For nearly two decades, Box co-founder and CEO Aaron Levie has been at the frontlines of how technology reshapes work—guiding the company through the rise of mobile, the cloud, and now the age of AI.
In his fireside with YC General Partner David Lieb at AI Startup School, Aaron reflects on what it means to adapt a company over the long term, the hard lessons of staying relevant across multiple technology waves, and why he believes AI represents the most transformative shift yet.
Chapters:
00:00 – AI hype vs. reality inside companies
01:00 – Early days: starting Box in 2005
03:30 – Pivoting from consumer storage to enterprise cloud
05:45 – Cloud transition lessons vs. AI today
07:10 – Why unstructured data is AI’s biggest opportunity
09:05 – Will AI replace jobs or create more work?
13:15 – Startups vs. incumbents in the AI era
15:20 – Finding the next “nouns and verbs” for startups
20:25 – Rethinking SaaS business models for AI agents
27:05 – Why companies won’t just build everything in-house
31:15 – Advice to young founders
35:40 – Fulfillment and meaning of life
36:40 – Enterprise design and craft in SaaS
39:00 – Competing with incumbents like Workday
