Unsolicited suggestion: What it's like to get rich
Everyone talks about how to do it, but most people are very reluctant to talk about what happens if you do. I think it would be very motivating, especially since you've been honest in saying that you started Viaweb with that as the primary goal.
It's considered unseemly to even talk about it (or ask you to talk about it!) in public. Right up your alley.
I've thought of writing that essay, but it's so dangerous that I'd want to spend a long time on it. (One of the surprises, in fact, is how dangerous it is to talk about.) Plus startup school wouldn't be the place.
