Dropbox CEO Drew Houston to step down

Post by fist » Tue, May 26, 2026, 8:34 PM UTC

bhouston wrote: post #124

Dropbox's stock has been stuck at around $6B valuation for years with flat growth and income around $2.5B per year. It is just stuck. Box.com, which is quite similar, is not that different. Around $3B and $1.2B in income. Similar valuation. I think it is the market, not the leadership. It is a tough market that has cut off the consumer end because all the big players have their own deeply integrated solutions: Apple…

Post by 0cf8612b2e1e » Tue, May 26, 2026, 8:36 PM UTC

dingaling wrote: post #114

tptacek wrote: post #85

Earlier quoted context omitted.

Important to note here that Dan has been for years asking people to understand this comment in the context of the time and circumstances it was written. It's not a dunk on Dropbox. It's not the "less space than a Nomad" iPod comment on Slashdot. It was helpful and constructive criticism for Houston's YC application --- very specifically the application itself. https://hn.algolia.com/?dateRange=all&page=0&prefix=true&…

> "less space than a Nomad" I actually thought that was a valid comment, more so than the Dropbox one. The contemporaneous iPod _was_ technically and acoustically inferior to the Nomad. The iPod "won" on account of fashion, style and marketing. Yes, the Slashdot comment was naive in underestimating or ignoring the power of Apple, but objectively it wasn't wrong. Apple released an inferior product and used out-of-band…

Post by light_triad » Tue, May 26, 2026, 8:39 PM UTC

bhouston wrote: post #124

Dropbox's stock has been stuck at around $6B valuation for years with flat growth and income around $2.5B per year. It is just stuck. Box.com, which is quite similar, is not that different. Around $3B and $1.2B in income. Similar valuation. I think it is the market, not the leadership. It is a tough market that has cut off the consumer end because all the big players have their own deeply integrated solutions: Apple…

Post by ra0x3 » Tue, May 26, 2026, 8:45 PM UTC

dhouston wrote: post #176

joshmn wrote: post #128

If there are any Dropboxers here (drew—I emailed you a few weeks ago, but I imagine you're busy): I went to prison for 18 months, my digital and physical life was stolen from me: https://news.ycombinator.com/item?id=45451567 applies to my Dropbox account (and Apple but separate problem); I just received the "your account will be going bye-bye" email. I have very important dead-mom-club stuff in there, and support is…

Hi Josh -- Drew here -- our escalations team should be reaching out shortly. (Losing phone, 2FA keys, etc. can be tricky but they should be able to work with you and hopefully verify enough to get you unblocked.)

Post by nashadelic » Tue, May 26, 2026, 8:47 PM UTC

light_triad wrote: post #195

bhouston wrote: post #124

Dropbox's stock has been stuck at around $6B valuation for years with flat growth and income around $2.5B per year. It is just stuck. Box.com, which is quite similar, is not that different. Around $3B and $1.2B in income. Similar valuation. I think it is the market, not the leadership. It is a tough market that has cut off the consumer end because all the big players have their own deeply integrated solutions: Apple…

It was both the market and the leadership. Dropbox failed to find a second act: they struggled to find PMF with their acquisitions and new products: Dropbox Passwords, Dropbox Paper, Carousel etc. As Steve Jobs warned Drew Houston, Dropbox was "a feature, not a product"