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What are good questions to ask a CEO of a startup in an interview about its product?

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Where do you see your self and the product in 5 years!

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What are the impediments to achieving that 5 yr plan? (Then discuss how you'll be able to help them address/overcome some of the impediments. At the end, say something like you have several suggestions on others, and you'll bring them up after you start.)

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What's the weakest/least adopted feature of the product? What would cause the product (or company, if it's a single-product startup) to ultimately fail or lose traction 3-5 years from now?

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Ask him what's different from day 1 to present. And what do you think will be different after couple of next years.

From my partner, who’s a CEO/founder: 1) how many users do we have to help to reach a $100M run rate?

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