Those are institutional investors who are more sop

Those are institutional investors who are more sophisticated (supposedly) and they always get more info. Joe obviously thought they would get the S1 approved by then, but FINRA held it up. That was unforeseen. And Discover probably knew it was a long shot, so they pushed for that date and if Joe was in dire need of the money, he would put that date in. So Joe may have looked at it as costing 20%+ if we don't get it done. And maybe he was led to believe by Discover that they would give more time and Discover pulled a fast one.

Disclaimer: Of course, all of this is my opinion and you should not make any investment decisions based on my opinion. I have not received any non-public information.