Craigslist made him millions (yes, yes, we all know the story about how he wants to keep CL intentionally small, spurning potential hundreds of millions in profits - but still, he's a millionaire). Part of his money-making strategy is charging prostitutes to post sex ads.
So he can use "I'm a socially inept geek" excuse as long as he wants, I think it's only fair that he is asked some tough questions about it.