Rumor was they had a weird liquidation preferences in that round, which made it more like debt. Something like a 2x floor and 3x cap. Not sure how that resolves in an IPO though.
First, the "vs Box" valuation above is simplistic and may not be comparing apples to apples. They are competitors but they are not identical companies, so scaling valuation based on a couple of inputs fails to capture all of their dissimilarities. Also, there is no consideration for a relative spread between the two if you value Dropbox directly off Box (or in other words, which one trades over).
Second, the IPO is not always priced efficiently. Some executives might prefer to price lower just to see positive headlines about sustained gains after IPO. Others may counter that a low IPO price leaves money on the table.
You should wait to see where the stock trades after IPO and any significant lockup expiries before evaluating the success of investors in the $10bb round.
