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  • 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.

  • Traditional schooling trains people to think incorrectly about failure. You’re taught a subject, you take a test, and if you fail, that’s it. You’re done. But once you’re out of school, there is no book, no test, no grade. And if you fail, you learn. In fact, in most cases, it’s the only way to learn—especially if you’re creating something the world has never seen before.

  • 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.

  • Humans learn through productive struggle, by trying it themselves and screwing up and doing it differently next time.

  • 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.

  • You might screw up. Your company might fail. You might have so many butterflies in your stomach you’ll be worried you got food poisoning. And that’s okay. It’s exactly what should be happening. If you don’t feel those butterflies then you’re not doing it right. You have to push yourself up the mountain, even if it means you might fall off a cliff.

  • You should never kill yourself for your job, and no job should ever expect that of you.

  • Cool technology isn’t enough. A great team isn’t enough. Plenty of funding isn’t enough. Too many people throw themselves blindly at hot trends, anticipating a gold rush, and end up falling off a cliff.

  • “If you make it, they will come” doesn’t always work. If the technology isn’t ready, they won’t come for sure. But even if you’ve got the tech, then you still have to time it right. The world has to be ready to want it. Customers need to see that your product solves a real problem they have today—not one that they may have in some distant future.

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

  • Seemingly impossible problems that a decade ago would have cost billions to solve, requiring massive investments from giant firms, can now be figured out with a smartphone app, a small sensor, and the internet. And that means there are thousands of people all over the world finding opportunities to change the way people work and live and think.

  • 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. You have to actually do the job. You have to love the job.

  • 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.

  • What you do matters. Where you work matters. Most importantly, who you work with and learn from matters. Too many people see work as a means to an end, as a way to make enough money to stop working. But getting a job is your opportunity to make a dent in the world. To put your focus and energy and your precious, precious time toward something meaningful.

  • You don’t have to be an executive right away, you don’t have to get a job at the most amazing, world-changing company right out of college, but you should have a goal. You should know where you want to go, who you want to work with, what you want to learn, who you want to become. And from there, hopefully you’ll start to understand how to build what you want to build.

  • 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.

  • Make a connection. That’s the best way to get a job anywhere.

  • There is nothing in the world that feels better than helping your hero in a meaningful way and earning their trust—watching them realize you know what you’re talking about, that you can be relied on, that you’re someone to remember. And then seeing how that respect evolves as you move on to the next job, and the next.

  • Think of a project as a straight line in time—there’s a beginning and (hopefully) an end. Everyone is walking at the same pace, day by day, on parallel lines—a line for engineering, marketing, sales, PR, customer support, manufacturing, legal, etc.

  • The most wonderful part of building something together with a team is that you’re walking side by side with other people. You’re all looking at your feet and scanning the horizon at the same time. Some people will see things you can’t, and you’ll see things that are invisible to everyone else. So don’t think doing the work just means locking yourself in a room—a huge part of it is walking with your team. The work is reaching your destination together. Or finding a new destination and bringing your team with you.

  • If you’re thinking of becoming a manager, there are six things you should know:

    1. You do not have to be a manager to be successful.

    2. Remember that once you become a manager, you’ll stop doing the thing that made you successful in the first place.

    3. Becoming a manager is a discipline.

    4. Being exacting and expecting great work is not micromanagement.

    5. Honesty is more important than style.

    6. Don’t worry that your team will outshine you.

  • Most managers are afraid that the people who work for them are going to be better than them. But you need to think of being a manager more like being a mentor or a parent. What loving parent wants their child NOT to succeed? You want your kids to be more successful than you, right?

  • If you’re a manager—congratulations, you’re now a parent. Not because you should treat your employees like children, but because it’s now your responsibility to help them work through failure and find success. And to be thrilled when they do.

  • If you’re a good manager and build a good team, that team will blast off. So lean into it. Cheer them on when they get promoted. Glow with pride when they kick ass at a board meeting or present their work to the entire company. That’s how you become a good manager. That’s how you start to love the job.

  • A/B testing just means running a digital experiment where you test option A versus option B with customers. So some see a blue button, some see an orange button, and you see which button gets the most clicks. It’s an incredible tool—infinitely faster than customer panels and so much easier to interpret.

  • When you’re making something new, there’s no way to definitively prove that people will like it. You just have to ship it—put it out into the world (or at least in front of forgiving customers or internal users) and see what happens.

  • Prepare for some wind and some hail, but don’t worry about getting swept away.

  • Make new relationships, beyond business—talk to people outside your bubble. Get to know what else is out there. Meet some new human beings. Networking is something you should be doing constantly—even when you’re happily employed.

  • You should talk to people and make connections because you’re naturally curious. You want to know how other teams at your company work and what people do. You want to talk to your competitors because you’re all working to solve the same problems and they’re taking a different approach. You want your projects to be successful, so you don’t just talk to your immediate teammates at lunch—you grab lunch with your partners, your customers, their customers, their partners. You talk to everyone: get their ideas and their perspectives. In doing so you may be able to help someone or make a friend or strike up an interesting conversation.

  • People won’t remember how you started. They’ll remember how you left.

  • The threat of leaving may be enough to push your company to get serious and make whatever change you’re asking for. But it might not. Quitting should never be a negotiating tactic—it should be the very last card you play.

  • Prototype as much of the full customer experience as possible. Make the intangible tangible so you can’t overlook the less showy but incredibly important parts of the journey. You should be able to map out and visualize exactly how a customer discovers, considers, installs, uses, fixes, and even returns your product. It all matters.

  • Makers often focus on the shiny object—the product they’re building—and forget about the rest of the journey until they’re almost ready to deliver it to the customer. But customers see it all, experience it all. They’re the ones taking the journey, step-by-step. And they can easily stumble and fall when a step is missing or misaligned.

  • Every product should have a story, a narrative that explains why it needs to exist and how it will solve your customer’s problems.

  • A good product story has three elements:

    • It appeals to people’s rational and emotional sides.

    • It takes complicated concepts and makes them simple.

    • It reminds people of the problem that’s being solved—it focuses on the “why.

  • That “why”is the most critical part of product development—it has to come first. Once you have a strong answer for why your product is needed, then you can focus on how it works. Just don’t forget that anyone encountering your product for the first time won’t have the context you have. You can’t just hit customers on the head with the “what”before you tell them the “why.”

  • And always remember that your customers’ brains don’t always work like yours.

  • If you’re going to pour your heart into creating something new, then that thing should be disruptive. It should be bold. It should change something.

  • If you’ve truly made something disruptive, your competition probably won’t be able to replicate it quickly.

  • Underpromise and overdeliver.

  • You cannot be afraid to disrupt the thing that made you successful in the first place. Even if it made you hugely successful.

  • If you do it right, one disruption will fuel the next. One revolution will domino into another. People will laugh at you and tell you it’s ludicrous, but that just means they’re starting to pay attention. You’ve found something worth doing. Keep doing it.

  • When you’re leading a team or project to launch V1—the first version of a product that’s new for you and your team—it’s like heading out into the mountains with friends for the first time. You think you have everything you need to camp and climb, but you’ve never done it before. So you’re tentative. And you’re slow. But you take your best guess at what you need and where you’re going and head into the wild.

  • You need constraints to make good decisions and the best constraint in the world is time. When you’re handcuffed to a hard deadline, you can’t keep trying this and that, changing your mind, putting the finishing touches on something that will never be finished.

  • Keep your project small as long as you can. And don’t allocate too much money at the start. People do stupid things when they have a giant budget—they overdesign, they overthink. That inevitably leads to longer runways, longer schedules, and slower heartbeats. Much, much slower.

  • Generally any brand-new product should never take longer than 18 months to ship—24 at the limit. The sweet spot is somewhere between 9 and 18 months. That applies to hardware and software, atoms and bits.

  • If a team is constantly updating their product, then customers start tuning out. They don’t have time to learn how the product works—certainly not to master it—before suddenly it’s new again.

  • Any more announcements or big changes and you’ll start confusing people, any fewer and they’ll start forgetting about you. So have at least one really big launch and another one to three smaller launches every year.

  • Figure out how to find product/market fit for V1, then get the product fixed up and properly marketed to a wider audience with V2, and only then can you focus on optimizing the business so it can be sustainable and profitable with V3.

  • No matter what you’re building, reaching profitability will take longer than you think. You will almost certainly not make any money with V1. You’ll need to reinvent yourself at least three times. Sometimes many more.

  • There are three elements to every great idea:

    1. It solves for “why.” Long before you figure out what a product will do, you need to understand why people will want it. The “why” drives the “what.”

    2. It solves a problem that a lot of people have in their daily lives.

    3. It follows you around.

  • The more amazing an idea seems—the more it tugs at your gut, blinds you to everything else—the longer you should wait, prototype it, and gather as much information about it as possible before committing. If this idea is going to eat up years of your life, you should at least take a few months to research it, build out detailed (enough) business and product development plans, and see if you’re still excited about it. See if it will chase you.

  • Most startups are born from people getting so frustrated with something in their daily experience that they start digging in and trying to find a solution.

  • Throwing darts at a wall is not how you pick a great idea. Anything worth doing takes time. Time to understand. Time to prepare. Time to get it right. You can fast-track a lot of things and skimp on others, but you cannot cheat time.

  • Your first hires are crucial—they’ll help you architect what your business and culture will become.

  • If you want to start a company, if you want to start anything, to create something new, then you need to be ready to push for greatness. And greatness doesn’t come from nothing. You have to prepare. You have to know where you’re headed and remember where you came from. You have to make hard decisions and be the mission-driven “asshole.”

  • No matter which route you take—VC or angel or strategic or bootstrap—starting a company is hard. Getting money is hard. There are no shortcuts, no easy path, no room for dumb luck. But if you do it right, if you choose the right people, then you’ll genuinely like your investors and they’ll help you through the tough times that always come with a startup. They’ll be there in sickness and in health and you’ll end up in a happy marriage. Maybe even a few of them. After that, all that’s left to do is build a business.

  • Do not think you can serve two masters. No matter what you’re building, you can never forget who you’re building it for. You can only have one customer. Choose wisely.

  • Writing by hand was important for me. I wasn’t staring at a screen, getting distracted by my email. A computer or a smartphone between you and the team is a huge barrier to focus and sends a clear message to everyone in the meeting: whatever I’m looking at on my screen is more important than you.

  • There will be no break unless you force yourself to take one.

  • Part of your job is not to go completely nuts at work and take it out on your team.

  • There are moments where you simply cannot function as a human, never mind a leader, and you need to recognize them and walk out the door. Don’t make a bad decision because you’re frustrated and overworked—get your head on straight and come in fresh the next day.

  • If something is your fault, tell them what you did. Tell them what you’ve learned from it. And tell them how you’ll prevent it from ever happening again. No evading, blaming, or making excuses. Just accept responsibility and be a grown-up.

  • Every failure is a learning experience. A complete meltdown is a PhD program.

  • So when bringing in new employees—especially execs—you shouldn’t just throw them in the deep end, hand them a branded company notebook, and think you’re done. The first month or two are crucial and should be a period of positive micromanagement.

  • You can’t wait for the perfect A+ candidate to appear for every single empty slot. You need to hire. The best of the best don’t always want to join a big team, or they’re tied up in another job, or you can’t afford them or give them the titles or responsibilities they want.

  • It’s either grow or die. Stasis is stagnation. Change is the only option.

  • Change is growth and growth is opportunity. Your company is an organism; its cells need to divide to multiply, they need to differentiate to become something new. Don’t worry about what you’re going to lose—think about what you’re going to become.

  • At its core, designing simply means thinking through a problem and finding an elegant solution. Anyone can do that. Everyone should.

  • Being a good designer is more a way of thinking than a way of drawing. It’s not just about making things pretty—it’s about making them work better.

  • Literally the only way to make a really good product is to dig in, analyze your customer’s needs, and explore all the possible options (including the unexpected ones).

  • There are no perfect designs. There are always constraints. But you choose the best of all the options—aesthetically, functionally, and at the necessary price point.

  • Not everyone can be a great designer, but everyone can think like one. Designing isn’t something in your DNA that you’re simply born with—it’s something you learn.

  • To be a great designer you can’t lock yourself in a room—you have to connect with your team, with your customer and their environment, and other teams who may have innovative ideas to bring to the table. You have to understand your customer’s needs and all the different ways you can address them. You have to look at a problem from all angles. You have to get a little creative. And you have to notice the problem in the first place.

  • You can’t solve interesting problems if you don’t notice they’re there.

  • You just have to notice the problem. And not wait around for someone to solve it for you.

  • When building a product, product management and the marketing team should be working together from the very beginning. As you build, you should continue to use marketing to evolve the story and ensure they have a voice in what the product becomes.

  • The ultimate job of marketing is to find the very best way to tell the true story of your product.

  • Steve Jobs often said, “The best marketing is just telling the truth.”

  • There’s no four-year college degree for product management, no obvious source you can hire from. Amazing product managers usually emerge from other roles. They start in marketing or engineering or support, but because they care so deeply about the customer, they start fixing the product and working to redefine it, rather than just executing someone else’s spec or messaging.

  • The best salespeople are the ones who maintain relationships even if it means not making money that day.

  • When you start out, your first customers are incredibly precious. They’re the ones who love you best, who take a risk on you. And they can make or break your company—they’re the source of all your initial word of mouth.

  • If a leader gets distracted from the customer—if business goals and spreadsheets full of numbers for shareholders become a higher priority than customer goals—the whole organization can easily forget what’s most important.

  • You don’t have to be an expert in everything. You just have to care about it.

  • Great leaders can recognize good ideas even if those ideas didn’t come out of their own mouths. They know that good ideas are everywhere. They’re in everyone.

  • The brain patterns of entrepreneurs thinking about their startups are extremely similar to those of parents thinking about their children.

  • As a parent you never stop worrying about your kid, planning for your kid, pushing your kid to do better, be better. A parent’s job isn’t to be friends with their kids all the time—it’s to build them into independent, thoughtful humans who will be ready and able to thrive in the world one day without their parents.

  • If you aren’t failing, you aren’t trying hard enough. Learn from the screwups.

  • CEOs have to make incredibly unpopular decisions—lay people off, kill projects, rearrange teams. Often you’ll have to take decisive action, hurt people to save the company, to cut out a cancer. You can’t skip surgery because you don’t want to upset Team Tumor.

  • When you’re an independent contributor, you can typically look at something you’ve made that week and be proud of it. When you’re a manager, you can look at the collective achievement of your team and feel a sense of accomplishment and pride. When you’re a CEO, you dream that maybe, ten years down the road, some people will think you did a good job. But you can never tell how you’re doing in the moment. You can never sit back and look at a job well done.

  • You want board members who are truly, deeply excited by what you’re making. Who can’t wait to hear what you’ve been up to. Who aren’t just there for the meetings but are with you day in and day out, helping you, finding opportunities for you to succeed. You want a board that loves your company. And that your company loves back.

  • When two fully formed companies merge, their cultures need to be compatible. Just like any relationship, everything ultimately comes down to how well people get along, what their goals are, what their priorities are, and what drives them crazy. Fifty to 85 percent of all mergers fail due to cultural mismatches.

  • When people pay for something, they value it. If something is free, it is literally worthless.

  • If something happens only rarely, it’s special. If it happens all the time, the specialness evaporates.

  • Subsidizing perks rather than giving them away is obviously much better financially for your business, too.

  • Part of the founder CEO myth is that once you’re a CEO, there’s no going back—that nobody wants to leave the job once they’ve got it. But people can bounce back and forth.

  • The world will not judge you for taking some time off.

  • You absolutely need to get bored before you can find new things to be inspired by.


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