This was the part of the article that resonated the most with me. I wonder if this is the mechanism by which startups end up as big companies with totally useless IT departments - the people who built the stuff become identified as pessimists, and get starved for resources, good people leave, end up in a vicious cycle.
Great post.
It must take a lot of personal strength to put your failures out there for others to learn from. Thank you.
It's very, very difficult to wear both the developer and the evangelist hats at the same time: being a developer requires that you be very pessimistic, so you can see and fix all the problems in your design, while being an evangelist requires that you be very optimistic, so others can feed off your passion.
pg has mentioned many times that a startup is very difficult for a single founder. If I remember correctly, he says that because it's too much work for one person.
This is a slightly different angle that I had never really thought about. In effect, you'd have to be "Sybil" with multiple personality disorder to pull it off.
I tend to think of myself as a "very optimistic developer". I doubt I'd even try what I'm doing if I wasn't. Does this mean I may miss major design defects because of my rose colored glasses?