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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

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.
- JonFish85 10y ago
  "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" Let's not forget that DropBox hasn't exited yet, and in fact may be in a very tricky position. As much as it's fun to look at "I'd have had 0.75% of $10bn, that's $75m!", it's rather unlikely that you'd see that money. Maybe they can pull it off, but it's also possible that they are in a bit of a tight spot where they're over-valued, which can absolutely ruinous to employee options. They have to prove to the market that they're much more valuable than Box, which has a head start on them in that regard. I'm not sure I'd view it as that clear-cut. If you walked away from your previous company with a life-changing amount of money, there's a very solid chance you were better off there than at DropBox, purely from a financial perspective. I'm not trying to be a jackass, I'm just trying to say that they haven't exited yet, and you can't really compare!
  - nostrademons 10y ago
    I assume there have been secondary stock sales. It's pretty common these days for relatively liquid secondary markets to spring up around tech unicorns. The fact that they aren't "public" doesn't mean that you can't sell; it just means you can't sell to ordinary people. Markets treat regulation as damage and route around it.
- potatosareok 10y ago
  Hey Nostrademons, I appreciate your thoughtful responses so I was wondering what your thoughts are on importance and corresponding compensation of the 1st employee at a company. If the first employee is important enough that in your mind, it's possible that with depending on the first employee they may or may not be a billion dollar company, do you think the first employee compensation is commensurate with that? Aston also mentions specifically the commitment he has as a first employee, and how he feels "you're basically a founder" in terms of responsibility. In my opinion, he made off about as well as any first employee could reasonably expect (even unreasonably I'd argue). I don't have the perspective of either a startup founder or the first employee anywhere so I'm not trying to slight the Dropbox founders in any way. I guess my question boils down to two parts 1. What do you think a reasonable level of compensation is for a first employee 2. Given the success rates of startups (low), why would someone want to be the first employee somewhere versus either their own startup, or a later stage company that could pay them a much higher salary then the typical startup compensation. My unstated assumption here, which you might disagree with, is that someone who could have the impact of Aston, could become a staff engineer at somewhere like facebook/google/microsoft/etc and pull total compensation of 300/400k with a significantly higher chance.

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.

JonFish85 10y ago
"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" Let's not forget that DropBox hasn't exited yet, and in fact may be in a very tricky position. As much as it's fun to look at "I'd have had 0.75% of $10bn, that's $75m!", it's rather unlikely that you'd see that money. Maybe they can pull it off, but it's also possible that they are in a bit of a tight spot where they're over-valued, which can absolutely ruinous to employee options. They have to prove to the market that they're much more valuable than Box, which has a head start on them in that regard. I'm not sure I'd view it as that clear-cut. If you walked away from your previous company with a life-changing amount of money, there's a very solid chance you were better off there than at DropBox, purely from a financial perspective. I'm not trying to be a jackass, I'm just trying to say that they haven't exited yet, and you can't really compare!
- nostrademons 10y ago
  I assume there have been secondary stock sales. It's pretty common these days for relatively liquid secondary markets to spring up around tech unicorns. The fact that they aren't "public" doesn't mean that you can't sell; it just means you can't sell to ordinary people. Markets treat regulation as damage and route around it.
potatosareok 10y ago
Hey Nostrademons, I appreciate your thoughtful responses so I was wondering what your thoughts are on importance and corresponding compensation of the 1st employee at a company. If the first employee is important enough that in your mind, it's possible that with depending on the first employee they may or may not be a billion dollar company, do you think the first employee compensation is commensurate with that? Aston also mentions specifically the commitment he has as a first employee, and how he feels "you're basically a founder" in terms of responsibility. In my opinion, he made off about as well as any first employee could reasonably expect (even unreasonably I'd argue). I don't have the perspective of either a startup founder or the first employee anywhere so I'm not trying to slight the Dropbox founders in any way. I guess my question boils down to two parts 1. What do you think a reasonable level of compensation is for a first employee 2. Given the success rates of startups (low), why would someone want to be the first employee somewhere versus either their own startup, or a later stage company that could pay them a much higher salary then the typical startup compensation. My unstated assumption here, which you might disagree with, is that someone who could have the impact of Aston, could become a staff engineer at somewhere like facebook/google/microsoft/etc and pull total compensation of 300/400k with a significantly higher chance.