It depends on the situation what are you going too, IMO I'm not good at the higher roll because every time I play in just a small value of money mostly I won but if I go with a higher roll mostly I always lose this give me a lot of problems so I prefer for safe play.
Those high rollers almost had nothing to fear.
I guess, what they are thinking is that, if they lose continuously, they will just bring their money back from a single win, given that the bets that they are betting is high.
This maybe true if you have a large bankroll but for the small or medium gamblers, this strategy is very risky. If you keep on putting more money in to gambling after continuous loss, there may a chance that you still don't win and keep losing. Many gamblers have become bankrupt because they keep on investing in gambling with a hope to win big, which never happened for them.
Because of having too much confidence in higher roller, I think they just ignore the higher money wage because you cannot earn double, triple, or any times XX multiplier if they did not risk anything. Playing gambling is risky and you are always vulnerable to lose all of your assets.
In fact, staying on high stake slots are not good luck for me. Sometimes it causes me stress. So, I lean towards penny slots most of the time while playing. In the case of roulette, always I limit my bet from 10 cents to 10 dollars, it gives me so much joy and doesn’t have the fear of losing lot money.

You can experience a lot of emotions when you start into a higher role, fear, doubt, and nervous like if you are winning or losing your money, this gives a different excitement to your self. For me I just wage for over 10-20 dollars every time I play.
Some people get the most out of their sense of risk. For example, they wager a large amount of money and get the adrenaline rush of realizing a possible loss/win. Your game strategy is good, but it won't work for those people. Maybe there are many such people among high rollers.