Note: While reading a book whenever I come across something interesting, I highlight it on my Kindle. Later I turn those highlights into a blogpost. It is not a complete summary of the book. These are my notes which I intend to go back to later. Let’s start!

  • A little investigating told me that there was one sport my high school did not offer at the time: lacrosse. If none of the other kids had any experience playing lacrosse, then everyone would feel as confused as I did. It would be a level playing field. So I asked the school administration whether, if I found a coach and enough boys, we could start a lacrosse team. The answer was yes. So that’s what I did. After all that apparent ineptitude, I emerged as a decent lacrosse player, I was elected captain, and we were a pretty good team (though I still preferred the company of the nerds to the athletes). The determination that led me to create a new sports team taught me an important lesson: opportunity is manufactured.

  • I’m not advocating dropping out. I could have entered college with more focus in the first place, or I could have tried to change my experience when I got there. But taking a job that I’d won through my initiative was another way of controlling my destiny. This, as I see it, was an example of manufacturing my own opportunities. This is why starting a lacrosse team, producing a play, launching your own company, or actively building the company you work for is all more creatively fulfilling and potentially lucrative than simply doing what is expected of you. Believing in yourself, the genius you, means you have confidence in your ideas before they even exist. In order to have a vision for a business, or for your own potential, you must allocate space for that vision. I want to play on a sports team. I didn’t make it on a team. How can I reconcile these truths? I don’t like my job, but I love this one tiny piece of it, so how can I do that instead? Real opportunities in the world aren’t listed on job boards, and they don’t pop up in your in-box with the subject line: Great Opportunity Could Be Yours. Inventing your dream is the first and biggest step toward making it come true. Once you realize this simple truth, a whole new world of possibilities opens up in front of you.That modus operandi is what brought me to Google in 2003.

  • Creativity is a renewable resource. Challenge yourself every day. Be as creative as you like, as often as you want, because you can never run out. Experience and curiosity drive us to make unexpected, offbeat connections. It is these nonlinear steps that often lead to the greatest work.

  • Neither Ev nor I, nor (I suspect) several other members of our team, were actually interested in podcasts. We ourselves didn’t listen to them. We didn’t record our own. The truth is that good audio requires good production. Listening to Terry Gross is great, but listening to some dude in his basement drone on about XML for an hour with a low-quality mike and no sound production is pretty arduous. We lacked something that is the key to a successful startup, and it was bigger than sound quality. It was emotional investment. If you don’t love what you’re building, if you’re not an avid user yourself, then you will most likely fail even if you’re doing everything else right.

  • So often people follow a career path without thinking about what really inspires them. How many people graduate college, see that lawyers and doctors get paid a lot, and follow that route, only to discover that they hate it? I think about the comic Demetri Martin, who often appears on The Daily Show. He went to law school at NYU, but instead of being a lawyer, he ended up a quirky comedian who plays the ukulele and uses puppets in his act.

  • Adopting a career because it’s lucrative, or because your parents want you to, or because it falls into your lap, can sometimes work out, but often, after you settle in, it starts to feel wrong. It’s like someone else punched the GPS coordinates into your phone. You’re locked onto your course, but you don’t even know where you’re going. When the route doesn’t feel right, when your autopilot is leading you astray, then you must question your destination. Hey! Who put “law degree” in my phone? Zoom out, take a high-altitude view of what’s going on in your life, and start thinking about where you really want to go. See the whole geography—the roads, the traffic, the destination. Do you like where you are? Do you like the end point? Is changing things a matter of replotting your final destination, or are you on the wrong map altogether? A GPS is an awesome tool, but if you aren’t the one inputting the data, you can’t rely on it to guide you. The world is a big place, and you can’t approach it as if it’s been preprogrammed. Give yourself the chance to change the route in search of emotional engagement.

  • If you don’t wake up excited for the day ahead, and you think you’re on the wrong path, how do you find your way? I always tell people to back into it. Imagine working on something you love. Describe it to yourself. Don’t focus on how much money you want. Instead, think about this: What type of people surround you? What sort of work are they doing? How do you get to work? What adjectives would people use to describe what you do?

  • Maybe your ideal situation is to be in a funky office space near the ocean. There are bikes hung on the wall right outside so you can go for a ride in the middle of the day. Maybe there are even office surf boards. People are laughing. Maybe, describing your fantasy, you say, “We have a lot of fun during the day, but sometimes we work really hard.” What job is like that? Maybe you should consider working at a small ad agency. The place sounds like a creative shop of some kind.

  • Once true passion hits you, you can recognize all the times in your life when you were chasing the wrong dream. And after you’ve experienced that sustained fulfillment, you’ll never want to settle for anything less.

  • Gattaca is a sci-fi movie about a somewhat dystopian future in which reproductive technology is used by those who can afford it to breed genetically ideal people. Vincent (Ethan Hawke) and Anton (Loren Dean) are brothers, but Vincent was conceived without being selected for superior genetics, while Anton is genetically ideal. Throughout their lives, Anton is better than Vincent at just about everything. A bunch of crazy stuff happens in the movie, but the point is that there’s a scene where Vincent challenges Anton to a swim race, a version of “chicken” that they used to play when they were boys. They swim straight out to sea—really far out. The first to give up and turn back to shore loses. Vincent wins. Anton asks Vincent how he beat him. After all, Anton is far stronger and genetically superior. Vincent explains that he gave every ounce of his strength swimming out to sea. He saved nothing for the return trip. This is a revelation for Anton. He is stronger, but he was conservative. He held back instead of giving his all. Vincent, on the other hand, was willing to risk drowning in order to win. There is a wonderful lesson to be learned from Vincent’s decision. In order to succeed spectacularly, you must be ready to fail spectacularly. In other words, you must be willing to die to achieve your goals. Figuratively, of course. What I’m suggesting is that you embrace the upside of fantastic, epic, earth-shattering, life-changing failure. It’s totally worth it if you succeed. And if you fail, you’ve got a great story to tell—and some experience that gives you a serious edge the next time you go for it. This is a good lesson for startups in general, and for otherwise going for what you truly want. It’s like there’s a natural force of equality at play. If you really want to succeed big, you have to be willing to risk crazy failure.

  • It’s been widely reported that 90 percent of tech startups fail. Every entrepreneur in any sector is a risk taker. Even some of the most widely known successes had periods of ambiguity or near failure. For example, Pixar began as part of the computer division of Lucasfilm, developing graphics and animation technologies. It hadn’t found its footing when Lucas needed money for his divorce and decided to unload it. He sold it to Steve Jobs for $5 million. The animators at Pixar had for a long time wanted to do computer-animated movies, but the costs of making a computer-animated film were too high. Jobs believed in their dream. Twenty years later, Jobs sold Pixar for $7.4 billion.

  • People were constantly telling us that the whole concept of Twitter was dumb. Even some of our own engineers had their doubts. On top of that, the service was breaking all the time. This did not feel good. I had helped create Twitter, I was working on it every day, and when it failed, I felt as if I’d done something bad. As if I’d neglected a responsibility. Whenever the app was broken, I was frustrated and on edge until it was fixed. But lots of times, we didn’t know what had gone wrong and it took hours to get ourselves back up and running. One day, all this stuff caught up with me. Maybe I’d also had a bad commute. Anyway, this time when the service went down, it was the straw that broke the camel’s back. I stood up in the middle of our grim South Park office and blurted out something like “This is bullshit. Why can’t we get our acts together?” Jack Dorsey, who was CEO at the time, heard my outburst. He said, “Hey, Biz, will you take a walk with me?” We walked around South Park, and Jack said, “I need you always to be the guy that has the positive attitude and keeps people feeling like we’re on the right track, we’re doing good work, and we’re happy.” That was the moment when I realized that the company’s spirit was one of my key responsibilities. I had often had my own internal struggles, as we all do, worrying that I wasn’t helping enough or doing enough work. In the beginning, I was doing all the user interface and design work myself, but by the time of my outburst, we had hired people to handle some of that. I wasn’t coding all day long like an engineer. And I wasn’t the CEO. Was I pulling my own weight? Were the things I was doing important? I was giving a voice to the service, I was building a brand, but there was no way to quantify the results of my work. When Jack told me that he needed me to keep up the company’s spirits, I realized that my positivity, though hard to measure, was important. I wasn’t just creating a brand for the outside world; I was responsible for the company culture. We hit much lower points with much bigger stakes after that, but never again would I snap as I did that day. I was always able to find the bright spot.

  • There’s no such thing as a good deal in which one party gets the short end of the stick. Deals are like relationships. We want deals that are going to last. I’m not just talking about acquiring another company. I’m talking about partnering with another company, or divvying up tasks within your group, or getting married. Think of the toll that derivatives took on this country in the mortgage crisis. Derivatives are a zero-sum game—when one party wins, the other loses. There’s no net benefit. It’s win-lose. This is of course oversimplifying, but generally markets rely on gains and losses. However, in a business deal, if the terms aren’t mutually beneficial, a short-term win will turn into a long-term loss. You lose that company’s faith in you and its willingness to do another deal. You lose your colleagues’ willingness to stay late and help you out on a deadline. To some extent, in every deal your reputation and your business are at stake. Think of it like scuba diving. There has to be equal pressure inside and outside your body, or your lungs and eardrums will start exploding. Full disclosure: I’ve never scuba dived—but trust me on this, imbalance is bad. Kevin Thau, a colleague at my current company, Jelly, used to run all things mobile for Twitter. While there, he did all the deals with the carriers. He recently got a message from someone who runs a major mobile carrier in the United Kingdom. It said, “I don’t know what Jelly is, but if you want us to pre-install it on our new phones, call me.” Nobody gets that kind of thing unless they have a history of doing fantastic deals together. Another example of this would come later, when I left Twitter and started Jelly. Two of the people who helped me develop the idea left their company to join me. One of them happened to be on his company’s list of engineers they couldn’t lose at any cost. When the engineer told them he was leaving, they offered him the moon regarding stock and salary. They told him he could work on any project and have any team. Then one of the most important executives from Twitter joined me. I didn’t set out to poach anyone—it happened by accident—but when this happened, Dick Costolo, Twitter’s CEO (and my friend) had a professional obligation to meet me for a drink and chew me out. When he was done busting my chops, I said, “Can I offer you a little advice?” He said, “Oh, geez. What?” I said, “If you have a list of people that you don’t want to lose at any cost, don’t wait until they quit to offer them more money and more stock options.” He agreed. Then we ordered another round and made up.

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