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Side Hustle Pro

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Rating
★★★★★
4.7
from
1810 reviews
This podcast has
543 episodes
Language
English
Date created
2016/06/20
Latest episode
2026/10/23
Average duration
52 min.
Release period
8 days

Description

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.

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Why Everyone and Their Mother Has a Podcast
2026/10/23
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 TakeawaysA 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 showLinks Mentioned in This EpisodePodcast Moguls: https://sidehustlepro.co/podcastmogulsWatch & ListenSpotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8tApple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323AnnouncementsPodcast 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.
Life Update: How I'm Rebuilding My Business Around My Life
2026/10/16
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 TakeawaysDesign 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 IncludeWhy 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/4z2AZs8Watch & ListenSpotify: 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.
5 Simple Ways to Get Paid for What You Already Know
2026/09/30
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 nowWatch & 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 Plan Save your seat here. Social MediaSide Hustle Pro – @sidehustlepro #SideHustlePro Hosted on Acast. See acast.com/privacy for more information.
She Got Laid Off…Then Built a YouTube Income to Pay Her Bills
2026/09/25
This week in the guest chair, Symone’ Austin shares her powerful journey from being laid off to building a thriving YouTube platform. After recording and posting her layoff conversation, her video went viral and became the turning point in her entrepreneurial journey. In this episode, she breaks down how she built multiple income streams through YouTube ad revenue, brand partnerships, digital products, virtual assistant work, and strategic financial decisions like bringing on a roommate. If you’ve been navigating uncertainty, considering content creation, or wondering how to turn a setback into leverage, this episode will show you how. Highlights Include00:00 – Recording the layoff conversation that changed everything 04:30 – Growing from 10K to 60K+ subscribers in one year 08:20 – Making $5,900 in one month from YouTube ad revenue 13:00 – Cutting expenses and surviving without touching savings 18:10 – Turning skills into income: photography, digital products, VA work 24:00 – Why personal finance has one of the highest CPMs on YouTube 29:00 – Replacing a corporate salary through content creation 35:00 – The reality of working 7 days a week as a full-time creator 38:00 – Getting a roommate as a financial reset strategy 43:00 – Navigating job offers after deciding to go all-in Links Mentioned in This EpisodeWatch Symone’s YouTube video “I Got Laid Off From My 6 Figure Tech Job”Podcast Moguls: Start the Podcast That Builds Your Exit PlanRead Successful Failure by KevOnStageWatch & 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, attend my next live class: Start the Podcast That Builds Your Exit Plan. Save your seat here. Social MediaYouTube: Life and Numbers: https://www.youtube.com/lifeandnumbers Instagram: @lifeandnumbers: http://instagram.com/lifeandnumbers Side Hustle Pro – @sidehustlepro #SideHustlePro Hosted on Acast. See acast.com/privacy for more information.
From a Food Blog to a $500K-a-Year Media Business: How Jannese Torres Built Yo Quiero Dinero
2026/09/18
In this episode, I sat down with Jannese Torres, host of the Yo Quiero Dinero podcast, to talk about how she went from a corporate career in engineering, pharmaceuticals, and consumer manufacturing to building a $500K-a-year media business. Jannese shares how getting laid off pushed her to take entrepreneurship seriously and how her food blog, Delish D'Lites, became her first profitable side hustle. We talk about how she used her blog income to pay off her student loans, why she launched Yo Quiero Dinero in 2019 to create the personal finance show she wanted to hear as a Latina, and how the podcast became the engine behind her book, speaking engagements, brand partnerships, and other income streams. Jannese also breaks down the team and systems behind the business, why niching down helped her grow brand deals from $125 to more than $50,000, and how she separates the offers that pay the bills from the offers that let her experiment. This is an honest look at what it takes to build a profitable media brand without depending on one platform, one offer, or one source of income. In this episode, you will learn: How a layoff gave Jannese the push to test entrepreneurship before she felt fully readyWhy she treated her food blog like a non-negotiable commitment and learned SEO and brand partnershipsHow blog income helped her pay off her student loans and become debt-free in February 2020Why Yo Quiero Dinero centers Latinas and the power of building for a specific audienceHow the podcast became the foundation for her book, speaking, brand deals, and other revenue streamsWhy a podcast team, online business manager, and talent agent are essential to the way she works nowHow she separates reliable 'pay the bills' offers from 'fun money' offers that give her room to experimentHighlights Include01:07 - Being the first in her family to graduate from college and beginning her career in pharmaceuticals and medical devices 04:10 - How getting laid off became the catalyst for testing entrepreneurship 08:32 - Building the Delish D'Lites food blog and treating it like a non-negotiable commitment 09:52 - Learning SEO and brand partnerships through a food blogging course 11:33 - Using blog income to become debt-free in February 2020 16:32 - Why owning your platform matters more than building entirely on someone else's platform 17:32 - Moving from blogging to launching Yo Quiero Dinero in 2019 19:42 - Why the podcast intentionally centers the Latina community 26:01 - How the podcast became the engine behind her media business 36:51 - The team behind the business: a podcast team, an online business manager, and a talent agent 40:20 - Growing brand deals from $125 to more than $50,000 by niching down 48:07 - Managing cash flow with 'pay the bills' offers and 'fun money' offers Links and Resources MentionedYo Quiero Dinero: https://yoquierodineropodcast.com Connect With JanneseInstagram: @yoquierodineropodcast Hosted on Acast. See acast.com/privacy for more information.
How to Make Your First $1K Side Hustling
2026/09/11
If this resonated with you, here are additional resources: ⭐ APPLY TO SHIFT: https://sidehustlepro.co/shift You 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 perfection Highlights 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 offer Links 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/sidehustlepro Check out episode 530 of Side Hustle Pro podcast out now on Apple Podcasts, Spotify, and YouTube Click here to subscribe via RSS feed (non-iTunes feed): http://sidehustlepro.libsyn.com/rss Hosted on Acast. See acast.com/privacy for more information.
From YouTube Exec to Full-Time Creator: How Chanel Tyler Turned Content Creation Into 5-Figure Passive Income
2026/08/28
If this resonated with you, here are additional resources: ⭐ APPLY TO SHIFT: https://sidehustlepro.co/shift This 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 registrationSave 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/sidehustleproSocial MediaInstagram: @thecreatorprofitlab Instagram: @buymechanel Side Hustle Pro – @sidehustlepro #SideHustlePro Hosted on Acast. See acast.com/privacy for more information.
How Karen Young Built OUI the People
2026/08/21
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.
She Left Corporate Law, Went Back to Work, and Still Built a Global Fashion Brand
2026/08/14
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.
How Her Wine Became the Obama Presidential Center’s Official White Wine
2026/08/07
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.
7 Things I Had to Unlearn Before Leaving My Corporate Job
2026/07/31
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.
Why She Pulled Her Brand Out of Whole Foods After 26 Years | Dawn Fitch, Founder of Pooka Pure and Simple
2026/07/30
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.
How Roxy Couse Replaced Her Corporate Title With Her Personal Brand
2026/07/24
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.
She Emptied Her Retirement to Open a Tea Brand (Jamila Wright, Founder of Brookyn Tea)
2026/07/17
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.
How Real Housewives of Atlanta's Cynthia Bailey and Co-Founder Dana Hill-Robinson Built Glowissima Skincare
2026/07/14
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.

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Amarachi Mgbeke 2026/08/18
Deep Bow
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blinky02jd 2026/05/09
Authenticity is magic
I recently found the show. I love the real and honest conversations surrounding work, business, and life.
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A-Star8 2026/03/30
Very thoughtful and relatable content
Nicaila, thank you for your honesty and transparency in your podcast. Whenever I am able to stop and listen to your podcast, you always provide me wit...
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Really Really Really Rich 2026/03/21
Love this podcast
Side Hustle Pro is the best career, business and life advice show that is practical and actionable all delivered with Nicaila’s warm, encouraging and ...
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akey618 2026/02/20
So happy I found this podcast
I was down in the dumps about getting laid off am stumbled on this podcast. It was kismet. Nicaila’s advice on how brand yourself and take the skills ...
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FordTough213 2026/01/26
Thank You & Keep Going and Glowing
This has hands-down been one of my most favorite podcast. I have enjoyed listening since early 2025. I was not a big podcast listener before I found y...
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ashincredible 2026/01/15
Great for Women Entrepreneurs
Love this show, I’m always learning something from Nicaila and her guests.
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Delgado Creative Group 2025/11/19
Inspiring and actionable for every entrepreneru
Side Hustle Pro is a must-listen for anyone ready to turn their passion into a profitable business. Nicaila brings energy, authenticity, and practical...
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Love this podcast
I’m a white woman but absolutely love this podcast! It’s so inspirational and I look forward to each new episode.
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AngB! 2025/06/13
Monique R. Shields Ep 464 🔥
Literal Gems!! Monique is giving women of color permission to take up space! Love her podcast and SHP as well! Thank you both for these platforms!
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