Side Hustle Pro
Side Hustle Pro

Side Hustle Pro

Nicaila Matthews Okome | Side Hustle Pro Media

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Episodes

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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.

Recent Episodes

510: How I'm Rebuilding After A Hard Season (feat. Monique Shields)
APR 17, 2026
510: How I'm Rebuilding After A Hard Season (feat. Monique Shields)
In this episode, I’m joined again by Monique Shields, and this conversation felt like therapy, coaching, and truth-telling all in one. We went deep into something I’ve personally been navigating: what it actually looks like to move out of survival mode as a high-achieving woman, especially when life has been life-ing.We talked about the invisible weight many of us carry, from parenting to business to unexpected life challenges, and how that impacts the way we show up, make decisions, and even spend money. One of the biggest shifts for me? Realizing I wasn’t telling myself the full story about what I had been carrying and surviving.Monique breaks down how our mindset around scarcity, energy, and outsourcing can keep us stuck, and what it really means to “resource yourself” instead of just pushing through. If you’ve been feeling stuck, foggy, or like you’re doing everything but still not moving forward, this episode will hit home.Main TakeawaysYou’re not behind, you’re likely operating without acknowledging everything you’ve been carryingScarcity mindset after a hard season can quietly shape your decisions and keep you stuckYour energy, not just your time, is one of your most valuable assetsResourcing yourself (mentally, physically, strategically) is essential for growthHighlights Include00:00 – Reconnecting with Monique and what she’s been building02:30 – Why intimate spaces and coaching containers matter04:30 – Starting YouTube and breaking through creative burnout06:00 – The hidden impact of hard seasons on decision-making08:00 – Why you’re not telling yourself the full story10:00 – High-achievers and the trap of self-pressure12:30 – Why “feeling less overwhelmed” isn’t the right goal15:00 – Scarcity mindset after financial or life shocks18:00 – Why cost-first thinking keeps you stuck21:00 – The “delusional belief” successful people hold about their future27:00 – The real value of your time and energy33:30 – What actually changed after hiring support36:00 – Mental fog and why you don’t even realize you’re in it40:00 – Why stability is not the same as hoarding43:00 – What it really means to “resource yourself”46:00 – The importance of having multiple “brains” supporting you50:00 – Why your nervous system needs support in today’s world52:00 – Reframing “I can’t afford it” into a choiceLinks Mentioned in This EpisodeSave the Date: Start the Podcast That Builds Your Exit Plan (April 17)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/sidehustleproAnnouncementsIf you’re ready to build a podcast that becomes your exit plan from your 9-to-5, sign up for my next live class: Start the Podcast That Builds Your Exit PlanSave your seat here. Social MediaInstagram: @moniquershieldsPodcast: Ambition Without CompromiseSide Hustle Pro – @sidehustlepro#SideHustlePro Hosted on Acast. See acast.com/privacy for more information.
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49 MIN
509: Opening Up About My Journey as an Autism Mom
APR 10, 2026
509: Opening Up About My Journey as an Autism Mom
This episode is one of the most personal and vulnerable conversations I’ve ever shared. I’m opening up about my journey as an autism mom, from the early days of pregnancy and motherhood during the pandemic to navigating the realities of developmental delays, diagnoses, and advocacy. What started as subtle concerns about speech delays turned into a life-changing journey through early intervention, therapy, and eventually receiving an official autism diagnosis for my son. Along the way, I’ve had to learn how to advocate fiercely, navigate complex systems, and redefine what motherhood looks like for me and my family.This episode is about the hard moments, the emotional weight, and the unexpected beauty in this journey. It’s also about community, resilience, and learning to see strength in a path that looks different than what I once imagined.Highlights Include00:00 – Why this episode is deeply personal02:00 – Pregnancy, birth, and early milestones during the pandemic04:30 – First signs of speech delay and comparing developmental milestones06:30 – The emotional impact of early evaluations07:30 – Starting early intervention: speech and occupational therapy09:00 – Transition to specialized preschool and navigating the system11:00 – The hidden challenges of parenting a child with special needs12:30 – Communication barriers and emotional regulation as a parent14:00 – The moment I realized how much I’ve been carrying16:40 – Understanding gestalt language processing19:30 – Getting an official autism diagnosis21:00 – Advocating for my son within the school system23:30 – A “guardian angel” moment that changed everything27:00 – The role of faith in navigating this journey29:00 – Finding community and learning from other moms30:30 – Lessons autism has taught me about boundaries and perspective31:00 – A real-life parenting moment at the barbershop33:00 – Choosing celebration during Autism Awareness MonthLinks Mentioned in This Episode• Save the Date: Start the Podcast That Builds Your Exit Plan (Friday, April 17)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/sidehustleproAnnouncementsIf you’re ready to build a podcast that becomes your exit plan from your 9-to-5, sign up for my next live class: Start the Podcast That Builds Your Exit PlanSave your seat here. Social MediaSide Hustle Pro – @sidehustlepro#SideHustlePro Hosted on Acast. See acast.com/privacy for more information.
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32 MIN
508: The Tax Mistakes Side Hustlers Make That Cost Them Thousands (And How to Avoid Them)
APR 8, 2026
508: The Tax Mistakes Side Hustlers Make That Cost Them Thousands (And How to Avoid Them)
If you’re a side hustler or solopreneur, taxes can go from simple to overwhelming real fast and the truth is, many entrepreneurs are quietly losing thousands of dollars just by not knowing what they don’t know. In this episode, I sat down with CPA and TurboTax Expert Lisa Greene-Lewis to break down the most common tax mistakes side hustlers make, from choosing the wrong business structure too early to missing out on key deductions and failing to stay organized throughout the year. We also unpack what actually makes taxes more complex as your business grows and how to stay ahead of it before tax season hits.This conversation is all about helping you feel more confident, more prepared, and more in control of your finances. Because the goal is not just to make money in your business but to keep more of it.Main TakeawaysLack of consistent tracking is the biggest mistake that leads to overpaying taxesMany solopreneurs miss deductions simply because they are unaware of what qualifiesStaying organized year-round is the key to reducing stress and maximizing savingsHighlights Include00:00 – Introduction to tax season for solopreneurs02:00 – Lisa’s journey into tax expertise and entrepreneurship05:20 – LLC vs S corp: what you actually need to know08:20 – When taxes start to feel complicated09:30 – Why tracking income and expenses is critical11:40 – Common deductions people miss13:00 – Home office deduction explained14:20 – Section 179 and equipment write-offs15:10 – What you can’t deduct (clothes, hair, makeup)16:40 – Business credit card interest deduction17:20 – Employing your kids as a tax strategy18:00 – SEP IRA and retirement savings for entrepreneurs19:00 – Qualified Business Income deduction20:10 – Key tax law updates and 1099-K changes23:20 – How to stay organized with QuickBooks25:40 – How TurboTax experts support business owners27:10 – Lisa’s personal system for staying organized Links Mentioned in This EpisodeTurboTax: https://turbotax.com/business QuickBooks: https://quickbooks.intuit.comWatch & 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/sidehustleproAnnouncementsIf you’re ready to build a podcast that becomes your exit plan from your 9-to-5, sign up for my next live class: Start the Podcast That Builds Your Exit PlanSave your seat here. Social MediaLinkedIn: https://www.linkedin.com/in/lisa-greene-lewis-7721b815a Website: https://turbotax.com/business Side Hustle Pro – @sidehustlepro#SideHustlePro Hosted on Acast. See acast.com/privacy for more information.
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34 MIN
507: The Hidden Cost of Waiting Until You're Ready
MAR 27, 2026
507: The Hidden Cost of Waiting Until You're Ready
If you’ve been waiting for the perfect moment to finally start that thing you said you’d do this year, this episode is your wake-up call. Because the truth is, that moment isn’t coming.This week, I’m pulling back the curtain on a very real, very messy week in my life and sharing why I decided to hit record anyway. From sick kids to mental clutter to a house that is far from organized, I had every reason to wait. But instead, I leaned into a powerful reminder: progress doesn’t require perfection.In this episode, I walk you through the mindset shifts that have helped me move through overwhelm, take action with limited time and energy, and stop letting the idea of “feeling ready” delay my goals. Because sometimes the real work isn’t the task itself, it’s learning how to show up before everything feels aligned.Main TakeawaysWaiting for the perfect time will keep you stuck longer than just starting messyYou have to work with the time and energy you actually have, not what you wish you hadNaming what’s holding you back helps you move through it fasterThe real growth often comes from managing your mindset, not completing the taskHighlights Include00:00 – Why I recorded this episode despite not feeling ready02:10 – How “unexpected” life moments keep disrupting plans04:18 – Learning to work in chaos instead of waiting for order05:30 – Lowering the bar to get started06:10 – Work with the time you have, not the time you wish you had08:00 – Managing your energy to show up at your best10:15 – Why naming the problem helps you move forward11:43 – Recognizing the season you’re in and adjusting expectations14:00 – Are you truly blocked or just thrown off?16:12 – How accountability helped me launch Side Hustle Pro18:36 – Overcoming imposter syndrome in a career leap21:22 – The hidden cost of needing to “have it all together”23:21 – Why perfection delays your income and growth26:24 – Maybe the real goal is mastering your mindset29:19 – Adjusting expectations so you can move forwardLinks Mentioned in This EpisodeSave the Date: Start the Podcast That Builds Your Exit Plan (Friday, April 10th)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/sidehustleproAnnouncementsIf you’re ready to build a podcast that becomes your exit plan from your 9-to-5, sign up for my next live class: Start the Podcast That Builds Your Exit PlanSave your seat here. Social MediaSide Hustle Pro – @sidehustlepro#SideHustlePro Hosted on Acast. See acast.com/privacy for more information.
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28 MIN
506: 5 Simple Ways to Get Paid for What You Already Know
MAR 20, 2026
506: 5 Simple Ways to Get Paid for What You Already Know
One of the biggest misconceptions I see when it comes to making money is the belief that you need to start from scratch. A new certification, a brand new idea, or a completely different skill set. But the truth is, most of us already have everything we need. The real problem is not a lack of knowledge, it is not knowing how to package and position what we already know.In this episode, I break down five simple and practical ways to turn your existing skills, experiences, and knowledge into income. Whether you are in between roles, exploring a side hustle, or just trying to make extra money right now, this episode is your reminder that there is value in what you already bring to the table.I also walk through a key mindset shift. You do not need to be the top expert. You just need to be a few steps ahead of the person you are helping. People are not just paying for information. They are paying for clarity, speed, guidance, and confidence. And that is where your opportunity lies.Main TakeawaysYou do not need new skills or certifications to start making moneyThere are five core ways to monetize what you already knowPeople pay for clarity, speed, and guidance, not just expertiseStart with one path and keep it simple instead of trying everythingHighlights Include00:00 – The biggest misconception about making money01:30 – Why you already have valuable, monetizable knowledge02:00 – The 5 ways to make money with what you know03:00 – The mindset shift you need before starting04:00 – Service and coaching as the fastest path to income06:00 – Done-for-you services and why people pay for convenience08:00 – Creating simple digital products that sell10:30 – Workshops and why people pay for real-time learning13:00 – Why reminders are key when selling anything15:00 – Using content to create opportunities and income18:00 – How to use AI without losing your voice21:00 – Why you should pick ONE path and start nowLinks Mentioned in This EpisodeSave the Date: Start the Podcast That Builds Your Exit Plan (Friday, March 20)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/sidehustleproAnnouncementsIf you’re ready to build a podcast that becomes your exit plan from your 9-to-5, sign up for my next live class: Start the Podcast That Builds Your Exit PlanSave your seat here. Social MediaSide Hustle Pro – @sidehustlepro#SideHustlePro Hosted on Acast. See acast.com/privacy for more information.
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23 MIN