VCs are good at asking questions.

It's important for a CEO to feel lucky.

I wish I was as annotative as Elon Musk.

I learned to value speed in everything I do.

Almost everything is interesting if you work at it.

People can smell a lack of respect from a mile away.

I wanted to solve every real estate problem with software.

I just don't like bullies. Especially hypocritical bullies.

If your values don't alienate anyone, it is just platitude.

The U.S. is one of the hardest-working cultures in the world.

We need a government policy all-out in favor of more, denser housing.

Sometimes I wish I was less of a maniac; sometimes I wish I was more.

I worry all the time that we're going to screw up a customer's offer.

When you start a company, you become really emotionally involved in it.

I learned that people love to be good at things, even the silliest things.

I wish I was as smart as Jeff Bezos. He's just a large-brained space alien.

Folks are leaving Silicon Valley, mostly because they can't afford to stay.

The one thing that Redfin has been really good at has been at delighting people.

My advice for men who aren't yet parents is to make sure you're a happy person before having a baby.

Steve Jobs knows how to hold his hand out, to build beautiful products and make people pay for them.

The most important question venture capitalists ask is what prevents your company from growing faster.

I learned, even when all hell is breaking loose, first to take time to make my environment productive.

People knew about IBM before they knew about Apple. Sometimes it takes a little longer for better to win.

I think if I had gone to a private school and been coddled a little bit, I wouldn't be as tough as I am now.

Once you become more like Madison Avenue, you become acutely sensitive to what's going to annoy your clients.

Growing up is mostly the process of having to acknowledge the differences between your world and the whole world.

If you build a better mousetrap, regardless of your marketing budget, the world will beat its own path to your door.

Every firing happens differently except in this one respect: the person being fired can't believe how fast it happens.

We don't need to take the world by storm. We just need to make our customers happy, and when we do that, the word spreads.

Slow investing can have the same impact on startups that slow food has had on cuisine: good things come to those who wait.

Employers are as sensitive to housing costs as their employees, which is why, when we build more houses, we create more jobs.

From squalls, jibes, and other sudden calamities, I learned you don't always get to decide when you've got to make a decision.

Behind the driven person is just an enormous amount of misery. You have to be miserable with the status quo to want to change it.

Any educated person recognizes that curiosity and creativity aren't just important; they are among the essential human activities.

As a captain of industry, I would prefer more tax breaks to help people buy houses, but as a citizen, I realize someone has to pay.

Over the years, I just started paying a lot more attention not to whether I was right or wrong, but just to how I make people feel.

I learned that it's important to treat yourself like a work in progress, to think about how you can improve, to listen to feedback.

To build a great business, you have to do something hard just to be able to withstand all the competition that will later come your way.

With Facebook's IPO, the world learned a new way of organizing businesses around one overriding imperative: to ship new products quickly.

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.

I think that real estate consumers are stuffy; I think they're scared. They don't buy a house every day. It's a very infrequent purchase.

I learned that sometimes you should just tell people the ugliest things about you because those are the things that people trust the most.

One reason I was so convinced that Redfin would work was that I never met anyone who bought or sold a home who thought the process was ideal.

You wanna work on something big so that if you win, everybody wins, and you really have an impact on the world. And that can get you out of bed.

In some ways, it's better to be undervalued a little than overvalued a lot, just because it's still easy to believe our best days are ahead of us.

What's most revolutionary about Uber is not the tool that consumers use but the fact that the only equipment needed by its drivers is their iPhone.

When we talk about a city's cost of living, we don't mean food, transportation, or clothing, which cost about the same everywhere. We mean housing.

If somebody were more passionate about Redfin, how would she not be more qualified to have my job than I am? Like, that's the thing I have to be the best at.

We need to create technologies - and a culture of respect, and an updated legal doctrine, too - that allow creative folks to make money from their own efforts.

The truth is that I love working. I love my kids. But I don't view one as evil and the other as good. I need to work to be a happy person, to be a good parent.

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