Is there a point to school? 
eplanit: The way you describe your situation and outlook, I'm wondering whether you're pursuing a career, or a lifestyle.  I fear it's a lifestyle.  That is, what exactly do you mean by "interested in hacking and the start-up culture"?  Hacking is about application of talent and curiosity; start-ups are about running a business (entrepreneurship, capitalism).   Hacking, absent any purpose or discipline, is really just a hobby.  Entrepreneurship, itself, isn't a "culture".  It involves cleverness, creativity, pervasive optimism, and a lot of perseverance.Your analysis is telling: "it seems that school is something one goes through to get a job and make money".  And then you go on, "but to be successful...".  I'd stop there - how do you define success?  If it's being happy at work everyday, then I'd say you're seeking a 'job', a 'vocation'...you should seek to be a skilled tradesman.