Steve Jobs famously told Houston his startup was “a feature, not a product” when trying to acquire it back in 2009. Houston turned down the nine-figure buyout offer and Apple went on to launch iCloud. Houston, now 43 and worth about $2 billion, leaves behind a service used by millions worldwide. He now wants to do something entrepreneurial with — you guessed it — AI. [Link: Dropbox CEO Drew Houston to step down after 19 years at helm of cloud storage pioneer | https://www.cnbc.com/2026/05/26/dropbox-ceo-drew-houston-ashraf-alkarmi.html | CNBC]

Dropbox CEO Drew Houston, who started the cloud storage company when he was 24, plans to step down and assume the role of executive chairman.

Ashraf Alkarmi, promoted from general manager, will serve as co-CEO before eventually becoming sole chief executive