I've always been obsessed with the $1 to $10,000 challenge. Taking a bankroll of $1 all the way up to $10,000 playing
online poker. Back in the day Chris Ferguson supposedly did it multiple times.
He said it took months and months. And be prepared to go busto multiple times. Its super hard to just get that $1 to something like $15 or $20 just to get started. He wrote a few articles outlining his bankroll requirements and progress, I'll see if I can dig them up on the interwebs...