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Entrepreneurship
Side Hustle
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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

PublishesWeeklyEpisodes525Founded10 years ago
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Artwork for Side Hustle Pro

Latest Episodes

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⭐ APPLY TO SHIFT: sidehustlepro.co/shift

In this solo episode, I'm pulling back the curtain on my entrepreneurial journey and sharing the six most important lessons I've learned si... more

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. Camille is a trafficking survivor who escaped an abusive situation at 21, b... more

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 years rising through the ranks of some of the biggest names in media an... more

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 library in Wilmington, North Carolina. By the time she graduated high scho... more

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Recent Guests

Jessica Lane Alexander
Co-founder of Poppin Creative; former TV One digital/socail leader
Poppin Creative
Episode: 515: From Corporate to Creative: How Jessica Lane Alexander and Lori Hall McKissic Built Pop’N Creative into a $4M Agency
Lori Hall McKissic
Co-founder of Poppin Creative; former Turner and TV production executive
Poppin Creative
Episode: 515: From Corporate to Creative: How Jessica Lane Alexander and Lori Hall McKissic Built Pop’N Creative into a $4M Agency
Janae Young
Founder of Young College Prep (college admissions coach and entrepreneur)
Young College Prep
Episode: 514: From Tutoring Classmates in High School to $1M College Prep CEO w/ Janae Young
Leah Collins
Financial coach, TEDx speaker, host of Own Networks, Maxxed Out
Self-employed/ Own Networks
Episode: 512: How Leah Collins Turned Financial Mistakes Into a TV Show, Multiple Income Streams, and a Purpose-Driven Career
Monica Cornitcher
CEO and co-founder of Medasi Cocktails
Medasi Cocktails
Episode: 511: Monica Cornitcher’s Journey From Personal Loss to Non-Alcoholic Cocktail Success
Monique Shields
Executive coach and host of Ambition Without Compromise
Ambition Without Compromise (podcast) / private coaching
Episode: 510: How I'm Rebuilding After A Hard Season (feat. Monique Shields)
Lisa Greene-Lewis
CPA, TurboTax expert with 20+ years in tax preparation
TurboTax
Episode: 508: The Tax Mistakes Side Hustlers Make That Cost Them Thousands (And How to Avoid Them)
Chanel Tyler
Buy Me Chanel, creator, entrepreneur and former YouTube/Estee Lauder executive
Buy Me Chanel / Creator / Former YouTube executive
Episode: 505: From YouTube Exec to Full-Time Creator: How Chanel Tyler Turned Content Creation Into 5-Figure Passive Income
Dielle Charon
Founder of For the 23% and sales/business/money coach
For the 23%
Episode: 504: How to Go From Side Hustle to $1 Million | My Coaching Session with Dielle Charon

Reviews

4.7 out of 5 stars from 2.1k ratings
  • 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 Statesa month 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 States2 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 States3 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 States4 months ago
  • Thank You & Keep Going and Glowing

    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.... more

    Apple Podcasts
    5
    FordTough213
    United States4 months ago

Listeners Say

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

Listeners praise the host's authenticity, practicality, and inspiring coaching style.
The show is valued for its focus on Black women entrepreneurs and real-world strategies.
Guests and topics are relatable and actionable for turning side hustles into scalable businesses.

Chart Rankings

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

Talking Points

Recent interactions between the hosts and their guests.

515: From Corporate to Creative: How Jessica Lane Alexander and Lori Hall McKissic Built Pop’N Creative into a $4M Agency
Q: What is their guiding advice for women considering leaving a stable job to start their own agency?
Aim for a staged leap by securing contracts that cover at least 60% of your target salary, ensuring you can meet basic needs while still pursuing aggressive growth and avoiding fear-based decisions.
515: From Corporate to Creative: How Jessica Lane Alexander and Lori Hall McKissic Built Pop’N Creative into a $4M Agency
Q: What were the major pivots the business made during the pandemic that enabled growth?
They pivoted from an experiential storytelling model to a social-forward agency, adopting COVID-safe production protocols and emphasizing social video and digital campaigns, which kept projects alive and attracted new clients seeking online/virtual engagement.
515: From Corporate to Creative: How Jessica Lane Alexander and Lori Hall McKissic Built Pop’N Creative into a $4M Agency
Q: How long did it take to land their first client after returning to Atlanta and launching capabilities conversations?
They secured their first engagement by reaching out to former marketing leadership at a Turner property, presenting in LA, and receiving an enthusiastic, immediate invitation to meet; the outcome validated their approach and kickstarted client work.
511: Monica Cornitcher’s Journey From Personal Loss to Non-Alcoholic Cocktail Success
Q: How have personal setbacks affected your business, and what keeps you moving forward?
The passing of Inga was a major setback, but Monica describes leaning on memories, seeking therapy, and maintaining a strategic plan to continue the brand's mission. She emphasizes resilience, ongoing pursuit of retail opportunities, and building a legacy through Medasi Moments on their website.
511: Monica Cornitcher’s Journey From Personal Loss to Non-Alcoholic Cocktail Success
Q: What happened at Expo West, and how did that event shape your path toward retail and VC interest?
Expo West was a deliberate, single-minded push to secure retail and VC attention. They spent a substantial amount to participate, showcased a strong bar-like booth, and engaged with about 50 potential investors, leading to initial conversations with a VC who could fund the next growth stage.

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?

This show spotlights Black women entrepreneurs who turned side hustles into profitable businesses, sharing origin stories, growth strategies, and practical lessons for scaling while balancing life. Episodes frequently cover funding, cash flow, branding, marketing, and the realities of navigating markets as women of color, with a strong emphasis on actionable steps, storytelling, and community support. A notable strength is its focus on resilience, authenticity, and diverse creator journeys, plus a track record of guests who built multi-million dollar ventures from scrappy beginnings. Potential listeners will likely find inspiration and concrete tactics for ideation, launch, and sustainable growth in real-world contexts.

Where can I find podcast stats for Side Hustle Pro?

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How many listeners does Side Hustle Pro get?

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What are the audience demographics for Side Hustle Pro?

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How many subscribers and views does Side Hustle Pro have?

To see how many followers or subscribers Side Hustle Pro has on Spotify and other platforms such as Castbox and Podcast Addict, simply upgrade your account. You'll also find viewership figures for their YouTube channel if they have one.

Which podcasts are similar to Side Hustle Pro?

These podcasts share a similar audience with Side Hustle Pro:

1. Brown Ambition
2. She's So Lucky
3. Hello Seven Podcast
4. Journey To Launch
5. Therapy for Black Girls

How many episodes of Side Hustle Pro are there?

Side Hustle Pro launched 10 years ago and published 525 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?

Our systems regularly scour the web to find email addresses and social media links for this podcast. We scanned the web and collated all of the contact information that we could find in our podcast database. But in the unlikely event that you can't find what you're looking for, our concierge service lets you request our research team to source better contacts for you.

Where can I see ratings and reviews for Side Hustle Pro?

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How do I access podcast episode transcripts for Side Hustle Pro?

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What guests have appeared on Side Hustle Pro?

Recent guests on Side Hustle Pro include:

1. Jessica Lane Alexander
2. Lori Hall McKissic
3. Janae Young
4. Leah Collins
5. Monica Cornitcher
6. Monique Shields
7. Lisa Greene-Lewis
8. Chanel Tyler

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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