Side Hustle Pro

Nicaila Matthews Okome | Side Hustle Pro Media
  • 4.9 (50)
  • 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. 13 hrs ago

    7 Things I Had to Unlearn Before Leaving My Corporate Job

    If this resonated with you, here are additional resources: ⭐ APPLY TO SHIFT: https://sidehustlepro.co/shift In this episode, I'm sharing the seven beliefs I had to unlearn before I could finally leave my corporate job and build Side Hustle Pro full time. I spent decades in corporate America, working at places like HBO, MTV, Google, and NPR, and even though I knew I wanted to leave, I wasn't mentally ready until I confronted the internal beliefs that kept me tied to that life. Highlights Include00:00 - My corporate background and why I'm scratching the record on old habits 03:01 - The seven things I had to unlearn to build Side Hustle Pro full time 06:48 - Unlearning the need to have my entire future figured out before leaving 11:25 - Why other people's opinions could not be my decision making system 17:31 - Unlearning that a job or promotion was my only path to more money 21:59 - Pay inequity in corporate and why the ceiling is lower than it seems 22:49 - Unlearning that I was limited to doing only what I had already done 27:33 - Confusing busyness with meaningful progress, and the one hour a day model 33:36 - The biggest unlearn: staying employed was not actually the safest option 42:21 - Reflection questions to figure out which belief you're still carrying Watch & ListenSpotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8t Apple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323 Social MediaInstagram: @SideHustlePro  Hosted on Acast. See acast.com/privacy for more information.

    7 Things I Had to Unlearn Before Leaving My Corporate Job

  2. 1d ago

    Why She Pulled Her Brand Out of Whole Foods After 26 Years | Dawn Fitch, Founder of Pooka Pure and Simple

    If this resonated with you, here are additional resources: ⭐ APPLY TO SHIFT: https://sidehustlepro.co/shift In this episode, I sat down with Dawn Fitch, founder of Pooka Pure and Simple, to talk about the winding road that took her from designing album covers in the music industry to building a natural beauty brand rooted in her own health journey. Dawn opens up about the years it took to get an MS diagnosis, and how healing herself led her to start formulating clean, simple products long before she ever thought of herself as a business owner. We get into the real, unglamorous parts of entrepreneurship: street teaming outside churches before social media existed, a cease-and-desist letter that almost derailed her Whole Foods deal, and the hard lessons of scaling into big box retail. Dawn also shares how she walked away from a failing retail lease with nowhere to go, only to land in the space that's been home to her production for over a decade. Finally, Dawn walks me through the newest chapter of her story: a 250,000 dollar grant from Audible's DEI program that brought Pooka into a beautiful new Newark location, and how an activity she almost treated as an afterthought, the Bloom Bar, became the biggest draw of the whole business. Main TakeawaysProtect your business structure early. Trademark your name, keep separate books, and build SOPs before you're forced to by a cease-and-desist letter or a big retail opportunity.Don't chase big box retail until your core revenue stream is stable enough to absorb the rules, returns, and thin margins that come with it.When a business decision doesn't feel right, it is okay to walk away even without a backup plan. Trust and timing can lead you somewhere better.Build a real activation or experience around your product. Community and connection, not just the product itself, is what keeps customers coming back. Highlights Include(00:41) Dawn's start as a graphic designer in the music industry, designing album covers(01:36) The moment paralysis first hit while she was walking to work(03:04) The five-year journey to her eventual MS diagnosis(05:15) How the name Pooka came from her mother calling her kids her pooka leaders(07:19) Why email marketing became the backbone of the business from day one(11:01) The cease-and-desist letter over the brand name right before entering Whole Foods(13:49) How putting her pride to the side led to her first 10 Whole Foods stores(18:29) Her advice on knowing when a business is truly ready for big box retail(26:51) Why Pooka exited all 62 of its Whole Foods stores last year(29:04) How the Best Life Tribe Facebook group and a sea moss request from a member helped save the business during the pandemic(32:07) Landing the 250,000 dollar Audible DEI grant for the new Newark space(35:14) How the Bloom Bar, almost an afterthought, became the biggest draw of the business Watch & ListenSpotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8t Apple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323 Social MediaWebsite: pookapureandsimple.com Instagram: @Pookalita TikTok: @Pookalita1 Hosted on Acast. See acast.com/privacy for more information.

    Why She Pulled Her Brand Out of Whole Foods After 26 Years | Dawn Fitch, Founder of Pooka Pure and Simple

  3. Jul 24

    How Roxy Couse Replaced Her Corporate Title With Her Personal Brand

    If this resonated with you, here are additional resources: ⭐ APPLY TO SHIFT: https://sidehustlepro.co/shift In this episode, I sat down with Roxy Couse, the creator behind Millennial Manager, to talk about how she built a thriving personal brand while climbing the corporate ladder. Roxy spent almost 15 years in corporate, working her way up to senior director, before stepping away to run her content and consulting business full time. We got into the real logistics of that transition, from going part time first, to navigating conflict of interest concerns at work, to eventually bringing on a management team once the opportunities became too much to handle alone. Roxy also opened up about paying off student loan debt with her side hustle income and the exact moment she realized her content could become a real business. Roxy is now building SlowFi, a platform designed to help other corporate professionals build profitable personal brands with structure, community, and coaching.  Main Takeaways: Consider going part time before fully leaving your job so you can test whether your side income is consistent before walking away completely.Protect your main income while building a passion project by staying discreet at work and avoiding brand partnerships that could create a conflict of interest.Bring on a management team or support staff once inbound opportunities outgrow what you can manage on your own, especially around contracts and negotiations.Personal brand building does not have to be high effort. Make content creation fit into the pockets of time you already have instead of forcing a rigid content calendar. Highlights Include1:01 - Roxy's 15 year corporate career and her shift into content creation3:50 - What held Roxy back from starting to create content6:36 - The origin story behind her Millennial Manager persona8:09 - How Roxy navigated conflict of interest concerns while working full time14:20 - Why she went part time before leaving corporate completely19:51 - The moment she realized she needed a management team25:26 - How her one on one consulting turned into building SlowFi33:24 - Her timeline for launching SlowFi and the realities of bootstrapping as a Black founder38:22 - Balancing motherhood with running her business47:00 - Lightning round: resources, admiration, non-negotiables, and her advice for aspiring side hustlers Watch & ListenSpotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8t Apple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323 Social MediaInstagram, TikTok, and X: @Roxycouse Hosted on Acast. See acast.com/privacy for more information.

    How Roxy Couse Replaced Her Corporate Title With Her Personal Brand

  4. Jul 17

    She Emptied Her Retirement to Open a Tea Brand (Jamila Wright, Founder of Brookyn Tea)

    If this resonated with you, here are additional resources:  APPLY TO SHIFT: https://sidehustlepro.co/shift In this episode, I sat down with Jamila Wright, co-founder of Brooklyn Tea, to trace the full story of how she and her husband Ali turned tea dates into a business. Jamila walked me through leaving a career in education, emptying her retirement savings, and fighting a two year trademark battle before they ever opened their first location. We got into the real financial decisions behind building out that first shop, including an SBA loan that arrived late, putting up her own home as collateral, and the lesson she learned about the difference between being an investor and being an owner operator. Jamila also shared how a relationship with a fellow Brooklyn business owner led to their current Lewis Avenue location. From there we picked up with how Brooklyn Tea’s verticals came together, the financial setbacks along the way including a six figure loan and a partnership that fell apart, and the moment she and Ali finally started paying themselves.  Main TakeawaysBig opportunities often come from saying yes rather than a master plan, so be ready to rise to the moment when it arrives.Waiting on outside funding like an SBA loan can force you to dip into personal savings, so plan for delays before signing a lease or starting construction.Choosing between taking on debt or equity investors should depend on your long term goal, whether that is building a legacy brand or eventually selling it.Paying yourself is a milestone that often comes after years of sacrifice, so figuring out that number is part of building a sustainable business.Highlights Include(00:32) How Jamila and Ali went from dating over tea to business partners(08:12) The financial decisions behind opening the first Brooklyn Tea location(16:16) Why Jamila had to put up her Atlanta home as collateral for their SBA loan(19:38) Debt versus equity, and deciding what kind of business you want to build(24:13) The real lesson foot traffic taught them about their first location(29:45) How a relationship with Monique Greenwood led to their current Lewis Avenue location(37:33) Saying yes to wholesale and e-commerce almost by accident(47:39) Landing a licensing and franchising deal with an airport(52:12) The Saks Fifth Avenue partnership that fell apart(1:07:45) Paying themselves for the first time after two and a half yearsWatch & ListenSpotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8t Apple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323 Social MediaWebsite: brooklyntea.com Brooklyn Tea Instagram: @brooklyntea Jamila's Instagram: @jamilawright21 Hosted on Acast. See acast.com/privacy for more information.

    She Emptied Her Retirement to Open a Tea Brand (Jamila Wright, Founder of Brookyn Tea)

  5. Jul 14

    How Real Housewives of Atlanta's Cynthia Bailey and Co-Founder Dana Hill-Robinson Built Glowissima Skincare

    If this resonated with you, here are additional resources: ⭐ APPLY TO SHIFT: https://sidehustlepro.co/shift In this episode, I sat down with longtime friends and business partners Cynthia Bailey and Dana Hill-Robinson to talk about how a friendship that started in a New York hair salon in the 1990s turned into a skincare brand thirty years later. Cynthia shares her path from an eighteen year old model moving to New York to a reality television mainstay, while Dana walks us through her years at Vogue and Harper's Bazaar and building the beauty subscription box Cocotique. We dig into how they finally partnered on Glowissima, why they chose to launch with only two hero products, and how they source ingredients like manuka honey and kiwi seed oil from New Zealand. Cynthia also opens up about the businesses she has closed in the past and what those experiences taught her about knowing when to walk away. Cynthia and Dana get candid about profitability timelines, the current shift in consumer spending, and why a huge social following does not automatically translate into sales. They close out with practical advice for women who want to start a business but are worried about money and failure. Main TakeawaysLaunch lean: start with one or two hero products instead of a full line so you can prove the concept before scaling.Know when to fold: it is a business skill, not a failure, to walk away from a venture once it stops making financial sense.Vet every partnership: joint ventures work best when both sides have a track record and clearly defined roles from the start.Followers are not buyers: a large social following does not guarantee sales, so keep testing your messaging and your audience. Highlights Include(00:19) How Cynthia and Dana met at a New York hair salon in the 1990s(02:37) Cynthia's move from Alabama to New York at eighteen to model(04:08) The Essence cover that became Cynthia's big break(05:24) The move from modeling into reality television(10:26) Lessons from closing the Bailey Wine Cellar and the Bailey Room(14:44) Dana on pivoting Cocotique into a health and wellness hub(17:56) The formulation story and meaning behind the name Glowissima(19:14) Turning a thirty-year friendship into a business partnership(27:01) Sourcing manuka honey and kiwi seed oil from New Zealand(38:57) Digging deeper on marketing when the economy shifts 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 AnnouncementsApplications 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 MediaCynthia Bailey: Instagram @CynthiaBailey Dana Hill-Robinson: Instagram @DanaHillRobinson Glowissima: Instagram, Facebook, and TikTok @Glowissima Cocotique: Facebook @CocoTique, TikTok @CocoTiqueBeautyBox Hosted on Acast. See acast.com/privacy for more information.

    How Real Housewives of Atlanta's Cynthia Bailey and Co-Founder Dana Hill-Robinson Built Glowissima Skincare

  6. Jul 7

    520: How Jotaka Eaddy Built a Movement of 44,000 Black Women Overnight

    If this resonated with you, here are additional resources: ⭐ APPLY TO SHIFT: https://sidehustlepro.co/shift In this episode, I sat down with Jotaka Eaddy, founder of Full Circle Strategies and Win With Black Women, for a conversation about power, purpose and resilience. We talked about her childhood in Johnsonville, South Carolina, a town of under 1,400 people that taught her the value of community long before she ever set foot in Washington, DC or Silicon Valley. Jotaka walked me through her path from student activist against the death penalty to senior advisor at the NAACP to becoming the first Black employee at a fintech startup in Silicon Valley. She opened up about the layoff that nearly broke her and the Oprah Winfrey clip that helped her reframe it as redirection rather than failure. We also talked about how Win With Black Women was born from a single late night email in 2020 that turned into a Zoom call with 44,000 women, and how that same community continues to organize today. Jotaka got vulnerable about losing her mother during the 2024 election season and what that grief has taught her about faith, resilience and asking for help. Main TakeawaysYour community can be your first investors. The people of Jotaka's hometown pooled money so she could attend a conference that changed the course of her life.A layoff is not always failure. It can be redirection toward something bigger than you could have planned for yourself.Movements are built in the quiet, consistent work that happens long before anyone is watching or celebrating.Black women hold real power at the ballot box and in daily acts of organizing, even while in survival mode. Highlights Include02:01 - Growing up in Johnsonville, South Carolina05:04 - The conference that changed her life11:46 - Learning to lead by carrying the bag15:17 - Making the leap into Silicon Valley19:08 - Getting laid off and finding strength in an Oprah Winfrey clip29:02 - The spark behind Win With Black Women35:40 - The night 44,000 women joined the call44:53 - How to show up when you are in survival mode48:05 - Opening up about losing her mother 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/sidehustleproAnnouncementsApplications 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 MediaJotaka Eaddy: Instagram: @JotakaEaddy Win With Black Women: Instagram: @WinWithBlackWomen Hosted on Acast. See acast.com/privacy for more information.

    520: How Jotaka Eaddy Built a Movement of 44,000 Black Women Overnight

  7. Jun 20

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

    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 TakeawaysDownloads 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 Include00:00 – The lesson behind 10 million podcast downloads01:16 – Why podcasting became my most powerful networking tool03:28 – The new podcasting playbook for creators and entrepreneurs04:17 – Building trust through the intimacy of audio05:39 – My thoughts on video podcasting and discoverability10:34 – Why niche podcasts grow faster than general ones14:50 – Trust as the most valuable asset you build16:27 – How Side Hustle Pro led to national media opportunities18:30 – The unexpected doors podcasting opened for my career20:04 – Why most podcasts struggle to grow21:36 – How podcasting became the bridge to my next chapter23:52 – Why I created the Shift ProgramLinks Mentioned in This EpisodeShift Program: https://sidehustlepro.co/shift 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/sidehustleproAnnouncementsApplications 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 MediaInstagram: @sidehustlepro Hosted on Acast. See acast.com/privacy for more information.

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

  8. Jun 12

    518: The ONE skill you need to learn before you QUIT

    If this resonated with you, here are additional resources: ⭐ APPLY TO SHIFT: https://sidehustlepro.co/shift In 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 now Links Mentioned in This EpisodeShift Coaching Program: sidehustlepro.co/shift Watch & ListenListen to Side Hustle Pro on Apple Podcasts: podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323 Listen on Spotify: open.spotify.com/show/13qDj08lBR4ymzGhXIKy8t AnnouncementsSHIFT, 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.

    518: The ONE skill you need to learn before you QUIT
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4.9
out of 5
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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
    533
  • Rating
    Clean
  • Copyright
    © 2026 SIDE HUSTLE PRO
  • Show Website
    Side Hustle Pro

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