For nearly two decades, Box co-founder and CEO Aaron Levie (@levie) has been at the forefront of how technology is reshaping the way work gets done, leading the company through the mobile, cloud, and now AI eras. In this conversation with YC's @dflieb at AI Startup School, Aaron reflects on how to position a company for long-term growth, how to remain competitive across multiple waves, and why he believes AI is the most transformative change yet. 00:00 – AI Hype vs. Internal Reality 01:00 – The Early Days: Founding Box in 2005 03:30 – From Consumer Storage to the Enterprise Cloud 05:45 – Lessons Learned from the Cloud Transformation and Today's AI 07:10 – Why Unstructured Data is AI's Biggest Opportunity 09:05 – Will AI Displace or Create Jobs? 13:15 – Startups vs. Incumbents in the Age of AI 15:20 – Finding the Next “Nouns and Verbs” for Startups 20:25 – Rethinking the SaaS Business Model for AI Agents 27:05 – Why Companies Won’t Build All Features In-House 31:15 – Advice for Young Founders 35:40 – Fulfillment and Meaning in Life 36:40 – Enterprise Design and Craft in SaaS 39:00 – Competing with Incumbents