Paul,
Great article, I found it extremely helpful and encouraging. I did have one question though around point # 9. Family to support. When you started Viaweb, did you have a family? If not, what about when you founded Y Combinator? The reason I ask is that I feel that having a family is a huge motivator for success, not a detractor. Now it is extremely risky especially if you are the sole provider for the family, but the reward is extremely high. If you have the confidence, determination and the right support (money, good business partners, etc.) your chances of success are increased. That would be like saying that it is not wise to be an extreme sports athlete or even a race car driver if you have a family because it is too risky. Calculated risks have great potential.