Lose it the first time and when the pot is between 1000 and 5000 gold on the second try, use the card your opponent used the first time to beat you
If you decide to do it when the pot is over 5000 gold, your oppponent will do it first and you'll lose the money (since your bet will take it over 5000 gold ALWAYS).
The general idea is - you lose 1000 and you can get it back with some extra