10 ms·

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

116 points by pospischil 15y ago

richardburton 15y ago
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"
- AndrewWarner 15y ago
  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.
  - richardburton 15y ago
    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.
    - AndrewWarner 15y ago
      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.
      - kn0thing 15y ago
        You're doing it right!
deleted 15y ago
[deleted]
manojlds 15y ago
"Startup Steve Jobs Wished To Own" - is that a compliment?
- jritch 15y ago
  I would believe so
jwr 15y ago
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?
- boyter 15y ago
  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.
- AndrewWarner 15y ago
  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.
  - zdw 15y ago
    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.
    - sskates 15y ago
      I think your expectations aren't properly calibrated, Dropbox's track record is stellar relative to the rest of the industry.
      - akl 15y ago
        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.
Alcedes 15y ago
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.
- beaumartinez 15y ago
  iCloud is OS X and iOS only. Dropbox is OS X, iOS, Windows, Linux, Android AND BlackBerry.
  - boyter 15y ago
    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.
    - mrkurt 15y ago
      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.
      - boyter 15y ago
        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.
        fpgeek 15y ago
        Dropbox is pre-installed on many Android phones, for example: http://geektech.in/archives/6318 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.
nodesocket 15y ago
Anybody have a link to the original video Drew posted here on HN? Was is the video on the DropBox homepage up until recently?
- yonran 15y ago
  I believe this was the original discussion: http://news.ycombinator.com/item?id=8863 http://news.ycombinator.com/item?id=8863 (2007-04-04) and the fixed video link is https://www.dropbox.com/screencast 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_MIT_Startup http://digg.com/news/story/Google_Drive_killer_coming_from_M... (2008-03-11)
Schwolop 15y ago
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.
- hboon 15y ago
  I'm sure it has some plus in terms of hiring. Not that I'm implying he's doing it for that.
miles_matthias 15y ago
tl;dl anyone?
pbreit 15y ago
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).

116 points by pospischil 15y ago

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"

AndrewWarner 15y ago
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.
- richardburton 15y ago
  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.
  - AndrewWarner 15y ago
    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.
    - kn0thing 15y ago
      You're doing it right!

deleted 15y ago

[deleted]

manojlds 15y ago

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

jritch 15y ago
I would believe so

jwr 15y ago

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?

boyter 15y ago
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.
AndrewWarner 15y ago
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.
- zdw 15y ago
  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.
  - sskates 15y ago
    I think your expectations aren't properly calibrated, Dropbox's track record is stellar relative to the rest of the industry.
    - akl 15y ago
      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.

Alcedes 15y ago

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.

beaumartinez 15y ago
iCloud is OS X and iOS only. Dropbox is OS X, iOS, Windows, Linux, Android AND BlackBerry.
- boyter 15y ago
  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.
  - mrkurt 15y ago
    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.
    - boyter 15y ago
      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.
      - fpgeek 15y ago
        Dropbox is pre-installed on many Android phones, for example: http://geektech.in/archives/6318 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.

nodesocket 15y ago

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

yonran 15y ago
I believe this was the original discussion: http://news.ycombinator.com/item?id=8863 http://news.ycombinator.com/item?id=8863 (2007-04-04) and the fixed video link is https://www.dropbox.com/screencast 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_MIT_Startup http://digg.com/news/story/Google_Drive_killer_coming_from_M... (2008-03-11)

Schwolop 15y ago

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.

hboon 15y ago
I'm sure it has some plus in terms of hiring. Not that I'm implying he's doing it for that.

miles_matthias 15y ago

tl;dl anyone?

pbreit 15y ago

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).