Say I started with $100 and made a bet but only won 90 back. Then the next day I do it again with my 90, but only win 80 this time. Repeat this until I have $10 left, I bet that and lose it.

By your logic, I’ve lost $550, since thats the amount of money I’ve bet over the week and a half. In reality, any sane person would say I’ve lost $100.