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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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- 5 days ago49 min
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/shiftIn 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 hustlersWatch & ListenSpotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8tApple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323Social MediaInstagram, TikTok, and X: @Roxycouse Hosted on Acast. See acast.com/privacy for more information.
- 1 weeks ago1h 0m
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/shiftIn 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 How Jamila and Ali went from dating over tea to business partners The financial decisions behind opening the first Brooklyn Tea location Why Jamila had to put up her Atlanta home as collateral for their SBA loan Debt versus equity, and deciding what kind of business you want to build The real lesson foot traffic taught them about their first location How a relationship with Monique Greenwood led to their current Lewis Avenue location Saying yes to wholesale and e-commerce almost by accident Landing a licensing and franchising deal with an airport The Saks Fifth Avenue partnership that fell apart Paying themselves for the first time after two and a half yearsWatch & ListenSpotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8tApple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323Social MediaWebsite: brooklyntea.comBrooklyn Tea Instagram: @brooklynteaJamila's Instagram: @jamilawright21 Hosted on Acast. See acast.com/privacy for more information.
- 2 weeks ago1h 2m
521: How Cynthia Bailey and Dana Hill-Robinson Built Glowissima Skincare
If this resonated with you, here are additional resources:⭐ APPLY TO SHIFT: https://sidehustlepro.co/shiftIn 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 How Cynthia and Dana met at a New York hair salon in the 1990s Cynthia's move from Alabama to New York at eighteen to model The Essence cover that became Cynthia's big break The move from modeling into reality television Lessons from closing the Bailey Wine Cellar and the Bailey Room Dana on pivoting Cocotique into a health and wellness hub The formulation story and meaning behind the name Glowissima Turning a thirty-year friendship into a business partnership Sourcing manuka honey and kiwi seed oil from New Zealand Digging deeper on marketing when the economy shiftsWatch & ListenWatch this episode on YouTube and listen on all podcast platforms:Apple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323Spotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8tYouTube: https://www.youtube.com/sidehustleproAnnouncementsApplications are now open for Shift, my 12-week coaching program designed to help experienced professionals package their expertise into a profitable offer, identify their first clients, and confidently launch their next chapter.Learn more and apply at: https://sidehustlepro.co/shiftSocial MediaCynthia Bailey: Instagram @CynthiaBaileyDana Hill-Robinson: Instagram @DanaHillRobinsonGlowissima: Instagram, Facebook, and TikTok @GlowissimaCocotique: Facebook @CocoTique, TikTok @CocoTiqueBeautyBox Hosted on Acast. See acast.com/privacy for more information.
- 3 weeks ago1h 3m
520: How Jotaka Eaddy Built a Movement of 44,000 Black Women Overnight
If this resonated with you, here are additional resources:⭐ APPLY TO SHIFT: https://sidehustlepro.co/shiftIn this episode, I sat down with Jotaka Eaddy, founder of Full Circle Strategies and Win With Black Women, for a conversation about power, purpose and resilience. We talked about her childhood in Johnsonville, South Carolina, a town of under 1,400 people that taught her the value of community long before she ever set foot in Washington, DC or Silicon Valley.Jotaka walked me through her path from student activist against the death penalty to senior advisor at the NAACP to becoming the first Black employee at a fintech startup in Silicon Valley. She opened up about the layoff that nearly broke her and the Oprah Winfrey clip that helped her reframe it as redirection rather than failure.We also talked about how Win With Black Women was born from a single late night email in 2020 that turned into a Zoom call with 44,000 women, and how that same community continues to organize today. Jotaka got vulnerable about losing her mother during the 2024 election season and what that grief has taught her about faith, resilience and asking for help.Main TakeawaysYour community can be your first investors. The people of Jotaka's hometown pooled money so she could attend a conference that changed the course of her life.A layoff is not always failure. It can be redirection toward something bigger than you could have planned for yourself.Movements are built in the quiet, consistent work that happens long before anyone is watching or celebrating.Black women hold real power at the ballot box and in daily acts of organizing, even while in survival mode.Highlights Include02:01 - Growing up in Johnsonville, South Carolina05:04 - The conference that changed her life11:46 - Learning to lead by carrying the bag15:17 - Making the leap into Silicon Valley19:08 - Getting laid off and finding strength in an Oprah Winfrey clip29:02 - The spark behind Win With Black Women35:40 - The night 44,000 women joined the call44:53 - How to show up when you are in survival mode48:05 - Opening up about losing her motherWatch & ListenWatch this episode on YouTube and listen on all podcast platforms:Apple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323Spotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8tYouTube: https://www.youtube.com/sidehustleproAnnouncementsApplications are now open for Shift, my 12-week coaching program designed to help experienced professionals package their expertise into a profitable offer, identify their first clients, and confidently launch their next chapter.Learn more and apply at: https://sidehustlepro.co/shiftSocial MediaJotaka Eaddy: Instagram: @JotakaEaddyWin With Black Women: Instagram: @WinWithBlackWomen Hosted on Acast. See acast.com/privacy for more information.
- Jun 20, 202625 min
519: After 10 Million Downloads, Here’s What I Learned
If this resonated with you, here are additional resources: ⭐ APPLY TO SHIFT: https://sidehustlepro.co/shiftWhen I launched Side Hustle Pro, I thought success would be measured by downloads, rankings, sponsorships, and audience growth. And while reaching 10 million downloads is a milestone I'm incredibly grateful for, I've learned that the true value of podcasting has very little to do with the number itself.In this episode, I share the biggest lessons I've learned after more than 500 episodes and 10 million downloads. From building meaningful relationships and creating opportunities I never could have predicted to developing new business offers, growing a loyal community, and gaining clarity on my next chapter, podcasting became much more than a content platform. It became a vehicle for transformation.Whether you're a podcaster, entrepreneur, creator, or professional looking to build your personal brand, this episode will challenge you to think differently about what you're creating and how it can become the bridge to where you want to go next.Main TakeawaysDownloads are not the destination. Trust, relationships, and opportunity are the true assets.A podcast can become a powerful networking tool that opens doors you never expected.Specificity and niching down accelerate discoverability, growth, and community building.Podcasting can help you validate ideas, package your expertise, and build your next business offerHighlights Include00:00 – The lesson behind 10 million podcast downloads01:16 – Why podcasting became my most powerful networking tool03:28 – The new podcasting playbook for creators and entrepreneurs04:17 – Building trust through the intimacy of audio05:39 – My thoughts on video podcasting and discoverability10:34 – Why niche podcasts grow faster than general ones14:50 – Trust as the most valuable asset you build16:27 – How Side Hustle Pro led to national media opportunities18:30 – The unexpected doors podcasting opened for my career20:04 – Why most podcasts struggle to grow21:36 – How podcasting became the bridge to my next chapter23:52 – Why I created the Shift ProgramLinks Mentioned in This EpisodeShift Program: https://sidehustlepro.co/shiftWatch & ListenWatch this episode on YouTube and listen on all podcast platforms:Apple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323Spotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8tYouTube: https://www.youtube.com/sidehustleproAnnouncementsApplications are now open for Shift, my 12-week coaching program designed to help experienced professionals package their expertise into a profitable offer, identify their first clients, and confidently launch their next chapter.Learn more and apply at: https://sidehustlepro.co/shiftSocial MediaInstagram: @sidehustlepro Hosted on Acast. See acast.com/privacy for more information.
- Jun 12, 202630 min
518: The ONE skill you need to learn before you QUIT
If this resonated with you, here are additional resources: ⭐ APPLY TO SHIFT: https://sidehustlepro.co/shiftIn this solo episode, I am getting real with you about the one skill that changed everything for me and that I believe every woman needs to develop right now: learning how to make money directly for yourself. I am sharing why the leap from employee to entrepreneur is so hard, how our entire lives have programmed us to earn money for someone else, and what it truly takes to start creating money on your own terms.I take you back to my days at NPR, where I was climbing the ladder, playing the game, and quietly building Side Hustle Pro on the side. I share how a hater coworker who reported me to my boss became the catalyst for my exit plan, how I landed my first $4,000 podcast sponsorship from a cold customer service email, and how learning just two revenue streams gave me the confidence to leave my job for good.This episode is also a reminder that you do not have to have everything figured out before you start. Your first $20 or $25 outside of your paycheck changes something in you that no amount of planning can replicate. If you are sitting at a crossroads wondering what your next move is, this episode is your sign to start choosing yourself.Main TakeawaysThe difficulty of leaving a job is not fear or lack of risk tolerance; it is decades of programming to earn money for someone else, and that programming can be unlearned.Earning money depends on someone else choosing you, while creating money is about identifying a problem, building a solution, and offering it to the world.You do not need two revenue streams mastered before you act; your first dollar outside a paycheck unlocks a shift in confidence and mindset that no amount of planning can give you.Showing up imperfectly is part of the process; authenticity attracts the right people and gives your audience permission to let their guard down too.Highlights Include00:01 - Why I chose to record this episode on the go with ease over perfection02:27 - How jobs program us to earn money for someone else and why that makes the leap so hard03:06 - The story of bringing my now-husband Muoyo to my NPR holiday party and what it revealed about being stuck in the corporate mindset07:31 - Why smart, experienced, degreed women still feel stuck and what they are actually missing09:49 - The difference between earning money (someone choosing you) and creating money (creating value)12:15 - Why showing up imperfectly is how you attract your people, especially as Black women in professional spaces14:37 - Why relying on someone else to choose you is bad for your mental health, and what to do instead18:47 - My personal backstory: launching Side Hustle Pro while at NPR and investing $1,197 in a sponsorship intensive21:06 - How a cold email to a customer service inbox landed me my first $4,000 podcast sponsorship contract25:52 - The coworker who reported me to HR and how that moment became the push I needed to start my exit plan00:00 (Part 2) - Why your first $25 changes everything internally and how making money directly for yourself is the skill to build right nowLinks Mentioned in This EpisodeShift Coaching Program: sidehustlepro.co/shiftWatch & ListenListen to Side Hustle Pro on Apple Podcasts: podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323Listen on Spotify: open.spotify.com/show/13qDj08lBR4ymzGhXIKy8tAnnouncementsSHIFT, my transformational coaching program for ambitious women who want to turn their side hustle into their exit plan from their 9-to-5, is now open for applications. Apply now at sidehustlepro.co/shift before spots fill.Social MediaSide Hustle Pro Instagram: @SideHustlePro Hosted on Acast. See acast.com/privacy for more information.
- Jun 5, 202626 min
517: After Quitting My 6-Figure Job to Launch My Own Business Here’s What I Learned
If this resonated with you, here are additional resources: ⭐ APPLY TO SHIFT: https://sidehustlepro.co/shiftIn this solo episode, I'm pulling back the curtain on my entrepreneurial journey and sharing the six most important lessons I've learned since leaving my corporate job in 2017. Most people assume that quitting was my biggest risk, but the truth is, the scariest steps happened long before I ever turned in my notice.I take you all the way back to 2015, when I graduated from business school without a job after not receiving the full-time offer from my Google internship. From studying abroad in Barcelona to avoid reality, to moving back to DC and starting a blog with no plan, this episode is about what really happens in the messy middle before success shows up. I share how rejection led me to NPR, how my experience there became the foundation for Side Hustle Pro, and how I earned my first $4,000 sponsorship contract from a cold email to a customer service inbox.This episode is for anyone who is waiting for a sign, a plan, or the perfect moment. Spoiler: that moment is not coming. What is coming is everything you need to build, but only if you start. I break down exactly how I got here and what I want you to take away from this milestone journey.Main TakeawaysRejection is redirection: Not getting the Google offer was the push that led Nicaila to build Side Hustle Pro.You don't need the whole plan: Taking one next step, even without knowing where it leads, is how clarity is built.Clarity comes from action: The idea for Side Hustle Pro did not come before the action; the action revealed the idea.Bet on proof, not hope: Nicaila didn't quit her job out of fearlessness, she quit because she had consistent data showing her business could grow.Highlights Include[00:02] I share the real biggest risk I took, and it wasn't quitting my job[00:24] The Google internship story: expecting the full-time offer and not getting it[02:45] Graduating from business school with no job, no plan, and moving back to DC[04:40] Lesson 1: Rejection is redirection, and what that looked like in real life[07:16] Lesson 2: You don't need the whole plan, just the next step[00:02 segment 2] Lesson 3: Clarity comes from action, not waiting for an aha moment[03:11] How Side Hustle Pro's concept was born out of a boring blog pivot[07:26] Lesson 5: Bet on proof, how I earned my first $4,000 sponsorship[11:37] The real reason I quit: not fearlessness, but evidence[12:19] Lesson 6: The life you want is built before you leave, not afterLinks Mentioned in This EpisodeAPPLY TO SHIFT: https://sidehustlepro.co/shiftWatch & ListenListen to Side Hustle Pro on Spotify: open.spotify.com/show/13qDj08lBR4ymzGhXIKy8tListen on Apple Podcasts: podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323Social MediaInstagram: @SideHustlePro Hosted on Acast. See acast.com/privacy for more information.
- May 29, 20261h 0m
516: From Caregiver to CEO: How Camille Joy Robinson Turned Her Son’s Diagnosis Into a Movement
In this episode, I sat down with Camille Joy, founder of the Moments of Joy Podcast and author of Moments of Joy: 90 Days of Encouragement, published by Penguin Random House. Camille is a trafficking survivor who escaped an abusive situation at 21, became a high school dropout turned executive chef, and fought her way into a six-figure salary by going directly to the CEO. When her youngest son Mason was diagnosed with autism, everything shifted again, and a raw, tear-filled video she recorded in her car after a difficult doctor visit went viral with over six million views in 2022.Today Camille runs two businesses: Moments of Joy, her for-profit media brand built on brand deals, speaking, and her book, and Awesomely Different, her nonprofit that provides swimming lesson grants for children with autism. She also shares how she and her filmmaker husband manage it all without a village, and what it really took to land Holly Robinson Peete as a podcast guest after five attempts over several years.Main TakeawaysYour test is your testimony: Camille's openness about trafficking, autism, and grief is what built her audience and her business.Tackle the shame first: Before you can turn your story into impact, you have to get comfortable sharing what you have been through.Serve before you ask: Camille landed Holly Robinson Peete as a guest by consistently showing up in her community, buying her book, attending her events, and reaching out five times before getting a yes.Caregiving and entrepreneurship can coexist: Camille and her husband run two businesses while raising Mason by communicating constantly, sharing schedules, and giving each other permission to pursue their goals.Highlights Include00:46 - Camille shares what life looked like before the Moments of Joy Podcast existed01:45 - Mason's birth story and three heart surgeries in 18 months02:42 - Receiving Mason's autism diagnosis and how it changed everything04:40 - Camille reveals she is a trafficking survivor and how she escaped at 2106:06 - How a stranger saying her name out loud was the sign she needed to go to culinary school09:14 - Fighting for the executive chef title at ConAir Corporation by CC'ing the CEO11:13 - Going to the CEO directly to demand her six-figure salary and getting it on the spot23:22 - The viral reel that changed everything: 6 to 7 million views after a tearful moment in the car27:06 - Launching Awesomely Different, her nonprofit that teaches children with autism to swim31:52 - Signing with Penguin Random House and the reality of first-round edits38:45 - How Camille and her husband manage two businesses and Mason's care without a traditional village46:01 - Why tackling shame is the first step to turning your test into a testimony52:03 - The strategy behind landing Holly Robinson Peete and why she reached out five times56:17 - Lightning round: resources, role models, daily non-negotiables, and parting adviceLinks Mentioned in This EpisodePodcorn (early podcast sponsorship platform): https://podcorn.comMoments of Joy Podcast: https://www.mojpodcast.com/ Watch & ListenSide Hustle Pro Podcast on Spotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8tSide Hustle Pro Podcast on Apple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323Social MediaInstagram: @momentsofjoypodcastTikTok: @momentsofjoypodcast 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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