If you like (and are pretty good at) word-based games, you might want to check out this site called World Winner. I guess they offer a whole lot of other games too. You basically get to enter various sized tournaments for money. Some tournaments are as small as 3 players, and others don't really have a cap.
After you win a bit you have to pretty much stop playing for money though, since they track how well you do over time, and begin pitting you against better and better competition. The rake is really high... for the $1 5-player tournaments, the payout is $3.50. So, they're raking $1.50 from the $5 in entry fees. The $2.50 3-player tournaments, they pay out $6. Again, a $1.50 rake.
But, let me say that in the beginning you are likely to be mismatched. I was able to squeeze out nearly $100 before it became pretty clear that I was no longer winning the majority of the tournaments I was entering. My strongest games were Word Mojo and Scrabble Cubes.
The site has a single-player challenge for money called Top This! where you have to top a score that their system believes is 50% to be beaten given your history. For this type of challenge, they take a large rake ($1 wins $1.60 and $2.50 wins $4). Anyway, my Top This thresholds are 1389 for Word Mojo, and 562 for Scrabble Cubes.
You can also sign-up and play for free, so if you want to get an idea of how strong your game is before you commit real money, you can.
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