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Build: An Unorthodox Guide to Making Things Worth Making

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Build: An Unorthodox Guide to Making Things Worth Making

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But certain things you can’t blow up. Human nature doesn’t change, regardless of what you’re building, where you live, how old you are, how wealthy or not.

Everybody trying to do something meaningful needs and deserves to have a mentor and coach—someone who’s seen it and done it and can hopefully help you through the toughest moments in your career. A good mentor won’t hand you the answers, but they will try to help you see your problem from a new perspective. They’ll loan you some of their hard-fought advice so you can discover your own solution.

I tried to build the iPhone twice. Everybody knows about the second time. The time we succeeded. Few people know about the first.

No matter how much you learn in school, you still need to get the equivalent of a PhD in navigating the rest of the world and building something meaningful. You have to try and fail and learn by doing.

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.

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.

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?” Not “How much money do I want to make?” Not “What title do I want to have?” Not “What company has enough name recognition that my mom can brutally crush the other moms when they boast about their kids?”

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.

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.

So I went where I could grow. The title and the money weren’t important. The people were. The mission was. The opportunity was all that mattered.

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

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.

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

Most kids don’t consciously examine any of these choices. They mimic their parents. And when you’re a kid, that’s usually fine. It’s necessary. But you’re not a kid anymore.

And after you move out of your parents’ house, there’s a window—a brief, shining, incredible window—where your decisions are yours alone. You’re not beholden to anyone—not a spouse, not kids, not parents. You’re free. Free to choose whatever you’d like. That is the time to be bold.

Just because you’re on your own doesn’t mean you have to be alone with your decisions.

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. I learned more from my first colossal failure than I ever did from my first success.

After four years, I realized there was a whole world of thinking that was needed before a line of code should be written. And that thinking was fascinating. That thinking was what I wanted to

General Magic was making incredible technology but wasn’t making a product that would solve real people’s problems.

That’s what you’re looking for when you’re young, when you think you know everything then suddenly realize you have no idea what you’re doing: a place where you can work as hard as you can to learn as much as you can from people who can make something great. So even if the experience kicks your ass, the force of that kick will propel you into a new stage of your life. And you’ll figure out what to do next.

A company that’s likely to make a substantial change in the status quo has the following characteristics: It’s creating a product or service that’s wholly new or combines existing technology in a novel way that the competition can’t make or even understand. This product solves a problem—a real pain point—that a lot of customers experience daily. There should be an existing large market. The novel technology can deliver on the company vision—not just within the product but also the infrastructure, platforms, and systems that support it. Leadership is not dogmatic about what the solution looks like and is willing to adapt to their customers’ needs. 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 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.

Steve Jobs once said of management consulting, “You do get a broad cut at companies but it’s very thin. It’s like a picture of a banana: you might get a very accurate picture but it’s only two dimensions, and without the experience of actually doing it you never get three dimensional. So you might have a lot of pictures on your walls, you can show it off to your friends—I’ve worked in bananas, I’ve worked in peaches, I’ve worked in grapes—but you never really taste it.”

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.

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.

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

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.

But if you can, try to get into a small company. The sweet spot is a business of 30–100 people building something worth building, with a few rock stars you can learn from even if you aren’t working with them every day.

And let me tell you, 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. That’s the great thing about heroes. You can use their inspiration to drive you. If you do it right, and listen carefully, they’ll share decades of learning. And then, one day, you might return the favor.

  1. Look up: Look beyond the next deadline or project and forward to all the milestones coming up in the next few months. Then look all the way down to your ultimate goal: the mission. Ideally it should be the reason you joined the project in the first place. As your project progresses, be sure the mission still makes sense to you and that the path to reach it seems achievable. 2. Look around: Get out of your comfort zone and away from the immediate team you’re on. Talk to the other functions in your company to understand their perspectives, needs, and concerns. This internal networking is always useful and it can give you an early warning if your project is not headed in the right direction.

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.

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. You’re somebody’s customer, too—so talk to whoever is doing work for you. Show up with something of value or a pertinent question. Try to understand what their roadblocks are and what they’re excited about. And talk to the people who are closest to the customer, like marketing and support—find teams who communicate with customers day in and day out and hear their feedback directly.

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.

Sales were understandably not great, though not terrible. But it was incredibly frustrating—we had put together all the right pieces except one: a real sales and retail partnership. Another lesson learned via gut punch.

  1. Being exacting and expecting great work is not micromanagement. Your job is to make sure the team produces high-quality work. It only turns into micromanagement when you dictate the step-by-step process by which they create that work rather than focusing on the output.

Honesty is more important than style. Everyone has a style—loud, quiet, emotional, analytical, excited, reserved. You can be successful with any style as long as you never shy away from respectfully telling the team the uncomfortable, hard truth that needs to be said.

the incessant questions and prodding. The micromanagement. When you’re a manager, you’re no longer just responsible for the work. You’re responsible for human beings. And while that seems obvious—yes, that’s the whole point of the job—it’s a difficult thing to grapple with when all of a sudden eighty people are looking at you, expecting you to know how to lead them.

A star individual contributor (IC) is incredibly valuable. Valuable enough that many companies will pay them just as much as they’d pay a manager. A truly great IC will be a leader in their chosen function and also become an informal cultural leader, someone who people across the company will seek out for advice and mentorship.

Recognition of incredible ICs is most common in engineering, but it’s becoming more common in other disciplines.

Many companies also offer the option of being a team lead—or at least they should. This is a kind of a midpoint between an IC and manager. You have some authority to critique, shape, and drive the team’s output, but nobody reports to you and you’re not dealing with budgets, org charts, or management meetings.

A lot of engineers only trust other engineers. Just like finance people only trust finance people. People like people who think like them. So engineers often keep their distance from sales, marketing, creative—all the functions that are soft, squishy.

One of the hardest parts of management is letting go. Not doing the work yourself. You have to temper your fear that becoming more hands-off will cause the product to suffer or the project to fail. You have to trust your team—give them breathing room to be creative and opportunities to shine. But you can’t overdo it—you can’t create so much space that you lose track of what’s going on or are surprised by what the product becomes. You can’t let it slide into mediocrity because you’re worried about seeming overbearing. Even if your hands aren’t on the product, they should still be on the wheel.

Examining the product in great detail and caring deeply about the quality of what your team is producing is not micromanagement. That’s exactly what you should be doing.

As a manager, you should be focused on making sure the team is producing the best possible product. The outcome is your business. How the team reaches that outcome is the team’s business.

It helps to agree on the process early. To define it up front—here’s our product development process, here’s our design process, our marketing process, our sales process. Here’s our schedule and how we work and how we work together. Everyone—manager and team—signs off on it and then the manager has to let go. They let the team work. Then they make sure everything’s heading in the right direction in regular team meetings. These meetings should be structured to get you and the team as much clarity as possible. You should have a weekly crib sheet that helps you keep your priorities and the questions you need to ask top of mind. [See also: Chapter 4.5: Killing Yourself for Work: Everyone thought I was crazy.] Write down a list of what you’re worried about for each project and person so you can immediately see when the list is getting too long and you need to either dive deeper or back off.

And then just be honest with them. Even if things aren’t going well, don’t avoid telling them the hard truth. Tear off the Band-Aid. If either of you is nervous, you can start the conversation with something positive, ease into it, but don’t ignore the elephant in the room, don’t tiptoe around the reason you need to talk. It’s important to remember that even if you have to criticize someone’s work or their behavior, you’re not doing it to hurt them. You’re there to help. Every word should come from a place of caring. So tell them what’s holding them back. Then make a plan to work on it together.

But those formal reviews should simply be an exercise in writing down the things you’re talking about every week. The team should be getting your feedback—good and bad—in the moment rather than waiting to be surprised by it a few months down the road.

The key for me was separating the problems of the company from my personal issues, identifying when my own actions were causing frustrations on the team versus knowing that some things were entirely out of my control. That is difficult stuff to figure out by yourself—it’s hard to dig around in your own brain, just like it’s hard to do yoga at first without an instructor. My therapist was my coach, my teacher—he helped me understand why I was being such a micromanager. He showed me which parts of my personality I needed to control to effectively lead a team.

But I didn’t try to change who I was. You are who you are. If you have to completely rearrange your personality to become a manager, then it will always be an act and you won’t get comfortable in the role.

So as a manager, you have to find what connects with your team. How can you share your passion with them, motivate them?

The answer, as usual, comes down to communication. You have to tell the team why. Why am I this passionate? Why is this mission meaningful? Why is this small detail so important that I’m flipping out right now when nobody else seems to think it matters? Nobody wants to follow someone who throws themselves at windmills for no reason. To get people to join you, to truly become a team, to fill them with the same energy and drive that’s bubbling within you, you need to tell them the why.

Helping people succeed is your job as a manager. It’s your responsibility to make sure they can become the best versions of themselves. You need to create a setting where they can surprise you. And where they can surpass 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?”

There’s a reason everyone congratulates parents when their kids do something great—because the kid’s achievement is their own, but it also reflects the parent’s influence. The parent can take pride in their kid’s accomplishment because they know all the time, effort, guidance, hard conversations, and hard work that went into it.

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.

You make hundreds of tiny decisions every day, but then there are the critical ones, the ones where you’re trying to predict the future, the ones that will put a lot of resources on the line. In those instances, it’s important to realize what kind of decision you’re faced with: Data-driven: You can acquire, study, and debate facts and numbers that will allow you to be fairly confident in your choice. These decisions are relatively easy to make and defend and most people on the team can agree on the answer. Opinion-driven: You have to follow your gut and your vision for what you want to do, without the benefit of sufficient data to guide you or back you up. These decisions are always hard and always questioned—after all, everyone has an opinion.

everyone wanted data so they wouldn’t have to make decisions themselves. Instead of moving forward with a design, you’d hear, “Well, let’s just test it.” Nobody wanted to take responsibility for what they were making.

So you have to design the options and the tests to really know what you’re testing. You have to think through what A and B are rather than let them be randomly assigned by an algorithm or thoughtlessly thrown against a wall to see what sticks. And that takes insight and knowledge of the entire customer journey. You need a hypothesis, and that hypothesis should be part of a bigger product vision. So you can A/B test where the “Buy” button should go on a Web page, whether it should be blue or orange, but you shouldn’t be testing whether or not a customer should buy online. If you’re testing the core of your product, if the basic functionality can flex and change depending on the whims of an A/B test, then there is no core. There’s a hole where your product vision should be and you’re just shoveling data into the void.

If a product is really new, there’s nothing to compare it to, nothing to optimize, nothing to test.

Eventually our team figured it out—we stopped throwing money at consultants, stopped spinning in circles, started moving forward and trusting ourselves and the trusted opinions of smart people around us. We made decisions. I made decisions. This is in. This is out. This is how it’s going to work. Not everyone on the team agreed with me. That’ll happen sometimes when one person has to make the final call. In those moments it’s your responsibility as a manager or a leader to explain that this isn’t a democracy, that this is an opinion-driven decision and you’re not going to reach the right choice by consensus. But this also isn’t a dictatorship. You can’t give orders without explaining yourself. So tell the team your thought process. Walk through all the data you looked at, all the insights you gathered, and why you ultimately made this choice. Take people’s input. Listen, don’t react. There may be a minority of team members who agree with the decision; there might be some good feedback that makes you modify your plan. If not, give the speech: I understand your position. Here are the points that make sense for our customers, here are the ones that don’t. We have to keep moving and, in this instance, I have to follow my gut. Let’s go. Even if some people on your team don’t love that answer, they’ll respect it. And they’ll trust you—they’ll know that they can speak up and criticize your choices and not get immediately shot down. And then they can sigh, and shrug, and go back to their team, communicate the “why” of the decision, and get on the train.

It’s important at this stage to have a boss who understands the kinds of decisions you’re facing. You need a leader who trusts you, who’s ready to back you up.

Here are a few reasons why a leader may sit on your idea and then call in the consultants: Delay. They may be waiting for something—a promotion or a bonus—and don’t want to take a risk until they get it. Fear for their job. They may be convinced that the consequence of failure is that they’ll lose this project or their position or—if the failure is spectacular enough—their job. They don’t have the time or don’t want to bother. They don’t believe it’s worth the effort to dig in and really understand the decision, choose from the array of options before them, and take a risk. They just want someone else to do it and make them look smart. They know what they want but don’t want to hurt anyone’s feelings. They want to be seen as “nice” so they’ll just keep testing the water, asking for more data again and again until you’re worn out and exasperated.

Storytelling is how you get people to take a leap of faith to do something new. It’s what all our big choices ultimately come down to—believing a story we tell ourselves or that someone else tells us. Creating a believable narrative that everyone can latch on to is critical to moving forward and making hard choices. It’s all that marketing comes down to. It’s the heart of sales. And right now you’re selling—your vision, your gut, your opinion.

“It’s not data or intuition; it’s data and intuition.” You need both. You use both. And sometimes the data can only take you so far. In those moments, all you can do is take a leap. Just don’t look down.

according to University of San Diego professor Simon Croom, up to 12 percent of corporate senior leadership exhibit psychopathic traits.

Plenty of people think I’m an asshole. It’s usually because I get loud. I ask nicely a few times and then—if we’re still not getting anywhere—I stop asking nicely. I put pressure on myself and the people around me. I don’t let up. I expect the best—from myself, from everyone else. I care deeply about our mission, our team, our customers. I can’t stop myself from caring. So I push. If something seems off, if I think there’s a chance we can do better, that the customer can get more, then I do not let up. I do not let things slide. [See also: Chapter 6.1: Becoming CEO.] I push people who are experts, who already know how it’s done, how it’s always been done, to find a new way to do it. And that’s a lot to take. It’s not easy to work with. I would never claim otherwise. But pushing for greatness doesn’t make you an asshole. Not tolerating mediocrity doesn’t make you an asshole. Challenging assumptions doesn’t make you an asshole. Before dismissing someone as “just an asshole,” you need to understand their motivations.

There’s a world of difference between being emphatic and passionate to benefit the customer versus bullying someone to appease your own ego. It’s not always an obvious difference to the person on the other end. It’s hard to walk into a hurricane and think, Ah, this is a passionate hurricane. I just need to let it blow for a little while and then present some helpful data. But some hurricanes can be reasoned with. Some cannot.

So ask. Don’t be afraid to push. They’ll respect you more if you stand up for what you believe in. Mission-driven “assholes” want to be better at their jobs and fulfill that all-important mission—they want to make sure the company is heading in the right direction. So if it’s in the best interest of the customer, they’ll hear you and change their mind. Eventually.

So she did the only thing you can do when faced with a controlling asshole: Kill ’em with kindness. Ignore them. Try to get around them. Quit. In that order.

Political assholes thrive in large organizations where they can pull the kind of Machiavellian BS that makes you sound crazy and paranoid when you’re describing it. They find people who aren’t exceptional at their jobs and protect them in exchange for their allegiance. They get dirt on their peers—who’s having an affair with his admin? Can we get HR to cover it up?—then those people are indebted for life. It’s like the mafia. But instead of killing people, they kill good ideas.

The bullshit-asymmetry theory, Brandolini’s law, will be at play here: “The amount of energy needed to refute bullshit is an order of magnitude higher than to produce it.”

That’s the thing about assholes—they’re so incredibly unpleasant that they stand out in your memory. They get a whole chapter in your book. But most people just want to go to the office and make something cool. The vast majority of people who cause you trouble aren’t malicious or Machiavellian—they’re struggling, or first-time managers, or in the wrong job, or just having a really, really bad day. Maybe their kid’s not sleeping. Maybe their mom died. Even the nicest people on Earth can act like assholes sometimes. Or maybe they’re passionate hurricanes who are pushing you further than you thought you could go, because they know you’re talented and that you’re holding yourself back. Most people aren’t assholes. And even if they are, they’re also human. So don’t walk into a job trying to get anyone fired. Start with kindness. Try to make peace. Assume the best… . and if that doesn’t work, then remember that what goes around comes around. Although it never comes fast enough.

Once you do decide to quit, make sure you leave in the right way. You’ve made a commitment, so follow through and try to finish as much of what you started as possible. Find a natural breakpoint in your project—the next big milestone—and aim to leave then. The longer you’re at a company, and the higher up you are, the longer it will take to transition out. Individual contributors can usually give a few weeks to a couple months of notice. CEOs may need a year or more.

Most people know in their gut when they should quit and then spend months—or years—talking themselves out of it.

And I want to make it very clear: hating your job is never worth the money. I need to repeat that: hating your job is never worth whatever raise, title, or perks they throw at you to stay.

Anyone who’s ever stuck with a job they hated knows the feeling. Every meeting, every pointless project, every hour stretches on and on. You don’t respect your manager, you roll your eyes at the mission, you stagger out the door at the end of the day exhausted, dragging yourself home to complain to family and friends until they’re as miserable as you are. It is time and energy and health and joy that disappear from your life forever. But hey, that title, that stature, that money—it’s worth it all, right? Don’t get trapped. Just because you don’t know of any other better options doesn’t mean they don’t exist. There is other money. There are other jobs.

If you’re a manager or senior leader, it’ll honestly feel like forever—I had a nine-month transition out of Google Nest. At Apple, it took twenty months. People won’t remember how you started. They’ll remember how you left. But don’t let that deter you from making the choice and getting out. Once you find yourself in a place where you believe in the mission, everything changes.

Of course, you may need to quit that job, too. Because once you’re committed to a mission, to an idea—that’s the thing you should stick to. The company is secondary. If you find something that inspires you, then follow the best opportunities to pursue it. I got hooked on personal electronics and followed that passion across five companies. It only became really lucrative at the very end, but it was what I loved to do, so I kept finding new opportunities to do it. Each job took a different angle, a new perspective on the same problem, and eventually I had a rich, 360-degree view of the challenge I wanted to solve and all the possible solutions. The idea was much more precious than the company signing my paychecks.

If you’re going to get everyone’s attention, make sure it’s to support the mission, not for personal gain. Think through the problems that are plaguing your project. Write down thoughtful, insightful solutions. Present them to leadership. Those solutions may not work, but the process will be at the very least educational. Don’t nag, but be persistent, choose your moment wisely, be professional, and don’t hold back about the consequences if you don’t succeed.

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.

So before you quit, you’d better have a story. A good, credible, and factual one. You’ll need to have a rationale for why you left. And you’ll need one for why you want to join whatever company you’re heading to next. These should be two very different narratives. You’ll need them for the interview, but also for yourself—to make sure you’ve really thought things through. And to make sure you’re making the right choice for the next job.

Sometimes all the calculations, negotiations, discussions with your manager and meetings with HR are entirely beside the point. Sometimes it’s just time to go. And when that moment comes, you’ll probably know. Quit and go do something you’ll love.

So don’t just make a prototype of your product and think you’re done. 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.

If hardware doesn’t absolutely need to exist to enable the overall experience, then it should not exist. Of course, sometimes you do need hardware—it can’t be avoided. But when that happens, I still tell people to put it away. I say, “Don’t tell me what’s so special about this object. Tell me what’s different about the customer journey.” Your product isn’t only your product. It’s the whole user experience—a chain that begins when someone learns about your brand for the first time and ends when your product disappears from their life, returned or thrown away, sold to a friend or deleted in a burst of electrons.

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. Matteo Vianello

Your customer doesn’t differentiate between your advertising and your app and your customer support agents—all of it is your company. Your brand. All of it is one thing. But we forget. Too often makers only think of the user experience as that moment when the customer touches an object or taps a screen. The moment they actually use the thing—whether it’s made of atoms or bits or both. The thing is always central.

There are bumps between Awareness and Acquisition, between Onboarding and Usage, between every phase of the journey, that you have to help customers over. In each of these moments, the customer asks “why?” Why should I care? Why should I buy it? Why should I use it? Why should I stick with it? Why should I buy the next version? Your product, marketing, and support have to grease the skids—continually communicate and connect with customers, give them the answers they need, so they feel like they’re on a smooth ride, a single continuous, inevitable journey. To do that right, you have to prototype the whole experience—give every part the weight and reality of a physical object. Regardless of whether your product is made of atoms or bits or both, the process is the same. Draw pictures. Make models. Pin mood boards. Sketch out the bones of the process in rough wireframes. Write imaginary press releases. Create detailed mock-ups that show how a customer would travel from an ad to the website to the app and what information they would see at each touchpoint. Write up the reactions you’d want to get from early adopters, the headlines you’d want to see from reviewers, the feelings you want to evoke in everyone. Make it visible. Physical.

Get it out of your head and onto something you can touch. And don’t wait until your product is done to get started—map out the whole journey as you map out what your product will do. That’s how you hack your brain. How you hack the brains of everyone on your team. Start from that very first moment of the customer journey. You should be prototyping your marketing long before you have anything to market.

A vital part of the customer experience is post-sale. How do you stay connected to your customer in a way that’s actually useful? How do you keep on delighting people instead of just marketing to them, selling and selling until they’re sick of you?

When a company gives that kind of care and attention to every part of the journey, people notice. Our product was good, but ultimately it was the whole journey that defined our brand. That’s what made Nest special. It’s what makes Apple special. It’s what allows businesses to reach beyond their product and create a connection—not with users and consumers, but with human beings. It’s how you create something that people will love.

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 keep in mind that customers aren’t the only ones who will hear this story. Telling the story is how you attract people to your team or investors to your company. It’s what your salesperson puts in their slide deck and what you put in your board presentation. The story of your product, your company, and your vision should drive everything you do.*

He used a technique I later came to call the virus of doubt. It’s a way to get into people’s heads, remind them about a daily frustration, get them annoyed about it all over again. If you can infect them with the virus of doubt—“Maybe my experience isn’t as good as I thought, maybe it could be better”—then you prime them for your solution. You get them angry about how it works now so they can get excited about a new way of doing things. Steve was a master of this. Before he told you what a product did, he always took the time to explain why you needed it. And he made it all look so natural, so easy.

It never felt like a speech. It felt like a conversation. Like a story. And the reason is simple: Steve didn’t just read a script for the presentation. He’d been telling a version of that same story every single day for months and months during development—to us, to his friends, his family. He was constantly working on it, refining it. Every time he’d get a puzzled look or a request for clarification from his unwitting early audience, he’d sand it down, tweak it slightly, until it was perfectly polished. It was the story of the product. And it drove what we built.

Your product’s story is its design, its features, images and videos, quotes from customers, tips from reviewers, conversations with support agents. It’s the sum of what people see and feel about this thing that you’ve created.

And it all starts with “why.” Why does this thing need to exist? Why does it matter? Why will people need it? Why will they love it?

And you have to hold on to that “why” even as you build the “what”—the features, the innovation, the answer to all your customers’ problems. Because the longer you work on something, the more the “what” takes over—the “why” becomes so obvious, a feeling in your gut, a part of everything you do,…

So you need to pause and clearly articulate the “why” before you can convince anyone to…

There’s a competition for market share and a competition for mind share. If your competitors are telling better stories than you, if they’re playing the game and you’re not, then it doesn’t matter if their product is worse. They will get the attention. To any customers, investors, partners, or talent doing a cursory search, they will appear to be the leaders in the category. The…

So you have to find an opportunity to craft stories that stick with customers and keep them talking about you. Even if your customer knows you and your product, or they’re highly technical, there are frictions that you can eliminate for them. You can explain why they need one version of lubricant over the other or give them information they never had before. Or you explain why buying the same product from your company is better than buying that product from a competitor. You can earn their trust by showing that you really know your stuff or understand their needs. Or offer them something useful;…

A good story is an act of empathy. It recognizes the needs of its audience. And it blends facts and feelings so the customer gets enough of both. First you need enough insights and concrete information that your argument doesn’t feel too floaty and insubstantial. It doesn’t have to be definitive data, but there has to be enough to feel meaty, to convince people that you’re anchored in real facts. But you can overdo it—if your story is only informational, then it’s entirely possible…

So you have to appeal to their emotions—connect with something they care about. Their worries, their fears. Or show them a compelling vision of the future: give a human example. Walk through how a real person will experience this product—their day, their family, their work, the change they’ll experience. Just don’t lean so far into…

Every person is different. And everyone will read your story differently. That’s why analogies can be such a useful tool in storytelling. They create a shorthand for complicated concepts—a bridge directly to a common experience.

That’s another thing I learned from Steve Jobs. He’d always say that analogies give customers superpowers. A great analogy allows a customer to instantly grasp a difficult feature and then describe that feature to others. That’s why “1,000 songs in your pocket” was so powerful. Everyone had CDs and tapes in bulky players that only let you listen to 10–15 songs, one album at a time. So “1,000 songs in your pocket” was an incredible contrast—it let people visualize this intangible thing—all the music they loved all together in one place, easy to find, easy to hold—and gave them a way to tell their friends and family why this new iPod thing was so cool.

Evolution Versus Disruption Versus Execution Evolution: A small, incremental step to make something better. Disruption: A fork on the evolutionary tree—something fundamentally new that changes the status quo, usually by taking a novel or revolutionary approach to an old problem. Execution: Actually doing what you’ve promised to do and doing it well. Your version one (V1) product should be disruptive, not evolutionary. But disruption alone will not guarantee success—you can’t ignore the fundamentals of execution because you think all you need is a brilliant disruption. And even if you do execute your idea well, it may not be enough. If you’re revolutionizing a major, dug-in industry, you may also need to disrupt marketing or channel or manufacturing or logistics or the business model or something else that never occurred to you. Assuming V1 was at least a critical success, the second version of your product is typically an evolution of your first. Refine what you made in V1 using data and insights from actual customers and double down on your original disruption. The execution should step up a notch—now you know what you’re doing and should be able to provide a significantly more functional product. You can continue evolving that product for a while, but always seek out new ways to disrupt yourself. You can’t only start thinking about it when the competition threatens to catch up or your business begins to stagnate.

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.

Disruption should be important for you personally—who doesn’t want to do something exciting and meaningful?—but it’s also important for the health of your business. If you’ve truly made something disruptive, your competition probably won’t be able to replicate it quickly.

If your company is disruptive, you have to be prepared for strong reactions and stronger emotions. Some people will absolutely love what you’ve made. Some people will violently, relentlessly hate it. That’s the danger with disruption. It is not welcome by everyone. Disruption makes enemies.

But that’s the tricky thing with disruptions—they’re an extremely delicate balancing act. When they fall apart it’s usually for one of three reasons: You focus on making one amazing thing but forget that it has to be part of a single, fluid experience. [See also: Figure 3.1.1, in Chapter 3.1.] So you ignore the million little details that aren’t as exciting to build—especially for V1—and end up with a neat little demo that doesn’t actually fit into anyone’s life. Conversely, you start with a disruptive vision but set it aside because the technology is too difficult or too costly or doesn’t work well enough. So you execute beautifully on everything else but the one thing that would have differentiated your product withers away. Or you change too many things too fast and regular people can’t recognize or understand what you’ve made. That’s one of the (many) issues that befell Google Glass. The look, the technology—it was all so new that people had no idea what to do with it. There was no intuitive understanding of what the thing was for. It’s as if Tesla decided out the gate to build electric cars with five wheels and two steering wheels. You can change the motor, change the dash—but it still has to look like a car. You can’t push people too far outside their mental model. Not at first.

When you’re evolving you need to understand the quintessential things that define your product. What’s key to your feature set and your branding? What have you trained the customer to look for? With the iPod it was the click wheel. With the Nest Learning Thermostat it was the round, clean screen with a big temperature in the middle. To maintain the core of your product there are usually one or two things that have to stay still while everything else spins and changes around them. And that’s a useful constraint. You need some constraints to force you to dig deep and get creative, to push envelopes you hadn’t thought to open before.

So either the landscape was going to change under our feet, or we were going to change the landscape. We had to disrupt ourselves.

Competition is a given, both direct and indirect. Someone is always watching, trying to exploit any crack in a more successful competitor.

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.

The tools you need to make those decisions are below, organized by order of importance: 1. Vision: Know what you want to make, why you’re making it, who it’s for, and why people will buy it. You’ll need a strong leader or a small group to ensure the vision is delivered intact. 2. Customer insights: This is what you’ve learned through customer or market research or simply by thinking like your customer: what they like, what they dislike, what problems they experience on a regular basis, and what solutions they’ll respond to. 3. Data: For any really new product, reliable data will be limited or nonexistent. That doesn’t mean you shouldn’t make a reasonable attempt to gather objective information—the scope of the opportunity, the way people use current solutions, etc. But this information will never be definitive. It won’t make your decisions for you.

Once you start iterating on an existing product, V2, your second adventure, you’ll have experience and customers and the luxury of plenty of data-driven decisions. However, a myopic focus on numbers can slow you down or lead you off-track. So you’ll still need all the same tools as above, just in a different order. 1. Data: You’ll be able to track how customers use your current product and test new versions. You can confirm or disprove hunches with hard data from actual paying customers. This data will allow you to fix the stuff you screwed up when you were just following your gut. 2. Customer insights: Once people have committed to paying money for your product, they’re much more reliable for useful insights. They can tell you what’s broken and what they want to see next. 3. Vision: Assuming you got 1.0 more or less right, that original vision moves behind the data and insights you can get from actual customers. But your original vision should not be set aside entirely as you iterate. You should always keep in mind your longer-term goals and mission so that your product’s fundamental purpose doesn’t get lost.

You should also keep in mind that you’re not just making V1 or V2 of your product—you’re building out the first or second version of your team and processes. V1 team: It’s mostly or all new players working together. You’re still feeling each other out, trying to understand if you can trust each other and who will stick around when things get hard. You’ll need to agree on a singular process, which is often harder than agreeing on a product. People will disagree based on past experiences and trust can quickly break down. The risk of making something new is always compounded by not having confidence in the team. V2 team: You may have to upgrade parts of your team as you become more ambitious, but many of the same teammates who weathered the storm of V1 will be ready to enter the fray again for V2. You’ll hopefully trust each other,…

But you don’t have to figure out your vision all by yourself. In fact, you probably shouldn’t. Locking yourself alone in a room to create a manifesto of your single, luminous vision looks and feels indistinguishable from completely losing your mind. Get at least one person—but preferably a small group—to bounce ideas off of. Sketch out your mission together. Then fulfill it together.

be driven by glorious, simple, clear-cut, black-and-white data. But before that moment comes you need to get through the sprint and the marathon of V1. You need people you trust to keep you going. And you’ll need to know when to stop. If you wait for your product to be perfect, you will never finish. But it’s very hard to know when you’re done—when you need to stop building and just put it out into the world. When is it good enough? When are you close enough to your vision? When are the inevitable issues ignorable enough that you can live with them? Typically your vision is so much greater than what materializes in V1. There’s always another revision, always something else you want to do, change, add, tweak. When do you tear yourself away from what you’re making and just … stop? Ship it. Set it free. See what happens. Here’s the trick: write a press release. But don’t write it when you’re done. Write it when you start.

If you launched right now, could you more or less send that press release into the world and have it be mostly true? If the answer is yes, then congratulations: your product is probably ready, or at least pretty close. You have achieved the core of your vision. Everything else is most likely a “nice to have,” not a priority. Of course, there’s a chance that since you started, you’ve had to pivot so much that the original press release is laughably off-base. Sometimes that happens. No problem. Write another press release. Rinse. Repeat. This is an adventure and adventures never go according to plan. That’s what makes them fun. And scary. And worth doing. That’s why you take a deep breath, surround yourself with great people, and head out into the wilderness.

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. When you handcuff yourself to a deadline—ideally an external, immovable date like Christmas or a big conference—you have to execute and get creative to finish on time. The external heartbeat, the constraint, drives the creativity, which fuels the innovation. Before you launch V1, your external deadline is always a little wobbly. There are too many unknown unknowns to write it in stone. So the way you keep everyone moving is by creating strong internal deadlines—heartbeats that your team sets their calendar to: 1. Team heartbeats: Each individual team makes its own rhythm and deadlines for delivering their piece of the puzzle. Then all the teams align for … 2. Project heartbeats: These are the moments when different teams sync to make sure the product still makes sense and all the pieces are moving at the right pace.

But that’s always the crisis of V1: when do you launch? You don’t have any customers, you haven’t really told the world what you’re working on. It’s all too easy to just keep working. So you have to force yourself to stop. Construct a deadline and handcuff yourself to it.

We forced as many constraints on ourselves as possible: not too much time, not too much money, and not too many people on the team. That last point is important.

Don’t go crazy hiring people just because you can. With most projects in the concepting stage, you can get a huge amount done with around ten people or even fewer. You don’t want to staff up and then be forced to design by committee or put a ton of people on the sidelines, sitting on their hands, waiting for you to figure it out.

So 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. Of course, there are things that take longer—research can take decades, for example. But even if it takes ten years to research a question, regular check-ins along the way ensure you’re still chasing the right answer. Or still asking the right question. Every project needs a heartbeat. Pre-V1 launch, that heartbeat is entirely internal. You’re not talking to the outside world yet, so you have to have a strong internal rhythm that pushes you toward a set launch date. This rhythm is made of major milestones—board meetings, all-hands meetings, or project milestones at certain moments of product development where everyone, engineering and marketing and sales and support, can pause and sync with each other. This might happen every few weeks or every few months, but it has to happen in order to keep everyone moving in lockstep to the external announcement.

It seemed perfectly sensible. We nodded in approval at the consultants. Great! We have a real schedule! We might actually pull this off! Until we realized that: Nobody can accurately estimate their time or all the steps they’ll need to perform. Trying to get into that much detail that far out is useless. Something will always spoil your plan. We were spending all our time scheduling, arguing over what could and couldn’t be done in a half day, and it was impossible to see the whole forest through the half trees.

After a few months, we scrapped the whole system. No more half days. We organized our time into bigger chunks—weeks, months. We started taking a macro view of our projects. And that enabled us to build the V1 of Velo in about eighteen months. Then we handed it, gleaming and new, to sales and marketing. And they had absolutely no idea what to do with it. They’d never seen it before. They didn’t know how to sell it, where to sell it, how to advertise it. They had been an afterthought to us, and now we were an afterthought to them. We had figured out our internal heartbeat, but had never synced it with any other team. Nobody else could keep up with our rhythm. We were dancing to our own beat, sure that all eyes were on us, and our dance partner was across the room getting punch, thinking about electric shavers. We needed internal milestones within the project—regular check-ins where we would make sure everybody understood how the product had evolved and could evolve their side of the business along with it. And to make sure the product still made sense. To see if marketing still liked it. To see if sales still liked it. To see if support could still explain it. To make sure everyone knew what they were making and the plan to launch it. Those milestones slow you down in the short term, but ultimately speed up all of product development. And they make for a better product.

Heartbeats shouldn’t be too fast. 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.

You need natural pauses so people can catch up to you—so customers and reviewers can give you feedback that you can then integrate into the next version. And so your team can understand what the customer doesn’t.

So look at the year ahead. After you’ve launched your V1, then two to four times in that year, you should be announcing something to the world. New products, new features, new redesigns or updates. Something meaty that’s worth people’s attention. It doesn’t matter if you’re a big or tiny company; if you’re building hardware or apps, B2B or B2C, this is the right rhythm for customers. For humans.

So have at least one really big launch and another one to three smaller launches every year.

Predictability allows your team to know when they should be heads down working and when they should be looking up to check in with other teams or to make sure that they’re still headed in the right direction. [See also: Chapter 1.4: Don’t (Only) Look Down.] Predictability allows you to codify a product development process rather than starting from scratch every time. It allows you to create a living document with checkpoints, milestones, schedules, and plans that trains new employees and teaches everyone: This is how we do it. This is the framework for how to build a product.

Three Generations The joke is that it takes twenty years to make an overnight success. In business, it’s more like six to ten. It always takes longer than you think to find product/market fit, to get your customers’ attention, to build a complete solution, and then to make money. You typically need to create at least three generations of any new, disruptive product before you get it right and turn a profit. This is true for B2B and B2C, for companies that build with atoms or electrons or both, for brand-new startups and brand-new products. Keep in mind there are three stages of profitability: 1. Not remotely profitable: With the first version of a product you’re still testing out the market, testing out the product, trying to find your customers. Many products and companies die at this stage before they ever make a dime. 2. Making unit economics or gross margins: Hopefully with V2 you can make a gross profit with each product sold or each customer who subscribes to your service. Keep in mind that fantastic unit economics are not enough to make a profitable company. You’ll still be spending a ton of money just running your business and acquiring customers through sales and marketing. 3. Making business economics or net margins: With V3 you have the potential to make net profits with each subscription or product sold. That means that what you take in in sales revenue outstrips your business costs, so your company as a whole makes money. The reason it takes so long to reach gross margins and even longer to make net margins is that learning takes time. For your company and your customers. Your team will have to 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.

After companies find product/market fit, they can start to focus on profitability. Businesses that build with atoms are focused on COGS—cost of goods sold. Aside from direct labor, the main thing they spend money on is actually making the product. So they need to lower the cost of producing their product in order to reach profitability.

Companies that build with electrons are focused on CAC—customer acquisition costs. Aside from direct labor, their money gets spent selling and supporting their product.

Companies that build with both atoms and electrons have to worry about COGS and CAC, but generally should focus on one at a time. First knock out COGS, then move on to CAC. Build the product, then add the services.

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.

They demanded to be shown ahead of time that the unit and business economics of the product were sound. But that was impossible.

So when we started work on the Nest Protect smoke and CO alarm, our second product, you’d think it would be easier. That everything we’d built already would let us skip a few steps. But the second you start a new product, you have to hit the restart button—even if you’re at a big company. Sometimes it’s even harder the second time around because all the infrastructure that’s been built up for the first product gets in the way. So you’ll still need to go through at least three generations before you get it right. You make the product. You fix the product. You build the business. You make the product. You fix the product. You build the business. You make the product. You fix the product. You build the business. Every product. Every company. Every time.

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.” [See also: Chapter 3.2: Why Storytelling.] 2. It solves a problem that a lot of people have in their daily lives. 3. It follows you around. Even after you research and learn about it and try it out and realize how hard it’ll be to get it right, you can’t stop thinking about it.

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.

The best ideas are painkillers, not vitamins. Vitamin pills are good for you, but they’re not essential. You can skip your morning vitamin for a day, a month, a lifetime and never notice the difference. But you’ll notice real quick if you forget a painkiller. Painkillers eliminate something that’s constantly bothering you. A regular irritation you can’t get rid of. And the best pain—so to speak—is one you experience in your own life. 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.

Eventually, each of those risks became a rallying cry for the team—instead of avoiding them, we embraced them. We continually said to ourselves, “If it were easy, everyone else would be doing it!” We were innovating. The risks and our ability to solve for them was what set us apart. We would do something nobody else thought possible. That’s ultimately what made this company worth starting.

The world is full of people who have an idea and want to start a company. Often they ask me if they’re ready. Do I have what it takes to create a successful startup? Should I launch my project within a big company instead? The answer is that you’ll never know until you take the leap and try. But here’s how to get as ready as you’ll ever be: 1. Work at a startup. 2. Work at a big company. 3. Get a mentor to help you navigate it all. 4. Find a cofounder to balance you out and share the load. 5. Convince people to join you. Your founding team should be anchored by seed crystals—great people who bring in more great people.

What does an org chart look like? What is sales? How should marketing work? What about HR, finance, legal?

the unknown unknowns that keep you up at night should be focused on the problem you’re trying to solve, not on whether to get a marketing agency or what kind of lawyer to hire. You won’t have time to screw up the basics, to waste time learning the fundamentals.

Of course, that doesn’t mean that you shouldn’t consult with anyone. Doing it alone is impossible. You’re going to need a mentor or a coach. You’re going to need an incredible founding team. And you’ll probably need a cofounder.

But be careful—even if you have a cofounder, there can only be one CEO. And if you pile on the cofounders, you’re asking for trouble. Having two founders works well. Three can work sometimes. I’ve never seen it work with more.

Sharing the load is one thing; unloading it altogether is another. If you’re going to lead a team, you need to be ready to lead.

When you close your eyes, you should already know exactly who your first employees will be. You should be able to write down a list of five names without a second thought. If you don’t have that list of names ready before you start, you probably shouldn’t be starting.

Titles, pay, and perks should never be your main draw, but that doesn’t mean you should be cheap. Try to be reasonably flexible and structure compensation so it fits the individuals you’re hiring. Some people may prefer cash over equity and that should always be an option. But most of your team should get generous equity packages—they are owners of the idea, too, so they should also be owners of the company. You want your team to have a vested interest in your success so when things go wrong—and they definitely will—those people will stick with you.

Seed crystals are people who are so good and so well loved that they can almost single-handedly build large parts of your org. Typically they’re experienced leaders, either managers of large teams or super-ICs who everyone listens to. Once they’re in, a tidal wave of other awesome people will typically follow.

That’s what you need when you’re going to start a company or start a huge new project—a coach. A mentor. A source of wisdom and aid. Someone who can recognize a brewing problem and warn you about it before it happens. And someone who will quietly inform you that it’s dark right now because your head is jammed up your own ass, and who will give you a few tips to quickly remove it. You can make do without a cofounder. You can survive for a while without a team. But you can’t make it without a mentor.

Find at least one person who you deeply trust and who believes in you. Not a life coach or an executive leadership consultant, not an agency, not someone who’s read a lot of case studies and is ready to charge you by the hour. And not your parents—they love you too much to be impartial. Find an operational, smart, useful mentor who has done it before, who likes you and wants to help.

So do the work. Know what you’re getting into. Trust your gut. And when the time comes, you’ll be ready.

And the rules for every successful human relationship are the same: before you can jump headfirst into a major life-changing commitment, you need to get to know each other. Trust each other. Understand each other.

The first question you should ask yourself is the most basic one: does your business actually need outside money right now? For many early pre-seed-stage startups, the answer is “no” surprisingly often. If you’re still researching, still testing things out, making sure your idea has legs, then you don’t need to immediately leap to financing. Take your time. Get comfortable with delayed intuition.

If you do think you’re ready to take money, then what exactly do you plan to use that money for? Do you need to build a prototype? Recruit a team? Research an idea? Get a patent? Petition local government? Fuel a partnership? Create a marketing campaign? What’s the minimum amount necessary to meet your needs now, and how much will you require later as those needs change?

Remember, once you take money from an investor, you’re stuck with them. And the balance of power shifts. A VC can fire a founder, but a founder can’t fire their VC. You can’t divorce them for irreconcilable differences.

Just don’t forget the other factor that can sneak up and kick your ass: time. It will take longer than you think to get funding. Expect it to be a 3–5 month process. It may end up being faster than that—especially in a founder-friendly environment—but I wouldn’t gamble on it. Too many companies wait until they’re about to run out of money, then hit an air gap and are near bankruptcy before desperately grabbing whatever funding they can get. Always start the pitching process when you don’t actually need money. You want to be in a position of strength, not buckling under the pressure and making bad choices. You should also remember to watch out for the holidays—August, Chinese New Year, Thanksgiving through New Year. People forget that VCs take vacations, too.

The best thing about angel investors is that they aren’t beholden to LPs. They simply believe in you. They want to help you. And there’s nobody looming over their head demanding an immediate profit. Angel investors are typically much more willing to take a risk, so they may fund you earlier than a VC would and give you much more leeway and time to figure out your company without pushing nearly as hard.

Fifty percent of marriages fail, but 80 percent of startups do. If you start a company, the odds are against you. So you’ll need to get over the mental anguish of failure and losing other people’s money. If and when the time comes, you’ll have to be honest and open about it; you’ll have to admit what went wrong and how you learned from it.

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.

You Can Only Have One Customer Regardless of whether your company is business-to-business (B2B) or business-to-consumer (B2C) or business-to-business-to-consumer (B2B2C) or consumer-to-business-to-consumer (C2B2C) or some-yet-unimagined acronym, you can only serve one master. You can only have one customer. The bulk of your focus and the whole of your branding should be for consumers or business—not both. Understanding your customer—their demographics and psychographics, their wants and needs and pain points—is the foundation of your company. Your product, team, culture, sales, marketing, support, pricing—everything is shaped by that understanding. For the vast majority of businesses, losing sight of the main customer you’re building for is the beginning of the end.

Steve Jobs was clear about the lesson he’d learned and made sure we all learned it, too: any company that tries to do both B2B and B2C will fail.

Is your customer Jim the Millennial, who saw your ad on Instagram then bought your product as a Christmas present for his sister? Or is it Jane the CIO of a Fortune 500 company who answered a cold email from your sales team, negotiated pricing and different product features for months, and now needs a team of customer success agents to train the five thousand employees under her? You cannot hold both those people in your head at the same time. You cannot make a single product for two completely opposite customers—for two different customer journeys. Not when you’re making technology. Or services. Or a store. Not even if you’re making dinner. It’s a hard rule.

That’s the thing to remember about B2B2C—it doesn’t matter how many businesses are involved: ultimately it’s the end consumer who carries the business model on their back.

But that story can end badly. When attention and focus shift away from the consumer and toward the businesses bringing in the real money, companies go down some very dark alleys. And it’s always the consumers who suffer. So do not lose your focus. 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.

There are two kinds of work/life balance: 1. True work/life balance: A magical, quasi-mythical state where you have time for everything: work, family, hobbies, seeing friends, exercising, vacationing. Work is just one part of your life that doesn’t intrude on any other part. This kind of balance is impossible when you’re starting a company, leading a team that’s trying to create innovative products or services on a competitive timeline, or just experiencing crunch time at work. 2. Personal balance when you’re working: Knowing you’re going to be working or thinking about work most of the time and creating space to give your brain and body a break. To reach some level of personal balance, you need to design your schedule so you have time to eat well (hopefully with family and friends), exercise or meditate, sleep, and briefly think about something other than the current crisis at the office. To withstand a complete lack of true work/life balance requires a clear organizational strategy. You need to prioritize. It’s important to have everything you need to think about written down and have a plan for when and how you’ll bring it up with your team. Otherwise it will swirl around in your brain endlessly, killing any meager chance you have of relaxing your shoulders for a minute.

Here’s my advice: do not vacation like Steve Jobs. Steve would typically take two weeks off, twice a year. We’d always dread those vacations at Apple. The first forty-eight hours were quiet. After that it would be a storm of nonstop calls.

And sometimes that’s okay. Really. Sometimes it’s your only option. But there’s a world of difference between racking your brain, ruminating all night about a work crisis, versus letting yourself think about work in an unstructured, creative way. The latter gives your brain the freedom to stop hammering away at the same problems with the same worn-down tools. Instead, you let your mind rummage around to find new ones.

Humans cannot survive on stress and Diet Coke alone.

Everyone thought I was crazy—and many still do—but here’s what I did: I took several sheets of paper with me everywhere. They had all the top milestones in front of us for each of the disciplines—engineering, HR, finance, legal, marketing, facilities, etc.—and everything we needed to do to reach those milestones. Every top-level question that I had was on those papers. So when I was in a meeting or talking to someone, I could quickly scan it. What are my top issues? What issues do our customers have? What’s the current roadblock for this person’s team? What are the next major milestones? What date commitments did our teams make? And then there was the best part—the ideas. Whenever someone had a great idea that we had to table for the moment—an improvement to the product or the organization—I’d write it down. So right next to the list of that week’s to-dos and tasks, there was a working library of all the things we couldn’t wait to begin. I’d regularly read them to myself and see if they still applied. It kept me inspired and excited and focused on the future. And it was great for the team. They saw that I paid attention to their ideas and made sure we kept thinking about them. The only way for me to capture all of it—good ideas, priorities, roadblocks, the dates that people promised to deliver, and the major internal and external heartbeats ahead—was to take notes in every meeting. Longhand. Not on a computer.

The act of using a pen, then retyping and editing later, forced me to process information differently.

Every Sunday evening, I would go through my notes, reassess and reprioritize all my tasks, rifle through the good ideas, then update those papers on a computer and print out a new version for the week. Continually reprioritizing allowed me to zoom out and see what could be combined or eliminated. It let me spot moments when we were trying to do too much.

I was forced to prioritize based on what really mattered, as opposed to what was just top of mind. That let me keep my eye on the bigger goals and milestones ahead of us, not just the fires at our feet or whatever feature we were most excited about that day. Then Sunday night I’d email the whole list out to my management team. Each item had a name attached to it. Everyone could look at the top of the list to see what I’d be focused on that week, what they were accountable for, and what the next major milestones were. And every Monday, we’d have a meeting about it. Everyone hated it. I literally watched people flinch when I’d bring out the papers, scanning them for the thing I’d been asking about for weeks. That thing I’d refuse to forget about because it hadn’t gotten crossed off the list yet. On June 3 you said it would be ready by the end of the month. It’s now July—what’s the status of this project? It wasn’t micromanagement. It was holding people accountable. It was holding everything in my head at the same time. It was holding on for dear life amid the flood of everything I needed to remember.

I’m not saying this will work for everyone. Far from it. Everyone needs to find their own system. But you do need to prioritize your tasks, manage and organize your thoughts, and create a predictable schedule for your team to access those thoughts. And then you need to take a break.

Every time I left, I’d hand the reins over to a different person who reported to me. It’s your problem now, buddy! It was a time for the team to step up and learn to do what I did. Vacations are a great way to build a team’s future capabilities and see who might step into your shoes in the years to come. Everyone thinks they can do your job better—until they actually have to do it and deliver. So even if you’re in a high-stress job, you need to take vacations. They’re important for your team.

So look at your calendar. Engineer it. Design it. Lay out the next three to six months on paper. Write down what a typical day looks like. And what a typical week or two weeks look like. Keep going for the next month. And then the next six.

You want someone who learns fast, only needs to be told once, and who, over time, can anticipate your needs and fix problems before they ever hit your desk.

None of this is revolutionary. You probably learned it in elementary school: write down a list of what you need to do, take a deep breath and some quiet time if you’re upset, eat your vegetables, exercise, sleep. But you’ll forget. We all forget. So grab your calendar and make a plan. You’ll be working all the time for a while. That’s okay. It’s not forever. But you’ve probably been beating at your problems with the same hammer for too long—it’s time for your brain to rummage around and find a crowbar. Or a bulldozer. Give your mind some time to breathe. Then put away your phone before bed. And maybe do some yoga.

Crisis You will encounter a crisis eventually. Everyone does. If you don’t, you’re not doing anything important or pushing any boundaries. When you’re creating something disruptive and new, you will at some point be blindsided by a complete disaster. It may be an external crisis that you have no control over, or an internal screwup or just the kinds of growing pains that hit every company. [See also: Chapter 5.2: Breakpoints.] Either way, when the time comes, here’s the basic playbook: 1. Keep your focus on how to fix the problem, not who to blame. That will come later and is far too distracting early on. 2. As a leader, you’ll have to get into the weeds. Don’t be worried about micromanagement—as the crisis unfolds your job is to tell people what to do and how to do it. However, very quickly after everyone has calmed down and gotten to work, let them do their jobs without you breathing down their necks. 3. Get advice. From mentors, investors, your board, or anyone else you know who’s gone through something similar. Don’t try to solve your problems alone. 4. Your job once people get over the initial shock will be constant communication. You need to talktalktalk (with your team, the rest of the company, the board, investors, and potentially press and customers) and listenlistenlisten (hear what your team is worried about and the issues that are bubbling up, calm down panicked employees and stressed-out PR people). Don’t worry about overcommunicating. 5. It doesn’t matter if the crisis was caused by your mistake or your team or a fluke accident: accept responsibility for how it has affected customers and apologize.

If you’re an individual contributor, you need to take your marching orders and start marching. Do your core job while continuing to look for and suggest other options to solve the issue. Try not to speculate or gossip. If you have concerns or suspicions, report them up the chain, then get back to work. If you’re a manager, you need to relay information from leadership without overwhelming or distracting your team. Check in with the team a couple of times a day—try not to harass them more than that (hourly messages just freak everyone out). You need to be there for them, not just to ensure that the work is getting done, but also to make sure they’re okay. You’re the first line of defense against burnout. The pressure, stress, red-eyes, and bad food in the middle of the night will get to people. You may need to give everyone a break—even during a crisis. Remember to set expectations and limits. You’ll probably have to work over the weekend. Okay. That happens. But tell your team what the plan is: we’ll work hard on Saturday but everyone needs to get out of the office at 5 p.m. and then we’ll have a check-in on Sunday night. If you’re the leader of a broader group or company, you probably spent years of your life unlearning the tendencies of micromanagement. Well, if you’re in a crisis then it’s time to be a micromanager again.

That’s what I said over and over at Nest. It became like a mantra: We’ll get through this. We’ve done it before. Here’s the plan. We’ll get through this. We’ve done it before. Here’s the plan.

And it worked. Nest Protect and our brand survived. There is always a temptation to obfuscate or couch everything in legalese—to say “mistakes were made” but never admit they were yours. This will not work. People will figure it out. And they will be pissed. 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 whenever you see the water rising, talk to your mentor. Or your board. Or your investors. It’s your responsibility as a leader not to try to deal with a disaster on your own. Don’t lock yourself in a room, alone, frantically trying to fix it. Don’t hide. Don’t disappear. Don’t imagine that by working for a week straight and not sleeping you can solve the problem yourself and nobody ever has to know. Get advice. Take deep breaths. Make a plan. Then put on your rain boots and walk into the tidal wave.

Hiring A near-perfect team is made up of smart, passionate, imperfect people who complement one another. As that team grows beyond ten, twenty, fifty people, you’ll need: »  Eager new grads and interns to learn from your experienced, well-seasoned crew. Every young person you spend time training is an investment in the long-term health of your company. »  A defined hiring process that ensures that candidates interview with people from across the company who they’ll work with directly. »  A thoughtful approach to growth to avoid watering down your culture. »  Processes that ensure new employees are immersed in and build on your culture from day one. »  A way to keep HR and hiring top of mind for your leadership team and the management teams under them. It should be the first topic of business in every team meeting. You’ll also need to fire people. Don’t be scared of it, but don’t be callous, either. Give people plenty of warning and opportunity to course correct, follow the letter of the law, then bite the bullet and help them find a better opportunity.

The best teams are multigenerational—Nest employed twenty-year-olds and seventy-year-olds. Experienced people have a wealth of wisdom that they can pass on to the next generation and young people can push back against long-held assumptions. They can often see the opportunity that lies in accomplishing difficult things, while experienced people see only the difficulty.

Someone took a risk on you once. Someone guided you through your mistakes, took the time to help you grow. Not only is it your duty to create that moment for the next generation, but it’s also a good investment in the long-term success of your company. Out of every ten interns we brought on each year, one to three would get offers to return again next summer or would just be hired full-time.

It is a battle to find amazing talent. You cannot afford to ignore any part of the population when you’re trying to grow your team—there are pools of outstanding young and old and female and male and trans and nonbinary and Black and Latino and Asian and Southeast Asian and Middle Eastern and European and Indigenous people in the world who can have a profound impact on your company. Different people think differently and every new perspective, background, and experience you bring into the business improves the business. It deepens your understanding of your customers. It illuminates part of the world that you were blind to before. It creates opportunities.

That was the system we had at Nest. We called it the Three Crowns. Here’s how it worked: Crown 1 was the hiring manager. They got the role approved and found the candidates. Crowns 2 and 3 were managers of the candidate’s internal customers. They picked one or two people from their team to interview the candidate. Feedback was collected, shared, and discussed, then the Three Crowns met to decide who to hire. Matt or I would watch over it all and make the final call in the rare instance when the Crowns couldn’t agree. Typically the answer if we had to get involved was no, thank you: PASS.

Once you assess someone thoroughly, check references, and decide to hire them—you also have to decide to trust them. You can’t start with zero trust and expect someone to prove themselves to you.

In an interview I’m always most interested in three basic things: who they are, what they’ve done, and why they did it. I usually start with the most important questions: “What are you curious about? What do you want to learn?”

Another good interview technique is to simulate work—instead of asking them how they work, just work with them. Pick a problem and try to solve it together. Choose a subject that both of you are familiar with but neither is an expert in—if you pick a problem in their domain they’ll always sound smart; pick a problem in yours and you’ll always know better. But the subject doesn’t matter nearly as much as the process of watching them think. Get on the whiteboard, draw it out. What kinds of questions do they ask? What approaches do they suggest? Do they ask about the customer? Do they seem empathetic or oblivious? You’re not just interviewing to see if a person can do the job required of them today. You’re trying to understand if they have the innate tools to think through the problems and jobs you don’t see coming yet—the jobs they can grow into tomorrow.

The best way to share and embed cultural DNA is person to person.

Many people rose to the challenge. Many exceeded all expectations. And some didn’t. Sometimes it will turn out that the people you hired early aren’t right for the team as you grow. Or sometimes you hired the wrong people right out of the gate. Or you hired mediocre people. Or you hired people who weren’t a good fit for your culture, despite being spectacular otherwise. Sometimes you hire people who just won’t be successful at your company. And then you need to fire them.

But it’s important to remember that while the moment of conflict is always miserable, that moment is brief and it’s your job not to fixate on it, not to dwell in it for too long. You have to quickly move from “this isn’t working” to “now I’m going to do everything I can to help you find a job you like that’s better for you.” It’s counterintuitive, but firing someone from a job they’re failing at and utterly unsuited to can be a surprisingly positive experience. I’ve never fired someone where it didn’t end up being better for both them and the company.

Under normal circumstances nobody should ever be shocked that they’re getting fired or have to ask why it’s happening. They may not agree, of course. But anyone who’s struggling should be having weekly or twice-monthly 1:1 meetings about that struggle. That’s where issues are honestly discussed, solutions are attempted, and there’s a follow-up about what worked and what didn’t and what’s going to happen next. Just as people make a commitment to your company when they join it, you make a commitment to them. If you’re leading a company or a large org, it is your responsibility to help people identify their challenge areas and give them space and coaching to get better or help them to find a spot at the company where they can be successful.

By far the hardest part of growth is finding the best people—in all their different incarnations—trusting your team to hire them, then making sure they’re happy and thriving.

Every Monday morning at Nest, that’s how my management meetings started: Who are the great people we want to hire? Are we making our hiring goals or retention metrics? If not, what’s the problem? What are the roadblocks? And how is the team doing? What issues do people have? How are performance reviews going? Who needs a bonus? How are we going to celebrate these accomplishments so the team feels valued? And, most importantly, are people leaving? Why? How are we going to make this job more meaningful and fulfilling and exciting than anything else out there? How are we going to help our people grow? Only after we got through this important subject could we move on to anything else—like what the hell we were building. The managers on the team saw it was important to me, so that’s how they started structuring their weekly meetings with their teams. It became the Nest way. People first. Always. What you’re building never matters as much as who you’re building it with.

The cake is a microcosm of the larger problems of growth, but I’m also speaking literally. Turns out people get weirdly defensive about cake. It’s always a mini-crisis when you have to stop having all-company birthday parties for individual employees.

If you can see it coming, you can design your future.

You’ll need to break your org into product specific groups so that each product gets the attention it deserves. This team works on the thermostat, this team works on the smoke alarm. And then you might have to subdivide again. At Nest we ended up creating a team for accessories; otherwise they’d have never gotten made. The mainline team would always say they’d get to it but the accessories projects were never their first priority, so they’d inevitably prioritize other things.

Each product family gets a dedicated engineering team, a dedicated marketing person, a dedicated designer and writer. And that turns them into little startups inside the business—smaller, faster, more autonomous. Decisions speed up and everyone shares one clear goal rather than scrambling for resources on a side project.

They tried something and failed, and that means they learned. That’s okay. Life is the process of elimination and now they’re free to try something new.

All-hands meetings are a great example. These are meetings that everyone in the company attends. In the beginning, when you have fewer than 40–50 people, they probably happen weekly or every other week. They start out as informal and super-tactical gatherings. For the next hour we’re going to sit on the floor, share some lemon bars, discuss what everyone needs to know this week to do their jobs, address the next milestone, talk about what fun stuff we’re doing, and check out the competition. Sometimes, if necessary, you deliver hard news. But usually you’re looking forward—you talk about the mission and your progress toward it, then there’s a bit of team building at the end.

So save the all-hands for when you really need them—make them special. Keep them regular but rare. And encourage smaller, inter-team groups to get together to share relevant information. They can even sit on the floor eating lemon bars. But the goals of the meetings should be crisp and clean, and the time people spend at work should have a purpose.

Coaching and mentorship is critical before breakpoints. Especially at the transition to 30–40 people, when managers emerge, and around 80–120, when you promote people to director. Just remember there’s a difference between coaches and mentors: Coaches are there to help with the business. It’s all about the work: this company, this job, this moment in time. Mentors are more personal. They don’t just help with people’s jobs, they help with their lives, their families. A coach helps because they know the company; a mentor helps because they know you. The best is a combination of the two—someone who understands both worlds—a mentor/coach who can help people see the bigger picture about what the business may need as well as what they need personally. In the early days, if you’re the leader, you’re the mentor. You prepare people for the big transition and coach them through it. But as the team grows, you’ll need to bring in formal mentors or coaches to help with some of the load. At 120 people, you should have executive coaches who can be there to guide your leadership team through their new responsibilities as well as communication and organizational strategies.

Culture arises organically but then needs to be codified to be maintained. So write down your company values and post them on your physical and virtual walls. Share them with new employees. Make them part of every interview with new candidates. Everyone should know what matters at your company—what defines your culture. If you don’t explicitly know your values, you can’t pass them on, maintain them, evolve them, or hire for them. And make every team write down how they do things: What’s the marketing process? What’s the engineering process? What are the phases for how we make a product? How do we work together? It can’t just be left in people’s brains. People leave. New people join. If you’re growing geometrically—in all directions at once—then you need a strong, stable core at the center. Your experienced employees have to be able to walk new employees through how you do what you do, or else everyone gets lost.

Planning for a breakpoint is a lot to deal with on top of everything else going on. And it’s the worst kind of planning: messy, difficult, infinitely annoying people stuff. It’s always tempting to leave it for another day. But “if it ain’t broke, don’t fix it” doesn’t work here. When you don’t prepare for breakpoints—don’t warn the team, don’t thoughtfully restructure the org around roles first and individuals second, don’t add new managers, don’t reassess your meetings and communication tools, don’t give people access to training or coaches, don’t actively work to preserve your culture—then the consequences are clear: In their quest to keep people happy, I’ve seen leaders build their org around existing employees instead of first figuring out what the optimal structure should be and fitting their team into those roles. Then roles and responsibilities overlap, there’s a ton of redundancy in the upper levels, they have to invent weird new titles for people, and nobody knows what they should be working on. Work slows to a crawl. Employees complain that the culture is dead. People start to quit. Panic sets in and it can feel like a full-blown crisis.

So when breakpoints come for you, remember how you’ve been reassuring the team and take your own advice: know they’re coming and get ready. Talk to your mentor. Understand what your job should look like well before every transition and plan for it. And always remember that 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.

Everything that needs to be created needs to be designed—not just products and marketing, but processes, experiences, organizations, forms, materials. 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. You may not be able to create a perfectly polished prototype without a professional designer, but you can get pretty damn far on your own if you follow two core principles: 1. Deploy design thinking: This is a well-known strategy originated by IDEO’s David Kelley that encourages you to identify your customer and their pain points, deeply understand the problem you’re trying to solve, and systematically uncover ways to solve it. [See also: Reading List: Creative Confidence: Unleashing the Creative Potential Within Us All.] For example, a person complains that they have too many TV remotes. Instead of immediately jumping in and combining all the remotes into one giant, ridiculously complicated remote, you should take time to understand your customer: What do they do when they sit down on the couch? What are they watching? When are they watching? Who’s watching with them? What do they use each remote for and how often? Where do they keep them? What happens when they grab the wrong one? From there, you come to understand your customer’s actual problem: they get home late and don’t want to switch on a bunch of lights and wake their family, so they try to turn on the TV in the dark and can never find the right remote. Okay—we can find a solution for that. 2. Avoid habituation: Everyone gets used to things. Life is full of tiny and enormous inconveniences that you no longer notice because your brain has simply accepted them as unchangeable reality and filtered them out. For example, think about the little sticker that grocery stores put on produce. Instead of just eating an apple, you now have to find the sticker, peel it off, and scrape the gluey residue off with a fingernail. The first few times you encountered the sticker, you were probably annoyed. By now you barely register it. But when you think like a designer, you stay awake to the many things in your work and life that can be better. You find opportunities to improve experiences that people long ago assumed would just always be terrible.

Especially because that way of thinking is infectious. I come across tons of startups that encounter a difficult design challenge and immediately think they have to hire someone else to solve it. We don’t know enough, we don’t have the expertise, we need someone to do this for us. But you shouldn’t outsource a problem before you try to solve it yourself, especially if solving that problem is core to the future of your business. If it’s a critical function, your team needs to build the muscle to understand the process and do it themselves.

You may not even need anyone to draw or make aesthetic choices. For example, take naming. It’s an issue all businesses face. But rather than calling in a naming or branding agency to pick a name for you, sit down and approach the problem like a designer: Who is your customer and where will they encounter this name? What are you trying to get your customer to think or feel about your product? What brand attributes or product features are most important to highlight with this name? Is this product part of a family of products or is it stand-alone? What will the next version be called? Should the name be evocative of a feeling or idea or a straightforward description? Once you come up with a list, begin to use the names in context. How does it work in a sentence? How do you use it in print? How do you use it graphically?

Then they’ll design the process from scratch, the way it should be designed: Ask why at every step—why is it like this now? How can it be better? Think like a user who has never tried this product before; dig into their mindset, their pain and challenges, their hopes and desires. Break it down into steps and set all the constraints up front. [See also: Chapter 3.5: Heartbeats and Handcuffs.] Understand and tell the story of the product. [See also: Chapter 3.2: Why Storytelling.] Create prototypes all along the way. [See also: Chapter 3.1: Make the Intangible Tangible

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

The people who notice the problems around them—and then dream up solutions—are mostly inventors, startup founders, and kids. Young people look at the world and question it. They’re not worn down by doing the same stupid thing a thousand times—they don’t assume everything has to be the way it is. They ask “why?” Keeping your brain young is key. Seeing problems that are glossed over by others is useful. Coming up with solutions to those problems, using the vocabulary and thought process of a designer, is invaluable.

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

A Method to the Marketing Marketing does not have to be soft and hand-wavy. While good marketing is anchored in human connection and empathy, creating and implementing your marketing programs can and should be a rigorous and analytical process. 1. Marketing cannot just be figured out at the very end. 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. 2. Use marketing to prototype your product narrative. The creative team can help you make the product narrative tangible. This should happen in parallel with product development—one should feed the other. 3. The product is the brand. The actual experience a customer has with your product will do far more to cement your brand in their heads than any advertising you can show them. Marketing is part of every customer touchpoint whether you realize it or not. 4. Nothing exists in a vacuum. You can’t just make an ad and think you’re done. The ad leads to a website that sends you to a store where you purchase a box that contains a guide that helps you with installation, after which you’re greeted by a welcome email. The entire experience has to be designed together, with different touchpoints explaining different parts of your messaging to create a consistent, cohesive experience. 5. The best marketing is just telling the truth. The ultimate job of marketing is to find the very best way to tell the true story of your product.

These are the same people who dismiss marketing as unnecessary fluff or a necessary evil. They think it’s about bullshitting people, stopping at nothing to take their money. Building the product is good and clean, but then to sell it you have to get a little dirty. But good marketing isn’t bullshitting. It’s not about making something up, crafting a fiction, exaggerating your product’s benefits, and burying its faults. Steve Jobs often said, “The best marketing is just telling the truth.” If the messaging rings true, then the marketing is better. You don’t have to rely on bells and whistles, stunts, and dancing polar bears—you simply explain in the best way possible what you’re making and why you’re making it.

First you break down the pain points that your customer is feeling or has habituated away. Each pain is a “why”—it gives your product a reason to exist. The painkiller is the “how”—these are the features that will solve the customer’s problem. The “I want it” column explains the emotions that your customers are feeling. The “I need it” column covers the rational reasons to buy this product. The whole product narrative should be in there—every pain, every painkiller, every rational and emotional impulse, every insight about your customer. It needs to encompass everything because:

So when we were thinking about how the thermostat would reach customers, we laid out all the different ways people could discover our brand: advertising, word of mouth, social media, reviews, interviews, in-store displays, launch events. Then we laid out the next step in the process—how they’d learn about our product. Brochures, our website, packaging, etc. And then we created a messaging activation matrix. When we were deciding what went where, it was crucial to know which parts of the story customers would be exposed to at various points of the journey. Top-line billboards would just introduce the idea of a new kind of thermostat. The packaging would highlight the top six features and how the product connects to your phone. The website would emphasize energy savings and showcase how Nest fits into your daily life. The usage guide inside the packaging would provide more detail about how to train the learning algorithm and tips for saving energy. The support site would go deeper with exact instructions and thorough explanations of all the features.

The whole point of the creative team is to be creative, to come up with the most elegant and compelling version of the truth, to tell your story beautifully. But unchecked creativity can get you sued. You do not want to do it without a lawyer present.

So nothing was ever presented to me without context—I would always expect to see what came before, what came after. I’d need to know the story we were telling and to whom we were telling it and at what point of the journey they were. An ad can’t be understood without knowing where it will appear and where it will lead to. A webpage can’t be approved until you know who will be routed to that page and what they’ll need to know and where the call to action will take them. Everything is connected to everything, so everything must be understood together.

I wanted the words and images that we used to describe our products to be as great as the products themselves. I wanted the entire experience to shine. I wanted the marketing team to be as exacting as the engineering and manufacturing teams—to learn from this rigor so they would begin to push themselves just as hard, or harder, than I pushed them. I knew marketing was going to have to be one of our differentiators—something that lifted us beyond anything any other thermostat maker could dream of—so it was important to give it time and attention. And money.

The reason is that marketing was part of the process from day one. Nobody was ignoring it, nobody was forgetting about it. We knew it was useful, so we used it.

marketing prototyped the product narrative in parallel with product development.

Each part of the website highlighted a different part of the product story. That forced us to know the story in our bones, to live and breathe it so we could pass it to others in the clearest, most honest way possible.

Finding the best, most honest expression of a product or feature is not easy. That’s why there’s an entire team devoted to it. Product management can create the messaging—the top features, the problem statement—but finding the best way to tell that story to customers is an art. It’s a science. It’s marketing.

With every piece of marketing we made, we got better at marketing. I got better at marketing. The entire company got better at marketing. The messaging architecture and activation matrix turned a soft art into a hard science that everyone could understand. And when everyone can understand it, they can understand how important it is.

Product manager or product marketing manager—Product marketing and product management are essentially the same thing—or at least they should be. A product manager’s responsibility is to figure out what the product should do and then create the spec (the description of how it will work) as well as the messaging (the facts you want customers to understand). Then they work with almost every part of the business (engineering, design, customer support, finance, sales, marketing, etc.) to get the product spec’d, built, and brought to market. They ensure that it stays true to its original intent and doesn’t get watered down along the way. But, most importantly, product managers are the voice of the customer. They keep every team in check to make sure they don’t lose sight of the ultimate goal—happy, satisfied customers.

Project manager—Coordinates tasks, meetings, calendars, and assets to enable individual projects to get done on time. It’s important to note that project managers are more than just glorified note takers. If the product manager is the voice of the product, the project manager is the voice of the project—their job is to alert the team to potential problems that could stall or derail the project and to help find solutions.

Program manager—Supervises groups of projects and project managers, focusing on both long-term business objectives and short-term deliverables.

And the reason for it is simple: the customer needs a voice on the team. Engineers like to build products using the coolest new technology. Sales wants to build products that will make them a lot of money. But the product manager’s sole focus and responsibility is to build the right products for their customers. That’s the job.

A good product manager will do a little of everything and a great deal of all this: Spec out what the product should do and the road map for where it will go over time. Determine and maintain the messaging matrix. Work with engineering to get the product built according to spec. Work with design to make it intuitive and attractive to the target customer. Work with marketing to help them understand the technical nuances in order to develop effective creative to communicate the messaging. Present the product to management and get feedback from the execs. Work with sales and finance to make sure this product has a market and can eventually make money. Work with customer support to write necessary instructions, help manage problems, and take in customer requests and complaints. Work with PR to address public perceptions, write the mock press release, and often act as a spokesperson.

And then there’s the even less well-defined stuff. Product managers look for places where the customer is unhappy. They unravel issues as they go, discovering the root of the problem and working with the team to solve it. They do whatever is necessary to move projects forward—that could be taking notes in meetings or triaging bugs or summarizing customer feedback or organizing team docs or sitting down with designers and sketching something out or meeting with engineering and digging into the code. It’s different for every product.

But from my experience that’s a grievous mistake. Those are, and should always be, one job. There should be no separation between what the product will be and how it will be explained—the story has to be utterly cohesive from the beginning.

He doesn’t just understand the customer. He becomes the customer. He can shake off his deep, geeky knowledge of the product and use it like a beginner, like a regular person. You’d be surprised how many product managers skip that hugely necessary step—listening to their customers, gaining insights, empathizing with their needs, then actually using the product in the real world. But for Joz, it’s the only way.

So Joz and I didn’t bring Steve numbers—we brought him customers. Commuters like Sarah only use the iPod going to and from work, students like Tom use it throughout the day, but in short bursts between classes or basketball games. We created typical customer personas, then walked through the moments in their life when they used their iPods—while jogging, at parties, in the car. And we showed Steve that even if the number engineering gave us was twelve hours, those twelve hours actually lasted most people all week long. The numbers were empty without customers, the facts meaningless without context. Joz always, always understood the context and was able to turn it into an effective narrative. It’s how we were able to convince Steve. And reporters. And customers. It’s how we could sell iPods.

Figuring out what should be built and why is the hardest part of building. And it’s impossible to do it alone. Product management can’t just throw a spec over the fence to the rest of the team—every part of the business should be involved. That doesn’t mean the product manager should build by consensus, but engineering, marketing, finance, sales, customer support, and legal will all have ideas and useful insights that will help shape the narrative before the product is built. And they’ll continue to improve that narrative as the product evolves.

Building a product isn’t like assembling an IKEA chair. You can’t just hand people instructions and walk away.

Building a product is like making a song. The band is composed of marketing, sales, engineering, support, manufacturing, PR, legal. And the product manager is the producer—making sure everyone knows the melody, that nobody is out of tune and everyone is doing their part. They’re the only person who can see and hear how all the pieces are coming together, so they can tell when there’s too much bassoon or when a drum solo’s going on too long, when features get out of whack or people get so caught up in their own project that they forget the big picture.

If a product manager is making all the decisions, then they are not a good product manager. It’s the contributions of everyone on the team that ultimately define the melody, that turn noise into a song.

This is why product managers are the hardest people to hire and train. It’s why the great ones are so valuable and so beloved. Because they have to understand it all, make sense of it. And they do it alone. They’re one of the most important teams at a company and one of the smallest.

Rather than focusing on rewarding salespeople immediately after a transaction, vest the commission over time so your sales team is incentivized to not only bring in new customers, but also work with existing customers to ensure they’re happy and stay happy. Build a culture based on relationships rather than transactions.

  1. If you’re starting a new sales organization, do not offer traditional monthly cash commissions. It’s best to have everyone in your company compensated in the same way—so offer salespeople a competitive salary and sales performance bonuses of additional stock options that vest over time. Stock provides a built-in incentive to stick around and invest in long-term customers who are good for the business. 2. If you’re trying to transition to a relationship-driven culture, you may not be able to kill traditional commissions right away. In that case, any stock or cash (stock is still preferable) that you give as a commission should vest over time. Pay 10–15 percent of the commission at first, then another tranche in a few months, then another a few months after that, etc. If the customer leaves, the salesperson loses the remainder of their commission. 3. Every sale should be a team sale. So if you have a customer success team (the team that actually delivers, sets up, and maintains whatever is sold to the customer), then it should sign off on every deal. Sales and customer success should be under one leader, in the same silo, being compensated in the same way. In this setup, sales can’t just throw a customer over the fence and never think about them again. If there’s no customer success team, then sales should work very closely with customer support, operations, or manufacturing—create a board of people to approve each commitment.

The bigger your company, the further these two cultures will drift apart. Huge commissions, sales awards, and sales conferences where everyone high-tails it to an island, ready for a weekend of drinking, may feel great for your sales team in the moment. But they can drag morale down for the rest of the company. Why are we here working, building this thing, while they’re getting wasted in Hawaii, doing shots out of their Best Salesperson of the Year trophy? And this isn’t to say sales is not important. It’s vital. It brings in customers and cash that are absolutely necessary to keep a company alive. But it’s not more important than engineering or marketing or ops or legal or any other part of your business. It’s just one of many critical teams, all working together to make something great.

The problem is that one day something will go wrong. Maybe it’ll be with the product—you’ll have an issue and business will slow down. In that moment, the time when you need them most, your sales team will abandon you. They’ll go wherever the sales are hot. Why should they stick with you if they can’t make money right now? Or you might find out that those great numbers they’ve been putting up aren’t so great after all. Maybe they’ve been telling little white lies about your team’s capacity or your product’s ability to meet customers’ needs. Maybe all those customers flowing into your business have been sold something you can’t actually give them. And now they’re pissed.

Ideally you set up your business this way from the start. Everyone gets paid in salary, stock, and performance bonuses—sales, customer success, support, marketing, engineering, everyone. That’s not to say they get paid the same amount, but the compensation model is the same—everyone is aligned.

First set up a mini–internal board populated by those other teams—customer support, customer success, operations—to approve each sales deal. That will start shifting the mindset from lone-wolf salesperson to being part of a team. Then start talking about the change to commissions. Don’t say you’re getting rid of them—that messes with people’s heads—just say that you’re doing them differently. Boost the size of the commission but start vesting it over time. And tell the sales team they’ll lose the remainder of the commission if the customer leaves. You can also offer an even larger commission if they’ll take stock over cash. Once commissions are vested on a schedule that prioritizes customer relationships, a lot of the ugliness that usually defines sales cultures disappears. Salespeople do a better job qualifying customers, the hypercompetition eases up, the backslapping fades, the teams align their expectations and their goals. It just works better. For everyone.

Find people who are intrigued by the idea of vested commissions. Find people who realize they can actually make more money this way. Find people who are good human beings in addition to being good at sales. Find people who will care about your mission and be thrilled with the vital role they’ll play in making it a reality.

But remember that if you’re running a business, every decision involving legal matters is a business-driven decision. Purely legal-driven decisions only happen in court. Your legal team is there to inform your choices, not make them for you. So a “no” from legal isn’t the end of the conversation—it’s the beginning. A great lawyer will help you identify roadblocks, then move around them and find solutions.

If you’re moderately successful at something disruptive, you’ll probably be a target. If you’re really successful, you definitely will be.

Their job is to tell you the law and explain the risks. Your job is to make the decision.

It was an interesting lesson in what winning meant. It wasn’t a proper legal victory—we never defended ourselves, never went to court—but it was a win for Steve. It was more important for him to never spend another second of his life worrying about this lawsuit than to save money or face.

When you’re in any kind of negotiation that includes legal, you always need to work out the fundamental deal points first, before the lawyers get called in—how much you’re paying for something, how much you’re willing to spend, how long a contract should last for, exclusivity, etc. Get the term sheet roughly approved, then let the lawyers argue the legalese. Otherwise negotiations can drag on forever, with you footing the bill as your lawyers fight with their lawyers. Nobody wants to deal with that.

The best lawyers understand that. They don’t only think like a lawyer. They take into account all their training and knowledge, but also weigh business objectives. They can help you understand the risks while also being very aware of the benefits.

That’s what you’re ultimately looking for. You don’t want a lawyer who thinks their only job is to point out the sinkhole you could fall into, to block your way. Hire someone who will help you find a new path. Hire someone who will build a bridge. Hire a lawyer who doesn’t just think like a lawyer.

People have this vision of what it’s like to be an executive or CEO or leader of a huge business unit. They assume everyone at that level has enough experience and savvy to at least appear to know what they’re doing. They assume there’s thoughtfulness and strategy and long-term thinking and reasonable deals sealed with firm handshakes. But some days, it’s high school. Some days, it’s kindergarten.

There’s nothing exactly like being a CEO, and nothing to prepare you for it—not even being the head of a huge team or division of a company, firmly in the C-suite. In those positions, there’s always someone above you—but the buck truly stops with the CEO. And as CEO, you set the tone for the company. Even if there’s a board, partners, investors, employees—ultimately everyone looks to you. The things you pay attention to and care about become the priorities for the company. The best CEOs push the team to strive for greatness, then take care of them to make sure they can achieve it. The worst CEOs care only about maintaining the status quo. There are generally three kinds of CEOs: 1. Babysitter CEOs are stewards of the company and are focused on keeping it safe and predictable. They generally oversee the growth of existing products that they inherited and don’t take risks that might scare executives or shareholders. This invariably leads to the stagnation and deterioration of companies. Most public company CEOs are babysitters. 2. Parent CEOs push the company to grow and evolve. They take big risks for larger rewards. Innovative founders—like Elon Musk and Jeff Bezos—are always parent CEOs. But it’s also possible to be a parent CEO even if you didn’t start the business yourself—like Jamie Dimon at JPMorgan Chase or Satya Nadella at Microsoft. Pat Gelsinger, who recently took over the Intel CEO position, seems to be Intel’s first parent CEO since Andy Grove. 3. Incompetent CEOs are usually either simply inexperienced or founders who are ill-suited to lead a company after it reaches a certain size. They are not up to the task of being either a babysitter or a parent, so the company suffers.

The job is to give a shit. To care. About everything.

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.

If you want to build a great company, you should expect excellence from every part of it. The output of every team can make or break the customer experience, so they should all be a priority.

When you truly give a shit, you care, you don’t let up until you’re satisfied, you pick things apart until they’re great. People will hand you something that they worked on tirelessly for weeks, that they’ve thought through and are proud of, that’s 90 percent amazing. And you will tell them to go back and make it better. Your team will be shocked, stunned, possibly even dejected. They’ll say it’s already so good, we’ve worked so hard. You’ll say good enough is not good enough. So they’ll march out the door and do it again. And, if necessary, again. They might get so tangled up that it’ll be simpler to just start from scratch. But with each iteration, each new version, each regroup and reimagining, they’ll discover something new. Something great. Something better. Most people are happy with 90 percent good. Most leaders will take pity on their teams and just let it slide. But going from 90 to 95 percent is halfway to perfect. Getting the last part of the journey right is the only way to reach your destination. So you push. Yourself. The team. You push people to discover how great they can be. You push until they start pushing back. In these moments, always err on the side of almost-too-much. Keep pushing until you find out if what you’re asking for is actually impossible or just a whole lot of work. Get to the point of pain so you start to see when the pain is becoming real. That’s when you back down and find a new middle ground.

Because you’re it. You’re the top of the pyramid. Your focus, your passion, trickles down. If you don’t give a shit about marketing, you’ll get shitty marketing. If you don’t care about design, you’ll get designers who don’t care, either. So don’t worry about picking your battles. Don’t rack your brain trying to decide which parts of your company need your attention and which don’t. They all do. You can prioritize, but nothing ever comes off the list. Avoiding or ignoring any part of your company only comes back to haunt you sooner or later.

You don’t have to be an expert in everything. You just have to care about it. No matter your leadership style, no matter what kind of person you are—if you want to be a great leader, you have to follow that one cardinal rule. The other commonalities of successful leaders are just as straightforward: They hold people (and themselves) accountable and drive for results. They’re hands-on, but to a point. They know when to back off and delegate. They can keep an eye on the long-term vision while still being eyeball-deep in details. They’re constantly learning, always interested in new opportunities, new technologies, new trends, new people. And they do it because they’re engaged and curious, not because those things may end up making them money. If they screw up, they admit to it and own their mistakes. They’re not afraid to make hard decisions, even when they know people will be upset and angry. They (mostly) know themselves. They have a clear view of both their strengths and challenges. They can tell the difference between an opinion- and data-driven decision and act accordingly. [See also: Chapter 2.2: Data Versus Opinion.] They realize that nothing should be theirs, even if the genesis was with them. It all has to be the team’s. The company’s. They know their job is to jubilantly celebrate everyone else’s successes, to make sure they get credit for them, and hold little for themselves. They listen. To their team, to their customers, to their board, to their mentors. They pay attention to the opinions and thoughts of the people around them and adjust their views when they get new information from sources they trust.

In this job, respect is always more important than being liked. You can’t please everyone. Trying can be ruinous. 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. Delaying hard decisions, hoping problems will resolve themselves, or keeping pleasant but incompetent people on the team might make you feel better. It may give you the illusion of niceness. But it chips away at the company, bit by bit, and erodes the team’s respect for you.

So it’s wise to stand alone—not to let anyone at work get too close. Even if you wish you could just grab a drink with your team like you used to. It’s a cliché to say “It’s lonely at the top.” But it’s also true. Most people assume being CEO is a hard job—stressful, busy, high-pressure. But the stress is one thing; the isolation is another. You might have a cofounder, but you shouldn’t have a co-CEO. It’s a one-person job and you’re all alone up there.

That freedom is thrilling and empowering and utterly terrifying. There is nothing scarier than finally getting what you want and having to take responsibility for it, good or bad. And the tables begin to turn—as CEO you can’t say “yes” to everything. You have to become the one who says “no.” Freedom is a double-edged sword. But it’s still a sword. You can use it to cut through the bullshit, the hesitation, the red tape, the habituation. You can use it to create whatever you want. The right way. Your way. You can change things. That’s why you start a company. That’s why you become CEO.

Everyone needs a boss to be accountable to and coaches who can help them through difficult times—even a CEO. Especially a CEO. That’s why businesses have a board of directors—typically just called “the board”—where members are directors of the company. A board’s primary responsibility is to hire and fire the CEO. That is the main way they can protect the company and the one and only job they have that really counts. Everything else comes down to giving good advice and respectful, no-bullshit feedback that hopefully steers the CEO in the right direction. Ultimately it’s the CEO who’s responsible for running a company. But CEOs need to prove to the board that they’re doing a good job, or risk being fired. That’s why board meetings are so important, and why truly understanding your subject matter and doing a great deal of prep work beforehand is vital. The best CEOs always know the outcome of a board meeting before they walk through the door.

Bad CEOs come to board meetings and expect the board to help them make decisions. Good CEOs walk in with a presentation of where the company was, where it is now, and where it’s headed this quarter and in the years to come. They tell the board what’s working but they’re also transparent about what isn’t and how they’re addressing it. They present a fully formed plan that the board can question, object to, or try to modify. Things might get a little heated, a little bumpy, but in the end everyone walks out of the meeting understanding and accepting the CEO’s vision and the company’s path forward. Then there are the great CEOs. With great CEOs the meeting is smooth as butter.

Bill Campbell helped me understand how he did it. Bill would always say that if there was any potentially surprising or controversial topic, the CEO should go to every board member, one-on-one, to walk them through it before the meeting. That allowed them to ask questions, offer different perspectives, and then the CEO had time to take those thoughts back to the team and revise their thinking, presentation, and plan. There should only be good surprises in a board meeting—We’ve exceeded our numbers! We’re ahead of schedule! Check out this cool demo! Everything else should be a known quantity. It’s best not to debate new discussion items in the boardroom—there’s just never enough time to cover them in detail and get to a resolution. It always goes nowhere.

Being able to help the board grasp exactly what’s going on is good for the CEO, too. The better you can explain something, the more you understand it. Teaching is the best test of your own knowledge. If you’re struggling to explain what you’re building and why, if you’re presenting a report without really understanding it, if the board is asking you questions that you can’t answer—then you have not internalized what’s actually going on at your company. That’s when you might have a real problem. It doesn’t happen all that often, but sometimes a board does its most important and least pleasant job: they remove the CEO. Usually it’s because the CEO is in the wrong—they’re incapable or incompetent or pushing an agenda that will lead to ruin. Or sometimes a first-time founder has done a great job up until now but the company needs someone with different expertise and skills to take it to the next level. But sometimes the problem isn’t the CEO. It’s the board.

Even the best CEO cannot stand alone, untouchable, unchallengeable, accountable to no one. Everyone needs to report to someone, even if it’s a two-person board that you meet with for an hour every few months. There always needs to be some kind of pressure-release valve. There always needs to be someone who can shake their head and give it to you straight. And if you do it right, you should never be a victim of your board. As CEO, you help to shape it. Boards always change based on the CEO—the board under Steve Jobs was different from the board under Tim Cook. Boards complement a CEO’s strengths and no two CEOs are alike.

The best board members are mentors first. They’re able to offer sound, helpful advice at critical moments in your product’s life or in yours. And they give as well as take—they enjoy the process of being on your board because they’re learning something, too. You just have to make sure they don’t use those learnings against you.

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. If a large company is acquiring a tiny team—a dozen people or fewer—cultural mismatch is much less of an issue. But even then, that tiny team should carefully assess how they’ll be digested by the larger org and really take their time to understand the culture of the company they’re about to join.

Bill Campbell liked to say, “Great companies are bought, not sold.” If you’re being acquired, you want the buyer to be desperate to buy rather than you being a seller desperate to sell. If you’re considering an acquisition, you want to be wary of anyone throwing themselves at you, pitching you too hard.

My advice is to always be cautiously optimistic. Trust, but verify. Assume people have the best intentions, then make sure they’re following through on them. And take the risk. Leap. Buy the company. Sell the company. Or do neither. Just follow your gut and don’t be scared (or, rather, be scared but make the decision anyway).

Beware of too many perks. Taking care of employees is 100 percent your responsibility. Distracting and coddling them is not. The cold war of ever-escalating perks between startups and modern big tech has convinced many companies that they need to serve three gourmet meals a day and offer free haircuts to attract employees. They do not. And they should not. Keep in mind there’s a difference between benefits and perks: Benefit: Things like a 401(k), health insurance, dental insurance, employee savings plans, maternity and paternity leave—the things that really matter and can make a substantive impact on your employees’ lives. Perk: An occasional pleasant surprise that feels special, novel, and exciting. Free clothes, free food, parties, gifts. Perks can be completely free or subsidized by the company. Getting benefits right is crucially important for your team and their families. You want to support the people you work with and make their lives better. Benefits allow your team and their families to stay healthy and happy and achieve their financial goals. This is where you should be spending your money. Perks are a very different matter. In and of themselves, perks are not a bad thing. Surprising and delighting your team is wonderful and often necessary. But when perks are always free, appear constantly, and are treated like benefits, your business will suffer. An oversupply of perks hurts a company’s bottom line and, contrary to popular belief, employee morale. Some people can become obsessed with what they can get rather than what they can do—believing perks to be a right, not a privilege. Then when times get tough or when the perks don’t scale, they become outraged that their “rights” are being taken away. And if the primary way you’re attracting talent is through perks, then times will absolutely get tough.

If you want to give employees a perk, keep in mind two things: When people pay for something, they value it. If something is free, it is literally worthless. So if employees get a perk all the time, then it should be subsidized, not free. If something happens only rarely, it’s special. If it happens all the time, the specialness evaporates. So if a perk is only received occasionally, it can be free. But you should make it very clear that this is not going to be a regular occurrence and change up the perk so it’s always a surprise.

Just as any good and giving person can get taken advantage of, can be abused, so too can the good intentions of a company. Some people just take and take and take and believe it to be their right. And after a while the culture of the company evolves to accept that and even encourage it. That’s why I said, “Fuck massages.”

Unbecoming CEO A CEO is not a king or queen. It’s not a lifetime appointment. At some point, you have to step down. Here’s how you’ll know it’s time: 1. The company or market has changed too much: Some startup founders are not meant to be CEOs of larger companies. Some CEOs have the skills to manage one set of challenges and not another. If everything has changed so much that you have no idea how to manage it and the solutions you need to implement are completely out of your wheelhouse, it’s probably time to go. 2. You’ve turned into a babysitter CEO: You’ve settled into maintenance mode rather than continually challenging and growing your company. 3. You’re being pushed to become a babysitter CEO: Your board is demanding you stop taking big risks and just keep the trains running. 4. You have a clear succession plan and the company’s on an upswing: If things are going great and you think one or two execs on the team are ready to move up, then it may be time to make some room for them. Always try to leave on a positive note and leave the company in good hands. 5. You hate it: This job is not for everyone. If you can’t stand it, that doesn’t mean you’ve failed. It just means you’ve discovered something useful about yourself and can now use that discovery to find a job you love.

Sometimes they don’t know how a medium-sized company works, let alone a big one. They might not have the right mentors around them, might not know how to build a team or attract customers. And when all that falls on their heads, they typically revert to what they were good at when they were an individual contributor and abandon the real responsibilities of CEO, ignore the board’s warnings, flounder, and implode. It’s a hard but valuable lesson and many entrepreneurs learn from it and try again, usually with more success. I was one of them.

But that kind of experience is avoidable. You can notice when you’re in a nosedive, you can look around, feel the wind in your hair. And you can do something about it—admit what’s happening and step down. But most CEOs who are on the brink of failure just shut their eyes and wait for the crash. There’s often so much of their ego wrapped up in being a CEO, so much time and work. People spend their entire lives striving to lead a company. They make it the center of their self-worth and their identity. The prospect of letting go of that—just walking away—can be terrifying.

It’s your job as a CEO to constantly push your company forward—to come up with new ideas and projects to keep it fresh and alive. Then it’s your job to work hard on those new projects, to be as passionate about them as you were about the original problem you came there to solve. In the meantime, other people on your team focus on your core business, optimizing the pieces that are already set up.

Founders need to be aware that they can easily undermine the work of the CEO and core team. Even if a founder chooses to only be a member of the board, they still have to be careful—they’re not leading the team anymore. They become a coach, a mentor, an advisor. Just one voice out of many.

Then for the next six months you can begin to look at your life with fresh eyes. Get distracted. Get excited. Start thinking about what’s next. And you don’t have to get right back on the same racetrack that you jumped off the year before. Just because you were CEO once doesn’t mean you need to be CEO again. You can always find or create new opportunities for yourself. You can always learn and grow and change. Take the time you need to become the person you want to be. Just like you did at the start of your career and at every fork in the road along the way.

In the end, there are two things that matter: products and people. What you build and who you build it with. The things you make—the ideas you chase and the ideas that chase you—will ultimately define your career. And the people you chase them with may define your life. It’s incredibly special to create something together with a team. From nothing, from chaos, from a spark in someone’s head, to a product, a business, a culture.

So you push. As a leader, a CEO, a mentor—you push even when people resent you for it. Even when you worry that maybe you’ve pushed too far … But there’s always a reward on the other side. It’s worth it to do things well. It’s worth it to try for greatness. It’s worth it to help your team, to help people. And one day you’ll get an email from someone you worked with—two, three, maybe ten years ago. And they’ll thank you. Thank you for pushing them. For helping them realize what they were capable of. They’ll say they hated you for it then, resented every minute, couldn’t believe how hard they had to work, how you made them start from scratch, how you wouldn’t let up. But eventually they realized that moment had been a turning point, a jumping-off point. It changed the trajectory of their entire career. The things you built together changed their life. And that’s how you’ll know you’ve done something meaningful. You’ve made something worth making.

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