This book was okay. It has an interesting premise and a good sense of humor, but the narrative is a bit lack-luster. Shepard seems to leave out a lot details and stories that would have put more of a mark on his experience and make it seem more meaningful to him. His concluding chapter about solutions seemed out of place. I would have preferred a concluding chapter that incorporated more self-reflection.
As far as the project itself, I didn't find fault with Shepard's whiteness, youth, health, lack of responsibilities, etc. that others have. I did think it was interesting how easily (it seemed) he ditched his pride to milk the system. I was actually surprised and a little disappointed in how the book focuses a lot on the various social services available to help him eat, get a job, and find a dump to live in, and less on truly building something - like a company, career, or family - from 'scratch.'