Maybe, except poker has a fixed set of contexts. The hands you can hold, the hands your competition can hold, the winning and loss conditions, are fully enumerated. And you still can't assume that someone who did really well at a professional level can teach others to play at that level. How much worse in the land of startups when none of those things are fully enumerable or known?
If you want to draw that analogy, I think Pratchett's statement in Good Omens about God playing dice with the universe is more accurate - “God does not play dice with the universe; He plays an ineffable game of His own devising, which might be compared, from the perspective of any of the other players [i.e. everybody], to being involved in an obscure and complex variant of poker in a pitch-dark room, with blank cards, for infinite stakes, with a Dealer who won't tell you the rules, and who smiles all the time.”