How Dropbox Became The Startup Steve Jobs Wished To Own – with Drew Houston | Hacker News Reader

How Dropbox Became The Startup Steve Jobs Wished To Own – with Drew Houston

mixergy.com

116 pointspospischil32 comments

I find it in poor taste to use Steve Jobs' name as a promotional tool. I see this done more and more and I don't think it's right.

They could have said "the startup that Apple wanted to buy", but that wouldn't have caught everyone's attention, right?

Wouldn't it also have been incorrect? From memory (cant find source sorry) it was Steve who approached DB and opened discussion. Also considering his personality traits it probably was his decision to attempt to buy them over the collective wisdom of people at Apple.

NB if anyone has some source to the contrary please share it here.

Steve Jobs is one of my heroes.

He famously called a lot things 'shit' and many people 'shitheads.'

And yet he saw something special in Dropbox. I wanted to find out how Drew did it.

Given their security record, Dropbox probably deserved (and still deserves, especially because of the unchangeable unique client ID issue) to be described in those terms.

I think your expectations aren't properly calibrated, Dropbox's track record is stellar relative to the rest of the industry.

I'm not sure they deserve to be called 'shitheads' either - I do like the service - but I'm still disappointed in how poorly they've handled their security issues, particularly the one back in June.

I think I'd have a different opinion if they'd bothered to reply to any of my multiple emails to them at the time.

I love Mixergy but sometimes I do not agree with some of the assumptions the questions are laced with. When Andrew Warner asks: "Where did you get the confidence ... to get into the storage space?" the assumption is that it required any confidence at all. It misdirects. Drew answered perfectly though: "I just wrote some code"

Could you help me understand when and how I do that? I don't want my questions to imply something that's not there.

I'll tell you why I asked him about confidence. It came after he told me that multiple experienced advisors told him that he was in the storage business and that a storage startup wouldn't work.

When I look at the email I get from my viewers, I see that many face similar situations and they worry about the viability of their startups. Rejections like that shatter their confidence. So I asked why it didn't have the same impact on Drew.

I thought his answer was a good explanation of how he dealt with the issue.

Hi Andrew. I hope I do not come across as a troll - I am a massive fan!

So let me rephrase. Confidence is the lifeblood of a startup founder. If they do not back themselves, who will? Sometimes over-confidence and even self-delusion can be very dangerous. I once tried to start a music label that gave away all the music for free and made money putting on live shows. I was deluding myself and drunk on my own confidence. The flip-side is what you describe: where people never recover from a knock to their confidence. This is much harder when the opportunity is actually really great. I think it is great to explore the confidence of entrepreneurs.

What my pedantic and pernickety side took issue with was the phrasing of the question and the context in which it was asked. Drew had just said he hacked together some code and you launched into a question about the confidence it must have required. I my mind was stuck on the notion that firing up a text-editor required confidence - a ridiculous notion I know but that is where my mind lept. I get the same awkward feeling when people begin any sentence with the word 'surely' because the presupposition is that surely they are right.

At that stage of the interview I would have been curious to know when, why and how the storage side-project made the transition from personal use to active user-base. You covered that really, really well later on. Which is why I love Mixergy.

I'm never hurt by feedback like that. I'm grateful for it.

Maybe I'm working the confidence question in too much. I'll watch out for that.

I want to get really good at doing useful interviews. I need feedback like yours.

You're doing it right!

I think Steve Jobs will be right again, Dropbox is a feature, a great feature to be sure, but still just a feature. iCloud works fine without it and eventually as Apple typically does, once more features are added, the need for Dropbox will lessen.

iCloud is OS X and iOS only. Dropbox is OS X, iOS, Windows, Linux, Android AND BlackBerry.

I'm still not sure how much of an advantage that is to the average user. To people on HN it's a huge plus, but to real world users...

Regardless DB should be able to carve out space where cross platform is important, but I can see their market size shrinking when Apple and Microsoft really start pushing their cloud storage solutions. Unless of course they get to a Facebook like level of critical mass.

If you extend that to TVs, cars, all phones, etc, real world users will care. It's less about cross platform and more about being ubiquitous.

Not sure about that. I think in that case it just needs to work, without any configuration, installing etc... It needs to be as pain free as possible. Unless DB can somehow be installed by default on those devices I can't see it making the grade.

Dropbox is pre-installed on many Android phones, for example: http://geektech.in/archives/6318 (which comes with extra free storage up to 5GB for HTC users).

Pre-installing on PCs is possible, though my quick Googling didn't turn up anyone doing it. Pre-installation on Apple devices is unlikely, of course.

Even you aren't cross platform personally (e.g. you don't have a Mac and a PC at work or an Android phone or ...) Dropbox lets you share files and folders with other Dropbox users. Unless you're confident that you'll never want to share with someone on a different platform (which only sounds realistic if you never want to share at all), that's important even if your personal environment is homogenous.

I'd guess that most Dropbox users share something (though I haven't seen statistics on that) so they are probably less threatened by vendor-specific solutions than you might think. I suspect Dropbox is more threatened by services like Amazon Cloud Drive (especially since Amazon is an infrastructure provider for them) than they are by anything Apple or Microsoft has planned.

I don't use dropbox for sharing at all, and suspect I am not alone. Generally use Google docs fir that. Dropbox just for replication to my devices.

When I was in graduate school, I saved all my documents to my dropbox folder, which was sync'd to my school laptop (OSX), my personal laptop (Windows), a lab computer where the stats software lived (Windows), my advisers computer (Windows), and my ipod touch (iOS).

I wasn't anywhere near the only one who had those kind of cross-platform needs. My program was a real mix of Windows and OSX users with a few linux users for flavor.

"To people on HN it's a huge plus, but to real world users..."

I think the opposite. If HN readers tastes' are similar to the average founder in the Valley, they are vastly more likely to use Macs and iPhones together than the average real world user, who is much more likely to use Windows/iOS or Windows/Android.

But the cross platform advantage means it get's recommended by the type of people that have cross platform needs to the type of people who don't. Would you rather hear, 'if you have an iPhone and a mac' or 'it just works.'

Most "real world" users don't use Macs.

Remember when the iPod only supported Mac? What happens when Apple decides to change the photostream shared folder on the PC into a generic folder to sync all files into the cloud? If Apple decides to roll that out, Dropbox days will be numbered. BTW, I'm a big fan of Dropbox, I just think the future is pretty clear in terms of how easily they can be marginalized.

I certainly don't know the whole story but the acquisition rumors seem very un-Apple-like. The hardest things about DropBox are acquiring users and paying for servers, two things Apple would not need to worry about (I know the technology is difficult, too, but am assuming Apple could figure it out).

I liked Andrew's point right at the end of the interview - Drew had no vital marketing imperative to come in and give an interview in that depth, he was just giving back to the community. Great to see.

I'm sure it has some plus in terms of hiring. Not that I'm implying he's doing it for that.

Anybody have a link to the original video Drew posted here on HN? Was is the video on the DropBox homepage up until recently?

I believe this was the original discussion: http://news.ycombinator.com/item?id=8863 (2007-04-04) and the fixed video link is https://www.dropbox.com/screencast

Edit: and here's the digg link but I can't figure out how to get anything useful out of it. http://digg.com/news/story/Google_Drive_killer_coming_from_M... (2008-03-11)

"Startup Steve Jobs Wished To Own" - is that a compliment?

I would believe so

tl;dl anyone?

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