I really adore this book. It’s now in my top 3 favorite business books. I figured I’d share the bits that stood out to me while reading this book below:

Learning

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

Work

• You should never kill yourself for your job, and no job should ever expect that of you.
• Too many people throw themselves blindly at hot trends, anticipating a gold rush, and end up falling off a cliff.
• 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.
• The only thing that can make a job truly amazing or a complete waste of time is the people.

Startups

• General Magic was making incredible technology but wasn’t making a product that would solve real peoples problems. We started from the technology—focusing on what we could create, what would impress the geniuses at our company—not the reason why real, non-technical people would need it.
• If you’re not solving a real problem, you can’t start a revolution.
• Take Uber. The founders started with a customer problem—a problem they experienced in their daily lives—then applied technology.

Entrepreneurship

• The choice to stay or go, to collect a paycheck or save your sanity, to stick with the big company or jump ship to your own venture—it’s difficult for everyone.

Management

• A great deal of management comes down to how you manage your own fears and anxieties.
• A lot of people shouldn’t be forced into management—if you’re not really a people person, or you only want to focus on the work, or you thrive on having regular day-to-day successes and accomplishments and the murky maybe-your-team-will-succeed-one-day style of management is less motivating to you.
• I wanted to understand the squishy stuff and the geeky stuff. And I liked all of it. I could also translate back-and-forth—explain the squish to engineers, translate the ones and zeros to the creatives. I could synthesize all the pieces and keep the whole company in my head. For me, that was thrilling, exciting, inspiring.
• As a manager, you should be focused on making sure the team is producing the best possible product.
• 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 create so much space that you lose track of what’s going on or are surprised by what the product becomes.
• Examining the product in great detail and caring deeply about the quality of what your team is producing is not micromanagement. That is exactly what you should be doing.
• Just be honest with your team. Even if things aren’t going well, don’t avoid telling them the hard truth. Tear off the Band-Aid.

Process

• 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 make sure everything is headed 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 notes document that helps you keep your priorities and the questions you need to ask top of mind. 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.
• Give formal written performance reviews every six months. But those formal reviews should simply be an exercise in writing down the things you’re already 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.

Decisions

• You can’t wait for perfect data. It doesn’t exist.
• most decisions we make are data-informed, but not data-made.
• 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 decisions are where you can acquire, study, and debate facts and numbers that will allow you to be fairly confident in your choice.
• Opinion driven decisions are those in which 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.
• Most people don’t even want to acknowledge that there are opinion-driven decisions or that they have to make them. Because if you follow your gut and your gut is wrong, then there’s nowhere else to cast blame.
• Trusting your gut is incredibly scary. Many people don’t have either a good gut instinct to follow or the faith in themselves to follow it.
• It’s your responsibility as a manager or leader to explain that this isn’t a democracy, but 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.
• Tell the team your thought process. Walked through all the data you looked at, all the insights you gathered, and why you ultimately made the choice. Take peoples input. Listen, don’t react.

Design

• Customer panels can’t design for crap. People just can’t articulate what they want clearly enough to definitely point in one direction or another. Customers will always be more comfortable with what exists already, even if it’s terrible.
• A/B and user testing is not product design. It’s a tool. A test. At best, a diagnosis. It can tell you somethings not working, but it won’t tell you how to fix it.
• Speaking about designing nest: every minute, from opening the box to reading the instructions to getting it on their wall to turning on the heat for the first time, had to be incredibly smooth. A buttery, warm, joyful experience.

Storytelling

• Storytelling is how you get people to take a leap of faith to do something new.
• Creating a believable narrative that everyone can latch onto is critical to moving forward and making hard choices.
• The story of your products, your company, and your vision should drive everything you do.
• The story doesn’t just exist to sell your product. It’s there to help you define it, understand it, and understand your customers.
• It all starts with Why. Why does this thing need to exist? Why does it matter? Why will people need it? Why would they love it?
• You have to find an opportunity to craft stories that stick with customers and keep them talking about you.
• Tell stories people can connect with. A good story is an act of empathy. It blends facts and feelings.
• There’s an art to telling a compelling story. But there’s also a science.
• Great analogies allow customers to instantly grasp a difficult feature and then describe that feature to others. That’s why “1000 songs in your pocket” was so powerful. We cheated. We didn’t try to explain everything. We just used an analogy.
• You should always be striving to tell a story so good then it stops being yours—so your customer learns it, loves it, internalizes it, owns it. And tells it to everyone they know.

A-holes

• A-holes come in different flavors of selfish or deceitful or cruel, but have one unifying characteristic: you cannot trust them.
• They can and will screw you and your team over, either to get something for themselves or just to push you down and make themselves look like the hero.
• Political a-holes master the art of corporate politics, but then do nothing but take credit for everyone else’s work.
• Controlling a-holes are micromanagers who systematically strangled the creativity and joy out of their team.
• Natural a-holes suck at work and everything else. They’re mean, jealous, insecure jerks.
• Mission driven a-holes are crazy passionate and a little crazy. They speak most frankly, trampling the politics of the modern office, and steam roll right over the delicate social order of “how things are done around here”. A mission driven a-hole might tear apart your work, but they won’t attack you personally. They won’t call you names or fire you for disagreeing with them.
• There’s a world a difference between being emphatic and passionate to benefit the customer versus bullying someone to appease your own ego.
• Real a-holes always make it personal. Their motivation is their ego, not the work.
• When an alliance of a holes start spreading lies, or stealing ideas, or taking over projects they have no business touching, they will pair each other’s words to leader ship. They will make sure they all have the same narrative.
• Most people aren’t a-holes. 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.

Quitting

• Sometimes it’s just time to go. And when that moment comes, you’ll probably know. Quit and go do something you’ll love.

Customer Experience

• Your product isn’t only your product. It’s the whole user experience.
• The actual thing your building is only one tiny part of a vast, intangible, overlooked user journey that starts long before a customer ever gets their hands on your product and ends long after.
• 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.
• Map out and visualize exactly how a customer discovers, considers, installs, uses, fixes, and even returns your product. It all matters.
• 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.
• You have to prototype the whole experience—give every part the weight and reality of a physical object. Draw pictures. Make models. Pin mood boards. Sketch out the bones of the process in rough wire frames. Write imaginary press releases. Create detailed mock ups.
• 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.
• 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, and selling and selling until they’re sick of you?

Disruption

• Your V1 product should be disruptive, not revolutionary.
• Refine what you made in the V1 using data and insights from actual customers and double down on your original disruption.
• Always seek out new ways to disrupt yourself.
• If you’ve truly made something disruptive, you’re competition probably won’t be able to replicate it quickly.
• If you under shoot, there’ll be an almost audible fizz.
• You need some thing that will make people stop in their tracks and say, “Wow. Tell me more.”
• If you’re disrupting big, entrenched industries, your competition will almost certainly dismiss you in the beginning. They’ll flat out laugh in your face.
• Soon as your disruptive product, process, or business model begins to gain steam with customers, your competitors will start to get worried.
• When they realize you might steal their market share, they’ll get pissed. Really pissed. When people hit the anger stage of grief, they lash out, punching something.
• And they might sue you. If they can’t innovate, they’ll litigate. The good news is that a lawsuit means you have officially arrived.
• 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.
• Disruption makes enemies.
• Even starting something new in a big company won’t protect you. You’ll have to deal with politics, jealousy, and fear. You’re trying to change things, and change is scary, especially the people who think they’ve mastered their domain and who are completely unprepared for the ground to shift under their feet.
• Just don’t overshoot. Don’t try and disrupt everything at once.
• When you can see the competition nipping at your heels, you have to do something new. You have to fundamentally change who you are as a business.
• Companies that become too big, too comfortable, too obsessed with preserving and protecting what first big innovation they put them on the map—they topple. They unravel. They die.

Time

• You need constraints to make good decisions in 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 some thing that will never be finished.
• The joke is that it takes 20 years to make an overnight success. In business, it’s more like 6 to 10. 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.
• Customers need time to fill you out. The vast majority of people aren’t early adopters—they won’t try new things right away. They need time to get used to the idea, time to read some reviews, time to ask their friends, and then time to wait until the next version comes out because that’ll probably be even cooler.
• No matter what your building, reaching profitability will take longer than you think. The iPod took three generations—and three years—before it reached profitable unit economics.
• Google wasn’t remotely profitable for a long time. They only started making real money when they figured out AdWords. Facebook decided to capture eyeballs, then figure out the business model later. So did Pinterest and Twitter. They created a V1 product, scaled it for V2, then optimized the business in V3.

Managing Complexity

• I needed to calm down. I needed to find space. I needed to prioritize.
• 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.
• 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 persons team? What are the next major milestones? What date commitments did our teams make?
• Whenever someone had a great idea, and write it down on this paper.
• The only way for me to capture all of it—good ideas, priorities, roadblocks, the dates that people promise to deliver, and the major internal and external heartbeats ahead—was to take notes in every meeting. Long hand. Not on a computer.
• The act of using a pen, then re-typing and editing later, forced me to process information differently.
• Every Sunday evening, I would go through my notes, reassess and re-prioritize all my tasks, rifle through the good ideas, then update those papers on a computer and print out a new version for the week.
• 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 have a meeting about it. Everyone hated it. It wasn’t micromanagement. It was holding people accountable. It was labor-intensive. Arcane. Never-ending. But it worked.
• It kept me relatively calm. It helped me focus. And nobody ever had to wonder where my head was at. Everyone always knew what mattered to me—they had my priorities in writing, updated, every week.
• Sometimes the pressure and the stress and never-ending list and never-ending meetings will become too much. In those moments get the hell out. Take a walk.
• Don’t make a bad decision because you’re frustrated and overworked—get your head on straight and come in fresh the next day.

Healthy Practices

• Once you have a way to prioritize your tasks, you need to prioritize your physical and mental well-being.
• For the love of all that’s holy, keep your phone away from your bed. You’re an addict. We all are.
• Look at your calendar. Engineer it. Design it.
• Re-engineer your day, your week, and your monthly schedule with time dedicated to feeling human.
• 2 to 3 times a week block out parts of your schedule during your workday so you have time to think and reflect. Give your brain a second to catch up.
• 4 to 6 times a week—exercise. Get up. Go biking or running or weightlifting or cross-training or just take a walk.
• Eat well—you are an extreme athlete, but your sport is work. Don’t eat too much, don’t eat too late, cut down on refined sugars, smoking, alcohol. Just try to keep yourself from physically feeling like garbage.

Crisis

• Keep your focus on how to fix the problem, not who to blame.
• As a leader, you’ll have to get into the weeds. As the crisis unfolds your job is to tell people what to do and how to do it.
• Get advice. From mentors, investors, your board, or anyone else you know who’s gone through something similar.
• Your job once people get over the initial shock will be constant communication.
• Accept responsibility for how it has affected customers and apologize.
• Schedule check-ins in the morning and at the end of the day.
• Start going to their daily meetings. You have to be there, listening, asking questions, and getting necessary information in real time.
• Clear your calendar of nonessential meetings. Focus entirely on fixing the problem.
• Reiterate that we’ll get through this. We’ve done it before. Here’s the plan.
• Tell customers exactly what happened. No cover-up. Mea culpa and here’s a refund if you want one.
• 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.
• Get advice. Take deep breaths. Make a plan.
• But after it’s all over you should celebrate. You should have a party. And you should tell the story. The most valuable thing you’ll take out of any crisis is the tale of how you were almost swept away, but the team pulled together and saved the day. That story needs to enter into the DNA of your company.

Team

• The key to our success—was the human beings we hired, the culture they created, the way they thought and organized and work together. The team was everything.
• Forming that team and shepherding it through its many transitions is always the hardest and most rewarding part of building anything.
• A near-perfect team is made up of smart, passionate, imperfect people who complement one another.
• 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.
• We expected candidates to be mission driven and good on their feet, the right fit for the culture, and passionate about the customer. We also had a “no a-holes” policy.
• People first. Always.

PMs

• 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 managers sole focus and responsibility is to build the right products for their customers. That’s the job.
• Look for places where the customer is unhappy.
• Do whatever is necessary to move the project forward.
• The superpower of every truly great product manager is empathy.
• Product management has to own the messaging. The messaging predicts peoples concerns and finds ways to mitigate them.
• A spec and messaging aren’t instructions that are set in stone. They flex and change, shifting as new ideas are introduced.
• Building a product is like making a song. The band is composed of marketing, sales, design, engineering, support, 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.
• Sometimes they’ll have the final opinion, sometimes they’ll have to say “no”, sometimes they’ll have to direct from the front. But that should be rare. Mostly they empower the team.
• If a product manager is making all the decisions, then they are not a good product manager.
• They have to tell the story of the customer, make sure everyone feels it. And that’s how they move the needle.
• The thread that ties all these people and teams and pains and desires together is product management.

Sales

• Sales people are traditionally paid on commission. People—especially salespeople—will tell you that this is the way it’s always been done, that it’s the only way to do it and it’s the only path to hiring a decent sales team. These people are wrong.
• Rather than focusing on rewarding sales people immediately after a transaction, that’s the commission overtime 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.
• Offer sales people a competitive salary and sales performance bonuses of additional stock options that vest over time.
• If the customer leaves, the sales person loses the remainder of their commission.
• Sales and customer success should be under 1 L, in the same silo, being compensated in the same way.
• The best salespeople are the ones who maintain relationships even if it means not making money that day.
• The danger with traditional commission based sales models is that they create two different cultures: a company culture and a sales culture. The bigger your company, the further these two cultures will drift apart.
• Nobody ever works a sale alone. During the sales process the sales person has back up from support or whoever will be working closely with the customer post-sale. And then those teams sign off on the deal. There are never any surprises.
• Once the deal is closed, the sales person doesn’t disappear. They stay on as a point of contact for the customer, and if there’s any kind of issue, they step in to resell them.
• Once commissions are vested on a schedule that prioritizes customer relationships, a lot of the ugliness that usually defined sales cultures disappears.

CEO

• There’s nothing exactly like being a CEO, and nothing to prepare you for it.
• This job will suck you dry if you let it.
• The best CEOs push the team to strive for greatness, then take care of them to make sure they can achieve it.
• If a leader gets distracted from the customer 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.
• There can’t be any functions that you dismiss a secondary—where you casually accept mediocrity because it doesn’t really matter. Everything matters.
• Most people are happy with 90% good. Most leaders will take pity on their teams and just let it slide.
• After a while, they’ll work incredibly hard not just to make you happy, but because they know how much pride they feel when they do world-class work.
• If you don’t give a crap about marketing, you’ll get crappy marketing. Same for any other function in your company.
• 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.
• In this job, respect is always more important than being liked. You can’t please everyone.
• There’s always some new crisis, some new people problem, someone quitting, someone complaining, someone falling apart.
• 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.
• When you’re a CEO, you dream that maybe, 10 years down the road, some people will think you did a good job. But you can never tell how you’re doing in the moment. You can never sit back and look at a job well done.

Boards

• Good CEOs walk in with a presentation of where the company was, where 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 the board can question, object to, or try to modify.
• Watching Steve Jobs in an apple board meeting was like watching a master conductor direct in orchestra. There was no confusion, no conflict.
• Bill Campbell would always say that if there was any potential 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.
• It’s best not to debate new discussion items in the board room—there’s just never enough time to cover them in detail and get to a resolution. It always goes nowhere.
• The best thing about private boards is that you can keep them small—3 to 5 board members is best.
• When you were presenting numbers, it becomes more important to craft an arrogant. You have to tell a story.
• Even the most incredible CEOs in the world still need a board.
• Even the best CEO cannot stand alone, untouchable, unchallengeable, accountable to no one. Everyone needs to report to someone.
• Show a redacted version of the board presentation to the whole company as soon as possible after the meeting. Here’s what we talked about, here’s what I’m concerned about, here’s what the board had questions about, here are actions will take.