How To Achieve Mastery (And Why You Don’t Have To Be Born With It)

How do you master mastery? Best-selling author, Robert Greene, recently published a book on the topic and the book is called Mastery.

It’s full of great stories about the development of masters, like the Noble Prize winning physicist, Albert Einstein, and the pioneer start-up investor and mentor, and Mixergy interviewee, Paul Graham, tons of great stories and lots of good research.

Robert Greene

Robert Greene

Power Seduction and War

Robert Greene is an author and speaker known for his books on strategy, power and seduction.



Full Interview Transcript

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Hey there, freedom fighters. My name’s Andrew Warner, and I’m the founder of, home of the ambitious upstart, and the place where we study success, study entrepreneurs, and we use what we learn to build successful companies. Hopefully, if you’re watching me and using everything that you’re learning, you’ll one day build a successful company and come back here, and let me interview you, and help you get there. In this interview, we’re going to be talking about how to achieve mastery. Best-selling author, Robert Greene, recently published a book on the topic. And the book is called “Mastery”. It’s full of great stories about the development of masters, like the Noble Prize winning physicist, Albert Einstein, and the pioneer start-up investor and mentor, and Mixergy interviewee, Paul Graham, tons of great stories and lots of good research. Robert, Welcome.

Robert: Thank you for having me, Andrew. My pleasure.

Andrew: I love this book. And at the same time, I can see that if I recommend a book on mastery, and I even suggest that they watch this interview, I can anticipate their objection which is some people are just born great. One of the examples in your book is Bill Bradley. I looked up his Wikipedia page to see just how much the guy did. He’s a hall of fame basketball player. He’s a Rhode Scholar, a three term senator from New Jersey. The guy’s just [making sound like machine gun] pa-pa-pa. It seems like everything he touches, he just naturally does well at. So maybe some people are just born that way. What do you say to that?

Robert: Well, I have the story of Bill Bradley, because I’m a basketball junkie myself. Probably around the age of eight or nine he fell in love with basketball, like a lot of kids did, the sound of the ball swishing through the net and all that. And he was tall, even at a young age, but he was pretty uncoordinated. He was slow. He wasn’t a great dribbler. He couldn’t jump very high like a lot of us white people, but he loved the game. And what Bill Bradley did was to initiate the most intense, ridiculous, insane, obsessional, practice schedule that, I think, any athlete has ever devised. He did what is known in the field as deliberate practice. I call it resistance practice. Where everything that he wasn’t good at, which I just mentioned, dribbling, passing, rebounding, almost all of the skills in basketball, he practiced on. And so, for instance, he practiced dribbling in between chairs like we’re all taught to do. Then he put on these glasses which made it impossible for him to look down and see the ball, so he would always be looking up when he dribbled. He did this hour after hour, after hour. When he would be at home in his bedroom, he would be practicing different pivot moves, that kind of thing. He would practice every day for this amount of hours. His family goes on a vacation on a cruise ship, he’s dribbling the ball up and down these narrow corridors with those glasses, so he could practice dribbling in that environment. And slowly, he transformed himself into this incredibly graceful, amazing, basketball player who is known for the fact that he could. He had eyes in the back of his head. He could make the most incredible passes and when he finally got the NBA in the New York Knicks. People who watched him go, “This is the most. This guy must be naturally gifted. How could he make such passes? He’s an artist on the court.” It wasn’t artistry that he was born with. It was an insane will to overcome his limitations and to practice, practice, practice, practice, practice, practice until he became a great star and he applied that everything else in his life. Academics. Politics. Etc.

Andrew: I wonder about you and your practice. I love this book Mastery. I actually blew off so many other things because I just wanted to sit with my Kindle and read it and to me it feels like you’re a natural writer. You’re a guy who just absorbs stories from history and then you synthesize them and then you come up with patterns of success and then you teach them. How did you get to this level? What kind of practice did you go through?

Robert: Well, it’s a similar Bill Bradley story because you know, I. Prior to writing this book, and all of my books, I went through a rigorous apprenticeship. In “Mastery”, the apprenticeship is a very important concept that I talk about. I, as a writer, went through a very elaborate apprenticeship, trying my hand at journalism, then working in film and television in Hollywood, constantly learning how to write, working with a deadline, researching skills, organizing, but it wasn’t meshing with me. It wasn’t a good fit and then I found writing books. I got this opportunity and I call it. In the book, you’re life’s task. This is what you in your life you were meant to accomplish and I go into great depth because I say you’re not going to master your field unless your passionately, personally engaged in it. I encountered my life’s task at that point. I’m built to write books. I’ve got a brain that likes to organize large amounts of information. OK. Now, it was a good fit but I have an intense amount of labor to make these books work and so it’s not something that just flows out of me. I do incredible amounts of research. I want you to read the book and not have to feel that the labor I went through. I want you to read and it go, “Wow. This flows and everything.” But behind all the scenes, I’ve spent thousands of hours accumulating information, putting an elaborate notecard system that I could even show you here on air. It makes me look like a mad man.

Andrew: Do it. I’d like to see that.

Robert: OK.

Andrew: Oh, this is fantastic and I do want to come back and ask you about apprenticeship because I keep asking people, why would anyone want to mentor a new entrepreneur and your answer’s so much better than I’ve ever gotten. How does it work? How do you organize the stories in there?

Robert: You see that?

Andrew: I see it. Yeah. It’s an index card system. I see all the letters. I see little colored slips of paper sticking out. How does it work?

Robert: Well, basically, I read a book and I take, as I’m reading it, I underline it and put notes on the side and then I go back and put them on notecards. And I can gauge a good book will generate 20 to 31 notecards. A bad book will generate two or three notecards and I will find themes in this book and I will take a book that’s maybe no organized very well and I will do the organizing. On page 30 you talk about this and you talk about it on page 180, you should have put those two together but I’m going to put those two together. And I find the themes in there and I break the book down into the gist of it, the heart of it. And, I categorize it later as I move into the process, I see these themes and patterns that you were talking about that an apprenticeship, creativity, working with a mentor, social intelligence. Slowly the chapters come to life and I’m now able to organize it in various chapters. Each part has the title of the book on it and is color coded, have different colors of cards, depending on the kind of subject that I’m dealing with. If it’s the arts, science, politics, etc. It’s elaborate. You don’t want to know everything about it, but with this there now, if I’ve done all that work and I sit down to write, I have at my fingertips, all of this. If I want to do Leonardo da Vinci, I have 50 notecards that break him down from every possible angle. I can now, with that, write in a much fuller, deeper, dimensional way because I’ve taken all this information and I’ve organized it.

Andrew: So, if you might read a story about Leonardo da Vinci and how he learned, you would put that story down on an index card and the main message from that story.

Robert: Yeah.

Andrew: His way of learning is writing things down with a pen and paper, something.

Robert: Yes. And, so the one book Leonardo da Vinci may generate fifty cards because it was a great book. [??] biography of da Vinci and those fifty cards are in to different categories. So, I used him to illustrate the life’s task but now later in the book when I’m talking about creativity, I have other cards about Leonardo da Vinci that complete the story so I can use these people throughout the book.

Andrew: And you say we do need to, we need to find that thing that we love. Almost on a religious level is the way that our passion should be. How do we find that out? How do we find what makes us as passionate as writing makes you?

Robert: Well, the first thing that you have to understand is the concept itself. So, if you internalize what I’m talking about, now you’re going to be motivated to go through the process and essentially, I’m saying, now in the world that we live in today, you have a possibility. The political, social, technical barriers that used to keep mastery as this little domain for only certain numbers of people is all exploded. You have the potential now to follow what excites you in life. What we would call your vocation. The word vocation is related to the Latin word for calling. It’s like a voice you hear in your head. OK. So, you’re not going to get very far in life if you don’t follow a path that somehow meshes with these deep interested that you have because the way the brain is operates, you’re not paying deep attention. You’re not learning intensely if you’re not engaged emotionally and we know that about how the brain functions. So, all of the people that have really, really mastered their field, who have incredible success are deeply connected to this uniqueness, to this sense of vocation. So, you have to be, first of all, grounded in the concept. If you go into law because your mother and father told you you needed to be a lawyer, young man, but you’re not really into it but it seems good because the money’s good. And you follow that path and it doesn’t connect with you, you can fake your way in your twenties but as you get 34, 35, 36, you’re disconnecting. You’re not paying attention. You’re not learning as much. You’re going through the motions and you’re going to pay a steep price by the time you hit 40, you’re going to be depressed. You’re going to start drinking. You don’t even know why. You’re not, you deviated from what you should be doing. So, grounding yourself deeply in that, you know, now that you’ve got to find your way before it’s too late to something that meshes with this natural, these primal inclinations. I call them primal inclinations and I show in the book that the fact that you were born unique which is a scientific fact, the way your brain is configured, your DNA, is shown in your early, early childhood by the fact that you’re drawn to certain things. You’re drawn to books. You’re drawn to music. Sports. Ways of thinking. Mathematics. History. It’s before your parents start infecting you. Before your friends started telling you what was good. It’s like this natural thing you’re drawn to. All of that is there within you as you get older and older. You’re not hearing it. You’re not paying attention. I talk in the book about how to reconnect with those earliest inclinations. How to find them again. How to notice the certain subjects that have that primal attraction to you.

Andrew: What’s one way to do that? To reconnect with it? I remember the story you told. I highlighted it for myself about Albert Einstein and how when he was a kid, his father gave him a compass as a present and he was just transfixed by the needle and he wondered about how it worked and that set him off on a passion that helped him for the rest of his life. What’s one way for us to reconnect or to even remember that passion that we had that could lead to?

Robert: Well, I’ll tell you. Something funny happened to me a couple of months ago. I was flipping through the New York Times and there was an article about recent findings on our earliest ancestors, going back a couple of million years. And I realized that God, every time, there’s an article like that in the New York times, I’m so drawn to it. I don’t know why. I’m just so fascinated with any kind of findings about our earliest ancestors. And then it made me realize, you know, I was like that when I was six or seven years old. I had this insane interest in deep, deep pre- history. And I even wrote a novel when I was eight years old about the earliest human beings. I mean it’s dreadful. No one would want to read it, but the point is, that happens to all of us. There’s going to be something today when you get on the internet when you’re surfing or you open a newspaper or a book or whatever, where God, I really want to know more about that. I’m going to get another book on it. It stimulates your desire to learn and you’re curious and no one has to prod you and I bet, I have been doing this for a couple of months now, I can take anybody out there who says they don’t have that and I can help you find it.

So they’re still there in you. It’s like a fire that’s gone out, but there are still embers and you can find them again in that process. I also tell you to pay attention to things that you hate. You mentioned Paul Graham who’s one of the great masters that I interviewed and I didn’t realize he was on your show. He’s amazing. One thing I talk about Paul Graham is he had what I called a hacker’s apprenticeship and a kind of hacker approach to finding his life’s task. He didn’t really know what he wanted to do. He did computers. He then went into art and then finally it all meshed together when he was 30 years old and he created Viaweb. But the thing that Paul told me was a lot of it was finding out what he didn’t like what he hated. He hated academia. He hated the bureaucracy and the politics. He hated software consulting and the whole crap of salesman running, which should be run by the engineers, etc. He hated working for a large company. That shows you what you love. It’s a flip side of what you love. So for him what he loved was working for himself, not having to deal with the bureaucracy, having direct contact with his own audience, with the users of what he creates, on and on and on. So signs of what you hate are something you need to deeply pay attention to. There are many ways to mind this. The most important though is to take the time and space to look at yourself and examine it and not be constantly in the Facebook and everything worried about what other people are doing. You’ve got to go into yourself a little bit.

Andrew: I want to come back to Paul Graham and talk about one other thing that he hates relating to interpersonal communications, but one more thing before I….well here’s where I’m thinking we should go. I want to talk a little bit more about maybe even drilling deeper into your passion and then I want to talk about the apprenticeship because the way that you talk about it is so interesting and useful and then we can come back and talk about Paul and the way that he relates to people and even Benjamin Franklin and the way that he learned to relate to people. So when we find our passion, you say niche it down to something that’s so unique that no one else would ever be able to master it the way that you do and you give the example of… the childhood example of let me see if I’m pronouncing his name right, V. S. Ramachandran?

Robert: Yes very good.

Andrew: Thank you. V. S. Ramachandran. So how did he do this as a child and then later on as an adult?

Robert: Well he’s a great example. He’s one of the contemporary masters that I interviewed and he’s a great neuroscientist, written some really interesting books and he growing up in India realized that he was a strange young man who loved strange phenomena in nature. So he studied seashells that he collected when he was 8 or 9 but he liked the weirdest kinds of sea shells and he liked studying human abnormalities. They had a museum in India where they showed…they had in bottles all kinds of birth defects sort of thing and his eyes lit up at like all of these strange human forms that had kind of [??] in the womb. So he’d always had a passion for the outlying areas of phenomena in any field and he didn’t know really what he wanted to pursue. He went into a medicine because his father said you could be a doctor and you can you know it’s a great way to start at least and so he started medicine, but he realized what excited him most was psychology and optics and the psychology of perception. So he gets into that as now he’s starting to find his way towards his life’s task. This is a more specialized realm of science that he can now go into optical illusions and then he finds a great mentor in this man named R. O. Gregory who’s sort of a pioneer in the field and now he becomes a professor after going to Cambridge of this visual psychology, but he discovers that there’s still something else even narrower that excites him and it’s not just visual psychology, it’s how the brain itself functions and these extreme abnormalities of various brain diseases or brain disorders things like people who have a brain disorder where they no longer recognize their family members and they can’t recognize people’s faces, the weirdest kinds of things.

He finds this insanely specialized niche about this very peculiar element of the brain and disorders and it fits him so perfectly. It’s just like when he was a child. It’s a perfect fit because it’s not about these various syndromes, like the one where you don’t recognize your parents, or you want to have your leg amputated even though your leg is perfectly fine, it’s about how the brain itself functions. Through mining this very narrow subject, he’s able open up all kinds of questions about the origins of language, how the brain itself works, our notion of who we are and our bodies, etc. He found his way slowly to this one niche, this one subject of study that was so suited to him that he could master it and he could create this kind of personal empire that he could dominate. Oddly enough, it’s kind of something that I’ve done for myself because I found writing books in this particular way with the stories that I tell, there are no other books like that out there. You might not like them, but you could honestly say, “I found a niche that no one else is occupying” because nobody writes them the way I do, and that has freed me up to now explore that niche and go as deeply into it as I want.

Andrew: I can see maybe in my world I might start out saying, “I’m interested in entrepreneurship. Great! I’m going to study entrepreneurship and do interviews with entrepreneurs.” I’m thinking, “That’s too broad. I can’t master and be the best person in the world at it. I’ll go smaller, tech entrepreneurs. No! Still not small enough. Smaller still. I’ll go to mobile phones. Still not small enough. I’m going to go towards… Well, that one’s doing Apple. I’m going to focus only on Android and only on a specific kind of Android and specific…” Then I become the absolute master of my personal empire as you call it. What if that personal empire that I’m now the master of is not big enough? What do I do?

Robert: Well, the trick in the world today is not to… There’s the fable of the hedgehog and fox. The hedgehog is only good at one thing, and the fox is good at many things. I think we live in a world where you need to be a bit more of a fox. You’re learning several skills.

Ramachandran learned several skills. He learned medicine, began to train as a doctor. He learned optics and visual psychology. Then he went into neuroscience, and then he went in this, the brain. You add all that up. That guy’s got five or six insane skills. So, if for some reason it doesn’t work out studying this niche in neuroscience, he can now transfer to something else.

It’s not a question of finding the one little niche with Android. It’s who are you, Andrew, that what is about Android that excites you? Why did you choose that one thing? It’s got to be a little bit larger than that, and your skill base has to not be just on one thing because we live in a world where the future lies with people who can learn five or six different skills or fields and combine them in a unique way. It gives you flexibility.

I have in the book the woman, Yoki Matsuoka, who’s one of my favorite (?) interviewed. She went into electrical engineering, and then she discovered she wanted to do robotics, and then robotics led to artificial intelligence, which then led her to decide she wanted to go into neuroscience. Then all of a sudden now she realizes she can design a prosthetic hand that combines all of that knowledge and made a hand that actually connects to the human brain. That’s the paradigm for our times. You combine them to create something that’s uniquely them but also their own personal empire, no one else could be better.

Robert: Who could do what Paul Graham did with Y Combinator? Who could create something so strange, so weird, such a mirror of his own weirdness, you know? He found his way to something that’s now worth $5 billion and it’s immensely successful. He hacked his way to a business model that is a reflection of himself.

Andrew: Investing only in small entrepreneurs, only in the kinds that have small startups that some people might consider features, not real businesses, having a small operation, and so on. Not being so human- centric, being much more intellectual.

Robert: Also, all of the lessons that he learned along the way when he was creating Viaweb and his ability to judge peoples’ character, not just their resume having graduated from Harvard. He’s saying, “All the lessons in the book about your. . . Are these people deeply engaged with the startup that they’re trying to create or is it just about money?” He’s able to create an apprenticeship system based on his own apprenticeship.

Andrew: Speaking of apprenticeship, one of the stories in your book, “Mastery” that I just kept highlighting lots of sections of because it was so interesting is Michael Faraday and how he got his mentor, but before he even got his mentor he had to develop himself to the place where he could be worthy of a mentor and you say that too. You have to get good at something and then you can go out there and get a mentor right? And the way that they did it was by reading a book called “The Improvement of the Mind”.

Robert: Right.

Andrew: Why did that prepare him to get a mentor?

Robert: Well, the story of Michael Faraday is so good because he comes from the poorest part of England. His father is a blacksmith and we’re talking about the early 19th century. If he wanted to be a scientist you had to go to Oxford or Cambridge in order to get access to a laboratory. Michael Faraday has no education, no access to education. It’s like, how can you possibly do it. Well what’ so interesting is that he wanders into a book store and he impresses the guy who owns this book seller and a book binder and the guy offers him an apprenticeship as a book binder and it’s like the perfect place for him to educate himself. So now he’s surrounded by books that he’s binding but he can read and one of the books that comes in there is called Improvement of the Mind as you mentioned this really interesting 18th century self-help book and it tells him this is how the brain works well before any neuroscientist had discovered it. The human brain works by doing by actually practicing what you learn. You just don’t passively absorb information. You conduct these scientific experiments yourself.

You go to lectures and then you write down the lectures and you write down what the person said and then you write it down again so it’s engraved in your brain. He takes everything that this book says and he takes it three or four steps further and what he does is he created his own encyclopedia of science. We’re talking about a 16 or 17 year old kid based on all of these lectures that he starts attending meticulously with drawings because he taught himself how to draw. It’s so elaborate and beautiful that it impresses a man who wanders into the book store which then eventually leads to him getting an apprenticeship with the only man who could ever let him now into this exclusive club of scientists. An insanely remarkable story of persistence and hard work and diligence and intuition, but Michael Faraday would have never gotten this position as an apprentice to Humphrey Davey if he didn’t demonstrate already that he was a very diligent, conscientious, hardworking young man. That’s the point. That’s the lesson that I’m trying to tell you.

Andrew: And when he got that apprenticeship he didn’t start out by studying science under the master he started out you said by cleaning bottles, by sweeping.

Robert: Yes.

Andrew: You know what? If I got to meet my hero and he told me you know what you should get my lunch every day because I need to focus on my work and at the end of the day make sure that my car is you know de-ice it and make sure that it’s sitting right out front and then drive me home, I would think this guy doesn’t get who I am. I’m going to go off into the world and build something on myself and then make him regret that he made me get him his sandwich and you’re shaking your head even as I say this. Why is that the wrong attitude?

Robert: Well, I call it submit to reality. There’s chapter number 2 and it’s about the apprenticeship and I’m trying to say look, you enter the work world and you’re a naive young man who has no skills and you’re full of ego and you think you’re great and you’re not great because you don’t know what you’re doing and you don’t know how the world operates. You’re full of ideas that are not realistic. It’s not a mark against you. It’s just that’s the way it is. So shut up. Shut your ego down and start to learn and observe and it’s actually a valuable lesson to be able to simply observe other people, do hard work, not think about fame or attention or money. And one of the life skills I think people need in their 20s is how to live without a lot of money. Paul Graham talked about that. If you’re constantly worried about the pay check when you’re 23-24, you’re going to be addicted to the pay check your whole life. The sense that you know that you can do without it, that you can get by on little amounts of money which I did when I was in my 20s is a great life skill that you’re going to need later on because you’re going to go through periods where you’re going to be asked to do a job for free. You’re going to be having to start your new business without a lot of capital, with a high level of risk. It can fail and you’re thrown back to square one. You’re not afraid of that. Fear is a terrible element for an entrepreneur. If you feel like damn it if it fails I’ll get back on my feet, I knew when I was 23 what it’s like to live on you know five dollars a day. I’ll go back there. These are the things that you want to calm down. Your desire for attention and you’re saying, “Fuck you. I’m going out and I’ll get your sandwich.” That’s bad. You’re not starting off on the right foot.

You are submitting to the fact that you are an ignorant, unrealistic, naive person that needs to absorb this knowledge and once you get there, you’ll be the one to rewrite the rules. Then you’ll get your revenge ten years down the line. You’re going to rewrite the rules. You’re going to outshine that master that you had before. You’ll outdo him but you’ve got to calm yourself down and you have to de-ice his car, if that’s the only thing you’re doing, then you have no opportunity to learn. Michael Faraday had to clean the fireplace and clean the bottles and also help set up the experiments. So, for the two hours a day that he was helping Humphrey Davis set up the experiments, he observed him and learned. And then the other four hours, he was doing menial tasks. You need to be able to put up with the menial stuff.

Andrew: And maybe even I’ve been persuaded after reading this section in your book. Maybe even it’s better to be the guy who just cleans up because then you get to observe without having to think about your own production and having to hit certain goals and observation is one of the most important parts of an apprenticeship because.

Robert: Well, there are so many things you have to be able to observe. So, you enter a new world and there are all kinds of rules and procedures. There are political and social rules that nobody writes a book about and hands you when you enter corporation X. It’s all unwritten stuff. You want to be able to look and see this is what somebody did and they got fired for it. This is what the boss is doing and why he is getting promoted. It’s like you’re in a foreign country and you’re just watching the various figures and how the power game is going. These are the skills I need to get. This is the skill that’s really important and in any business, there are skills. It’s not just tech manual skills. There are social management skills. These are the skills that are important here. All right, I’m going to observe the person who’s most skillful in that office and I’m going to learn by imitating and practicing the way they’ve practiced, on and on and on down the line. You know what happens to a lot of people? They don’t think like that and then they go and get a job where they get a really good paycheck because that’s what they’re thinking about and they don’t, in a large company or whatever and there’s pressure on them immediately because money is involved.

The more money’s involved the greater the pressure to perform and the don’t have the skill level, yet, to perform at the level that they’re expected to and that creates a lot of pressure and the pressure means that you don’t learn what you need to learn, you learn how to kind of get by, how to BS your way through it, how to be political, how to be social. It’s better to take a job in a place that pays half of what you think you deserve where you can learn and you can ground yourself in skills and basically turn yourself into this observing beast. Because later in life that ability to watch people and observe them, to observe how the rules of the game, you’re going to be needing that for your whole life. You know, and if you don’t develop that in your twenties, I think you’re getting in trouble.

Andrew: When I ask entrepreneurs why would you mentor someone, they always say, “It’s because I want to give back. It’s because we just like to help.” But I don’t buy that as an interviewer. And I think it’s not their fault and I don’t think they’re lying. I don’t think I’m asking the right question because to me what you’re saying, and master rings true which is they’re not doing it out of the kindness of their hearts. The reason that they will mentor you is you do something for them that appeals to their self-interest. You clean them for them in a way that no one else can. You pay attention to them in a way that no one else has the patience or the willingness to. Right?

Robert: Well, I don’t want to say that there’s not a small element of altruism in there. There could very well be and it is an emotionally satisfying relationship to give another person your experiences, to help them to learn from the lesson you learned, but there is a very deep level of self-interest involved. It’s like a parenting relationship where now you get to kind of help guide that other younger person and it’s a satisfying feeling to be able to do that but also they’re helping you do the small tasks that you don’t want to do. I had, we’ll talk about it later, Ryan Holiday is my apprentice. He’s doing some of the research and he did some of the organizing of the interview for this book that I’ve quite frankly, didn’t want to do. He showed to me that he could do that. So, it’s not like I’m getting slave labor. I’m giving him something in return. I’m teaching him writing skills, and I’ll be there for him when he wants to become a writer. But yeah, I’m getting things out of him.

Paul Graham created Y Combinator partly because he wanted to give back what he learned, but what happened in giving back what he learned, he got a $5 billion business. He takes 10 percent of every company — I think it’s 10%, I’m not sure — of every startup that he actually helps found.

You don’t want to divorce the self-interest. We are all creatures, particularly in business, we are all motivated by a great sense of, “What’s in it for us?” You’re looking at a mentor and you’re saying, “I can give this person something. I can save them time. I can help organize their desk.” It’s got to be on that level.

Andrew: We’ll get into, in a moment, the importance of working with people if you want to achieve mastery, and how self- interest fits in there. Let’s talk now a little about Ryan Holiday. You don’t talk about him in your book, but he’s the guy who introduced us. Before the interview started, you and I chatted about him.

Robert: Yeah.

Andrew: I didn’t realize that he was your apprentice. How did he connect with you?

Robert: I met him through someone named Tucker Max. I don’t know if you know Tucker.

Andrew: I interviewed him, too. Probably Ryan, yeah actually, definitely Ryan Holiday introduced me to Tucker.

Robert: OK. Tucker’s a fan of my books, and I met him and Ryan was with him. Ryan was 19 years old at the time. He was very interested in working, maybe as a researcher, on one of my books, so I gave him a few things. I could see, the main thing I saw was that this was a serious young man. It wasn’t about charming me, he wasn’t trying to be friends. He was very serious, and he liked reading books.

OK, so number one, he had two good things in his favor. A lot of times I’ve hired researchers before who maybe have bigger, fancier degrees than him, but they didn’t have good character. They were about money, they weren’t about the work itself.

Then, I had a problem with my Wikipedia page. Ryan said he could fix it, and that was impressive. He had real internet skills. You know, he’s 19, he has those skills. It’s in his blood. I’m on the board of directors for the company American Apparel, and Dov Charney, the CEO, he was having problems with his Wikipedia page. I said, “Oh. Here comes Ryan. Ryan to the rescue. Ryan can do it.” Dov was immediately impressed and hired Ryan to be in the marketing department.

Basically, I’ve helped Ryan, because he wants to be a writer, hone his researching skills, hone his writing skills while I’m getting back these things. He’s covering up my own weaknesses. For me, as someone who’s in his 50s, I don’t know the internet that well. I know it fairly well, but compared to Ryan, I don’t know it at all. He’s covering up my weaknesses. He’s handling my internet promotion for this book.

That’s another great thing that you’re offering the mentor, you’re younger, you understand something that the older person generally doesn’t have a clue about. It’s this very mutual beneficial relationship, but it’s based on the fact that I’m a master, or someone who’s mastered something that can give him something, and he’s somebody who has real skills and has real character.

If you’re looking for a mentor, don’t try to think that what you need to do is just to impress them with your nice personality. You have to have something already there to offer them. You have to show a body of work, somebody else who can give you good reference that displays the fact that you have the right character, that you work hard, that you’re organized, that you can help him or her.

Andrew: Along the way, as a mentor, how do you make sure that your protégé, that Ryan, gets what he needs out of it? When you’re focused on writing your book and you just have a guy who’s going to do research, you don’t want to coddle him, but you also want to give him the learning that he’s looking for. You want to give him the guidance that he came to you for. You want to give him the personality that he wants to emulate. How do you make sure that there’s a back and forth along the way?

Robert: Well, the first thing, also, you have to be careful of, I know when I’m looking for a mentee, is that they can take criticism. I’m a nice person generally, but I want to be realistic. I want to tell you, “No, you didn’t get that right. You read that book, but that’s not what I’m looking for.” Ryan, early on, demonstrated he doesn’t take criticism personally. I can’t tell you what a great thing that is. It’s so impossible to work with people who take everything that you say personally. That’s rule number one, if you’ve got that insecurity, try your hardest to weed it out.

I’m very aware of the fact. . . You see, if you give somebody something on that level, like he’s giving to me, I naturally will want to reciprocate. Maybe, that’s me. There will be other people that won’t. If you’re with a mentor who isn’t like that, who’s guarding all of his trade secrets, who’s not helping you, that’s not a good relationship and you need to get out of it and I talk in the book about bad mentor relationships. Where they’re putting you down. They’re making you feel small. They’re not helping you. They’re just using you for slave labor. That’s a bad fit and that’s not what you want. You’re not a slave. You’re there to learn. I gave him opportunities to learn. I’m giving him books. In the beginning, I’m giving him books to research that are not the best books because I’m saving the best books for myself. He demonstrated that he was patient. He knew that I was giving him kind of some of the boring stuff. He didn’t complain. He did it. Now, I’ll give him more interesting books because he showed me things. All right. Now, he wants to write a book. I will help him with the proposal and I’ll help him connect with an agent. He’s showing me things. I’ll reciprocate. That’s kind of how it works and if you’re not getting that from your mentor, then find another one.

Andrew: I saw one entrepreneur who showed me a spreadsheet that he uses to make sure that every week he gives back to the people who work for him. And you know it was completed over time, but I don’t have that kind of anal tendency where I can sit with a spreadsheet every day to make sure. So, you’re just saying it’s not formal. It’s not that structured. It just happens. You just make sure that you give back. That you understand what he’s looking for and that you’ve given some of that.

Robert: I think that you could ask questions. And Ryan does. And you can come. It’s all got to be moderate. If I’ve clearly seen that he’s only doing this for himself and that he’s not really thinking about helping me, then I’m not going to want to have somebody like that around me. It’s an organic process. It’s not something that I would put on a spreadsheet or you know have a formula for. It occurs naturally over time. I talk in the book about how the human brain is designed for learning by watching, by absorbing other people’s energy. So through that process, he’s learned how I research a book. He’s learned about my notecard system. I didn’t even have to tell him that. He sees it. He sees how I break a book down. He sees when I criticize him for you didn’t find what I needed in that book. He’s now able to learn. Ah! I didn’t give him what he needed on that book. Now, I know better what he needs. It’s a communication thing and it’s the fact that as I said you’re observant, there are signs that I’m emitting. This is what I like in a researcher. Are you paying attention to those signs? Are you observing? Or are you focused on your ego? That’s kind of all about the apprenticeship and how to work with a mentor.

Andrew: What I’m seeing here in this relationship is interpersonal skills. I used to think of masters as brilliant people who got to do what they want. In fact, they got to be jerks to people because they’re so good. They didn’t have the time to be nice. They shouldn’t waste their time understanding your sensitivity and catering to it. Or understanding what it takes to speak to you in a certain way. No. They are brilliant. They’ve got to do it. And you have a whole section in your book that says, No. That’s not the way it is.

Robert: Well, look. Mastery is master. And you’re going to bring to it your own personal traits. So, there are examples of masters that quite frankly are assholes that aren’t good in dealing with people. You know. Maybe Steve Jobs falls on that line of the spectrum.

Andrew: That is exactly the kind of person that I would imagine is the typical master and his approach to other people is the typical, is the best approach if you want it. And you’re saying, no. It’s one person’s but that’s not the way to go.

Robert: OK. Well, we’ll get back to the social intelligence but just looking at Steve Jobs himself, he went through his first ten years or so with the first version of Apple. And basically, alienated a lot of people, made a lot of mistakes, was a miserable person to be around, and nobody liked working for him, and then he started his own company and sort of the same things happened with Next and then he got his second chance with Apple in the mid to late 90s. And he had learned many, many valuable lessons. He became an infinitely better manager on his second run in Apple. He was still abrasive. He would still be kind of a jerk. He still worked everyone to the bone. But he got much better at the social intelligence. If he remained who he was in that first act in Apple, he would have not succeeded. They would have fired him. He’d learned many lessons about how to be a better manager. OK. So, social intelligence is critical for getting beyond certain barriers in life. And even Albert Einstein who wasn’t, had probably Asperger’s and wasn’t the most socially gifted. He was a very charming person to be around. People liked being around Albert Einstein. So, I talk in the book. It’s a myth that these are workaholics that have no social skills. There are people out there that are like that but it’s a limiting factor. If that’s who you are, it’s going to be a constant barrier. The greatest masters, the da Vinci’s, the Benjamin Franklins, the Charles Darwins, the whomever, the Paul Graham. Well, Paul Graham is actually a different case there and we can get that in a minute. They all have developed excellent, excellent interpersonal skills.

I was surprised to read about Charles Darwin because he had become, in his later years, a kind of workaholic hermit living out in the country side in England, but as a young man, on a boat, sailing at 21 years old around the world to South American with 60 rough sailors and a rough captain, this guy learned incredible social skills, how to deal with this strange environment, how to deal with gauchos in Argentina and primitive, you know, indigenous cultures at the tip of Tierra del Fuego. This guy developed incredible political skills that helped him created a theory that was so revolutionary, it almost, you know, he was hated for it. So, this social intelligence is a critical aspect of it. And I mention Paul Graham. He’s an example of maybe someone who never thought he was good at it and he probably isn’t so good at it and his solution was. But he realized it as a weakness, he’s solution was to marry a woman, Jessica. Is that her name? Jessica Livingston?

Andrew: Yep. Who was incredible talented at this.

Robert: And she’s the social genius and she is his eyes. He uses her to judge other people because he doesn’t have that skill. So, he found a way to cover his weakness.

Andrew: And you know what even Paul Graham got better at it. Because I remember in the early days of Y Combinator because I’m always asking people questions about what are these interviewees like apart from the interviews. I remember talking to entrepreneurs who were deeply, deeply hurt by things that he said because they idolized this guy. They would read his writing like it was scripture. They obviously handed him a piece of their company because they wanted his mentorship. They idolized him and things that he would say would hurt him deeply. Today, I don’t think that exists any more. I think that there’s much more, there’s more of a sensitivity. I think that I talked to him about it in his interview. But let me say this. One of the problems that I have, Robert, with reading books that the guests write that I have on and I always read the books is that I always want to tell the stories, like tell. I almost want to interrupt you, but I usually don’t and I’ve been good here. But there’s one that I want to say about Benjamin Franklin, that, there was one story that you told where he was, I think, in England and he. What was it where he had to contribute to a drink fund? And maybe you’re much better telling it than I am but the reason I want you to tell that story is because it feels like when working with other people, we have to have a logic about their lack of logic. Everything else that we do at work has some logic to it but people aren’t. Can you tell that story?

Robert: Well, it’s in a context of Benjamin Franklin, a young man who goes out in the world, full of talent. A great writer already at the very early age. But he’s naive and he keeps making these social mistakes that get him into real trouble and he finds himself in England. And he starts working in printing offices because that’s where he apprenticed in Boston. And he’s working in one company in London. And all the workers there in the editorial department say you’ve got to contribute every week to a beer fund because they drink like three pints of beer everyday while they’re working because it’s England. And Benjamin Franklin doesn’t drink. He’s just a guy who likes to work hard. And so, he says, “No way. I’m not contributing to this beer fund. I’m not. First of all, I don’t drink so why should my money go to your thing? And second of all, you shouldn’t be drinking. You don’t work very well and you know. So I’m not contributing to your beer fund. Sorry.” And they all say, they nod their heads and this is typically how English people are. They say, “Oh yeah. Sure. That’s fine.” And then now he starts noticing that in these books that he’s editing, that’s part of his job, all of these mistakes start cropping up. Proofreading mistakes. Copyediting mistakes. They’re getting into the actual book that’s printed. He’s getting horrible feedback from his bosses. He’s going to be fired within a couple of weeks if he doesn’t figure out what’s going on here. Slowly, it dawns on him. That the other workers are sabotaging him. They didn’t want to say, they didn’t want to confront him personally and say, “You contribute to the beer fund or we’re going to mess with your life.” They indirectly sent the signal to him that you’re going to get yourself fired and we’re going to get you out of our office unless you start contributing to our beer fund.

Well, as an observant young man, he realized that that was what it was. It wasn’t some ghost there that was changing all of his documents. He started seeking tribute to the beer fund [??], and he had this realization that it’s not about him. You have to be realistic. When you enter a new work world, it’s like an alien culture. They have their rituals. They have their belief systems. They have their ways of doing things. You’re not there to change it. You’re only one person, and you’re generally a peon there when you first enter. You’re not there to change their culture. You’re going to learn it, you’re going to fit in, and eventually you’ll get the hell out and do what you need to do and not have to fit in. But, in the beginning it’s more important to understand human nature, understand people have their habits, and to not try to be abrasive and to change it. So, he learned through his negative experiences how to be, what I consider, the most socially astute person I’ve ever read about in history.

Andrew: And he started out being the opposite of that.

Robert: Yep.

Andrew: To his credit, he wasn’t indignant about it. He didn’t say, ‘I’m absolutely right. You guys are absolutely wrong. I’m not drinking this. You should also stop messing with my stuff.’

Robert: Yeah.

Andrew: Deal with the world as it is. And I see that over and over again in mastery. I’m trying to think of what else we can talk about here before the end of the interview. Here’s something. Can’t we-, can we say, ‘Look, I can’t get a mentor. I really can’t deal with other people. I want to master something quietly, on my own. I’ll go get the books that I need to. I’ll listen to the pod casts that I need to. All right, Robert Greene’s telling me it’s not just about listening, it’s about taking notes.’ That’s the Faraday story, one of my takeaways there. I’ll take good notes. It’s also about using what you learn. I’ll use it, but I need to just camp out in my basement, or my office, and get my work done without getting a mentor and dealing with people and doing all that other stuff. Is that possible? To work in a cave like that?

Robert: It is possible. I talk in the book about Thomas Edison as a master, and he had no mentor. Probably because of his circumstances. He comes from poverty and has to go to work early in his life as a telegraph operator. And he managed through creating an intense discipline system, and then he used books as a mentor. He actually read about Michael Faraday, who was his mentor in spirit. Faraday was dead by that time, but he considered him his sort of mentor in absentia.

So, there are ways to do it. But, why do you want to do it? Mentor is the one way where you can streamline the process. It can help you go a little bit faster. Their experience becomes your experience. They tell you-, give you great feedback in the present that you can’t get from anybody else. They help make it a faster process.

Social intelligence is going to make your path through life much more smooth. If you don’t have social intelligence, and you live in your cave and you develop a great piece of technology, you’re going to get some money and you’re going to get some attention. But, then comes the fact that you now have to work with the people who are financing you, and you’re so bad at it that you offend them. And now you don’t even know why you offended them, and you’re stepping on your own feet. So, without social intelligence, without mentor, you’re creating waves in your path that you now have to swim against. Why do you want to do that?

You know, the people at Google were great at the technical thing, and then they decided to launch their own social media website. And they failed at it terribly, because they weren’t good at that social gig. Well, it hurt them in the business sense. It’s going to hurt you in business if you don’t understand the social aspect and how to deal with people.

And the point I make in the book is, the sensitivity that you have for people, the empathic powers that we’re born with, the ability to read other people is something that you transfer to your work. That kind of sensitivity and empathy is actually a critical skill in figuring out something technical, or in designing a great computer program. You’re designing the ultimate business for people to buy. They’re human beings, you have to understand their psychology. That cave model is not going to work very well in the long run.

Andrew: That would have disappointed me years ago. But, what I realized today is, that other stuff is not as hard as I thought it would be, you know. Understanding people’s operating system is not as hard as understanding even a computer’s operating system. Once you get the logic of it, you understand everything else that people do.

Robert: Yeah, think of it that way. I have in the book Temple Grandin, who was born with autism, doesn’t have any social skills. And, she learns it. It’s like a mathematic-, math problem. She’s going to learn what offends people, what they like, and solve it and write it down, and learn almost like how to learn dance steps. That’s the approach. It’s all the same. It all works.

Andrew: What is that word called that you talk about in the book Mastery that, well. I notice that I love talking to people and doing interviews with a pen in my hand and writing things down. And to me it felt so illogical. I could type my notes right into the computer. I’m looking at my notes on the screen anyway. I might as well as you tell me something, put it in those notes and then I have it without having to scan it in but I think better with a pen in my hand and after reading Mastery, I discovered that other people do the same thing. Einstein held a ball in his hand and he’s squeezing it as he’s thinking. Others. Tons of examples. What is it called? I can’t think of the word and I can’t find it in my notes.

Robert: Well, it’s in the creativity section and I’m talking about how you want to use other things besides just words for your creativity process.

Andrew: Right.

Robert: Smells. Touch. Feel. Maybe you’re talking about synesthesia?

Andrew: That’s it. What is synesthesia?

Robert: Synesthesia is the fact that all of our sense can be interconnected in the brain. There isn’t a separate compartment for feeling, sensing, smelling, touch, vision. They’re all interconnected and in some people the wirings get a little more crossed than others. So, they smell a color. They hear a color. They hear a smell. And [??] goes into it and it’s fascinating and generally artists and high level scientists have more synesthesia than others. It indicates that their brain is having some weird connecting issues. They’re more connected than they should be but that also makes them more brilliant because other things are being connected besides just the senses.

Andrew: I see. Not just senses but different ideas are also connecting in a way that they wouldn’t for most people.

Robert: Yeah. So, you’re holding that pen in that hand, there’s some kind of mechanical, manual thing that’s calming you down. It’s serving a function. And those things are great and they’re brilliant. And we all have them. So, you know.

Andrew: What’s yours?

Robert: You know, I have this insane doodling thing that I’ll go through where I just doodle these really bizarre shapes and I have no idea what the hell they mean but it calms me down and if I’m listening to like my mother or something like that, I’m just sitting there doodling. I can doodle for hours.

Andrew: You don’t happen to have one of those up near you that you can put up on the screen, do you?

Robert: I probably do.

Andrew: Oh, I’d love to see that.

Robert: It makes me look rather in sane. You know? Like that kind of crap.

Andrew: All right. Can you put it closer? I want to. Oh, not insane. That makes sense.

Robert: It makes sense?

Andrew: I mean, I don’t know what it is, but it makes sense that you would sit and draw that out if it was really elaborate then I would feel that you weren’t paying attention to your mother but if it’s those small doodles, it makes sense that you would do that. Sometimes it focus us to do that. So, here’s where I’d like to end this. The final question is this. We go through all this hard work of cleaning people’s offices so that we can learn from them, being their apprentice, working hard like Bill Bradley, constantly struggling and learning from reading books, finding our passion and having the struggle along the way of being on the wrong track. At the end of it, what’s the benefit? Do you have an example of now that you’ve done it your life is better?

Robert: Yeah, well, I have to. You can of loaded the question with all of that. Because you’re emphasizing all of the potentially kind of dreary aspects and making it seem like it’s a workaholic type of thing. So, let’s get away from that because that’s the wrong framing of the question. If you go into something that you love which is chapter number one and I make it chapter number one because I say you’re not going to master anything if you don’t master this one thing of finding your life’s task. You love basketball. You love science and inventing something. A new form of engine, like Henry Ford. Now, when you go through that practice that just seems so tedious. Or Bill Bradley. Bill Bradley wasn’t finding it tedious. The sense after a month of dribbling like that and getting really good and not having to look at the basketball. Man, that’s a great feeling. What’s a better feeling? To, you know, get high and it makes you kind of happy for a couple of hours but then the next day you feel kind of miserable and you’re not doing anything with your life or a couple of days of unpleasant practice and then suddenly you have this killer skill that you can now work on and take it even to a higher level? Each time you’re overcoming a limitation, you have a sense of fulfillment and confidence that just gets better and better and better. I call it the cycle of accelerated returns. You practice something. You get better at it. It’s more fun. It’s more fun. You practice harder. You practice harder. It gets more fun. It goes around in a circle.

That’s what happens with people that master skills. It gets more fun. It gets more exciting. It’s not a drudge thing. Yeah, there is a workaholic aspect to it. You’re putting in 10,000 hours. There will be moments when it doesn’t feel so exciting. I know that with books. But at the end of the day, after you’ve written a book, after you’ve invented something that’s useful to mankind. After you’ve started a business. You have a sense of fulfillment. You can now look back and say, “I didn’t waste those years. I did something.” And it’s a great feeling and now it propels you onto your next project. You’re not bored. You’re feeling constantly challenged. You have a sense that you’re realizing your potential. You’re developing confidence. I don’t know. I think that’s a better scenario than someone who just lays around and watches movies and smokes pot and has fun, maybe a little bit in the beginning but come 30 or 35, they’re not having so much fun any more.

Andrew: That’s a great place to leave it. And let me actually say this now. Not to you, Robert, but directly to my audience. This interview is one of the best parts of my work at Mixergy. If you’re book lover like I am, Robert Greene’s books are the kinds of books that you just want to spend time with because there deep studies of the topic with stories of people that you’ve never heard of but are interesting. People that you had heard of but you always had a shallow understanding of. If you guys saw me during this interview, fuss around with my notes than usual, it’s because when I read one of Robert’s books whether it’s the Art of Seduction or the 48 Laws of Power, I just take constant notes and I struggle actually to keep it all organized here and to me as a guy who loves books, it is such a pleasure to interview Robert Greene as opposed to some of these authors that I have to turn away because I am a book lover, because I know what they’re doing is just building the next step in their career instead of writing a book because they have something to say.

Instead of writing a book because they have depth of understanding that they have to share with you. They often, I feel like they take two points and they stretch it out over what a 140 pages because that’s the bare minimum instead of feeling like they have to say, what do I leave out and still keep my message in there. How do I really blow people’s minds with depth, with stories they want to share that stick in their minds? That gives them a heightened understanding of the world around them? Robert, I’m sorry almost to say this with you here sitting in front of me, because this is almost embarrassing a thing that I have to say and gush like this but the audience has to hear everything. My insecurities and my passions and you’ve heard me say I’ve been insecure at times in interviews you have to also hear me talk about the passion for good books. If you’re a book lover, and you’re into this understanding of power, of greatness, of mastery and you haven’t read Robert Greene’s books, shame on you. Frankly, shame on you. I don’t get to share this. If Robert Greene offered me a percentage, if he said, if Ryan Holiday said I’m going to give you an affiliate program for selling his books or he’s got this course that, I would be so insulted. I got to tell you this only because I love it and because I love you, my audience. Find a way to get a copy of this. Go to your bookstore. Go to your library. Find a way. Come over here. Well, I’m not giving you my Kindle. But go get it. Seriously, as a book lover, from one book lover to another lover of education and understanding ideas. Guys, if you’re listening to this, please find any one of these books. He’s already on the best seller list for this book. So, he doesn’t need me to promote Mastery but I need you to do it. And I need to also say this again, Robert. Thank you for doing this. This is our second interview. Thank you for coming here and doing this interview with me.

Robert: Thank you. That was. This is the best thing I’ve ever heard. That was really wonderful, Andrew. Thank you.

Andrew: I appreciate having you on here. It’s good to meet you. Very nice.

Robert: Thank you. Bye. Bye.

Andrew: Thank you all for being a part of it. Bye.

Who should we feature on Mixergy? Let us know who you think would make a great interviewee.