[droolie]

Have him start at Pokerstars play money until he understands the game mechanics (ie blind structure, betting amounts per round, hand rankings, blinds leading the betting from the flop on and why all-in players get to go to the end for free). Not too many hands but perhaps and hour worth of playing. No reason to have him lose anything while he learns that. Keep it fun at the beginning, losing any money won't help. Pokerstars has great software and decent competition at the nano's and is a great learning environment. Pacific software and game speed sucks so bad it might be a turnoff. Online poker is fast paced he should learn the right pace from the start.

Once he's comfortable with the basic rules teach him the EV concept. Teach him about the long run vision he needs to develop. Explain that bad beats are a part of the game and that they are often a sign that his opponents are playing badly which is in the long run a good thing. Teach him about patience and diligence and what to expect as far as action when playing. The idea isn't to win the most hands just the most money. This is the single most important thing for a new player. Playing less than 20% of hands is unnatural and will take a lot of understanding of the theory behind it in order for him to adopt that style off the bat. He also needs to know that not everyone is bluffing and that everyone will assume he is always bluffing. He should expect to have to show down the best hand much of the time. This is something that will help.

Have him move to the .25/.50 game until he learns the basics of strategy. This is when he should start reading SSH. If you're going to be intensively coaching him, skip inferior books like WLLH. You'll be able to explain the tougher concepts to him and there is a lot in that book that a raw beginner would thrive from learning from the start. Why teach him something (weak tight style) that he will need to break away from later? Instead giude him through SSH at the right pace. +EV theory, identifying the nuts, pre-flop hand chart (download one for easy desktop reference) and counting outs and pot odds is critical and should be taught at this point, in that order.

Postflop aggression should be drilled to him in the right doses. That is one of the tough things about SSH it will turn him into a maniac if he's not properly explained "good aggression" from "bad aggression". Sentences like, "almost any hand worth playin on the flop is usually worth raising" need to be qualified. However hand protection and pumping draws are too important to winning to wait too long to learn. River and turn play are well explained and the part about not folding in big pots for one bet on the river is pure gold.

Have him post hands and get into reading the micro forum from the start. We can help when you're unavailable and the ideas there will have him bringing questions to you and may bring him along quicker. These forums are critical for learning how to read hands and understanding betting patterns and what they mean.

Once he fights his way through .25/.50 at stars and earns 300BB he will be ready to crush party (help him get the best start up bonus available) That is when you introduce pokertracker, player ranking, playerview, data mining, and multi-tabling. Finally teach him bankroll managment, bonus whoring and advanced aggression both preflop and postflop, get him off using the hand chart.

That's how I would do it...