Navigating Life's Questions and the Importance of Design in Enterprise

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.