How Contrarians Think: The Early Days of Square, Yelp, & PayPal with Keith Rabois

When I make a new investment, I really want half of VCs to think I'm crazy and laugh at the investment. I don't want 100% to laugh necessarily because then I might actually be missing something ... But if none of them are laughing or 20%, then I'm probably not taking enough risk, and it's probably not a differentiated investment.

The really great founders don't ask you 'Should I do A or B?' ... What they actually say to you—and this is almost verbatim—will be 'What's the best conceptual way to approach this problem? Can you give me a framework for deciding between A and B?'

To be an investor, one has to, by definition, see things that others don't see and appreciate them before other people do.

The more stress you have in your life, the better—the healthier you are, the wealthier you are, the happier you are.

Jeff Bezos has a great quote about this: 'It's easy to be contrarian. It's extremely rare & difficult to be contrarian and right.'