Hmm, not sure Airbnb was the best example to start off with to support that YC has contrarian thinking. PG thought Airbnb was a stupid idea, and only agreed to invest on them on a whim. It was a Black Swan event how Airbnb ended up at YC through Michael Seibel. Tutorspree makes sense, I don't see it as crazy in the same way that Airbnb was. Same goes for Flightcar, but great startup idea. YC is generally investing in growth/traction at this stage and not crazy ideas or founders. PG alluded to this in Farming for Black Swans. I believe they were looking for certain types of founders in 2008-2009, but that has changed. Not fully convinced that YC is driven by contrarian thinking today.