Sometimes people gamble and stop gambling not about money or pleasure but there are other things that encourage them to stop gambling or keep gambling. A gambler who is currently becoming rich in his developing business, maybe they will not gamble anymore because they do not have free time to gamble. They chose to focus on developing their business rather than gambling. But there is a poor gamble who surprisingly becomes rich after having a big business and they continue to bet because he feels less satisfied with the results he gets from his business and tries to find greater than gambling.
In conclusion, all of that is about their own thoughts and all have different mindset.