The ideal stance for a good startup advisor is actually short term pessimist, long term optimist Short term optimism that is false leads founders astray: It's like unintentional palliative care. If you say it's OK and it's not, your startup will fucking go in the ground.
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The fundamental transition from startup to big company is when you go from needing that advice to instead needing to be told “this could be bearable if you fixed all the horrible bugs in it.”
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“just make 100 users love it so much they recommend it to their friends”
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