 Am I crazy?
SwellJoe: Yeah, you're a little crazy, but there's no better time than now to do crazy things.  It won't get easier, cheaper, less stressful, as you get older.  I think you're underestimating the expense of some aspects of this...but if you plan extremely well and live extremely cheap, you can probably live a couple months on the road for $1500.You should start blogging about your plans (your route, what you're taking with you, who you want to talk to, etc.) immediately...it won't bring in any revenue, but it will (hopefully) get you in touch with enough people willing to help along the way.  Video might also be helpful.  Once you're actually setting out, you might be able to get enough traffic to bring in some cash.  The blogging process is also good for other things...it makes you a better writer, and if you get some traffic it might catch the attention of a publisher or magazine editor.Also, you can crash at my place when you get to Silicon Valley, if you like.