Tony Xu is co-founder and CEO of DoorDash, an on-demand delivery service operating in more than 1000 cities across the U.S. The child of two immigrants who juggled graduate school and full-time jobs, he learned early on how to make his own decisions—including selecting an American name for himself, at the age of five, inspired by the lead character in his favorite TV show, “Who’s the Boss?”

What is something you’ve learned that you lean on daily?

Don’t let what you say get in the way of what you want to accomplish. Our general counsel, Keith Yandell, gave me that advice. I like to move quickly, and I haven’t always prioritized clear, well-thought-out communication. When it was just three of us in a garage, it didn’t matter as much. But in year five of DoorDash, it’s critically important that I’m intentional about what I say and how.

People tend to prepare for big, high-pressure interactions like negotiations, but I think it’s actually more important to prepare for the small, everyday conversations. That’s where most of the work gets done. I write down my objectives ahead of time, and I try to share them with the other person. I also think in advance about their objectives. Once I understand all that, I’m much better equipped to communicate in a way that delivers the outcome I want.

What one piece of advice would you give someone starting a company?

Start small. Especially in the beginning, a company should feel like a project, not a grand vision. Write down the specific risks or problems you need to overcome to reach the first set of customers who will love you. Then focus on those, and don’t worry about anything else—not your long-term product vision, not how much money you’ve raised. When we started DoorDash, we had three questions: “Would customers be willing to pay $5 for this service?” “Would restaurants be willing to pay us a certain percentage?” “Would drivers be willing to work for this wage?” It was a pretty simple business plan, but those were the answers we needed in order to know whether we had something.

I think it’s also important to start with the hardest problem. For us, it was that first question—the customers—which is why our first big expansion was to east San Jose. We’d been successful in Palo Alto and Mountain View, and people wondered why we didn’t go to San Francisco or west Los Angeles next. But we needed to know whether this could be a mainstream product in terms of price point, and moving into a market similar to Mountain View wouldn’t have answered that question.

What small change has made a big difference in your life?

I’m not doing this consistently quite yet, but I’ve started putting my phone in another room at night. I sleep better, and if I do wake up, it definitely minimizes the temptation to check in on work. It’s a good hack.

The other change, which I am consistent with no matter where I am, is running. I run in the mornings two or three times during the week, and both days on the weekend. I’ll usually go to the Marin Headlands or somewhere in nature. It helps me regulate my mind and body, which I think is why the habit stuck. I feel noticeably better when I run.

What don't you know that you wish you knew?

Lots of things! I wish I knew more about certain technologies, or how to be a better listener. In general, though, I’ve come to realize that the more I do something, the less I seem to know about it, and I think that’s a good thing. Old intuitions die hard, but they do need to die. The world changes, and you have to update your ideas.

When I want to learn more about something, I try to do two things at once. I think it’s important to have a point of view, but at the same time, I try to keep a beginner’s mind and pretend I know nothing. Then I’ll see if I can hold the counterpoint in my head as aggressively as I held my original view. Sometimes, the counterpoint wins, and I update my beliefs.

What books are on your nightstand right now?

There are quite a few. I have a bad habit of buying more books than I can read, and I’m a pretty slow reader—my wife literally laps me every week. Right now I have Scale, which is about why cities typically outlast companies; Antifragile, which is about how strength can come from uncertainty; and The Elephant in the Brain, which is about what motivates people.

I just finished John Doerr’s book Measure What Matters, about objectives and key results, and a couple of months ago I read Play Bigger. The thesis is that you should create your own category and write your own story, rather than letting your customers or competitors write it for you. I’ve always believed in that approach, so it was partly confirmation bias, but I liked digging into the examples.

I also recently read The Outsiders, by William Thorndike. It’s about eight CEOs, Warren Buffet and seven other people most of us have never heard of, and how they far outperformed even the biggest tech companies. There are a few things they have in common: for example, they all did a lot of share buybacks whenever their companies were undervalued. They essentially doubled down and bet on themselves, which goes against the conventional wisdom.

When did you realize you were wrong about something?

I’m wrong all the time. I try to get the big things right, like strategy decisions and the people we hire, though sometimes I’m wrong about those, too. But I’m more than happy to be wrong about the small things, like my point of view on a product or a function. Frankly, I think I should be wrong about that stuff pretty often, because part of growth is changing your point of view. If I were always right, I’d be worried I’m missing something or not taking enough risk.

To get more comfortable being wrong, we start every team discussion at DoorDash with highlights and lowlights—and the lowlights come first. We want to make sure whatever didn’t go well doesn’t just get swept under the rug, because most of the time, looking at what’s wrong is actually the easiest way to find the right answer.

What unit of time matters the most and why?

For DoorDash, I think it’s a year. A company is the sum of so many teams and projects, some of which depend on each other, which means moving the needle on even a few metrics can take longer than you’d think. I also think the unit of time changes as the company grows. If you’re creating a category, for example, that will take far longer, but a year is reasonable for us right now.

For most teams and individuals, I think it’s a week, because that period of time is so closely tied to our sense of success and happiness. Most of the important things I want to get done take more than a day. If I can do three in a week, that brings me joy. I usually know what those three things are every week, and I have a little ritual every weekend that keeps me honest. I look at the week ahead, but I also look back to see whether I spent at least half of my time focused on those important things. If not, I know I need to shift my focus.

Hard-won advice