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Naval Ravikant with Shane Parrish.

2026-08-24Podcasts

A deep conversation with Naval Ravikant and Shane Parrish covering reading, decision-making, learning, investing, and building a better life.

Naval Ravikant with Shane Parrish

(Edited and refined for clarity while fully preserving original meaning, wording, and conversational flow.) Shane Parrish: Hey, it’s Shane Parrish and welcome to a new episode of The Knowledge Project, where we deconstruct actionable strategies you can use to make better decisions, learn new things, and live a better life.

This time around we have the amazing Naval Ravikant. Naval is the CEO and co-founder of AngelList. He’s invested in more than 100 companies, including Uber, Twitter, Yammer, and many others. Don’t worry—we’re not going to talk about early-stage investing. Naval is an incredibly deep thinker who challenges the status quo on so many things. He’s thought deeply about subjects near and dear to us: reading habits, decision-making, and life.

A heads-up: this is the longest podcast I’ve ever done. Our conversation lasted over two hours, and if you’re like me, you’re going to take a lot of notes. A complete list of books and sites mentioned is available in the show notes at FarnamStreetBlog.com/podcast. A transcript is available for members of our Learning Tribe. If you want to join, head over to FarnamStreetBlog.com/tribe.

Without further ado, here’s Naval.


Shane: Welcome to the show. I’m so excited to talk to you today and ask you a whole bunch of questions that have been on my mind.

Naval: Thanks for having me. I’m excited to be here. I’ve been a longtime fan of your work.

Shane: Thank you. Let’s get started with something simple. Can you tell me a little bit about what you do?

Naval: It’s actually not that simple. I have a hard time saying what I do. My day job is that I am CEO of AngelList, the company I started almost seven years ago. AngelList is a platform for startups in the tech industry. We help entrepreneurs raise money, recruit talent, and find jobs in startups. We recently acquired Product Hunt, so we also help companies launch products to customers. It’s basically a one-stop shop for the early-stage tech ecosystem—whether you’re raising money, investing, recruiting, being recruited, or launching a product.

That’s my day job, but I’m also involved in a bunch of other things. I’ve angel-invested in about 200 companies, advised a number of others, sat on boards, occasionally blog, and tweet. I’m also a small partner in a cryptocurrency fund because I’m really into Bitcoin, Ethereum, and related coins. And I’m always cooking up side projects that I forget about and lose track of.

Shane: What does your typical day look like?

Naval: That’s the good part—I don’t have a typical day, and I don’t want one. If there is a typical day, I’m usually in my office at AngelList, operating mostly on email, phone, or meetings. Some days I work completely from home. Some days I don’t work at all. I’m actually trying to get rid of the concept of having to be in a specific place at a specific time. All I care about is whether I’m doing what I want to do, being productive, and being happy. I want to break away from the idea of 40-hour weeks, 60-hour weeks, nine-to-five, roles, jobs, or identities. It all feels like a straitjacket.


Reading Habits

Shane: You’re one of the best, most voracious readers I know. You’ve called yourself a conscious bookworm. How did you first get interested in reading?

Naval: Reading was my first love. When I was around 9, 10, or 11, I was a latchkey kid. My mom worked multiple jobs and went to school at night. My brother and I were raised by a single mother in a not-very-safe part of New York City. The library was my after-school center. After school I’d go straight there and hang out until they closed.

Even before that I loved books. At my grandparents’ house in India I’d sit on the floor going through all of my grandfather’s Reader’s Digests. I read comic books, mysteries, storybooks—whatever I could get my hands on. I was antisocial and introverted, and I just got lost in the world of words and ideas from an early age.

I was lucky that no one forced me on what to read. There’s a tendency among parents and teachers to say “you should read this, but don’t read that.” I read a lot of what by today’s standards would be considered mental junk food. Eventually you run out of the junk food and start eating the healthy food. Your taste gradually improves. I started with comic books, moved to mysteries, then fantasy, sci-fi, science, mathematics, and philosophy. It just kept climbing up the stack.

Shane: Is most of what you read physical or on a computer or Kindle?

Naval: For convenience it’s mostly Kindle—not the Kindle device, which sucks, but on an iPad. For books I really love I also buy a physical copy so there’s no excuse not to read it. A really good book costs $10 or $20 and can change your life. Even when I was broke I always spent money on books. I never viewed that as an expense—it’s an investment. I probably spend ten times as much on books as I actually get through. For every $200 worth of books I buy, I end up reading about $20 worth. It’s still absolutely worth it.

If I read a book and know it’s amazing, I’ll buy multiple copies—partly to give away, partly to have them around the house. These days I find myself rereading as much or more than I read new books. I saw a tweet from someone who said, “I don’t want to read everything. I just want to read the 100 great books over and over again.” There’s a lot to that. It’s about identifying the great books for you and really absorbing them.

I have poor attention. I speed-read, jump around, and couldn’t tell you specific passages or quotes. But at some deep level you absorb them and they become part of the threads of the tapestry of your psyche. There are books you pick up and get an increasing sense of déjà vu, then halfway through realize you’ve read it before. That’s perfectly fine—it means you were ready to reread it.

Shane: What books are you rereading now?

Naval: I’m always reading some science. I just reread Seven Brief Lessons on Physics. I’m rereading Sapiens again—I love that book. I’m pretty much always reading something by Jiddu Krishnamurti or Osho. I’m reading a book on René Girard’s mimetic theory. Tools of Titans by Tim Ferriss. Stories of Your Life and Others by Ted Chiang—one of my favorite sci-fi collections. A book on thermodynamics and complexity by a friend of mine that isn’t published yet. I finished Pre-Suasion by Robert Cialdini. I recently reread The Lessons of History by Will and Ariel Durant. I’m currently reading The Story of Philosophy, also by Will Durant. I have a young kid, so lots of child-related books I use more as reference material.

There’s Feynman’s Perfectly Reasonable Deviations, Genius by James Gleick about Feynman, Matt Ridley’s The Evolution of Everything, Dale Carnegie, The Three-Body Problem, Man’s Search for Meaning, and many more. Hundreds and hundreds of books downloaded.

Shane: You’ve said before you think of books as throwaways. How did you come to think about books like that?

Naval: That’s really an impact of the internet. Once the internet came along it destroyed everybody’s attention span. All of humanity’s works are available at any given time, and you’re interrupted constantly. Attention spans go down. At the same time we become more judicious—we want the meat.

The problem with books is that writing and publishing a physical book takes a lot of work, effort, and money. Sometimes people put long, wrapping books around simple ideas. Those are my least favorite. It’s why I avoid the whole business and self-help category—you generally have one good idea buried in hundreds of pages of anecdotes.

In the late ’90s I stopped reading as many books and started reading more blogs. Great blogs like Farnam Street, Kevin Simler’s Melting Asphalt, and others give you incredibly smart people justifying, simplifying, and writing great things in a page or two or three. I got really into blogs and stopped reading books. But a lot of the oldest wisdom is in books. With books you’re talking about the combined works of all of humanity, as opposed to just who happens to be blogging right now.

I realized I missed that. With the Kindle and iBooks I could start treating books the way I treat blogs: skim through lots of them until I find something interesting, consume that piece, and not feel guilty about finishing the entire book. A book is like a blog archive—you can read just the parts you need. That opened the world of books back up.

Many people are stuck on a book somewhere. If you ask people if they read, everybody says they do and can name the book they’re “reading.” The reality is very few people actually finish books. That’s because of all these societal and personal rules: you must finish a book, you must read books that are good for you, you can’t read junk-food books, this is the hot book right now. The reality is I don’t actually read that much compared to what people think. I read one to two hours a day, which puts me in the top 0.01%. That alone accounts for any material success I’ve had and any intelligence I might have. Real people read a minute a day or less. Making it an actual habit is the most important thing. How you make it a habit doesn’t matter.

It’s very much like exercise. The important thing is to do something every day—it almost doesn’t matter what. The best workout is the one you’re excited enough to do every day. The same way, the best books (or blogs or Twitter or anything with ideas) are the ones you’re excited about reading all the time.

Shane: Do you set aside time in your day to read, or do you fit it in when you have time?

Naval: I read when I’m bored of everything else. The good news is I get bored very easily, so there’s always a book to capture the imagination. Usually at night before bed, but it’s not a flawless thing. When I’m on vacation I’ll read. If I’m sitting in a Lyft or Uber I’ll read. Sometimes in the morning after I’ve worked out. Sometimes when I wake up I’ll just grab my phone and read. I’m not a very disciplined person, so I don’t set hard-and-fast rules. Because I love to read, whenever I’m bored and have time I just do it. The iPhone, Kindle, and iPad make it really easy.


Habits and Unconditioning Yourself

Shane: The people I know who read quite a bit and have a reading habit like you’ve described tend to be very habitual. Where did that come from?

Naval: I don’t think I’m more habitual than anybody else. Human beings are entirely creatures of habit. As young children we’re born with no habit loops—essentially blank slates. Then we habituate ourselves, learn patterns, get conditioned, and use that to get through everyday life. Habits are good. They allow you to background-process certain things so your frontal lobe stays available to solve brand-new problems.

But we also unconsciously pick up habits and keep them for decades, and we may not realize they’re bad for us. Our attitude in life, our mood, our happiness or depression levels—these are also habits. How often do we eat, what kinds of food, do we walk or sit, exercise, read—these are habits too. You absolutely need habits to function. You cannot solve every problem as if it’s the first time.

What we do is accumulate all these habits, put them in the bundle of identity and ego, and get attached to them: “I’m Shane, this is the way I am. I’m Naval, this is the way I am.” It’s really important to be able to uncondition yourself—to take your habits apart and say, “Okay, that’s a habit I probably picked up when I was a toddler trying to get my parents’ attention. I’ve reinforced it for decades and call it part of my identity. But is it serving me anymore? Is it making me happier, healthier, or helping me accomplish what I want?”

I would argue I’m less habitual than most people. I don’t like to structure my day. To the extent that I do have habits, I’m trying to make them more deliberate rather than accidents of history.

Shane: What’s a habit you’re trying to change right now?

Naval: I’ve done a lot of habit changes over the last few years. I now have a daily workout, which is a great habit. I cut down heavily on drinking—not fully eliminated, but mostly gone. I dropped caffeine. I’m not on the strict paleo diet, but a variation I call “paleo-ish.” I try to be paleo but fail constantly, and I don’t beat myself up over it because approximating it is better than where I was historically.

I tried to build a meditation habit but failed. I have, however, made a habit of being meditative. The one I’m currently trying to cultivate is doing yoga more regularly, but I haven’t formed a solid plan around that yet.

I reject a lot of the stuff peddled today about how you form or break habits. There’s a popular book (one I even recommended) that talks about the science behind habits and concludes you can’t break habits—you can only replace them. That’s BS. I’ve definitely broken habits completely. You can uncondition yourself. It’s just hard. It takes work and effort. Usually the big habit changes come when there are strong desire and motivators attached to them.

A big habit I’m working on—hard to explain in any way a normal human will understand—is trying to turn off my monkey mind. When we’re born as children we’re pretty blank slates, living very much in the moment, reacting to our environment through instincts, living in what I would call the real world. Then puberty comes along—the onset of desire. For the first time you really want something and start long-range planning for it. You start thinking a lot and building an identity and ego to go get what you want. This is normal and healthy—it’s part of being the human animal. But at some point it gets out of control.

We are constantly talking to ourselves in our heads, playing little movies, walking down the street with no one actually there. If you voiced every thought in your head you’d be locked up. But if you walk down a street with a thousand people, I think all thousand are talking to themselves at any given point—constantly judging everything they see, playing back movies of yesterday, living in fantasy worlds of tomorrow. They’re holed out of base reality.

That can be good for long-range planning and problem-solving—it’s good for the survival and replication machines that we are. But I think it’s actually very bad for your happiness. In my mind the mind should be a servant and a tool, not the master. It’s not something that should be controlling me and driving me 24/7.

I’ve taken on this idea that I want to break the habit of uncontrolled thinking. It’s hard because the moment you try not to think of a pink elephant, you’ve just put a pink elephant in your head. It’s an almost impossible problem. It’s something that has to be guided by feel rather than by actual thinking. I’m deliberately cultivating experiences, states of mind, locations, and activities that help me get out of my mind.

All of society does that to some extent. People chasing thrills, action sports, flow states, orgasm—a lot of these are basically trying to get out of their own head, away from that voice and the overdeveloped sense of self. At the very least I do not want my sense of self to continue to develop and become stronger as I get older. I want it to be weaker and more muted so I can live much more in everyday reality, accept nature and the world for what it is, and appreciate it.

Shane: Do you think there’s a difference between turning off the monkey mind and suppressing it?

Naval: Absolutely. Suppression doesn’t work, because when you try to suppress, that’s the mind suppressing the mind. That’s just you playing games with yourself. It’s a very hard problem.


Quitting Alcohol and Building the Workout Habit

Shane: You basically stopped drinking alcohol. How did you work on deprogramming yourself from the social settings and environments where alcohol is available all the time? What benefits have you seen?

Naval: The alcohol habit came from two things: availability—being in situations where alcohol is available, accepted, and something you’re supposed to do—and desire. You want to do it because you’re trying to accomplish something else.

When I unpacked that, I realized a couple of things. Availability came from being out at night in environments where alcohol is being served. If you want to avoid that, stay in. But staying in is not fun. So what do you do? I started a daily workout regimen in the mornings. If you’re working out in the mornings you can’t stay up too late at night. You can’t be drinking too much. You screw up a few times and your morning workout is terrible—you have a headache, you feel bad. When you’re working out every day you can checkpoint yourself very easily: “This exact thing I do every single morning is suddenly harder, so therefore I’m weakened from the alcohol last night.” The morning workout checkpoint really helped me understand the consequences.

The more interesting question is why am I doing it? It boiled down to surviving longer in social environments I wasn’t particularly happy in. I essentially had to stun my brain into submission. There are better ways to do that. One is only associating with people where you don’t have to drink to be around them. That narrowed my friend circle and the kinds of events I go to.

There was a substitution effect. Some of what I was drinking for was so that I wouldn’t be thinking so much. If I can cultivate states of not thinking too much another way, that takes away some of the urge. I switched from hard alcohol to red wine, which is inherently self-limiting—for me, two glasses and I usually have a headache. Some of it is also a function of age. I’m 42 now. I can barely make it through a single glass of wine without some negative consequence.

I still drink occasionally. I don’t believe in words like “never” and “always” because that limits you and makes you less free and less happy. I just want to be naturally in a position where I don’t need it and don’t desire it.

Shane: What habit would you say most positively impacts your life?

Naval: The daily morning workout has been a complete game-changer. It’s made me feel healthier and younger. It’s made me not go out late. It came from one simple thing: everybody says “I don’t have time.” Whenever you throw any so-called good habit at somebody, the most common excuse is “I don’t have time.” “I don’t have time” is just another way of saying “it’s not a priority.”

What you really have to ask is: is it a priority or not? If something is your number-one priority, you will get it done. That’s just the way life works. If you’ve got a fuzzy basket of ten or fifteen different priorities, you’re going to end up getting none of them.

What I did was say: my number-one priority in life—above my happiness, above my family, above my work—is my own health. It starts with my physical health, then my mental health, then my spiritual health, then my family’s well-being. After that I can go out and do whatever I need to do for the rest of the world. There’s a series of concentric circles starting out from me. Because my physical health became my number-one priority, I could never say “I don’t have time.” In the mornings I just work out, and however long it takes is how long it takes. I do not start my day until I’m done working out—I don’t care if the world is imploding.

Shane: Do you take any breaks from that, or is it every day?

Naval: It’s pretty much every day. There are a few days where I’ve had to take a break because I’m traveling or injured or sick, but I can count on one hand the number of breaks I take every year.


Happiness

Shane: You mentioned happiness being one of your top priorities. What is happiness to you? What does that word mean?

Naval: It’s a very evolving thing. Like all the great questions—“What happens when we die? Is there a Santa Claus? Is there a God? Who should I marry?”—there are no glib answers that apply to everybody. These questions ultimately do have answers, but they have personal answers. The answer that works for me is going to be nonsense to you, and vice versa.

Whatever happiness means to me, it means something different to you and to the listener. But I think it’s very important to explore what it is. For some people it’s a flow state. For some it’s satisfaction. For some it’s a feeling of contentment. My definition keeps evolving. The answer I would have given you a year ago would be different from what I tell you now.

Today I believe that happiness is a default state. It’s there when you remove the sense that something is missing in your life. We are highly judgmental survival and replication machines. We’re constantly walking around thinking “I need this, I need that,” trapped in the hedonic treadmill. Happiness is that state when nothing is missing. When nothing is missing, your mind shuts down and stops running into the future or the past to regret something or plan something. In that absence, for a moment, you have internal silence. When you have internal silence, you are content and happy.

People believe mistakenly that happiness is about positive thoughts and positive actions. The more I’ve read, learned, and experienced (and verified for myself), every positive thought essentially holds within it a negative thought. It’s a contrast to something negative. The Tao Te Ching says it more articulately than I ever could—it’s all duality and polarities. If I say “I’m happy,” that means I was sad at some point. If I say “he’s attractive,” that means somebody else is unattractive. Every positive thought has a seed of a negative thought within it, and vice versa. That’s why a lot of greatness in life comes out of suffering. You have to view the negative before you can aspire to and then appreciate the positive.

All that said, to me happiness is not about positive thoughts. It’s about the absence of desire—especially the absence of desire for external things. The fewer desires I can have, the more I can accept the current state of things, the less my mind is moving (because the mind really exists in motion toward the future or the past), the more present I am, the happier and more content I will be.

But if I latch onto that—“Oh, I’m happy now and I want to stay happy”—then I’m going to drop out of that happiness, because now the mind is moving, trying to attach to something, trying to create a permanent situation out of a temporary one.

Happiness to me is mainly not suffering, not desiring, not thinking too much about the future or the past, really embracing the present moment and the reality of what is, the way it is. Nature has no concept of happiness or unhappiness. To a tree there is no right or wrong, no good or bad. Nature follows unbroken mathematical laws and a chain of cause and effect from the Big Bang to now. Everything is perfect exactly the way it is. It’s only in our particular minds that we’re happy or unhappy, that things are perfect or imperfect, because of what we desire.

I’ve also come to believe in the complete and utter insignificance of the self. That helps a lot. If you thought you were the most important thing in the universe, then you have to bend the entire universe to your will. If it doesn’t conform to your desires, something’s wrong. But if you view yourself as a single-celled amoeba, or if you view all of your works as writing on water or building castles in the sand, then you have no expectation for how life should actually be. Life is just the way it is. You accept that. You have no cause to be happy or unhappy—those things almost don’t apply. What you’re left with in that neutral state is not neutrality. People think that would be a very bland existence. No—this is the existence little children live. If you look at little children, on balance they’re generally pretty happy because they’re really immersed in the environment and the moment without any thought of how it should be given their personal preferences and desires. I think the neutral state is actually a perfect state, and one can be very happy as long as one isn’t too caught up in their own head.

Shane: What does your internal monologue go like when you find yourself trying to attach to something?

Naval: By default I try to keep an eye on my internal monologue. It doesn’t always work, but in the computer-programming sense I try to run my brain in debugging mode as much as possible. When I’m talking to someone or engaged in a group activity it’s almost impossible because your brain has too many things to handle. But if I’m by myself—like this morning while brushing my teeth—I started thinking forward to the podcast and going into this little fantasy where I imagined you asking me a bunch of questions and I was fantasy-answering them. Then I caught myself. I put my brain in debug mode and just watched every little instruction go by. I said, “Why am I fantasy future-planning? Why can’t I just stand here and brush my teeth?” It was just the awareness that my brain was running off into the future and planning some fantasy scenario out of ego. At that point I shut it down, went back to brushing my teeth, and noticed how great the toothbrush was and how good it felt. Then the next moment I’m off thinking something else, and I look at my brain again and say, “Do I really need to solve this problem right now?” The reality is that 95% of what my brain runs off and tries to do, I don’t need to tackle at that exact moment. If the mind is like a muscle, I’ll be better off resting it, being at peace, and then when the particular problem arises, immersing myself in it.

What I would rather dedicate myself to is, for example right now as we’re talking, being completely lost in the conversation and 100% focused on this, as opposed to thinking about whether I brushed my teeth the right way or planning something else. The ability to singularly focus is related to the ability to lose yourself and be present, happy, and actually ironically more effective.

A lot of the things Buddha talked about—awareness versus the ego—what they’re really talking about is that you can think of your brain and consciousness as a multi-layered mechanism. There’s a core base kernel-level OS that’s running, and then there are applications running on top. I like to think of it as going back to my awareness-level OS, which is always calm, peaceful, generally happy and content. I’m trying to stay in that mode and not activate the monkey mind, which is always worried, frightened, and anxious but serves an incredible purpose. I’m trying not to activate that program until I need it. When I need it I want to just focus on that program. But if I’m running it 24/7 I’m wasting energy, it becomes me, and I am more than that.

Spirituality or religion or Buddhism will teach you over time that you are more than just your mind, more than just your habits, more than just your preferences. You’re a level of awareness. You’re a body. Modern humans don’t live enough in our body. We don’t live enough in our awareness. We live too much in this internal monologue in our heads—all of which, by the way, is just programmed into you by society and by the environment from when you were younger. You’re basically a bunch of hardware (DNA) that then reacted to environmental effects when you were younger. You recorded the things that were good and bad and use that to prejudge everything that’s going to be thrown at you, constantly trying to predict and change the future. As you get older the sum of these preferences and habitual reactions becomes very large, and they end up as runaway freight trains that control your mood.

Why don’t we study how to control our moods? What a masterful thing that would be if you could say, “Right now I would like to be in a curious state,” and then genuinely set yourself into the curious state. Or “I want to be in a mourning state—I’m mourning a loved one and I want to grieve for them, but I really want to grieve. I don’t want to be distracted right now by some mad computer-programming problem.”

I think the mind itself is a muscle and it can be trained and conditioned. It has just been haphazardly conditioned by society out of our control. If you look at it with awareness and intent—it’s a 24/7 job, you’re working at it every moment of every day—you can unpack your own mind, emotions, thoughts, and reactions and start reconfiguring and rewriting this program to what you want.


Foundational Values

Shane: You mentioned before in one of your interviews that you have foundational values, but you didn’t elaborate. What are those?

Naval: I’ve never actually listed them or fully articulated them. To define values first of all as a set of things you will not compromise on. Foundational values to me are things that I’ve looked at very carefully about myself, deliberately chosen, and said, “This is a habit, this is a way of life, and I’m not going to compromise on that. I’m going to stay this way forever. I just don’t want to live life any other way.”

I’ve never fully enumerated them, but examples:

  • Honesty. I want to be able to just be me. I never want to be in an environment or around people where I have to watch what I say. If I disconnect what I’m thinking from what I’m saying, that creates multiple threads in my mind. I’m no longer in the moment. I now have to do future planning or past regretting every time I’m talking to somebody. Anyone around whom I can’t be fully honest, I don’t want to be around.

  • No short-term thinking or dealing. If I see anybody who’s even around me thinking in a short-term manner with somebody else, I don’t want to do business with that person anymore. All the benefits in life come from compound interest—whether in money, relationships, love, health, activities, or habits. I only want to be around people that I know I’m going to be around for the rest of my life, and I only want to work on things that I know have good long-term payout.

  • Pure relationships / peer relationships. I don’t believe in hierarchical relationships. I don’t want to be above anybody or below anybody. If I can’t treat someone like a peer and they can’t treat me like a peer, then I just don’t want to interact with that human.

  • No anger. That was something that was good when I was young and full of testosterone. Now, like the Buddhist saying, anger is a hot coal that you hold in your hand while waiting to throw it at somebody. I don’t want to be angry and I don’t want to be around angry people. I just cut them out of my life. I’m not judging them—I went through a lot of anger too—they have to work through it on their own. Go be angry at someone else.

I don’t know if that neatly falls into the classical definition of value, but it’s a set of things that I won’t compromise on and that I just live my entire life by. Everybody has values. A lot of finding great relationships, great co-workers, great lovers, wives, husbands is finding other people where your values just line up. Then the little things don’t matter. Generally I find that if people are fighting or quarreling about something, it’s because their values don’t line up. If their values lined up, the little things wouldn’t matter.

Shane: How radical is your honesty, and how has that impacted your life?

Naval: It’s pretty honest. I’m not like Ray Dalio from Bridgewater, who is theoretically extremely honest. I’m not going to go call somebody ugly to their face. I’m not trying to make a big show of it or shock people. Radical honesty just means that I want to be free. Part of being free means that I can say what I think and think what I say—they’re highly congruent and integrated.

It also means, as Richard Feynman famously said, you should never ever fool anybody, and you are the easiest person to fool. The moment you tell somebody else something that’s not honest, you’ve lied to yourself. Then you’ll start believing your own lie, and that will disconnect you from reality and take you down the wrong road. It’s really important for me to be honest. But I don’t go out of my way volunteering negative or nasty things.

I combine radical honesty with an old rule that Warren Buffett has: praise specifically, criticize generally. If you have a criticism of someone, don’t criticize the person—criticize the general approach or that class of activities. If you have to praise somebody, always try to find the person who is the best example of what you’re praising and praise that person specifically. That way people’s egos and identities, which we all have, don’t work against you—they work for you.

Shane: Have your values changed at all since becoming married and becoming a parent?

Naval: Values almost by definition don’t change that much over time, but it takes some time for you to figure out your own foundational values. Everybody has them—it’s just that maybe we’re not that aware of them until later. Mine have changed a little bit but not a lot.

My wife is an incredibly loving, family-oriented person, and that was one of the foundational values that brought us together. The moment you have a child is this really weird thing—it answers the built-in “meaning of life / purpose of life” question. All of a sudden the most important thing in the universe moves from being in your body into the child’s body. That changes you, and your values inherently become a lot less selfish.

Probably the biggest change was that when I was younger I really, really valued freedom. Freedom was one of my core values. Ironically it still is—it’s probably one of my top three—but it’s a different definition of freedom. My old definition was freedom to: freedom to do anything I want, freedom to do whatever I feel like whenever I feel like. Now the freedom I’m looking for is internal freedom: freedom from reaction, freedom from feeling angry, freedom from being sad, freedom from being forced to do things. I’m looking for freedom from, internally and externally, whereas before I was looking for freedom to.


Biggest Mistakes

Shane: What’s the biggest mistake you’ve ever made in your life, and how did you recover?

Naval: I’ve made a class of mistakes that I would summarize the same way. It was obvious to me looking at the mistakes only in hindsight, through one exercise: when you’re thirty, what advice would you give your twenty-year-old self? When you’re forty, what advice would you give your twenty- or thirty-year-old self?

If you do that exercise decade by decade (or every five years if you’re younger), and really sit down and say “Okay, 2007 what was I doing, how was I feeling? 2008… 2009…” at least for me a remarkable consistency emerged. Everything that I was doing, I should have still done—but with less emotion, and especially less anger. I used to be very angry when I was younger.

Life is going to play out the way it’s going to play out—some good, some bad—but most of it is actually just up to your interpretation. You’re born, you have a set of sensory experiences, then you die. How you choose to interpret those sensory inputs is up to you. Different people interpret them in different ways. I wish I had done all of these things but with less emotion and less anger.

The most celebrated example: when I was younger I started a company. The company did well, but I didn’t do as well. I sued some of the people involved. It was a good outcome for me in the end and everything worked out okay, but there was a lot of angst and a lot of anger. Today what I would do is not go down the angst and the anger. I would have just walked up to the people and said, “Look, this is what happened. This is what I’m going to do. This is what’s fair. This is what’s not.” I would have realized that the anger and the emotion themselves have this huge cost and are just completely unnecessary.

Now I’m just trying to learn from that and do the same things that I think are the right things to do, but without anger and with a very long-term point of view. If you take a very long-term point of view and take the emotion out of it, I wouldn’t consider those things mistakes anymore.

Other than that, the perspective I like to adopt is that everything that I did and everything that was done to me—and there’s some impossible-to-separate combination—brought me to this exact moment here today talking to you. And this is a good moment. Whatever set of circumstances conspired to bring us here, we’re good, because here I am.

Shane: Was there a moment when you realized that you could control how you interpret things? A lot of people don’t recognize that they can control not what happens to them per se, but how they respond and how they interpret a situation.

Naval: I think everyone knows it’s possible. The reason we know it’s possible is there’s a great Osho lecture called “The Attraction of Drugs and Spirituality.” What do people do drugs for—everything from alcohol to psychedelics to cannabis? They’re doing it to control their mental state and how they react. Sometimes it’s worse, sometimes it’s better. Some people drink because then they don’t care as much. Some are potheads because they can zone out. Some do psychedelics so they can feel very present or connected to nature. The attraction of drugs is spiritual. To some extent we already know that we can control our internal state—we just use external bioactive substances to do it.

Now there are a lot more techniques out there in the public domain, many dug up from older times: cognitive therapy, behavioral psychology, meditation, taking long walks in nature. You can control your mental state. We’re just used to doing it by hacking our external circumstances to then come back around and control our mental state.

There’s a famous line that says all of man’s problems arise because he can’t sit by himself in a room for 30 minutes. (I’ll plaster “or woman” onto that.) If a man or a woman can sit by themselves on a cushion for thirty minutes—that’s hard; it’s really hard to do—that’s meditation. You are essentially struggling with and controlling your internal state. The first thing to realize is that you can actually observe your mental state. The advantage of meditation is not that you’re going to gain a superpower to control your internal state. It’s that you will recognize just how out of control your mind is. It is like a monkey flinging feces, running around the room making trouble, shouting, breaking things. It’s completely uncontrollable—an out-of-control mad person. You have to see this mad creature in operation before you feel a certain distaste toward it and start separating yourself from it. In that separation is liberation. When you realize “Oh, I don’t want to be that person. Why am I so out of control?”—just that awareness alone calms you down.

There are many techniques. Another example a lot of smart people use: if you’re angry about something or if you get an unhappy email and you want to respond, don’t respond for 24 hours. What does that do? You calm down. The emotions subside. The hormones go down. You’re in a better mental state 24 hours later.

People already know this, but we just don’t act on it because socially we’re not conditioned to act on it. Socially we’re told: go work out, go look good—because that’s a multiplayer competitive game. Other people can see if I’m doing a good job or not. Or we’re told: go make money, go buy a big house—again, external multiplayer competitive game. But when it comes to learning to be happy, training yourself to be happy—completely internal, no external progress, no external validation, 100% competing against yourself, single-player game—we’re such social creatures (more like bees or ants that are externally programmed and driven) that we just don’t know how to play and win at these single-player games anymore. We compete purely on multiplayer games. But the reality is life is a single-player game. You’re born alone. You’re going to die alone. All your interpretations are alone. All your memories are alone. And you’re gone three generations from now—nobody cares. Before you showed up nobody cared. It’s all single-player.

Buffett has a great example of that: would you rather be the world’s best lover and known as the worst, or the world’s worst lover and known as the best? In reference to an inner or external scorecard. Exactly right. All of your scorecards are internal.

Jealousy was a very hard emotion for me to overcome when I was young. I had a lot of jealousy. I learned to get rid of it (it still crops up every now and then). It’s such a poisonous emotion because at the end of the day you’re no better off—you’re unhappy—and the person you’re jealous of is still successful or good-looking or whatever they are. The real breakthrough for me was when I realized at a personal, fundamental level that all these people I was jealous of—I couldn’t just cherry-pick and choose little aspects of their life. I couldn’t say “I want his body, I want her money, I want his personality.” You have to be that person. Do you want to actually be that person with all of their reactions, their desires, their family, their happiness level, their outlook on life, their self-image? If you’re not willing to do a wholesale 24/7 100% swap with who that person is, then there’s no point in being jealous. Once I came to that realization, jealousy just sort of faded away. I don’t want to be anybody else. I’m perfectly happy being me. And even that is under control—to be happy being me. There’s no social reward for it, but there’s a lot of internal reward. It’s almost anti-social rewards, because when you’re working on your inner stuff people don’t love that. Your friends of course support you, but they’re not getting anything out of it.

Even when I look at my own peer group, to the extent that they’re working on themselves, everyone in their forties at some level is mostly engaged in group activities: “Hey, let’s do a group meditation. Hey, let’s do this group lecture.” I keep coming back to this one line I read: only the individual transcends. Nobody reaches enlightenment or internal happiness or does serious internal work in group settings. It is a very lonely kind of task. To some extent I think that people who are constantly looking for social affirmation in their internal work aren’t that serious about it. They’re craving more social interaction than they’re really craving internal work.


Changing Your Mind

Shane: What big ideas have you changed your mind on in the last few years?

Naval: There’s a lot. On a life’s level there are a couple. On a more practical basis I just stopped believing in macroeconomics. I studied economics and computer science in school, and there was a time when I thought I was going to go be a PhD in economics. The further I get, the more I realize that microeconomics, the combination of complex systems and politics… you can find a macroeconomist to take every side of every argument. That discipline, because it doesn’t make falsifiable predictions (which is the hallmark of science), has become corrupted. You never have the counter-example on the economy. You can never take the US economy and run two different experiments at the same time. Because there’s so much data, people kind of cherry-pick whatever political narrative they’re trying to push. To the extent that people spend all their time watching the macro economy or the Fed forecasts or which way the stocks are going to go next year—that’s all junk. It’s no better than astrology. In fact it’s probably even worse—less entertaining and more stress-inducing. I just think of macroeconomics now as junk science. All apologies to the macroeconomists.

That said, microeconomics and game theory are fundamental. I don’t think you can be successful in business or even navigating through most of our modern capitalist society without an extremely good understanding of supply and demand, labor versus capital, game theory, tit-for-tat, and those kinds of things. So macroeconomics is a religion that I gave up.

There are many others. I’ve changed my mind on death, on the nature of life, on the purpose of life, on marriage. I was originally someone who did not want to be married and have kids. There have been a lot of fundamental changes. But the most practical one is I gave up macro and embraced micro. And I would say that’s true not just in macroeconomics—that’s true in everything. I don’t believe in macro environmentalism; I believe in micro environmentalism. I don’t believe in macro charity; I believe in micro charity. I don’t believe in macro “improving the world.” There are a lot of people out there who get really fired up about “I’m going to change the world. I’m going to change this. I’m going to change the way people think.” I think about micro: change yourself, then maybe change your family and your neighbor, before you get into abstract concepts about changing the world.

Shane: Of your base knowledge that you have today that you believe, what do you consider the least solid or most likely to change over the coming years?

Naval: Good question. I try not to have too much that I’ve pre-decided upon. Creating identities and labels locks you in and keeps you from seeing the truth. I used to identify as libertarian, but then I found myself defending positions that I hadn’t really thought through just because they were part of libertarian canon. The reality is that if all of your beliefs line up into ten neat little bundles, you should be highly suspicious, because they’re pre-packaged and put together. I don’t like to self-identify at almost any level. That keeps me from having too many of these so-called stable beliefs. So it’s hard for me to point to something that I think is shaky, because if I thought it was really shaky then I wouldn’t stand on it.

I guess the areas where I’m becoming least certain are all the “grand category of how should we organize society” beliefs. Everybody has them. Some people think we should be communists, some are capitalists, some are anarchists, some say we need a larger welfare state, universal healthcare, and basic income; others say no, we need none of that. I think the entire class of beliefs is unfalsifiable. They’re almost religious. They’re things that people got into when they were young. Nobody actually knows which system is the better one. Nobody actually knows which one maximizes happiness versus output. I know there’s a lot of smart economists and people studying it, a lot of good data and science, but at the end of the day the more I look into it the more I come away saying “Maybe I don’t know how best to organize society. Maybe society should not have just one organization but should have multiple organizations so you can choose which society you are most bound to thrive in.” I don’t think there is a single right answer for human culture and society anymore—except to the extent that, given the increasingly destructive power of technology (along a long enough timescale you can 3D-print a nuclear weapon; along a long enough timescale you can create a singularity in your backyard as part of your high-school physics project), as a human race we do have to sort of get past this idea that we’re separate organisms and almost get to some kind of multicellular-organism situation. Otherwise we’ll just destroy ourselves—it’ll just be too easy to blow ourselves up. That obviously runs very, very counter to my libertarian instincts of everyone should be free to do whatever they want. So I just don’t know how to organize society anymore. Any remnant beliefs I have from being younger about the optimal way to organize society are probably wrong. The future thriving society that we end up with maybe a thousand years from now will probably look like something that I would argue very strongly against today, because it will have no room for the individual.

Shane: Can you explain for listeners the singularity and what your thoughts are around that?

Naval: The singularity is this idea that technological change is accelerating, and at some point the acceleration gets so great that there’s massive change in our lifetimes. We create things like general AI, we start living forever, and the nature of who we are as humans changes. The consequence of that is most associated with general AI: we produce a general-purpose artificial intelligence that could then hack its own code, make itself smarter, and leave all of us at the point where we are either obsolete or immortal or something in between.

My thoughts: I think it’s fanciful, to say the least. Nick Bostrom wrote a very famous book called Superintelligence which lays out the case. There are good rebuttals to Superintelligence, so I wouldn’t just read that book breathless and wide-eyed and believe everything. There are people at the Singularity Institute who are looking forward to this coming. But I think it is religion for nerds. It’s got all the same characteristics: it’s unfalsifiable until it happens; it basically says the chosen will be saved; the world’s going to end; we will be immortal. It’s very hard to part from a biblical kind of story.

I find the people who are pushing it the most are what I would call armchair technologists. They might understand a little bit of science, but these are not the PhDs in physics who are pushing this. It’s not the Fields Medal-winning mathematicians. I was trained a little bit in science and I consider myself an amateur scientist, and I know just enough to know how little we know. Physics still can’t solve the three-body problem—collide three billiard balls together and you can’t tell what happens. We cannot properly model complex systems. We can’t tell the weather next week. We still can’t solve the vast majority of chronic diseases. We’re just starting to connect the gut and the brain and the bacteria in our system together. There is so much complexity in nature, and humans have just begun to scratch the surface, that to believe that we are going to sort of go into this world of perfection through technology I think is far-fetched.

Look, there’s AI. Everyone’s talking about AI. None of these people have written real code. We are no closer to creating a general AI than we were twenty years ago. Now there are actual huge advances that were made in specific AI, but these are data-processing problems. Basically if I dump huge amounts of real-world images into a neural network then I can do better image recognition—no question that is real; that is a data-driven solution. The algorithms haven’t gotten any better, and the structure of how the human brain works and how the human body works is still so far advanced beyond our machine capabilities that certainly if there’s going to be a singularity it’s not going to happen in my lifetime.

In that sense some things like the singularity are pernicious—for the same reason that the afterlife is pernicious. It takes you out of the moment. It gives you hope for the future so you stop living for today and start living for tomorrow. I know that doesn’t sound like much, but it’s actually a big deal. At any given time when you’re walking down the street, a very small percentage of your brain is focused on the present. The rest is future planning or regretting the past. That’s keeping you from an incredible experience. It’s keeping you from seeing the beauty in everything and from being grateful for where you are. I think it can literally destroy your happiness if you spend all your time living in delusions of the future.

I do think the singularity thing is good in the sense that it pushes forward technological advancement. We put more resources on it, we spend more time developing some of the great technologies that the human race is going to take advantage of. So in that sense, as an agent that pushes science forward, it’s a good thing. But I think it’s delusional to think that you’re somehow going to be saved before you die by some combination of AI and magic science. You just have to live the life you have.

There’s nothing but this moment. One has never gone back in time, and no one has ever been able to predict the future successfully in any way that matters. Literally the only thing that exists is this exact point where you are in space at that exact time that you happen to be. And like all the great profound truths, it’s all paradoxes. Any two points are infinitely different. Any moment is perfectly unique. But that moment itself slips by so quickly that you can’t grab it.


Education System

Shane: What’s your opinion on the current education system? When I asked people on Twitter what they wanted to ask you, this question came up a couple of times. How would you fix it?

Naval: There’s no question it’s completely obsolete. The education system is a path-dependent outcome from the need for daycare, from the need for prisons for college-aged males who would otherwise overrun society and cause a lot of havoc. The original medieval universities had guard towers that faced inwards, for example, because you had to put a curfew in there and lock up the young 18-year-old males before they went out with swords and daggers and created trouble. Colleges and schools as we think about them come from a time period when books were rare, knowledge was rare, babysitting was rare, crime was common, violence was prevalent, and there was no such thing as self-guided learning.

Now we have the internet, which is the greatest leveling of knowledge ever created, completely interconnected. It’s very, very easy to learn if you actually have the desire to learn. Everything is on the internet. You can go on Khan Academy, get MIT and Yale lectures online, get all the coursework, get interactivity. You can read blogs by brilliant people. You can read all these great books. The ability to learn, the means of learning, the tools of learning are abundant and infinite. It’s the desire to learn that’s incredibly scarce.

I just don’t think that schools matter for self-motivated students. What schools matter for is wanting to keep the kids out of the parents’ hair while the parents go to work. It creates socialization because kids want to be around their peers and they want to learn how to operate in society with their peers. But if it’s purely learning you’re after, that learning can be done much more either on your own or through the internet or by uniting through the internet with like-minded groups.

The second problem is what do you choose to learn. The current educational system has to have a one-size-fits-all model. It has to say “you have to learn X now and then you have to learn Y.” Examples of why this is obsolete: memorization. In a day and age of Google and smartphones, memorization is absolutely pointless. Why should you be memorizing the Battle of Trafalgar? Why should you be memorizing what the capital of this or that state is? But we still put undue weight on that just because that’s the way it’s always been done, from a pre-Google world.

Another example: when we’re moving along at a certain pace in mathematics. I’m sure 90% of your listeners have had this happen: they were learning mathematics and at some point they were keeping up—arithmetic, geometry, trigonometry, precalculus, calculus—and somewhere in there they got lost. Somewhere while building the massive edifice of logical structure that mathematics is, they missed one lesson, one concept. Or their brain just couldn’t think a certain way that something was being explained (it should have been explained visually but it was numerical, or symbolically but it was cartographic). The moment you lose that rung in the ladder, you can’t go to the next one. The teacher says “Okay, we’re done with precalculus and now we’re moving on to calculus,” and you’re saying “Wait, I didn’t understand precalculus and I don’t understand how precalculus leads from trigonometry to calculus.” Now you’ve reduced it to memorization: “Okay, when I see that dx/dy symbol I do this.” But you’ve lost the actual learning. You’ve lost the connection to the underlying principles.

I think learning should be about learning the basics in all the fields and learning them really well, over and over, because life is mostly about applying the basics and only doing the advanced stuff in things that you truly love and where you understand the basics inside and out. That’s not how our system is built. We teach all these kids calculus and they walk out not understanding calculus at all, when really they would have been better off just doing arithmetic and basic computer programming the entire time.

There’s a pace-of-learning issue, and then there’s finally a “what to learn” issue. There’s a whole set of things we don’t even bother trying to teach: nutrition, cooking, how to be in happy positive relationships, how to keep your body healthy and fit (we just say “sports”), happiness, meditation. Maybe we shouldn’t teach some of these things—different kids will have different aptitudes—but maybe we should. Maybe we should teach practical construction of technology. Maybe everyone in their science project, instead of building a little chemistry volcano, should be building a smartphone. We just haven’t kept up.

I have to believe that we can change the system, but you never change a system by taking the existing thing and reworking it. I don’t believe that. I’ve been in tech and business enough to know that you’re better off changing it just by creating something brand new.

One fantasy idea I’ve had: after I’m done with AngelList, or if I have more time on my hands, I would like to create a successor to the One Laptop per Child project that Nicholas Negroponte at MIT had. I saw this fascinating write-up a long time ago—maybe five years ago—in The Economist or somewhere. It was a story about how they left a box full of unopened Android tablets in a little village in Pakistan. When they came back months later the kids had opened the box, figured out and booted the tablets, hacked them, gotten past the user-administration login, installed a whole bunch of apps, set up a little economy. The older kids were teaching the younger kids. They were teaching their grandmothers how to run businesses. They were surfing the web. They’d taught themselves English. Kids are learning machines—they just need the tools.

To that end, what I would love to do is create a very low-cost, very rugged, easily powered, cheap Android tablet that’s hard to destroy, and basically distribute them around the world with pre-built learning applications so that you can literally fire one up and it works with you interactively in 30 seconds. It figures out what language you speak (if any), what level of aptitude you’re at (second grade or third grade or fifth grade—and of course that varies by different discipline), and then lets you dive in and learn anything you want that will make your life better. It always keeps you on the edge and always keeps pushing you. Then you can network in all the teachers of the world—anyone who wants to be a teacher can contribute—not just Salman Khan building Khan Academy, but essentially network-connect all the teachers of the world and all the students of the world using tablets, and do it at a pace and level where it’s essentially customized for each child, and they’re learning the things that have a practical outcome in their life.

I know there’s advantage to a liberal-arts education pushing things that people aren’t going to seek out to learn on their own, but they have to have some desire for it. It’s better to wait until they think they’re ready and then give it all, because I think that’s the way that learning sticks. That’s the kind of project I’d like to work on. But I don’t think it’s solvable with the current school system.

Shane: How do you, as an adult, go about learning new subjects—specifically physics, since you mentioned a couple of physics books?

Naval: Mostly I just stay on the basics. Even when I’m learning physics or science I’m sticking to the basics. I’ll read concepts for fun, but I’m more likely to do something that is arithmetic than calculus. I’m not going to be a great physicist at this point—maybe in the next lifetime, or when my kid will be. It’s too late for me. So I have to stick to what I enjoy.

What I love about science is that mathematics is the language of nature. Science to me is the study of truth. It is the only true discipline because it makes falsifiable predictions. Applied science becomes technology, and technology is what separates us from the animals and allows us to have things like cell phones, houses, cars, and electricity. Science to me is the study of truth, and mathematics is the language of science and nature. In that sense I’m not religious but I’m spiritual, and to me that is the most devotional thing that I could do: to study the laws of the universe. The same kick that some guy might get out of being in Mecca or Medina and bowing to the Prophet, I get that same feeling of awe and that same small sense of self when I study science. For me it’s unparalleled. I’d rather stay at the basics.

One thing I don’t like to do: when I do my books on the Kindle I skip two-thirds of them. The reason I skip two-thirds is because they’re kind of embarrassing—they won’t sound like good books; they’ll sound like trivial or silly or whatever. But who cares? I don’t have to tell everybody everything I read. I read all kinds of stuff that other people consider junk or even reprehensible. I read all kinds of stuff that I disagree with because it’s a mind-bender.

I found myself in some random dark hole on Twitter the other day where I was reading this guy’s tweets and thinking “Wow, he’s really smart, this is really interesting, he’s very clever.” Then it turned out this guy is a full-blown white supremacist—not even mildly; he just thinks everyone in the white race should be guarding and people like me shouldn’t be allowed on the streets. But it was still fascinating and he’s still really smart. I kept reading it. After a while I built up my own sense of his coherent view of the world and where he was coming from. But to do that I couldn’t have judged too much. And I’m certainly not going to go around bragging to my friends “Hey, I learned this from a white supremacist the other day.” To some level you almost have to read the stuff you’re reading because you’re into it and that’s it. You don’t need any other reason. There’s no mission here to accomplish. Just really because you enjoy it.

If you read what everybody else is reading, you’re going to think what everybody else is thinking. You need the diversity—almost like an index-fund approach where you’re going to catch the winners, but you can’t really identify a lot of them beforehand that are going to change you as a person, because so much of it is contextual.

Almost everything that people read these days is designed for social approval. All the bestsellers are about social improvement, social conditioning: if you really want to be successful, happy, blah blah blah—all those external metrics. You’re looking for a non-average outcome, so you can’t be reading the average thing. And all these things are actually old as the hills. You can go read Adam Smith’s The Wealth of Nations. You can go read Benjamin Franklin and his aphorisms to understand how to live your life. You could read Charlie Munger. You could read Charles Darwin to understand evolution from the source. You could read Watson and Crick to understand the structure of the double helix and DNA. But instead what we choose to read are just whatever is number one at the airport bestseller list or whatever our friends are reading. I know people who have read a hundred regurgitated books on evolution and never read Darwin. Or the number of macroeconomists out there who have read tons of treatises in economics and haven’t read any Adam Smith. At some level you’re doing it for social approval. You’re doing it to fit in with the other monkeys, to get along with the herd. But that’s not where the returns are in life. The returns in life are being out of the herd. Social approval is inside the herd. So if you want social approval, definitely go read what the herd is reading. But it takes a level of contrarianism—saying “No, I’m just going to do my own thing regardless of the social outcome”—to learn anything.

Shane: Do you think there’s some sort of loss aversion there? Once you diverge, you’re pushing out on a Gaussian distribution to one of the tails, and if you feel that you’re going to lose out on that you would rather just stay in the middle?

Naval: Absolutely. I think that’s why the smartest and most successful people I know started out as losers. If you view yourself as a loser—as someone who’s been cast out by society and has no role in normal society—then you will do your own thing and you’re much more likely to find a winning path. It helps to start out by saying “Oh, I’m never going to be popular and I’m never going to be accepted. I’m already a loser. I’m not going to get what all the other kids have. I’m just going to be happy being me.”

Shane: When you’re reading, do you just read and it sticks in your head, or do you take notes? Do you have a system for how you keep track of that or review them?

Naval: I’m both lazy and really focused on being present. I think taking notes is the same as taking photos when you’re on a trip—all it’s doing is taking you out of the moment. And then who really sits there years later and goes back and looks at all their trip photos and gets nostalgic? Just go take your next trip. I just don’t believe in clinging too much to anything from the past—no memories, no regrets, no people, no trips—nothing. A lot of our unhappiness also comes from comparing things from the past to the present. The first time you saw a sunset it was amazing, jaw-dropping; you forgot yourself. The second time you saw it is cool. The hundredth time you say it’s nothing. A thousand times and someone shows you a sunset and you’re like “Well actually I saw this one sunset in Mexico that was really cool”—you’re not even there. So I just don’t believe in clinging too much to memories, and that includes in reading.

I do highlight. I catch myself doing that, but I do it more because it’s just a way of rereading that particular paragraph at that moment in time. Then once in a blue moon, for my especially favorite books, I want to reread the book but I’ll be short on time, so I’ll just read the highlighted passages until something catches my eye and then I get sucked back into the book. But the reality is I could stop highlighting tomorrow and it would make no difference. Note-taking is even harder than that. So I do not take notes. But everyone’s brain works differently. Some people love to take notes.

Actually my note-taking is Twitter. What I do is I really read, and if I have some fundamental “aha” insight or concept, then what I like about Twitter is it forces me to distill that into 140 characters. Then I try and put it out there as an aphorism. And then I get attacked by all kinds of random people who point out all kinds of obvious exceptions and jump down my throat. Why do I do this again?

Shane: When you first pick up a book, are you skimming for something interesting? How do you go about reading it?

Naval: I’ll start at the beginning but I’ll move fast. If it’s not interesting I’ll just start looking ahead. I’ll start skimming or speed-reading. If it doesn’t grab my attention within the first chapter in a meaningfully positive way, I’ll either drop the book or I’ll skip ahead a few chapters. I don’t believe in delayed gratification when there’s an infinite number of books out there. There are so many great books and so many of them that are so well written that you just can’t spend your time on these.

One thing I will do: if I find that early on in the book the author starts making statements that I think are just factually untrue—and one should always be open to new ideas—but if they’re starting to make contradictions, or the epistemological load of acknowledging that would require me to undo my entire lifetime of learning and start over… for example, I had a conversation recently with a guy who sounded really, really smart and was throwing all kinds of science at me and my head was spinning. Then he basically said “And as we know, thermodynamics isn’t really true.” At that fundamental level—that is not even a theory, it’s a law; it comes from the mathematics—I’m out. Then we just have no basis for conversation. So if I find something like that in a book—someone says “Oh yes, I cleared my mind and I watched my thought process and then I was able to levitate”—then I have to put the book down, because now I don’t know what is true and what is false.

Basically what I’m looking for is: is the author knowingly lying or completely deluded? If they are, then I can’t fill my brain with that junk because I can’t separate truth from fiction. Generally I’ll skim, I’ll fast-forward, I’ll try and find a part that catches me. Usually though what happens in most books (most nonfiction books) is they have one point to make. They make it and then they give you example after example after example and apply it to explain everything in the world. Once I feel like I’ve gotten the gist of it, I feel very comfortable putting the book down. There’s a lot of these what I would call pseudoscience bestsellers that are all over. Everyone’s always reading them and people are like “Oh, did you read this book?” and I would say yes, but the reality is I read maybe two chapters of it and I got the gist.


Decision-Making

Shane: I want to switch gears and talk a little bit about decision-making, which is kind of what you get paid to do both as an investor and as the CEO of AngelList. You’re kind of paid to be right when other people are wrong. Do you have a process for how you make decisions?

Naval: Decision-making is everything. In fact, someone who makes decisions right 80% of the time (or even 70%) will be valued and compensated in the market hundreds of times more. People have a hard time understanding that, but that’s a fundamental fact of leverage. If I’m managing a billion dollars and I’m right 10% more of the time than somebody else, that’s a hundred million dollars worth of value on a judgment call. With modern technology and large workforces and capital, our decisions are getting leveraged more and more. So if you can be more right, more rational—and that’s one of the reasons why I love your blog, because it really focuses on helping you be more right, better decision-makers, more rational—then you’re going to just get nonlinear returns in your life.

Decision-making is everything. What the brain is is a memory-prediction machine. Out of the memory of things that worked in the past and what it’s read, it’s trying to predict the future. A lousy way to do memory prediction is “X happened in the past, therefore X will happen in the future.” It’s too based on specific circumstances. What you want is principles. You want mental models. The best mental models that I have found have come through evolution, game theory, and Charlie Munger (who I’m sure you quote a lot on your blog). Charlie Munger was Warren Buffett’s partner, a very good investor, but he has tons and tons of great mental models. Nassim Taleb has great mental models. Benjamin Franklin had great mental models. So I basically load my head full of mental models. But then different ones apply to every situation. I don’t really run a checklist.

For example, I studied a lot of complexity theory when I was younger. It’s a field that I got into and occasionally just dive deep into these things. My most recent one is cryptography, but I was really into complexity theory back in the mid-’90s. The more I got into it, the more I understand the limits of our knowledge and the limits of our prediction capability. That’s been super helpful to me. That has helped me come up with systems that operate in the face of ignorance. I believe that fundamentally we are ignorant and very, very bad at predicting the future. So I don’t look for, and I don’t believe that I have, the ability to say what is going to work. Rather, what I try to do is eliminate what is not going to work. I think being successful is just about not making mistakes. It’s not about having correct judgments—it’s about avoiding the incorrect judgments.

I have mental models around how do I determine if I can trust somebody, around what are the actual odds this is going to work, how much margin of safety do I have. If it works out, the angel bets and venture bets are great because they have asymmetric outcomes: on the positive side you can make 10,000x, but on the downside you can only lose 1x. So I try to rig the game.

I don’t believe in specific goals. I set up systems. Use your judgment to figure out what kinds of environments you can thrive in, and then build a system to create that environment around you that you’re statistically likely to succeed in. I don’t want to be the most successful person on the planet, nor do I want to be. I just want to be the most successful version of me while working the least hard possible. I want to be in a thousand universes where Naval is successful in 999 of them—he’s not a billionaire, but he’s done pretty well in all of them. Whatever the metric is—or he’s happily married in most of them. He may not have nailed it in every regard, but he’s set up systems such that he’s failed in very few places. So basically I just try and set up good systems, and then the individual decisions don’t matter that much, because I think our ability to make individual decisions is actually not great.

For example, as an investor I would rather invest with a system where I want to see 10,000 companies and I want to pick 500 that have a shot of being huge, and then I want the option to double down on the five winners. I don’t want to just look at a hundred companies and pick ten that I think are winners and go all-in on those. I don’t think I have that capability. And I think there’s a lot of ex-post-facto reasoning and origin stories that people make up about why they were successful. But the real separation here is you look at which people are consistently successful. Especially in Silicon Valley there are lots of one-hit wonders. How many people consistently seem to do something interesting, build something interesting, make money, and do something new?

I’m not in this to make money. Money is just a piece of paper. Every time I see one of these billionaire founders giving away money to a hospital or whatever—you know, they overshot; they didn’t need that much money. There’s huge diminishing returns to money after a certain point. Especially now that I’m going for freedom from rather than freedom to, there are things that money does that I can’t do. Literally money in that sense is a boat anchor around my neck, because it is something that I’ve been fearful of losing, something that I’m getting jealousy debates about, so many people want from me. So I’m not even in it for the money. It’s like: can I do something interesting and new? Can I create something brand new the world has never seen that it gets value out of, that it uses, that is congruent with my morals so I never have problems sleeping at night and I never have to worry about selling something that I wouldn’t buy? So much more into that.

I don’t have a checklist system for decision-making. I know that’s like a big thing recently—Atul Gawande wrote The Checklist Manifesto—and there’s good for pilots and surgeons. I don’t think it’s necessarily great for investors. And by the way, that’s another one of those books where you just read the first chapter and you’re done. It’s a great blog post.

I also don’t think you need to be that hard on yourself. A lot of what goes on today, a lot of your listeners right now, are beating themselves up and scribbling notes and saying “I need to do this and I need to do that.” No—you don’t need to do anything. All you should do is what you want to do. And if you stop trying to figure out how to do things the way other people want you to do them, then you get to listen to that little voice inside of your head that wants to do things a certain way. And then you get to be you. And no one in the world is going to beat you at being you. You’re never going to be as good at being me as I am, and I’m never going to be as good at being you as you are. So certainly listen, absorb—but don’t try and emulate. It’s a fool’s errand. Instead each person is uniquely qualified for something. They have some specific knowledge, capability, and desire that nobody else has—just purely from the combinatorial of human DNA and development. So your goal in life is to find the people who need you the most, to find the business that needs you the most, to find the project and the art that gives you the most, because there’s something out there just for you. What you don’t want to do is be building checklists and decision frameworks built on what other people are, because you’re never going to be good at being somebody else. And you’re inevitably going to miss stuff too with checklists.


Evaluating People: Integrity, Intelligence, Energy

Shane: You mentioned kind of how you determine if you can trust somebody. I know you’ve said in the past that you kind of use Buffett’s criteria for evaluating people, which is the combination of intelligence, energy, and integrity. What predictive signals do you pay attention to for each? How do you determine if you can trust someone?

Naval: Integrity is the hardest one. It usually comes out in two ways. One is long-term: you’ve known somebody for a while and you kind of know how they think about things. The more interesting one is the short-term one, which is just kind of see how they treat other people. There are lots and lots of people who will not screw you over (screw is a strong word), but they will do something that is self-dealing or slightly unethical relative to another business partner. When the whole thing fails they’ll say to you that night, with a wink-wink, “I was taking advantage of that person because they deserve it, but you’re my friend—I would never do that to you.” The thing is, it’s very easy to change your definition of who friends are.

I find the people who really do things out of integrity have an internal moral compass. They don’t do unfair or unethical or bad deals with other people because it would soil their own view of themselves and they wouldn’t be able to sleep with themselves at night. Some of the highest-integrity people I know—the worst thing you can do is accuse them of something self-dealing. They will get so unhappy because they’ll be like “Oh no no no, that’s not who I am. I can’t be that person.” And they’ll bend over backwards. Usually I find that people you’re negotiating with who are high integrity—deals are very easy to negotiate with them. They’ll give you things that they don’t need to give you because they think it’s fair, and vice versa. Negotiations with high-integrity people are usually very easy. You’re giving each other things to make sure the other person is happy enough that the deal survives, because unhappy deals get unwound and they become short-term relationships which don’t have any compounding benefits.

Finally, if someone is going around and talking about how honest they are, they’re probably dishonest. Just a little telltale indicator I’ve learned: when someone spends too much time talking about their own values or talking themselves up, they’re covering for something.

There’s actually a good book—it’s kind of out of print, I think it’s hard to track down, maybe find it online somewhere—and it’s not the obvious one. The name of the book is The Art of Manipulation. I found it because of a tweet that I followed from someone. It was really good because the guy basically goes undercover, lives with con men, spends time with them running cons and learning all about cons. Without judgment he just lays down how con men work and how to spot them when they’re being dishonest. Some of the telltale signs are: they’ll push the deal a little bit too hard, they’ll sell just a little bit too hard, they’ll talk about how honest they are.

I have great people in my life who are extremely successful, very desirable—everybody wants to be their friend—very smart, and yet I’ve seen them do one or two things that are slightly not great to other people. The first time I’ll tell them. I’ll say “Hey, look, I don’t think you should do that to that other person—not because you won’t get away with it (you will get away with it), but because it’ll hurt you in the end. Not in some cosmic karma kind of way, but just: I believe that deep down we all know who we are. You cannot hide anything from yourself. Your own failures are written within your psyche and they’re obvious to you. So if you have too many of these moral shortcomings you will not respect yourself. And the worst outcome in this world is not having self-esteem. If you don’t love yourself, who will?” So I think that you just have to be very careful about doing things that you are fundamentally not going to be proud of, because they will damage you. The first time around I warn them. By the way, nobody changes. Then I just kind of distance myself from that and cut them out of my life.

I just have this saying inside my head: the closer you want to get to me, the better your values have to be. When I met my wife it was a great test, because I really wanted to be with her and she wasn’t so sure at the beginning. In the end we ended up together because she saw my values. And I’m lucky I had developed them by that point, because if I hadn’t I wouldn’t have gotten her. Not that I own her or anything—there’s no attachment like that—but I wouldn’t have deserved her. As Charlie Munger says: to find a worthy mate, be worthy of a worthy mate. Working on your values is long-term selfish, although short-term it absolutely involves sacrifices. If being ethical were profitable, everybody would do it. You wouldn’t have to have a separate concept. There would be no books on it. No one would ever tell you “my values are going to be profitable.” But it’s not. It’s obviously unprofitable. It involves sacrifices. But like everything in life, if you’re willing to make the short-term sacrifice you’ll have the long-term benefit.

My physical trainer, a really wise, brilliant guy, always says: easy choices, hard life; hard choices, easy life. Basically if you’re making the hard choices right now—what to eat (you’re not eating all the junk food you want), you’re making the hard choice to work out—then your life long-term will be easy. You won’t be sick, you won’t be unhealthy. Same is true of values. Same is true of saving up for a rainy day. Same is true of how you approach your relationships. But if you make the easy choices right now, your overall life will be a lot harder.

Shane: How do you separate the people who know what they’re talking about from the people who pretend they know what they’re doing? We’re full of a world where it’s so easy to pretend you have knowledge that you don’t actually have.

Naval: Real knowledge is intrinsic and it’s built from the ground up. Going back to my math example earlier: you can’t understand trigonometry without understanding arithmetic or geometry. Basically if someone is using a lot of fancy words and a lot of big concepts, they probably don’t know what they’re talking about. I think the smartest people can explain things to a child. If you can’t explain it to a child then you don’t know it. That’s a very common saying, but Richard Feynman very famously, if you go into his lectures (Six Easy Pieces, his early physics lectures), has one where he basically explains mathematics in three pages. He starts from the number line and counting and then he goes all the way to precalculus, and he just builds it up through an unbroken chain of logic. He doesn’t rely on any definitions. For example, if somebody says “Oh, that bird is called this” or “the rule for this thing is that,” they’re not really telling you anything fundamental. They’re telling you about humans; they’re telling you about naming systems. True understanding is about algorithms, about understanding how things connect to each other.

I think it’s the mark of a charlatan to try and explain simple things in complicated ways. It’s the mark of a genius to explain complicated things in simple ways. So really they should be able to do it very, very, very simply. I have to catch myself on this because I have a big vocabulary (because I read a lot), so I can sound smarter than I am just by using big words. But in the process I’m being dishonest with myself. It’s okay to use more precise words—English is a big language with a lot of words, and that allows for a lot of precision. But if you’re deliberately using words that your audience doesn’t know, or if you even think you’re using a word that your audience doesn’t know and you don’t catch yourself and correct that, then you’re essentially being dishonest. You’re just trying to show off. You’re trying to pull one over their eyes.

There’s a great book by Randall Munroe (who is the creator of xkcd, that very science-oriented comic) called Thing Explainer. It’s a reference to the Saturn V rocket that took the Apollo missions into space. What he’s doing in that book is he explains all these very complicated concepts—all the way from climate change to physical systems to submarines and so on—but he does it using only the thousand most common words in the English language. That’s why he calls the Saturn V rocket “Up Goer Five”—because you can’t define a rocket as a spaceship or a rocket; it’s self-referential. He says “this thing that goes up,” and kids get that right away.

There’s another great book that I call Thinking Physics. I open this one all the time and I love it. On the back cover it has this great little pitch: it says it’s the only book that’s used in both grade school and graduate school. It’s true. It’s all simple physics puzzles that can be explained to a twelve-year-old child (they can puzzle over it) and can be explained to a 25-year-old grad student in physics. They all kind of have fundamental insights into physics. They’re all kind of tricky, but anyone can get to the answer through purely logical reasoning.

I love reading the history of how scientists came up with their various breakthroughs. If you have ever gone through general relativity—relativity is a fascinating thing. It’s a very advanced concept, but in a way it’s very simple because Einstein came up with it with what are called Gedankenexperiments (fancy word for thought experiments—it means “thought experiment” in German). He was able to basically just do logical thought experiments in his mind until he came up with relativity, and then he formalized the mathematics and made predictions that were later unfalsifiable. Really brilliant physicists like that get there by pure reasoning and pure logical reasoning. It’s not like he had to go draw lots of complicated diagrams. He just understood things at a very basic, fundamental level.

Again, this goes back to: I think the really smart thinkers are clear thinkers, and they understand the basics at a very, very fundamental level. I would rather understand the basics really well than have memorized all kinds of complicated concepts that then I can’t stitch together and I can’t re-derive from the basics. If you can’t re-derive it from the basics, then if you need it you’re lost.

Shane: It seems like a large part of making effective decisions kind of boils down to dealing with reality. How do you make sure you’re dealing with reality when you’re making decisions?

Naval: By not having a strong sense of self or judgments or mind presence. The monkey mind will always respond with regurgitated emotional responses to what it thinks the world should be, and that will cloud your reality. This happens a lot of times when people are mixing politics and business. For example, in January this year I wrote a little piece on the election that kind of predicted that Trump or Bernie is going to win—one of those two characters is going to win. That’s not what I wanted to have happen necessarily. I’m an elite; my life is pretty good. I’m not looking for rabble-rousers to change everything. But I wanted to see reality the way it was, as opposed to the way I wanted it to be.

I think the number-one thing that clouds us from being able to see reality is just that we have preconceived notions of the way it should be. One definition of a moment of suffering is that moment when you see things exactly the way they are. This whole time you’ve been convinced your business is doing great and really ignoring the signs that it’s not doing that well—then your business fails and then you suffer. Well, it’s just because you’ve been putting off reality, even hiding it from yourself. So the good news is that when you’re suffering, when you’re in pain, that’s a moment of truth. There’s a moment where you’re forced to embrace reality actually the way it is. And then you can make meaningful change and progress, because you can only make progress when you’re starting with the truth.

I think the hard thing here is seeing the truth. To see the truth you have to get your ego out of the way, because your ego doesn’t want to face the truth. So the smaller you can make your ego, the less conditioned you can make your reactions, the less desires you can have about the outcome you want, the easier it is to see the reality.

A clearer example of this is when we’re going through difficult things like a breakup or a job loss or a business failure or a health problem, and our friends are advising us. When we’re advising them, the answer is so obvious it comes to us in a minute and we tell them exactly: “Oh, that girl—get over her. She wasn’t good for you anyway. You’ll be happier. Trust me, you’ll find someone.” You know what the correct answer is. But that person can’t see it because in that moment of suffering and pain they’re still wishing that reality was different. So the problem is not reality. The problem is their desire colliding with reality. It’s preventing them from seeing the truth no matter how much you say it. The same thing happens when I’m making decisions. The more of a desire that I have that it work out a certain way, the less likely I am to see the truth. Especially in business: if something isn’t going well I try to acknowledge that publicly, and I try to acknowledge it publicly in front of my co-founders and friends and co-workers. Because that way I’m not hiding it from anybody else. If I’m not hiding it from anybody else, then I’m not going to basically delude myself about what’s actually going on.

You’ve said anything you can think of has been thought of and tried. The only way you’re going to find something is if you stick to it at an irrational level and try a whole bunch of things. This kind of makes the idea a commodity, but the judgment and execution incredibly rare. How do you evaluate if someone is picking the right idea and if they have the capacity to execute on that idea?

Naval: The best founders I’ve found are the ones who are very long-term thinkers. Even decisions that maybe they shouldn’t care that much about early on, they fixate on because they are not building a house—they’re putting bricks in the foundation of a skyscraper, at least in their minds. So what you’re looking for is someone who knows the space well, who understands how difficult it’s going to be, but doesn’t care because they just love whatever they’re doing. They’re into it and they commit to it for the long haul. Passion and vision alone are not enough. Steve Case said that vision without execution is a hallucination. Execution alone isn’t enough. And then unfortunately, at least in technology businesses, there’s a lot of luck required—right place, right time, market forces, timing, regulatory action against or pro. There’s a lot of things we don’t control: where the platforms are sitting, what open-source efforts show up. So you can never predict the outside successes. But what you can predict are the failures. You can say “Oh, this person doesn’t know this field at all—they’re out of their depth,” or “This person is a short-term thinker—they’re not going to last the game. They’re not going to go as far as needed.”

As I was saying, there are no new ideas. All the ideas have been thought. But it’s about the combination of the idea plus the execution plus the passion. Steve Jobs was a visionary and a great designer not because he came up with the idea to build a smartphone—many people had tried to build a smartphone—but because he had a very high bar for the design, he understood the manufacturing tolerances and what the technology was capable of and what it wasn’t, and he could rally the people and the resources to get it done. He actually didn’t care about the financial outcome. He took a $1 salary from Apple. He just wanted to see it done, and he was willing to do it for as long as it takes until it worked. So it’s kind of a magical combination of factors. And then the timing in the world happened to be right, the technology was around, Jony Ive was there, and who knows how many other factors intersected to make it happen. But just as many factors intersected on his side, there were ones that intersected against him. For example he had taken over Apple, which was a horribly failing company at the time. The poor guy died of pancreatic cancer—he got taken out early. Think about what more he could have created, what more he could have done for the world. He probably wasn’t happy in the whole process. He drove himself into the ground.

I think you do have to be irrationally optimistic to succeed, and passionate, but you also have to really know your stuff. I meet a lot of entrepreneurs where they’re short-term thinkers, in which case that’s okay—it just means this is not the thing for you. Go find the thing you can commit to for 10 years, because that’s how long it’s going to take minimum to get a good outcome. And you have to enjoy the journey, because there’s no guarantee on the outcome. And you have to be really, really good at it, which means that you probably love it so much that you’re willing to put in the time before there’s even any return on it. So I think the best founders have a deep understanding of the space—deep enough to be contrarian—and they have a deep passion for it so that they’ll just keep working on it, and they have execution skills: they just get things done, they solve problems, they’re capable.


Rational Buddhism

Shane: You’ve kind of called your philosophy “rational Buddhism.” How does that differ from traditional Buddhism, and what type of exploration did you go through to arrive at that?

Naval: The “rational” part means that I have to reconcile it with science and evolution, and I have to reject all the pieces that I can’t verify for myself. For example: is meditation good for you? Yes. Is clearing your mind a good thing? Yes. Is there a base layer of awareness kind of below your monkey mind? Yes. All these things I’ve verified for myself. And some of the beliefs that come out of Buddhism I believe and follow because again I’ve verified them or reasoned them with thought experiments myself.

But what I will not accept is things that are written down just so—like “Oh, you’re this in the past lives and you’re paying off the karma for…”—where I haven’t seen it. I don’t remember any past lives. I don’t have any memory. So I just have to not believe that. Or when people say “Your third chakra is opening and your second chakra is…”—I don’t know, this is fancy nomenclature. I have not been able to verify or confirm any of that on my own. So if I can’t verify it on my own or if I cannot get there through science, then it may be true, it may be false, but it’s not falsifiable, so I cannot view it as a fundamental truth.

On the other side, I do know that evolution is true. I do know that we are evolved survival and replication machines. I do know that we have an ego so that we get up off the ground and worms don’t eat us—we actually take action. So what “rational Buddhism” to me means is understanding the internal work that Buddhism espouses to make yourself happier and better off and more present, more in control of your emotions, and being a better human being—but I don’t subscribe to anything fanciful just because it was written down in a book. I don’t think I can levitate. I don’t think that meditation is going to give me superpowers and those kinds of things. So it’s basically: try everything, test it for yourself, be skeptical, keep what’s useful, and discard what’s not.

I would say my philosophy falls down to two poles. On one pole is evolution and the binding principle, because it explains so much about humans. On the other side is Buddhism, which is the oldest, most time-tested spiritual philosophy on the internal state of being inside each of us. And I think those are absolutely reconcilable. I actually want to write a blog post at some point about how you can map the tenets of Buddhism—especially the non-fanciful ones—directly into a virtual-reality simulation. What I mean by that is: if you believe we’re living in a VR sim (which I know some people are spouting) or you believe the Buddhist view of the world with samsara and nirvana and all that, you would actually come to the same conclusions on how to move through your life.

Shane: What are the areas of your life right now that you’d like to change the most, and why?

Naval: I would like to be less time-bound and less greedy about signing up for things. I don’t know how to describe it. You know what it really is? I had a tweet recently where I was going back and forth with somebody and they came up with this concept of there should be two-factor authentication on your calendar. Exactly. There’s two-factor authentication when you’re logging into a website so that if your password gets stolen the attacker doesn’t have your phone, so they can’t log in because the phone generates a unique code. Well, I wish there was a two-factor code against my calendar, because current me—present me—is always making promises for future me. Current me is tired and exhausted and hungry and wants to go home and go to sleep and wants to read a book and wants to hang out with the wife and baby. But future me is this dynamic, high-energy individual who will always show up to every meeting and will have a lot of energy and will want to get a lot of things done. So I commit myself to all these commitments in the future that, when the future me arrives, actually it’s present me who is lazy and hungry and tired. So I want two-factor authentication against myself. The way I would like to do that is: every time I make a commitment to anything, I should instead just write it down and then check back in 48 hours later with a clear mind and say “Do I still commit to doing this?” Or even better would be saying: if I commit to doing something, I should be willing to do it right now. If I’m not willing to do it right now, then don’t do it—don’t commit to it. That’s the Derek Sivers approach: if you’re not saying “hell yes” right now, then you should just be saying no. I think this is something every busy person struggles with. I just want to be much better at managing my own time.

You go through life through an exploration phase and then you switch to an exploitation phase. I’m very much in the exploitation phase. I’m not looking for more exploration. But all that said, I have a hard time saying no. If I had one wish, the most important thing to me would be that I would constantly be running my mind in debug mode. I would literally be watching every single thought I have and letting no reaction pass without being stopped, inspected, stripped, searched, examined, understood, and then let go. But the reality is that there’s a lot of time, and we’re just highly conditioned creatures. So a lot of my goals over the next few years are unconditioning earned responses or habituated responses so that I can make decisions more cleanly in the moment without relying upon memory or prepackaged heuristics and judgments.

Shane: What’s the most common mistake you see people make over and over?

Naval: It’s a very tough question—so contextual. It really depends on the context. I think the most common mistake, if I look out there on planet Earth for humanity, is the idea or the belief that you’re going to be made happy because of some external circumstance. And I know that’s not original, that’s not new—that’s fundamental Buddhist wisdom—so I’m not taking credit for it. But I think I really just recognize it now at a fundamental level, including in myself. Like we just bought a new car with the baby so we need a bigger car. We were driving a little Mini Cooper before—not enough room in there—so we bought a new car. And now I’m waiting for the new car to arrive, and of course every night I’m on the forums reading about the car. Why am I doing this? It’s still the same object—a sleek car. It’s not going to change my life that much. And I know that the instant the car arrives I won’t care about it anymore. But what it is is I’m addicted to the desiring. I made a big deal of it. I’m addicted to the idea that this external thing is going to bring me some kind of happiness and joy. And this is completely delusional.

I think just looking outside for anything is the fundamental delusion. I would not just say you shouldn’t do things outside—you absolutely should. You’re a living creature. You know, there are things that you do: you locally reverse entropy. That’s why you’re here. You’re meant to do something. You’re not just meant to lie there in the sand and meditate all day long. So you should act. You should do what you’re meant to do. But the idea that you’re going to change something in the outside world that is going to bring you the peace and everlasting joy and the happiness that you deserve—that is a fundamental delusion that we all suffer from, including me. And so the mistake over and over and over is to say “Oh, I’ll be happy when I get that thing”—whatever that is. That’s the fundamental mistake that we all make, including me, 24/7, all day long.


Meaning and Purpose of Life

Shane: I want to end with a really unbounded big question, which is: what is the meaning and purpose of life?

Naval: It’s a big question. I’ll give you three answers, because it’s a big question.

One: It’s personal. You have to find your own meaning. Any piece of wisdom that anybody else gives you—whether it’s Buddha or me—it’s going to sound like nonsense. So I think fundamentally you just have to find it for yourself. The important part is not the answer—it’s the question. You have to sit there and dig with the question. It might take you years or decades. But when you find an answer you’re happy with, that will be fundamental to your life.

Two: There is no meaning to life. There is no purpose to life. Osho says it’s like writing on water or building houses in sand. The reality is you’ve been dead for the history of the universe—ten billion years or more. You will be dead for the next 70 billion years or so until the heat death of the universe. And anything you do will fade. It will disappear. The human race will disappear. The planet will disappear. Your lineage will disappear. So no one’s going to remember you past a certain number of generations—whether you’re an artist or a poet or a conqueror or a pauper or nothing. So there’s no meaning. You have to create your own meaning. Which is what about? Until you have to decide: is it a play that I’m going through that I’m just watching? Is there a self-actualization dance that I’m doing? Is there a specific thing that I just desire just for the heck of it? But these are all meanings you are making up. There’s no fundamental, intrinsic, purposeful meaning to the universe. Because if there was, then you would just ask the next question yourself: “Well, why is that the meaning?” And it would just be, as Richard Feynman said, turtles all the way down. Why? You just keep accumulating. There is no answer you can give that question that wouldn’t have another “why.” And I don’t buy the everlasting afterlife answers, because it’s insane to me—with absolutely no evidence—to believe that because of how you lived 70 years here on this planet, then you get to spend an eternity (which is a very long time) in some afterlife. What kind of silly God judges you for eternity based on some small period of time here? So I think that after this life it’s very much like before you were born. Remember that? It’s going to be just like that. And before you were born you didn’t care about anything or anyone—including your loved ones, including yourself, including humans, including whether we go to Mars or whether we stay on planet Earth, and whether there’s an AI or not. You just don’t care.

I met this entrepreneur who was obsessed with Steve Jobs and he was making all these sacrifices trying to be like the next Steve Jobs. I said “Do you want to be exactly like Steve Jobs right now?” He said yes. Steve Jobs is dead. He doesn’t care about anything. He’s got like zero. He’s not registering at all. So if you want to be like Steve Jobs, you don’t want to be like Steve Jobs. Just be you. Right now he would trade places with you in an instant if he could. So I don’t think there’s any real meaning or purpose to life.

Three: A little more complicated than that. From what I’ve been reading in science, friends of mine have written books on this, kind of stitched-together theories—maybe there is a meaning to life, but it’s not a very satisfying purpose. Basically in physics, the arrow of time comes from entropy. The second law of thermodynamics is that entropy only goes up, which means disorder in the universe only goes up, which means concentrated free energy only goes down. And if you look at what living things are—living systems, humans, plants, civilizations, what have you—these are systems that are locally reversing entropy. Humans locally reverse entropy because we have action. But in the process we globally accelerate entropy until the heat death of the universe. So you could come up with some fanciful theory (which I like) that we’re headed towards a heat death of the universe where there’s no concentrated energy, where everything is sort of at the same energy level, and therefore we’re all one thing—we’re essentially indistinguishable. And what we are doing as living systems is accelerating getting to that state. So the more complex of a system you create—whether it’s through computers and civilization or through art and mathematics or just through creating a family—you’re actually accelerating the heat death of the universe. So you’re pushing us toward this point where we end up as one thing. But I think that’s kind of an unsatisfying answer if you’re looking for personal meaning today in your life.


Shane: That was phenomenal. Listen, thank you so much. This was just absolutely mind-blowing. I really appreciate it. Where can people find you?

Naval: Twitter at @naval or on my blog at startupboy.com. And thank you so much. Thank you. It’s been great.


Shane: Hey guys, this is Shane again. Just a few more things before we wrap up. You can find show notes at FarnamStreetBlog.com/podcast. You can also find information there on how to get a transcript. And if you’d like to receive a weekly email from me filled with all sorts of brain food, go to FarnamStreetBlog.com/newsletter. This is all the good stuff I found on the web that week that I’ve read and shared with close friends, books I’m reading, and so much more. Thank you for listening.

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