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Doesn't the fact that it popped $20 per share mean that they screwed up the price, and left money on the table from the initial chunk of stock sold?

Not necessarily. Only if the share price remains this high for the next month or so.

All shares "pop up" on the first day or so. The question is if investors are willing to continue to buy the stock at that rate.

> All shares "pop up" on the first day or so.

Unless the ticker is "FB"...