Stop caring about money

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I just started working in a legal way, before that I would get money by bday gifts or doing some simple jobs. I found out that i'm like Mr Crabs with money when I want to spend it on me.

Idgaf if I spend on a friends bday, or on a meeting at a bar, but if I want to spend it on me I spend hours looking in the internet to make sure I don't waste my money.

I play Dota and I got near 30-40 USD for free by playing on local tournaments and shit like that, started betting for the lols, made it up to $60 and then I lost it all.

Since then I've been a pussy dude with no confidence on his decisions and I became even more Mr Crabby with the money (luckily I still enjoy spending it on my family and friends)

Every time I remember those $60 bucks I feel dumb as hell. Luckily I promised myself since I started gaming that I would never put a penny on virtual items or fucking pixels. I mean, it's not even that much money but I really feel stupid.

Tips on how to improve this? (I'm never gambling again btw, I did it because I got all that for free but it was stupid as hell anyways)