If you include miniscule probability but huge payoff upside events, you can chase some ridiculous things. My favorite is when the powerball jackpots is over $300MM or something like that. Even after taxes (with lump sum payment) its positive expected value and pays off in days if you win. That would suggest you should take all your money and buy lottery tickets.
Lets say you have interest 100 companies over 30 years, which is pretty hard to do anyways. What percentile event is it that you get a piece of a 1E-6 event in one of your companies? Pretty low.
My thought is that you don't increase your wealth meaningfully and especially don't feed your family with lottery tickets. And that is the exact example I brought up.
From the article : "More likely, you’ll end up with a solid 2x-5x return from a startup that grows into a viable long-term business." Also, if you look at the expected value contributed by the unlikely 20x return, its .4 out of a total of 2.35.
He's trying to hit hard ground balls, not homeruns.