Jake

I remember looking at my first iPod and being like: “This is a vessel that holds what I’m into.”

And also the early iPod didn’t have a lot of space, so you really had to curate what was on there in a way that people don’t do on their phones.

"If you are immune to boredom, there is literally nothing you cannot accomplish."

David Foster Wallace

"‘Well it so happens that you of all people know almost exactly what it’s like – to be a writer. You’re in your early-middle teens. The age when you come into a new level of self-awareness. Or a new level of self-communion. It’s as if you hear a voice, which is you but doesn’t sound like you. Not quite – it isn’t what you’ve been used to, it sounds... See more

What you don’t want to happen is unsustainable stress, or for people to not share failure or tell you when you’re wrong. So you need to actively fight this as the leader by: a) asking for dissent (“does everyone agree this is the right path? Does anyone disagree”? and letting a silence hang until someone speaks) b) reward debate.

Your job as a company leader isn’t to assume they’ll see it the way you do. Your job is to clearly tell the story