Took me a bit to get this. From the looks of it, you have to be losing for the whole game. So Get a phone and your web browser or 2 phones and start a game. Play and keep one account in the lead. Probably best to get all the answers wrong on the one account.
When it comes to the Jack Attack. Use the account that is winning and get the wrong answers for all 7 Jack attack questions as much as possible. The leading account will lose $2,000 per wrong answer and will easily fall below your other account and they will win.