If you fail will you be happy with going back to your old life? Will you all of a sudden enjoy being in a "cage"? What happens if you're only happy when working on startups and every single one of them fails? Will you be poor forever? What if your current startup succeeds? Will you stick with it as it becomes a large company or leave and try to recreate the startup environment you enjoyed so much? (it seems to me that YC might be a way for PG to relive his startup days, which is why he tries to reproduce the Viaweb model so closely).
