Comment by Miraste

This might be true for a normal definition of success, but not lottery-winner style success like Facebook. If you look at Microsoft, Netflix, Apple, Amazon, Google, and so on, the founders all have few or zero previous attempts at starting a business. My theory is that this leads them to pursue risky behavior that more experienced leaders wouldn't try, and because they were in the right place at the right time, that earned them the largest rewards.