Side Hustle Pro

Nicaila Matthews Okome | Side Hustle Pro Media
  • 0.0 (0)
  • 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. 12 hr ago

    How Karen Young Built OUI the People

    In this episode, I sat down with Karen Young, founder of OUI the People, a fine fragrance and body care brand born out of her own struggle with razor burn and ingrown hairs. Karen walks us through her path from fashion, where she interned at Dolce and Gabbana, to becoming an executive at Estee Lauder, to eventually building a beauty brand now sold in Sephora. But Karen's story starts before OUI the People, with a lifestyle and home goods brand called Hammocks and High T that she built and ultimately had to close. We talk about the hard lessons on margins and capital that came out of that experience, the unexpected subway encounter that led to her job at Estee Lauder, and how she used her years inside a major beauty conglomerate to build her own brand from the ground up. Karen also gets honest about the financial rollercoaster of raising venture capital, scaling a team, and chasing growth without profitability for years, and what finally shifted this year. We close things out with her thoughts on consumer psychology, pricing a premium product, and her advice for women weighing whether to leave a steady paycheck for their side hustle. Main TakeawaysWhy closing a business is not failure, but tuition in a school of hard knocks that teaches you margins, capital, and scale.How to price a premium product by studying who your customer already trusts enough to spend on, not just what they say they need.Why visibility does not equal revenue, and how chasing growth without watching profitability can quietly sink a business.How building a trusted circle of fellow founders can matter more than any book when the entrepreneurial journey gets lonely. Highlights Include00:20 - How a lifelong struggle with razor burn and ingrown hairs on melanated skin became the idea behind OUI the People05:49 - Why Karen closed her first business, a lifestyle and home goods brand called Hammocks and High T11:19 - Learning the difference between spotting a market gap and finding real money inside of it16:00 - The subway encounter that led to Karen's job offer at Estee Lauder25:37 - What Karen absorbed from watching a major beauty conglomerate acquire and scale brands from the inside34:15 - The origins of OUI the People, which started as a direct to consumer razor brand called We Shave41:14 - How Karen priced her first razor at seventy five dollars, then raised it to eighty five to ninety, by studying who was already buying La Mer43:49 - Why Karen called manufacturers in the UK, Germany, and Japan before choosing a small German razor maker50:39 - How the brand expanded from razors into body care, then into Sephora in 2019, then a full fragrance launch in 202357:57 - The honest truth about raising venture capital, scaling a team, and finally hitting profitability this year1:12:19 - Lightning round: her go to founder resource, the mentor she admires, her non negotiable evening ritual, and her advice for side hustlersLinks Mentioned in This EpisodeShop OUI the People: ouithepeople.com Social Mediaouithepeople.comOUI the People on Instagram: @ouithepeople https://www.instagram.com/ouithepeople/ OUI The People TikTok: @ouithepeople  https://www.tiktok.com/@ouithepeople  Hosted on Acast. See acast.com/privacy for more information.

    How Karen Young Built OUI the People

  2. 14 Aug

    She Left Corporate Law, Went Back to Work, and Still Built a Global Fashion Brand

    In this episode, I sat down with Busayo Olupona, founder and creative director of Busayo, the Brooklyn- and Lagos-based fashion brand known for its bold prints and textiles created with artisans in Nigeria. Busayo shares how she went from corporate finance law to bringing handmade pieces home in suitcases, selling them at scrappy pop-ups, and eventually landing in major retailers including Saks Fifth Avenue, Bloomingdale's, Shopbop, and Moda Operandi. But this conversation goes much deeper than fashion. Busayo opens up about returning to a 9-to-5 after years of entrepreneurship, the shame and fear she had to unlearn, and the two serious cardiac events that forced her to confront the cost of constant striving. We talk about what it takes to build a business without losing yourself, why preparation matters before opportunity arrives, and how faith, meditation, and surrender changed the way she leads. In This Episode, You Will LearnWhy learning a new industry while you still have a paycheck can protect both your savings and your confidenceHow to view returning to a job as reinvesting in your business, not failing at entrepreneurshipWhy Busayo had to separate her worth from her corporate title and other people's opinionsHow years of creating collections before buyers said yes prepared her for the Saks opportunityWhat two serious cardiac events taught her about sleep, stress, self-care, and sustainable ambitionHow wholesale relationships can drive recurring revenue, brand discovery, and direct-to-consumer salesWhy Busayo believes faith, meditation, and surrender are practical tools for entrepreneurship Highlights Include03:04 - Moving from Nigeria to the United States at age 11 and learning to reject parts of herself to fit in16:44 - How annual trips to Nigeria planted the seed for the Busayo brand19:37 - The first pop-up that pushed her to stop hiding her designs24:05 - Leaving Cleary Gottlieb and unlearning the belief that she was not enough29:16 - Attending her first trade show and returning with only two orders31:36 - Meeting mentor Mercedes Gonzalez and learning how wholesale really works32:36 - Going back to a legal job after burning through her savings34:49 - Returning to the same office building and confronting the shame tied to her old title36:19 - The first cardiac emergency that showed her she was pushing too hard39:49 - Experiencing a second cardiac event and making sleep and self-care non-negotiable47:59 - Why she now sees building a business as a spiritual endeavor55:49 - How years of preparation helped her seize the opportunity that led to Saks1:00:08 - Navigating strong years, lean years, and the impact of the Saks bankruptcy1:06:17 - Why wholesale remains an important revenue and discovery channel1:14:48 - Identifying your fear pockets before leaving a steady paycheck Links and Resources MentionedShop BusayoThe Fashion Designer Survival Guide by Mary GehlharRAISEfashionThe Untethered Soul by Michael A. SingerMindset by Carol S. Dweck Connect With BusayoBrand Instagram: @busayoworld: https://www.instagram.com/busayoworld/Personal Instagram: @busayojournal: https://www.instagram.com/busayojournal/ Hosted on Acast. See acast.com/privacy for more information.

    She Left Corporate Law, Went Back to Work, and Still Built a Global Fashion Brand

  3. 7 Aug

    How Her Wine Became the Obama Presidential Center’s Official White Wine

    After a devastating flood forced Chrishon Lampley to close her Chicago art gallery and wine bar, she turned that loss into the foundation for Love Cork Screw, a nationally distributed wine brand that has sold more than two million bottles. In this episode, Chrishon shares how she broke into the wine industry with no upfront capital, got her products into major retailers, and navigated the realities of building a consumer brand without millions in marketing dollars. She also reveals how a wine created in honor of her late father became the official white wine of the Obama Presidential Center, and what it took to rebuild after nearly losing the business again. Main TakeawaysA devastating setback, like losing a business to a flood, can become the foundation for something bigger if you keep moving forward.Building relationships and repeatedly asking for the sale, even after rejection, can open doors that money alone cannot.Chasing notoriety across too many markets at once can cost more than it earns; focusing on one market at a time builds real traction.Consistent, face to camera content can rebuild a business faster than relying on a marketing budget alone. Highlights Include[00:32] The flood that closed Three P's Art Lounge and led to Love Corkscrew[01:26] Becoming one of the first African American women with an on and off premise liquor license in downtown Chicago[05:58] Starting the Love Corkscrew blog as a way to heal after losing the gallery[11:14] Explaining what a negociant is and pioneering the term in the wine industry[17:30] Building Love Corkscrew from nothing through commission and consignment deals[24:41] The advice from Barefoot Wine's founders that changed her strategy[32:07] Losing her father and creating the Lampley wine line in his honor[35:00] Landing the deal to become the official white wine of the Obama Presidential Center[39:30] Running the Clink and Sip Festival and the Sipping Empower Foundation[44:29] Committing to daily social media consistency to rebuild the business in 2026 Links Mentioned in This Episodelovecorkscrew.comthelampley.com Watch & ListenSpotify: open.spotify.com/show/13qDj08lBR4ymzGhXIKy8tApple Podcasts: podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323 Social MediaInstagram: @lovecorkscrew Hosted on Acast. See acast.com/privacy for more information.

    How Her Wine Became the Obama Presidential Center’s Official White Wine

  4. 31 Jul

    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

  5. 30 Jul

    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

  6. 24 Jul

    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

  7. 17 Jul

    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)

  8. 14 Jul

    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
See All (536)

Hosts & Guests

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
    536
  • Rating
    Clean
  • Copyright
    © 2026 SIDE HUSTLE PRO
  • Show Website
    Side Hustle Pro

You Might Also Like