The thing that I find so hard about venture capital is that you might be right about a company, but if you make your investment at the wrong time, you can lose all your money. You can be right about the destination but wrong about the timing, and it doesn't matter that you were right about the destination.
The danger in technology investing is that S-curves nest inside S-curves. You can be right about the ultimate destination and completely wrong about the timing, and if you're wrong about the timing in a leveraged way, you don't get to be right about the destination.
The companies that tend to win in technology are the ones that are able to identify the inflection point on the S-curve early enough to make a big bet, but not so early that they run out of capital before the market develops. The penalty for being too early is often indistinguishable from being wrong.
