Very interesting discussion — see “#AskJason at The Last Mile tech accelerator & training program at San Quentin State Prison” ( http://thisweekinstartups.com/askjason-the-last-mile-san-quentin ) — but I have at least two problems with what Jason said (or didn’t say).
First: He didn’t mention his own language skills. This is amazing mostly because Jason’s success is really pretty much all about the word „weblogs“. According to wikipedia:
Jason McCabe Calacanis (born November 28, 1970) is an American Internet entrepreneur and blogger. His first company was part of the dot-com era in New York, and his second venture, Weblogs, Inc., a publishing company that he co-founded together with Brian Alvey, capitalized on the growth of blogs before being sold to AOL.
Second: When wrapping up, Jason mentions „strength in numbers“ and that „entrepreneurship is a team sport“. While I agree with what he said, I find it ironic that it is the exact opposite of the way he behaves. I have (personally) contacted Jason before with ideas and technology / solutions (related projects he is himself affiliated with), he liked them very much and then said „good luck with that“ (in other words: „goodbye“). Although he pretends to value collaboration, my impression is that in truth he is very proprietary about his „own“ projects (yet to give him the benefit of the doubt: perhaps in this case it was simply related to one of his advertising relationships – though he also professes to only accept advertisers he himself „stands behind“, technologies which he is convinced are examples of excellent solutions).
There are other points that could be mentioned (for example what he says about his relationship with his father), but they are perhaps more controversial than clearly objectionable outright, beyond the shadow of a doubt. Much more important, I feel, is that Jason apparently completely neglects the importance of language and communication skills, how crucial these were for his own success, and how important they are for people starting out with more than zero strikes against them.
Here is my recommendation to these prisoners. Develop your language and communication skills – they are the most basic and fundamental information technology used by humans. One way to learn more about how important such skills are (or can be) is to read Malcolm X’s Autobiography.