Highlights

Favorite questions and quotes from the conversation.

How do you pick what is important to work on?

I think you want to look for the intersection of what you're good at, what you enjoy and where you can create value for the world. In my experience, if you don't find something at the intersection of those three, it's hard to really have an impact. I think most people kind of just fall into what they work on. They don't give it much thought and there is benefit to that. Sometimes you actually have to just try stuff to figure out what you like. But I really do think it is worth up-front thought about what you're going to spend most of your waking time doing.

How do you advise people to select who to work on things with?

Finding your tribe, finding the sort of people that you end up working with on and off for the rest of your career is really hard. I don't have the perfect answer to this yet, but I think one thing is you should be willing to move. For whatever you're doing, there tend to be pockets of it around the world where there are similar people that are doing great work in whatever field you care about and it's really worth trying to go be near them. Another thing that I have learned is that whenever I've helped people for no immediate benefit and with no intention of ever getting a benefit at all, time and time again in my career, it has really later benefited me a lot. I think just trying to help a lot of people and out of that seeing, who is really impressive and who gets things done is helpful.

Once you've found your tribe, what are the best ways to accomplish big things?

There's a Charlie Rose quote on this that I've always loved and I've since added one more element to it, but the quote is that, "The way things get done in the world are through a combination of focus and personal connection." And the additional point I would make, after having thought about it for a while, is that the third factor is self-belief. You really have to have a deep-seated personal conviction that this thing you're going to do, that a lot of people say is really stupid, is going to work and going to be important. I think those three things, focus, personal connections, and self-belief, in my experience are how things get done in the world.

What advice do you have around work-life balance for people in their twenties?

Compound interest is a good metaphor here. If you work really hard at the beginning of your career and you get a little bit better at what you do every day, every week, every year, and you've learned more and you meet more people and you just get more done, there's a compound effect. And it's far better to put that time in at the beginning of your career than at the end because if you do it at the beginning, you get to benefit from it for the rest of the time you work. Obviously you don't want to work all the time because your twenties are your twenties, but I do think you want to work harder than most people think you should and I think that if you do that, you tend to benefit from it later.

How do you make the distinction between working on something for too long? When is it time to call it quits vs being on the cusp of a breakthrough?

Yeah, this is really hard. Knowing when to quit and knowing when to give up on something- there's no perfect answer to that. It's really challenging to even get that approximately correct. I think most people give up on things way too early. The mistake that most people make is they try something, it doesn't immediately work and so they immediately give up. These things are really hard. They take a very long time. There are a lot of critics. It should be an internal, not an external decision. It's basically when you have run out of ideas and something is not working, then it's a good time to stop.

What is the right motivation? What should people look for to be inspired to keep going with their ideas?

If you don't believe what you're doing is really important, if you don't derive satisfaction from what you're doing, then you will not be able to sustain. The only motivation that I have seen work for people over a long period of time is enjoyment in what they're doing and an intense belief that it matters and ideally liking the people that they go to work with every day.

By the way, it's totally cool when people start off saying, "Well, I want to make money," or, "I want to be famous." I think a lot of people start that way and they don't like to admit it. But pretty quickly or at least in the first few years, I think a lot of people find a deeper mission.

Have you noticed a change in what motivates you over the last 10 years?

At this point, I am only interested in things that I find sort of interesting and important. Early on, like a lot of other people, I think I was like, "Well, I want to make money. I want to be in the press," or whatever else. I wouldn't say that doesn't motivate me at all, but it's honestly not a big factor at this point. There's a set of things that I think are important and I wanna work on those.

I think another point about motivation that people don't talk about enough is related to burnout. So I was told and I thought for a long time that you get burned out from working too hard. In my own experience, what I found is that burnout actually comes from failing and things not working. Momentum is really energizing. The lack of momentum is super draining.

A lot of founders try something and fail and assume that they just can't work hard enough or don't have enough energy or passion and that's actually not true. It's just that that thing didn't work and what you should do is shut that company down, go on vacation and try again. When you look at really successful people and say, "How do they get all those things done," they have the benefit of momentum and momentum is energizing. The lack of momentum is really not energizing.

What is your advice on how to approach taking risks?

I think people have terrible risk calculus in general. Especially early in your career. Being young and unknown and poor, that is actually a great gift in terms of the amount of risk you can take and I think people don't capitalize on that enough. What risk actually looks like is not doing something that you will then spend the rest of your life regretting. If you really believe in something and there's an idea that you're super passionate about and you take a calculated risk to start a company, realizing you may forgo a couple of years of steady income, another job, and whatever else, that's a great risk to take. If you don't take that risk, I think you have a very high chance that you'll end up regretting that. I think one really important thing to strive for in your career is to be a doer, not a talker. Take the risk of committing to what you have conviction on.

What's one piece of advice you wish you had gotten early in your career?

Ask for what you want. You will get told no a lot, but sometimes it will work. Being willing to ask for what you want and be somewhat aggressive are really important characteristics of being an entrepreneur. Another thing that I learned is that each crisis gets less scary than the one before it.

How much do you think people should have strong opinions versus iterating and finding out what works?

I think you want a combination of those two things. You want to have a strong opinion and then be flexible about the details. The thing I don't think works often are the startups on their 11th pivot that are totally unrelated, but I put a big difference between refinement and pivoting. I think strong opinions about the future are really important and I think one of the things that I have noticed among the most interesting, the most successful people that I spend time with, is that they have strong opinions strongly held about the future. They are willing to be convinced with new data that they are wrong, but the bar for that is fairly high. This idea that the future is fundamentally unknowable, I've never liked.It's good to have strong ideas about the future. And it is okay to not be super diversified in your investment portfolio or your career or your life.