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While it's not easy to hear, I got one such advice once on a company I started, and in true entrepreneurial spirit ignored it and kept iterating away. It was 100% spot on.

I wish people were more frank about what they think of start-ups, and I wish there was an acceptable way of doing that without insulting people.

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In Italy for example is the exact contrary of the silicon valley mindset where everybody will say "cool!". You will likely get criticisms like "it's nice but will hardly work" and so forth. This has the effect of discouraging people a lot. However as you said, the reverse is also dangerous. There must be a middle ground where it's possible to get balanced criticisms that make founders aware of the risks of a given business.

Not only balanced, but constructive and well thought. Saying "this sucks" or "I can't believe anyone invested in this" is useless. The above criticism, while not very constructive, is still grounded in facts (that I can't judge since I don't know the field enough) and goes beyond "this won't work"

Yep exactly, a good mix is "cool but make sure you think also at <constructive critics about what could be dangerous>".

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