• You don't want to be the best at what you do, you want to be the only one who does what you do.
  • I read this book when I was growing up. Pat Riley was invited to coach several basketball teams successfully and then became the general manager of the Miami Heat. He wrote a book in the 1990s called "The Winner Within," which is kind of cheesy, but there are a couple of lessons in there. One of them was a quote from Jerry Garcia, of all things, where he said, 'You don't want to be the best at what you do, you want to be the only one who does what you do.' That made sense to me at the time, and I basically give people advice to figure out how to be the only one who does what they do. Obviously, you have to narrow your definition of what you do to accomplish that, but it's also a little bit like the personal statement you write when you apply to elite schools. The people who get accepted are generally those who write a really good personal statement that defines them in a unique way. I think the same thing is true professionally, and it's the exercise of figuring out what that could be, what that should be for you. It often takes time, trial and error, to figure that out. It's not obvious for most people.
• Starting a company just for the sake of being a founder is not a good idea.
  • I believe that you should only start a company if you have a specific idea that you're pretty excited about. I don't believe in the 'I want to be a founder' like philosophy of life, even though some people like Rishi Garg and Boswell had an idea. Boswell definitely had an idea, while Rishi was a little bit more exploratory. He wanted to come back to what he was passionate about, which was fitness. So, I think there's a need to test your ideas. You may have an idea that you're pretty excited about, but is it really a good idea? And that's a reasonable process to go through before you recruit people to your team, before you raise capital, and before you commit X years of your life. However, I don't think it's a good idea to say 'I have no idea what I want to do with my life. I know I want to found a company because that's kind of cool or trendy. So, I'm going to explore a bunch of ideas.
• It is important to have a specific startup idea that sparks passion.
  • If someone comes to me saying, 'I want to be a founder', I would hope that they have a specific idea that they just can't stop thinking about. It doesn't have to be an original idea; it can be something they heard from someone else that sparked something within them. Then, they need to consider the barriers to success with this idea - the market, distribution, and other complexities - and figure out how to overcome them. It's perfectly fine to discover an insurmountable barrier and decide not to pursue the idea. It's usually something that you encounter, and then you realize that others have the same problem. It could be a small group of people, and you may think that the problem is important to the rest of the world and that you can fundamentally transform their lives. You may then realize that there are many people like them that you didn't know of before.
• Once you meet them in person, I think it's a lot easier once you develop a little bit of taste. Is there a spark? And what kind of spark you're looking for? For what kind of role? Like if the person wants a job as you know, a job within a company, it's sort of a different spark you might be looking for.
  • My first week working for Peter at PayPal, we went for a jog around the Stanford campus. We started talking about building a company, and he gave me this lesson in November 2000. The conversation was about finding undiscovered talent, like hiring people that others may not know how to assess. By the time you're around 30 years old, with a LinkedIn profile and a resume, almost everybody evaluates you equally based on those data points. Anyone can run the same machine sort of on it and come to roughly the same output. So, if you want to find people who don't have enough data points for the recruiting machines to process, you still have to figure out a way to do this. It's like drafting athletes out of high school in baseball, basketball, or college in football, projecting them into a future professional role. Obviously, some people do it better than others in sports, and it's similar in hiring. The hardest part is actually deciding who to meet with first, because there's an infinite number of people you could potentially meet with, and there's no great political way to handle meetings. Once you commit to a meeting, there's no way around it, and meetings are expensive in terms of time. You can't literally meet with everyone. So, that's an extremely difficult task. Because if you look at the paper or the LinkedIn profile, you've already influenced the process. That's a one-word, big, huge order of magnitude task. Once you meet them in person, I think it's a lot easier once you develop a little bit of taste. Is there a spark? And what kind of spark you're looking for? For what kind of role? Like if the person wants a job as you know, a job within a company, it's sort of a different spark you might be looking for. Or do they want to be a venture investor? The criteria is a little different of what kind of spark?
• Don’t aim for zero defects hiring. Same is true about finding founders too.
  • Well, the first one definitely happens. I mean, look, this is not zero defects. So if you're gonna do zero defects hiring for your company, or zero defects investing with your account, but some people do say they want to have zero defects in hiring. You can't do this stuff like you can't hire unproven talent. You're gonna make mistakes, and you just have to admit that you're gonna have false positives and false negatives. And it's like, what's the ratio of major upside to mistakes? Yep. Doubtfully, I've made one massive mistake. I made it at Square, which is really funny. I literally had the whole company, like the whole company, lobbying me to fire this person. This has never happened in my career before, six weeks in, from the top down from Jack to the most junior person, every single person was like, 'when are you getting rid of this person?' So you're clearly gonna make some mistakes, that's actually hard to do. And this guy's paper resume is actually pretty impressive. He would never get it if you defend this guy. Well, for a while, but like, I mean, literally, I've never seen this before. Like, when Jack's asking me everyday when you're getting rid of him. And like you have customer support people asking me to get rid of the person and everybody in between. So you're gonna make mistakes. And you have to be willing to admit that if you're looking for high potential people that haven't proven themselves yet. Yeah, founders, obviously all investors make mistakes. I mean, by definition, pick your favorite metric, but fundamentally looking for high outcome, high potential, high growth companies. If you do, you know, if you do the clinical baseball batting average of 300 or so, you'd be close to the Hall of Fame early.
• I highly recommend spending two years joining a high-growth company to learn as much as possible and apply them to your company. I believe there are diminishing marginal returns on learning after about two years.
  • There's different ways people learn, some people learn better by watching and some people learn by sort of, like, you know, thrown into the water, and they learn to swim, like, each person has a different preference on that. And so for people who learn by swimming by being told they're going to drown if they don't founded a company is not a bad way necessarily to learn. You don't know what you're capable of, and you'll pick up some skills by trial, and trying, other people would be terrified and literally drowned or fear, you know, go freak out about drowning. And it's a very bad idea to start a company as opposed to join someone else's company that's doing well pick up lessons, you know, sort of write them down and apply them. So I do highly recommend the two years sort of to fall to join a high growth company for two years, because I think you hit diminishing marginal returns and what you can learn in about two years. And then if you love the company, and you love your role and excetera, you can stay but like it's a two year commitment to learn as much as possible, then jump out and try found
  • One of the reasons why you learn so much in high-growth companies is that the problems are constantly changing. It's not a zero-sum game of allocating different problems to different people, because there are so many problems and you can't hire fast enough to fix them all. So you end up giving opportunities to people like interns, because you can't hire enough experienced support fast enough. This results in a high velocity of problems and a need for people to step up and conquer them. It's a great way to learn and get the chance to do things that you wouldn't traditionally get to do. That's why I highly recommend it.
• There are two philosophies on what to do when you draft a rookie quarterback: play it him right away or put him on bench for two years carrying the clipboard around.
  • There are two philosophies on what to do when you draft a rookie quarterback. Some people like to play the quarterback right away, even though they may have the worst year of their career. I actually have a chart that shows the stats of every famous Hall of Fame quarterback in their rookie year, and almost without fail, their stats are terrible, with more interceptions than touchdowns. Then there's another school of thought that suggests putting them on the bench for two years, carrying the clipboard around, so they can learn. Interestingly, quarterbacks who follow this approach tend to perform better in their first year of actual play, with good stats. However, they may have wasted two years on average sitting on the bench when they could have been learning. You can find Hall of Famers in both camps quite easily.
• If you want to find the steepest, most challenging slope, you need to push yourself to the limit. You should strive to be nervous and occasionally have sleepless nights about your work, because that means you're pushing yourself to the extreme, testing your abilities, and your body is reacting accordingly.
  • If you want to find the steepest, most challenging slope, you need to push yourself to the limit. If the slope doesn't seem that high, it's likely because you're not challenging yourself enough. You should feel nervous about it, just like in an old book I read when I was younger that made the case biologically. According to the book, your body reacts in a way that signals how challenged you are. If you don't feel nervous or break into a sweat, it means the task is too easy. You should strive to be nervous and occasionally have sleepless nights about your work, because that means you're pushing yourself to the extreme, testing your abilities, and your body is reacting accordingly. The book starts with an anecdote about Bill Russell, an incredibly successful basketball player who won about 10 NBA titles. It's mentioned that he used to throw up in the locker room before every playoff game.
• Identify an incredibly fragmented industry that is generally disliked by consumers, and disrupt it by vertically integrating, simplifying the process, and taking on the burden of achieving a high NPS score.
  • There's a common formulation that many successful companies follow, and if you can align with this magical formula, you have a shot at building a very important company. The basic formulation is as follows: you target an industry with very low NPS (Net Promoter Score) scores that is highly fragmented, and then vertically integrate with a simplified solution. This is a common denominator among companies like Open Door, Square, Uber, Forward Health, and other funded companies. The key is to identify an incredibly fragmented industry that is generally disliked by consumers, and disrupt it by vertically integrating, simplifying the process, and taking on the burden of achieving a high NPS score. While there are certainly other factors at play, I believe this formula works really well for building successful companies.
• My secret to productivity and performance is sleep.
  • It's great to hear that you prioritize sleep and recognize its importance in overall health and performance. Lack of sleep has been linked to a wide range of health issues, including chronic conditions and decreased cognitive function. While studying the impact of sleep on healthy individuals may present some challenges in terms of data collection, there is increasing evidence supporting the critical role of sleep in our well-being.
  • The book "Why We Sleep" by a University of Berkeley professor is a recommended read that delves into the topic of sleep in a rigorous manner. As our understanding of sleep continues to evolve, it's likely that more emphasis will be placed on optimizing sleep as a key component of maintaining good health and performance in various aspects of life.
• To be good at strategy, you need to understand the core business equation. Different knobs that contribute to success, the connection between these knobs, and how to optimize business without pushing them past their limits.
  • Generally, every business can be reduced to an equation. It's not necessarily literal math, but it's a useful way to think about it. As you turn one knob, there are other knobs that ultimately contribute to success. Strategic people understand the connections between these knobs, so they don't just keep trying to turn one knob past its limit. They look for other ways to optimize and make things work. It's like system engineering or systems thinking, which is how Elon Musk, Steve Jobs, or Jack Dorsey are sometimes described. It's about understanding all the connections and being able to talk about the other moving pieces of the business, not just optimizing one specific metric like CAC (Customer Acquisition Cost). Functional executives who can do this are rare, as most only focus on their own area of expertise. This ability to see the bigger picture and understand how different parts of the business interact is a key test of strategic thinking
• “Seven Powers” helps you to understand that is truly strategic and what is not.
  • I highly recommend the book called "Seven Powers" which I've tweeted about multiple times. It provides a rigorous definition of what strategy is and isn't. After reading the book, you'll have a framework for having specific conversations with your team about what is truly strategic and what is not. It's a useful tool for recruiting and aligning your team around a common understanding of strategy, rather than having generic and abstract conversations.
• As a manager, judgment involves the ability to calibrate one's depth and water wisely, and proactively seek assistance when necessary to avoid accidental drowning.
  • To me, judgment means understanding how far out on a limb one is. As a leader who has managed many teams, I believe that giving people responsibility is fine as long as they know when to seek help or come back to me if they are in danger of drowning. Those who have good judgment are aware of their limitations and are willing to rope in colleagues, mentors, advisors, or board members for assistance when needed. On the other hand, those who try to solve everything themselves without seeking help may find themselves in deep water with limited options for fixing the situation, which can lead to detrimental consequences. Judgment involves the ability to calibrate one's depth and water wisely, and proactively seek assistance when necessary to avoid accidental drowning.
• Try to managing and scheduling yourself and reflect on priorities and make adjustments as needed. When you delegate your calendar to someone else, they may not have the same level of understanding or fidelity to your priorities as you do.
  • When you delegate your calendar to someone else, they may not have the same level of understanding or fidelity to your priorities as you do. They may end up inheriting someone else's time allocation and it's challenging to train them to be the same proxy as you would be for yourself. In my career, I didn't have a system for calendar management until 2012 when Jack insisted that I get one. He pointed out that when people want to reschedule meetings with me, it creates cognitive overload for them to track me down and interferes with my busy schedule. Having an assistant as the interface for scheduling can be helpful in managing these disruptions. However, there is a risk of becoming addicted to turning over your calendar to someone else, as it may result in loss of control and insight into your own priorities. Some of my successful venture investor friends do not delegate their calendars, and I still try to manage some scheduling myself because I can reflect on priorities and make adjustments as needed, although there are limits to what I can do.
• You have to make a decision on what is the most important priority for you in this decade.
  • As far as subscribing to Bezos' view, which is at best, their harmony, if you try to trade them off, I think you can achieve an optimal balance of both. And you have to make a decision, which I believe everybody should decide for themselves, on what is the most important priority for them in this decade. And you can change it, as one good thing is that it's editable every so often. But like all decisions, as Reed Hoffman puts it, when you want to make a decision, optimize for one variable, don't make a pros and cons list with pluses and minuses. So if your goal in life is to change the world, that has certain consequences and impacts how you make decisions. If your goal is to make a lot of money, that has certain consequences as well. And if your goal is to raise an interesting and well-rounded family, it's important to prioritize and figure out what your goal is and what your purpose is, and then make decisions based on that foundation. So when it comes to work-life balance, it essentially means you're making decisions based on a summation of columns, rather than strictly figuring out what's most important to you.
• I do believe that almost everything comes with trade offs in life. And you want to make the trade off smartly, like not in the grass is greener sense where you're naive about it. I help surface the trade offs for founders and say “you get to make the decision.”
  • There are trade offs. I do believe that almost everything comes with trade offs in life. And you want to make the trade off smartly, like not in the grass is greener sense where you're naive about it. But there's real trade offs and make them consciously and that's a lot of what I do with founders. They'll ask questions like, “Should I switch to a functional organization?” or “Should I have a growth team?” All these answers are complicated and they have trade offs. And the only thing I can do is help surface the trade offs and say “you get to make the decision.” I can highlight for you the things you might not know that will eventually play out. And so you can make a more informed conscious decision.
• My general belief about startups is that you start with a vision of what you want to accomplish. And then you figure out what kind of characters you need to write the script.
  • My general belief about startups is that you start with a vision of what you want to accomplish. And then you figure out what kind of characters you need to write the script. First, you're like, "Okay, what kind of characters do I need to make this script successful?" Just like some movies would have been complete bombs if they had different actors, and some movies, actually, you know, a particular actor or actress was able to carry the whole movie. So you've got to figure out what talent you need, and then you go recruit those people, and then you finance it, just like producing a movie. You need to get the resources to put it on, and then you create a trailer, which is like the marketing campaign. And then you build it, and then you sell the tickets. That's my view. I don't believe you should do this piecemeal.
  • To be more specific, depending on what kind of movie you're going to create and what the roles are, you definitely want different people. Like, you can imagine Rocky being a total disaster if Sylvester Stallone wasn't like the character. And then there are actors like Meryl Streep who can pull off roles that probably any other person on the planet would absolutely fail at. So you just need to know what you really want, and then you have to assess it.
• Probably half of founders get into serious disputes, which shouldn't be totally surprising because half of marriages end in failure too. You can test it by brainstorming together and making a list people and ask each other opinion about them.
  • The process of working together is interesting and very challenging. It's not surprising that about half of founders end up in serious disputes, because about half of marriages end in failure too. Humans are not very good at predicting long-term relationships. Starting a new startup is similar, as humans evolve and change, and you can't expect anything better than you would from a marriage. So you may just have to take that kind of risk. However, there are ways to test things out, such as using values-based assessments. For example, Jack and I did this when we started our company in Silicon Valley. We made a list of people we knew well and assessed them without giving each other a heads up. It was a good way to see how our brains process and evaluate people, because if you're going to run a company together, you can't have a wide discrepancy in your assessment of people and work well together. So being consistent in your evaluations is important. You can test some of that out by doing a project together, but I'm not sure if that really is a good proxy because you don't always see what people are truly like in that context. It is a good way to sort of see how our brains process, because if you're going to run a company together, you really can't misgrade people by more than about half a grade and work well together. So I can give you an A- with encouragement, and hey, that's constructive. If we have a VP of Engineering who thinks this person is awesome, and I think they are terrible, it just doesn't work. And so you have to be very consistent with very few shades. You can test some of that out by doing a project together, but I'm not sure if that's a good proxy because, as I want to stress, you don't really see what people are like.