A "lucky break" is more likely to come along if you keep at it for a decade than if you give up after the first non-successful year.
I think skill comes in two forms: The skill of making something that people want to use, but also the skill of recognizing and making the most out of "lucky breaks".
There is an element of being at the right place with the right idea when people are ready to embrace it. But certainly there would be plenty of startups where the stars aligned for them in terms of this and they never managed to make it big.
Luck is not all it takes, but these sorts of self-congratulatory stories (and the hagiographies written about such people after they succeed) always seem to downplay this particular element of the story. Having a great idea and a great team are not enough and sometimes those who "get lucky" can make do with substandard ideas or teams. It is hard to admit that the most significant determinant to success is completely out of your control, but if you accept this fact and plan accordingly you will be better off than someone who things that their superior team and idea are all they need.
A lot of the success of agile businesses and the whole mvp product strategy could be explained by the fact that it embraces the possibility of randomness and unexpected outcomes rather than ignoring it completely.
A lot of scientists, interestingly, are willing to admit a luck factor, especially when it comes to doing something Nobel-Prize-level world-changing. Some really did know exactly what they were doing, and it worked. But a lot of scientists frankly admit that the big career-making thing they did wasn't even something they thought was important at the time--- and sometimes nobody else thought it was important either, and it languished in a journal for 10 years before someone else noticed it had big implications. Of course, that's not purely luck, because they'd never have had that opportunity to get their work belatedly discovered if they hadn't done good work on interesting problems, and published it. But there does seem to be some element of luck in the work turning out to be huge. There are plenty of people in exactly the same position who do good work on interesting problems, write a good journal article, and it doesn't turn out 10 years later to have unexpected but important implications, winning them the Nobel Prize. Just sort of how it happens; you can't always predict what is going to turn out to be important.
I could be wrong, but my impression is that wealthy businessmen are somewhat less willing to admit the role of luck than famous scientists are. Due to real differences in the role of luck in the two areas? Due to political considerations (the implications of admitting that wealth disparities aren't all due to merit are more political than the implications of admitting that scientific fame isn't purely due to merit)? Due to the self-deprecating scientists being humbler personalities? Dunno. And I could be wrong on the aggregate difference; I haven't done a survey or anything.
Luck is important, no doubt. But a)first you must follow your heart; b)you must do great work; and c)then you probably deserve some luck, too, and/or create your own luck.
