I view this as being smart. Box is under heavy competition not just from Dropbox, but from Google and Microsoft. 4% of $250 million is better than 50% of $0. The landscape is littered with founders who drank the koolaid and thought they were going to billions and ran their companies into the ground. Maybe Levie won't own 50% of Box, but maybe he will own 4% of a viable company with a real business going forward. And if all else fails, he'll walk away with $10 million.
That's a "problem" I'm sure many of us would like to have.
They'd be raising $250mm in the IPO. That wouldn't be the valuation of the company. Presumably, it'd be >$2B which was the value of their last private round.
Your point stands in that 4% of that isn't too bad either.
That's a "problem" I'm sure many of us would like to have.