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Interview with Drew Houston, CEO of Dropbox (bloomberg.com)
91 points by happy-go-lucky on June 8, 2017 | hide | past | favorite | 94 comments


Dropbox still has the best syncing app and integration, but is terrible with multiple accounts and any business use. Paper is also useless.

Box offers great controls for businesses, better API and built in workflow engine, but has crappy syncing app. Box Notes also useless.

OneDrive is just shit in every way possible and acts more like an unwanted virus in new Windows installations.

Google Drive has solid syncing with built-in search and google docs integration which is the best office suite other than MS office. Their Team Drives feature is finally doing things right for businesses, although it still has a broken permissions system and issues with desktop integration.

There's also Apple, Amazon, Egnyte, Quip, etc for other niches. Overall, we are nowhere near perfect with any service. All of these companies will continue to grow since there's no singularly great option yet.


Completely disagree re: Paper. It's one of the most-used tools at our company, and we love it.


Why? Google Docs or Office 365 can give you real-time collaborative editing that's faster, more stable and more reliable - along with all the other features like built-in file sync.

What does Paper do for you that's so much better?


Agree with all of these except Google Drive, which, if you are not completely part of the Google ecosystem is difficult to use.


That's similar to the rest in that a standalone file sync is just not as nice compared to having it integrated. We've found that G Suite is a lot easier to work with than Office 365 (unless you need offline office apps).


Whether or not you personally like Dropbox, they are an example of going up against the largest competitors on the planet and surviving.

And not just an example in general, but an example in detail -- decisions and efforts they made at every point, from engineering to corporate finance -- have been factors in that story.


A better characterization would be "the first mover fighting off large competitors". (Unless I'm misremembering) There was no direct equivalent of Dropbox at the time. I had tried everything from Skydrive to rsync. Dropbox solved a real problem with storage at that time.

(I don't use them anymore because they are too expensive but good for them that they are able to charge so much)


It's almost all spin. Enterprises are not adopting Dropbox (or Box) at any real scale because of privacy, security and control of data concerns. It's why you won't see any business that has data compliance requirements (such as banks) listed as a reference customers. The opportunity for large businesses to use Dropbox is very limited.


Where can you find these details on the decisions they made and the effects on their survival? Would be an interesting read.


> There are dozens of cloud-based tools aimed at business users. Can all these apps coexist?

> It's a mess. You have all these new tools like Slack, but they're totally disconnected from the old ones, so people are constantly toggling back and forth. This fragmented experience wastes a lot of time, and it makes it really hard to focus.

The proliferation and fragmentation of SaaS apps is a huge problem for businesses. When Drew Houston says it's a mess, you know there's a massive startup idea here.


It's a mess and also gets fairly expensive quickly when you put $10-20/month/user to several services.

One way forward is consolidated services like Bitrix. They may not be as good as Slack, Dropbox, Asana etc for some specific tasks, but may provide more integrated service with smaller price tag.

Another option would be for "best of breed" companies to team up to offer package deals.


> Another option would be for "best of breed" companies to team up to offer package deals.

That's a great idea, and I can't imagine why I haven't seen it in a meaningful way. I'd be very much on board to buy a "web office" bundle with Dropbox/Slack/Github/Trello or something like that if it meant upwards of a 15% discount.

It's obviously easier to make a personal budget for one re-occuring SaaS bill than 6 $5-10/mo SaaS bills.

Another obvious advantage is that a lot of these little folk have common enemies with MS/Google/Amazon, and this is a great way for them to achieve similar lock-in with almost zero investment.

Finally, Dropbox/Slack/GitHub/etc... all have awesome integrations that either already exist in each-others products or are super easy to implement.

I have a vague feeling there was a lesson about this in In Search of Stupidity [0], but I can't be sure.

[0] https://www.goodreads.com/book/show/1191767.In_Search_of_Stu...


> a massive startup idea

https://xkcd.com/927/ is evolving!


I think the idea was to make an interface that lets all these products interchangeable and integrated.


I recently started moving away from Dropbox after realizing I am not comfortable with how aggressive and anti-user this software is.

Last year the story broke about very questionable tactics of Dropbox Mac to gain root access.

This year I had a client whose machine was crippled because of a fun Dropbox default where, upon inserting any USB device Dropbox will automatically copy. The user inserted a camera with 4GB of hunting pics and it basically downed his machine. Now maybe he clicked on something to technically approve of this. But I surveyed the user base whom I had asked to install Dropbox and more than one had experienced a problem with this "feature". In one case the employee almost got in trouble for personal use of a machine, because she had connected her phone and didn't realize all her personal pictures were copied there. Less savvy users were involved, but I need to feel comfortable recommending a product like this to less savvy users.


I don't see how it's questionable. They did it to improve the user experience. If anything blame the OS for providing the ability to set it up properly.


I doubt most people are comfortable with deception around root access, in order to have a better user experience.

This is evidenced by the fact that Dropbox felt the need to apologize and alter their behavior. Largely through HN activism BTW https://techcrunch.com/2016/09/09/dropbox-responds-to-accusa...


On most macs I suspect there is one user -- so there isn't that much difference between user access and root access, either way you can read my web history and all my e-mails.


Most people have no idea what root access mean.

They explaining themselves is not evidence of what at all.


Did you read the part of the statement where they promised to make changes to the application disclosures?

Characterizing typical users as unable to understand rooting sidesteps the point that, when the concept is explained to them, most will not be comfortable with software companies doing this.


I definitely should have used the subjunctive case there, but I was addressing an HN audience who does get it. A charitable reader might have responded to the gist of the criticism.

Are you suggesting that because many of Dropbox's users don't know about the rooting thing, it's justified by their expansion?

I think the important thing is that, were most users to understand the rooting issue, they would be upset. Most users could easily understand it, if explained clearly. This is likely why Dropbox didn't disclose at all until caught -- and now, presumably, has a techie-sounding disclosure instead of "can we 0wn your machine?", if they are even still doing this on Macs.

This goes along with my original complaint about Dropbox: defaults that are ostensibly in Dropbox's interest, but not users'.


I am suggesting that the rooting was to improve the user experience and that only technical savy people really care about it.

The potential security issue isn't big enough to claim it's a problem compared to making it easy to use for most people.


That withstanding, what's your core threat model? The DB has network access and filesystem read and write access already.


yes I did and no it doesn't actually sidestep it as the claim was that most people would be upset about it which is simply wrong as they don't even know it's an issue. If you want to see evidence of that then look at their current numbers.


How did 4GB of stored pictures cripple his machine?


'Cripple' is probably an exaggeration, I wasn't there (just got the angry phone call) but I believe it was a combination of two factors. First his machine not having a huge amount of breathing room with HD space. Second, the "magic" automated, slow file transfer made his machine unavailable for manual use. But at some point he started to point the finger at Dropbox, started plugging and unplugging the device (have you tried turning it on and off again?). This was a quite smart person who was not computer savvy. I think he was trying to manually transfer a few photos to his PC. I get it... something he used to be able to do for himself stopped working, and until he figured out what was going on, effectively locked up his machine.

If you take this in the context of what others have said about Dropbox's takeover of CPU, hopefully my use of 'cripple' makes sense...

I have rarely seen cases where "magic behaviors" that users don't understand work really well.


They bounced back by raising prices, after users upload too much data to switch.

Dropbox for Business launched at $12.50 per user/mo for unlimited storage. It's now $20.00 per user/mo.

Bait and switch your way to profitability.


It's impossible to think that the features DfB launched with are equal or less than what they are now, so some of the price increase can be attributed to DfB providing more value to the customer.


I open dropbox manually on my Mac & quit it manually after a file has been synced. I don't see how can they survive any longer except for institutional customers who should be extra careful about surveillance.


People who do that or only use the web UI (to be blunt, people who frequent HN at all) are not Dropbox's target audience.


I only use the web UI.


Same


Be great if they could bounce back from using a third of my CPU on basic indexing.


Dropbox is unusable for me due to it pegging my CPU at 100%. And yes, I've opened mutiple supports tickets over the year.

The problem is I put my Outlook .pst in my Dropbox folder. When I have Outlook open, which is nearly the entire day, Outlook puts a lock on the .pst file.

Instead of Dropbox ignoring that file and coming back to it later - it's just gets stuck in some kind of infinitely loop trying to synch the locked file and can't. Resulting in 100% CPU usage.


I have the same problem. I basically use Dropbox as my work folder and put all my files in there. As a developer I have millions of small files. It takes 2-3 weeks to sync the dropbox from scratch (currently 285gb of dropbox files). And my CPU is regularly pegged at 100%. I basically have to switch Dropbox off when I'm not plugged into power on my Macbook Pro in order to conserve battery. I've contacted support several times, and their response was basically "don't".

I'm on one of their top plans (2TB). What's the point in having such large plans when the number of files you have causes the whole service to break down?

Been searching for a good alternative to Dropbox. Something that would be CPU efficient, safe, secure and reliable. I also use their packrat plan (saves a history of every file ever), which is nice too.

Any other HN readers have any alternatives? I really just want a plug and play solution, and not have to roll my own.

I don't trust Apple iCloud for one bit as they've been quite inept at running cloud services. I've tried Google drive with poor results too.


Yes, why not use git for the code files?

I have a single command on alias that goes and checks out all my git projects, and does a bit pull on any existing. Can switch between Computers in like 30 seconds. And it's all free git on bitbucket.

Git is much better way to deal with small files. Dropbox is ok for large files or nontechnical users.


I think all the consumer-grade backup and sync services are designed for a relatively small number of large files, such as high-res photos, songs and videos.

I have about 300K files (250GB total) in my 1TB SpiderOak account. The UI has always been atrociously slow, but backup speeds are okay when most files are static. Things get more interesting when I check out another branch in git and touch a few thousand files at a time. As for sync, well, I've all but given up on editing a file on my desktop, opening my laptop, and expecting the updated file to appear anytime soon. If I really need to sync a file immediately, I put in in my Dropbox (free account, almost empty).


I use an AWS Windows instance as a VDI. CodeCommit/SVN for code history and AWS snapshots for backup. This allows me to hop from physical computer to physical computer knowing that I always have everything with me. My physical computers are normally Macs but I mostly only use them for web browsing and as RDP client.

What I like most of this VDI setup is that, since it is a thin client setup, my computers last many years without becoming obsolete.


The initial sync really sucks. With smart sync things are much better, because you can easily pickup projects to download to your machine. With large amount of files and folders the regular selective sync has quite bad ux.

Unfortunately smart sync is only available for business subscriptions (probably because it makes it easy to put more stuff to Dropbox than you have disk space)


I eventually settled on Apple Time Machine. It backs up to a home NAS and a handful of drives at each office. The NAS can be configured to back up to S3 automatically.


Certainly a flaw in Dropbox, but one that can be easily worked around I think. Don't put the .pst directly in the Dropbox folder. Instead set up a scheduled task/cron job to copy it into Dropbox every few hours.

The Outlook .pst file plays notoriously bad with backup and synching in my experience. I set up CrashPlan for a family member once, and when I followed up a few weeks later it hadn't backed anything up in weeks because it was stuck on the .pst. In this case it was because the .pst was so huge and kept changing so frequently. By the time it had been uploaded for off-site backup, then it had changed and CrashPlan would start uploading it again. CrashPlan wasn't smart enough to prioritize other files in between, probably because it puts the most recently changed files in front of the queue or something.


I think CP prioritizes smaller more frequently accessed files. That said, you could use a different "back up set" for PSTs so that they not interfere with the backup of files in the other set.


And when you moved your PST file out of the DropBox folder it works fine?


Yes, when he stops saving the file he cares about it works.


Ok, I'm confused, just store the PST elsewhere. The location can be changed.

Sounds like he should make a copy to dropbox, if he wants a copy backed up.

Can't backup an open file after all.

This is just how computers work.


He is not complaining that the file can or cannot be backed up, and Dropbox is no backup service by the way.

He is complaining that their software hangs on open file instead of doing the sensible thing and not using 100% cpu until the lock goes away. That has nothing to do with "how computers work".


Maybe we could let them know so they can fix the issue (maybe you did already)?


"And yes, I've opened mutiple supports tickets over the year."


honest Q --- I'm not trolling I swear --- is Apple's iCloud any better in this regard? I know it's not cross platform... but if one is using Apple stuff exclusively, is the iCloud Documents in its current incarnation usable? Asking honestly


Yes - the current incarnation and ONLY the current incarnation - I.e. iOS10 and Sierra, is bulletproof and fast.


Had the opportunity to listen to Drew speak recently. He seems like a great guy and very humble. Definitely rooting for them.


That's a shame. Everything on drop-dropbox.com still applies.


A lot of my nonprofit clients are using Dropbox for its simplicity, but they sometimes have trouble locating things, and managing it when someone syncs their entire computer.


"That said, privacy is our focus, and we have whole teams that scrutinize any requests from governments to make sure they’re legitimate."

For a company with Condoleezza Rice on the board. A person who helped pioneer warentless surveillance. This doesn't really ring true:

http://www.drop-dropbox.com


Maybe judge their record rather than baselessly inferring that Rice has any say on any of this policy.

https://www.eff.org/who-has-your-back-government-data-reques...

(Full disclosure I'm ex Dropbox security)


I don't see where he infers anything. I do see where he notes that the company says one thing then their actions indicate something else.

Also, that link is from 2015.


Interestingly, dhouston don't post much on HN nowadays or even on twitter.


Dropbox has been, for me, a most disappointing outcome of the whole Internet'ization of computers.

I truly believe that Dropbox is a lousy solution to a problem created by ignorance on the part of the OS vendors. There is absolutely no good reason that the computers of today cannot share media seamlessly between themselves, without requiring the use or involvement of an external third party - the only reason its necessary to have Dropbox now, is because OS vendors fell asleep at the wheel and forgot that they're producing Operating Systems.

I think this will change, though - OS vendors are going to catch up to this market, and Dropbox will become less and less important as the OS starts to do its job again, and lead on these kinds of services.


I think you're being a little naive about what really drives features from an OS vendor here. That $vendor_A could enable seamless sync with $vendor_B is absolutely true, but the realities of competition and the market mean that technical feasibility isn't the driving factor.

I can't imagine Apple or MSFT ever offering something that would truly replace it - anything either does is likely to privilege their own OS over any other, and Dropbox has no reason to do that.

The other reason that services like Dropbox shine, at least for me, is that by providing a cloud-mediated sync solution, you don't have to coordinate a synchronous conversation between the devices in question. That's valuable, especially since it enables easy sync with > 2 devices (which also opens the door to selective sharing).

That always-there aspect is also how Dropbox became the de facto mobile file system for iOS (and Android, maybe? I'm guessing -- I'm an iOS user). It's also the default mechanism for sharing files too big or numerous for email (e.g., Aunt Sally's holiday pictures).

My tl;dr is that while Dropbox's initial value prop might not be earthshaking, it's done what it set out to do very, very well for me since I started using it 8 years ago, and I'm very glad to pay them for their service.


This is a head scratcher for me. First: doesn’t Microsoft offer OneDrive which is functionally equivalent to Dropbox? You seem to be saying MS doesn’t have incentives to do something they’ve already done.

Second: I realize everyone’s experience is different, but the three times I’ve had the misfortune to interact with Dropbox shared files (once in a corporate setting, twice with files shared by acquaintances outside work), it just didn’t work. So the meme that Dropbox is a reliable mechanism for sharing to others confuses me.


Sure, they have a work-alike, but the original comment seemed to suggest that this sort of thing should just be built in at an OS level without a "product" or add-in being required to support it. I think, but can't quite articulate why, that building a competitor to Dropbox (which both Apple and MSFT have done) isn't quite the same thing.

Obviously your experience is your own, but I have yet to have a Dropbox sharing event fail for reasons other than user error (typically by unsophisticated relatives or coworkers, so I'm not suggesting at all that this was the root of your problem).

We should probably both be cautious of overgeneralizing from our own experiences with Dropbox, but the general presence of "it's easy and it works" even among the nontechnical suggests that your experience is atypical for some reason. Did you ever figure out the cause?


Yes, I agree. There is what I would call a little more hubris than necessary in this side of the argument.

After all, it was once totally conceivable that a multi-million dollar company would be founded on the basis of, basically, a device driver.

We're still doing that sort of thing, its not a new phenomenon that some crack in the design/methods/ethics of a technology vendor is exploited by some un-controllable third-party. Gone are the days when Microsoft, by way of example, would have waged war and just built-in local- and remote- peer discovery, rsync++, etc. in response to this daring challenger to the hegemony.

I guess, I really do sort of miss that. Dropbox really sucks. I only use it because my friends do.


Just for clarity: do you mean it sucks politically, e.g. for privacy reasons? I'm familiar with those objections for sure, but if you're saying it sucks at some other level I'd love to hear why.


It sucks from the perspective of the usurpation of agency in pursuit of luxury, which in my mind has led to decadence.


Um.

In what way is Dropbox more guilty of this than any other tool/service provided by a third party?


>There is absolutely no good reason that the computers of today cannot share media seamlessly between themselves, without requiring the use or involvement of an external third party

If you're talking about some sort of decentralized peer-2-peer, the average non-sysadmin non-techie user isn't going to want to leave their laptop up 24/7 as a node to share files.

The lawyers with the legal MS Word docs, and accountants with their MS Excel spreadsheets want to shut down their computer, drive home, or get on an airplane, or go to a meeting that may not have wifi connection.

If we ask users to save it to some sort of store & forward storage so their files are accessible to others (especially with others who are outside their particular company's boundaries) ... well... you end up reinventing an entity like Dropbox.


>f you're talking about some sort of decentralized peer-2-peer, the average non-sysadmin non-techie user isn't going to want to leave their laptop up 24/7 as a node to share files.

The trouble is, precisely this argument can be made about every single layer, upon layer, upon layer, of cruft which requires a lot of things to be in place, just to make Dropbox work.

So, I'm sorry, but I don't think you've entirely thought this argument through. Dropbox should be a built-in.

Why isn't it?


Not OP but: I would love it to be built in. However, neither OneDrive nor iCloud currently work with the same ease of use and seamless function as Dropbox. And Dropbox (as with Google Drive) works across OS. So, my work computer is a Mac, and my Home Computer is a Windows PC. My Phone is an iPhone. I can access all of my files, anywhere, from any of these devices.


None of this would be un-feasible with a built-in service on any of those OS's.


Microsoft has been moving in that direction by bundling OneDrive with Windows 10 and making Office save files to OneDrive by default.

Unfortunately, OneDrive is little more than a half-baked clone of Dropbox. The first thing I do after setting up a Windows 10 machine is uninstalling OneDrive.


What about multi OS. You think a Windows pc, a MacBook pro, and an android phone will all sync files at the OS level? Really?


Yup. Technology to do this has existed since the birth of filesystems. This is a non-issue.


It doesn't matter if the technology exists (which it does) what matters is if the vendors will cooperate (which they won't).


If there was a standardized protocol/system for "cloud syncing" of files it's entirely likely they would all support it. Kind of like how they all support SMB/CIFS now.


It's not a protocol issue.

A universal protocol would only handle the "data in flight". The other issue is "data at rest" which is storage problem.

As analogy, SMTP is a universal protocol and yet email giants like GMail/Hotmail/Yahoo exist. They store emails. Average users don't want to point DNS MX records to their laptops running home mail servers 24/7.

- Dropbox-the-client-software simplifies "data in flight".

- Dropbox-the-cloud-storage simplifies "data at rest".

Since storage costs money (e.g. see Amazon Cloud Drive drops "unlimited" plan), it means there would be conflicting business interests from OS vendors at that infrastructure layer. This why a company that was _not_ Apple/Microsoft /Google/Redhat such as Dropbox was able to fill a gap.


There is nothing in the world wrong with me wanting to serve 4 terabytes of content off my own local machine, and know where it is going, and to whom, without the involvement of any third-party at the content layer. That is a feasible, realistic, and tangible goal in the current state of things. Dropbox has a lot of data. They're not a file-system vendor; they're a neo-google.


Yes, thats precisely my point. Dropbox is only relevant because the OS vendors are no longer servicing their end-users needs.


I'd like to see you substantiate that claim. I see no evidence that it's true.



You can't seriously be claiming:

1. Rsync has existed since the birth of filesystems.

2. Rsync will seamlessly sync between devices in the way that Dropbox does without the use of a third party. It clearly does nothing to overcome NAT.

It seems like referencing RSync does nothing to substantiate your claim, which still appears false.


They can & already do p2p files & audio/video/data using WebRTC(even Apple got onboard yesterday).

The problem dropbox tries to solve is allowing access to files when either party is not connected to the internet or to grant publicly share a set of files.


These are totally operating system functions. They should not be vendor'ed by what, I think personally, is a "Pepsi"-Co.


I think that if businesses can build their organiations on top of the Dropbox platform then they should do well. For individual consumers I'd love easy family/share services. You can probably already do this but nothing is really compelling.


I believe it should, and ultimately will be, a built-in. The Internet is going to route around Dropbox, eventually.


Six questions, two about politics.


Not sure if you mean to be negative here, but they are two very relevant questions to everyone in tech. I love his answer regarding immigration:

> Well, it’s really important—and it hits close to home for us. My co-founder Arash Ferdowsi’s parents immigrated here from Iran. If these policies were in effect back then, there would be no Dropbox.


Who's to say he would not have developed it in Iran or some other third country? Or is he saying the secret sauce is US + foreign talent and that that formula is atomic?

I would posit that that is false as there are many world class tech companies which did not begin in the US nor need the US to succeed.

To be clear, I'm glad they both successfully founded the company and that it contributes to the economy, but that's altogether a different topic.


I'm going to stretch the comparison a lot, but a great deal of the people working on the Manhattan Project were not born in the US.

What the US is doing right now puts it at a competitive disadvantage, IMO.


True enough. Both the US and USSR benefitted from raiding foreign talent as well as from taking in sympathizers to our/their ideologies. Fortunately we got some of the best, however, we did not have a right to them. It was circumstance, a good circumstance for us. Better would have been that it had been unnecessary to acquire the talent in order to win wars, prevent further suffering and vanquish miserable ideologies.

Interestingly, we didn't raid Japan for talent so much and maybe that contributed to their post war performance.


Einstein was effectively a refugee, so a "great deal" is an understatement as well.


I think he's just saying that a company is more likely to be founded after its cofounders have met.


Counterfactuals are funny. Dropbox wouldn't exist either if Hitler had not invaded Poland.


No Dropbox! The horror...


rdiff is free, open source and gives control to the user.

dropbox is large, binary-only, obfuscated code, built on FOSS (uses same library as rdiff), makes some people very wealthy and gives third party control over user's files.

i have never used dropbox. no need.




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