Side Hustle Pro artwork

Entrepreneurship · Nicaila Matthews Okome | Side Hustle Pro Media

Side Hustle Pro

by Nicaila Matthews Okome | Side Hustle Pro Media

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.

Latest episodes

Showing 20 · updated from the feed

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

#38 trending · Entrepreneurship

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,

Sep 18
53 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 n

Sep 11
33 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,

Aug 28
1 h 09 min

How Karen Young Built OUI the People

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 hai

Aug 21
1 h 14 min

She Left Corporate Law, Went Back to Work, and Still Built a Global Fashion Brand

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 textil

Aug 14
1 h 11 min

How Her Wine Became the Obama Presidential Center’s Official White Wine

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 nationall

Aug 7
51 min

7 Things I Had to Unlearn Before Leaving My Corporate Job

If this resonated with you, here are additional resources: ⭐ APPLY TO SHIFT: https://sidehustlepro.co/shift In this episode, I'm sharing the seven beliefs I had to unle

Jul 31
43 min

Why She Pulled Her Brand Out of Whole Foods After 26 Years | Dawn Fitch, Founder of Pooka Pure and Simple

If this resonated with you, here are additional resources: ⭐ APPLY TO SHIFT: https://sidehustlepro.co/shift In this episode, I sat down with Dawn Fitch, founder of Pook

Jul 30
52 min

How Roxy Couse Replaced Her Corporate Title With Her Personal Brand

If this resonated with you, here are additional resources: ⭐ APPLY TO SHIFT: https://sidehustlepro.co/shift In this episode, I sat down with Roxy Couse, the creator beh

Jul 24
49 min

She Emptied Her Retirement to Open a Tea Brand (Jamila Wright, Founder of Brookyn Tea)

If this resonated with you, here are additional resources:  APPLY TO SHIFT: https://sidehustlepro.co/shift In this episode, I sat down with Jamila Wright, co-founder of

Jul 17
1 h 00 min

How Real Housewives of Atlanta's Cynthia Bailey and Co-Founder Dana Hill-Robinson Built Glowissima Skincare

If this resonated with you, here are additional resources: ⭐ APPLY TO SHIFT: https://sidehustlepro.co/shift In this episode, I sat down with longtime friends and busine

Jul 14
1 h 02 min

520: How Jotaka Eaddy Built a Movement of 44,000 Black Women Overnight

If this resonated with you, here are additional resources: ⭐ APPLY TO SHIFT: https://sidehustlepro.co/shift In this episode, I sat down with Jotaka Eaddy, founder of Fu

Jul 7
1 h 03 min

519: After 10 Million Downloads, Here’s What I Learned

If this resonated with you, here are additional resources: ⭐ APPLY TO SHIFT: https://sidehustlepro.co/shift When I launched Side Hustle Pro, I thought success would be

Jun 20
25 min

518: The ONE skill you need to learn before you QUIT

If this resonated with you, here are additional resources: ⭐ APPLY TO SHIFT: https://sidehustlepro.co/shift In this solo episode, I am getting real with you about the

Jun 12
30 min

517: After Quitting My 6-Figure Job to Launch My Own Business Here’s What I Learned

If this resonated with you, here are additional resources: ⭐ APPLY TO SHIFT: https://sidehustlepro.co/shift In this solo episode, I'm pulling back the curtain on my en

Jun 5
26 min

516: From Caregiver to CEO: How Camille Joy Turned Her Son’s Diagnosis Into a Movement

In this episode, I sat down with Camille Joy, founder of the Moments of Joy Podcast and author of Moments of Joy: 90 Days of Encouragement, published by Penguin Random Ho

May 29
1 h 00 min

515: From Corporate to Creative: How Jessica Lane Alexander and Lori Hall McKissic Built Pop’N Creative into a $4M Agency

In this episode, I sat down with the powerhouse duo behind Pop’N Creative, Jessica Lane Alexander and Lori Hall McKissic. These two met years ago at Turner Broadcasting a

May 22
59 min

514: From Tutoring Classmates in High School to $1M College Prep CEO w/ Janae Young

In this episode, I sat down with Janae Young, founder and CEO of Young College Prep, who started her first business at just 15 years old, tutoring classmates out of her s

May 15
1 h 16 min

513: Tiffany Aliche on What the Hard Years Teach You About Money and Resilience

This week in the guest chair is Tiffany Aliche, known to millions as the Budgetnista and the author of the New York Times bestseller Get Good With Money. Tiffany is back

May 8
1 h 06 min

512: How Leah Collins Turned Financial Mistakes Into a TV Show, Multiple Income Streams, and a Purpose-Driven Career

This week in the guest chair is Leah Collins, financial coach, speaker, and host of Maxxed Out, a powerful series helping people confront their finances and the relations

May 1
43 min

Chart trend

Position in the Entrepreneurship chart (US), last 90 days.

#39
all-time peak
38
days in the top 50 since Nov 2024

Chart positions

Where Side Hustle Pro ranks today in each Apple Podcasts chart (US, Sep 21, 2026).

#79 ▲ 22 Entrepreneurship US

What listeners say

A curated, balanced selection of Apple Podcasts reviews.

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!

A-Star8 · Mar 2026

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.

Really Really Really Rich · Mar 2026

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.

akey618 · Feb 2026

This has hands-down been one of my most favorite podcast. I have enjoyed listening since early 2025. I was not a big podcast listener before I found your show. I appreciate your humble transparency, and overall relatable content. It could be that this podcast met me where I was at the moment, in transition, trying to figure out if corporate America or entrepreneurship was my lane. This podcast helped bring not only clarity, but courage to my journey. Thank you so much for the consistent content. I am a CX enthusiast, so shame on me for waiting so long to write my review.

FordTough213 · Jan 2026

We strive to present a balanced view by showing a diverse range of reviews from Apple Podcasts.

More podcasts like Side Hustle Pro

Popular shows in Entrepreneurship, for your next listen.

Browse charts by category

Daily updated Apple Podcasts rankings for the United States.

About Side Hustle Pro on Reason.fm

Here you find the Apple Podcasts chart positions of Side Hustle Pro, its latest episodes to listen to directly, and reviews from listeners. Rankings are updated daily for the United States.

Contact

Questions or issues? Reach us at hello@reason.fm

0:000:00