Side Hustle Pro
Hosted by Side Hustle Pro
A podcast profiling Black women entrepreneurs who have successfully scaled their side hustles into profitable, full-time businesses.
A weekly show that alternates between two formats: long-form interviews with Black women founders about their journey from side project to CEO, and solo episodes where host Nicaila Matthews Okome shares lessons from her own entrepreneurial path. The interviews dig into origin stories, business strategy, and personal resilience, while the solo shows offer practical advice on topics like monetization, mindset, and knowing when to quit your day job.
“Its tight focus on the journeys of Black women entrepreneurs is its core distinction, offering a platform for stories often underrepresented in the mainstream business media. The host’s transparency about her own process in solo episodes creates a strong, relatable connection with her audience.”
Who hosts this show
Side Hustle Pro is the first and only podcast to spotlight bold, Black women entrepreneurs who have scaled from a side hustle to a profitable business. The show is hosted by Nicaila Matthews Okome, a marketer and entrepreneur who chronicled her own journey from side hustler to full-time business owner. In a mix of solo episodes and guest interviews, she provides actionable strategies for listeners to start and grow their own ventures.
Credentials & credits
- MBA, University of Michigan
- BA, University of Pennsylvania
- Podcast Hall of Fame Inductee (2022)
- Featured as "Side Hustle Expert" on the TODAY show
- Former digital marketing/social media strategist for NPR, Google, and MTV Networks
- Writer for Entrepreneur Magazine
Other ventures
- Podcast Moguls (coaching program)
- Shift (coaching program)
- 6-Bullet Saturday (newsletter)
- 1-on-1 Podcast Coaching
What kind of podcast
When new episodes drop
- 01After 10 Million Downloads, Here’s What I LearnedJun 20, 2026 · 26 min
- 02The ONE skill you need to learn before you QUITJun 12, 2026 · 30 min
- 03After Quitting My $100K Job to Launch My Own Business—Here’s What I LearnedJun 5, 2026 · 26 min
- 04From Caregiver to CEO: How Camille Joy Turned Her Son’s Diagnosis Into a MovementMay 29, 2026 · 1h 00m
- 05
- 06From Tutoring Classmates in High School to $1M College Prep CEO w/ Janae YoungMay 15, 2026 · 1h 16m
- 07Tiffany Aliche on What the Hard Years Teach You About Money and ResilienceMay 8, 2026 · 1h 07m
- 08
Notable episodes
- 01After 10 Million Downloads, Here’s What I Learned
A milestone solo episode where the host reflects on her podcasting journey, sharing key lessons about the value of podcasting beyond metrics.
- 02After Quitting My $100K Job to Launch My Own Business—Here’s What I Learned
A foundational solo episode where the host details her own origin story, the risks she took, and the core philosophies that guide the show.
- 03From Caregiver to CEO: How Camille Joy Turned Her Son’s Diagnosis Into a Movement
A powerful guest interview that exemplifies the show's mission, showcasing a story of overcoming immense personal hardship to build a business and movement.
What you'll be asked on this show
Nicaila opens interviews by establishing the guest's origin story, often using phrases like "Let's go back to..." to explore their life before their current business. She actively listens for key moments in a guest's narrative—a past career, a personal challenge, a major pivot—and probes deeper to uncover the lessons within. Throughout the conversation, she summarizes the guest's points, reframing them as actionable takeaways for the audience. The interview consistently concludes with a fast-paced "Lightning Round" that asks for specific resources and parting advice.
The show is a mix of solo, lesson-driven episodes and guest interviews. In solo episodes, the host is encouraging and transparent, often using her own experiences as case studies. Interviews are structured but conversational, designed to extract a guest's full journey from origin to success, concluding with a signature "Lightning Round" of rapid-fire questions.
Questions Side Hustle Pro keeps coming back to
12 cataloguedIf you're going on this show as a guest, expect some version of each of these. Each note explains when Side Hustle Pro reaches for it.
origin
1- Q.01
“Before your business, what did life look like and when did you realize you needed to create this?”
This is a standard opening question to establish the guest's origin story and the initial spark for their venture.
backstory
1- Q.01
“Let's go back to your previous career. Was that always your intended path?”
The host uses this to explore a guest's professional background before they became an entrepreneur.
process
1- Q.01
“Once you decided to leave your job, what did you do next? Did you have a plan?”
This question probes the critical transition from employee to full-time entrepreneur.
business
1- Q.01
“When you first launched your podcast or project, did you think it would become your business?”
She asks this to understand the initial intent behind the side hustle and when the mindset shifted.
money
1- Q.01
“How did you start to figure out your revenue streams to take care of your household?”
This is a direct question to get practical details on the guest's monetization strategy.
technique
1- Q.01
“What kind of content were you creating on social media that started to get traction?”
This question seeks to uncover the specific content and marketing tactics that helped the guest grow.
mindset
1- Q.01
“How did you get to a place where you could help others while also navigating your own challenges?”
The host asks this to explore the guest's mindset and capacity for building a community.
personal
1- Q.01
“What supports do you have in place in your family or team to help you?”
Asked near the end, this question explores the personal and professional support systems behind the entrepreneur.
advice
3- Q.01
“What's something you wish the world understood about building a business while [caregiving/etc.]?”
This question is tailored to the guest's specific life circumstances to elicit unique advice.
- Q.02
“What is a resource that has helped you in building your business?”
This is a recurring question from the signature 'Lightning Round' to provide a tangible tool for listeners.
- Q.03
“What is your parting advice for entrepreneurs worried about not having a steady paycheck?”
This is a common final question in the 'Lightning Round' to address a core fear of the audience.
craft
1- Q.01
“Can you share more about your book/product, what it's about, and who it helps?”
The host provides a clear opportunity for the guest to promote their own products or services.
Signature segments
- · Lightning Round
- · Hey friends, hey, welcome, welcome back to the show.
- · 6-Bullet Saturday newsletter
Topics covered repeatedly
Who gets booked here
Guests are exclusively Black women entrepreneurs who have successfully transformed a side hustle into a profitable business. They often come from a variety of industries and have compelling, resilient backstories of overcoming personal or professional challenges to build their companies.
- Camille Joyon From Caregiver to CEO: How Camille Joy Turned Her Son’s Diagnosis Into a Movement
- Jessica Lane Alexanderon How Jessica Lane Alexander and Lori Hall McKissic Built Pop’N Creative into a $4M Agency
- Lori Hall McKissicon How Jessica Lane Alexander and Lori Hall McKissic Built Pop’N Creative into a $4M Agency
- Janae Youngon From Tutoring Classmates in High School to $1M College Prep CEO w/ Janae Young
- Tiffany Alicheon Tiffany Aliche on What the Hard Years Teach You About Money and Resilience
- Leah Collinson How Leah Collins Turned Financial Mistakes Into a TV Show & Multiple Income Streams
Where to find this show
Audience & reach
The podcast primarily promotes the host's own coaching programs, such as 'Shift' and 'Podcast Moguls'. Evidence also shows the host has secured external brand sponsorships, suggesting a mix of internal and external monetization.
Subscriber and view counts are pulled live from YouTube and re-verified on a 30-day cycle. Listener estimates for the RSS feed aren't published here unless they're host-verified.
Pitch Side Hustle Pro
People also ask
- What is the host's real name?
- The host's name is Nicaila Matthews Okome.
- What is Side Hustle Pro about?
- It's a podcast that spotlights and interviews Black women entrepreneurs who have successfully scaled a side hustle into a profitable, full-time business.
- What is the show's format?
- The show alternates between solo episodes where the host shares her own business lessons and long-form interviews with guest entrepreneurs.
- Is the podcast still active?
- Yes, the podcast releases new episodes on a weekly basis.
- How can I be a guest on the podcast?
- There is a guest application form available on the official Side Hustle Pro website.
- Where can I listen to the podcast?
- Side Hustle Pro is available on its official website, YouTube, Apple Podcasts, iHeartRadio, and other major podcast platforms.
Built from the show's public RSS feed, YouTube, the host's own websites, and the cited sources below. Computed and AI-extracted fields are labelled. Facts only — no private info, no fabrication, no transcripts republished.
Sources & how this page was built
This page is AI-assisted, grounded in the public sources cited below, and host-verifiable. We publish facts only; we do not republish transcripts. If anything here is wrong, the host can claim and correct the page above.Model: gemini-2.5-pro · high confidence
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