It's happened at least five times, I'd say. Usually two sharks going head to head (Like O'Leary and Cuban) and when they ask the person to leave the room, they collude to join in on a deal. I also remember it happening with Kevin Harrington on one deal. It also happened when Damon and Robert went in on a deal together. I even remember one where O'Leary wasn't even in on a deal, was already out and when the person left the room, he said Cuban gave up WAY too much by saying "in perpetuity" in a commission deal offer, rather than just until Cuban got his initial investment back, then the commission should end. And they totally slipped that in as if it was nothing. It was a huge change to the deal. Each time the people got a scaled back offer, or a collusion offer that negated the original offer on the table before they left the room. If Cuban can do his "24 second clock" approach (which doesn't allow the pitchman the opportunity to leave the room and think,) then if I had two competing offers on the table from two sharks, I would never leave the room.