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:
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
Where to find David Phillips:
LinkedIn: https://www.linkedin.com/in/davjphillips
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Fondo — All-in-one accounting for startups: https://fondo.com