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.

Startups alternate between nostalgia for the garage and millennial longing for a lucrative exit. But what I always keep in mind is how disconnected and purposeless I felt before Redfin or my earlier startup, Plumtree. All I ever wanted was to get into a situation where I could win. Everybody has that dream.

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.

Glenn Kelman Quotes