When considering ideas, asking “How might it work?” is more interesting and constructive than asking “Why will it fail?”
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How often are the founders surprised by your answers to this?
More often than not. It's very common for people doing new things (generally, not just in startups) not to see the full implications initially. It's arguably a point in your favor if you can't, because it means what you're doing has a lot of potential.
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Do you find that those startups do better? It seems like it would be a very promising signal on the idea, but not necessarily on the founder (except inasmuch as they had a good idea).
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There is, unfortunately, no correlation. How startups do depends almost entirely on the founders.
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