If you are in the industry you will realize that it is extremely difficult to be consistently right. His success is not attributable to pure luck only.
If you have enough people guessing coin flips, one of them will be consistently right... and then claim credit for how difficult it was. Just look at all the people who failed!
Taleb is big on this idea applying widely in the finance sphere.
For what it's worth, Taleb called Ray Dalio a "legendary investor" in his book antifragile.
That is really not the case here. Look at Jim Simmons for example. And also Taleb is a brat who thinks he is the greatest investor ever to live just because he knows what martingale is.