Side Hustle Pro cover art

Podcast

Side Hustle Pro

537 episodesLatest Aug 28, 2026
Recorded in United States of AmericaAbout the Black AmericanEnglishBusinessEntrepreneurshipMarketing
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.

Episodes

  1. 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, creator, an…

    01:09:20
  2. 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 hairs. Karen…

    01:14:01
  3. 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 textiles created…

    01:11:27
  4. 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 nationally distribu…

    51:33
  5. 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 unlearn before…

    43:40
  6. 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 Pooka Pure and…

    52:12
  7. 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 behind Millenn…

    49:42
  8. 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 Brooklyn T…

    01:00:11
  9. 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 business partners…

    01:02:15
  10. 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 Full Circle S…

    01:03:42
  11. 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 measured…

    25:47
  12. 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 one skill…

    30:12
  13. 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 entrepreneur…

    26:05
  14. 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 House. Camil…

    01:00:33
  15. 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 and spent y…

    59:47
  16. 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 school libr…

    01:16:23
  17. 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 for a deep…

    01:06:49
  18. 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 relationships tied…

    43:39
  19. 511: Monica Cornitcher’s Journey From Personal Loss to Non-Alcoholic Cocktail Success

    I sat down with Monica Cornitcher, CEO and co-founder of Medase Cocktails, a premium non-alcoholic beverage brand redefining what it means to drink without alcohol. What started as…

    43:42
  20. 510: How I'm Rebuilding After A Hard Season (feat. Monique Shields)

    In this episode, I’m joined again by Monique Shields, and this conversation felt like therapy, coaching, and truth-telling all in one. We went deep into something I’ve personally b…

    49:49
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