IIRC, the last two investors had some sort of deal where if the IPO was priced at under $20, Box paid them some sort of penalty. (Maybe someone here remembers the details better than me.) I'm sure they watched their backs on the paperwork and that any gain like the one the stock is currently seeing is a win for them.

As sbisker said, the last round investors had preference protection in the form of a ratchet (i.e. they got some multiple of their shares because the IPO came in under a certain price). EquityZen seems to have updated their piece

>Those last two major investors lost a lot of money.

Depends, actually, on how much of their stock they sold at the IPO price. Box is already trading above the last round valuation even though the IPO was priced below it.

Well its such a late stage investment at a very high valuation. Either they did it for the portfolio logo, or they just want to make a safer investment that will cap out at 2x or 3x at best.