I think your google point is spot on. I wanted to stay away from this and thought that the content creation route might help mitigate this.

Would you agree that there are three types of online businesses:

1. Businesses that rely on engineering(twitter, Facebook, google). These are businesses that you for sure want to stay away from.

2. Businesses that are basically e-commerce. Zappos, Amazon, etc. This would be tough to do because of the need for inventory.

3. Content businesses lifehacker, wine library, etc. These are ideal because they require little/no capital and only hand work put in by the students. This handwork can then spread over 4 years and hopefully they have something at the end of 4 years to show for it.

As far as home runs vs bunts and thinking they would all be successful, I'd be happy with 1% success rate.

Thanks for the awesome input.