Let's say you have a million people. They each roll a 6 sided die. The odds of getting any one number are 1/6. The odds of getting any given number 5 times in a row are 1/6^5 or about .0001286. Out of your million people, 128 of them will probably roll e.g. 3 five times in a row. It doesn't mean they have a particular talent for rolling 3s. If you get the million people to roll 5 more times, probably a different set of a million people will roll all 3s.
I'm not saying there's no skill involved. There are certainly things you can do to guarantee failure. But if someone has 5 successful startups in a row, it's not easy to distinguish them from someone who rolled 5 3s in a row. The population of people who've done startups is pretty small, relatively speaking.
This is reminding very much of the debate around the Efficient Market Hypothesis, as to whether traders can be systematically good vs. just repeatedly lucky. There is a lot of lit on this issue.
I'm not saying there's no skill involved. There are certainly things you can do to guarantee failure. But if someone has 5 successful startups in a row, it's not easy to distinguish them from someone who rolled 5 3s in a row. The population of people who've done startups is pretty small, relatively speaking.