Yes, Dropbox was in the Google category of bad ideas: there were already lots of similar things. Success turned out to depend on execution. Dropbox was the first application of its type that worked sufficiently well. But that sort of thing is hard to predict.
Turns out my memory was only half right. DropBox had many people that loved the idea and thought it would revolutionize filesharing. It also had a large number of people who pointed out all the reasons why it wouldn't work.
I wonder if there's a lesson here in that good ideas that seem bad tend to be highly polarizing. I've recalled Paul Buchheit say here that GMail met a lot of internal resistance, with many Googlers saying it was a distraction and would never work. I also recall Larry saying that there was significant support for GMail at all levels of the company, going up to the founders, and many Googlers loved it.
> I wonder if there's a lesson here in that good ideas that seem bad tend to be highly polarizing.
Yes -- exactly -- and they tend to generate a lot of heat in group discussions. One of the indicators we watch for are people getting visibly angry during the discussion -- either angry that other people aren't "getting it" or angry that other people ARE "getting it".
> It also had a large number of people who pointed out all the reasons why it wouldn't work.
To be fair, it's not actually possible to present a new idea on this forum (or any forum with technical-minded people), without getting a flood of reasons why it won't work.
I asked a similar question of paul down below but it seems to me that big successes can come in 2 flavors:
1) Execution driven success in a winner take all market. The idea seems good, but there is lots of competition so it's hard to see how the startup will break through & win the market.
2) A genuinely "good idea that initially looks bad" like you describe in your essay.
It's hard to think back and decide which, now successful, companies are 1 vs 2 because of the memory distortion effect, but it really does seem to me like #1 is more common. What do you think?
I'd give bonus points to #2 if the idea seems so bad that you go though periods of doubt yourself, but keep on returning to the view that "it's great".
If you're absolutely certain of yourself, chances are that there are others out there who are just as certain, so you will have competition. If you're uncertain, and feeling lonely, there's a better chance that you have the field to yourself.
My experience of this is being involved in the development of the first WiFi (802.11a) system. It was only with hindsight that the significance was clear. The reality at the time was an isolated toil in the dark, not a high flying roller coaster ride.