This is interesting. A long time ago I made myself a little challenge just for fun which is similar in nature. I started out on NL5 with 1 buy in and the idea was to see how far up I could get. There were rules though. For example, as soon as you reach 100BBs of the next limit, you have to sit out and move up. Of course, you can't rebuy. Unfortunately, this will only work for ring game players. In this scenario you would be allowed to stop at any point during the challenge and just report your winnings in the end. Also, I wouldn't mind people giving it more than one attempt, as long as you start from the beginning. (in this case 2 attempts would match the $10 we have been discussing.) The winner would get the degenerate of the year award! (I managed to get up to NL50, so it means that anyone can do it!
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