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Gamble every day will potentially makes him becomes addicted to gambling if he can not control his minds. And that will be more risky for him if he wants to recover his losses because that can make him spend more money easily.
He need to know that when he losses his money in gambling, he must stop gambling and not continue gambling or even trying to get his money back because that can makes him lose more. Losing in gambling is usual because gambling itself is not a place to make money. So when he can consider gambling is a place to have fun, he will not lose too much but that still under control.
He can still playing gambling every day but he must have a strong control for himself so he will not get tempts from gambling.
The story main problem is not about his frequent gambling like daily basis. It’s about his greed that doesn’t give him contentment for what he already earned.
He experienced already winning twice with a very huge amount yet he still play without any target profit until he bust almost 60% of his profit.
Although he is still on the plus side, The pain of losing the 60% is still there because that money was already mine and just loss because of greediness. You can suffer to gambling addiction even if you are not playing daily as long you don’t have any bankroll management.