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Not sure I agree that it's critical to get it right first time, but at the appropriate time.

Even if you have incorporated, it is possible to do a NewCo later with a different structure and roll the startup business into the NewCo.

Your company incorprated name does not have to be the name that everyone knows you by (trading name/site name).

Isn't this what Facebook did when they needed to bring in further investors way back when?

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Hear your point, and agree generally, but parts of this are definitely critical. For example, you have a hard stop window of 30 days to file your 83(b) election. If you miss it once, it is gone. That can create millions in additional tax liability if you have a successful company on your hands. If you don't have someone watching for stuff like this, it can mess you up pretty bad down the line, regardless of if you roll into a new company. Fixing problems that could have easily been avoided often ends up being costly.

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