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Side Hustle Pro: Daily Summaries Delivered
by 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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- 2 days ago53 min
From a Food Blog to a $500K-a-Year Media Business: How Jannese Torres Built Yo Quiero Dinero
In this episode, I sat down with Jannese Torres, host of the Yo Quiero Dinero podcast, to talk about her path from a corporate career in pharmaceuticals and consumer manufacturing to building a multi-business income model. Jannese shares how getting laid off became the catalyst for testing entrepreneurship, and how a food blog called Delish Delights became her first profitable side hustle.We talk about how she used blog income to pay off her student loans, why she launched Yo Quiero Dinero in 2019 to fill a gap in the personal finance space for Latinas, and how the podcast became the engine behind her book, speaking engagements, and brand partnerships. Jannese also breaks down the team and systems running her business, from her podcast team to her online business manager and talent agent.We close with how she structures her revenue between bills offers and fun money offers, why niching down grew her brand deals from one hundred twenty five dollars to over fifty thousand dollars, and her advice for women considering leaving corporate to build something of their own.Main TakeawaysBuild multiple income systems rather than one offer, so no single platform or algorithm controls your revenue.Niche down to a hyper specific audience so brands can immediately understand your value and pay more for it.Outsource early: a podcast team, an online business manager, and a talent agent free up time to build.Split offers into bills offers that cover fixed costs and fun money offers that fund experimentation.Highlights Include01:07 - Jannese on being the first in her family to graduate college and her career in pharmaceuticals and medical devices04:10 - Getting laid off as the catalyst for testing entrepreneurship08:32 - Building the Delish Delights food blog and treating it like a non negotiable commitment09:52 - Learning SEO and brand partnerships through a food blogging course11:33 - Using blog income to become debt free in February 202016:32 - Why owning your platform matters more than building on Substack17:32 - Transitioning from blogging to launching Yo Quiero Dinero in 201919:42 - Addressing why the podcast centers the Latina community26:01 - How the podcast became the engine of her business36:51 - The team behind the business: a podcast team, an online business manager, and a talent agent40:20 - Growing brand deals from one hundred twenty five dollars to over fifty thousand dollars48:07 - Managing cash flow with bills offers and fun money offersLinks Mentioned in This Episodehttps://yoquierodineropodcast.comSocial MediaInstagram: @yoquierodineropodcast Hosted on Acast. See acast.com/privacy for more information.
- 1 weeks ago33 min
How to Make Your First $1K Side Hustling
If this resonated with you, here are additional resources:⭐ APPLY TO SHIFT: https://sidehustlepro.co/shiftYou do not need a million dollars to change your life, you need your first $1,000.In this solo episode, I’m breaking down why the first $1K is such a pivotal milestone for side hustlers and how it shifts everything from theory to proof. I walk you through the exact decisions and actions that turn preparation into income without overbuilding, overthinking, or waiting until things feel perfect.If you’ve been stuck planning, tweaking, or doubting yourself, this episode will help you move forward with clarity, confidence, and momentum.In This Episode, I Share:Why the first $1,000 changes everything mentally and strategicallyHow to choose a simple offer you can confidently deliver right nowHow to identify who your offer is really for and why frustration mattersWhy clarity, consistency, and conversations matter more than perfectionHighlights Include:00:00 – Why you don’t need a million dollars to change your life — you need your first $1,00001:35 – How your mindset shifts after you make your first $1K and why proof matters more than theory02:31 – What actually counts as an offer and why your first one should be useful, not fancy03:52 – Why starting with what you’re already confident in is the fastest way to get paid05:16 – How to decide who your offer is really for and why specificity matters07:27 – The difference between a painkiller and a vitamin offer (and why frustration drives sales)08:55 – How to package your offer simply without a website, logo, or brand11:22 – Why offering your service is the most important step people delay12:48 – How confidence and customer focus directly impact whether you make your first $1K14:04 – Why you don’t need a massive audience — just real conversations and feedback15:37 – How to use feedback as information instead of taking it personally17:47 – Why overbuilding and “perfecting” keeps side hustlers stuck19:21 – Breaking down the math behind $1,000 so it feels achievable20:45 – Why fewer clients at a higher price can reduce burnout21:34 – Why most people earn their first $1K from conversations, not content22:19 – How I made my first $1,000 and what actually worked26:03 – When to start building your email list and why simple free resources convert better28:54 – How to use a 12-week sprint to stay focused on your first $1K29:38 – What to do when your first offer feels slow or doesn’t land immediately31:08 – What changes after you hit your first $1,000 — and the mistake to avoid next31:49 – Final action steps to start building your first $1K offerLinks Mentioned in This EpisodeSide Hustle Pro Website: https://sidehustlepro.co/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/sidehustleproCheck out episode 530 of Side Hustle Pro podcast out now on Apple Podcasts, <a href="https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy
- 3 weeks ago1h 9m
From YouTube Exec to Full-Time Creator: How Chanel Tyler Turned Content Creation Into 5-Figure Passive Income
If this resonated with you, here are additional resources:⭐ APPLY TO SHIFT: https://sidehustlepro.co/shiftThis week in the guest chair is Chanel Tyler, a strategist, creator, and self-described “contentpreneur” who has worked across investment banking, luxury marketing, and YouTube before stepping fully into entrepreneurship.Chanel built her reputation online by sharing trusted product recommendations and insights from her background in beauty marketing. But after years of consulting with a creator commerce platform that generated over 80% of her income, everything changed when the company suddenly shut down.In this episode, Chanel opens up about what it really looks like to rebuild after losing the majority of your income overnight. She shares how she pivoted by diversifying her platforms, leaning deeper into affiliate marketing, launching new creator education programs, and embracing the vulnerability of sharing her personal story — including her journey with hearing loss.If you’ve ever worried about relying on a single income stream or wondered how creators actually make money online, Chanel breaks down the strategy behind building a sustainable creator business.In this episode, Chanel shares:How she built a creator business by combining corporate strategy, content creation, and affiliate marketingWhat happened when the platform responsible for 80% of her income shut down overnight and how she rebuiltWhy diversification across platforms, income streams, and partnerships is essential for creators and entrepreneursHow affiliate marketing works and how creators can use performance data to negotiate higher-paying brand dealsHighlights Include00:00 – Introduction02:10 – Chanel’s career path from investment banking to luxury beauty marketing05:10 – Building an audience through skincare and product recommendations09:00 – Landing a role at YouTube working with top creators15:00 – Saving a year of income before leaving corporate19:00 – The moment she lost 80% of her income overnight24:30 – Why diversification is critical for creators and entrepreneurs27:00 – Building content series that grow an audience32:00 – Affiliate marketing vs. brand partnerships explained37:00 – Sharing her journey with hearing loss and disability40:00 – How statement earrings became part of her empowerment story43:00 – Affiliate income strategies for creatorsLinks Mentioned in This EpisodeSubstack: SensibleJulia BroomeCheck out the Networth and Chill Podcast;Creator Economy & Brand Deals with Victoria ParisShopMy:https://shopmy.us/home/creatorsMagicLinks:https://www.magiclinks.com/creatorsBrandCycle:https://brandcycle.com/LTK: https://company.shopltk.com/en/creatorNordstrom Affiliate Program:https://www.nordstromcreators.com/Check out Chanel’s Creator Profit Lab’s interest form & course registration<a href="https
- Aug 21, 20261h 14m
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.comSocial 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.
- Aug 14, 20261h 11m
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 entrepreneurshipHighlights 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 paycheckLinks and Resources MentionedShop BusayoThe Fashion Designer Survival Guide by Mary GehlharRAISEfashionThe Untethered Soul by Michael A. SingerMindset by Carol S. DweckConnect 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.
- Aug 7, 202651 min
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 2026Links Mentioned in This Episodelovecorkscrew.comthelampley.comWatch & ListenSpotify: open.spotify.com/show/13qDj08lBR4ymzGhXIKy8tApple Podcasts: podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323Social MediaInstagram: @lovecorkscrew Hosted on Acast. See acast.com/privacy for more information.
- Jul 31, 202643 min
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/shiftIn 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 carryingWatch & ListenSpotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8tApple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323Social MediaInstagram: @SideHustlePro Hosted on Acast. See acast.com/privacy for more information.
- Jul 30, 202652 min
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/shiftIn 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 Dawn's start as a graphic designer in the music industry, designing album covers The moment paralysis first hit while she was walking to work The five-year journey to her eventual MS diagnosis How the name Pooka came from her mother calling her kids her pooka leaders Why email marketing became the backbone of the business from day one The cease-and-desist letter over the brand name right before entering Whole Foods How putting her pride to the side led to her first 10 Whole Foods stores Her advice on knowing when a business is truly ready for big box retail Why Pooka exited all 62 of its Whole Foods stores last year How the Best Life Tribe Facebook group and a sea moss request from a member helped save the business during the pandemic Landing the 250,000 dollar Audible DEI grant for the new Newark space How the Bloom Bar, almost an afterthought, became the biggest draw of the businessWatch & ListenSpotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8tApple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323Social MediaWebsite: pookapureandsimple.comInstagram: @PookalitaTikTok: @Pookalita1 Hosted on Acast. See acast.com/privacy for more information.
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About Side Hustle Pro
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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