The counter-intuitive nature of startup investing is a big part of what makes it so interesting to me. In most aspects of life, we are trained to avoid risk and only pursue "good ideas" (e.g. try to be a lawyer, not a rock star). With startups, I get to focus on things that are probably bad ideas, but possibly great ideas. It's not for everyone, but for those of us who love chasing dreams, it can be a great adventure…
The hidden premise of that statement, appears to imply there exists a universal intuition to which this is "counter". I'm not sure that is completely accurate, and is perhaps more useful to think about it in terms of a bifurcated process that can roughly segment the populace into two modes of preferred intuitive operation, but possibly more.
Without going into detail, both types of intuition make subconscious predictions, yet do so in markedly contrasting approaches, which may explain the root cause of arguments between a priori/a posteriori, bayesian/frequentist debates. The underlying ideologies may not necessarily be the effect of environmental upbringing as often assumed, but could instead be structurally rooted in the fundamental wiring and decision making of our cognition.
I'm sure some will disagree, but I naturally find frequentist methods rather challenging to understand, and typically intuit in a distinctly bayesian manner (which is probably less common, typically VC's tend to be good pattern matchers and skilled numeracy - aka natural frequentists). Coincidentally what PG thinks is counter-intuitive (like in this article), could seem rather intuitive to some. Likewise there are almost certainly other insights that are mundane, boring obvious and intuitive to PG, yet are highly counter-intuitive (and interesting) to others.
Of course it's all just anecdote and opinion for now and probably a controversial position, but hoping advancements in cognitive neuroscience research, would one day be able to test this empirically.