How do you feel about people outright asking you for money?

[Sully]

.....teach a man to fish, and he will never go hungry.

If these are people who you really wnat to keep as friends, tell them you will help them learn to be a good player if they are willing to work. Force them to understand the basics before they ever play a hand. Make them read books, study, the works. Turbo Texas Holdem isn't a bad way to make them grind out some free hands with decent competition. The free tables on these sites actually make you dumber.

Then set them up with a small bankroll that you are willing to never see again, under an account that earns YOU rakeback. Let them know this is exactly what you are doing, and that their rakeback is your fee if they ever become good. Make them feel obligated to keep that account if they continue to play, but expect that you will probably have to give some back when that day comes.

And when you think they are ready, let them take a shot and move up the levels. You will have accomplished two things:

1. "Given" them the $300 (or $500) or whatever they asked for
2. Shown them just how hard this "easy money" is.

And one out of ten may actually become a good player and earn you a little money. The others probably won't be willing to work hard enough to even get the initial stake, and will stop asking for money.