predicted to developing new business offers, growing a loyal community, and gaining clarity on my next chapter, podcasting became much more than a content platform. It became a vehicle for transformation.


    Whether you're a podcaster, entrepreneur, creator, or professional looking to build your personal brand, this episode will challenge you to think differently about what you're creating and how it can become the bridge to where you want to go next.


    Main Takeaways
    • Downloads are not the destination. Trust, relationships, and opportunity are the true assets.
    • A podcast can become a powerful networking tool that opens doors you never expected.
    • Specificity and niching down accelerate discoverability, growth, and community building.
    • Podcasting can help you validate ideas, package your expertise, and build your next business offer


    Highlights Include
    • 00:00 – The lesson behind 10 million podcast downloads
    • 01:16 – Why podcasting became my most powerful networking tool
    • 03:28 – The new podcasting playbook for creators and entrepreneurs
    • 04:17 – Building trust through the intimacy of audio
    • 05:39 – My thoughts on video podcasting and discoverability
    • 10:34 – Why niche podcasts grow faster than general ones
    • 14:50 – Trust as the most valuable asset you build
    • 16:27 – How Side Hustle Pro led to national media opportunities
    • 18:30 – The unexpected doors podcasting opened for my career
    • 20:04 – Why most podcasts struggle to grow
    • 21:36 – How podcasting became the bridge to my next chapter
    • 23:52 – Why I created the Shift Program

    Links Mentioned in This Episode
    • Shift Program: https://sidehustlepro.co/shift


    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

    Announcements

    Applications are now open for Shift, my 12-week coaching program designed to help experienced professionals package their expertise into a profitable offer, identify their first clients, and confidently launch their next chapter.

    Learn more and apply at: https://sidehustlepro.co/shift


    Social Media

    Instagram: @sidehustlepro

    Hosted on Acast. See acast.com/privacy for more information.
    Show More Show Less
    26 mins
  • 518: The ONE skill you need to learn before you QUIT

    518: The ONE skill you need to learn before you QUIT
    Jun 12 2026
    If this resonated with you, here are additional resources: ⭐ APPLY TO SHIFT: https://sidehustlepro.co/shiftIn this solo episode, I am getting real with you about the one skill that changed everything for me and that I believe every woman needs to develop right now: learning how to make money directly for yourself. I am sharing why the leap from employee to entrepreneur is so hard, how our entire lives have programmed us to earn money for someone else, and what it truly takes to start creating money on your own terms.I take you back to my days at NPR, where I was climbing the ladder, playing the game, and quietly building Side Hustle Pro on the side. I share how a hater coworker who reported me to my boss became the catalyst for my exit plan, how I landed my first $4,000 podcast sponsorship from a cold customer service email, and how learning just two revenue streams gave me the confidence to leave my job for good.This episode is also a reminder that you do not have to have everything figured out before you start. Your first $20 or $25 outside of your paycheck changes something in you that no amount of planning can replicate. If you are sitting at a crossroads wondering what your next move is, this episode is your sign to start choosing yourself.Main TakeawaysThe difficulty of leaving a job is not fear or lack of risk tolerance; it is decades of programming to earn money for someone else, and that programming can be unlearned.Earning money depends on someone else choosing you, while creating money is about identifying a problem, building a solution, and offering it to the world.You do not need two revenue streams mastered before you act; your first dollar outside a paycheck unlocks a shift in confidence and mindset that no amount of planning can give you.Showing up imperfectly is part of the process; authenticity attracts the right people and gives your audience permission to let their guard down too.Highlights Include00:01 - Why I chose to record this episode on the go with ease over perfection02:27 - How jobs program us to earn money for someone else and why that makes the leap so hard03:06 - The story of bringing my now-husband Muoyo to my NPR holiday party and what it revealed about being stuck in the corporate mindset07:31 - Why smart, experienced, degreed women still feel stuck and what they are actually missing09:49 - The difference between earning money (someone choosing you) and creating money (creating value)12:15 - Why showing up imperfectly is how you attract your people, especially as Black women in professional spaces14:37 - Why relying on someone else to choose you is bad for your mental health, and what to do instead18:47 - My personal backstory: launching Side Hustle Pro while at NPR and investing $1,197 in a sponsorship intensive21:06 - How a cold email to a customer service inbox landed me my first $4,000 podcast sponsorship contract25:52 - The coworker who reported me to HR and how that moment became the push I needed to start my exit plan00:00 (Part 2) - Why your first $25 changes everything internally and how making money directly for yourself is the skill to build right nowLinks Mentioned in This EpisodeShift Coaching Program: sidehustlepro.co/shiftWatch & ListenListen to Side Hustle Pro on Apple Podcasts: podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323Listen on Spotify: open.spotify.com/show/13qDj08lBR4ymzGhXIKy8tAnnouncementsSHIFT, my transformational coaching program for ambitious women who want to turn their side hustle into their exit plan from their 9-to-5, is now open for applications. Apply now at sidehustlepro.co/shift before spots fill.Social MediaSide Hustle Pro Instagram: @SideHustlePro Hosted on Acast. See acast.com/privacy for more information.
    Show More Show Less
    30 mins
  • 517: After Quitting My 6-Figure Job to Launch My Own Business Here’s What I Learned

    517: After Quitting My 6-Figure Job to Launch My Own Business Here’s What I Learned
    Jun 5 2026

    If this resonated with you, here are additional resources:


    ⭐ APPLY TO SHIFT: https://sidehustlepro.co/shift


    In this solo episode, I'm pulling back the curtain on my entrepreneurial journey and sharing the six most important lessons I've learned since leaving my corporate job in 2017. Most people assume that quitting was my biggest risk, but the truth is, the scariest steps happened long before I ever turned in my notice.


    I take you all the way back to 2015, when I graduated from business school without a job after not receiving the full-time offer from my Google internship. From studying abroad in Barcelona to avoid reality, to moving back to DC and starting a blog with no plan, this episode is about what really happens in the messy middle before success shows up. I share how rejection led me to NPR, how my experience there became the foundation for Side Hustle Pro, and how I earned my first $4,000 sponsorship contract from a cold email to a customer service inbox.


    This episode is for anyone who is waiting for a sign, a plan, or the perfect moment. Spoiler: that moment is not coming. What is coming is everything you need to build, but only if you start. I break down exactly how I got here and what I want you to take away from this milestone journey.


    Main Takeaways
    • Rejection is redirection: Not getting the Google offer was the push that led Nicaila to build Side Hustle Pro.
    • You don't need the whole plan: Taking one next step, even without knowing where it leads, is how clarity is built.
    • Clarity comes from action: The idea for Side Hustle Pro did not come before the action; the action revealed the idea.
    • Bet on proof, not hope: Nicaila didn't quit her job out of fearlessness, she quit because she had consistent data showing her business could grow.


    Highlights Include
    • [00:02] I share the real biggest risk I took, and it wasn't quitting my job
    • [00:24] The Google internship story: expecting the full-time offer and not getting it
    • [02:45] Graduating from business school with no job, no plan, and moving back to DC
    • [04:40] Lesson 1: Rejection is redirection, and what that looked like in real life
    • [07:16] Lesson 2: You don't need the whole plan, just the next step
    • [00:02 segment 2] Lesson 3: Clarity comes from action, not waiting for an aha moment
    • [03:11] How Side Hustle Pro's concept was born out of a boring blog pivot
    • [07:26] Lesson 5: Bet on proof, how I earned my first $4,000 sponsorship
    • [11:37] The real reason I quit: not fearlessness, but evidence
    • [12:19] Lesson 6: The life you want is built before you leave, not after


    Links Mentioned in This Episode

    APPLY TO SHIFT: https://sidehustlepro.co/shift


    Watch & Listen

    Listen to Side Hustle Pro on Spotify: open.spotify.com/show/13qDj08lBR4ymzGhXIKy8t

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


    Social Media

    Instagram: @SideHustlePro


    Hosted on Acast. See acast.com/privacy for more information.
    Show More Show Less
    26 mins
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