Square's IPO prospectus shows just how much the company needs a full-time CEO

This article cites $56 million in losses from the Starbucks deal. Another post [1] cited it around $70 million. What was the angle here? Did they somehow not realize the financial hit this would incur as a result of the deal?

[1] http://www.geekwire.com/2015/square-lost-more-than-70m-on-de...