Dropbox CTO Resigns | Hacker News Reader

Dropbox CTO Resigns

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114 pointstpw212128 comments

Dropbox has slowly but surely gone from a product I enjoyed and recommended to one that I actively dislike using. I find it pretty astonishing that such a mature product:

- Is slow

- Demolishes my MBP's battery

- Has not gotten simpler to use

And worst of all, it is completely out of line with what their competition are charging. They want $12.50-15/mo for their most basic plan when their competition is charging $0-10 for their core feature set.

I wish them well, but once iCloud launches file sharing I'm 100% done with them.

Steve Jobs was early, but not wrong about Dropbox being a feature and not a product. I just want a folder that syncs extremely reliably, that's it. They've gone down the corporate rabbithole and now call themselves a "smart workspace" whatever that means.

Maybe, but a feature that works is worth more than a product that doesn't. Dropbox always works, everywhere.

I'm old enough to remember a world pre-Drobox (and pre-high bandwidth). I used to work at different places. I kept a laptop in each office, and carried with me Iomega disks that I synced every morning. It was slow and complex and error-prone.

Alternatives from either Apple or MS will never work as well, they will always favor the platform they come from (if they don't eventually drop the others).

It's not an overstatement to say that Dropbox changed my life; here's to hoping it never goes away.

“Dropbox always works, everywhere.”

This used to be true, but has gradually become less true. Linux support has certainly taken quite a dive.

They also removed features I really liked. I used the Public folder a lot :(

(I actually used to pay for Dropbox, because I genuinely thought it was a great product. It’s still probably one of the best syncing services, but at this point I’ve just moved off of syncing services.)

Yes, this. Them ending support for ecryptfs filesystems (they used to support it) is the main reason I'm considering ending my subscription soon. They took a massive step backward there and I am not happy about having to move my entire Dropbox directory to an unencrypted part of the filesystem.

They rolled back those changes - they support quite a few filesystems again now. See the Linux section of https://help.dropbox.com/installs-integrations/desktop/syste...

Oh awesome, thanks. I'll test that again and if it continues to work with my encrypted filesystems, I will probably stay a paying customer.

> Dropbox always works, everywhere.

Nope. My 2-3 windows installs fail way too often. And totally silently. And don't restart. Had to drop from the paid version to bare minimum and move to Syncthing which for me works far better at the cost of more options to config.

Microsoft has been supporting the Mac since 1985. I doubt very seriously that it will be dropping support for OneDrive for iOS or macOS in the foreseeable future. MS has been quick to support new relevant APIs as they are introduced by Apple.

Well the corporate rabbithole was the only way they could turn it into a business, and not a feature as you say.

Only if they wanted VC expected growth..... they could have just stopped adding new features, only had a few employees, and continued to make money charging a small amount for their single feature.

It’s very hard to have solid product, engineering, marketing, sales, and support on any scale without taking VC money.

Backblaze and Basecamp have, to name two.

Backblaze does have one VC backer, but they aren’t pushing for exponential growth.

https://news.ycombinator.com/item?id=21016598

They are cash flow positive though.

https://news.ycombinator.com/item?id=21006216

TIL. I thought they were entirely bootstrapped.

Yeah. I learned that after he responded to one of my posts....

Yev here -> yes, we have one VC backer from 2012. We wrote a post about it that sheds a bit of light on why (Thailand flooding played a major role): https://www.backblaze.com/blog/backblaze-raises-5-million-wh.... TL/DR we have a capital-heavy business and the $2.5m cash infusion helped us weather hard drive prices going up 3x overnight.

This is very relevant to the discussion about Dropbox - which I really don't expect you to respond to being they are sort of a competitor (yeah I know -- not really https://www.backblaze.com/blog/sync-vs-backup-vs-storage/). But, how BackBlaze decided to run their business (bootstrapping) and how Dropbox decided to run theirs (VC backed early on and still not profitable), is the perfect example of how taking on VC funding rarely leads to a good long term customer focused outcome.

Also of note, unlike Dropbox, Backblaze was able to release a new slightly more enterprisey product - B2 - without losing focus on the main product.

On the other hand, it does take a certain amount of 'privilege" (yes I hate that word, couldn't think of a better one) to have five founders who could afford to not take a salary for a year....

But one criticism, any time you post a link to the Backblaze blog it should come with a warning. It quickly led me down a TVTropes type rabbit hole of reading more interesting articles.....

> It quickly led me down a TVTropes type rabbit hole of reading more interesting articles.....

Hah! That's a good thing! As for VC vs. Bootstrap - our five founders all worked together previously at a company that raised VC funds and while they weren't made millionaires from that company, it did give them enough cushion to go without salary for a bit. Originally it wasn't supposed to be 2 years though, so when it started to drag out there were definitely some...uncomfortable times, but they pulled through them. That's not say that we HATE the VC model - it definitely works for a lot of companies out here, but there is something nice about being able to choose your own adventure.

Re: Dropbox as a competitor -> You hit it, they kind of are, but I think that's mostly because people don't really know enough about how things work to tell the difference. Part of what I do with the Backblaze consumer service is a lot of education on why you should use both :)

Appreciate the context in this thread. Keep on being awesome.

not really necessary to have a solid product, on the contrary. VC money bring unreliable and not always user first agenda.

I’m seen really solid products go out of business while competing with inferior products with better marketing/sales.

That's true, but it also means their product is no longer the feature I want or signed up to.

They can do what they like with their business. But I, like jonknee upthread, don't want their new changed thing, and an=m somewhat disappointed at having the feature I'm subscribed to turn into a product/business I would not have subscribed to if they'd told me up front.

That's probably because shareholders and investors blindly want unbounded growth while customers want them to just work. It's sad but the venture capital and public market ecosystem cannot support a lot of awesome things like Dropbox.

My favorite Dropbox feature is folder point in time restore. It saved my hide a few times.

Dropbox has slowly but surely gone from a product I enjoyed and recommended to one that I actively dislike using.

Over that same time period, they have gone from being a consumer product to an enterprise product, because the money in file sharing software is in enterprise. Slowness, battery use, complexity, none of these are as important to Dropbox nowadays as they used to be, because they are not as important for enterprise sales.

Swimming with the big fish is flawed from the start. Why do businesses use one drive? Because they have enterprise office and outlook for their email, and one drive was thrown in. Why do businesses use google drive? They use the google suite and gmail for their email and google drive was thrown in.

If dropbox wants to compete with enterprise software they'd need to reinvent the office/g suite AND email services. They tried the former with dropbox paper, but it's clear that they've bitten off far more than they can ever chew, especially when your direct competition is google and microsoft.

Office 365 for personal use is $80 a year and comes with OneDrive with a total of 6TB of storage - 1 per user.

Unlike Dropbox, when you use a shared folder, it isn’t subtracted from your storage.

And then the random client limit to 3. I've stopped using them since then.

I did as well. I actually wouldn't have been opposed to paying more for more clients, but they wanted $20 a month for a ton of space, which I didn't need. There was no in-between.

I switched to OneDrive which as actually been really amazing, even on Macs & iOS devices.

> once iCloud launches file sharing I'm 100% done with them.

Do you mean something other than this? https://support.apple.com/guide/mac-help/share-files-with-ic...

Perhaps parent commenter meant folder-level sharing which is slated to be introduced in iOS13.x / macOS 10.15.x.

Ah, very cool, I guess I missed that announcement.

They mean folder sharing, which is coming in Catalina.

Which is going to be great, except for the older MacOS devices I have which won't update to Catalina. My old MacMini file/media server is doing a sterling job, in spite of having been left behind by Apple.

Lucky cron and rsync is still a thing...

For a Linux user, you can already build such a system yourself quite trivially by getting an FTP account, mounting it locally with curlftpfs, and then using SVN or CVS on the mounted filesystem. From Windows or Mac, this FTP account could be accessed through built-in software

In all seriousness, have you looked at OneDrive + Office365?

For $70/year you get 1 TB of storage, a client that works on all platforms, plus Microsoft Office 365 (online) and two licences for the desktop install of Microsoft Office plus the Office apps for iOS/Android. It's a great deal and works well.

Doesn't work on Linux which is what the quote you're referencing is talking about. Office365 comes with it's own challenges. Plus your documents are all scanned and there is no privacy protection, especially not from the US government.

Dropbox is a US company, I don't see how you get better privacy protection there. Plus Microsoft has a petty good track record, they've challenged US government requests for information in court, and fought to prevent the government from accessing data stored outside the country.

Dropbox has equal access to your files as Microsoft does. Which is why Syncthing/Bittorrent sync is very useful.

It's also limited to just being a shared folder feature.

I moved myself to this, along with the family plan ($99/USD/yr, IIRC). The nice thing is that you can still buy the Office suite separately if you want. The other thing is I finally wanted to settle on "one" cloud storage provider for me and my family, so the addition of OneDrive sealed it when combined with Excel.

Honestly, Office365 is something of a model for the SaaS software I've bought: the core offering (Office) is still available with an eternal license, but the SaaS offering is very good, well priced, and the value add of OneDrive is great when competitors charge for storage separately. There are a lot of issues with SaaS (velocity, feedback loops) but they did this one right, I think.

(The funny thing is I have an iPhone and almost exclusively use Linux, so obviously I live in a bizarro world.)

That $70/year gets you the 1TB of storage and everything else you mention, per person, for up to five people. That's a total of up to 5TB. Perfect for a family.

(at least, that's the standard offering here in Europe...)

I agree, best deal going. Also, I really appreciate the web app versions of the Office apps for use on Linux.

Also getting up to date Office apps on iOS, iPadOS, and macOS is valuable to me even if cumulatively I only use them two or three hours a month.

What if you want more than 1 TB?

I've not found any option to purchase more storage for a non-business Office365 account.

Office 365 is $99 a year for 6 users each with 1TB. You can create another user and share their 1TB with your primary account.

It doesn’t work like DropBox, the shared space is added to yours. With Dropbox, any shared folders are subtracted from your allocated space.

Upgrade to the family plan for $99 for 6 TB.

> Dropbox has slowly but surely gone from a product I enjoyed and recommended to one that I actively dislike using. I find it pretty astonishing that such a mature product:

That's what happens when the "Enterprise sales" mosquito bites a B2C company.

Sounds like a perfectly classic version of the growth trajectory characterized in "Innovator's Dilemma" (Clayton Christensen). Company grows into a big fat dinosaur, leaving a soft underbelly for a scrappy little mammal to claw at.

Except in this case the scrappy little mammals are big fat dinosaurs themselves.

It’s a continuous process.

My main issue with Dropbox is that the UI got lighter but not more useful, and I found some anti-patterns trying to share something with my friends without them being signed in dropbox.

> once iCloud launches file sharing

As an iPhone and MacBook user I'd have happily done that iff it was useful or accessible to my friends and family who are not in the fruit company ecosystem (and that's the majority in my case).

Because I really don't think Apple is going cross platform anytime soon https://support.apple.com/en-us/HT204174 https://support.apple.com/kb/ph2609

You just posted a link for how to setup iCloud on Windows.

I agree that support on other platforms hasn’t been great.

> To use iCloud, you first need to set it up on an iOS device, an iPadOS device or Mac

True. But, this is the first line on page and this is the line why I posted the link :)

I stopped paying and went to the free Syncthing. My one issue is that the windows client silently fails and doesn't restart. Often. On multiple Windows 10 machines I own. The Apple and Linux clients have been rock solid, but the Windows one not, and since I use(d) this app as a way to get files easily to my partner who uses only a Windows box, this was the hard stop to my use case.

I find the fairly recent Smart Sync feature to be really nice, has definitely made many things simpler and more flexible.

Onedrive has it for free

My wife uses Gmail for her side business and it's nearly full (15GB for free is the current standard apparently). If she ends up paying for that service it might just be the thing that makes us drop Dropbox. Google drive is good enough for her needs (we don't really sync anyway, just upload and share).

I have been trying to move to iCloud as well, though unfortunately theres still no Android app for it till now

Dropbox uses very sophisticated binary diff nobody else provides to minimize inbound/outbound traffic; this has some CPU/battery cost though. Competitors usually provide very dumb upload/download that might be less CPU/battery intense but much heavier on the bytes transferred. You simply might not be their target group.

Yeah, I don't think so. Their target group must be people with 10mb of files or less.

Why would you need to binary diff when syncing dropbox to a new computer? Yet setting up dropbox for the first time on a new machine uses 100% of my CPU. The same S3 sync operation is barely noticible.

When updating files, first check for changes with something ultra cheap like an md5 then, if changed, do the "sophisticated" stuff.

They need to store your data somewhere, they need to be able to reuse/serve chunks from other users that share the same file to make its storage cost efficient etc.

onboarding cost might be annoying, but at least it's upfront. i'd take 100% at the start for more efficient sync later.

Yeah, if only it did that...

Which may be a feature that belongs in the bygone era of lower network speeds and bandwidth limits.

Do you like higher bills on your iPhone when accessing your shared data? Not sure why would efficiency belong to bygone era. I'd rather expect CPU to handle this diff process with some dedicated instructions more efficiently in the future.

I very much doubt that Dropbox's target group are users with bandwidth limitations. Yes, it's nice to have features that minimize waste on the network link, but I'd bet far more people would trade that away in exchange for laptop battery life and a smaller hit on their CPU.

If they're only targeting that niche, then they have a business model problem. Make it an option ("Minimize bandwidth or battery usage?")

I genuinely don't know, but are you sure that others don't provide this?

GDrive uses something internally but they don't expose it to public clients, so do they really provide it? (I might be outdated here, it's been a while I last checked)

Those who do not study ~~history~~ ~~Unix~~ rsync are doomed to repeat it poorly.

I used rsync to mirror one encrypted 14TB drive to another one. It took ~2 weeks. I wouldn't call rsync "good enough".

Something is very, very wrong then. rsync will use 100% of the bandwidth provided. It won't be any slower than anything else you might try over the same network. If you found that to be the case, it's almost certainly something else.

I guess if you have many overlapping files on both drives and you force rsync to actually look inside and compare them, its efficiency might suffer? It wasn't just a simple copy from one full drive to another empty one, rather two drives with overlapping files that had to be synced. I experimented with rsync to see if I could replace RAID with it, i.e. one primary drive, one backup drive synced on the background instead of mirroring directly (and getting the same low-level bugs spread to both drives or getting both drives to die at around the same time). Both drives were encrypted on the device level (dm-crypt AES128) with standard ext4 on top of mapped drive. I previously ran configs with RAID-1 as well as BTRFS RAID-5 (horribly buggy and dangerous) and wanted to see if rsync makes sense for this purpose (it doesn't). I couldn't use ZFS as that NAS didn't have ECC.

What was the bottleneck?

I am not bitl but my guesses, in order of probability would be: * using filesystem that is not natively supported on one or both drives, like fuse ntfs on Linux or ext3 on Mac. * copying over slower network like wifi * lots and lots of small files especially in a single directory * usb 2.0

Reminder that DropBox now uses a background web server instead of a native interface for their bare minimum client.

Famously, Steve Jobs once called Dropbox “a feature, not a product.”

Steve also said "There’s no better mobile computing tool than your finger"... Now they're rolling out mouse support on the iPad.

Mouse support on iPadOS is explicitly an accessibility feature. It's pretty awkward to use and not what you'd choose if you have a choice.

I’d even call it intentionally designed to be bad, because they don’t want you to use it. Which is the opposite of what the parent comment is implying. They have the ability to port over the full Magic Mouse/Trackpad drivers from macOS with intuitive scrolling and gestures, but they chose to leave them broken and awful to use.

I’m sure Jobs also commented on the merits of juicing, what does that have to do with Dropbox?

Damn!

Maybe "products" are actually bad when they lock you into an ecosystem like the company Steve Jobs headed does.

I typically hear the categories as feature, product, platform (aka ecosystem). Apple is a platform/ecosystem. Dropbox is a feature/product, but definitely not a platform.

In SV, "just a feature" has a derogatory connotation, sort of like "lifestyle business". It causes people who run feature companies to try to get away from this characterization – even if it means stretching their business into something that it cannot easily become. This is especially true for features that have no moat, and which would therefore be Sherlocked [1] by companies like Apple.

1: https://www.howtogeek.com/297651/what-does-it-mean-when-a-co...

Yeah, you've accurately explained how Silicon Valley culture can ruin companies that would be completely sustainable otherwise. Thanks!

For the record, I think both of these derogatory connotations are crap, and I run a "feature" startup myself. Fortunately, we don't need venture investment since we're running breakeven. Even with issued patents and paid licensees, it's nigh impossible to find VCs interested in a feature company.

You get that Dropbox has been desperately trying to turn into an ecosystem for its entire existence, right?

Yeah, VC is cancer.

It's true, Apple has deviously engineered it so their operating systems only run applications written for those operating systems. It's a good thing nobody else does that!

How can I sync to iCloud on my Android phone and Linux desktop?

Dropbox is still an insanely awesome product, and one of the few that I actually pay for and use on a daily basis -- it is a lifeline for my business!

I would have said the same thing in 2010 when I first started my business and needed file sharing/syncing in a small team. Everything just worked on Linux & Windows. Then they started tweaking everything, adding useless features, and it seems to be more of a hassle every year. But I'm still using it but if a cheaper, more lightweight service was offered, I'd probably switch.

Nextcloud? A NAS device? Google Drive? Practically all of these are cheaper and have the same or better usefulness. There's actually a ton of storage options out there.

Nextcloud and a NAS would both qualify as a hassle, I think. They have to be admin’d. After all NAS and FTP already existed when Dropbox launched.

Google drive is similar to Dropbox.

Although I'm going off Dropbox because of their attempts to become a "platform" I think people are forgetting a bit of what file syncing was like before Dropbox and how far behind the competition still are (at least in my view). Block-level syncing (so entire files aren't transferred with each small change) and rock-solid reliability is a pretty compelling combination for me. This is particularly so given that their prices are a drop in the ocean as a percentage of total expenses.

I keep trying other services (they'd need to be hosted by someone else - I don't want the added headaches of managing my own setup), but none have come close yet.

Dropbox has a tough road ahead. With Google Drive, Microsoft Word cloud suite and Box, its definitely getting tough to survive by just doing B2C. With their recent acquisitions they'll probably pivot to DocuSign like model. But they are definitely losing their niche.

B2C is the place to be - it is a niche where an excellent product is going to continue to earn excellent money. Continue to reiterate and continue to improve the product, dont overspend on infrastructure and dont rent super expensive office space in the most expensive cities in the world.

Enterprise is where SaaS companies go to die because they think that Microsofts of the world are just going to let them have the multi million dollar deals. That's a delusion.

I struggle to connect this to market facts. What big consumer SaaS tools exist? You could argue that Spotify and Netflix count. I disagree, but fine. You have networks like Tinder. You have a few tools companies like Carbonite, Dropbox, 1Password. These are niche.

In the enterprise... Slack, Twilio, Stripe, Okta, Qualtrics, Datadog, Zoom, I feel like I could name 10 more easily.

Enterprise is where SaaS companies get paid. Slack makes like half their revenue from 500 companies.

> You have a few tools companies like Carbonite, Dropbox, 1Password. These are niche.

SmugMug. Carbonite. Mailchimp. Backblaze. It is quite literally, pick a niche and there's a company making money servicing that niche. Is it a billion dollar company? Nope. Will it ever be if it sticks to doing whatever the product that it had? Who knows. But are they going to lose money on "enterprise" while cannibalizing its B2C business? Pretty much guaranteed.

Remember Borland? The one that created a market for $100 compilers it sold millions copies? It decided to replace those millions of customers paying $100 with a hundred customers paying a million? That was a total reversal of fortunes.

> Enterprise is where SaaS companies get paid. Slack makes like half their revenue from 500 companies.

And it still cannot make money.

Slack is also not making a profit and is still losing out to Microsoft in the enterprise. I can’t speak to the rest of them.

Not really. B2C is lucrative because it's tough to lose corporate contracts (at the Fortune 100) unless you do something completely egregious.

https://www.marketwatch.com/story/dropbox-cto-departs-as-sha...

It means those guys weren't innovative enough to keep making them money in some way that they wished they would.

https://news.ycombinator.com/item?id=21141513 links to the Dropbox Blog post (https://blog.dropbox.com/topics/company/thank-you-quentin--a...)

Hmm. What's interesting about it?

Dropbox recently had some backlash, mostly due to them updating their OSX software that installed a new file manager without the user's explicit permission.

Not sure if it's related, but they've had some issues with their tech stack lately

https://news.ycombinator.com/item?id=20477958

Something else they received backlash for is them limiting devices on the free tier to only 3.

https://news.ycombinator.com/item?id=19925652

https://www.theverge.com/2019/3/14/18265574/dropbox-3-device...

This hit me hard a few weeks ago, and still is.. I've had a few hardware issues and had to (re)install a few times. Limiting access to 3 devices, I'm not sure about upgrading. I don't really need more space, and in fact most of what I really use it for I could get away with a private github/gitlab repo.

Do you genuinely think the Dropbox CTO resigned because of some complaints about an app dialog.

I, for one, recently cancelled my long term Dropbox subscription based on only a few similar stunts they’ve pulled.

There’s anecdotal evidence that others have too.

Not the OP, but 'app dialogs' and their utility/uselessness are symptomatic of the underlying philosophy and business culture which made them a 'requirement' - so if the app dialog is undesirable, it carries implications about the internal environment in which it was developed, which may prompt someone to leave.

alternately: this was the person pushing the undesirable things, and other people pushed that person out as 'bad news', or, this person couldn't push more 'bad things' through effectively enough to his own liking and so left.

alternately: no relationship at all and this whole thread is just people dishing on their pet-peeves with the product.

Where there's smoke, there's fire

What happened?

They screwed up a perfect piece of software.

More like competition, including open source solutions, has reached a point where Dropbox is becoming obsolete.

I don’t understand why one would expect to be able to compete with iCloud, google drive, one drive. They have so much cash to burn.

Have you ever known Apple to “burn cash”? They have this crazy idea that products should be sold at a profit.

As in, whatever you can do, they can do better, since they are able to spend so much more.

It’s not they can do it “better”. They can do it “good enough” so that most people aren’t willing to use a smaller vendor and where the value add is not enough to have a sustainable business - see Dropbox, Spotify, Etc.

can you personally recommend any open source solutions that are reasonably plug and play?

syncthing[1] works nicely for me.

[1] https://syncthing.net/

For Windows users, SyncThing is normally a local browser app; SyncTrayZor wraps Syncthing into a more familiar SysTray app.

(Made finally ditching Dropbox a lot less daunting so I sing its praises on here when I can.)

https://github.com/canton7/SyncTrayzor

I went to Syncthing as well and it works, but it's still no match for the DropBox of a few years ago.

The CTO probably had a lions share in that. Not surprised how it went. :(

Stock price is down 26% in the past year. Either the CEO wants to show that serious steps are being taken to right the ship or the CTO is leaving for greener pastures. Since the article quoted the CTO as saying that he’s starting his venture career, I’m guessing it’s the former.

The most interesting use case for Dropbox is enabling cross-app workflows on iPad. Most apps support the Dropbox APIs now. Apple needs to get its shit together and make iCloud the back end. They can mandate that apps support their APIs, and then iCloud gets more revenue.