It is a shame for Chicago that groupon didn't continue to find success. I really think that if they had continued to grow the Chicago tech scene would be significantly larger than it is today.
Lefkofsky and the underwriters butchered the IPO for personal gain. I don't think it was a viable business model but they could have at least tried to steer the ship.
Citadel is moving to Miami because Chicago government sucks - the move was due to "riots, an employee stabbed, and the attempted hijacking of his Ken Griffin's car"