
Employee #1: Dropbox - craigcannon
http://themacro.com/articles/2016/09/employee-1-dropbox/
======
keithwhor
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
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
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
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
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.

~~~
potatosareok
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
I think the key difference between founders vs. early employees is in risk
tolerance. An early employee should be able to go to work reasonably confident
that he will get paid for his time and his efforts will not be completely
futile. The job description for "founder", however, involves _finding a reason
for the company to exist_ , and that inherently involves the risk that you
could put in a lot of work and it'll still count for nothing.

Aston (presumably) made out with a lot more than the $300/400K a year that a
Google/Facebook engineer tops out at. He also took on more risk, but the risk
was largely technical risk: the possibility that him and his teammates
couldn't deliver what 65,000 people said they wanted. That risk is largely
under their control, while as a founder, the primary risk is that nobody wants
your product or it can't be built economically.

I do think that the large amount of money in the funding ecosystem lately has
distorted this bargain somewhat. In boom times, you get cases where the
founders get funded on hope & pedigree and draw a salary immediately (meaning
that their financial risk is more akin to an early employee's), and then they
go and hire a bunch of naive employees at below-market rates before getting
any validation that people want their product (meaning that the employee now
takes on market risk that was previously reserved for the founder). This
doesn't do either the company or the employee any good; these companies are
significantly more likely to fail than ones who stay founder-only while they
prove out the market, and they ruin more peoples' lives when they do. If you
look at employee #1's who have actually made out well - eg. those at Google,
DropBox, Thumbtack, AirBnB, SnapChat, etc. - all of those companies had
validated demand, had raised funding, and in many cases were already in use by
thousands of people when they hired their first employee.

------
typetypetype
> We were all using the product so when there was funny stuff we tended to
> catch it.

I love this. There have been so many times I've run into a bug that makes me
wonder if anyone on the engineering team actually used the product.

~~~
gregmac
Also known as 'dogfooding' or 'eating your own dog food' [0], and yes, not
enough companies/software teams do this. Developers that build software aimed
at or naturally used by other software developers kind of have an unfair
advantage here.

[https://en.wikipedia.org/wiki/Eating_your_own_dog_food](https://en.wikipedia.org/wiki/Eating_your_own_dog_food)

~~~
walshemj
Back when I worked for a pre internet messaging company our terminals speed
was slowed down to the same (1200 or 2400 baud) as a dial up user would see.

~~~
dasmoth
There was a story last year about Facebook having "2G Tuesdays" to give
employees an idea of what life on a slow network is like. I wonder whether it
caught on?

~~~
BinaryIdiot
Such a genius idea. I see far too many web applications not caring about
latency. Forcing a developer to experience the same pain should help them.
Unless that simply becomes the day everyone typically takes off, blames
productivity on slow network connectivity, etc.

~~~
nostrademons
Google had a latency proxy on the corp network that you could use to simulate
dialup, 2G, DSL, etc (along with unreliable connections). It was a great tool,
and you could learn a lot by doing all your normal searches through the
latency proxy. Alas, not many developers knew about it, and even fewer were
willing to take the convenience hit to use it as part of their normal
experience.

~~~
thedufer
OS X used to have a "Network Link Conditioner" that shipped with XCode, I
believe. It did a lot of the things you're suggesting, but right at the
network interface level. Unfortunately, it broke with the advent of Mavericks.
No idea whether it works now, or even still exists.

On the last web-app project I worked on, we had a middleware that activated
automatically in dev mode and just inserted a delay in every request to bring
a local delay up to our users' median delay. It was intentionally a bit of a
pain to turn off, so almost everyone ran in that mode.

~~~
ptomato
Still exists.
[https://developer.apple.com/download/more/?q=Hardware%20IO%2...](https://developer.apple.com/download/more/?q=Hardware%20IO%20Tools)
is the link you're looking for.

------
huac
"MIT is cheating. Going to MIT you end up getting to meet lots of people who
are smart and fun to hang out with and you’ll get along with naturally. It’s
much harder after school."

------
doktrin
Aston is a class act. He volunteered to act as a mentor to students in a
coding bootcamp I attended several years ago, and it was my privilege to meet
him. He's the sort of person who is unequivocally a net positive in this
world, and I wish him all manner of continued success.

------
dude_abides
> But I ended up picking Mercurial for the distributed version control system,
> which we were definitely wrong on that one–should have picked Git.

I'm curious to know: is this sentiment widely shared? Is git really that much
better than hg?

~~~
diamondtrim
Never used mercurial. I suspect it's just as good, but the problem the author
probably sees is, like me, most everyone is familiar with git and new hires
need to be trained in something unfamiliar with less community around it.

~~~
bch
I wonder how large that friction is. I look at git, mercurial, etc as
distributed version control first and foremost, and that they're more alike
than different.

It _could_ be that I witnessed the popular adoption of all this via Linux
going from tarballs/patches/mailing lists -> bitkeeper -> git, and have used
and witnessed-the-evolution-of rcs, cvs, subversion, various DSCMs, and so my
concepts of source control are stretched more broadly than people that are
experiencing the dissonance between (e.g.) mercurial and git.

Edit: clarifying words

~~~
marcosdumay
If you are used to an "always branch" workflow, mercurial can impose a lot of
friction.

~~~
Bjartr
Do you have anything you can point to for that friction? I'm always looking to
do better than I already am and would be interested in understanding the
issues here.

------
nasalgoat
"In general, my thing is, again, in keeping with Dropbox’s conservative
culture, if you can use languages and tools and databases and frameworks that
are 10 years old or older, you’re probably doing pretty good."

That's a level of understanding I have trouble getting from very experienced
developers and system admins, let alone a fresh college grad. I wish more
people would realize that.

------
_RPM
Does Drew come from a privileged family?

~~~
samfisher83
His dad went to harvard so I am guessing he grew up pretty well off.

~~~
_RPM
Yep. That explains how he was able to focus full time on Dropbox then. He must
have always had a trampoline to bounce him back up should he fail. I know it
was funded from the beginning most likely, but there had to have been a time
before it was funded.

~~~
psyc
I know it's fun to be envious of rich people, but I grew up in poverty, and so
far I've earned myself 5 years to focus full time on my stuff. I know it's a
little harder, maybe, but all I had to do was go to work first. Most people go
to work anyway.

~~~
_RPM
Maybe I did come off as envious, but I'm not angry, or sad, or feeling like I
don't have opportunities to be a successful startup founder myself. It's just
that you do often see a pattern among founders. It's so common that I've
started noticing it.

It's certainly not true that you have to come from a privileged family to be a
successful entrepreneur. Look at examples like Larry Ellison.

~~~
bdr
It seems like your question was set up to confirm your conclusion. If you had
instead asked how Drew was able to support himself, you'd probably get a more
accurate answer.

------
webo
Ironically, Drew's YC application is stored in Google Docs:
[https://dl.dropboxusercontent.com/u/27532820/app.html](https://dl.dropboxusercontent.com/u/27532820/app.html)

------
pw
Anyone noticing from these interviews that a lot of first employees are kinda
just randos that aren't very impressive in their own right and don't stay at
the company very long?

~~~
elgenie
Aston's tenure at Dropbox (four and half years) is "very long" in Silicon
Valley terms in general and in early stage startup terms in particular.

As for being "randos that aren't very impressive in their own right", you're
zeroed in on a set of people who joined a startup before there was much
traction, let alone profit, with almost the same risk as the founders but with
less upside. That group is going to skew young and/or unsuccessful before they
join and, since the interviews are conducted with #1 employees at successful
companies, will skew towards having FU money for their post-exit careers.

~~~
pw
I realize first employees will tend to skew young and/or unsuccessful and, as
a result of being first employees, these people have FU money, but my point is
that their success seems to be kinda random. There's no sense of inevitability
about their success like you see with really great founders. And it seems like
they never go on to do anything amazing in their post-exit careers.

~~~
elgenie
How amazing is the post-exit career of the average great founder? What if the
success of the "really great founders" similarly has quite a bit of randomness
involved? The halo effect and associated myth-making doesn't get applied
nearly as much to employee #1.

~~~
pw
I think you might have a point about the "post-exit career of the average
great founder" in that it's usually not that impressive.

Larry and Sergey certainly would qualify as "great founders", given their
level of success, and, while they continue to run Google competently, they
really haven't done anything else (Google still really only has one line of
business, after all).

Whereas on the other hand, we have someone like Bezos who, with AWS, has
created not one, but two ten billion dollar plus businesses and whose ambition
seems to be boundless. Or, of course, Elon.

------
vazamb
A minor detail, but I am surprised about the whole "it was hard to figure out
when someone moved a file" thing. I always assumed the actual file on disk was
abstracted away into a database record, that specified the folder etc. Were
they actually using S3 Bucket/Folders for file structure on Dropbox itself?

~~~
hoov
It was more of a lack of abstraction than anything. The server reflected more
or less what the OS presented -- an add and a delete rather than a move.
Putting the pieces together later to present better information to the user
was difficult. Not sure what they do today, but I remember many talks about
ways to put that abstraction in place as close to the OS as possible.
Reconstructing multiple, quick, renames/moves after the fact proved to be
somewhat difficult from the frontend, which Aston worked on.

------
psawaya
What a great interview. There's so much under-appreciated advice here,
particularly around founder/idea fit.

I've been lucky enough to know Aston over the past two years, and have always
been super impressed by his insight.

------
olantonan
Awesome story

------
pensive_returns
An interesting titbit Aston leaves out about his early days is that he was
actually cofounder of AutoAdmit.com[0], a law school admissions forum, semi-
notorious for its defamation lawsuits and being an incubator for troll,
Michael O. Church[1] (banned on Quora, Wikipedia, and Hacker News for being a
thorn in Paul Graham and Dan G, sides) that formed after the great Princeton
Review Discussion Board exodus and has persisted with an active user base for
almost 13 years now. I wonder if he's ashamed of that history since he fails
to mention it (despite it being on his early resume!).

[0] [http://www.autoadmit.com/](http://www.autoadmit.com/) [1]
[https://michaelochurch.wordpress.com/](https://michaelochurch.wordpress.com/)

~~~
idlewords
What is the connection between AutoAdmit and Church? I don't understand how
he's relevant here.

~~~
hopethathelps
Church used to post obsessively on AutoAdmit under the name "pensive" and have
lengthy conversations with sockpuppet accounts.

Draw your own conclusions.

