There are a *lot* of geeks of my acquaintance who have made suboptimal career/business decisions simply because they were coming at a nuanced, detail-rich topic/transaction/etc for the first time, did not have the right person in their network, and ended up YOLOing it.
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Interestingly a lot of the traditional answers for "Who is the right person?" are disastrously wrong. For example, you might think "Ah, I am going into a high-dollar transaction in Silicon Valley. I should get a lawyer." *Almost all lawyers* are not going to be effective for you.
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It's also really difficult to evaluate expertise, because substantially all comments on e.g. Hacker News about raising a Series A round look the same. Some of them have rather little entanglement with reality. Some are from world's leading practitioners (from multiple angles).
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