It's still amazing to me how a 32 (then) year old high school dropout skateboarder from the south side of Chicago made a highly important CEO and a high priced lawyer look like complete bitches.

People who have been extruded through the public education and university system are often blind to their own bullshit in a way that someone who has found success outside of that system is not. Tim also has quite a bit of experience in social engineering and adjacent skills that allow him to spot when others are pulling the same tricks.