Two of my buddies and I were eating at Firehouse Subs a few hours ago. One of the guys is at a crossroads in his life and i just got done doing something epic the year before and am looking for some new challenges. The third guy could care less either way.

Anyways... "crossroads" buddy and i got to talking about being debt free and how liberating it is. So in order to facilitate his process (just trying to motivate my friend) in being debt free i decided on a little challenge involving the three of us.

1. "Care less" friend has to front 1000 dollars.
2. "Crossroads" friend has to pay off all his debt in 4 months (it's a significant amount for what he makes) or he has to pay "care less" 500 dollars.
3. I have to turn 1000 dollars into 20,0000 playing poker or I have to pay "care less" 500 dollars.
4. If "crossroads" wins he gets 500 from "care less"
5. If I win i get 500 from "care less"
6. So we both get 500 if we win. If one wins and the other loses "care less" breaks even. If we both win "care less" loses $1000.

I basically have 20 weeks to win 20,000 dollars. I can play online or live. I don't really play NL ... mostly limit, stud, tournaments, and sng's. Poker isn't my job nor has it ever been, but i do take the game seriously, and would consider myself one of the better players at the table at stakes up to 10/20 limit.

This should be fun. And it would be awesome if my friend paid off all his debt since that is such an awesome feeling/situation. Plus... the incentive to shaft the third guy by $1000 is icing on the cake.

We wrote up a little agreement with some additional stipulations and all signed it for legit'ness...

since you used it as a focus of your OP I thought I should let you know that the phrase is "Couldn't care less". What you actually said is opposite than what you probably intended.

gl anyway.