how good was Taleb at following his own advice? Had he tested it? As I recall he is pretty big on "skin in the game' as his differentiator.
Leverage scales in a way, because larger pools of money (corporations, groups of investors) mean larger bets.
But leverage also doesn't scale, because larger pools of money tend to make smaller bets over a larger surface of the market, since being wrong in a big way with leverage can wipe you out.