I was among the naysayers. I first met Drew at pg's house just before Dropbox did YC. I listened as he explained Dropbox, and I immediately thought of a dozen reasons why it would be very difficult and probably fail (I'd recently worked on something very similar for a month or so just to figure out whether it was a direction I wanted to go with my own company, so had some familiarity with the scale of the problem...I also knew the allure of the simple parts of the problem).
I don't recall a whole lot about the conversation; I thought Drew was smart, and he seemed to have a pretty good understanding of all the problems he was going to have to solve. But, I still had my doubts, and walked away assuming Dropbox would not be one of the success stories out of that upcoming YC batch. We see who from that conversation is now a billionaire (or will be in the coming years)...so, it seems I was wrong. Or, at least, overly pessimistic about Drew's understanding of the problems and his ability to resolve them.
And I'm an example of how you can be right and still wrong because you let "other plans" get in the way. I'm on that thread with my two cents: "I'm impressed."
However, Drew took me out to lunch about 10 months later. They'd just signed their Series A with Sequoia (although it wasn't public knowledge), and were looking to hire their first couple employees. Aston had just been hired the day before as employee #1; Drew was wondering if they could interest me in being employee #2.
At the time, I had my own startup that I was trying to get off the ground with a friend from college. I could tell Drew was wicked smart, and he was way more prepared and ready to bring a product to market than we were. But my immediate response was "I can't leave my cofounder, and I want to see where my startup ends up going." He was very understanding, and said "Yeah, if I were in your position - when I was in your position [DropBox is Drew's second company] - I wouldn't give it up either." I couldn't help thinking, as I walked away, that maybe I'd just passed up the best opportunity I'd get in my life. They filled their positions with a couple MIT grads later that day.
A couple years later, after I'd moved out to the Bay Area and was working for Google, I saw Aston at Maker Faire, and mentioned that maybe I'd made a mistake in passing on DropBox. He said, "Naw, you made the decision that was right for you." And in hindsight, I think that's correct. I had 3 dreams coming out of college: one was founding a startup, another was inventing a programming language, and a third was learning how Google Search works. This way, I got to try my hand at all 3 of them. And I'm not sure DropBox would've succeeded the way they have if they'd hired me: they got some kickass early programmers instead, and I had some growing up to do before I was really ready to start something big.
I like your story, and your humility. I think that Aston is right. At the time, it was the best decision for you, based on what you knew, and wanted to do.
Nothing prevents you from inventing something spectacular at Google, now :)
Quite an interesting story. I guess I am a few years behind you, as in I just graduated a year back and get offers from startups which i accept/turn down. I often wonder how these startups would end up and where I would be relative to them. But I guess what makes the most sense here is the part that says "you made the decision that was right for you.". That kind of seems like the right line of thought.
FWIW, during that time period (07/08), I talked with about 10 startups about joining as a founder or early employee. DropBox is the only one still in business today. So I think that the Paul Buchheit post that Joe linked is pretty accurate: "How to be right 90% of the time: predict it'll fail." It's just that you only need one success.
I've had other reasons for staying at Google as long as I have, though, and I wouldn't necessarily consider it a failure.
From what I've seen, 'naysayer' is a term people most commonly use to ignore and suppress critical thinking. It's very convenient, because it sidesteps the question of why someone says 'no', and blames it on their personality instead, making all kinds of 'no' (substantiated or not) equivalent.
Besides, people who can't handle criticism are usually the same people who can't properly deal with new ideas either. Have you never seen large corporations going under because of abandoning their main products and chasing something new and shiny? That's a case where some intelligent no's would save the day.
it may not be of much comfort to you, but sometimes naysayers are important. Even if they are wrong about the overall trajectory, they may in the process of naysaying point out specific weaknesses that the visionaries might have missed, and, thus, ultimately allow for the success of the product.
Careful! A lot of would be Drew Houston's end up discouraged by naysayers. As a founder, it took me a while to know who to listen to. One of the toughest things about doing a startup is people telling you you're wrong all the time. One of the things YC (and pg in particular) gets right is that they're very encouraging of potential for success.
Perhaps this was your problem. Who is not important, what they are saying is.
You're being told you're wrong? Why? Do they have a point or does their argument break down to simply 'because' or 'because no one has done it that way before'?
If they have a point, at the very least, they probably just pointed out a problem you need to over come in the future and you can thank them for expanding your understanding of the situation.
> Do they have a point or does their argument break down to simply 'because' or 'because no one has done it that way before'?
You'll find that the vast majority of arguments that people give you have a point. Look no further than the arguments provided against Dropbox here. The real difficulty is knowing which points are more important than others.
For example, whether developing a desktop program has the potential to be the next big startup in part depends on whether or not you believe the desktop market will still be around in the next some odd years. There is no 'right' answer to that question unless you happen to be able to see into the future.
> A lot of would be Drew Houston's end up discouraged by naysayers.
I think this is one of the more troubling aspects of entrepreneurship. Most of today's really big, wildly successful tech companies sounded like really dumb ideas when they were first launched. I wonder how many Googles/Facebooks were never founded because their founders were discouraged by naysayers??
good point, not everyone has skin as tough as me (I'm in the sciences, where the most searing crucible is not your colleague's criticism, but the cold, silent, emotionless failure of an experiment).
I do get a kick out of all the complaints and snarky comments. Sometimes you just have to do one thing very right, and everything else takes care of itself.
I don't recall a whole lot about the conversation; I thought Drew was smart, and he seemed to have a pretty good understanding of all the problems he was going to have to solve. But, I still had my doubts, and walked away assuming Dropbox would not be one of the success stories out of that upcoming YC batch. We see who from that conversation is now a billionaire (or will be in the coming years)...so, it seems I was wrong. Or, at least, overly pessimistic about Drew's understanding of the problems and his ability to resolve them.
I refer to this pretty frequently to try to remind myself not to be the naysayer in the room: http://paulbuchheit.blogspot.com/2007/03/how-to-be-right-90-...