This is a free preview of a premium episode. To subscribe to Down Round Premium and get access, head here.

Dropbox. There's a name you probably haven't thought about in a while. Once among the hottest startups on Earth, it lost some of its lustre once every major company in the world began offering consumer and enterprise cloud storage. But it's still alive, kicking and profitable – and making a pivot to AI.

In this ep, we talk about Dropbox and the other cloud storage businesses of the 2000s and 2010s, and why they're between a rock and a hard place.

See omnystudio.com/listener for privacy information.