This is one of my fantasies, actually. I love the entertainment industry.
I would love to follow a....festival I guess? Band? Across the country and sell sandwiches outside. Mostly that would depend on who I end up dating next, I think. I wouldn't want to travel alone, but on the other hand with the right person it would be super fun.
My last girl would have been WAAAAAAAY into this as she loves festivals. It's her favorite thing in fact. We had broached the subject a couple of times, but she was not organized enough for us to really pull it off.
But I love the concept. People living adventurous lives, and making a buck in the process.
I also like cooking, so the Grateful Dead entrepreneur thing sounds fun because then you're combining cool people, cool music and making tasty sandwiches for hungry people. I can't think of a better way to spend my time!