> I’m saying someone pursuing that portfolio will probably end up underperforming an index.
This holds if you consider "underperforming" to be a comparison of expected values.
On the other hand, if you consider "probability of getting a really huge payoff" to be the measure by which the investments are compared, the index fund is the one that looses in the comparison.
Would you be comfortable using this same logic to invest most of your net worth in lottery tickets/betting on black in a casino? If not, I'd be curious to hear what is different in that for you.
> if you consider "probability of getting a really huge payoff" to be the measure by which the investments are compared
That’s gambling. You’re truncating the curve below the top. It’s a terrific strategy for middlemen. Its expected value is lower than index investing.