They successfully built their core product and got it to the point where it only had long-tail improvements and maintenance left to do, but even if it didn’t have the complication of being VC funded you can’t really lay off half the company and declare yourself in maintenance mode once you’ve scaled up.

Basically every big corp implemented their own cloud storage, so they had to compete by adding extra features I would guess? I’m still happy customer for personal needs since I’ve had it for ages and too lazy to switch. But when it comes to work needs, it would be a hard sell. If you’re a corp you probably have everything integrated with Microsoft or Google. If all of your devices are Apple, you can just go with iCloud and not deal with 3rd party integrations. At the end of the day, you’re left off with less number of potential customers, and even then you have to fight with Box for customers.

Probably had to stoke that VC-fire once growth leveled off and add new "billion dollar ideas".

Might have been around the time they stopped focusing on users and tried to embed themselves in the National security state. I guess around 2014 when Condoleezza Rice joined the board of directors.