I find it freeing to know that no one really knows what they are doing. Looking into startup world from academia, it seemed like these people really were thoughtful and strategic in how they operated.
After getting into a couple very well funded startups, and seeing how the sausage is made, you realize that no one knows what they are doing. It's not that they're stupid, just that business is hard and the environment is always changing. Sure there might be some "master of the universe" types, but you can create a good business solving the most immediate and pressing problems.
Getting someone to give you money for a product is always hard. We see things all around us that we and others pay for every day, but that's just survivorship bias. It doesn't stop many of us from thinking it's easy, "there's n-billion people on the internet, if I can get 1%..."
I'm not sure why anyone would think the people running these companies are any more intelligent than anyone else. In some intellect measures like emotional intelligence they are even often quite weak.
I was a young kid during the dotcom bubble and in highschool during the '08 downturn so I wasn't really aware of the macroenomocic trends in the industry then, but now that I am older and deeply invested in the tech economy it's so obvious.