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“Bill Gurley, the incredibly smart, wry, contrarian Silicon Valley VC and Texan deal maker, puts it this way: “I can’t make you the smartest or the brightest, but it’s doable to be the most knowledgeable. It’s possible to gather more information than somebody else.””

“Your executive team and managers are supposed to be looking out for roadblocks. They’re supposed to warn you so you can adjust course, or at least grab a helmet. But sometimes they don’t. So 20 percent of the time, individual contributors need to look up. And they need to look around. The sooner they start, the faster and higher they’ll advance in their career.”

“And you know what utterly beat us? Palm. Because Palm PDAs let you put the phone numbers you kept on scraps of paper or on your desktop computer into a device that you could carry with you. That’s it. That simple. You couldn’t jam a Rolodex into your pocket or purse, so Palm was the right solution for the time. It made sense. It had a reason to exist.”

“But what happens if you fall in love with the wrong thing? If you find a product or company that’s too early—the supporting infrastructure isn’t there, the customers don’t exist, the leadership has a crazy vision and won’t budge. What if you’re deeply passionate about quantum computing or synthetic biology or fusion energy or space exploration even though there’s no sign that any of those industries will bear fruit anytime soon? Then screw it. Go for it. If you love it, don’t worry about all my advice, don’t worry about the timing.”

“To do great things, to really learn, you can’t shout suggestions from the rooftop then move on while someone else does the work. You have to get your hands dirty. You have to care about every step, lovingly craft every detail. You have to be there when it falls apart so you can put it back together.”

“So when you’re looking at the array of potential careers before you, the correct place to start is this: “What do I want to learn?””

“Make a connection. That’s the best way to get a job anywhere. And if that seems impossible—if you follow your heroes on Twitter but can’t imagine they’ll ever pay any attention to you—I’m excited to tell you that that is complete bullshit. I doubt I’m anyone’s hero, but I’m an experienced, well-connected product designer who’s been lucky enough to make some famous technology. Most people assume I won’t pay any attention to people who randomly DM me on Twitter or send me unsolicited emails out of the blue. But sometimes I do. Not when people are just asking for a job. Or angling for funding. But I’ll notice people who come with something interesting to share. Something smart. Especially if they keep coming. If they sent me something cool last week and something cool this week and they keep bringing fascinating news or tech or ideas and they’re persistent, then I’ll start to recognize them. I’ll start to remember them, and respond. And that can turn into an introduction or a friendship or a referral or, potentially, a job at one of our portfolio companies.”

“A good mentor won’t hand you the answers, but they will try to help you see your problem from a new perspective.”

“Students seek out the best professors on the best projects when getting their master’s or PhD, but when they look for jobs, they focus on money, perks, and titles. However, the only thing that can make a job truly amazing or a complete waste of time is the people. Focus on understanding your field and use that knowledge to create connections with the best of the best, people you truly respect. Your heroes. Those (typically humble) rock stars will lead you to the career you want.”

“The CEO and executive team are mostly staring way out on the horizon—50 percent of their time is spent planning for a fuzzy, distant future months or years away, 25 percent is focused on upcoming milestones in the next month or two, and the last 25 percent is spent putting out fires happening right now at their feet. They also look at all the parallel lines to make sure everyone is keeping up and going in the same direction.”

“The founders started with a customer problem—a problem they experienced in their daily lives—then applied technology. The problem was simple: finding a cab in Paris was next to impossible and hiring private drivers was expensive and took forever. In the days before smartphones, the solution might have been to simply start a new kind of taxi or limo business. But the company’s timing was perfect—the sudden ubiquity of smartphones provided Uber with a platform and put customers into the right mindset to accept their solution. If I can order a toaster with an app on my phone, why shouldn’t I hail a car? That combination of a real problem, the right timing, and innovative technology allowed Uber to shift the paradigm—to create something that traditional cab companies couldn’t even dream of, never mind compete with.”

“Early adulthood is about watching your dreams go up in flames and learning as much as you can from the ashes. Do, fail, learn. The rest will follow.”

“The world is full of mediocre, middle-of-the-road companies creating mediocre, middle-of-the-road crap, but I’ve spent my entire life chasing after the products and people that strive for excellence. I’ve been incredibly lucky to learn from the best—from bold, passionate people who made a dent in the world.”

“Marc’s 1989 sketch of the Pocket Crystal in his big red notebook. On the next page he wrote, “This is a very personal object. It must be beautiful. It must offer the kind of personal satisfaction that a fine piece of jewelry brings. It will have a perceived value even when it’s not being used. It should offer the comfort of a touchstone, the tactile satisfaction of a seashell, the enchantment of a crystal.””

“Adulthood is commonly thought of as the time when learning is over and living begins. Yes! I’ve graduated! I’m done! But learning never ends. School has not prepared you to be successful for the rest of your life. Adulthood is your opportunity to screw up continually until you learn how to screw up a little bit less.”

“The best way to find a job you’ll love and a career that will eventually make you successful is to follow what you’re naturally interested in, then take risks when choosing where to work. Follow your curiosity rather than a business school playbook about how to make money. Assume that for much of your twenties your choices will not work out and the companies you join or start will likely fail.”

““The only failure in your twenties is inaction. The rest is trial and error.” —ANONYMOUS”

“I needed to learn. And the best way to do that was to surround myself with people who knew exactly how hard it was to make something great—who had the scars to prove it. And if it turned out to be the wrong move, well, making a mistake is the best way to not make that mistake again. Do, fail, learn.”

“The critical thing is to have a goal. To strive for something big and hard and important to you. Then every step you take toward that goal, even if it’s a stumble, moves you forward.”

“And you can’t skip a step—you can’t just have the answers handed to you and detour around the hard stuff. Humans learn through productive struggle, by trying it themselves and screwing up and doing it differently next time. In early adulthood you have to learn to embrace that—to know that the risks might not pan out but to take them anyway. You can get guidance and advice, you can choose a path by following someone else’s example, but you won’t really learn until you start walking down that path yourself and seeing where it takes you.”

“General Magic was an experiment. Not just in what we were making—and we were making something wholly, ridiculously, almost unbelievably new—but also in how to structure a company. The team was so impressive, packed with genius after genius, that there was no regard for “management.” No defined process. We just kind of . . . made stuff. Whatever our leaders thought would be cool.”

“It’s thinking about a problem or a customer need in a way you’ve never heard before, but which makes perfect sense once you hear it.”

“If you’re not solving a real problem, you can’t start a revolution.”

“If you’re passionate about something—something that could be solving a huge problem one day—then stick with it. Look around and find the community of people who are passionate about it, too. If there’s nobody else on Earth thinking about it, then you may truly be too early or going in the wrong direction. But if you can find even a handful of like-minded people, even if it’s just a tiny community of geeks building technology nobody has any idea how to turn into a real business, then keep going. Get in on the ground floor, make friends, and find mentors and connections that will bear fruit when the world spins just enough to make what you’re making make sense. You may not be at the same company as when you started, the vision may be different, the product may be different, and the technology will have changed. You may have to fail and fail and learn and learn and evolve and understand and grow.”

“You should know where you want to go, who you want to work with, what you want to learn, who you want to become.”

“The key is persistence and being helpful. Not just asking for something, but offering something. You always have something to offer if you’re curious and engaged. You can always trade and barter good ideas; you can always be kind and find a way to help.”

“After every podcast, he asks his interviewee in private, “Who are the top three people you know and respect who you think I should talk to next? Do you mind intro-ing me really quickly?””

“When you get a chance to work with legends and heroes and gods, you realize they’re none of the things that you’ve fabricated in your brain. They can be geniuses in one area and clueless in another. They can raise you up by praising your work, but you can also help them, catch things they miss, and build a relationship based not on starry-eyed hero worship but mutual respect.”

“Managers usually keep their eyes focused 2–6 weeks out. Those projects are pretty fleshed out and detailed, though they still have some fuzzy bits around the edges. Managers’ heads should be on a swivel—they often look down, sometimes look further out, and spend a fair amount of time looking side to side, checking in on other teams, making sure everything’s coming together for the next milestone.”

“Junior individual contributors spend 80 percent of their time looking straight down—maybe a week or two out—to see the fine points of their day-to-day work. In the early stages of your career, that’s the way it should be. You should be focused on getting your specific piece of each project done, done well, and out the door.”

“Your job isn’t just doing your job. It’s also to think like your manager or CEO. You need to understand the ultimate goal, even if it’s so far away that you’re not really sure what it’ll look like when you get there. That’s helpful in your day-to-day—knowing your destination lets you self-prioritize and make decisions about what you’re doing and how you’re doing it. But it’s also bigger than that. You want to make sure the direction you’re headed in still feels right—that you still believe in it. And you can’t ignore the other teams who are working by your side.”

“Fig. 1.4.2 When you look up and around, you can see if your medium- and long-term goals still make sense, and understand the needs and concerns of the teams around you. Talk to your internal customers, whoever you’re a customer of, and the people who are closest to the actual customer—marketing and support. That’s how you’ll know if you’re on track or if things are going seriously sideways. Matteo Vianello”

“Not only was she worried that the features we were building were charming but useless, she was also worried we wouldn’t actually build them. “We just worked with Sony marketing to make an ad campaign saying the Magic Link will be able to do all these things. Is it true? Can we actually deliver?” This was probably around the fifth time we’d pushed back our launch date. Many of the features we’d promised investors and partners had fallen through. The product was slow and buggy. And she wanted to know what was happening behind the scenes—not just what she was hearing from leadership. Where will wireless messaging work? Where won’t it work? What’s the customer experience really going to be? What are the trade-offs?”

“I hadn’t realized it, but all those people working parallel to me could see things I couldn’t. They had a completely different view of our world—a view that I wanted to understand. New perspectives are everywhere. You don’t have to drag a bunch of people off the street to stare at your product and tell you what they think. Start with your internal customers. Everyone in a company has customers, even if they’re not building anything. You’re always making something for someone—the creative team is making stuff for marketing, marketing is making stuff for the app designers, the app designers are making stuff for the engineers—every single person in the company is doing something for someone, even if it’s just a coworker on another team.”