Startups can be the most conservative organizations in the world. We spend so much energy nurturing our delicate egos against naysayers and self-doubt that we can hardly admit mistakes. This is especially true of first-time CEOs.

When I was still settling into being a CEO, I wasted a lot of time driving initiatives designed to please others, acting as if someone wouldn't let me do what I wanted to do with Redfin.

I often think about what my replacement will do after I'm fired. She won't have emotional commitments to decisions that I already regret.

Glenn Kelman Quotes