This is one of the key seeing-like-a-financier skills that I wish entrepreneurs would learn. People are excessively risk-averse or are handwavy trying to convince counterparties that something is no risk. It's better to enumerate, quantify, and appropriately allocate the risks.
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e.g. If you think it is possible that a product won't be materially adopted, it is worth asking "Hypothetically if it isn't, is that more likely to have been market risk or execution risk?" This determines how you'd interact w/ team and what things you'd do to cheaply estimate.
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(Market risk = "We did everything right but customers just didn't want it." OK, prior to doing everything, go ask customers whether they want it. Execution risk = "Customers would have wanted this but we weren't productive over product cycle." OK, what's a leading indicator?)
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