I've gotten six people to join, and I think if they live near you the best thing to do is sit them down and show them first hand the important aspects of the site and speak with them regularly about what they should be doing. Four out of the six still play and three of them are supporters, those three all have been receptive to my suggestions and they really love the game now. Two of them may win their divisions, partly because I had them come up with a short term and long term plan, which I feel newer players don't do.
The hardest aspect for me to get over when I started is the lack of games throughout the week. I didn't understand how scrimmages worked and I wasn't very interested in my team the first month (luckily I had no PS3 or TV, just a comp). It seems like that's the case for some of the people I've spoken to, they just don't know what to do. Another gamein a cup format is a brilliant idea, and perhaps we should reach out to a new player when we see they've joined our league. A "date joined", on the team page, perhaps under country rank would help?