April 5, 2007: "Show HN, Dropbox"

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.

Sharp criticism from know-it-alls is often a sign that an idea is good. It's amazing to me how, even though this is common knowledge, good ideas continue to polarize. I'd hate for you guys to convince everyone to be so nice that we skew this long-trusted signal :)

I'm still not using Dropbox. I absolutely detest the idea that I'm relying on a 3rd party for a feature that I consider should be built into every modern Operating System. At the point when OS vendors relinquished to the Web 2.0 Cult their responsibilities for such features as easy filesharing, the world lost something.

Absolutely, its great that people can share files this way. But absolutely, its terrible that it requires fragments of an OS feature to be distributed among multiple, external, unreliable entities.

Why should OS vendors also supply cloud storage?

Who would provide this cloud storage for Linux distributions?

Honestly, I still think the idea of dropbox is ludicrous. There are many ways to share files, and sending them to a third party to host for you is the worst one of them all. Aside from the few people that really need to multiply their bandwith by many orders of magnitude, a simple file sharing server on their own PC or a server they own would do the job just fine. Besides, dropbox was just yet another iteration of online file hosting (I'm pretty sure rapidshare and megaupload predated dropbox by years), so if file sharing was going to blow up, it would have already, right?

And therein lies the true genius of dropbox. The technology itself had already been done to death; the key was to convince a critical mass of people that this was the solution to their problems. Or even better, convince them of a problem they didn't realize they had. Yet again we see that many times success comes down to the better marketer than truly game-changing technology.

(to be completely fair, their syncing mechanism was the best up until then, plus their add-free freemium model was likely the missing key to success in this space)