It's even worse when the person who had the luck/timing in a previous success sets out to recreate that success and doesn't adjust to the changes that have occurred since. At least one such startup I've worked at the CEO had what we referred to as "Delusional Rich Guy Syndrome". Many of the investors he teamed up with also shared the same disease.

It's the idea that somehow, all the other people that failed lacked their special innate abilities so this time it will be different.