That is how it starts. At first it looks cool and you win money in the beginning but as you keep playing on you lose more money.
It is at that point when our emotions kick in and tell us to keep trying until we win more money.
But at that point of time we should stay calm and think wise. If we chase loses we lose more and that is why we need to set our own guidelines and strictly adhere to it.
Even from the start, the possibility of winning your bet is still based on luck because it's a 50/50 probability. It might still look cool even if you lose your bet in your first few tries. Once you have lost everything, you get emotional and start to gamble revengefully in order to just gain back the funds you have already lost. If reverse is the case, like the way you suggested, when a gambler starts gambling, they can win some rounds, which will motivate them to keep gambling even if they are losing. They will still believe that they have had the same streak of luck as when they initially started and lastly they end up still losing everything.