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?
Think about it. If you're paying all your bills, all your wages, and you have a strong product that people enjoy, and you're able to compete in the market - maybe not gaining any ground, but at least not losing any either - why change?
Of course I moderately understand the market pressures at work, but at some point in the human civilization journey we'll have to be content with something instead of chasing clouds all the time.
It's not necessarily bad, but in tech, not actively growing is tantamount to shrinking. Organic customer churn and attrition means that you're just a few years away from irrelevance. If DBX wants to stay a stable tech company, it should figure out a way to go private.
Exponential growth can’t last forever, and I do worry about what will happen when the gravy train stops. Maybe we can figure out interstellar travel before it does so the limiting factor becomes “the galaxy” rather than “our planet”.
Not everything is in the exponential growth model. Most small businesses in your town for example. Margins might afford an upper middle class lifestyle for the owner and that is a good enough business model for this company to last decades, even pass down through the family.
On the micro level, I agree. On the macro level, I don't know how viable those businesses will be when the wider economy is no longer growing exponentially (and frankly that may well be the least of all concerns).
> In the aftermath of World War I, birth rates in the United States and many European countries fell below replacement level. This prompted concern about population decline.[8] The recovery of the birth rate in most Western countries around 1940 that produced the "baby boom", with annual growth rates in the 1.0 – 1.5% range, and which peaked during the period 1962–1968 at 2.1% per year,[13] temporarily dispelled prior concerns about population decline, and the world was once again fearful of overpopulation. After 1968, the global population growth rate started a long decline. The Population Division of the United Nations Department of Economic and Social Affairs (UNDESA) has reported that in the year 2023 it had dropped to about 0.9%,[13] less than half of its peak between 1962 and 1968. Although still growing, the UN predicts that global population will level out around 2084,[81] and some sources predict the start of a decline before then.
In other words, the last time everyone got worked up over this, the trend reversed itself too hard within a few decades, and then reversed itself again. Meanwhile, over half a century after the "decline" started, we have over twice as many people as we had when it started, and the earliest projections for when growth will stop is another half century from now. I think there are a lot bigger problems we'll need to reckon with before then, and if we manage to remain stable by then, it seems like we have good precedent for reversing it fairly quickly.
> at some point in the human civilization journey we'll have to be content with something instead of chasing clouds all the time.
Surely we're not even close to this point though? I can think of a lot of things that would be incredibly good for humanity to have, and which are achievable with enough economic growth, but which we are currently very far from because our economy does not have the necessary productive capacity (for example, enough solar/wind/nuclear/renewable power to completely eliminate our dependence on fossil fuels)
The point is that we should be directing our energy in a direction that’s net useful for human kind which should translate into growth. Dropbox is not one of those because there are many viable alternatives.
I mean sure, but marginally better/more profitable file storage isn’t any of that, and artificially juicing the share value doesn’t actually make any difference to the real economy it just makes some people who like gambling on made up numbers happier for a bit.
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"
It's a great product. They had the brand, the capital, and the user base to become what Slack, Zoom, or Notion became. Instead, they spent a decade fighting a losing battle over storage pricing with Google and Microsoft. Their lack of a second act is due to a failure of product vision and enterprise execution.
> They had the brand, the capital, and the user base to become what Slack, Zoom, or Notion became. Instead, they spent a decade fighting a losing battle over storage pricing with Google and Microsoft
Is the alternative not likely that they would have spent a decade fighting a losing battle over office software with Google and Microsoft? Paper was a great product but the big guys have vertical integration so companies prefer their end-to-end solutions (GSuite etc) and I don't see how Dropbox could have easily overcome that.
And they had Paper, which was an excellent product (I was at Dropbox a decade ago; we all used Paper constantly and it was great) very close to what Notion later became. They never got it over the hump to wider PMF — like you say, a failure of product and of enterprise execution.
(Given that it was so close to Notion, I think Paper is one area where the product vision was on to something good; but they didn't succeed at product execution, connecting customer feedback to iterating correctly on product improvements.)
I don't see the need to become bloated like slack and a one size fits all application. They do a great job with the product they have. Is there anything wrong with just being what you are? Why does the lack of a second act need to be a bad thing if your first product is great and still extremely valuable?
I would also if anything put Zoom in with Dropbox, they have a product that is by far the most enjoyable to use in that space, but any other offshoot is not worth it.
Unfortunately this is the case when a company is beholden to investors. Investors aren't getting into the business of "making a steady stream of money without outsized growth" unless you are Warren Buffett.
Most investors are focused on multiplying their investment many times over, and generating hundreds of millions of dollars in net income a year is not big enough.
And this is one reason why the world is burning (literally and figuratively).
If you look at all the tech companies doing buybacks, usually the shares created for employee RSUs matches or exceeds the shares retired from buybacks.
Not in all cases, but many
Which is why GAAP earnings matter and not free cash flow
> 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).
A huge unforced error though is that the starting price for individual plans is $20/year versus $10/month for Dropbox and Box. At a certain point you have to recognize that the rules of the game have changed. Once a customer has their foot in the door with a cheaper plan that also offers better integration, why would they move to Dropbox or Box?
They probably have to prove to me nobody can read my files besides me & the NSA (no “our 134 advertising partners …”)
unless they really want to wait for iOneGDrive to enshittify
Edit: as it stands, sounds like uploading already encrypted files to AWS is the option for privacy hawks who still want cloud - such a small market but think it should grow
> AI company that would use this type of cloud storage as a AI document store / collaboration hub?
Wouldn't that run into the same problem the consumer end has? MS bundles 2TB of OneDrive storage for every user with a M365 license, and Workspace does more or less the same. You can already connect pretty much anything to them as is for pseudo-RAG/enterprise search.
The aggressive bundling from the big players have taken away most of the reasons to pay for Dropbox or box.com and other cloud storage providers.
A business that can bring in a steady $2.5B a year doesn't seem like a bad business to me, so long as they can turn that into a profit. I think there ought to be a recognized place in the ecosystem for this sort of thing, and for me their independence from the gigacorps is a major feature.
Dropbox has deep integration ecosystems, runs your company's data, I think its a no-brainer for it to become the agentic memory for your company if done right with it syncing data across all company services.
I'm really not sure what Dropbox could even do other than have gone full swing towards a serious pivot or a new expansion into a new domain, but if they were going to do that they should have done that some years ago, if their current CEO stepping down alarms some of their existing customers, it might not end well.
Dropbox is one of those companies that did something right, and its kind of sad seeing them in this weird limbo state. I hope they don't wind up crashing down hard before they can finally figure something new out. I think their time to shift from being a "single service / product" style company is long overdue. They don't need to shutdown anything they currently have, but it would be in their best interest to either acquire a smaller complimentary but profitable company, or start building products that compliment their current offering. I really do wonder why they had not done so sooner.
> acquire a smaller complimentary but profitable company, or start building products that compliment their current offering
I think they've been doing that, but it's tough to do it successfully. Often the best thing is to return money to the shareholders so they can look for higher returns elsewhere. I think the fact that they're still in business is kind of a miracle considering the competition.
Problem is most consumers and businesses would rather pay for 1 product that does 7 things ok than 7 products that do 1 thing great each. The former is cheaper and often is easier to cross-integrate - I'd rather just use AWS or GCP storage options than ever touch drop box
> would rather pay for 1 product that does 7 things ok than 7 products that do 1 thing great each
See Microsoft/Office 365. Aggressive bundling means one license gets you literally everything. Sure, it's all mediocre but it checks boxes and is largely "good enough." No reason to go out and buy slack, zoom, box.com/dropbox, 3rd party email gateways, 3rd party EDR, DLP, an MDM, etc. Microsoft will sell you whatever "checks boxes" product you need under one license and cheaper than buying separately.
I mean yeah, who would rather spend time at their job helping other users figure out how to include the right add-in for Dropbox to work with their various apps vs how Office integrates with OneDrive or Google Mail, Sheets, et al. integrates with Drive? Thus adding another layer of software to manage updates, etc. At some point, there is an opportunity cost to using siloed products, especially for something that's become relatively commoditized like cloud storage.
They never tried to expand the TAM. Storage/servers were not rented out while others HuggingFace/Github/Digital Ocean/Cloudflare etc. sold them to expand their TAM.
I think the analog is the actions around the storage.
DropBox & Box have both moved in this direction, but perhaps not aggressively enough? I'm thinking in particular about e-signing, where DocuSign has a market cap roughly equal to the sum of DropBox & Box. Both have e-sign products; I am fairly certain that I have never encountered either in the wild despite routinely being sent other e-sign links.
AI is perhaps another emerging opportunity. Instead of uploading documents to a dumb pipe, let me have the pipe do things to them. Dumb, simple example would be I can put PDFs in a folder and after a one-time setup, I can share an API link that lets my users extract specified data from those PDFs via secure JSON API. Or simple CMS instead of WordPress. Or analyze documents flowing through a folder for x, y, z anomalies and alert me.
Perhaps think of the stock as a value stock, not a growth/momentum stock.
The thesis is that they should survive and thrive as an investment asset through the AI bust, but performance during the AI bubble is poor. If you are a longer term investor then B2B SaaS valuations appear cheap right now, but you need to be able to weather the storm of missing out on the AI infused bubble.
As evidence the BVP Nasdaq Emerging Cloud Index is at all-time lows for EV/revenue multiples. While some of the companies will see growth rates impacted by AI, that only explains a little bit of the drop in multiples versus the past.
I don't necessarily think that these companies have much room for market cap growth but it is definitely interesting that right at this moment the value of local has gone way up due to Claude Code (plus Cowork and competitors). I suspect that will change in the next several months but I know people who are actively switching from Google Docs to Office because of these tools.
I remember when DBX IPOed and there were a large number of HNers who said proudly they were going to buy the stock and sit on it.. I was always concerned about where Dropbox (and Box.com) goes from here? Network storage always seemed more like a feature than a company, a different flavor of photo storage like Flickr. Didn't Google try and buy them initially?
So I wouldn't say it's the market per se. It's just that network storage has become commoditized. Storage tied to Google, Microsoft or Apple is always going to have a market advantage.
only a hyper capitalist would think $2.5B/year is "flat growth". maybe instead of paying out shareholders, short term gains. maybe invest in their workforce or company itself?
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.
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?
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.)
Appreciate the context, however if I was to follow up on my own comment. You were sentenced to prison, I went to the grocery store yesterday. It's the casualness of the phrasing that is jarring.
Oh man, sorry to hear that. I had a secondary Dropbox account I used for a few small but important documents. At some point I somehow lost the 2FA factor, and I don't know how as I've managed to keep the 2FA for every other one of my services across multiple app/os/phone installs.
Anyway, I reached out to their support for help and they were utterly useless. I had a couple weeks of back and forth with them before giving up. I hope I never actually need those docs.
Fair criticism. The tricky part though with any scaled service is that for every legitimate case like this, there are many more bad actors trying to hijack accounts through exactly this mechanism -- so account recovery has to be conservative by default, which means legitimate cases sometimes get caught in the friction. Not an excuse, but it's a hard problem at scale and not just e.g. a cost-cutting thing or not giving a shit.
> The tricky part though with any scaled service is that for every legitimate case like this, there are many more bad actors trying to hijack accounts through exactly this mechanism
I really wish more people understood this, especially on HN.
Account recovery flows are flooded with people trying to break into other people's accounts. It's going to be nearly impossible to make a system that can allow someone to recovery their account without also accidentally allowing someone to social engineering their way into someone else's account.
No indicator of AI writing is going to last forever. We really shouldn't over index on the oldest indicator (which is liable to decay first). People are starting to say "delve" more in verbal conversations. This treadmill will keep moving. Unfortunately we have little choice but to keep up with it.
I was selling a GPU on Facebook marketplace during covid.
The description was that the card was good for gaming or “turning dinosaurs into clean money”.
Banned permanently and no way to ever reach a human.
I sold a rifle legally on an online auction site. The buyer was offered to pay with PayPal they were given the option to use. The buyer took that option, making me break PayPal TOS.
Banned permanently and no way to ever reach a human.
Banned from Venmo, absolutely no idea why. SO banned from Venmo, absolutely no idea why.
Banned permanently and no way to ever reach a human.
It's the digital equivalent of your house burning down, your devices are inside it, and you never bothered to bring the 2FA codes you definitely wrote down to the bank.
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.
It's a bad market to take on because the competition is 'commodification by Google/Apple/Microsoft'. If you do a great job you compete with Dropbox on price and quality, and if you do anything short of that you compete with the office suite versions of the same product, which are effectively free to their subscribers (because file sync is packaged with other services that they're buying anyway) so getting people to give you money is very hard. Dropbox itself is perpetually at risk of being commodified out of existence; their constant battle is finding ways to make sure their customers can still justify paying for them as a separate service.
(at least this was the ambient understanding internally when I worked there a few years ago)
The value proposition of Dropbox is exactly that it is an independent service, in my view (in addition to having best-in-class desktop integration). Google/Apple/Microsoft can’t compete with that almost by definition.
While not everyone values that, I suspect that enough people do to warrant Dropbox’ existence.
For an individual sure, but the vast majority of their business is corporate contracts which don't think that way.
Generally it is impossible to understand Dropbox's strategy if you think about individual purchasers as significant. Iirc they mostly serve as a marketing funnel for team- and business-sized contracts. (although this varies from year to year, sometimes they do focus on e.g. family plans for revenue)
Yeah, I understand that Dropbox isn’t thinking how I think. My argument is that even if they lose these corporate contracts, it should still be a viable (if much smaller) business to serve those users that do care. In other words, it wouldn’t force Dropbox to entirely stop existing.
You have nothing to say but you still want to be heard.
if they lose these corporate contracts, it should still be a viable (if much smaller) business
Thank you for clarifying that if Dropbox loses their biggest customers, they will be a much smaller business. what a big genius we have here.
In other words, it wouldn’t force Dropbox to entirely stop existing.
another brilliant stroke of genius. if mcdonald's closed all their stores and only existed in airports, they would not disappear entirety but possibly continue to exist? fascinating.
> I'm surprised how few competitors there are in the Dropbox space.
There used to be many more - Sugarsync, AeroFS, Syncplicity, just to name a few - all bit the dust. Box.com found a niche serving business document flows; Gdrive, iCloud, OneDrive, all survived thanks to being features in a broader Big Tech suite. Everybody else? Outcompeted, plain and simple. Dropbox was just a cut above.
(I used to work at one of the companies named above, so although it's just one person's opinion, it's at least as informed as anyone else's here :) )
it really is too bad. All of the major tech companies' competitors are junk. Google Drive is the least bad of the bunch (out of, say, OneDrive, iCloud, and formerly Amazon Drive), but it's still not great to deal with. DropBox really does do a great job
Considering I have one friend who just lost data due to a OneDrive bug less than a month ago, I'm going to say no. I have zero tolerance for data loss.
The desktop client used to be just terrible. Has that changed? The Dropbox client does have its issues but it's really amazing at... Syncing files. I use it pretty creatively with large numbers of files and large volumes and it just works reliably.
This is more than S3 charges, but S3 will nickel and dime you aggressively for using that storage depending on your use case.
But $22/month buys an entire Google Workspace seat, which includes 5TB, for an effective $5.50/TB/month, which is quite a good deal. On the other hand, it’s rather lacking in flexibility.
I find this all somewhat confusing. At least one of these offerings does not reflect the underlying cost of the product.
It doesn't have a great cross platform support (no Linux client, and there are many complaints for the Windows client).
Personally, I dislike that you cannot restore an older version of a file on laptop/phone, and must instead use their web app, for which you need to disable ADP, which defeats its purpose.
I think they're squeezed between bigcorps offering consumers products in ecosystems they're already bought into, and independent-minded techies more willing to roll their own solutions.
I paid for Dropbox for a long time specifically because it was an independent option, but over time the feature bloat annoyed me more and more, and their dabbling in genai stuff was the last straw. Now I use syncthing over wireguard tunnels.
I'm surprised by how many people mention Syncthing as an alternative to Dropbox or Google drive. It's not. Syncthing forces you to have a copy of your data on all your devices. With Dropbox or Google drive you can "stream" only the files you need. This is important when you want to share GB of data with devices that can't sync everything into local storage (like a phone)
I've been trying to use it for a massive tree of ~250k files across ~500k folders, which only needs to live on one device at a time and sync to a backup in case it dies, and even if I tell it send-only/receive-only explicitly, it regularly seems to go cross-eyed at some change made in the folder structure and give up and rescan and hash everything, and if anything in the tree changes while that's happening, it gives up and just marks it a conflict to be manually resolved...or silently hangs until I restart it.
It's working well for me (as in totally hands off for months or even years at a time) at (I think, roughly) a few hundred thousand files but probably significantly fewer directories. Overall I'm really impressed and happy with it. But this is just personal file sync, nothing too demanding and unlikely to hit edge cases with concurrent edits etc.
How much are you willing to pay for this service? Ballpark. And what is your ratio of data at rest vs data you want shared? Are you ok with your permanent copy being local?
>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.
Business Strategy 101 teaches that broadly speaking, there are 3 categories into which companies fall, which are cost leadership, differentiation, or segment focus.
If, as you say, your only pain point is the cost of dropbox, then any potential alternative would be competing to be the cost leader, and cost leadership strategies are unattractive for startups. Nobody is investing in early-stage companies building "a cheaper clone of XYZ". It's hard to attract startup talent to "a cheaper clone of XYZ". It's rarely fun for founders to build "a cheaper clone of XYZ".
Unfortunately I think there are limited avenues for successful differentiation in the file sync space. Self-hosted vs cloud, standalone vs OS-level integration, cross-platform vs not? Can't think of much else off the top of my head, and I think big players are able to throw shitloads of engineering talent at OS-level integration features (and that gets you iCloud, basically).
Beating dropbox at their own game wouldn't be impossible, but I think that's why there aren't many competitors in that space.
The real issue is that if you do manage to build a cheaper clone they can just delete you by lowering their prices. It'll hurt the growth they have to show investors but not as much as letting you live will.
>The real issue is that if you do manage to build a cheaper clone they can just delete you by lowering their prices.
Yep, this is why cost leadership strategies tend to be unattractive to startups. Finding ways to be meticulously frugal just isn't exciting to most people, I would think.
Well my point is that it's not a question of how exciting it is. It is that it is essentially unworkable as a business strategy, unless you have a technique for being more frugal or efficient than it is possible for your competitor to be. And they have scale on their side, so it is doubtful.
(that said I'm just an engineer parroting things I heard while working there, I wasn't involved in any actual strategy)
A local copy is inherently fragile. It's easily destroyed by accident, flood, fire etc. This is especially true when using a single storage device like an SD Card, vs the way that these storage services operate, leveraging things like erasure encoding.
Local backups are important, they're cheap, and often fast. They just shouldn't be the only kind of backup you do for data that is important to you.
TM was a hack - iCloud is pretty good I reckon - for the millions of devices they have in the market there has been the only odd complaint from somebody on twitter making headlines with a Technorati type of following about user accounts mysterious being deleted or blocked (poor customer support) or some weird syncing issues when moving to a new device and the old device is still in use.
Edit: Read the comment below, it's information I should have included in the first place. It's important to note that the comment was helpful at the time, and only became a meme later.
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.
The "viral" point was a good one, and which they solved quite cleverly: as a student I got 10 GB for free, but additional 10 GB for each recruited person. Everyone at campus was on a recruiting spree for a while, to bulk up free storage.
Of course, that doesn't make them money. But millions of users that then had all their files there and kept using it when no longer students (so paying), and recommended it to their places of work etc.
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 techniques to sell it.
> The contemporaneous iPod _was_ technically and acoustically inferior to the Nomad.
You're cherry-picking your "technicals". The click wheel hardware and software implementation (especially the UI response time) was (and still is) revolutionary.
iPod won on the technical merits; just not the ones you're focusing.
The anti-Apple crowd on here loves to crow about how Apple only wins on marketing. Look I find the ads cringe as fuck too, but let's not pretend that the hardware isn't much, much better than average.
Better than all? No certainly not, Apple's build quality loses out to plenty of much more premium products. But it generally sits head and shoulders above the average build quality of any given product category, which seems to be the niche they most aim for: "the upmarket version of the common offering." That ones that immediately come to mind are Macbooks and iPads.
There is probably something here about human psychology where we underestimate the switching costs of things we have already, and are wired to look at things through the lens of the world we have now.
Absolutely no-one is concerned today about what happens when you dip out of connectivity because fast mobile connectivity was not abundant in 2007 (the iPhone was only released that year), which obviates the "this will never replace a USB" criticism. Mobile made a whole new class of businesses possible.
It would be nice if that still worked. My resume exists in an iCloud drive, and I spent ten minutes on my phone trying to figure out how to attach it to a gmail message before giving up. "Copying" a file isn't even a well-defined operation anymore. (Or at least "pasting" doesn't always paste it.)
Google will often convert it to a gdrive thing instead. So you're not sending the file, just a link to the file uploaded somewhere. I'm not sure what heuristic it uses, but sometimes when mailing photos like half of them are included in the mail and half automagically uploaded to gdrive instead.
Yeah but it's the silent conversion that irks me. My email is no longer self contained or archivable. When I find it again in the future, the files might be gone.
Funnily enough, Windows 98 is the first OS I remember with a sharing menu (“Send To”, which is memorable to me because the official Russian localization of it was suggestive of an obscenity). It seemed so pointless back then.
Which just goes to show how trigger happy people are about labeling things as LLM generated. People forget that LLMs were trained on writing on the internet, so it's going to sound how the average person writes!
Tangential to the theme, here is the HN post about the (AFAIK) first public success of deep learning techniques with SuperVision's AlexNet. You can read what their prognosis on the future success of deep learning was (hint: same prognosis as Dropbox)
It's already 19 years old? But it's still so fun seeing the same joke in every thread. Again and again. Any time someone can be even hypothetically accused of underestimating complexity of a sleek replacement for a hack system, or the topic can be tied to file sharing apps. It's a lot of fun to be reminded of that comment again and again from a clever bunch on a website with a good sense of humor.
Around 2005, I was hired by a company that was building software for USB drives, to build a porn site.
Turns out, they wanted me to build a poc for an authentication solution: some USB drives would have a fingerprint reader and they wanted to build this auth system based on that.
So I built that, but "perplexingly", they didn't get any finance or enough prospect customers, so the project got shelved.
Then, I was handed another project they had on the back burner, a sort of firewall for devices, meant to prevent exfiltration of company documents on unapproved USB drives.
I built the single user version, eg you had to be admin to allow devices and the product sold quite well, even winning some prizes iirc.
We started getting requests to have a centralized admin interface and a way to allow/disallow copying some file types. I started working on the centralized admin and the company hired a very talented engineer to build the file filtering thing. This last thing was based on a windows API that allowed for virtual file systems. Things were ticking along nicely and the company even hired a business manager to try to come up with other products we can build with our existing tech.
One afternoon, over a bunch of cold beers, to link with the hell on earth that happens right now in London, me and this person came up with a cunning plan! What if you sell an 1GB USB drive with an extra 1GB of space?
The plan was simple: plug in the device, you get a drive that's the regular USB drive, but also another drive, backed by the virtual file system thing and a version of my http auth thing, and you would read/write from a server on the Internet.
Big boss liked the idea and I started researching how to get servers and the like, while a third engineer was tasked to build the desktop app needed.
It all came crashing down, days later, when this engineer declared that is not possible to have a windows app minimize to sys tray and the project got cancelled. I left the company not long after that .
This was the story on how a small German-Romanian company could have beat Dropbox.
If it makes them feel any better, I told people in the 90s that the WWW didn't make sense because we already have telnet, archie, gopher, veronica, and ftp. What can WWW give me when I already have those tools to connect with...
I said this either in late 93 or early 94. I was in a class when someone demo'ed Lynx to me, and I tore into it and the WWW. Looking at the timeline it seems that Mosaic came out right after Lynx, but my memory of it has Mosaic coming out way after Lynx. And it seemed like Navigator years after that, but the real history is super compressed. By the time I'd seen Mosaic, I was then pretty convinced of its utility.
Maybe this is sarcasm and I just didn't catch it, but I think Dropbox made a mark, and a good one at that.
The tool strangely still has a certain something that I reach for from time to time. Cross-platform(cross-era even, I just used it to move something off an ancient Windows 10 install), painless sync, painless auth, painless sharing(or not), painless updates, simple billing that isn't so high I have to factor it into my plans, and the app doesn't try to ramp my price based on how many devices I access my data from. It's just a good piece of software at a good price.
Commercially they did just fine as well according to the article: $6B in market cap, $2B/yr rev and $2B personally for Drew. Maybe not the top of YC leaderboard, but well above average.
I want more services like this one, and will keep paying for my modest storage amount until they tell me to go.
I am just like you except for the netbsd source part, and I have my own private cloud/nas with virtualization. I also at one point just started using AWS S3 as my personal dropbox on chrome for sharing files with myself, since I backup encrypted snapshots there from my cloud anyway.
but I think there are many people out there that love a gui for storing files in the cloud. i know my parents/parents friends' all use it.
I think it’s more of an ease of use issue. When I was in grad school, I used to cycle my work between dev on a MacBook and heavy processing work on a desktop. This was 2011/2012.
Dropbox helped here. They had a Linux client and a Mac client and kept both in sync.
Mine was somewhat of a niche use case. I think every one who cycled between Linux and Mac for their daily work back then thought - yeah I can definitely use those tools but an automatic sync would be nice.
What Dropbox didn’t have was a moat that comes with android or iOS. I use iCloud now since my need to move between different devices doesn’t exist anymore.
My tools are syncthing + samba: Mac Mini running Syncthing to sync the iCloud folder to my local linux server which is also running Syncthing. Linux folder synced is exposed as SMB share so I can access it from other systems.
Board finally realized people can just do this themselves with FTP/SVN/rsync and curlftpfs
The crazy part is, you pretty much can just do this yourself now, simply by pasting the famous HN comment into a good agentic AI.
While I understand and respect DanG's perspective as well as the original poster's, that comment is never not going to be funny and I'm unwilling to pretend otherwise. That said, everybody who revisits the Dropbox comment thread for a laugh really should take some time to read the rest of it. It represents a high-water mark in HN comment quality, as well as an interesting harbinger of future star power in the startup community. Some other people participating in that thread ultimately did good work and made a name for themselves, not just Drew.
"...building a net worth of more than $2 billion..." - congrats Drew and team! For all the critics, from day 1, the founders are billionaires / early employees at least in the 10s if not 100s of millions -- and so much value created for people syncing files around the world -- while hackers are still saying "...but rsync"
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.
>On the other hand, I can't think of a single new feature they've introduced since 2011 that matters.
Honestly that's what I love about it. I work on something on my desktop. Then when I go to my laptop, everything is there too. It's great. When I get another computer I can just enable Dropbox, walk away, and all my projects, notes, pictures, etc. will be there. I pay them some amount of money per month and it just works and I very rarely need to visit the website or even click on the icon in my toolbar.
Sometimes I read notes on my phone and it's kind of annoying that I can't search through text using their app, but I generally consider that to be a problem with Android rather than Dropbox.
I generally have not thought about how Dropbox spent its money until I visited the web interface, which has been redesigned for the tenth time over, and remembered that there’s still no way to see how much space your folders are taking up.
I guess I already know roughly how much space they're taking up since I just check how much space I'm using in my dropbox directory on one of my computers. From my perspective, Dropbox basically has no User Interface, but a fantastic User Experience.
For me that and end-to-end encryption (I know it's supported for teams now).
Instead they just added more annoyances over time. Every time I logged into the web interface, I would get stupid upselling advertisements (maybe don't badger your paying users with that nonsense)? I replaced the official client by Maestral years ago, because they switched to embedding a web browser, and the AFAIR the client was also trying to do upsells.
My wife were and I were customers for years. But we finally decided to terminate our subscription last year. Mostly because of the constant upgrade nagging + the orange guy taking office and Dropbox not providing E2E encryption on family accounts. So we switched to Proton Drive. It's worse in many ways, but at least it's E2E encrypted and doesn't shove upgrading ads in our faces all the time.
E2E is supported for specific types of folders available only to teams but the admin has to enable it and that folder has to be used. You can't apply it team wide to all users. It's a very poor implementation.
There is a lot to be said for staying small and doing one thing really, really well. Any time a service I like tries to expand their business, usually to appease investors, that's when things start to go downhill and I start looking for alternatives.
> There is a lot to be said for staying small and doing one thing really, really well.
Man. 1Password is another example of this. They've chased growth and no longer seem to be able to build a browser extension that actually works. I've been seriously considering dropping 1PW because of it.
That’s also what I care about, but the atrocious client (and the m1 thing) and the constant nagging in the web interface was too much. I cancelled and now use a mixture of icloud, airdrop, and rsync/sftp with remote servers.
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.
You don't need account, that's for sure, but multiple times I've seen a big upsell popup that suggests that account is required, while the tiny gray button "skip to files" is on the very bottom. I hate such patterns.
The dark pattern nags to unregistered users for shared files are the number one reason I permanently abandoned Dropbox for personal and business use. It was subtle at first, then it got pathetically bad.
When a company like Dropbox prioritizes user account growth over usability, that company debases itself and deserves to lose.
Man HN was a different place back then. People sharing ideas and getting constructive (even if comically wrong) feedback. It reads more like founders and hackers helping each other. The discussions lately are more like folks armchair analyzing or speculating companies that are already incumbent tech giants.
Or maybe I just click those headlines at a higher rate..
Yes, although unfortunately the only problem with it, there's no way to contribute to older topics in a meaningful way. Due to the nature of this format not even the original author checks old comments and absolutely no chance any new conversation sparks out of it.
> It's frankly depressing how few places there are to have quality conversations
Yeah I used to learn so much across quite a few forums. Most of those communities are dead, dying, filled with bots or filled with people making shit up/just posting lousy jokes now. A lot of folks have jumped to Discord, which frankly, isn't for me, so feeling a bit lost on where to surf these days
I was user 315, back when it was possible to determine your user number via the public url feature.
Is there anything this simple now? What I miss is being able to right click on an item, click "copy public URL", paste it into the browser, and get an exact copy of that item (with nothing else; no image overlays, no ads, nothing).
In the limit case you should be able to use it as a webhosting service for static files, since visiting an html page in a browser serves that file and relative links are preserved.
I guess it's a losing value proposition, but it sure would be nice.
It's unfortunate the original demo video was lost to time. I remember how astounding it was.
> What I miss is being able to right click on an item, click "copy public URL", paste it into the browser, and get an exact copy of that item (with nothing else; no image overlays, no ads, nothing).
That still works for me, when replacing dl=0 with dl=1 at the end of the URL (dl = download).
Unfortunately that downloads the file directly, rather than displaying it in browser, so it's not a very nice way of linking screenshots to someone. The other use case is an html file that contains references to images within the same folder, like <img src="foo.png">. You'd want it to display in the browser, not download the html page as a file.
Ah, I see. But that usage is exactly why they don’t permit it anymore, it’s been abused too much. People were hosting whole sites on Dropbox, that’s not what it’s for.
Put <img src="foo.jpg"> into an html file, alongside foo.jpg. In the original Dropbox, if you opened a link to the html file, you'd see a webpage that successfully rendered foo.jpg. So you could use it as a static file host.
Point 3 was not "'viral' or income generating" and DBX pioneered one of the most viral campaigns (give-get) and generates almost $1B a year in free cash flows? How is that vindication?
Their roadmap doesn't exist beyond their one-hit-wonder. CEOs are stepping down because there is no future for the company unless you count acquisition by Amazon or Google or Apple, which will result in the entire company being walked to the grave.
This is really a non-answer. If your point is "Dropbox is a struggling company and therefore all criticism of it ever is fully validated no matter the timeline" then any criticism of any company ever will be validated eventually which is absurd.
It is a darn shame, if the major OS providers didn't roll their own cloud storage, Dropbox could have been the default go-to across the board, and any other competitors that would have risen.
I remember even Ubuntu had their own storage offering, which had they kept it going, I might have subscribed to to this day. Shame, would have been an easy way for Ubuntu to fund itself.
Other users have provided the link, but my heart sinks a little every time I see this brought up, especially when the commenter is singled out by name. People forget that this is a real person. He also happens to be a great HN contributor, and has been for many years.
I realize it's internet fun to point neon arrows at people seeming outrageously wrong in the past, but the truth is that people aren't reading that comment accurately and there's a huge dose of hindsight fallacy here.
When BrandonM wrote "I have a few qualms with this app", he didn't mean the software. He meant their YC application. (Note the title of Drew's post: "My YC App"). He wasn't being a petty nitpicker—he was earnestly trying to help, and you can see in how sweetly he replied to Drew there that he genuinely wanted them to succeed. We should be so lucky for all responses to "crazy new ideas" to be that decent. This community would be healthier, and actually the current thread is a standout example of how far from true it is.
The criticisms he was raising turned out to be a non-issue in hindsight, but were on point in 2007, when the idea of file synchronization was widely derided as a solution-in-search-of-a-problem which only technical users would ever care about, users who (as the comment pointed out) could already roll their own solutions. The idea had recently been publicly mocked in a famous blog post*, so it was on people's minds as the prime example of an idea only technical users would ever care about—and even YC funded Dropbox because they believed in Drew, not the idea.
* described at https://news.ycombinator.com/item?id=23229275
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 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.
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.
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!
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.
It’s funny that you think Dropbox is supposed to let you access lots of files without taking up tons of local drive space. I still think of Dropbox as a file synchronization tool, so taking up tons of local drive space is an expected behavior. It goes to show that people think of Dropbox in different ways.
There was a "major" change in the agent roughly a decade ago. Dropbox went from being a simple folder sync tool to a much more bloated agent that never synced cleanly. I don't know if they just moved away from some modules that were written in C or something, but I gave up on it soon after.
The biggest lesson I learned working at Dropbox was how toxic python is. If you have an unmanageable python code base, and hire Guido himself to help you fix it, he'll dig you into an even deeper hole and then quit. Which honestly was an extension of my experience at Google. When I left Google for Dropbox, python at Google was also in crisis. These two companies cemented my "python: not even once" stance.
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.
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.
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
I too store all my photos on Dropbox. I used Hazel on macOS to move them into YYYY/YYYY-MM folders. I now use a bash script to do similar. This organization system has been rock solid for me for over a decade. I honestly don't want more than that. I dislike the obfuscation so many photo storage solutions use. I want my files and my folders.
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.
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".
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.
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.
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.
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.
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).
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.
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?
A change in long-standing leadership often signifies a change in strategy, whether warranted or not. It’s more likely to deteriorate than to improve the offering, especially given that Dropbox is largely a “finished” product.
That's relevant to the future prospects of the product, but most of the comments are bemoaning the current and previous state of Dropbox. Just seems unrelated to me
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.
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.
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.
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, ..." ;-) ;-)
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.
Think about it. If you're paying all your bills, all your wages, and you have a strong product that people enjoy, and you're able to compete in the market - maybe not gaining any ground, but at least not losing any either - why change?
Of course I moderately understand the market pressures at work, but at some point in the human civilization journey we'll have to be content with something instead of chasing clouds all the time.
In other words, the last time everyone got worked up over this, the trend reversed itself too hard within a few decades, and then reversed itself again. Meanwhile, over half a century after the "decline" started, we have over twice as many people as we had when it started, and the earliest projections for when growth will stop is another half century from now. I think there are a lot bigger problems we'll need to reckon with before then, and if we manage to remain stable by then, it seems like we have good precedent for reversing it fairly quickly.
Surely we're not even close to this point though? I can think of a lot of things that would be incredibly good for humanity to have, and which are achievable with enough economic growth, but which we are currently very far from because our economy does not have the necessary productive capacity (for example, enough solar/wind/nuclear/renewable power to completely eliminate our dependence on fossil fuels)
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"
Is the alternative not likely that they would have spent a decade fighting a losing battle over office software with Google and Microsoft? Paper was a great product but the big guys have vertical integration so companies prefer their end-to-end solutions (GSuite etc) and I don't see how Dropbox could have easily overcome that.
(Given that it was so close to Notion, I think Paper is one area where the product vision was on to something good; but they didn't succeed at product execution, connecting customer feedback to iterating correctly on product improvements.)
I would also if anything put Zoom in with Dropbox, they have a product that is by far the most enjoyable to use in that space, but any other offshoot is not worth it.
Most investors are focused on multiplying their investment many times over, and generating hundreds of millions of dollars in net income a year is not big enough.
And this is one reason why the world is burning (literally and figuratively).
Or do they then turnaround and give them to employees?
If its gone forever, then… why? They just bought something and burnt it? Isnt that like a waste of resources?
The stock market, still to this day is a very very strange thing…
It’s easy to see if you imagine there are only three shares and one of them is torn up. The other two now own the entire company.
It’s a way of giving money to shareholders without the value being realized in the sense of being immediately taxable.
Not in all cases, but many
Which is why GAAP earnings matter and not free cash flow
A huge unforced error though is that the starting price for individual plans is $20/year versus $10/month for Dropbox and Box. At a certain point you have to recognize that the rules of the game have changed. Once a customer has their foot in the door with a cheaper plan that also offers better integration, why would they move to Dropbox or Box?
unless they really want to wait for iOneGDrive to enshittify
Edit: as it stands, sounds like uploading already encrypted files to AWS is the option for privacy hawks who still want cloud - such a small market but think it should grow
Wouldn't that run into the same problem the consumer end has? MS bundles 2TB of OneDrive storage for every user with a M365 license, and Workspace does more or less the same. You can already connect pretty much anything to them as is for pseudo-RAG/enterprise search.
The aggressive bundling from the big players have taken away most of the reasons to pay for Dropbox or box.com and other cloud storage providers.
So Steve Jobs was right: Dropbox is a feature, not a product.
Box is about $115 million income.
I was unclear and I apologize.
Dropbox is one of those companies that did something right, and its kind of sad seeing them in this weird limbo state. I hope they don't wind up crashing down hard before they can finally figure something new out. I think their time to shift from being a "single service / product" style company is long overdue. They don't need to shutdown anything they currently have, but it would be in their best interest to either acquire a smaller complimentary but profitable company, or start building products that compliment their current offering. I really do wonder why they had not done so sooner.
I think they've been doing that, but it's tough to do it successfully. Often the best thing is to return money to the shareholders so they can look for higher returns elsewhere. I think the fact that they're still in business is kind of a miracle considering the competition.
See Microsoft/Office 365. Aggressive bundling means one license gets you literally everything. Sure, it's all mediocre but it checks boxes and is largely "good enough." No reason to go out and buy slack, zoom, box.com/dropbox, 3rd party email gateways, 3rd party EDR, DLP, an MDM, etc. Microsoft will sell you whatever "checks boxes" product you need under one license and cheaper than buying separately.
Sounds like a natural fit as a feature, not a product.
They never tried to expand the TAM. Storage/servers were not rented out while others HuggingFace/Github/Digital Ocean/Cloudflare etc. sold them to expand their TAM.
DropBox & Box have both moved in this direction, but perhaps not aggressively enough? I'm thinking in particular about e-signing, where DocuSign has a market cap roughly equal to the sum of DropBox & Box. Both have e-sign products; I am fairly certain that I have never encountered either in the wild despite routinely being sent other e-sign links.
AI is perhaps another emerging opportunity. Instead of uploading documents to a dumb pipe, let me have the pipe do things to them. Dumb, simple example would be I can put PDFs in a folder and after a one-time setup, I can share an API link that lets my users extract specified data from those PDFs via secure JSON API. Or simple CMS instead of WordPress. Or analyze documents flowing through a folder for x, y, z anomalies and alert me.
The thesis is that they should survive and thrive as an investment asset through the AI bust, but performance during the AI bubble is poor. If you are a longer term investor then B2B SaaS valuations appear cheap right now, but you need to be able to weather the storm of missing out on the AI infused bubble.
As evidence the BVP Nasdaq Emerging Cloud Index is at all-time lows for EV/revenue multiples. While some of the companies will see growth rates impacted by AI, that only explains a little bit of the drop in multiples versus the past.
Yeah, with blinders on, it's hard to see that. Otherwise, the playground was wide open. If whales start eating your revenue, then you go after them.
So I wouldn't say it's the market per se. It's just that network storage has become commoditized. Storage tied to Google, Microsoft or Apple is always going to have a market advantage.
just a thought for you people.
It is similar to saying that most websites are just cloud-hosted SQL rebranded.
you can build object storage on FoundationDB + other awesome bespoke stuff.
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?
This is wild phrasing.
Anyway, I reached out to their support for help and they were utterly useless. I had a couple weeks of back and forth with them before giving up. I hope I never actually need those docs.
I hope you have a better outcome than I did.
I really wish more people understood this, especially on HN.
Account recovery flows are flooded with people trying to break into other people's accounts. It's going to be nearly impossible to make a system that can allow someone to recovery their account without also accidentally allowing someone to social engineering their way into someone else's account.
It was two hyphens --
It was two hypens --
The description was that the card was good for gaming or “turning dinosaurs into clean money”.
Banned permanently and no way to ever reach a human.
I sold a rifle legally on an online auction site. The buyer was offered to pay with PayPal they were given the option to use. The buyer took that option, making me break PayPal TOS.
Banned permanently and no way to ever reach a human.
Banned from Venmo, absolutely no idea why. SO banned from Venmo, absolutely no idea why.
Banned permanently and no way to ever reach a human.
Fuck. Big. Tech.
Prior to 2013 or after? Maybe they merged ban lists with PayPal (who owns them).
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.
(at least this was the ambient understanding internally when I worked there a few years ago)
While not everyone values that, I suspect that enough people do to warrant Dropbox’ existence.
Generally it is impossible to understand Dropbox's strategy if you think about individual purchasers as significant. Iirc they mostly serve as a marketing funnel for team- and business-sized contracts. (although this varies from year to year, sometimes they do focus on e.g. family plans for revenue)
if they lose these corporate contracts, it should still be a viable (if much smaller) business Thank you for clarifying that if Dropbox loses their biggest customers, they will be a much smaller business. what a big genius we have here.
In other words, it wouldn’t force Dropbox to entirely stop existing. another brilliant stroke of genius. if mcdonald's closed all their stores and only existed in airports, they would not disappear entirety but possibly continue to exist? fascinating.
truly you are a messiah among animals
There used to be many more - Sugarsync, AeroFS, Syncplicity, just to name a few - all bit the dust. Box.com found a niche serving business document flows; Gdrive, iCloud, OneDrive, all survived thanks to being features in a broader Big Tech suite. Everybody else? Outcompeted, plain and simple. Dropbox was just a cut above.
(I used to work at one of the companies named above, so although it's just one person's opinion, it's at least as informed as anyone else's here :) )
OneDrive for Business and OneDrive Personal are two different backends. I'm guessing that you're using the "Business" version?
I even use rclone to sync photos to OneDrive I can then share with family/friends.
https://knowledge.workspace.google.com/admin/storage/buy-mor...
This is more than S3 charges, but S3 will nickel and dime you aggressively for using that storage depending on your use case.
But $22/month buys an entire Google Workspace seat, which includes 5TB, for an effective $5.50/TB/month, which is quite a good deal. On the other hand, it’s rather lacking in flexibility.
I find this all somewhat confusing. At least one of these offerings does not reflect the underlying cost of the product.
Personally, I dislike that you cannot restore an older version of a file on laptop/phone, and must instead use their web app, for which you need to disable ADP, which defeats its purpose.
For business purposes I didn't want to use iCloud. But it seems like it's iCloud & Dropbox then.
I paid for Dropbox for a long time specifically because it was an independent option, but over time the feature bloat annoyed me more and more, and their dabbling in genai stuff was the last straw. Now I use syncthing over wireguard tunnels.
I've been trying to use it for a massive tree of ~250k files across ~500k folders, which only needs to live on one device at a time and sync to a backup in case it dies, and even if I tell it send-only/receive-only explicitly, it regularly seems to go cross-eyed at some change made in the folder structure and give up and rescan and hash everything, and if anything in the tree changes while that's happening, it gives up and just marks it a conflict to be manually resolved...or silently hangs until I restart it.
Why not keep using B2? You didn't mention why you were leaving that platform when it seems like a decent solution to your problem.
If you want to minimize drama, it's worth still paying for Dropbox.
Good pun!
Business Strategy 101 teaches that broadly speaking, there are 3 categories into which companies fall, which are cost leadership, differentiation, or segment focus.
If, as you say, your only pain point is the cost of dropbox, then any potential alternative would be competing to be the cost leader, and cost leadership strategies are unattractive for startups. Nobody is investing in early-stage companies building "a cheaper clone of XYZ". It's hard to attract startup talent to "a cheaper clone of XYZ". It's rarely fun for founders to build "a cheaper clone of XYZ".
Unfortunately I think there are limited avenues for successful differentiation in the file sync space. Self-hosted vs cloud, standalone vs OS-level integration, cross-platform vs not? Can't think of much else off the top of my head, and I think big players are able to throw shitloads of engineering talent at OS-level integration features (and that gets you iCloud, basically).
Beating dropbox at their own game wouldn't be impossible, but I think that's why there aren't many competitors in that space.
Yep, this is why cost leadership strategies tend to be unattractive to startups. Finding ways to be meticulously frugal just isn't exciting to most people, I would think.
(that said I'm just an engineer parroting things I heard while working there, I wasn't involved in any actual strategy)
Local backups are important, they're cheap, and often fast. They just shouldn't be the only kind of backup you do for data that is important to you.
Edit: Read the comment below, it's information I should have included in the first place. It's important to note that the comment was helpful at the time, and only became a meme later.
https://hn.algolia.com/?dateRange=all&page=0&prefix=true&que...
Of course, that doesn't make them money. But millions of users that then had all their files there and kept using it when no longer students (so paying), and recommended it to their places of work etc.
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 techniques to sell it.
You're cherry-picking your "technicals". The click wheel hardware and software implementation (especially the UI response time) was (and still is) revolutionary.
iPod won on the technical merits; just not the ones you're focusing.
Better than all? No certainly not, Apple's build quality loses out to plenty of much more premium products. But it generally sits head and shoulders above the average build quality of any given product category, which seems to be the niche they most aim for: "the upmarket version of the common offering." That ones that immediately come to mind are Macbooks and iPads.
You can find a laptop that is better in one aspect, but it will be worse in others.
Absolutely no-one is concerned today about what happens when you dip out of connectivity because fast mobile connectivity was not abundant in 2007 (the iPhone was only released that year), which obviates the "this will never replace a USB" criticism. Mobile made a whole new class of businesses possible.
https://news.ycombinator.com/item?id=599852
It would be nice if that still worked. My resume exists in an iCloud drive, and I spent ten minutes on my phone trying to figure out how to attach it to a gmail message before giving up. "Copying" a file isn't even a well-defined operation anymore. (Or at least "pasting" doesn't always paste it.)
You can also just go into the files app, tap and hold, tap copy, go to Gmail tap and hold in your draft email, tap paste.
There’s other paths that work too, like hitting the “send to” logo in files and then selecting Gmail.
It’s really the exact same patterns I might use on a computer for the most part.
Still, copy-pasting a file should work. It's unclear what "copy" even does.
I assumed this was a solved problem before Windows 98 (first desktop OS I used), but Apple cannot get this right 28 years later.
https://news.ycombinator.com/item?id=4611830
Around 2005, I was hired by a company that was building software for USB drives, to build a porn site.
Turns out, they wanted me to build a poc for an authentication solution: some USB drives would have a fingerprint reader and they wanted to build this auth system based on that.
So I built that, but "perplexingly", they didn't get any finance or enough prospect customers, so the project got shelved.
Then, I was handed another project they had on the back burner, a sort of firewall for devices, meant to prevent exfiltration of company documents on unapproved USB drives.
I built the single user version, eg you had to be admin to allow devices and the product sold quite well, even winning some prizes iirc.
We started getting requests to have a centralized admin interface and a way to allow/disallow copying some file types. I started working on the centralized admin and the company hired a very talented engineer to build the file filtering thing. This last thing was based on a windows API that allowed for virtual file systems. Things were ticking along nicely and the company even hired a business manager to try to come up with other products we can build with our existing tech.
One afternoon, over a bunch of cold beers, to link with the hell on earth that happens right now in London, me and this person came up with a cunning plan! What if you sell an 1GB USB drive with an extra 1GB of space?
The plan was simple: plug in the device, you get a drive that's the regular USB drive, but also another drive, backed by the virtual file system thing and a version of my http auth thing, and you would read/write from a server on the Internet.
Big boss liked the idea and I started researching how to get servers and the like, while a third engineer was tasked to build the desktop app needed.
It all came crashing down, days later, when this engineer declared that is not possible to have a windows app minimize to sys tray and the project got cancelled. I left the company not long after that .
This was the story on how a small German-Romanian company could have beat Dropbox.
The tool strangely still has a certain something that I reach for from time to time. Cross-platform(cross-era even, I just used it to move something off an ancient Windows 10 install), painless sync, painless auth, painless sharing(or not), painless updates, simple billing that isn't so high I have to factor it into my plans, and the app doesn't try to ramp my price based on how many devices I access my data from. It's just a good piece of software at a good price.
Commercially they did just fine as well according to the article: $6B in market cap, $2B/yr rev and $2B personally for Drew. Maybe not the top of YC leaderboard, but well above average.
I want more services like this one, and will keep paying for my modest storage amount until they tell me to go.
I still use it for NetSBD source
I use FTP mirrors for various source code
I use FTP for moving files to and from mobile phones
I have never used Dropbox. That company made some people wealthy no doubt but that doesn't help me
I also use USB sticks extensively, e.g., primarily for booting computers, but also for data storage
I have broken a couple when using them in non-NetBSD OS but never lost one
but I think there are many people out there that love a gui for storing files in the cloud. i know my parents/parents friends' all use it.
Dropbox helped here. They had a Linux client and a Mac client and kept both in sync.
Mine was somewhat of a niche use case. I think every one who cycled between Linux and Mac for their daily work back then thought - yeah I can definitely use those tools but an automatic sync would be nice.
What Dropbox didn’t have was a moat that comes with android or iOS. I use iCloud now since my need to move between different devices doesn’t exist anymore.
I have a subscription which I want to cancel but can’t because there are other users. Basic features require upgrading.
The crazy part is, you pretty much can just do this yourself now, simply by pasting the famous HN comment into a good agentic AI.
While I understand and respect DanG's perspective as well as the original poster's, that comment is never not going to be funny and I'm unwilling to pretend otherwise. That said, everybody who revisits the Dropbox comment thread for a laugh really should take some time to read the rest of it. It represents a high-water mark in HN comment quality, as well as an interesting harbinger of future star power in the startup community. Some other people participating in that thread ultimately did good work and made a name for themselves, not just Drew.
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.
Honestly that's what I love about it. I work on something on my desktop. Then when I go to my laptop, everything is there too. It's great. When I get another computer I can just enable Dropbox, walk away, and all my projects, notes, pictures, etc. will be there. I pay them some amount of money per month and it just works and I very rarely need to visit the website or even click on the icon in my toolbar.
Sometimes I read notes on my phone and it's kind of annoying that I can't search through text using their app, but I generally consider that to be a problem with Android rather than Dropbox.
For me that and end-to-end encryption (I know it's supported for teams now).
Instead they just added more annoyances over time. Every time I logged into the web interface, I would get stupid upselling advertisements (maybe don't badger your paying users with that nonsense)? I replaced the official client by Maestral years ago, because they switched to embedding a web browser, and the AFAIR the client was also trying to do upsells.
My wife were and I were customers for years. But we finally decided to terminate our subscription last year. Mostly because of the constant upgrade nagging + the orange guy taking office and Dropbox not providing E2E encryption on family accounts. So we switched to Proton Drive. It's worse in many ways, but at least it's E2E encrypted and doesn't shove upgrading ads in our faces all the time.
It's sad, Dropbox was really a great product.
Man. 1Password is another example of this. They've chased growth and no longer seem to be able to build a browser extension that actually works. I've been seriously considering dropping 1PW because of it.
That’s also what I care about, but the atrocious client (and the m1 thing) and the constant nagging in the web interface was too much. I cancelled and now use a mixture of icloud, airdrop, and rsync/sftp with remote servers.
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.
If you add raw=1 to the URL then it will directly show in the browser without the Dropbox viewer.
Or did you share a folder?
When a company like Dropbox prioritizes user account growth over usability, that company debases itself and deserves to lose.
Or maybe I just click those headlines at a higher rate..
It's frankly depressing how few places there are to have quality conversations, particularly for general tech.
Yeah I used to learn so much across quite a few forums. Most of those communities are dead, dying, filled with bots or filled with people making shit up/just posting lousy jokes now. A lot of folks have jumped to Discord, which frankly, isn't for me, so feeling a bit lost on where to surf these days
Is there anything this simple now? What I miss is being able to right click on an item, click "copy public URL", paste it into the browser, and get an exact copy of that item (with nothing else; no image overlays, no ads, nothing).
In the limit case you should be able to use it as a webhosting service for static files, since visiting an html page in a browser serves that file and relative links are preserved.
I guess it's a losing value proposition, but it sure would be nice.
It's unfortunate the original demo video was lost to time. I remember how astounding it was.
Is this the video you're thinking of?
https://web.archive.org/web/20070407145348/http://www.getdro...
There was a recording of a presentation Drew gave later on about Dropbox, but it wasn't as good. This is definitely the original.
Thanks for the memories!
That still works for me, when replacing dl=0 with dl=1 at the end of the URL (dl = download).
You have described Google Drive.
Put <img src="foo.jpg"> into an html file, alongside foo.jpg. In the original Dropbox, if you opened a link to the html file, you'd see a webpage that successfully rendered foo.jpg. So you could use it as a static file host.
>Our business is in a stronger position than it's been in years
>What’s energized me most since joining Dropbox is the connection people have with our brand
>It gives me a lot of confidence in what’s ahead for Dropbox
All corporate fluff, no actual content.
Then they crippled the free plan and Apple and MS started pushing their services hard. And Dropbox seemed less ubiquitous after that.
from: https://news.ycombinator.com/item?id=27067281
More: https://hn.algolia.com/?dateRange=all&page=0&prefix=true&que...All the best to their employees, but I think a big round of layoffs will be coming within the next couple of quarters.
I feel like they left a lot of money on the table.
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!
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.
I'm all-in on the apple ecosystem, so while it's not perfect, iCloud storage works better. Was a shame, though.
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
Drew launched a great new product, fine tuned it to be one of most loved and then made profitable company. Respect
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.
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.
[1] https://www.quora.com/Why-do-most-people-like-Dropbox
Jobs was ultimately right in the end.
Just musing....
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.
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.
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
[1] https://news.ycombinator.com/item?id=9224