No need to turn $1 into $20 all at the same limit. Once you turn $1 into $5, increase limits. Once you gets to $20, start the tourneys with half the roll and keep plugging away at ring games. Considering that he's probably an above average tournament player [img]/images/graemlins/wink.gif[/img], he could probably cash in a few tourneys. At a $1 tourney, he needs to be top 5 to get $100.

If he gets on a good roll, he can start at the $2 and $3 tourneys. Before long, he's at the $20 tourneys, and winning hundreds when he cashes.