Drew Houston

Often smart people have more trouble learning than otherwise because the more book smart you are, the more not knowing something or being wrong, it's not just not knowing something or being wrong, it's like an assault on your identity.

Both your strengths and your weaknesses are massively amplified and a lot of blind spots in your personality can become huge cultural dysfunctions in the company.

You have to figure out how to keep your personal growth curve ahead of the company's growth curve.

Always be working back from, in one year from now, what will I wish I had been learning today? Two years, five years?

Most of the time CEOs want options. They want to hedge their bets, but what you really want to do in these strategic inflection points is go all in one thing.

I'm working really hard. I'm in meetings all day, emails all night. Is this it? I'm very busy, but I'm not really productive. I'm not putting in a lot of creative input.

My playbook as an entrepreneur is to get really frustrated by something, and then try to solve that personally.