BusinessEntrepreneurshipMarketing

Side Hustle Pro

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!

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

Play

Open in

28 episodes
weekly
Avg 48 min
English

Episodes 28

Newest Oldest Longest

All8 Unplayed8 In progress0 Played0

Counted on this page — what you have heard stays on this device, so it is not something the list can be paged by.

May 8 · 1 hr 6 min
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 Takeaways Burnout is misalignment, not overwork Why stepping back from being the face of your brand can grow your business Financial wholeness vs. financial freedom: which goal actually serves you How to release financial shame and start your money journey without going it alone Highlights Include 00:00 - Tiffany’s burnout: blood pressure spikes, Oura Ring stress alerts, and a back that gave out 03:00 - The thing she finally said out loud and how it shifted her physical pain 08:10 - Why her COO reframed burnout: it’s not hard work, it’s misalignment 10:54 - Zone of excellence vs. zone of genius 21:17 - Transparent look at Budget Nista’s revenue journey from a $10M peak to today’s upswing 23:41 - The B2B contract pivot: Newark schools, United Way, and NYC Dept of Education 43:38 - Wealth guilt, giving beyond the overflow, and learning to drink from your own cup 48:08 - A three-part framework for starting your financial journey: community, voice, and vision 56:50 - Financial wholeness explained: the 10 pillars and why this goal is for everyone 01:01:30 - 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 sabbatical Links Mentioned in This Episode Get Good With Money: getgoodwithmoney.com The Big Leap by Gay Hendricks (recommended by Tiffany) 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 Social Media Tiffany Aliche's Instagram: @thebudgetnista Side Hustle Pro - @sidehustlepro Hosted on Acast. See acast.com/privacy for more information.
May 1 · 43 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 Takeaways Turning personal financial struggles into a business can create powerful impact and income Financial compatibility and communication are critical in relationships Your personal brand is always working for you, even when you don’t realize it Multiple income streams, including speaking, media, and passive products, create flexibility and freedom Highlights Include 00:00 – Why money affects every part of your life 02:10 – 20 years in corporate finance but struggling personally 04:05 – Wake-up call: high income, no results 04:40 – $100 bootcamp → $40K debt paid off 05:20 – Calling off her wedding over money misalignment 07:06 – Prenups, communication, and financial expectations 09:05 – Turning personal pain into a business niche 10:53 – Launching her brand → getting discovered for TV 12:11 – Building a strategic personal brand that attracts opportunities 14:17 – TV journey: rejection, delay, and eventual greenlight 16:46 – Scaling after motherhood and shifting business model 20:43 – Behind the scenes of Maxed Out and building trust 23:03 – Leveraging TV into multiple income streams 24:55 – Values-based finances and smarter decision-making 26:51 – Balancing a 9–5 while growing a business 29:37 – Storytelling as a tool for impact and connection 31:27 – Pitching yourself and understanding media monetization 34:11 – “You’re always being interviewed” mindset 38:13 – Why quality beats quantity in content 41:02 – Burnout, boundaries, and protecting your time 41:42 – Final advice: build your business without quitting your job Links Mentioned in This Episode Money Moves Makeover: https://www.amazon.com/ OWN Network: https://www.oprah.com/own HBO 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/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:@theleahmariecollins Side Hustle Pro – @sidehustlepro #SideHustlePro Hosted on Acast. See acast.com/privacy for more information.
April 24 · 43 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 Takeaways Why taking time to validate your idea and build a strategy can save you costly mistakes How to approach launching a physical product without cutting corners on quality The importance of direct-to-consumer growth before entering retail How resilience, grief, and purpose shaped the future of Medase Cocktails Highlights Include 00:00 – Introduction to Medase Cocktails 03:00 – Monica’s first business and corporate background 06:00 – The idea sparked during COVID and building with intention 08:00 – Why they worked with a food scientist instead of DIY 10:00 – Creating a 5-year business strategy before launch 13:00 – Identifying their target consumer and product positioning 21:00 – Funding the business with $100K+ of personal investment 26:00 – Attending Expo West and attracting investors 29:00 – Navigating grief after losing her co-founder 30:00 – Growth on Amazon and direct-to-consumer success 33:00 – Why retail is expensive and how to prepare for it 45:00 – Lessons from production mistakes and product quality control 47:00 – Competing in a growing non-alcoholic beverage market 50:00 – Lightning round insights and tools Links Mentioned in This Episode Save the Date: Start the Podcast That Builds Your Exit Plan (Friday, May 15) 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: @medasecocktails TikTok: @medasecocktails Facebook: Medase Cocktails Side Hustle Pro – @sidehustlepro SideHustlePro Hosted on Acast. See acast.com/privacy for more information.
April 17 · 49 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 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.
April 10 · 32 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 Include 00:00 – Why this episode is deeply personal 02:00 – Pregnancy, birth, and early milestones during the pandemic 04:30 – First signs of speech delay and comparing developmental milestones 06:30 – The emotional impact of early evaluations 07:30 – Starting early intervention: speech and occupational therapy 09:00 – Transition to specialized preschool and navigating the system 11:00 – The hidden challenges of parenting a child with special needs 12:30 – Communication barriers and emotional regulation as a parent 14:00 – The moment I realized how much I’ve been carrying 16:40 – Understanding gestalt language processing 19:30 – Getting an official autism diagnosis 21:00 – Advocating for my son within the school system 23:30 – A “guardian angel” moment that changed everything 27:00 – The role of faith in navigating this journey 29:00 – Finding community and learning from other moms 30:30 – Lessons autism has taught me about boundaries and perspective 31:00 – A real-life parenting moment at the barbershop 33:00 – Choosing celebration during Autism Awareness Month Links Mentioned in This Episode • Save the Date: Start the Podcast That Builds Your Exit Plan (Friday, 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 Side Hustle Pro – @sidehustlepro #SideHustlePro Hosted on Acast. See acast.com/privacy for more information.
April 8 · 34 min
508: The Tax Mistakes Side Hustlers Make That Cost Them Thousands (And How to Avoid Them)
If you’re a side hustler or solopreneur, taxes can go from simple to overwhelming real fast and the truth is, many entrepreneurs are quietly losing thousands of dollars just by not knowing what they don’t know. In this episode, I sat down with CPA and TurboTax Expert Lisa Greene-Lewis to break down the most common tax mistakes side hustlers make, from choosing the wrong business structure too early to missing out on key deductions and failing to stay organized throughout the year. We also unpack what actually makes taxes more complex as your business grows and how to stay ahead of it before tax season hits. This conversation is all about helping you feel more confident, more prepared, and more in control of your finances. Because the goal is not just to make money in your business but to keep more of it. Main Takeaways Lack of consistent tracking is the biggest mistake that leads to overpaying taxes Many solopreneurs miss deductions simply because they are unaware of what qualifies Staying organized year-round is the key to reducing stress and maximizing savings Highlights Include 00:00 – Introduction to tax season for solopreneurs 02:00 – Lisa’s journey into tax expertise and entrepreneurship 05:20 – LLC vs S corp: what you actually need to know 08:20 – When taxes start to feel complicated 09:30 – Why tracking income and expenses is critical 11:40 – Common deductions people miss 13:00 – Home office deduction explained 14:20 – Section 179 and equipment write-offs 15:10 – What you can’t deduct (clothes, hair, makeup) 16:40 – Business credit card interest deduction 17:20 – Employing your kids as a tax strategy 18:00 – SEP IRA and retirement savings for entrepreneurs 19:00 – Qualified Business Income deduction 20:10 – Key tax law updates and 1099-K changes 23:20 – How to stay organized with QuickBooks 25:40 – How TurboTax experts support business owners 27:10 – Lisa’s personal system for staying organized Links Mentioned in This Episode TurboTax: https://turbotax.com/business QuickBooks: https://quickbooks.intuit.com 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 LinkedIn: https://www.linkedin.com/in/lisa-greene-lewis-7721b815a Website: https://turbotax.com/business Side Hustle Pro – @sidehustlepro #SideHustlePro Hosted on Acast. See acast.com/privacy for more information.
March 27 · 28 min
507: The Hidden Cost of Waiting Until You're Ready
If you’ve been waiting for the perfect moment to finally start that thing you said you’d do this year, this episode is your wake-up call. Because the truth is, that moment isn’t coming. This week, I’m pulling back the curtain on a very real, very messy week in my life and sharing why I decided to hit record anyway. From sick kids to mental clutter to a house that is far from organized, I had every reason to wait. But instead, I leaned into a powerful reminder: progress doesn’t require perfection. In this episode, I walk you through the mindset shifts that have helped me move through overwhelm, take action with limited time and energy, and stop letting the idea of “feeling ready” delay my goals. Because sometimes the real work isn’t the task itself, it’s learning how to show up before everything feels aligned. Main Takeaways Waiting for the perfect time will keep you stuck longer than just starting messy You have to work with the time and energy you actually have, not what you wish you had Naming what’s holding you back helps you move through it faster The real growth often comes from managing your mindset, not completing the task Highlights Include 00:00 – Why I recorded this episode despite not feeling ready 02:10 – How “unexpected” life moments keep disrupting plans 04:18 – Learning to work in chaos instead of waiting for order 05:30 – Lowering the bar to get started 06:10 – Work with the time you have, not the time you wish you had 08:00 – Managing your energy to show up at your best 10:15 – Why naming the problem helps you move forward 11:43 – Recognizing the season you’re in and adjusting expectations 14:00 – Are you truly blocked or just thrown off? 16:12 – How accountability helped me launch Side Hustle Pro 18:36 – Overcoming imposter syndrome in a career leap 21:22 – The hidden cost of needing to “have it all together” 23:21 – Why perfection delays your income and growth 26:24 – Maybe the real goal is mastering your mindset 29:19 – Adjusting expectations so you can move forward Links Mentioned in This Episode Save the Date: Start the Podcast That Builds Your Exit Plan (Friday, April 10th) 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 Side Hustle Pro – @sidehustlepro #SideHustlePro Hosted on Acast. See acast.com/privacy for more information.
March 20 · 23 min
506: 5 Simple Ways to Get Paid for What You Already Know
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 Takeaways You do not need new skills or certifications to start making money There are five core ways to monetize what you already know People pay for clarity, speed, and guidance, not just expertise Start with one path and keep it simple instead of trying everything Highlights Include 00:00 – The biggest misconception about making money 01:30 – Why you already have valuable, monetizable knowledge 02:00 – The 5 ways to make money with what you know 03:00 – The mindset shift you need before starting 04:00 – Service and coaching as the fastest path to income 06:00 – Done-for-you services and why people pay for convenience 08:00 – Creating simple digital products that sell 10:30 – Workshops and why people pay for real-time learning 13:00 – Why reminders are key when selling anything 15:00 – Using content to create opportunities and income 18:00 – How to use AI without losing your voice 21:00 – Why you should pick ONE path and start now Links Mentioned in This Episode Save the Date: Start the Podcast That Builds Your Exit Plan (Friday, March 20) 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 Side Hustle Pro – @sidehustlepro #SideHustlePro Hosted on Acast. See acast.com/privacy for more information.

Showing 21–28 of 28 episodes