039: Dick Costolo | Twitter CEO says Business is like a Forest Fire

Dick Costolo, CEO of Twitter, is an extreme example of the high school reunion paradox. We all have seen it. Homecoming kings and queens who have sunk into mediocrity while awkward "nobodies" have somehow made it big. Costello, the one who was always picked last for the team, is now CEO of Twitter. He describes how he used his perpetual outsider status to scrap his way to the top. His strategy is surprisingly simple; it's only the execution that's difficult.


1. With enough perseverance even the most unlikely to succeed may find themselves on top.
2. Simply being willing to put yourself in uncomfortable situations is the best way to build resilience.
3. Success in business is like forestry management: you may be surrounded by wildfires, but the key is to identify and extinguish the most urgent ones first.