I'd say I pretty much do the same, only in reverse. In real life, I'm much more likely to take a risk which might or not pay off. When I gamble tho, I tend to be more cautious and reserved, as I understand chances are against me, and substantial losses could happen quite quickly. The attitude helped me save a lot on Roobet and Dplay, and only once on Stake I actually lost some money I considered to be something I didn't want to happen again, so that only reinforced my future behavior.
I don't think this is funny as it is a mixed behaviour. If you don't do a thing in real life but doing otherwise in gambling, that will certainly not be good and it could easily bring out the irresponsibility in that person. What the guy is doing is reckless and if he continues that way, it can't never have that happy ending, which is why it is good to be careful even from the beginning. Some people have their near-perfect behaviour, and some can even help you to plan your life and you will hardly see a fault in their doings and the way they handle matters wisely. But that does not mean they are without faults too, they are humans too. They might have their devil one way or the other, and it is good when it does not involve money, but in the presence of money, another issue might arise.
To you, the person might be okay, but he is not, the psychology that is attached to money is different from the one that is attached to behaviour without money. All that matters is for someone to be cautious no matter how good you think you are, and whether it is in gambling or not and maybe other things where money is also involved or not, we must not be egoistic, we must not let ourselves to be affected or being driven without a control. If money is being made, that is a different ballgame, but when money is being lost regularly, C'mon, it is bad. No one is perfect and motivation might creep in when we least expect it, which is what might cause some people to believe they can do it better again but will keep on wasting money. There is nothing better than discipline and being neutral in gambling, and when you have a good plan and budget, it makes it better.