Recently a founder whom I respect, Michael of Reputation.com, was speaking to a group of investors and said something that struck a chord with me:
Most founders have an anti-authoritarian view while most investors don’t.
I definitely identify with founders on this, and recently wrote about being a cypherpunk back in High school. The hacker scene I grew up in was distinctly subversive & anarchic. I believe that is why I love founders who fly in the face of convention to try to disrupt incumbents and change the world. If I can be personal for a moment and tell you a personal shame of mine: when I went to business school I bought new clothes in an effort to fit in. Recently I’ve come to see this as a mistake. To be our best we shouldn’t strive to fit in but to stand out. So if you’re on your way in to pitch me wear whatever you would to the office, I just want your best ideas. In exchange, please don’t be surprised if I am wearing this t-shirt: