I like Craig on some level. I think most people in the tech world like him, but he’s delusional, reckless, and created one hell of a cockroach of a business. He’s hypocritical (On the board of the Sunlight Foundation and advisor to Wikimedia but users can’t use CL data to create cool things) and on some level he lacks self-awareness. He’s no different than a capitalist who milks his business for profits instead of innovating. He’s smart enough to hide behind an “aw shucks, golly gee, I didn’t know I was making so much money” personality. The truth is this is the same personality as the guys who missed the boat on innovation at their newspaper business for the last 20 years.
Craigslist is one of the most weirdly frustrating web sites on the Internet: there are so many ways it could be improved, from simple design tweaks to reconciling its business practices with its professed principles. But CL is never going to substantially improve as long as C is still in charge of it. And while building a better competitor would be relatively simple, overcoming CL’s massive network effect? Not so simple.