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!
5 Simple Ways to Get Paid for What You Already Know
Wednesday, September 30, 2026 • Duration 23:58
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:
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
She Got Laid Off…Then Built a YouTube Income to Pay Her Bills
Friday, September 25, 2026 • Duration 56:35
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
Watch this episode on YouTube and listen on all podcast platforms:
Announcements
From a Food Blog to a $500K-a-Year Media Business: How Jannese Torres Built Yo Quiero Dinero
Friday, September 18, 2026 • Duration 53:17
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
Links and Resources MentionedConnect With Jannese
How to Make Your First $1K Side Hustling
Friday, September 11, 2026 • Duration 33:20
If this resonated with you, here are additional resources:
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
From YouTube Exec to Full-Time Creator: How Chanel Tyler Turned Content Creation Into 5-Figure Passive Income
Friday, August 28, 2026 • Duration 01:09:20
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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
Highlights Include
How Karen Young Built OUI the People
Friday, August 21, 2026 • Duration 01:14:01
In this episode, I sat down with Karen Young, founder of OUI the People, a fine fragrance and body care brand born out of her own struggle with razor burn and ingrown hairs. Karen walks us through her path from fashion, where she interned at Dolce and Gabbana, to becoming an executive at Estee Lauder, to eventually building a beauty brand now sold in Sephora.
But Karen's story starts before OUI the People, with a lifestyle and home goods brand called Hammocks and High T that she built and ultimately had to close. We talk about the hard lessons on margins and capital that came out of that experience, the unexpected subway encounter that led to her job at Estee Lauder, and how she used her years inside a major beauty conglomerate to build her own brand from the ground up.
Karen also gets honest about the financial rollercoaster of raising venture capital, scaling a team, and chasing growth without profitability for years, and what finally shifted this year. We close things out with her thoughts on consumer psychology, pricing a premium product, and her advice for women weighing whether to leave a steady paycheck for their side hustle.
Main Takeaways
Why closing a business is not failure, but tuition in a school of hard knocks that teaches you margins, capital, and scale.
How to price a premium product by studying who your customer already trusts enough to spend on, not just what they say they need.
Why visibility does not equal revenue, and how chasing growth without watching profitability can quietly sink a business.
How building a trusted circle of fellow founders can matter more than any book when the entrepreneurial journey gets lonely.
Highlights Include
00:20 - How a lifelong struggle with razor burn and ingrown hairs on melanated skin became the idea behind OUI the People
05:49 - Why Karen closed her first business, a lifestyle and home goods brand called Hammocks and High T
11:19 - Learning the difference between spotting a market gap and finding real money inside of it
16:00 - The subway encounter that led to Karen's job offer at Estee Lauder
25:37 - What Karen absorbed from watching a major beauty conglomerate acquire and scale brands from the inside
Links Mentioned in This EpisodeSocial Media
She Left Corporate Law, Went Back to Work, and Still Built a Global Fashion Brand
Friday, August 14, 2026 • Duration 01:11:27
In this episode, I sat down with Busayo Olupona, founder and creative director of Busayo, the Brooklyn- and Lagos-based fashion brand known for its bold prints and textiles created with artisans in Nigeria. Busayo shares how she went from corporate finance law to bringing handmade pieces home in suitcases, selling them at scrappy pop-ups, and eventually landing in major retailers including Saks Fifth Avenue, Bloomingdale's, Shopbop, and Moda Operandi.
But this conversation goes much deeper than fashion. Busayo opens up about returning to a 9-to-5 after years of entrepreneurship, the shame and fear she had to unlearn, and the two serious cardiac events that forced her to confront the cost of constant striving. We talk about what it takes to build a business without losing yourself, why preparation matters before opportunity arrives, and how faith, meditation, and surrender changed the way she leads.
In This Episode, You Will Learn
Why learning a new industry while you still have a paycheck can protect both your savings and your confidence
How to view returning to a job as reinvesting in your business, not failing at entrepreneurship
Why Busayo had to separate her worth from her corporate title and other people's opinions
How years of creating collections before buyers said yes prepared her for the Saks opportunity
What two serious cardiac events taught her about sleep, stress, self-care, and sustainable ambition
How wholesale relationships can drive recurring revenue, brand discovery, and direct-to-consumer sales
Why Busayo believes faith, meditation, and surrender are practical tools for entrepreneurship
Highlights Include
03:04 - Moving from Nigeria to the United States at age 11 and learning to reject parts of herself to fit in
16:44 - How annual trips to Nigeria planted the seed for the Busayo brand
19:37 - The first pop-up that pushed her to stop hiding her designs
24:05 - Leaving Cleary Gottlieb and unlearning the belief that she was not enough
29:16 - Attending her first trade show and returning with only two orders
31:36 - Meeting mentor Mercedes Gonzalez and learning how wholesale really works
Links and Resources MentionedConnect With Busayo
How Her Wine Became the Obama Presidential Center’s Official White Wine
Friday, August 7, 2026 • Duration 51:33
After a devastating flood forced Chrishon Lampley to close her Chicago art gallery and wine bar, she turned that loss into the foundation for Love Cork Screw, a nationally distributed wine brand that has sold more than two million bottles.
In this episode, Chrishon shares how she broke into the wine industry with no upfront capital, got her products into major retailers, and navigated the realities of building a consumer brand without millions in marketing dollars.
She also reveals how a wine created in honor of her late father became the official white wine of the Obama Presidential Center, and what it took to rebuild after nearly losing the business again.
Main Takeaways
A devastating setback, like losing a business to a flood, can become the foundation for something bigger if you keep moving forward.
Building relationships and repeatedly asking for the sale, even after rejection, can open doors that money alone cannot.
Chasing notoriety across too many markets at once can cost more than it earns; focusing on one market at a time builds real traction.
Consistent, face to camera content can rebuild a business faster than relying on a marketing budget alone.
Highlights Include
[00:32] The flood that closed Three P's Art Lounge and led to Love Corkscrew
[01:26] Becoming one of the first African American women with an on and off premise liquor license in downtown Chicago
[05:58] Starting the Love Corkscrew blog as a way to heal after losing the gallery
[11:14] Explaining what a negociant is and pioneering the term in the wine industry
[17:30] Building Love Corkscrew from nothing through commission and consignment deals
[24:41] The advice from Barefoot Wine's founders that changed her strategy
[32:07] Losing her father and creating the Lampley wine line in his honor
[35:00] Landing the deal to become the official white wine of the Obama Presidential Center
[39:30] Running the Clink and Sip Festival and the Sipping Empower Foundation
[44:29] Committing to daily social media consistency to rebuild the business in 2026
Links Mentioned in This EpisodeWatch & ListenSocial Media
7 Things I Had to Unlearn Before Leaving My Corporate Job
Friday, July 31, 2026 • Duration 43:40
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In this episode, I'm sharing the seven beliefs I had to unlearn before I could finally leave my corporate job and build Side Hustle Pro full time. I spent decades in corporate America, working at places like HBO, MTV, Google, and NPR, and even though I knew I wanted to leave, I wasn't mentally ready until I confronted the internal beliefs that kept me tied to that life.
Highlights Include
00:00 - My corporate background and why I'm scratching the record on old habits
03:01 - The seven things I had to unlearn to build Side Hustle Pro full time
06:48 - Unlearning the need to have my entire future figured out before leaving
11:25 - Why other people's opinions could not be my decision making system
17:31 - Unlearning that a job or promotion was my only path to more money
21:59 - Pay inequity in corporate and why the ceiling is lower than it seems
22:49 - Unlearning that I was limited to doing only what I had already done
27:33 - Confusing busyness with meaningful progress, and the one hour a day model
33:36 - The biggest unlearn: staying employed was not actually the safest option
42:21 - Reflection questions to figure out which belief you're still carrying
In this episode, I sat down with Dawn Fitch, founder of Pooka Pure and Simple, to talk about the winding road that took her from designing album covers in the music industry to building a natural beauty brand rooted in her own health journey. Dawn opens up about the years it took to get an MS diagnosis, and how healing herself led her to start formulating clean, simple products long before she ever thought of herself as a business owner.
We get into the real, unglamorous parts of entrepreneurship: street teaming outside churches before social media existed, a cease-and-desist letter that almost derailed her Whole Foods deal, and the hard lessons of scaling into big box retail. Dawn also shares how she walked away from a failing retail lease with nowhere to go, only to land in the space that's been home to her production for over a decade.
Finally, Dawn walks me through the newest chapter of her story: a 250,000 dollar grant from Audible's DEI program that brought Pooka into a beautiful new Newark location, and how an activity she almost treated as an afterthought, the Bloom Bar, became the biggest draw of the whole business.
Main Takeaways
Protect your business structure early. Trademark your name, keep separate books, and build SOPs before you're forced to by a cease-and-desist letter or a big retail opportunity.
Don't chase big box retail until your core revenue stream is stable enough to absorb the rules, returns, and thin margins that come with it.
When a business decision doesn't feel right, it is okay to walk away even without a backup plan. Trust and timing can lead you somewhere better.
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.
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