 Am I crazy?
ismarc: I'd suggest going about the travel differently.  Using a car to get from point A to point B is insanely expensive compared to other methods.  Greyhound goes practically everywhere (just not on a convenient schedule/time frame for most people).  Also, starting off in Chicago, you've got a fairly major Amtrak hub nearby where you can reach nearly any point in the U.S. by train for a reasonable cost as well.I would set aside enough money to take Greyhound back to wherever you plan to call home afterwards (from the furthest point away, so you cannot get stranded), then plan out cost to ride Greyhound from place to place.  This should give you cheaper day to day costs, but puts you at the mercy of where you're going.This is where the blog/donate will help out.  Put at least a week's notice of what date you plan on being in which city, look for folks to interview and a spot to crash.  Ideally you'll be able to "tail" someone for a day or two to really see how their business goes while you're interviewing them.  This also would provide for a very interesting read (a day in the life of a entrepreneurs, and not just 1 famous guy, even just in the trenches never heard of them before entrepreneurs).  And along the way, share what you've learned with readers and subsequent interviewees.