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

23/10/2025 31 min Episodio 24
Craig J. Lewis | 750K Contractors Paid, $25M Raised, MassChallenge Board - From Gig Wage to Ogentic AI

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Episode Synopsis


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 EraWhere to find Craig J. Lewis:Linkedin: https://www.linkedin.com/in/mrfutureofworkX: https://x.com/CraigJamalLewis Instagram: https://www.instagram.com/craigjlewisWhere to find Ogentic AI: Website: https://ogenticai.comLinkedIn: https://www.linkedin.com/company/ogenticaiX: https://x.com/ogenticai Instagram: https://www.instagram.com/ogenticai‍Where to find David Phillips:‍X: https://x.com/davjLinkedIn: https://www.linkedin.com/in/davjphillipsBrought to you by:Fondo — All-in-one accounting for startups: https://fondo.com

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