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Side Hustle Pro

Side Hustle Pro

Nicaila Matthews Okome | Side Hustle Pro Media

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!


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560 - You Could Get Paid for That: 5 Side Hustles You Can Start Right Now
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  • 560 - You Could Get Paid for That: 5 Side Hustles You Can Start Right Now

    Extra income does not have to mean a whole new life. In this solo episode, I walk through five side hustles people are doing right now, each one simple enough that you can picture the customer, the work, and why someone would pay for it.


    We cover flipping items from Facebook Marketplace and offering pickup or delivery, online resale on sites like Poshmark, a resale concierge service for people who want their things sold without the hassle, junk and donation hauling, and setting up one AI workflow for one type of small business. I also share where I have paid for similar services myself, including an after-hours AI assistant at my dentist's office.


    To close, I break down how to choose the idea that fits your time, money, storage, and transportation, how to find your first customers, and the four-step plan I would follow in the first month.


    Main Takeaways

    Pick categories you already know when flipping, and check that the margin covers your time and transport.Selling on someone else's behalf requires permission, platform rules, and a clear agreement on the split.Hauling needs a plan for items donation centers will not accept, plus the right vehicle and insurance.For AI services, master one workflow for one business type before offering anything broader.

    Highlights Include

    [00:03]Why these ideas are built for extra income, not a new life[01:54]Idea 1: Flipping Facebook Marketplace finds[04:13]Why a $20 item is not automatically a deal[06:44]Adding a Marketplace pickup and delivery service[07:31]Idea 2: Online resale on Poshmark and similar sites[09:53]Idea 3: Positioning a resale concierge service and building a site with Lovable[13:26]Idea 4: Junk and donation hauling[15:32]What to do when a donation center says no[16:15]Idea 5: Setting up one AI workflow for one small business[18:29]What I learned from my dentist's after-hours AI assistant[23:09]How to choose the idea that fits your time, money, and space[24:59]Finding customers and the first-month plan

    Links Mentioned in This Episode

    Lovable: https://lovable.dev


    Watch & Listen

    Spotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8tApple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323

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

    Tue, 03 Nov 2026 - 26min
  • 559 - Why Nobody Bought Your Offer (Even Though They Said They Would)

    People told you they would be the first to sign up. Then you launched, and they were nowhere to be found. In this solo episode, I break down why interest and buying are two different decisions, and what an underperforming launch can and can't tell you.


    I walk through the four signals to separate: what people praise, what they ask for, what they spend time with, and what they pay for. I also cover how to ask about past behavior instead of hypotheticals, how to figure out who actually saw your offer, and the five places a sale can break down: the audience, the problem, the offer, trust, and the invitation.


    Then I share what I do after a launch that misses my expectations, from talking to buyers and non-buyers to the webinar time test I'm running right now. I close with five questions to answer about the offer you've been sitting on so you can run your next small test.


    Main Takeaways

    Praise, requests, attention, and payment each answer a different question about your offer.Ask people about the last time they dealt with the problem, not whether they would buy.Measure who actually saw the offer before deciding nobody wants it.Change one or two things per launch so you know what made the difference.


    Highlights Include

    [00:00] When people say they'd buy it, then disappear at launch[02:20] Why your audience isn't necessarily lying to you[04:47] You and your customer are picturing two different offers[05:30] The four signals: praise, requests, attention, and payment[09:33] The meal planning example: asking about real experiences[11:54] What "I can't afford it" really means, and painkillers vs. vitamins[14:08] Start with the people who actually saw the offer[18:22] The five places a sale can break down[25:32] Did you actually ask people to buy?[30:33] Why a small paid pilot can teach you more than a big launch[34:00] What I do after a launch that misses my expectations[38:47] My webinar time test and changing one variable at a time[41:08] Setting a budget and a stopping point for your experiments[45:15] How my Instagram challenge became the Master the Gram course


    Watch & Listen

    Spotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8t

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

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

    Mon, 02 Nov 2026 - 45min
  • 558 - You Don’t Have to Be an Influencer to Build a Business

    You don't need a huge following or constant access to your private life to build a profitable business. You need to be known for solving a specific problem. In this solo episode, I break down the difference between influence and authority, and between visibility and exposure. I share the questions I ask clients before we talk about anything they don't want to do, starting with what they actually want to be known for. I walk through the three layers of sharing, how I decide what stays private, including how I've approached sharing my journey as an autism mom, and a simple boundary exercise you can use before you post. Then I cover four ways to build authority without becoming a lifestyle influencer: the teacher, the curator, the practitioner, and the connector. We close with how to pick one discovery channel and one owned channel, what consistency really looks like, and how to connect your content to a paid offer you can test.


    Highlights Include

    [00:00] Why a profitable brand doesn't require a huge following[01:40] The difference between an influencer and a business owner[02:20] Why my business keeps earning when I step away from Instagram[05:55] Being famous vs. being findable[08:15] The first question to answer: what do you actually want to be known for?[13:15] Visibility vs. exposure, and how I handle sharing my autism mom journey[18:00] The three layers of sharing: expertise, experience, and personal access[22:10] A boundary exercise and the question "What will this yield?"[26:15] The four ways to build authority: teacher, curator, practitioner, and connector[36:00] Discovery channels vs. owned channels, and why social media is rented attention[41:05] The three jobs every piece of business content should do[44:30] Why you should launch before you feel ready, even if you launch to crickets[49:30] Five questions to answer this week


    Links Mentioned in This Episode

    Podcast Moguls coaching program: https://sidehustlepro.co/podcastmoguls

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

    Tue, 27 Oct 2026 - 43min
  • 557 - Why Everyone and Their Mother Has a Podcast

    In this solo episode, I break down why so many people are starting shows right now, drawing on 10 years of running Side Hustle Pro, which I launched in 2016 and have grown past 10 million downloads.


    I walk through three things a podcast can be: a networking tool, a bridge from where you've been to where you want to go, and a launch pad. I share how I grew the show with a small paid promotion budget, landed my first $4,000 sponsorship while working full time at NPR, and was found by producers from the Today Show and TEDx without pitching.


    I also cover how I started Side Hustle Pro after graduating from business school without a job, how Ryan Clark used his podcast The Pivot to move into his next chapter, and how to give people a clear reason to listen so your show can grow and earn.

    Main Takeaways

    A podcast is a networking tool that opens doors a cold coffee request would not.Your show can be a bridge to the field you want next, even before you know what it is.Specificity grows a show; "life and everything in between" gives no one a reason to listen.Start before you need it: a podcast can work as your work insurance plan.

    Highlights Include

    [00:00] What Michelle Obama, Jalen Brunson, LeBron James, and I have in common[02:03] Why podcasting is the most powerful networking tool[04:40] Podcasting from home as an introvert[06:55] Podcasting as a bridge to where you want to go[12:05] How I grew Side Hustle Pro with $5 to $10 per post in paid promotion[15:00] Landing my first $4,000 sponsorship[18:50] Using your podcast as a pivot tool[22:50] How Side Hustle Pro started after business school[26:30] How the show led to the Today Show and TEDx[27:25] Ryan Clark, The Pivot, and your work insurance plan[29:45] Why "life and everything in between" won't grow your show

    Links Mentioned in This Episode

    Podcast Moguls: https://sidehustlepro.co/podcastmoguls

    Watch & Listen

    Spotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8tApple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323

    Announcements

    Podcast Moguls, my coaching program for podcasters, is open. If you want to start your own podcast or grow your current one, I'll coach you on making your show more visible, more marketable, and an actual business. Join at sidehustlepro.co/podcastmoguls.

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

    Fri, 23 Oct 2026 - 33min
  • 556 - Life Update: How I'm Rebuilding My Business Around My Life

    I kept putting off this solo episode because I did not want to get camera-ready. So I took the camera out of the picture. This audio-only life update is about the changes that helped me feel like myself again, a year after sharing that I was burned out.


    I share how I started building my business around my life as a mother, why I am focused on Podcast Moguls and SHIFT, and what I learned from launching the first group cohort of SHIFT this summer.


    I also talk about returning to therapy, the impact of postpartum on my mental health, and making room to rest. Next up: building systems that require less of my energy and asking what I can take out of the picture when I feel stuck.


    Main Takeaways

    Design your business around your life instead of designing your life around your business.Identify the part of a process that is keeping you stuck, and ask whether you can remove it.Focus on the offers that fit your life, and build systems that reduce unnecessary work.Protecting rest and getting professional support can change how you work and how you feel.


    Highlights Include

    Why this episode is audio only and what I removed from the pictureWhere I was last year compared to where I am nowBuilding my business around motherhood, with most of my work on Tuesdays and ThursdaysDeciding what belongs in the business after a year of experimentingRecommitting to Podcast Moguls and keeping it currentLaunching the first group cohort of SHIFT in JulyWhy Podcast Moguls and SHIFT feel aligned with this seasonThe next chapter: systems, systems, systemsChanging my relationship with business and my sense of worthTherapy, postpartum, and getting support for my mental healthThe year I centered myself and redefining wealth


    Additional Links:

    FREE CLASS: Start the Podcast that Builds Your Exit Plan: https://sidehustlepro.lpages.co/your-first-1000-downloadsJoin Podcast Moguls: https://sidehustlepro.co/podcastmogulsApply for the SHIFT Coaching Waitlist: https://sidehustlepro.co/shiftSTART Your Next Chapter: A Woman's Guide to Taking the Leap with AI by Nadeen Matthews Blair: https://amzn.to/4z2AZs8

    Watch & Listen

    Spotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8t


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

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

    Fri, 16 Oct 2026 - 37min
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