Dropbox CEO Drew Houston to step down

(cnbc.com)

127 points | by aghuang 5 hours ago

27 comments

  • gigatree 1 hour ago
    Board finally realized people can just do this themselves with FTP/SVN/rsync and curlftpfs
    • jedberg 1 hour ago
      For the uninitiated: https://news.ycombinator.com/item?id=9224

      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.

      • tptacek 33 minutes ago
        Important to note here that Dan has been for years asking people to understand this comment in the context of the time and circumstances it was written. It's not a dunk on Dropbox. It's not the "less space than a Nomad" iPod comment on Slashdot. It was helpful and constructive criticism for Houston's YC application --- very specifically the application itself.

        https://hn.algolia.com/?dateRange=all&page=0&prefix=true&que...

        • matsemann 25 minutes ago
          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.

        • dingaling 13 minutes ago
          > "less space than a Nomad"

          I actually thought that was a valid comment, more so than the Dropbox one. The contemporaneous iPod _was_ technically and acoustically inferior to the Nomad.

          The iPod "won" on account of fashion, style and marketing. Yes, the Slashdot comment was naive in underestimating or ignoring the power of Apple, but objectively it wasn't wrong. Apple released an inferior product and used out-of-band techniques to sell it.

          • tptacek 3 minutes ago
            It's a category error to compare the two comments at all.
        • FergusArgyll 2 minutes ago
          The first Bitcoin thread is great

          https://news.ycombinator.com/item?id=599852

      • sillysaurusx 58 minutes ago
        > Most people I know e-mail files to themselves

        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.)

        • dghlsakjg 52 minutes ago
          It’s literally: click the paper clip logo in Gmail, tap files, pick your file.

          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.

          • matsemann 33 minutes ago
            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.
            • Semaphor 11 minutes ago
              That sounds like some kind of weird google interface issue. Maybe try using IMAP or POP or whatever standard they still deign to support.
          • sillysaurusx 32 minutes ago
            Thanks. I saw Photos and Drive, and apparently I missed "Attachments".

            Still, copy-pasting a file should work. It's unclear what "copy" even does.

        • genxy 54 minutes ago
          When you get stuck in a task like this, you realize that civilization will collapse with a whimper.
        • watermelon0 48 minutes ago
          Sharing files between apps and file management in general on iOS is atrocious.

          I assumed this was a solved problem before Windows 98 (first desktop OS I used), but Apple cannot get this right 28 years later.

          • mananaysiempre 21 minutes ago
            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.
          • amluto 46 minutes ago
            At least there is a Files app these days, and many iOS apps interoperate a little bit with “Files”.
      • defen 19 minutes ago
        If OP hadn't written his reply to 'dhouston 19 years ago I for sure would have flagged it as LLM-generated.
        • jedberg 13 minutes ago
          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!
          • gigatree 3 minutes ago
            IMO the only solution is to just upvote things if they’re interesting or useful and downvote them if they’re not
      • Ologn 53 minutes ago
        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)

        https://news.ycombinator.com/item?id=4611830

    • kenjackson 39 minutes ago
      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...
    • orochimaaru 15 minutes ago
      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.

    • 1vuio0pswjnm7 25 minutes ago
      Don't forget CVS

      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

      • BorisMelnik 15 minutes ago
        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.

    • TwoNineA 45 minutes ago
      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.
    • mv4 54 minutes ago
      Only took 19 years!
    • davidmurphy 35 minutes ago
    • bachmeier 54 minutes ago
      The upcoming Claude Brandon release will make Dropbox obsolete.
    • seydor 55 minutes ago
      Or maybe he did
    • savrajsingh 46 minutes ago
      "...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"
  • joshmn 0 minutes ago
    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. :(

  • browningstreet 1 hour ago
    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.

    • ajkjk 48 minutes ago
      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)

      • layer8 8 minutes 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.

    • caconym_ 36 minutes ago
      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.

      • rincebrain 32 minutes ago
        How have you found syncthing's scaling?

        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.

        • caconym_ 7 minutes ago
          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.
    • packetlost 58 minutes ago
      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
      • idatum 12 minutes ago
        But you can just use any cloud blob storage provider (including the big ones) along with the rclone utility. rclone supports many.

        I even use rclone to sync photos to OneDrive I can then share with family/friends.

      • jsmith99 39 minutes ago
        OneDrive used to be rubbish but nowadays it's reliable. We use it at work and I don't feel any pressure to move to Dropbox. It's also much cheaper.
        • packetlost 38 minutes ago
          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.
      • amluto 45 minutes ago
        Google Drive has gotten inexplicably cheap for Workspace users, too.
        • svara 34 minutes ago
          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.
        • dawnerd 41 minutes ago
          They've raised prices a lot over the last few years while reducing the storage you get.
          • amluto 34 minutes ago
            The pricing is weird. If you want to buy à la carte storage, it appears to be $40/TB/month for business and $30/TB/month for enterprise:

            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.

      • sssilver 48 minutes ago
        What's the issue with iCloud?
        • watermelon0 42 minutes ago
          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.

        • browningstreet 48 minutes ago
          Mounting Dropbox on Linux machines is really easy. Google Drive has terrible support for binary files and namespaces.

          For business purposes I didn't want to use iCloud. But it seems like it's iCloud & Dropbox then.

    • eikenberry 19 minutes ago
      > Having just rsync'd 100s of GBs back down from B2 and not sure where to put 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.

    • debo_ 20 minutes ago
      > With their block level syncing, Dropbox is still not really replicated

      Good pun!

    • stackghost 49 minutes ago
      >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.

      • ajkjk 47 minutes ago
        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.
        • stackghost 41 minutes ago
          >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.

          • ajkjk 37 minutes ago
            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)

    • 1970-01-01 54 minutes ago
      You could just put it on a local disk? 512GB sdcard is like $15 at Walmart.
      • dghlsakjg 48 minutes ago
        Check the price of flash memory again. That $15 card is almost certainly a scam.
        • matsemann 30 minutes ago
          At least if bought from Amazon. It will happily accept writing 512 GB to it, but it's not stored anywhere.
          • irishcoffee 14 minutes ago
            Yep that burned me once. Lesson learned.
        • dawnerd 40 minutes ago
          Yeah their memory of how much memory costs is outdated. I was just at a walmart this weekend and a 128 card was 30 bucks.
      • browningstreet 48 minutes ago
        I wanted a forever backup. I'm going to trust Apple and a hard drive.
        • lostlogin 32 minutes ago
          Ah yes, the famously reliable Time Machine.
      • ThePowerOfFuet 37 minutes ago
        Tell me you have no interest in your own data without telling me you have no interest in your own data.
        • 1970-01-01 12 minutes ago
          How is a local copy not the best way to store data?
  • bhouston 3 minutes ago
    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 Salesforce? 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.

  • postalcoder 56 minutes ago
    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.

    • MiddleEndian 31 minutes ago
      >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.

      • postalcoder 26 minutes ago
        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.
        • MiddleEndian 20 minutes ago
          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.
    • microtonal 43 minutes ago
      All I care about is packrat and good syncing.

      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.

      • plasticsoprano 38 minutes ago
        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.
    • al_borland 40 minutes ago
      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.
      • postalcoder 37 minutes ago
        > 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.

    • skydhash 7 minutes ago
      > All I care about is packrat and good syncing.

      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.

  • njt 51 minutes ago
    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.

    • aeyes 38 minutes ago
      But you don't need a Dropbox account to view any file for which you created a shareable link.

      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?

  • georgel 1 hour ago
    • arealaccount 55 minutes ago
      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..

      • brittlepeanut 46 minutes ago
        [flagged]
        • malfist 34 minutes ago
          Says an account 13 minutes old.
          • nathanmills 31 minutes ago
            Wow, that means 13 minutes ago must've been the first time they've ever used the site
          • antinomicus 28 minutes ago
            Yeah, what? Increasingly worried this site is bots talking to bots.
        • supern0va 37 minutes ago
          And yet, it somehow has significantly better conversations than most places online. Maybe on par with reddit 10-15 years ago.

          It's frankly depressing how few places there are to have quality conversations, particularly for general tech.

          • ricardobayes 27 minutes ago
            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.
          • jsbisviewtiful 27 minutes ago
            > 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

    • sillysaurusx 1 hour ago
      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.

      • layer8 3 minutes ago
        > 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).

      • al_borland 22 minutes ago
        > 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...

        • sillysaurusx 14 minutes ago
          Yes. Holy crap, you actually found the original.

          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!

      • tyler71 34 minutes ago
        pcloud with the public folder works well. I've uploaded a few html ebooks with relative routing and it has worked fine.
      • jeffbee 1 hour ago
        > right click on an item, click "copy public URL", paste it into the browser, and get an exact copy of that item

        You have described Google Drive.

        • sillysaurusx 57 minutes ago
          Not quite; it's not a direct link to the item.

          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.

          • georgel 34 minutes ago
            It was such a nice feature too, but very easily and quickly abused.
    • 1970-01-01 57 minutes ago
      It was quite a stupid and expensive ride, but they were vindicated, especially on point 3:

      >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.

      • urams 39 minutes ago
        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?
    • giancarlostoro 1 hour ago
      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.
      • ADent 37 minutes ago
        They were seemingly everywhere and lots of apps and services offered Dropbox as an option. 200 million users in 2013.

        Then they crippled the free plan and Apple and MS started pushing their services hard. And Dropbox seemed less ubiquitous after that.

    • pikseladam 1 hour ago
      i didn't expect to laugh when i enter news today :)
      • ignoramous 58 minutes ago
        Daniel Gackle thinks BrandonM's is most probably the most misunderstood comment in news.yc history.

        from: https://news.ycombinator.com/item?id=27067281

          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
        
        More: https://hn.algolia.com/?dateRange=all&page=0&prefix=true&que...
  • hylaride 55 minutes ago
    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.

    • matsemann 18 minutes ago
      It was python from the start ( https://news.ycombinator.com/item?id=8892 ), but maybe the 2to3 migration, or just a general rewrite you're thinking of?
    • jeffbee 44 minutes ago
      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.
  • farcaster 38 minutes ago
    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.
  • ivraatiems 54 minutes ago
    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.

  • aresant 53 minutes ago
    Prior to Dropbox I carried a small-form-factor case back and forth to work every day because file syncing was such a train wreck.

    Seeing the original HN post was an epiphany and my quality of life before/after was forever changed.

    Yes there's been feature creep, yes there's been monetization but as a cross platform, standalone file syncing experience I've been a happy paying subscriber for nearly 19 years and counting!

  • thm 4 minutes ago
    So, Web 2.0 is finally over now?
  • jaredcwhite 31 minutes ago
    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".
  • victorkulla 14 minutes ago
    Oh - so you disagree with my comment- so mark me down instead of actually formulating a concise rebuttal - cheap.
  • sidcool 58 minutes ago
    Is he the next Member of Technical staff at Anthropic?
  • unpopularopp 43 minutes ago
    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
  • kasperset 35 minutes ago
    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.
  • arbirk 45 minutes ago
    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.
  • jabedude 35 minutes ago
    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?
    • toephu2 32 minutes ago
      Because there is PR speak, and then there is reality.
  • ecommerceguy 53 minutes ago
    call me crazy im still using a 100gb box account from when i bought an hp touchpad. that thing was so cool.
  • zengid 43 minutes ago
    Drew was CEO for almost 20 years right? that's a heck of a run!
  • toephu2 31 minutes ago
    As Steve Jobs famously told Drew Houston...they had a "feature, not a product."

    Jobs was ultimately right in the end.

  • krashidov 46 minutes ago
    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.
  • vednig 55 minutes ago
    I wish Drew all the best for his journey, he built the market for many generations to come.
  • wwweston 57 minutes ago
    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.

  • victorkulla 33 minutes ago
    Really? Who cares?
  • semiinfinitely 46 minutes ago
    dropbox still exists?