489: How to Start a Side Hustle with AI (feat. Nadeen Matthews Blair)
Side Hustle Pro
Nicaila Matthews Okome | Side Hustle Pro Media
4.7 • 1.8K Ratings
🗓️ 19 November 2025
⏱️ 58 minutes
🧾️ Download transcript
Summary
This week in the guest chair, we have someone very special, my sister, Nadeen Matthews Blair and her pivot story is going to speak directly to anyone who’s ever felt called to reinvent themselves.
After 20 years in banking, management consulting, and C-suite leadership, Nadeen hit a point where the titles, the pressure, and the nonstop demands were no longer aligned with the life she wanted for herself and her family. So she did what so many high-achieving women fear doing: she stepped back, listened to the whisper, and chose a new path.
That path led her to Crescent Advisory Group, where she now teaches professionals, creatives, and new entrepreneurs how to use AI with confidence. What’s wild is that she built the entire business using just four beginner-friendly AI tools and today, she’s breaking them all down for you.
Whether you’re in a pivot, launching a side hustle, or trying to understand where AI fits into your next chapter, this episode will give you clarity, confidence, and a simple starting point.
In This Episode, Nadeen Shares:
- How she pivoted from a demanding corporate career into full-time entrepreneurship
- Why early consulting and workshop opportunities found her before she officially launched
- How AI tools like Perplexity, Gamma, Looka, and Namelix helped her build her brand, website, and business foundation fast
- Why AI is the most powerful leverage tool for side hustlers in 2025
- How redefining success around flexibility, family, and purpose shaped her new chapter
- What she’s teaching thousands of people in her beginner-friendly AI webinars
If you’ve been feeling the pull to pivot or you’re curious about how to use AI without feeling overwhelmed, this is your episode.
Watch Episode 489 on YouTube and listen on all podcast apps.
Links mentioned in this episode
Crescent Advisory Group: http://crescentadvisorygroup.com
ChatGPT
Perplexity
NameLix
Gamma
Lovable
MIT AI Courses
Alicia Little’s AI Innovation Program
Guest Social Media Info
Side Hustle Pro – @sidehustlepro: https://www.instagram.com/sidehustlepro/
Nadeen Matthews Blair IG: https://www.instagram.com/nadeenmatthewsblair/
Nadeen Matthews Blair LinkedIn: https://www.linkedin.com/in/nadeenmatthews/
Hosted on Acast. See acast.com/privacy for more information.
Transcript
Click on a timestamp to play from that location
| 0:00.0 | Why do you believe AI is so critical right now for entrepreneurs and business owners? |
| 0:04.7 | So I've never heard anybody say that they have enough time. Have you? Nope. |
| 0:11.0 | Do you have enough time? Absolutely not. |
| 0:15.5 | You're listening to Side Hustle Pro, the podcast that teaches you to build and grow your side hustle from |
| 0:22.0 | passion project to profitable business. And I'm your host, Nikaela Matthews Okome. So let's get |
| 0:28.0 | started. |
| 0:32.5 | Hey, hey, friends. It's Nikaela. Welcome or welcome back to my channel. Today in the guest chair, |
| 0:38.1 | I'm sitting down with someone incredibly special to me, my oldest sister, Nadine Matthews Blair. |
| 0:43.7 | And we're breaking down what I'm calling the AI starter kit, the four simple AI tools she used |
| 0:49.2 | to launch her business from scratch. Nadine spent over 20 years in banking, consulting, and the C-Suite before |
| 0:55.2 | making this major pivot into AI education and executive coaching. Now she teaches business |
| 1:00.9 | owners, employees, and entrepreneurs how to use AI without overwhelm. And today, she's walking |
| 1:06.4 | us through the exact tools she used and recommends for any new side hustler who wants to launch faster and |
| 1:11.6 | with more clarity. So if you've been curious about AI or you're in a pivot of your own and want to |
| 1:16.7 | understand where to begin and how to get started faster, this is your episode. Let's jump in. |
| 1:27.1 | All right, all right, sis Nadine, welcome to the guest chair. |
| 1:32.2 | Thank you, sis. |
| 1:33.5 | I am so excited to be interviewed by my... |
| 1:38.1 | I know. |
| 1:41.3 | I can't believe we're doing this, but I decided I had to share one of my best kept |
| 1:46.8 | secrets with the world at last, which is my big sister, who I'm able to tap into for anything |
| 1:55.0 | really. And now as an entrepreneur and someone who is an expert in AI has been really, really critical. |
... |
Please login to see the full transcript.
Disclaimer: The podcast and artwork embedded on this page are from Nicaila Matthews Okome | Side Hustle Pro Media, and are the property of its owner and not affiliated with or endorsed by Tapesearch.
Generated transcripts are the property of Nicaila Matthews Okome | Side Hustle Pro Media and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.
Copyright © Tapesearch 2026.