Nicaila Matthews Okome | Side Hustle Pro Media
500 episodes listed below
Business coaching for real-life side hustlers.
Side Hustle Pro treats entrepreneurship as something built in real life, not in a perfect calendar block. Recent episodes move from tax questions and creator income to caregiving, health resets, layoffs, and the pressure of waiting to feel ready.
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Side Hustle Pro sits at the intersection of business coaching, personal update, and practical peer-to-peer encouragement. Its recent episodes show a business show that is not afraid to talk about the life around the business. That matters. The advice is about execution, but the friction is often emotional, logistical, or financial before it is strategic. Solo episodes walk through waiting to feel ready, making money from knowledge already earned, and using 12-week sprints to manage health, money, and business without spiraling into overwhelm. Guest episodes add concrete case studies. Chanel Tyler describes moving from corporate work into creator income, affiliate marketing, and brand deals while navigating progressive hearing loss and a sudden income shock. Another guest explains how YouTube revenue, budget templates, physical products, sponsorships, photography, and virtual assistant work became lifelines after a layoff. A tax-focused conversation turns deductions, business equipment, home office rules, and content-creator expenses into plain-language decisions. The coaching-session format brings ambition closer to the microphone, especially around charging more, scaling past six figures, visibility, ownership, and building a business that fits a changed life. The show also makes room for motherhood in an unusually specific way. Episodes reference sick kids, batch-recording plans falling apart, postpartum depression, emotional spending, and the exhaustion of seeking the right support for a child with autism. Those moments are not treated as side notes. They explain why simple advice often needs to be translated into a workable plan. Side Hustle Pro is brisk, intimate, and action-oriented, with a recurring belief that imperfect movement beats waiting for the ideal setup. It is best for people who already suspect they have something valuable to sell but need help naming it, shaping it, and taking the next visible step.
Made for: Side Hustle Pro is for aspiring and active entrepreneurs who are building income around work, family, health, and shifting confidence. It especially suits listeners who want practical business guidance with room for motherhood, money stress, and imperfect starts.
What sets it apart: The show blends tactical entrepreneurship advice with unusually candid life context. It treats taxes, creator monetization, offers, caregiving, layoffs, and mindset blocks as connected parts of the same business reality.
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.
Based on 6 episodes we listened to · September 2026
Side Hustle Pro makes early revenue, offer testing, creator income, and business administration legible through specific questions and candid first-person lessons.
Side Hustle Pro turns early-stage business building into concrete decisions. Nicaila Matthews Okome alternates solo guidance with guest conversations, moving from finding a viable offer and earning a first $1,000 to using AI tools, handling taxes, and assembling several income…
From first $1K to tax deductions, Nicaila Matthews Okome keeps your ambition attached to actual receipts.
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Short reviews from the PlayNext desk, based on the episodes we processed.
A personal autism-parenting episode that turns caregiving strain into a clear, relatable explanation of communication and support.
The episode centers on the host's life as an autism mom, and its strongest turn comes when a birthday text from a best friend makes plain how much she has been carrying.
A practical tax check-in for side hustlers who want fewer surprises and better deductions.
Side Hustle Pro makes tax season feel less punishing and more workable. The conversation stays on the questions side hustlers actually have: what counts, what does not, and where deductions tend to get missed.
A direct push to start before life feels perfectly arranged.
Nikayla keeps the focus on the cost of waiting for the perfect opening. She moves through sick kids, shifting energy, and batch-recording plans that keep getting bumped, then lands on the end of March with a plain reminder: use the time and energy that are actually there, not…
The money-making angle may already be sitting in plain sight.
Side Hustle Pro treats monetization like a packaging problem, not a total reinvention, and that gives the episode its shape. Nikayla Matthews Okome lays out five simple ways to make money from what people already know, drawing on job experience, life experience, and the…
A practical layoff-to-income story about stacking multiple revenue streams to stay afloat.
This episode traces how she kept moving after a layoff by pulling income from several places instead of waiting for one clean fix. YouTube ad revenue, photography, digital products, physical products, brand deals, and virtual assistant work all come up, which keeps the…
A candid reset that turns overwhelm into a monthly plan you can actually use.
Side Hustle Pro frames a personal reset as a workable rhythm, with Nikayla Matthews Okome explaining how she breaks the year into 12-week sprints so health, money, and business stop fighting for space.
The first $1,000 is framed as the point where the work becomes real.
The episode treats the first $1,000 as the point where a side hustle starts to feel real, and that idea lands well because it follows earlier talk about structure, money-making side hustles, and building while still keeping a nine-to-five.
Straightforward advice on speaking naturally, batching work, and keeping a camera routine sustainable.
Side Hustle Pro treats content creation like a habit, not a mystery. The advice is simple: speak normally, picture one listener, and group a few pieces together on recording days.
The host lets the guard down here.
Mikaela Matthews Okome opens the show by calling out the tax confusion that tends to follow side hustlers into every filing season.
Nikayla is stressed, and she records anyway.
You probably already know enough.
This episode features Chanel Tyler discussing her transition from a corporate executive at YouTube to a full-time creator, sharing insights on building a five-figure passive income through content creation and affiliate marketing while navigating personal challenges like hearing loss.
Host Nikayla Matthews Okome gets coached by business coach D.L.
The money conversation starts where it hurts.
A 12-week reset gives Nikayla some room to breathe.
Host Nicaila Matthews Okome shares five ways to generate income while unemployed, drawing from her own experience after business school.
Host Nicaila Matthews Okome reflects on her biggest podcasting lessons in the 500th episode of Side Hustle Pro.
$1,000 changes the question.
This episode teaches listeners how to start a profitable side hustle while maintaining their current job for financial stability and reduced stress.
Host Nikayla Matthews Okome shares seven side hustles that can generate real income, emphasizing they are viable businesses, not hobbies.
The host shares a 12-week sprint approach for setting and achieving side hustle goals more effectively than traditional annual resolutions.
The host announces she is taking a break due to burnout and replays a podcast swap episode from a client.
This episode features an interview with Trisha Lee, who transitioned from a beauty mogul to a successful real estate titan, discussing her journey and insights on building a profitable side hustle.
What if content felt less robotic?
Host Nicaila Matthews Okome shares her personal journey of rebuilding her business after experiencing burnout, offering insights and strategies for entrepreneurs.
Host Nicaila Matthews Okome discusses nine side hustles that can replace a nine-to-five income, emphasizing strategic problem-solving over viral fame.
This episode features an interview with Dr.
"Do you have enough time?" The guest makes the AI pitch feel plain: entrepreneurs and business owners are short on time, and repeatable tasks need repeatable help.
Kiwa Narula discusses her journey from running a successful kids boutique to becoming a small business strategist, and why she closed her store to build a more impactful career.
Host Nikayla Matthews Okome discusses the importance of mindset for side hustlers, sharing a personal story about confidence and overcoming fear.
Host Nikayla Matthews Okome discusses how to find time for a side hustle while working full-time, identifying time traps and sharing strategies for progress.
The host guides listeners on identifying undervalued skills and turning them into profitable side hustles.
A throwback interview with Demetria Lucas about side hustling, taking risks, and betting on yourself while leveraging career experience.
This episode features an interview with a Black woman entrepreneur who scaled her side hustle into a profitable business, with actionable advice for listeners.
The host shares seven side hustles that can generate income for unemployed or cash-strapped individuals, focusing on leveraging dormant skills.
This episode discusses why podcasts fail to make money and features an interview with a Black woman entrepreneur.
Host Nicaila Matthews Okome interviews Marty McDonald, founder of Boss Women Media and Elle Olivia, about her journey from corporate America to entrepreneurship and empowering Black women.
Host Nikayla Matthews Okome explains why podcasts fail to make money and offers strategies to fix it, drawing from her own experience scaling a side hustle into a full-time business.
Host Nicaila Matthews Okome interviews Portia Oping, a social media strategist and LinkedIn coach, about her journey from side hustler to entrepreneur.
Host Nicaila Matthews Okome shares tips on how to get unstuck mid-year, reflecting on progress and offering actionable strategies for side hustlers.
Host Nicaila Matthews Okome interviews Kareem Edwards, a former Wall Street professional turned entrepreneur, about his journey from side hustle to full-time business.
Host Nicaila Matthews Okome discusses how to make time for a side hustle while working full-time, identifying time traps and sharing strategies to grow a side business.