One of my favorite anti-portfolio is the one from bessemer: <a href="http://www.bvp.com/portfolio/antiportfolio" rel="nofollow">http://www.bvp.com/portfolio/antiportfolio</a><p>I remember when I advised my friends to work for Google in 2002 and people were looking at me like I wanted something bad for their career. It's always easy to dismiss opportunities that are one of a kind... even YC, with more data than anybody, makes "hiring mistakes".
I agree with the premise. But were they really not fundable? :-) I believe investors were running after them (funny thing is 5 of them had Sequoia as institutional investor, in fact first VC for 4). Also all of them worked like a charm. In fact, when you used Google and YouTube for first time I bet your reaction must be "wow, this just works". At least, that's how I felt.