Two ways. One is by exploiting some sort of flaw in the way the game is run that means the house doesn’t have the advantage they think they do. This rarely works – usually the gambler is wrong and gets taken to the cleaners, on the rare times they’re right the house is going to frogmarch them out the moment they realise what’s going on.
Vastly more common is by playing games (mostly poker) where you aren’t competing against the house but against other players. The house doesn’t care who wins because they get their cut regardless, and if you’re good enough you can make some money – in the long term at least, these games are still random enough that you can have nights where you lose badly even against lesser players. Often these gamblers will have someone with real wealth putting up the initial cash in return for a cut of the winnings.
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