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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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- 1 weeks ago1h 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.
- 2 weeks ago59 min
515: From Corporate to Creative: How Jessica Lane Alexander and Lori Hall McKissic Built Pop’N Creative into a $4M Agency
In this episode, I sat down with the powerhouse duo behind Pop’N Creative, Jessica Lane Alexander and Lori Hall McKissic. These two met years ago at Turner Broadcasting and spent years rising through the ranks of some of the biggest names in media and entertainment, including TBS, TNT, UPTV, and TV One, before finally betting on themselves. Their story is one of calculated risk, deep friendship, and relentless creative vision.I was so excited to finally get them both on the show and dig into the real behind-the-scenes of how Pop’N Creative came to be. They walked us through the eight-week planning process over dinners and drinks that turned into a real business, how they launched in February 2020 (yes, right before the pandemic), and how they survived and thrived when the world shut down. They bootstrapped everything, pivoted their model on the fly, and landed clients like Freeform, Hulu, and National Geographic along the way.We also got into the money conversation because the glitz and glamour of events and activations has a whole financial infrastructure behind it. We talked about payment terms, cash flow management, how to structure agency contracts, and what it really takes to grow to the $4 million revenue range as a small boutique agency. If you are building something in the creative or service space, this one is full of gems.Main TakeawaysStart before you are fully ready: Pop’N Creative launched in February 2020, and the pandemic that followed actually forced them to pivot into a social-first model that helped them grow.Use the 60% rule: Before leaving your full-time job, aim to have 60% of your target salary locked in through contracts so you have enough security to leap without operating from fear.Master cash flow, not just revenue: Payment terms of net 60 to net 90 are common in the agency world, so having a business line of credit and a great accountant are non-negotiable early hires.Your network IS your net worth: From their first capabilities presentation to their Cannes Lions shortlist, every major win came from relationships they had built over years in the industry.Highlights Include00:53 - Jessica and Lori share their individual career journeys through Turner, Kellogg Business School, Microsoft, UPTV, and TV One09:07 - The moment Jessica first told Lori "we could do this ourselves" and how she pitched the idea twice before it stuck10:35 - How they tested the business concept during eight weeks of structured planning sessions over dinner and drinks13:38 - Launching Pop’N Creative in February 2020, just weeks before the pandemic shut everything down14:01 - How Lori's unexpected layoff during the pandemic became the best thing that ever happened to her entrepreneurial journey19:06 - Landing their very first capabilities presentation with Freeform (Disney) and wowing a room of 15 people on their first try25:27 - How they bootstrapped and self-funded Poppin to retain full autonomy, and what happened when their first big event contract got canceled27:49 - The Hulu skating rink at Essence Festival and how they pivoted to experiential work post-pandemic47:14 - Pitching National Geographic on a wild-card Fashion Week idea with holographic animals that got shortlisted at Cannes Lions59:31 - Their parting advice: the 60% rule for leaving your job and why finding a business partner or lieutenant makes all the differenceLinks Mentioned in This EpisodePop’N Creative Website: https://www.popncreative.comWatch & 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 MediaPop’N Creative: @popncreativeJessica Lane Alexander: @LaneJessDLori Hall McKissic: @loriJAY Hosted on Acast. See <a style='color:grey;' target='_blank' rel='no
- 3 weeks ago1h 16m
514: From Tutoring Classmates in High School to $1M College Prep CEO w/ Janae Young
In this episode, I sat down with Janae Young, founder and CEO of Young College Prep, who started her first business at just 15 years old, tutoring classmates out of her school library in Wilmington, North Carolina. By the time she graduated high school, she had a team of eight tutors. By the time she graduated from Stanford, she had hit $300K in annual revenue. And by 2025, she crossed her first million.But Janae's path was anything but linear. COVID wiped out the SAT/ACT prep market practically overnight, and her company went into negative profit. She was a freshman in college, going through a breakup, studying computer science remotely and somehow she held on. What she shares in this episode about staying stubborn in the quiet moments, investing $25K in herself as a 19-year-old college student, and pivoting her business model to serve parents instead of students is the kind of transparency you don't often hear.Janae also opens up about navigating the college admissions landscape in a post-affirmative action era, why she believes the college application process is a metaphor for life, and how she's helping students of color tell their stories powerfully. If you're an entrepreneur in a side hustle chapter or a parent thinking about your kid's future this one is for you.Main TakeawaysInvest in yourself before you feel ready: Janae wired $25K to a mastermind as a 19-year-old college student with almost nothing left in her account and that bet changed everything.Know who actually holds the decision and the wallet: When Janae shifted her focus from students to parents, her revenue took off.Real urgency comes from the problem, not just the deadline: Make your client deeply aware of what inaction is costing them for Janae's audience, that's potentially $100K+ in lost merit scholarships.Selling is just teaching: When you see yourself as an educator first, the "sleazy" feeling disappears and you become a genuine guide.Highlights Include Janae started her tutoring business at 15 because she was too young to work at Chick-fil-A Hiring and firing her first employee at 16 -- including a tutor who poached a client and cited contract law to get away with it How COVID wiped out the SAT/ACT market overnight and sent her business into negative profit Screen recording a webinar, then closing 4 out of 5 people at $500 the very next night Wiring $25K to a mastermind at 19 -- and the phone call her mom got from the bank Why shifting her target from students to parents changed her revenue trajectory How she structured her Stanford schedule to be a student Mon-Wed and a CEO Thu-Fri Breaking down her two offers: Ivy League Score ($2,500) and Ivy League Acceptance ($12K) Her organic and paid marketing mix: podcast, ads, and live and evergreen webinar funnels Her response to the affirmative action ruling and how she helps students of color own their storyLinks Mentioned in This EpisodeYoung College Prep website: janaetutoring.comStacey Boehman -- 2K for 2K program: staceyboehman.com/2kfor2kDielle Charon -- Six Figure Liberation mastermind (formerly called Sales Queen): diellecharon.comClaire Pelitro (Claire Pels) -- Get Paid Marketing: clairepells.comAmy Porterfield -- amyporterfield.comBrooke Castillo -- The Life Coach School: thelifecoachschool.comWatch & ListenListen to the Side Hustle Pro podcast on Spotify, Apple Podcasts, and wherever you stream podcasts. Watch full video episodes on the Side Hustle Pro YouTube channel.Social MediaInstagram: @JanaeTutoringFacebook: @JanaeTutoringPodcast: <a href="https://podcasts.apple.com/us/podcast/get-accepted/id1757845807" rel="noopene
- 4 weeks ago1h 6m
513: Tiffany Aliche on What the Hard Years Teach You About Money and Resilience
This week in the guest chair is Tiffany Aliche, known to millions as the Budgetnista and the author of the New York Times bestseller Get Good With Money. Tiffany is back for a deeply personal conversation about what burnout actually looks like when you’re at the top of your game, and what it finally took for her to listen to herself.She opens up about the physical and emotional signs she ignored for too long, the scary truth she finally admitted to her therapist, and how a solo trip to Sedona shifted everything. She also takes us inside the business pivot happening at Budgetnista, from being the face of everything to stepping back and watching her company grow 74% in a single quarter.We also get into the deeper financial conversation: the difference between financial freedom and financial wholeness, how to release financial shame, and the two questions Tiffany now leans on in even her darkest moments. This one is rich from start to finish.Main TakeawaysBurnout is misalignment, not overworkWhy stepping back from being the face of your brand can grow your businessFinancial wholeness vs. financial freedom: which goal actually serves youHow to release financial shame and start your money journey without going it aloneHighlights Include00:00 - Tiffany’s burnout: blood pressure spikes, Oura Ring stress alerts, and a back that gave out03:00 - The thing she finally said out loud and how it shifted her physical pain08:10 - Why her COO reframed burnout: it’s not hard work, it’s misalignment10:54 - Zone of excellence vs. zone of genius21:17 - Transparent look at Budget Nista’s revenue journey from a $10M peak to today’s upswing23:41 - The B2B contract pivot: Newark schools, United Way, and NYC Dept of Education43:38 - Wealth guilt, giving beyond the overflow, and learning to drink from your own cup48:08 - A three-part framework for starting your financial journey: community, voice, and vision56:50 - Financial wholeness explained: the 10 pillars and why this goal is for everyone01:01:30 - Two questions to ask in your hardest moments: Is this true? Is it the only truth available?01:03:34 - Tiffany previews her upcoming book, The Gifts of Grief, and her 2027 sabbaticalLinks Mentioned in This EpisodeGet Good With Money: getgoodwithmoney.comThe Big Leap by Gay Hendricks (recommended by Tiffany)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 MediaTiffany Aliche's Instagram: @thebudgetnistaSide Hustle Pro - @sidehustlepro Hosted on Acast. See acast.com/privacy for more information.
- May 1, 202643 min
512: How Leah Collins Turned Financial Mistakes Into a TV Show, Multiple Income Streams, and a Purpose-Driven Career
This week in the guest chair is Leah Collins, financial coach, speaker, and host of Maxxed Out, a powerful series helping people confront their finances and the relationships tied to them. But Leah’s journey didn’t start on TV, it started with a moment of truth: making the most money she ever had… and realizing she had nothing to show for it.In this episode, I sit down with Leah to unpack how she transformed her own financial struggles into a thriving business, paid off $40,000 in debt, and ultimately landed her own show. We talk about the behind-the-scenes reality of building a personal brand, why communication is the foundation of financial success, and how she leveraged every opportunity to create multiple income streams.Leah also opens up about one of the most pivotal moments in her life: calling off her wedding due to financial incompatibility. That experience reshaped her entire mission and led her to focus on money and relationships, helping others navigate the conversations so many of us avoid. This episode is a masterclass in turning pain into purpose and building a life that aligns with your values.Main TakeawaysTurning personal financial struggles into a business can create powerful impact and incomeFinancial compatibility and communication are critical in relationshipsYour personal brand is always working for you, even when you don’t realize itMultiple income streams, including speaking, media, and passive products, create flexibility and freedomHighlights Include00:00 – Why money affects every part of your life02:10 – 20 years in corporate finance but struggling personally04:05 – Wake-up call: high income, no results04:40 – $100 bootcamp → $40K debt paid off05:20 – Calling off her wedding over money misalignment07:06 – Prenups, communication, and financial expectations09:05 – Turning personal pain into a business niche10:53 – Launching her brand → getting discovered for TV12:11 – Building a strategic personal brand that attracts opportunities14:17 – TV journey: rejection, delay, and eventual greenlight16:46 – Scaling after motherhood and shifting business model20:43 – Behind the scenes of Maxed Out and building trust23:03 – Leveraging TV into multiple income streams24:55 – Values-based finances and smarter decision-making26:51 – Balancing a 9–5 while growing a business29:37 – Storytelling as a tool for impact and connection31:27 – Pitching yourself and understanding media monetization34:11 – “You’re always being interviewed” mindset38:13 – Why quality beats quantity in content41:02 – Burnout, boundaries, and protecting your time41:42 – Final advice: build your business without quitting your jobLinks Mentioned in This EpisodeMoney Moves Makeover: https://www.amazon.com/OWN Network: https://www.oprah.com/ownHBO Max: https://www.max.com/Discovery+: https://www.discoveryplus.com/Save the Date: Start the Podcast That Builds Your Exit Plan (Friday, May 15)Watch this episode on YouTube and listen on all podcast platforms:Apple Podcasts: https
- Apr 24, 202643 min
511: Monica Cornitcher’s Journey From Personal Loss to Non-Alcoholic Cocktail Success
I sat down with Monica Cornitcher, CEO and co-founder of Medase Cocktails, a premium non-alcoholic beverage brand redefining what it means to drink without alcohol. What started as a simple desire for a real cocktail experience without the after-effects turned into a six-figure investment and a fast-growing brand that’s now catching the attention of major retailers.Monica shares how she and her co-founder Inga Dyer went from Zoom conversations during the pandemic to building a fully developed beverage company. Instead of rushing the process, they leaned into research, worked with a food scientist, and built a five-year strategy before launching. Their focus was clear: create authentic, full-flavor cocktails that people actually recognize and crave.In this episode, Monica opens up about the real cost of building a physical product, navigating grief after losing her co-founder, and the strategy behind growing through direct-to-consumer before entering retail. This is a powerful conversation about resilience, intentional growth, and building a brand rooted in purpose and community.Main TakeawaysWhy taking time to validate your idea and build a strategy can save you costly mistakesHow to approach launching a physical product without cutting corners on qualityThe importance of direct-to-consumer growth before entering retailHow resilience, grief, and purpose shaped the future of Medase CocktailsHighlights Include00:00 – Introduction to Medase Cocktails03:00 – Monica’s first business and corporate background06:00 – The idea sparked during COVID and building with intention08:00 – Why they worked with a food scientist instead of DIY10:00 – Creating a 5-year business strategy before launch13:00 – Identifying their target consumer and product positioning21:00 – Funding the business with $100K+ of personal investment26:00 – Attending Expo West and attracting investors29:00 – Navigating grief after losing her co-founder30:00 – Growth on Amazon and direct-to-consumer success33:00 – Why retail is expensive and how to prepare for it45:00 – Lessons from production mistakes and product quality control47:00 – Competing in a growing non-alcoholic beverage market50:00 – Lightning round insights and toolsLinks Mentioned in This EpisodeSave the Date: Start the Podcast That Builds Your Exit Plan (Friday, May 15)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/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 PlanSave your seat here. Social MediaInstagram: @medasecocktailsTikTok: @medasecocktailsFacebook: Medase CocktailsSide Hustle Pro – @sidehustleproSideHustlePro Hosted on Acast. See acast.com/privacy for more information.
- Apr 17, 202649 min
510: How I'm Rebuilding After A Hard Season (feat. Monique Shields)
In this episode, I’m joined again by Monique Shields, and this conversation felt like therapy, coaching, and truth-telling all in one. We went deep into something I’ve personally been navigating: what it actually looks like to move out of survival mode as a high-achieving woman, especially when life has been life-ing.We talked about the invisible weight many of us carry, from parenting to business to unexpected life challenges, and how that impacts the way we show up, make decisions, and even spend money. One of the biggest shifts for me? Realizing I wasn’t telling myself the full story about what I had been carrying and surviving.Monique breaks down how our mindset around scarcity, energy, and outsourcing can keep us stuck, and what it really means to “resource yourself” instead of just pushing through. If you’ve been feeling stuck, foggy, or like you’re doing everything but still not moving forward, this episode will hit home.Main TakeawaysYou’re not behind, you’re likely operating without acknowledging everything you’ve been carryingScarcity mindset after a hard season can quietly shape your decisions and keep you stuckYour energy, not just your time, is one of your most valuable assetsResourcing yourself (mentally, physically, strategically) is essential for growthHighlights Include00:00 – Reconnecting with Monique and what she’s been building02:30 – Why intimate spaces and coaching containers matter04:30 – Starting YouTube and breaking through creative burnout06:00 – The hidden impact of hard seasons on decision-making08:00 – Why you’re not telling yourself the full story10:00 – High-achievers and the trap of self-pressure12:30 – Why “feeling less overwhelmed” isn’t the right goal15:00 – Scarcity mindset after financial or life shocks18:00 – Why cost-first thinking keeps you stuck21:00 – The “delusional belief” successful people hold about their future27:00 – The real value of your time and energy33:30 – What actually changed after hiring support36:00 – Mental fog and why you don’t even realize you’re in it40:00 – Why stability is not the same as hoarding43:00 – What it really means to “resource yourself”46:00 – The importance of having multiple “brains” supporting you50:00 – Why your nervous system needs support in today’s world52:00 – Reframing “I can’t afford it” into a choiceLinks Mentioned in This EpisodeSave the Date: Start the Podcast That Builds Your Exit Plan (April 17)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/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 PlanSave your seat here. Social MediaInstagram: @moniquershieldsPodcast: Ambition Without CompromiseSide Hustle Pro – @sidehustlepro#SideHustlePro Hosted on Acast. See acast.com/privacy for more information.
- Apr 10, 202632 min
509: Opening Up About My Journey as an Autism Mom
This episode is one of the most personal and vulnerable conversations I’ve ever shared. I’m opening up about my journey as an autism mom, from the early days of pregnancy and motherhood during the pandemic to navigating the realities of developmental delays, diagnoses, and advocacy. What started as subtle concerns about speech delays turned into a life-changing journey through early intervention, therapy, and eventually receiving an official autism diagnosis for my son. Along the way, I’ve had to learn how to advocate fiercely, navigate complex systems, and redefine what motherhood looks like for me and my family.This episode is about the hard moments, the emotional weight, and the unexpected beauty in this journey. It’s also about community, resilience, and learning to see strength in a path that looks different than what I once imagined.Highlights Include00:00 – Why this episode is deeply personal02:00 – Pregnancy, birth, and early milestones during the pandemic04:30 – First signs of speech delay and comparing developmental milestones06:30 – The emotional impact of early evaluations07:30 – Starting early intervention: speech and occupational therapy09:00 – Transition to specialized preschool and navigating the system11:00 – The hidden challenges of parenting a child with special needs12:30 – Communication barriers and emotional regulation as a parent14:00 – The moment I realized how much I’ve been carrying16:40 – Understanding gestalt language processing19:30 – Getting an official autism diagnosis21:00 – Advocating for my son within the school system23:30 – A “guardian angel” moment that changed everything27:00 – The role of faith in navigating this journey29:00 – Finding community and learning from other moms30:30 – Lessons autism has taught me about boundaries and perspective31:00 – A real-life parenting moment at the barbershop33:00 – Choosing celebration during Autism Awareness MonthLinks Mentioned in This Episode• Save the Date: Start the Podcast That Builds Your Exit Plan (Friday, April 17)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/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 PlanSave your seat here. Social MediaSide Hustle Pro – @sidehustlepro#SideHustlePro 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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