Side Hustle Pro 489: How to Start a Side Hustle with AI (feat. Nadeen Matthews Blair)
Nov 19, 2025
Nadeen Matthews Blair, founder of Crescent Advisory Group and former corporate executive, shares her transformative journey from the corporate world to entrepreneurship. She emphasizes the power of AI tools like ChatGPT, Namelix, and Looka in building a business quickly. Nadeen discusses how offering free workshops helped validate her services and highlights AI as a game changer for side hustlers. She also reflects on redefining success to prioritize flexibility and impact while encouraging others to engage with technology constructively.
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Career Pivot Into AI Education
- Nadeen pivoted from 20+ years in banking, McKinsey, and C-suite leadership into AI education and entrepreneurship.
- She registered Crescent Advisory Group in 2023 and began getting workshop requests before officially launching in 2024.
Learning Break Led To Early Clients
- While on a break after restructuring, Nadeen studied generative AI via MIT and other courses and began writing on LinkedIn.
- Her side-work teaching AI grew from DMs and workshop invites while she was home caring for family.
Validate Offers With Free Workshops
- Validate side-hustle ideas by offering free workshops or training to build credibility and references.
- Use those early, low-cost engagements to gather feedback and test demand before charging.
