As long as you don't play too long and you are winning and cashed it out, you are technically a winner.
However, if you play longer time and even while having lots of winning already, tendency is you are going to lose because of the house edge advantage.
But we never know what will happen at the next bet so we just have to play as much as we want until you finish the quota of money for gambling.And also we have to go with the mind set of possibly we are going to lose today as well so just take less money,if we win then its our day and enjoy it.
But if we continue the game, we have a big chance to get lost the money without any chance to get another winning. And I think it's about probability the chance for us to win or to a loss in the gambling game and we need to wisely to think about to continue or to stop the game. And if we don't want to get lost in the next round/bet, we need to get out as soon as possible from the gambling places, and it's better to cash out the winning money.