I don't know about other people's gambling experience,  and I will tell that if you want to win... limit the number of games on the betslip and put a decent amount of money that you can afford to lose, but the second you choose to inflate your winnings by making  some insane accumulator your winning chances are lowered instantly !!!

So coming back to the topic, I assume if the Rich gambler isn't taking risky bets then they are more likely to be profitable unless they are greedy which guarantees a bust but for the other person without the needed funds for a tangible profit they are likely to take  much higher risk as they try to win big.