Given your analogy, it seems to me that if one wants to work for a start-up it would be wise to vet the CEO as much as they should vet any engineer. Naturally, not all CEO's are created equally and not all of them are bound to succeed. However, if one can determine which CEO's are good at problem solving and making good architecture decisions (maybe based on existing business design patterns?), then it is possible to at least narrow down which ones are likely to be more successful, and thus leave you less frustrated.
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