Dropbox CEO Drew Houston to step down

aghuang 328 points 349 comments May 26, 2026
www.cnbc.com · View on Hacker News

https://blog.dropbox.com/topics/company/dropbox-leadership-u... https://twitter.com/drewhouston/status/2059275240065425474?s...

Discussion Highlights (20 comments)

georgel

The circle is complete: https://news.ycombinator.com/item?id=8863

gigatree

Board finally realized people can just do this themselves with FTP/SVN/rsync and curlftpfs

browningstreet

Having just rsync'd 100s of GBs back down from B2 and not sure where to put it, and having lots and lots of business documents and video files to share with collaborators, I'm surprised how few competitors there are in the Dropbox space. With their block level syncing, Dropbox is still not really replicated in the market. I'd only take issue with their price given the volumes of data I'm dealing with. Being able to set local and not-local flags on files/folders is great. I spent some time trying to use a few of their alternatives, plus their mobile client apps, and it's kinda just Dropbox still.

sidcool

Is he the next Member of Technical staff at Anthropic?

wwweston

Really hope that all the positives in the leadership announcement are true. Things have reached the point where I probably could use open sync+storage options to achieve what I do with Dropbox (and perhaps eventually I will do that as a hedge against the risks of Dropbox enshitification). But I'd love to see Dropbox continue to provide worthy convenient service.

postalcoder

I think I've spent more on dropbox, lifetime, than most other subscriptions (it's also the first service i thought was worth paying a subscription for). I still pay for it. Drew built a great service. On the other hand, I can't think of a single new feature they've introduced since 2011 that matters. All I care about is packrat and good syncing. Is there anybody that loves anything they've built in the last fifteen years? I feel like the company could have had a skeleton crew keeping the lights on and I wouldn't have noticed a thing. Now, in 2026, all I want is for my coding agent to be able to grep the files in dropbox. Feel like dropbox will sooner rely on selling merch than offer something useful like that, though.

hylaride

Dropbox was an excellent service back in the day. Then they re-wrote their desktop apps (I think in python?) and it never synced cleanly after that. I'm all-in on the apple ecosystem, so while it's not perfect, iCloud storage works better. Was a shame, though.

vednig

I wish Drew all the best for his journey, he built the market for many generations to come.

ivraatiems

I think Dropbox is great, but I got about 10GB of storage via affiliate links ten years ago and I've never upgraded or paid a cent since. I'm sure I'm a huge loss for them. And even despite enjoying their service, if Google Drive produced a Windows integration that actually worked well, I'd leave for it in a minute. I'd never use OneDrive, but that's more out of spite at Microsoft shoving it at me than because it is bad in any way I know of clearly.

ecommerceguy

call me crazy im still using a 100gb box account from when i bought an hp touchpad. that thing was so cool.

njt

I recently placed some PDF files for some nontechnical people on Dropbox. To avoid confusing them with the long complicated Dropbox URL, I even created a shortened link for them to use (think https://event.myorg.test ). Almost none of them had Dropbox accounts. I found out later from someone that 90% of them couldn’t access the files. The link didn’t require a login but they made it look to the unsophisticated observer that you need an account to get the files. So these folks (most of them were elderly), just gave up.

krashidov

I am surprised they aren't leaning into the agent dev tool mania right now. File syncing is actually very in demand right now and everyone is not doing a great job figuring it out.

arbirk

They focused on the wrong product imo. File sync as in syncing the files you are actively working on and temporary files like clipboard etc. is powerful. Syncing folders and doing backups is difficult and expensive. I am still looking for a good product that makes it easy to do all that.

unpopularopp

I wish they had a plan between free and 120€/year. I don't need 2TB storage but the free plan's 2GB is also nothing

zengid

Drew was CEO for almost 20 years right? that's a heck of a run!

farcaster

10 years ago they had such a nice feature of grabbing your pictures metadata and showing them on the globe (Immich does this too). And they just scrapped it for no reason. I guess they wanted to make dropbox into more of a collaborative google docs kind of thing. But that's not why I started paying for it.

jabedude

Why are the HN comments about how Dropbox's business is not doing well? I don't think there's any indication that Drew is stepping down because of that?

kasperset

One of my favorite product, it just works in the background. I do not need any more features than what it has currently. None of the competitors have this ability to just blend in the background. I hope they stay for a long time.

jaredcwhite

I've used and paid for Dropbox for well over a decade. Other than the rare hiccup every few years (usually due to switching machines/OSes or whatnot), it's been rock solid and a true workhorse. I know there are many other options, including iCloud Drive which I use sparingly, but Dropbox is a service I trust . I hope it continues in that manner and they don't destroy their reputation with a woebegone "pivot to AI".

toephu2

As Steve Jobs famously told Drew Houston..."you have a feature, not a product." Jobs was ultimately right in the end.

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