Craig J. Lewis | 750K Contractors Paid, $25M Raised, MassChallenge Board - From Gig Wage to Ogentic AI

Craig Lewis is the Founder & CEO Ogentic AI, builder of Zing—an AI-native enterprise browser that turns intent → action in a secure, workflow-native workspace. Before Ogentic, he founded Gig Wage (750k contractors paid, ~$1B moved, $25M+ raised) and learned payroll inside ADP. That operator muscle fuels Ogentic’s pace: incorporated in June, alpha in July, beta in August. He also serves on the governing board at MassChallenge and angels actively.

In this episode, Craig shares velocity advice like: ship before perfect (feedback > stealth), build pro-human AI (human-in-the-loop), and treat fundraising like sales (expect 19 no’s, optimize investor–founder fit, when it’s right—TTFM). He outlines the back-office stack that keeps your startup in good shape and his board philosophy: offer perspective, not prescriptions. If you’re building enterprise AI—or just want to move in weeks, not quarters—this one’s for you.

Key Topics Covered:

• Ogentic AI focuses on enterprise productivity and automation.
• Building a strong back office is crucial for startups.
• Fundraising is a numbers game; persistence is key.
• Feedback is essential for product development.
• AI will replace some jobs but also create new ones.
• Having a technical co-founder can accelerate growth.
• Navigating the fundraising landscape requires understanding investor fit.
• MassChallenge supports entrepreneurs in solving global challenges.
• The future of work will involve augmenting human capabilities with AI.
• Startups should find their niche in the AI market.

Chapters

(00:00) The Rise of Ogentic AI

(13:37) Building a Strong Back Office

(17:02) Navigating Fundraising Challenges

(19:14) The Role of MassChallenge

(23:12) AI and the Future of Work

(27:40) Fundraising in the AI Era

Where to find Craig J. Lewis:

Linkedin: https://www.linkedin.com/in/mrfutureofwork

X: https://x.com/CraigJamalLewis 

Instagram: https://www.instagram.com/craigjlewis

Where to find Ogentic AI:

 
Website: https://ogenticai.com
LinkedIn: https://www.linkedin.com/company/ogenticai
X: https://x.com/ogenticai
Instagram: https://www.instagram.com/ogenticai

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Where to find David Phillips:
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X: https://x.com/davj

LinkedIn: https://www.linkedin.com/in/davjphillips

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