I debated with myself on whether to use "naive" but it seems the most appropriate description. I barely know Woz outside of a 3-hour lecture but it appears that Jobs took advantage of his naivete, lying to him on multiple occasions. It worked out (financially) for Woz and he seems to have a great attitude about it, one of the reasons I admire him. He seems to successfully walk the line of not caring if people take advantage of him while not getting wrecked. I think it fair to consider that a facet of being naive.
I think "innocent" and "guileless" also bracket the sense you're going for, but they don't quite fit either.
Like, he doesn't see the malice in other people, but its not because he's innocent/naive of such intents, nor does he lack the skills to look for it (guileless), but because (as you say) he doesn't care if people take advantage of him, up to a limit.
I think “grounded” might be a better term vs being naive in this context. People can suck, sometimes a person who sucks is going to take advantage of you, and it’s a choice to handle it in a mindful, positive way. Monk vibes.
It’s not being unaware (naive) but rather a lack of cynicism. I think that’s an important distinction to make. It takes an extra dose of intelligence to avoid cynicism when you are at that level. Cynicism isn’t wisdom, and its absence isn’t naïveté.
