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Hacking the CEO Job: Drew Houston on Reinvention and Leadership

Leadership Next
Leadership Next
Episode • Jun 3 • 54m

In this episode, Dropbox founder and CEO Drew Houston joins Leadership Next to share how he's reimagining work in the age of AI. He traces Dropbox’s evolution—from solving file-syncing in the early cloud era to launching Dropbox Dash, a new AI-powered search and knowledge-management tool. Houston reflects on the hard lessons from failed ventures into email and photo apps, the pressures of self-disruption, and what it takes to stay relevant in a crowded productivity space. He also opens up about distributed work, leadership growth, and the books and mentors that have shaped his journey toward becoming a “bionic CEO.” 

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