“Worse is Better” and here’s why:
One of the key characteristics of the mainstream customer is conservatism. Such a customer does not want to take risks; he (let’s say) doesn’t want to debug your product; he doesn’t want to hit a home run so he can move up the corporate ladder. Rather, he wants known, predictable improvement over what he is doing today with his own practices and products. He wants to talk to other folks like himself and hear a good story. He doesn’t want to hear how someone bet it all and won; he wants to hear how someone bought the product expecting 10% improve- ment and got 11%. This customer is not interested in standing out from the crowd, particularly because of a terrible error in his organization based on a bad buying decision. These aren’t the characteristics of someone who would love technology and build an extravagant product based on it; therefore, it is hard for a technologist to understand what this customer values.
I think this is one of the primary reasons that Dave Winer‘s software and company continues to be successful despite his critics. He fully grasps this: people don’t want the best, they want something better than what they have. Dave is criticized constantly for not doing the “right thing”, but he knows that the right thing isn’t as good as “bootstrapping“, as he calls it.