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.

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

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

Everybody has been told already that they're too shy, too aggressive, too emotional, too reserved. They know what their fatal flaw is. They know the one thing to do to get better. But they just don't commit to changing because they feel a little bit in love with it, a little bit in love with the way they've been.

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.

I think the company that has the clearest set of values is Amazon. That company knows what it is. It may be that it's not your cup of tea, but every single person at that company knows what the Amazon values are.

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.

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.

Funny money has always been the reason housing prices have risen too fast. First, it was liar loans and negative-amortizing mortgages, where the total amount you owed increased rather than decreased every month. We all know how that ended, with the global financial crisis of 2008.

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.

When I was trying to write a novel, I ran out of money, and I was delivering packages on a bicycle. And I finally connected with these guys who started a software company, and almost serendipitously fell into that. I felt like they were goofy guys and that I was a goofy guy.

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

I am not excited about Bitcoin. I think it's an outrage that, in an era of global warming, there are racks of servers next to the Columbia River. I wish I could explain to the salmon that we've created a dam generating hydroelectric power so that we can generate a fake currency.

The really basic stuff that fuels 30-year job booms almost always comes from government research, stuff like biotech, the transistor, the Internet. The idea that private capital can handle the early spade work is a joke.

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.

I do think entrepreneurs need to be smart, but there's another scale I never evaluated myself on that is now the source of my deepest strength: Not how much brains I have, but how much love I have.

Most CEOs walk around the office like we own the place, without realizing that the place itself isn't worth owning: a business's value comes from the people who walk out the door every night, who have to decide each morning whether to walk back in. One of the simplest things you can do as a leader is honor their choice and appreciate their work.

You have to be sort of an emotional steward to really get a business to do something hard - to take people up the hill, to conquer the mountain, to sack the city. You have got to be a maniac.

Those in technology who can afford to stay in Silicon Valley all know it as one of the most beautiful places to live in the world, but a wariness has sunk in as folks from other walks of life are forced to leave: coffee shops are wall-to-wall with aspiring entrepreneurs, and restaurants buzz with talk of valuations and venture capital.

Short of a space-alien invasion or an Oklahoma tornado, there is almost no problem that a democracy can tackle in a year. But that isn't why we have a government. We have a government to solve the problems that greedy, short-sighted businessmen like me can't.

If we don't give the authors of music, film, literature, and journalism a way to control the distribution of their goods, the quality of all of these creative efforts will decline.

I think companies psych themselves out and say, 'Now that we're public, we've got to get all stuffy. We've got to be a certain way,' and the entrepreneurial spirit dies. What you got to keep alive is the intimacy, the energy, this crazed sense of purpose.

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

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

I'm an identical twin, and I felt that with my twin brother, we sort of formed this unassailable force, and it gave me the confidence to be different. Even if I was a goofball, my twin brother was a goofball with me, so I didn't have to worry about fitting in as much. I was able to march to my own drummer.

I think the corporate world is pretty starved for personality. The reason you have comic strips like 'Dilbert' and sitcoms like 'The Office' is that people just can't be genuine human beings in a corporate environment. So if you can really be your own self, even if it's a little bit different, I think people are really drawn to that.

At different points, I applied to graduate school. I got into medical school. I thought about being a writer. I thought about being an investment banker. I just didn't know what I wanted to do with myself. I think the thing that best suits me about being a C.E.O. is that you get to exercise many different talents and wear many different hats.

The tech industry's love for scrappy, accessible founders adds to the pressure. You're expected to lead by example, to roll up your sleeves, to know everything going on.

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.

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

If you actually believe in free speech and not simply the free distribution of other people's intellectual property, you should let journalists, law firms, and investors exercise their rights to it alongside your own.

So many tech companies have embraced a mission that they say is larger than profits. Once you wrap yourself up in a moral flag, you have to carry it to the top of other hills.

Most of the tech CEOs I know used to think that moving to the Midwest or the South was beneath us, a good tactic for the Boeings of the world who don't need the kind of rare skills we depend on, who have to grub for profits when we reach for growth. But if Amazon can't afford to keep growing in Seattle, who can?

What employing thousands of people in the middle of the country has taught me is how good and hard-working Americans in all cities are, and how much most of the country resents our wealthiest cities' sense of entitlement and condescension.

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

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

It's hard to improve our schools. It's hard to redistribute wealth created by the concentration of technological and financial power or to increase middle-class wages. But it might be easier to lower middle-class costs by building more housing.

Control of the browser that people use to access the Web turned out to be far less meaningful than the search engine we use as the starting point for finding Web information. I switch between Safari, Explorer, Firefox, and Chrome browsers all day. I never stray from Google search.

Even though I am sympathetic to newspapers, I am not entirely convinced by the newspapers' claim that Google News violates fair use standards in posting snippets from news articles on its site.

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.

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.

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.

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.

The problem for new businesses isn't corporate taxes. Anyone who has actually started a new business knows you don't make enough money for years to pay any meaningful tax on it.

When I was 28, running products for a company I'd co-founded, the CEO called to say that I had a problem with the board, that I probably couldn't overcome it, that I'd have to leave the company.

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

It's important for a CEO to feel lucky.

When my brother and I were 11, our father designed a 17-foot boat for sailing around the world. He'd never ventured more than a few miles from the U.S. He'd never sailed - or designed a boat before.

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

After a young adulthood trying to get him to see the world for how it really is, my brother Wes and I have come back to the way our dad is, realizing that it's sometimes our job to see the world as it could be, as we want it to be.