Catching one trend, like Mark Zuckerberg, is just luck. But there’s clearly CEOs who are able to predict the direction of markets over a sustained period of time across multiple inflection points. E.g. Bill Gates and Steve Jobs.

I would still treat this like John Bogle treated mutual fund managers.

For every Steve Jobs there are a hundred Carly Fiorinas

Eh, even if we take those mythologized examples as real (I'd argue the history of both is heavily whitewashed and their failues, like NeXT or Windows Phone to name just two, are papered over in their mythmaking), if anything they're the exceptions that prove the rule.