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I was lucky enough to hear this story almost verbatim from Aston and it's so exhilarating to listen to how much fun everybody seemed to be having. He tells it w

I was lucky enough to hear this story almost verbatim from Aston and it's so exhilarating to listen to how much fun everybody seemed to be having. He tells it with a lot of enthusiasm that you can feel just from the depth of his responses. I think the one thing that stuck with me, personally, is the issues Dropbox had in the early days (TC 50 tech issues) and that it took six months to get Aston on board. From what I understand, pre-YC was not easy for Drew either. As a stubbornly impatient person, this has to be hands-down the hardest part of building a startup. You're running an endless marathon as if your life depended on it, and you have to stop at the sidelines and calmly ask people if they'll run with you. And then be okay if they don't - because the course will change, and as it does it will become more attractive to different sets of people. You might see the finish line, but you have to understand that not everybody will see it the same way you do. The thing that I'd add here is that Aston kind of downplays how important having a business model is as an employee / founder (at least per Drew joking around about pricing). I don't think he did this intentionally, but generally we're over saturated with these ideas that you just need a product people love. These stories inspire technical founders, but having a defensible business is something you should think about sooner rather than later. Not everybody can be a Dropbox, so learn as much as possible about every aspect of what your company can and will be, learn how to communicate that, and stack the deck in your favor. It's an ongoing process and I certainly am not one to claim mastery (far from it), but as somebody who's in the weeds it's the perspective I have.

ryandrake 10y ago
What I don't get is why try to recruit the same person over and over for six months? I wonder what the outcome would have been had they just hired someone else equally as talented right away instead of going without an employee for all that time. You can't re-play these things so we'll never know, but it just seems odd to me.
- nostrademons 10y ago
  They didn't have funding (other than YC, which at the time was $6k/founder, not nearly enough to support an employee) until right before they hired Aston. Drew had approached me about being employee #2 for DropBox, and I had lunch with him, Arash, and Aston in Feb 2008. They'd only closed the Sequoia seed round about a month before. IIUC, Aston had been officially hired the day before. I (stupidly in hindsight, but for good reasons at the time) ended up declining. I actually reconsidered about two months later and asked if the position was still open, but they had long since filled it - I think they got some very good MIT grads literally later the afternoon after I had declined. So they were hiring very aggressively, but they started recruiting before they were in a position to actually hire, to warm up potential employees.
  - mkagenius 10y ago
    Interesting example. Genuine question, had it been the opposite, if you circle back in time, would you really take that job? (Trick question: Are you less happy than you think you would have been in other case?)
    - nostrademons 10y ago
      Complicated question. It certainly would've been better financially, though honestly, the difference is "set for life" vs. "set for a long time", so I'm not certain it would make a material difference in my life now. Besides, I think it's fairly likely that even if I were set for life, I'd be doing something fairly similar to what I'm doing now. I think that in terms of lifestyle & personal goals during the 4-5 years I would've been at DropBox, I actually did better (I ended up folding up the startup I was working on and working for Google, and I had a relatively stress-free, enjoyable, lucrative, and personally fulfilling time at Google where I grew a lot as a person). I do think that my reasons for not taking the job have been invalidated by future experience. My top reason was "I'm not going to leave my cofounder", and then he ended up leaving me 2 months later. My second reason was "Well, you've got a startup, I've got a startup, it is unclear which of us is actually going to succeed," and of course my startup was dead in 6 months while DropBox is now a $10B company. (Interestingly, I had a gut feeling at the time that I was turning down something important - I could tell Drew/Arash/Aston were crazy smart, and I really liked their product concept video.) But Drew actually told me "Honestly, if I were in your position - and I have been in your position - I wouldn't take the job" and he was right. The bargain we make as entrepreneurs is getting to call the shots, and the consequence of this is that sometimes we make the wrong call, and in a way it's not wrong after all because the whole point was making the call in the first place. There's also the issue of whether DropBox would be a billion-dollar company at all if they'd hired me. I think my skillset actually duplicated Aston's to a fairly large extent, and we would've argued over technology choices (I would've pushed for Django, JQuery, and git over Pylons, Prototype.js, and Hg - the fact that these won in the wider webdev world is immaterial, just arguing over them would've cost precious time that a startup can't afford). Instead they hired some very talented MIT grads instead, and my understanding is that these engineers were responsible for things like reverse-engineering the Finder and writing the syncing algorithm that were what really contributed to DropBox's success.
- zenlikethat 10y ago
  Chemistry and low risk. They knew what they were getting which is worth its weight in gold considering how hard it is to generally judge how well software engineers will perform once on the job.
- qq66 10y ago
  Because 1) for brand new startups, which all kind of seem like dumb ideas or impossible ideas at the beginning, only a very small fraction of very talented people are willing to join, and 2) at such a small team size, there's so much more than talent that matters. You'll end up working with that person so closely that they can't just be smart or talented -- you have to trust them to be a partner in helping steer your company towards what it's eventually going to be, in product, technology, culture, etc.

ryandrake 10y ago

What I don't get is why try to recruit the same person over and over for six months? I wonder what the outcome would have been had they just hired someone else equally as talented right away instead of going without an employee for all that time. You can't re-play these things so we'll never know, but it just seems odd to me.

nostrademons 10y ago
They didn't have funding (other than YC, which at the time was $6k/founder, not nearly enough to support an employee) until right before they hired Aston. Drew had approached me about being employee #2 for DropBox, and I had lunch with him, Arash, and Aston in Feb 2008. They'd only closed the Sequoia seed round about a month before. IIUC, Aston had been officially hired the day before. I (stupidly in hindsight, but for good reasons at the time) ended up declining. I actually reconsidered about two months later and asked if the position was still open, but they had long since filled it - I think they got some very good MIT grads literally later the afternoon after I had declined. So they were hiring very aggressively, but they started recruiting before they were in a position to actually hire, to warm up potential employees.
- mkagenius 10y ago
  Interesting example. Genuine question, had it been the opposite, if you circle back in time, would you really take that job? (Trick question: Are you less happy than you think you would have been in other case?)
  - nostrademons 10y ago
    Complicated question. It certainly would've been better financially, though honestly, the difference is "set for life" vs. "set for a long time", so I'm not certain it would make a material difference in my life now. Besides, I think it's fairly likely that even if I were set for life, I'd be doing something fairly similar to what I'm doing now. I think that in terms of lifestyle & personal goals during the 4-5 years I would've been at DropBox, I actually did better (I ended up folding up the startup I was working on and working for Google, and I had a relatively stress-free, enjoyable, lucrative, and personally fulfilling time at Google where I grew a lot as a person). I do think that my reasons for not taking the job have been invalidated by future experience. My top reason was "I'm not going to leave my cofounder", and then he ended up leaving me 2 months later. My second reason was "Well, you've got a startup, I've got a startup, it is unclear which of us is actually going to succeed," and of course my startup was dead in 6 months while DropBox is now a $10B company. (Interestingly, I had a gut feeling at the time that I was turning down something important - I could tell Drew/Arash/Aston were crazy smart, and I really liked their product concept video.) But Drew actually told me "Honestly, if I were in your position - and I have been in your position - I wouldn't take the job" and he was right. The bargain we make as entrepreneurs is getting to call the shots, and the consequence of this is that sometimes we make the wrong call, and in a way it's not wrong after all because the whole point was making the call in the first place. There's also the issue of whether DropBox would be a billion-dollar company at all if they'd hired me. I think my skillset actually duplicated Aston's to a fairly large extent, and we would've argued over technology choices (I would've pushed for Django, JQuery, and git over Pylons, Prototype.js, and Hg - the fact that these won in the wider webdev world is immaterial, just arguing over them would've cost precious time that a startup can't afford). Instead they hired some very talented MIT grads instead, and my understanding is that these engineers were responsible for things like reverse-engineering the Finder and writing the syncing algorithm that were what really contributed to DropBox's success.
zenlikethat 10y ago
Chemistry and low risk. They knew what they were getting which is worth its weight in gold considering how hard it is to generally judge how well software engineers will perform once on the job.
qq66 10y ago
Because 1) for brand new startups, which all kind of seem like dumb ideas or impossible ideas at the beginning, only a very small fraction of very talented people are willing to join, and 2) at such a small team size, there's so much more than talent that matters. You'll end up working with that person so closely that they can't just be smart or talented -- you have to trust them to be a partner in helping steer your company towards what it's eventually going to be, in product, technology, culture, etc.