I have been doing the big company thing for a number of years now after exiting successfully as employee number one of a small startup and having to shut down a larger and better funded startup where I was CTO. Since then, I've done quite a bit of thinking about how to be successful should I choose to do a startup again.

The conclusion that I have reached is that the best approach is to find a boring problem. There are so many legacy industries out there that haven't changed in decades. If you can improve one of those, you're basically printing money. This was what Uber did for Taxis. A couple of examples of startups that I've run into lately that are doing this:

ripcord.com: record storage is a multibillion dollar industry in the US alone and is largely controlled by one company that is a hundred years old and has not modernized. spruce.co: title insurance is also a huge industry that is dominated by old companies with zero technology. If you've gone through the process of buying a house you know how ridiculous the signing and title transfer is.