I think it completely depends on each person individually. Everyone is a bit different in how they handle and or spend their money when they've got a lot of it. A lot of people worked hard for that moeny and aren't willing to just give it up so easily. Others may have worked hard but have no problem gambling with it, as perhaps that's how they became to have so much money on hand, taking gambles in life.
You are very right, atleast, I know of someone in a city where I used to live before I relocated to where I live right now. This guy grew in business and is doing extremely well, back in those times, we were all friends and normally do sit together every evening to play some games which involves us staking some money at times.
This guy will only join us to play the game when ever we are having a free play, but when ever we decide to bet money, he will simply opt out and just sit aside and watch. One day, I personally asked him why he doesn't like to join us to play games when ever we are playing for money, he simply told me that, he worked really hard to get to where he was at the time, that every penny is so important to him and his business, he can't afford to lose any of it even though there is the possiblity that he could win more in the process, but that he doesn't like to depend or put hope on things that are not certain.
Your comment made me remember this guy, he is a true definition of a man who made money, but can't enjoy it because he feels money should be preserved, and not be put into things that are high risk, like gambling.