Even Chris Sacca says it in the video: "It's almost like the game is rigged". He got lucky at the beginning and now that he has tons of money he can afford to diversify his portfolio enough to be able to buy all the lottery tickets. On top of that, he has become the legendary Chris Sacca, so the probability that the next big thing won't be presented to him at a very early stage is very low.

So it's not only the survivorship bias, you have to add to that the Matthew Effect [1].

And I'm not denying that he is probably smart, has people skills, hard worker... The thing is that, in my opinion, there quite a few Chris Saccas out there that never got as lucky as him. So the survivorship bias here doesn't nullify all his work, since he showed that if you do the things his way you can get the chance to become the next Chris Sacca. It only shows, that even if you follow his path you can still fail.

I realized that people that don't see the survivorship bias tend to view people that do as cynical pessimists that downplay the hardwork of the Chris Saccas of the world. But this is just a problem of perception, at least in my case, I admire the Musks, the Jobs, the Gates, the Buffets... of this world. However I realize that in order to become like them, it takes more than just hard work and a vision, you have to get lucky and preferably be born white, to well educated and relatively wealthy parents, in the right country, be sent to a good school...

I like to consider myself a realist, if somebody gave me 80% of the lottery tickets I will probably be really hopeful that I will win, but if I only have 0.001% of the tickets I won't probably even remember to check the outcome. I want to believe that that does not make me an optimist in one case and a pessimist or a cynic in the other.

[1] http://en.wikipedia.org/wiki/Matthew_effect