Recently, Rodney Mullen's skate + tech TED talk has been criticized by Kathy Sierra as sexist. Both Mullen and Sierra seem to be arguing the same point, just from different perspectives.
They both started skating back during its first wave of popularity. After skating imploded though, the mix of people changed as some of the people that started arriving on the scene were there precisely because it wasn't popular.
Because skating was on life-support, few (if any) kids in your school skated. No one was organizing competitions. So you read magazines and watched videos to learn tricks. Then you tried to land those tricks until a security guard chased you away, or you negotiated some kind of a truce to allow you to skate.
What kind of kid puts up with being harrassed in school for being a skater, and then after school getting hassled by cops and other authority figures?
You could point to the positive side of this, the perseverence. However, that overlooks the negative, that these were kids who had opted or failed out of mainstream society. Kids already besieged and for whom skating looked perfect -- adults as the Enemy, no kids from school, no competitions.
Anti-social kids like these do not make for a well-behaved and welcoming culture. People looking for group approval and more social gatherings just aren't going to have much fun.
That however is one of the great things about both skating and hacking. The "social" side of it can be dialled down to practically zero, and you can get into a state of flow that doesn't depend on anything but you.
It's these individual benefits that Mullen lauds, while Sierra sees the flip side's social costs. Of these two sides, the one that matters most is the one you choose.