Side Hustle Pro

Hosted by Nicaila Matthews Okome | Side Hustle Pro Media

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546

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Nov 2026

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About the show

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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November 3, 202626 min

You Could Get Paid for That: 5 Side Hustles You Can Start Right Now

Extra income does not have to mean a whole new life. In this solo episode, I walk through five side hustles people are doing right now, each one simple enough that you can picture the customer, the work, and why someone would pay for it. We cover flipping items from Facebook Marketplace and offering pickup or delivery, online resale on sites like Poshmark, a resale concierge service for people who want their things sold without the hassle, junk and donation hauling, and setting up one AI workflow for one type of small business. I also share where I have paid for similar services myself, including an after-hours AI assistant at my dentist's office. To close, I break down how to choose the idea that fits your time, money, storage, and transportation, how to find your first customers, and the four-step plan I would follow in the first month. Main Takeaways Pick categories you already know when flipping, and check that the margin covers your time and transport. Selling on someone else's behalf requires permission, platform rules, and a clear agreement on the split. Hauling needs a plan for items donation centers will not accept, plus the right vehicle and insurance. For AI services, master one workflow for one business type before offering anything broader. Highlights Include [00:03] Why these ideas are built for extra income, not a new life [01:54] Idea 1: Flipping Facebook Marketplace finds [04:13] Why a $20 item is not automatically a deal [06:44] Adding a Marketplace pickup and delivery service [07:31] Idea 2: Online resale on Poshmark and similar sites [09:53] Idea 3: Positioning a resale concierge service and building a site with Lovable [13:26] Idea 4: Junk and donation hauling [15:32] What to do when a donation center says no [16:15] Idea 5: Setting up one AI workflow for one small business [18:29] What I learned from my dentist's after-hours AI assistant [23:09] How to choose the idea that fits your time, money, and space [24:59] Finding customers and the first-month plan Links Mentioned in This Episode Lovable: https://lovable.dev Watch & Listen Spotify: 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.

November 2, 202645 min

Why Nobody Bought Your Offer (Even Though They Said They Would)

People told you they would be the first to sign up. Then you launched, and they were nowhere to be found. In this solo episode, I break down why interest and buying are two different decisions, and what an underperforming launch can and can't tell you. I walk through the four signals to separate: what people praise, what they ask for, what they spend time with, and what they pay for. I also cover how to ask about past behavior instead of hypotheticals, how to figure out who actually saw your offer, and the five places a sale can break down: the audience, the problem, the offer, trust, and the invitation. Then I share what I do after a launch that misses my expectations, from talking to buyers and non-buyers to the webinar time test I'm running right now. I close with five questions to answer about the offer you've been sitting on so you can run your next small test. Main Takeaways Praise, requests, attention, and payment each answer a different question about your offer. Ask people about the last time they dealt with the problem, not whether they would buy. Measure who actually saw the offer before deciding nobody wants it. Change one or two things per launch so you know what made the difference. Highlights Include [00:00] When people say they'd buy it, then disappear at launch [02:20] Why your audience isn't necessarily lying to you [04:47] You and your customer are picturing two different offers [05:30] The four signals: praise, requests, attention, and payment [09:33] The meal planning example: asking about real experiences [11:54] What "I can't afford it" really means, and painkillers vs. vitamins [14:08] Start with the people who actually saw the offer [18:22] The five places a sale can break down [25:32] Did you actually ask people to buy? [30:33] Why a small paid pilot can teach you more than a big launch [34:00] What I do after a launch that misses my expectations [38:47] My webinar time test and changing one variable at a time [41:08] Setting a budget and a stopping point for your experiments [45:15] How my Instagram challenge became the Master the Gram course Watch & Listen Spotify: 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.

October 27, 202643 min

You Don’t Have to Be an Influencer to Build a Business

You don't need a huge following or constant access to your private life to build a profitable business. You need to be known for solving a specific problem. In this solo episode, I break down the difference between influence and authority, and between visibility and exposure. I share the questions I ask clients before we talk about anything they don't want to do, starting with what they actually want to be known for. I walk through the three layers of sharing, how I decide what stays private, including how I've approached sharing my journey as an autism mom, and a simple boundary exercise you can use before you post. Then I cover four ways to build authority without becoming a lifestyle influencer: the teacher, the curator, the practitioner, and the connector. We close with how to pick one discovery channel and one owned channel, what consistency really looks like, and how to connect your content to a paid offer you can test. Highlights Include [00:00] Why a profitable brand doesn't require a huge following [01:40] The difference between an influencer and a business owner [02:20] Why my business keeps earning when I step away from Instagram [05:55] Being famous vs. being findable [08:15] The first question to answer: what do you actually want to be known for? [13:15] Visibility vs. exposure, and how I handle sharing my autism mom journey [18:00] The three layers of sharing: expertise, experience, and personal access [22:10] A boundary exercise and the question "What will this yield?" [26:15] The four ways to build authority: teacher, curator, practitioner, and connector [36:00] Discovery channels vs. owned channels, and why social media is rented attention [41:05] The three jobs every piece of business content should do [44:30] Why you should launch before you feel ready, even if you launch to crickets [49:30] Five questions to answer this week Links Mentioned in This Episode Podcast Moguls coaching program: https://sidehustlepro.co/podcastmoguls Hosted on Acast. See acast.com/privacy for more information.

October 23, 202633 min

Why Everyone and Their Mother Has a Podcast

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 Takeaways A 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 show Links Mentioned in This Episode Podcast Moguls: https://sidehustlepro.co/podcastmoguls Watch & Listen Spotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8t Apple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323 Announcements Podcast 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.

October 16, 202637 min

Life Update: How I'm Rebuilding My Business Around My Life

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 Takeaways Design 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 Include Why this episode is audio only and what I removed from the picture Where I was last year compared to where I am now Building my business around motherhood, with most of my work on Tuesdays and Thursdays Deciding what belongs in the business after a year of experimenting Recommitting to Podcast Moguls and keeping it current Launching the first group cohort of SHIFT in July Why Podcast Moguls and SHIFT feel aligned with this season The next chapter: systems, systems, systems Changing my relationship with business and my sense of worth Therapy, postpartum, and getting support for my mental health The 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-downloads Join Podcast Moguls: https://sidehustlepro.co/podcastmoguls Apply for the SHIFT Coaching Waitlist: https://sidehustlepro.co/shift START Your Next Chapter: A Woman's Guide to Taking the Leap with AI by Nadeen Matthews Blair: https://amzn.to/4z2AZs8 Watch & Listen Spotify: 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.

September 30, 202623 min

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 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.

September 25, 202656 min

She Got Laid Off…Then Built a YouTube Income to Pay Her Bills

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 Include 00:00 – 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 Episode Watch Symone’s YouTube video “I Got Laid Off From My 6 Figure Tech Job” Podcast Moguls: Start the Podcast That Builds Your Exit Plan Read Successful Failure by KevOnStage 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, attend my next live class: Start the Podcast That Builds Your Exit Plan. Save your seat here . Social Media YouTube: 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.

September 18, 202653 min

From a Food Blog to a $500K-a-Year Media Business: How Jannese Torres Built Yo Quiero Dinero

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 ready Why she treated her food blog like a non-negotiable commitment and learned SEO and brand partnerships How blog income helped her pay off her student loans and become debt-free in February 2020 Why Yo Quiero Dinero centers Latinas and the power of building for a specific audience How the podcast became the foundation for her book, speaking, brand deals, and other revenue streams Why a podcast team, online business manager, and talent agent are essential to the way she works now How she separates reliable 'pay the bills' offers from 'fun money' offers that give her room to experiment Highlights Include 01:07 - 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 Mentioned Yo Quiero Dinero: https://yoquierodineropodcast.com Connect With Jannese Instagram: @yoquierodineropodcast Hosted on Acast. See acast.com/privacy for more information.

September 11, 202633 min

How to Make Your First $1K Side Hustling

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 strategically How to choose a simple offer you can confidently deliver right now How to identify who your offer is really for and why frustration matters Why 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 $1,000 01:35 – How your mindset shifts after you make your first $1K and why proof matters more than theory 02:31 – What actually counts as an offer and why your first one should be useful, not fancy 03:52 – Why starting with what you’re already confident in is the fastest way to get paid 05:16 – How to decide who your offer is really for and why specificity matters 07:27 – 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 brand 11:22 – Why offering your service is the most important step people delay 12:48 – How confidence and customer focus directly impact whether you make your first $1K 14:04 – Why you don’t need a massive audience — just real conversations and feedback 15:37 – How to use feedback as information instead of taking it personally 17:47 – Why overbuilding and “perfecting” keeps side hustlers stuck 19:21 – Breaking down the math behind $1,000 so it feels achievable 20:45 – Why fewer clients at a higher price can reduce burnout 21:34 – Why most people earn their first $1K from conversations, not content 22:19 – How I made my first $1,000 and what actually worked 26:03 – When to start building your email list and why simple free resources convert better 28:54 – How to use a 12-week sprint to stay focused on your first $1K 29:38 – What to do when your first offer feels slow or doesn’t land immediately 31:08 – What changes after you hit your first $1,000 — and the mistake to avoid next 31:49 – Final action steps to start building your first $1K offer Links Mentioned in This Episode Side Hustle Pro Website: https://sidehustlepro.co/ 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 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.

August 28, 20261 hr 9 min

From YouTube Exec to Full-Time Creator: How Chanel Tyler Turned Content Creation Into 5-Figure Passive Income

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 marketing What happened when the platform responsible for 80% of her income shut down overnight and how she rebuilt Why diversification across platforms, income streams, and partnerships is essential for creators and entrepreneurs How affiliate marketing works and how creators can use performance data to negotiate higher-paying brand deals Highlights Include 00:00 – Introduction 02:10 – Chanel’s career path from investment banking to luxury beauty marketing 05:10 – Building an audience through skincare and product recommendations 09:00 – Landing a role at YouTube working with top creators 15:00 – Saving a year of income before leaving corporate 19:00 – The moment she lost 80% of her income overnight 24:30 – Why diversification is critical for creators and entrepreneurs 27:00 – Building content series that grow an audience 32:00 – Affiliate marketing vs. brand partnerships explained 37:00 – Sharing her journey with hearing loss and disability 40:00 – How statement earrings became part of her empowerment story 43:00 – Affiliate income strategies for creators Links Mentioned in This Episode Substack: Sensible Julia Broome Check out the Networth and Chill Podcast;Creator Economy & Brand Deals with Victoria Paris ShopMy: https://shopmy.us/home/creators MagicLinks: https://www.magiclinks.com/creators BrandCycle: https://brandcycle.com/ LTK: https://company.shopltk.com/en/creator Nordstrom Affiliate Program: https://www.nordstromcreators.com/ Check out Chanel’s Creator Profit Lab’s interest form & course registration 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 Social Media Instagram: @thecreatorprofitlab Instagram: @buymechanel Side Hustle Pro – @sidehustlepro #SideHustlePro Hosted on Acast. See acast.com/privacy for more information.