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Side Hustle Pro

Side Hustle Pro

By: Nicaila Matthews Okome | Side Hustle Pro Media
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Summary

 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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Episodes
  • 512: How Leah Collins Turned Financial Mistakes Into a TV Show, Multiple Income Streams, and a Purpose-Driven Career

    512: How Leah Collins Turned Financial Mistakes Into a TV Show, Multiple Income Streams, and a Purpose-Driven Career
    May 1 2026
    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://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:@theleahmariecollins Side Hustle Pro – @sidehustlepro#SideHustlePro Hosted on Acast. See acast.com/privacy for more information.
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    44 mins
  • 511: Monica Cornitcher’s Journey From Personal Loss to Non-Alcoholic Cocktail Success

    511: Monica Cornitcher’s Journey From Personal Loss to Non-Alcoholic Cocktail Success
    Apr 24 2026
    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.
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    44 mins
  • 510: How I'm Rebuilding After A Hard Season (feat. Monique Shields)

    510: How I'm Rebuilding After A Hard Season (feat. Monique Shields)
    Apr 17 2026

    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 Takeaways
    • You’re not behind, you’re likely operating without acknowledging everything you’ve been carrying
    • Scarcity mindset after a hard season can quietly shape your decisions and keep you stuck
    • Your energy, not just your time, is one of your most valuable assets
    • Resourcing yourself (mentally, physically, strategically) is essential for growth


    Highlights Include
    • 00:00 – Reconnecting with Monique and what she’s been building
    • 02:30 – Why intimate spaces and coaching containers matter
    • 04:30 – Starting YouTube and breaking through creative burnout
    • 06:00 – The hidden impact of hard seasons on decision-making
    • 08:00 – Why you’re not telling yourself the full story
    • 10:00 – High-achievers and the trap of self-pressure
    • 12:30 – Why “feeling less overwhelmed” isn’t the right goal
    • 15:00 – Scarcity mindset after financial or life shocks
    • 18:00 – Why cost-first thinking keeps you stuck
    • 21:00 – The “delusional belief” successful people hold about their future
    • 27:00 – The real value of your time and energy
    • 33:30 – What actually changed after hiring support
    • 36:00 – Mental fog and why you don’t even realize you’re in it
    • 40:00 – Why stability is not the same as hoarding
    • 43:00 – What it really means to “resource yourself”
    • 46:00 – The importance of having multiple “brains” supporting you
    • 50:00 – Why your nervous system needs support in today’s world
    • 52:00 – Reframing “I can’t afford it” into a choice


    Links Mentioned in This Episode

    Save the Date: Start the Podcast That Builds Your Exit Plan (April 17)


    Watch & Listen

    Watch this episode on YouTube and listen on all podcast platforms:

    • Apple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323
    • Spotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8t
    • YouTube: https://www.youtube.com/sidehustlepro


    Announcements

    If 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 Media

    Instagram: @moniquershields

    Podcast: Ambition Without Compromise


    Side Hustle Pro – @sidehustlepro

    #SideHustlePro

    Hosted on Acast. See acast.com/privacy for more information.
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    50 mins
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