It would probably physically kill me to run for office, actually, heh. I wish I could do it. I hate that I'm a complete hypocrite on this, but my actual goal is to make career politicians obsolete, and that's not something a single person can do anyways.
But to answer your questions, you don't. You lose the first round. The first round is about becoming a credible threat as a nobody. You spend that first round, however, building up relationships: it's about no longer being a political nobody. Then you maintain those relationships for the next few years until it's time to campaign again, and then you leverage them into money and votes.
Besides, I don't actually want people like me in office. I'm a philosopher who doesn't like Plato; why would I endorse a philosopher king.
But to answer your questions, you don't. You lose the first round. The first round is about becoming a credible threat as a nobody. You spend that first round, however, building up relationships: it's about no longer being a political nobody. Then you maintain those relationships for the next few years until it's time to campaign again, and then you leverage them into money and votes.
Besides, I don't actually want people like me in office. I'm a philosopher who doesn't like Plato; why would I endorse a philosopher king.