alt Hacker NewsDropbox CEO Drew Houston to step down
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Aside from the issue of platform owners (Apple, Google, Microsoft) offering storage sync as an integrated feature, which others have pointed out, the other reason growth is limited is that filesystem storage and sync thereof has become less critical over time. Our apps increasingly do cloud-native walled-garden storage: docs in Google Docs / Notion / Confluence, mocks in Figma, etc. And code was cloud-native with version control much earlier.
I need sync for just photos on my phone (which Apple or Google are better for), and a small number of esigned PDFs and tax documents (for which any provider's free tier suffices).
Dropbox solved a problem of the 2010s.
I was lucky enough to work at Dropbox for a bit. Awesome engineering culture and such good people. Got to even grab a beer and rip karaoke with Drew. Thanks for creating such an awesome working environment Drew. I cannot say thank you enough for those memories or that experience. By far the best CEO and leader I've seen.
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.
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.
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 (iCloud), Google (Drive), Microsoft (OneDrive).
Not sure where to go since the big guys won't acquire you given that they have alternatives. Maybe a business software acquirer like Salesforce or Dell? Or an AI company that would use this type of cloud storage as a AI document store / collaboration hub?
I honestly do not know where to go.
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.
The circle is complete: https://news.ycombinator.com/item?id=8863
It would be a shame to see Dropbox decline. They're the last big player to maintain a Linux sync client that just works reliably. I've tried to host Nextcloud and tried Syncthing as well, but Dropbox has always worked for when I just want the problem solved without worrying about something going down.
Open to recommendations...
I always thought it was a shame that Dropbox never had a tier between its free tier which is not usable and its first paid tier. I would've gladly paid around $3, $5 for a few tens of Gigs of storage, but the almost $10 per month is too much. Then Apple iCloud came and filled that gap beautifully. So I give them my money.
I feel like they left a lot of money on the table.
I had the opportunity to live with Drew back in 2006 when he, I, and another pair of YC founders Adam and Matt were living together and hacking away at our own startups in Cambridge. I remember Drew being a hard worker, humble, and a genuinely nice guy. It's probably self indulgent to claim that we all inspired him to eventually shift gears to Dropbox and apply to YC - but what a path it's been for him! I've always felt inspired by his meteoric innovation in cloud storage - Dropbox paved the way for all our modern cloud storage systems. We've fallen out of touch over the years, but I wish him well on whatever comes next.
A few years ago Dropbox just stopped working for the basic thing it is supposed to do -- let me access lots of files without taking up tons of local drive space. Since then I have not stopped using/paying, but i have stopped counting on it and I have stopped adding new files to it, sharing files with it, etc.
The constant marketing for "dropbox for business" (which is priced badly and is not something I've ever felt comfortable recommending to any business) was also quite irritating.
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.
When Dropbox first came out I loved the simplicity of it for years. That rock solid little icon in my system tray that never bothered me, just reliably synced my files. It was excellent.
At a certain point (mid-2010s) things started to go off the rails from a design, marketing and complexity standpoint. Suddenly having a Dropbox account felt a lot more complicated - so I stopped using it.
The change was almost hard to describe, but I think it's encapsulated well if you compare the Dropbox homepage from, say, 2013 to 2019.
2013: https://web.archive.org/web/20130701190140/https://www.dropb...
2019: https://web.archive.org/web/20191130224813/https://www.dropb...
I realize that companies that want to become large behemoths naturally seem to have to go down this path - just saying I miss the simplicity of it in its earlier form!
Drew was CEO for almost 20 years right? that's a heck of a run!
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?
They had a terrific product that worked well in ~2013, but they haven't innovated since then (TBH, not sure what "innovation" means in the file-sync space.) Although Y-o-Y revenue is mostly flat, I'm a little surprised that they still brought in $630M the last quarter, and that they still have 2,000 employees. Looking at what Dropbox does, I would have guesstimated they were a 250-person company.
All the best to their employees, but I think a big round of layoffs will be coming within the next couple of quarters.
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.
Your Python client eats all my CPU. My CPU usage goes down from 75% to 5% when I close it.
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
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.
Dropbox was always a feature in search of a product.
It’s stable and profitable (which is more than can be said of most tech companies these days), but the stock is basically flat since it’s IPO a decade ago.
How is this company still alive?
They’ve dragged their feet on evolving and offer nothing new in almost a decade.
Drew was the original inspiration for me to get into startups. He was a few years ahead of me at MIT and did MIT's Battlecode competition as well. He introduced me to Hacker News, Paul Graham's writing, YC, and the Silicon Valley ecosystem. What he built with Dropbox was the first proof point of the YC model. I'm tremendously appreciative of what he's done for the next generation of enterepreneurs.
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".
I have been one of the very early users. Maybe from the first weeks (if not days). It used to be such a good app and service. So good that I used to ask my friends why they didn't already use it. That was a few many years ago; at best. Since then, Dropbox has steadily been going downhill and with intent, at least for a consumer. Quite a few folks are ditching its paid plan (including me), just using its free tier (to tiny tasks like notes sync etc) and moving the bulk of their data storage elsewhere (like I did - reluctantly to object storage providers via many FOSS CLI tools; would have loved to keep paying for the old Dropbox). Hostile pricing was not the only concern; hostile UX, an insanely bloated app, and breaking features (because sure, those are not bugs) galore.
Now the native file sync is a really doomed space for individual customers (because I have never explored what's out there exclusively for enterprise). Dropbox is well Dropbox New. Anyone in their right minds, or if anyone has a device other than an Apple device, will not even think of relying on the (even after years of complaints) opaque and buggy iCloud. Google Drive, while most reliable technically, is a really bad bet as a filesystem file sync tool; besides, they are much more bloated than Dropbox, and their suite offerings are intertwined with it so deep. Smaller offerings like Tresorit (though most "native" among its peers) are too buggy and have questionable practices like that of pCloud, etc.
So while the entire personal/consumer filesystem file sync system has gone to the gutter now, Dropbox is still a bad solution among quite worse ones and that's really sad. From storing 100s of GBs at one point, I am back to just ~300 MB in Dropbox now. Just couldn't trust it anymore after it broke my workflows quite a few times and still keeps trying with that sudden pop-up of "Update Available" which is not really an app update (app updates silently in the bg; all hail Electron), that is actually a sly way to make you enable its folder on File Provider API feature. I am sure it is a good feature for many but for heaven's sake the very reason I started using (and still use Dropbox for) is because it syncs my complete files across systems. The lest you can do is not actively try to make me click on it. Besides I don't want any other bloody thing. Just give me that feature, and only that, and take my money and in a native app while we are at it. There are LLMs now, give us back a native app at least.
Seeing the focus on "AI" I am pretty sure very soon I'll have to take even that ~300 MB elsewhere.
PS. Their support is absolutely questionable. I've had a chance to contact them for some bugs. Goodness, it took literally weeks, and dozens of messages, to make them accept it's a bug and even then they didn't really accept they just stopped responding (so I assume they accepted it. Besides it was never fixed :D).
I really hope the next person in charge gives up on business deals and aims for more personal updates. I store all my photos on Dropbox. The fact that they don’t a have a good way to manage it is still painful
As tired as I am of the lack of improvement in Dropbox and the most of my nag-mails being warnings about my inactive Dropbox storage reaching "dangerous lows", I can't help be frustrated at how much the equivalent virtual drives from Apple and Microsoft suck, even today.
As Steve Jobs famously told Drew Houston..."you have a feature, not a product."
Jobs was ultimately right in the end.
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.
call me crazy im still using a 100gb box account from when i bought an hp touchpad. that thing was so cool.
Remember when Dropbox was a folder that just syncs? [1]
So, Web 2.0 is finally over now?
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.
my take dhouston should go be a CTO somewhere.
technically he's rich enough to never work again. but he's hungry, young & smart
& can really push the industry forward - by taking one of the f500 that's tech adjacent & be CTO
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.
This guy’s LinkedIn hid his undergrad and put up a 3 year Harvard Extension School management degree tells you all you need to know.
end of an era! Dropbox has now fully ship-of-theseus'd itself from my perspective. (which is impressive honestly given the time frame)
I wish Drew all the best for his journey, he built the market for many generations to come.
Drew is clearly a very competent engineer who built an amazing product and company. He was the right person to build it from zero all the way to an IPO, but wasn't the right person to keep scaling it. Dropbox's product vision in the last 10 years was lacking to say the least. Their latest innovative product "Dash" is another flop, like Dropbox Password, Paper, and many others.
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.
In these days of concerns over digital sovereignty, I cannot help but wonder if they would be best served by moving to a privacy-protective European state, e.g., Germany or Switzerland (not EU but tends to align with EU regs, e.g., GDPR) and doubling down as a privacy protection service (to the extent permitted by law).
Just musing....
I've used for dropbox for the last 13+ years, was an early customer, and absolutely love the core product.
However, in the last handful of years, I've been incredibly disappointed in the stagnation of their products.
Dropbox was the first 'virtual desktop' I created that allowed me to hop into new companies and get going in a seamless way. Beyond just dotfiles, I was able to keep applications too, it was so easy to sync and get everything setup at a new company.
When repl.it came out, I wondered why Dropbox hadn't done that first. There's all sorts of room for innovation here - being able to install the right binaries, perfectly configuring a cloud command line setup, syncing configs, etc.
Photos - I have the majority of phots from my adult life stored on dropbox. But the searching is crap compared to google. It's not easy to share or make albums. Dropbox could have been a mini-social media site, a way to share photos, collages, albums easily with friends - but it has half the features of google photos!
Collaborative Editing - They probably could have done something here too, but I never saw a compelling attempt.
Dropbox is still a great product for file syncing, but I fear that they will slowly lose relevance if they don't get another hit product.
Fuckin finally
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 useless. :(
Edit: Thanks unofficial Dropbox support channel; thanks Drew :)
Edit edit: Try my luck with my Apple account now, I guess—Tim Cook, you busy?
Board finally realized people can just do this themselves with FTP/SVN/rsync and curlftpfs
Kudos to @DHouston and co. for starting and keeping the company going.
Somehow, in my mind, Dropbox is always associated with the classic HN comment [1] about "...you can already build such a system yourself quite trivially by getting an FTP account, mounting it locally with curlftpfs, ..." ;-) ;-)
Trivial indeed /s
Ashraf seems like a great leader. I am not too excited about the focus on AI. Lets see where it goes.
Drew launched a great new product, fine tuned it to be one of most loved and then made profitable company. Respect