Why some people are great at school, but only so-so at life

Years ago, I had the experience of meeting Donald Trump. I worked in city government in New York and he wanted to buy a building from the city. (He pitched poorly, and totally misread his civic nerd audience, telling us over and over how Britney Spears had a whole floor of rooms at his hotel….)

He did say one thing that’s stuck in my mind ever since:

“You know that person who did well in school and then never made much of himself? I’m not that guy.”

As an investor in startups, I often see the very qualities that made me and others standout successes in school turn out to be straitjackets. The setup of school might even be conforming us to something less than our best selves.

As I meet founder after founder, some of the reasons are becoming clear to me. I summarized the things that school asks that are wildly different from the things that life, and founder life in particular, ask.

The same attributes that in school are features, in life are bugs.

If you have to choose, be good at life — school lasts just a moment. Succeeding in school can make your no-risk path more attractive — just be sure to ask yourself if that’s what you want.