I would mention that your topic title and the body has some kind of contradiction, so I would like to reply to your title instead.
First time winnings are just like a magic, unbelievable and very engaging. It has a way of falsely making you believe that you would be profitable in the long run and you throw in everything in you to hit it bigger. I would always mention that my very first win in gambling which was over $600 was very substantial to my addiction struggles and that of my friend who initially hated gambling. I thought I have found a safe heaven and would continue winning, but reality struck me and I was devastated.
First time win can act as a trap to take gambling more seriously, only those with either a mentor or proper orientation on gambling in moderation can really try escaping such traps.