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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 entrepr... more

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Latest Episodes

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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 ba... more

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 an... more

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 f... more

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 e... more

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Recent Guests

Karen Young
Founder and CEO of OUI the People
OUI the People
Episode: How Karen Young Built OUI the People
Busayo Olupona
Founder and creative director of Busayo, a Brooklyn-based fashion brand rooted in Nigerian textile dyeing
Busayo
Episode: She Left Corporate Law, Went Back to Work, and Still Built a Global Fashion Brand
Chrishon Lampley
Founder and CEO of Love Corkscrew; creator of The Lampley wine line
Love Corkscrew
Episode: How Her Wine Became the Obama Presidential Center’s Official White Wine
Dawn Fitch
Founder and CEO of Pooka Pure and Simple
Pooka Pure and Simple
Episode: Why She Pulled Her Brand Out of Whole Foods After 26 Years | Dawn Fitch, Founder of Pooka Pure and Simple
Roxana Couse
The Millennial Manager, former corporate professional turned content-creator and founder of SlowFi
SlowFi (platform founder)
Episode: How Roxy Couse Replaced Her Corporate Title With Her Personal Brand
Jamila Wright
Co-founder of Brookyn Tea
Brookyn Tea
Episode: She Emptied Her Retirement to Open a Tea Brand (Jamila Wright, Founder of Brookyn Tea)
Cynthia Bailey
Former model and reality TV star turned entrepreneur, co-founder of Glowissima
Glowissima
Episode: How Real Housewives of Atlanta's Cynthia Bailey and Co-Founder Dana Hill-Robinson Built Glowissima Skincare
Dana Hill-Robinson
Founder of Cocotique, beauty industry executive, co-founder of Glowissima
Glowissima
Episode: How Real Housewives of Atlanta's Cynthia Bailey and Co-Founder Dana Hill-Robinson Built Glowissima Skincare
Jotaka Eaddy
Founder of Win With Black Women, founder of Full Circle Strategies
Win With Black Women / Full Circle Strategies
Episode: 520: How Jotaka Eaddy Built a Movement of 44,000 Black Women Overnight

Host

Nicaila Matthews Okome
Host of the show, chief strategy and on-air interviewer guiding founder-focused conversations.

Reviews

4.7 out of 5 stars from 2.1k ratings
  • Deep Bow

    Ndewo...Deep Bow...Busayo...Daalụ...Ama

    Apple Podcasts
    5
    Amarachi Mgbeke
    United States15 days ago
  • Authenticity is magic

    I recently found the show. I love the real and honest conversations surrounding work, business, and life.

    Apple Podcasts
    5
    blinky02jd
    United States4 months ago
  • Very thoughtful and relatable content

    Nicaila, thank you for your honesty and transparency in your podcast. Whenever I am able to stop and listen to your podcast, you always provide me with such inspiration and a way forward. I am a mom, wife, full time employee who has all the aspirations of creating a profitable side hustle and your content consistently provides me with great insight to just take that first step and do it! Just want to say I truly appreciate your voice and please continue your awesome work!

    Apple Podcasts
    5
    A-Star8
    United States5 months ago
  • Love this podcast

    Side Hustle Pro is the best career, business and life advice show that is practical and actionable all delivered with Nicaila’s warm, encouraging and thoughtful demeanor.

    Apple Podcasts
    5
    Really Really Really Rich
    United States5 months ago
  • So happy I found this podcast

    I was down in the dumps about getting laid off am stumbled on this podcast. It was kismet. Nicaila’s advice on how brand yourself and take the skills you learned in your previous role to help leverage your next role was just want I needed to get myself out there! Thank you for this episode and this show.

    Apple Podcasts
    5
    akey618
    United States6 months ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Many praise the guests for diverse experiences and tangible lessons.
Listeners appreciate transparent, relatable host with practical takeaways.
Fans love the authentic, actionable advice and real-world stories.
Some critique occasional interruptions during interviews.

Chart Rankings

How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.

Talking Points

Recent interactions between the hosts and their guests.

How Karen Young Built OUI the People
Q: How did you approach your next idea after the Razorburn venture, given everything you learned from the first attempt?
Karen describes iterative development, starting with products she'd use herself and testing with a careful approach to margins and pricing. She highlights learning from margins, testing with small runs, and using the knowledge from Estee Lauder to build a scalable body-care line that extended beyond shaving.
How Karen Young Built OUI the People
Q: When did you decide to leave Estee Lauder and go full-time, and what were the signals that told you it was the right move?
She notes that crossing the six-figure mark and achieving profitability while maintaining a strong runway of cash flow gave her the confidence to go all-in, supported by market validation, a grant win, and a belief in the product's ability to shift consumer behavior.
How Karen Young Built OUI the People
Q: You started with a Razorburn problem and talked about your origins. Walk us through how that frustration became a business idea and what you learned along the way.
Karen explains that the Razorburn pain point led to a shift from a broader grooming focus to a safety razor for women, and that her background in design, sourcing, and beauty allowed her to craft a differentiated product. She emphasizes learning from early missteps, leveraging editor PR, and building a story around belonging for melanated skin to create a differentiated, premium offering.
Why She Pulled Her Brand Out of Whole Foods After 26 Years | Dawn Fitch, Founder of Pooka Pure and Simple
Q: What advice would you give to someone considering a big-box retailer?
Don't move too early; ensure you have solid numbers, trademarks, and the capacity to sustain online and wholesale channels if the retailer underperforms or requires returns management.
Why She Pulled Her Brand Out of Whole Foods After 26 Years | Dawn Fitch, Founder of Pooka Pure and Simple
Q: What role does Bloom Bar play in your business model?
Bloom Bar created an experiential draw that brought new customers into the store, boosting product sales and creating a reason for people to visit beyond purchasing products.

Audience Metrics

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Frequently Asked Questions About Side Hustle Pro

What is Side Hustle Pro about and what kind of topics does it cover?

Gathers practical, founder-focused insights from Black women entrepreneurs who started as side hustles and scaled to sustainable businesses. Episodes emphasize real-world hurdles—bootstrapping, wholesale, branding, fundraising, and balancing health and growth—along with actionable tactics like niche positioning, distribution strategies, and personal branding. Guests span fashion, beauty, food & beverage, tech-enabled services, and social impact, providing a mix of inspirational origin stories and concrete takeaways for listeners aiming to turn passion into profitable ventures. A standout angle is the emphasis on resilience, community-building, and mentorship, with conversations often weaving in ownership, authenticity, and spirituality as d... more

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Which podcasts are similar to Side Hustle Pro?

These podcasts share a similar audience with Side Hustle Pro:

1. Brown Ambition
2. Hello Seven Podcast
3. She's So Lucky
4. Journey To Launch
5. Social Proof Podcast

How many episodes of Side Hustle Pro are there?

Side Hustle Pro launched 10 years ago and published 537 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

How do I contact Side Hustle Pro?

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What guests have appeared on Side Hustle Pro?

Recent guests on Side Hustle Pro include:

1. Karen Young
2. Busayo Olupona
3. Chrishon Lampley
4. Dawn Fitch
5. Roxana Couse
6. Jamila Wright
7. Cynthia Bailey
8. Dana Hill-Robinson

To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.

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