The difference between an organization of 5 people and an organization of 10 people—or one between 10 and 20—it's not twice as hard; it's far more than twice as hard. And the amount of coordination overhead that it requires when you double your head count is, again, not double; it is far more than that.

That same myopia that we, at times, celebrate in entrepreneurs—they're laser-focused... You know what? A lot of times, you don't need a fucking laser focus; you need a broad perspective. And if you can't change and switch between those two at regular intervals, it's really a weakness.

Meetings are great for getting a group of 2-4 well-informed people on the same page.

It's never been easier to start a new software company than it is today without raising money.

I think the problem with the word 'accountability' is that it's often total bullshit. Accountability is only meaningful, in my opinion, when it's tied to an individual's own declaration of work. You can't have meaningful accountability if you're telling someone how much work to do and in which time to do it—then you're just a slave driver.

The mission statement, if it is to have any effect at all, is a way of weighing trade-offs between two things that you want and then deciding which of the two you want more. If it's not providing that function, if it's not putting a hand on the scale in those weighings, it's useless.

Money is nice and [it allows you to] buy a bunch of nice fine things, but it is not the primary source of happiness for someone who's cleared a baseline bar.

I think far too many tech entrepreneurs are obsessed with disruption. You know what? A little less disruption and a little more fixing.

If you look at what motivates people at work, it's things like autonomy, mastery, and purpose.