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Tim FerrissTim Ferriss

The Person I Call Most for Startup Advice — Naval Ravikant

Take 10 seconds and sign up for my free "5-Bullet Friday" newsletter: https://go.tim.blog/5-bullet-friday-yt/ Each Friday, you’ll get a short email from me with five things I've discovered that week, sending you off to your weekend with fun and useful things to ponder and try. 🙌 Naval Ravikant (@naval) is the CEO and a co-founder of AngelList. He previously co-founded Epinions, which went public as part of Shopping.com, and Vast.com. He is an active angel investor and has invested in more than 100 companies, including more than a few “unicorn” mega-successes. BUT, even if you have zero interest in startups or investing, this episode is well worth your time. This is really about the habits and beliefs of a highly successful (and happy) person. Naval has refined his way of living in very unique ways, and you can borrow what he’s learned, read the books that have changed him, and experiment with the habits he has developed through trial and error. Connect with Naval Ravikant: Follow Naval Ravikant on Twitter: https://twitter.com/naval The Person I Call Most for Startup Advice Show Notes: https://tim.blog/2015/08/18/the-evolutionary-angel-naval-ravikant/ Intro [0:00] On the intensity of Naval Ravikant [6:55] On uncompromising honesty [16:54] How AngelList and Venture Hacks came to be [20:09] What Naval looks for when deciding to invest in a founder [25:24] Common “wives tales” in venture capital [32:39] What books, outside the startup world, have most improved Naval’s ability to invest? [36:54] Greatest investing hits and misses [51:49] When you think of the successful people, who is the first that comes to mind? [58:19] Meditative practices [1:00:58] How to replace bad habits with good habits [1:07:06] On setting stakes and awards [1:24:49] How to treat your life like a movie [1:34:44] Overused words and phrases [1:39:39] Early life education and the importance of “loving to read” [1:43:19] Advice for his younger self [1:51:09] Describing the first 60 minutes of each day [1:52:40] If you could have one billboard anywhere, where would it be and what would it say? [2:04:19] SUBSCRIBE: http://bit.ly/1dSzTkW About Tim Ferriss: Tim Ferriss is one of Fast Company’s “Most Innovative Business People” and an early-stage tech investor/advisor in Uber, Facebook, Twitter, Shopify, Duolingo, Alibaba, and 50+ other companies. He is also the author of five #1 New York Times and Wall Street Journal bestsellers: The 4-Hour Workweek, The 4-Hour Body, The 4-Hour Chef, Tools of Titans and Tribe of Mentors. The Observer and other media have named him “the Oprah of audio” due to the influence of his podcast, The Tim Ferriss Show, which has exceeded 200 million downloads and been selected for “Best of iTunes” three years running. Connect with Tim Ferriss: Visit the Tim Ferriss PODCAST: https://bit.ly/2rYjUBr Visit the Tim Ferriss BLOG: http://bit.ly/17jDHw3 Like Tim Ferriss on FACEBOOK: http://on.fb.me/1avYUxq Follow Tim Ferriss on TWITTER: http://bit.ly/17d94TE Follow Tim Ferriss on INSTAGRAM: http://bit.ly/2IfH37J Follow Tim Ferriss on INSTAGRAM: http://bit.ly/2IfH37J

Tim FerrisshostNaval Ravikantguest
Oct 29, 20152h 16mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:00 – 2:21

    Cold open banter: intensity, altitude, and “cybernetic organism” jokes

    1. TF

      Optimal minimal At this altitude, I can run flat out for a half mile before my hands start shaking.

    2. NR

      Can I ask you a personal question? Now we're receiving a perfect image.

    3. TF

      What if I give you alcohol?

    4. NR

      I'm a cybernetic organism. Living tissue over metal endoskeleton.

    5. TF

      The Tim Ferriss Show. This episode is brought to you by 99designs, your one-stop shop for all things graphic design related. I've used 99designs for everything from banner ads to book covers, including sketches and mock-ups that led to The 4-Hour Body, which later became number one New York Times, number one Wall Street Journal. And the brainstorming, a lot of it took place with designers from around the world, and here's how it works. Whether you need a T-shirt, a business card, a website, an app thumbnail, whatever it might be, you submit that project, and designers from around the world will send you sketches and mock-ups and designs. You choose your favorite, and you have an original that you love, or you get your money back. It's that straightforward. And many of you who are listening have already used it and created some amazing things that I'll be sharing in the future. But in the meantime, if you wanna see some of my competitions, some of the book covers, as well as get a free $99 upgrade, go to 99designs.com/tim. That's 99designs.com/tim. This episode is brought to you by Athletic Greens. I get asked all the time, "If you could only use one supplement, what would it be?" And my answer is inevitably Athletic Greens. It is your all-in-one nutritional insurance. I recommended it in The 4-Hour Body. Did not get paid for that. And I travel with it to avoid getting sick. I take it in the mornings to ensure optimal performance. It just covers all my bases if I can't get what I need through whole food meals throughout the rest of the day. And you can get 50, oh my gosh, 50% off. Yes, 50% off if you go to athleticgreens.com/tim. That's athleticgreens.com/tim. Check it out. It's tasty, but more important, it will help you not screw up when you're doing your nutritional planning. So for me, just covers the bases, takes a load off my mind, puts a lot in my body. And, uh, check it out, athleticgreens.com/tim.

  2. 2:21 – 6:08

    Show format and Naval’s background: why Tim wanted this conversation

    1. TF

      Hello, my frisky little kittens. This is Tim Ferriss, and welcome to another episode of The Tim Ferriss Show, where it is my job to deconstruct world-class performers to tease out the routines, the habits, the influences, such as favorite books and so on, that have made them good at what they do. And the intention, of course, is to unearth the things that you can borrow, that you can replicate in your own life ASAP. And the guests range from chess prodigies to hedge fund managers to celebs to fill in the blank. And this time we have fill in the blank, which is a world-class entrepreneur, builder, and investor. His name is Naval Ravikant. Naval is the CEO and co-founder of AngelList. He is a close friend, has become a even closer friend because I am now an advisor to AngelList. He previously co-founded Epinions, which went public as part of Shopping.com and, uh, Vast.com also. He is a very active angel investor, not surprisingly, and has invested in more than 100 companies, including more than a handful of unicorn, so-called unicorn mega, mega, mega, mega, I think I'll just say that again, mega successes. His deals include Twitter, Uber, Yammer, Postmates, Wish, Thumbtack, and OpenDNS, which Cisco just bought for $635 million in cash. There are many more, and you can find many examples on his AngelList page, which is just angel.co/naval. If you wanna see mine, it is angel.co/tim. And AngelList is one of the most incredible tools for investing, matching opportunities and investors that I've ever, I've ever seen, and it's very, very, uh, disruptive to the venture capital space. Uh, there were, I think around 10 people who were introduced to Uber way back in the day as investors and given the opportunity on AngelList. This was around 2010. Uh, I have led a couple of deals including Shyp, S-H-Y-P, you can check them out, shyp.com, which is I think around 40x up in its valuation from the first time that I put it on AngelList and made it available to people like yourselves, uh, uh, who are accredited investors. So you can check out all of my startup deals at angel.co/tim. But let's talk about Naval and why he's on the podcast. Naval's on the podcast because he is a very deep thinker who is very good at asking questions and testing, in other words, questioning the obvious. And that practice and the practice of being hyper-rational when other people are emotional has allowed him to be very successful in the world of investing. But it translates to many other sectors of life and business, and that is why even if you have no interest in early stage investing, I highly, highly encourage you to listen to this. Much like the Chris Sacca episode, uh, Naval has had a huge impact on my own thinking about the world and startups and investing, but not only money, my time, my energy, and he's been very much a mentor in that capacity and many others. So I hope that my enthusiasm and enjoyment in this interview translates to the same for you. He is a treasure trove of many recommendations, and, uh, there, you will probably take down a lot of notes. Uh, but you can find the links to the books and so on in the show notes, and the show notes are at fourhourworkweek.com/podcast, all spelled out, fourhourworkweek.com/podcast. And without further ado, please enjoy Naval Ravikant Naval, welcome to the show.

    2. NR

      Thanks for having me, Tim.

    3. TF

      I have, uh, really been looking forward to this because I always enjoy sitting down in this somewhat artificial formal setting to talk with close friends [laughs]

    4. NR

      [laughs]

  3. 6:08 – 8:13

    “What do you do?” Naval’s dislike of repeating problems and his day job at AngelList

    1. TF

      ... because it gives me the opportunity to do something that would never work in, say, a dinner or sitting down, which is basically have a w- a unidirectional Charlie Rose experience of, of lobbing questions at you. So I'm, I'm actually pretty stoked to jump into it. Um, the first thing that I wanted to ask is, I suppose, a pretty basic one, but when people ask you, what do you do, how do you answer that?

    2. NR

      Oh, very poorly. Um, I, I fundamentally at heart am an entrepreneur, and, uh, any day in which I solve the same problem twice in a row, I'm pretty unhappy. [laughs]

    3. TF

      [laughs]

    4. NR

      So by definition, you know, I, I like to do something different every day. Uh, and I think all humans are sort of meant to do that kind of thing. The, the idea that we repeat ourselves and we specialize and we pigeonhole ourselves is a modern invention created through specialization of labor in the Industrial Revolution. Uh, and hopefully as more and more people move up Maslow's hierarchy of needs, we're gonna be able to, uh, define ourselves much more loosely. So that's a good way of dodging your a- your question. [laughs] Now let me actually answer it.

    5. TF

      [laughs]

    6. NR

      Uh, my day job is I am co-founder and CEO of AngelList, uh, which is kind of the world's largest platform for online fundraising and recruiting for startups. Uh, we're bringing venture capital online. Uh, we have lots of great, uh, lead investors, essentially, uh, mini micro venture capitalists who can, uh, do deals on the platform, and, uh, allows anyone who is sufficiently wealthy and sophisticated to invest behind them. And we also run a large marketplace for introducing talent to startups, uh, where we have over 10,000 companies recruiting now. We have hundreds of thousands of, uh, candidates who are looking to join great startups, and we're making, uh, over 10,000 introductions, mutual introductions every single week, uh, between candidates and startups. Um, so that's kind of my day job. Uh, but the reality of what I do on a day-to-day basis is just completely different.

    7. TF

      Now, the-

    8. NR

      Uh.

    9. TF

      It's just, go ahead

    10. NR

      ... go ahead.

  4. 8:13 – 16:46

    Intensity vs. happiness: competitiveness, calm, and a difficult childhood

    1. TF

      So no, I wanted to, to talk about two seemingly opposed, maybe they're complementary characteristics of yours that I've observed. The first I thought I'd introduce just via s- via a, a story. So we have a mutual friend who's a salty old Polish trainer who I won't mention by name, and you actually introduced me to him. He does a lot of incredible Olympic lifting, and he is one of the most aggressive, intense human beings I've ever met in my life. And of all of the people that he and I know mutually, he's like, "Naval, that guy is intense. That guy is intense."

    2. NR

      [laughs]

    3. TF

      So why [laughs] , why does, why does he have that opinion of you? And, uh, do you agree with it? What is that?

    4. NR

      Uh, yeah, it's actually interesting. I think at my core level, I am an extremely intense person, very competitive. Um, I have this huge drive to win. Uh, I always wanna be right. I usually research the hell out of any topic I get into and learn 80% of it very quickly, and I take nothing at face value. So I'm always kind of questioning and, and, uh, deciding. And when I first met this gentleman who, uh, just like you, he's transformed my life, actually. He's made me healthier and fitter than I've ever been. Um, and he, and I consider him incredibly intense. Uh, I pushed back on him. I mean, there were things that he said that I thought were smart, that I could corroborate, um, that I took, uh, as he had handed them. And there were things that he had said that contradicted my own experience in reading, and so I dismissed them. So I think he was little ... He might refer to me as being intense because I have my own point of view on everything, uh, or everything that matters.

    5. TF

      [laughs]

    6. NR

      That said, uh, I've probably spent the last half decade of my life, like all of us who are getting a little older, being, uh, much more introspective, uh, much more aware of my own foibles, and trying to be a much calmer person, uh, and trying to be less stressed and more happy and more in the moment. And part of that means learning how to control the intensity, dial it up and dial it down. And that's, that's a contradiction that we all deal with, that we all want to be successful people, but we also want to be happy people. And the two of those run in almost diametric opposites to each other. And if you look at all the new wisdom, uh, the new wisdom is if you walk into an airport bookstore, you open up Time magazine, it's all about, you must be like Elon Musk or Larry Page. It's all about success, success, success. And because we live in this mythology of anyone can achieve the American dream, if you're not successful, if you're not Tim Ferriss, then you're a loser. Um, and that's a terrible-

    7. TF

      Or if, or if you're Tim Ferriss and you're not Elon Musk, you're also a loser, right? [laughs]

    8. NR

      You're also a loser. That's right. There's always, there's always someone higher up the stack. Uh, so the success driven mentality drives you to unhappiness. And if you, if you wanna be successful, surround yourself with people who are more successful than you are. But if you wanna be happy, surround yourself with people who are less successful than you are.

    9. TF

      Mm.

    10. NR

      So, so this is the, the contradiction that we deal with all day long because we're also told that the American dream will bring you happiness, and it will not. I think a lot of us learn as we get older that happiness is internal. Happiness is a choice that you make and it a skill that you develop. And so how do you do that? And that's the fundamental contradiction, and that's why, uh, our mutual friend can consider me, uh, incredibly intense. And I, and by the way, I hope you'll have him on the show someday because I think-

    11. TF

      Oh, yeah

    12. NR

      ... he has incredible wisdom, uh-

    13. TF

      Yeah

    14. NR

      ... to pass along. Uh, so th- that's where the intensity comes in, the desire to be successful. Uh, and at the same time, the non-intensity comes in-

    15. TF

      [laughs]

    16. NR

      ... which is the desire to be happy.

    17. TF

      So, so w- let's call him, uh, let's call him Victor. We'll just call him Victor.

    18. NR

      All right.

    19. TF

      So Victor, my ... What I expect would likely happen if I had Victor on this podcast is he would just spend 60 minutes berating me and telling everyone how fat I was and unimportant [laughs]

    20. NR

      [laughs]

    21. TF

      I think it would be very hard to steer him away from the, the beat Tim with a, you know, leather whip, uh, routine. But yeah, he's a fascinating guy, so I'll have him on at, at some point. The intensity, I'd love to ask just of some follow-ups about that because Uh, your brother, Kamal, is, uh, y- a great friend as well, uh, of mine, and seems very different, right? He seems almost the, the sort of yin to your yang. Wrote a great book called Love Yourself Like Your Life Depends On It. Where did your intensity come from? I mean, uh, w- have you always been that way? Why do you think you have that intensity, uh, which not to say Kamal lacks, but to a much lesser degree, of course.

    22. NR

      Yeah, it's a good question. I don't know. I mean, the, the, uh, genetics, uh, and evolution are a powerful thing. Uh, and you could just say at some base variation level both of us were hit with similar adversities in life, and, uh, our genes chose to respond very differently to see who would adapt their way out of the situation. Um, so at the core level we're, we are very different. Um, you know, we, we had a tough childhood growing up. Uh, make no secret of that. Uh, and we just responded in different ways. Um, for me, it was all about winning and having a strong desire to win. Uh, I started out as a bookworm, and then I had to transition into sort of being a, a combatant in the field of business, if you will. And now I'm sort of making my transition back into being a bookworm. Uh, [laughs] I, I think everyone gets shaped very, very early on in life. Um, you're probably baked in terms of your core personality by the time you're 12 or 13. Uh, you hit puberty. It's a jarring thing. You sort of emerge into the world. You become an adult. You construct your ego. You go out there to, to, to fight your fights, to do your things, to become who you wanna be. And then at some point, you get to where you are, where you wanted to be or close enough, and you start realizing, "Wait, it's not about external world. It's not about external accomplishment. I have to work on myself." Uh, and I think my brother Kamal has gotten to that point as well. Uh, and then you, you sort of start working on the, the inner being. So I'm not sure I answered your question about where it comes from, but, uh, you know, I, I think, uh, we all get shaped by adversity. Uh, every great thing that is, that I've ever done or accomplished, you know, according to external metrics, um, or even when I look internally, all the great things that have happened to be in my life that I consider highly positive, they all started with something highly negative.

    23. TF

      Hmm.

    24. NR

      Um-

    25. TF

      What made your childhood difficult? Or what were aspects of it that made it challenging?

    26. NR

      Uh, we were, we were immigrants. So we came to this country when I was nine. My brother was 11. Uh, we had very little. Uh, my mother raised us as a single mom in a studio apartment. Uh-

    27. TF

      Where did you come from?

    28. NR

      Uh, from India. And, uh, yeah, she, you know, she went to... She worked a menial job by day, and then she went to school at night. Uh, so we were latchkey kids and sort of left to, uh, develop and learn on our own. And a lot of growing up was watching the ideal American lifestyle but sort of from the other side of the window pane with my nose pressed against the glass and saying, "Yeah, I want that too, and I want that for, for myself and my kids." So I, I grew up with a very dark view of the world on the other side of the tracks, and then kinda had to cross over and, uh, start trying to fit into, you know, this Amer- amazing life that is available to most, but not all Amer- all Americans.

    29. TF

      And where did you... Which part of India did your mother come from or bring you from, and then where did you grow up in the US at that point?

    30. NR

      So we ca- yeah, we came from Delhi, which is the capital of India. And, uh, here we landed in, uh, Queens, New York. Uh, and, uh, we grew up in Queens Village and Jamaica, Kew Gardens. We moved around a lot. We probably lived in 9 or 10 different places in the course of nine years.

  5. 16:46 – 20:19

    Radical honesty as a value: physics, New York lessons, and being present

    1. NR

      Yeah. You know, the honesty thing is, is a core-

    2. TF

      [laughs]

    3. NR

      ... uh, foundational value, right?

    4. TF

      Yeah.

    5. NR

      Um, so to me-

    6. TF

      Now, in fairness, in fairness, I totally did. [laughs]

    7. NR

      Yeah. Well, I, I, and I think, like, uh, uh, f- so I have a couple of core foundational values, and they're not things that I explicitly developed. They're just sort of you can look back after the fact and say, "Oh yeah, I won't compromise on those things." But now I realize how important honesty is. Uh, and I, and I was-- And I learned that from a couple of different places. Uh, one is when I grew up, I wanted to be a physicist, and I idolized Richard Feynman. I read everything by him, technical and non-technical, that I would get my hands on. And he said, "You must never, ever fool yourself, and you are the easiest person to fool." So that was, that was, uh, the, the physics grounding was very important because physics you have to speak truth. Uh, you don't compromise. You don't, uh, negotiate with people. You don't try and make them feel better. Because if your equation is wrong, it just won't work, whatever you're doing. So I think the science background is important in that. Um, a second is growing up in New York, I grew up around some really rough and tumble kids, some of who were actually the Russian mob. Uh, and I once had an encounter where I watched one of them threaten to kill the other. Uh, and the w- the one who would, the would-be victim, uh, you know, went and hid, and then finally he let the aggressor into his house after the aggressor promised him, "No, I'm not gonna kill you."

    8. TF

      [laughs]

    9. NR

      Their, their honesty was such a strong virtue between them that even when they were ready to kill each other, they would take each other's word for things.

    10. TF

      Hmm.

    11. NR

      Uh, it, it, it sort of s- uh, uh, went above, above everything. And even though it was honesty in a mob context, I realized, like, how important that is in relationships. And then as I get older in life, I realized that a lot of happiness is just being present. And whether you get this out of Buddhism or cognitive therapy or, or drugs or wherever, you realize that to live in the present moment is the highest calling. It's, it's the source of all happiness. And when you're not honest With somebody else, uh, or when you even withhold something in your mind, what you've done is you've created a second thought process. You've created a second thread in your head that then has to stay active keeping track of what you've said versus what you're really thinking, and that takes you out of the moment, and it brings you unhappiness over time. You will not realize it at that moment itself, but it will create stress and distraction. So if you really want to be happy, you have to be present, and one of the core tenets of being present is to be completely honest at all times.

    12. TF

      There is a great short book that had a huge impact on me on this topic called Lying by Sam Harris, which was just-

    13. NR

      Mm-hmm

    14. TF

      ... phenomenal because it explored the impact not just of lying in the way that most people think of it, but gener-generalized deceit or even white lies that are intended to protect people. Um, the-- and just to come back to Feynman also, f-Feynman is a character and a thinker who I, I've long idolized in many ways. Surely You're Joking, Mr. Feynman! is one of my favorite books, and even for non-technical people, uh, I think he's someone worth exploring. And if y-if you're not the reading type, you could just search for a video, I think it was done on Nova ages ago, called The Joy of Finding Things Out, which is j- it gives you such a taste of Feynman and, and the way that he not only, I think, questioned the so-called obvious or best practices, but also, um, explored being a polymath, right? I mean, even though he was a worl-world-class physicist, he was also an amateur safecracker and, uh, pickup artist [chuckles] and musician, you know, in other ways. Uh, really fascinating guy. The-- You--

  6. 20:19 – 25:16

    From Venture Hacks to AngelList: building what founders need, and a future of individual work

    1. TF

      It seems like you have scratched your own itch in a lot of respects, right? With whether it was Venture Hacks, like you had a pain point, and you wanted to help other people understand what can be a very opaque black box, which is venture capital and so on. And so you provided these how-to, uh, articles and so on that you would have liked to have had, right? And it seems like AngelList. Does AngelList serve a similar function? I mean, how did AngelList come about?

    2. NR

      Yeah. So it's, it's exactly that, which is, uh, basically self-actualizing, uh, creating the product that you want. So the initial problem was, uh, entrepreneurs go out and raise money. It's complete black box. Nobody knows what to do. They do the most important negotiation of their life, which is the initial term sheet or initial deal with a venture capitalist, and they have no information. So they need that information. Boy, I wish I'd had that information, and that's where Venture Hacks came from. And then AngelList was, well, okay, that's how you negotiate a term sheet. How do I get a term sheet? How do I find investors in the first place? For that, we built a product. Uh, and then a few years into AngelList development, it became very clear the biggest problem in this environment is not how do I raise capital, it's how do I get help building my business? How do I find great, uh, individuals to help me, and how do I recruit great talent? Um, so we created both our syndicates product, where you, of course, are one of our top leaders who-

    3. TF

      Mm-hmm

    4. NR

      ... invest in companies. Uh, as well as we created our jobs product, which helps, uh, companies find great engineers. At the end of the day, we stand for founders, we stand for underdogs. And, you know, I-- it's funny, you asked me at the beginning, how do I describe what I do? I said, "I'm an entrepreneur." And in the back of my mind, what AngelList does is it helps founders find other founders, and on the recruiting side, it helps founders recruit and find other founders. Uh, and in fact, when I look inside AngelList itself, the company's only thirty people. Uh, almost everyone in the company is a former founder, um, or wants to be a future founder and is getting their training wheels on at AngelList and then is going to go start a great company. And we've had former engineers from us go and start companies like Instacart and Cover, um, and many more will come out of it. So at the end of the day, it-- to me, it's all about founders, it's all about individuals, it's all about the underdog. Uh, and I think long term, on a, on a long enough timescale, maybe it's fifty years from now, maybe it's five hundred years from now, but almost everybody on this planet will work for themselves. Uh, the information revolution is reversing the Industrial Revolution. What the industrial age did was it allowed human beings to team up in mechanistic, organized, hierarchical ways, um, to create factories and production. Uh, and I think the information revolution is breaking down the communication barriers. It's saying the optimal size of the firm is shrinking from thousands to hundreds to dozens, maybe even to one at some point. Uh, and eventually, every morning, someone will wake up, or every week you will wake up, and on your phone or whatever the device is of the future, um, you will get an alert with a various bunch of jobs and contracts that you can choose from. You'll look at them, you'll pick out which ones you like based on your social connections and how much they're offering you and how much it can build your profile and your future work, and you'll do that work, and then you'll be ranked on it, you'll be rated on it. Um, and then you'll-- if, if you want to take the next week off, you'll take the next week off. If you want to do two jobs at a time, you'll do two jobs at a time. But I think the future is all headed towards individual brands. You can see how, uh, reporters on The New York Times now, they're, they, they build individual brands on Twitter that far exceed the brand they would will-- that they would build just under The New York Times. Um, you yourself, I mean, you're an individual brand. There's, there is no-- there is nothing else other than Tim Ferriss. Tim Ferriss doesn't work for CNN. Tim Ferriss doesn't work for, uh, Apple, doesn't work for New York Times. You're an independent brand, and you're an independent actor, and I think the entire world is headed that way. And so to me, I was lucky enough to be a founder early, but I figured out how hard it is, what are the parts of it that work, the parts of it that don't. And so now what makes me happy is to work on a platform that creates more founders and helps those founders, because I think at the end of the day, we're all founders. We're all meant to work for ourselves. We're meant to be individuals. We're not meant to follow. We're not meant to be in hierarchies. We're not meant to go to nine-to-five jobs where we're told what to do over and over. And the sooner we get off the grid and self-actualize and become free, the better off all of humanity is.

    5. TF

      I, I mean, I think you, people could also look at being a founder as just being a creator, right? And I think there's the-

    6. NR

      Yes

    7. TF

      ... in my mind at least, the misconception that you f- you find yourself, uh, whereas I think that a more constructive way or actionable way of looking at it is creating yourself, right? Day by day, habit by habit, decision by decision. It's not some needle in a haystack that you have to, you know, go into the jungle and take drugs to find, although w- that's a separate conversation. [laughs] But, um, uh, the... Let's talk about founders for a second, uh, but in the, the startup context.

    8. NR

      Mm-hmm.

  7. 25:16 – 28:32

    What Naval looks for in founders: intelligence, energy, integrity—and people you actually like

    1. TF

      The, one of the more common questions that people ask successful VCs or investors is w- what do you look for in a founder? So I'm just gonna ask you that. Like, what-

    2. NR

      Mm-hmm

    3. TF

      ... what are the things that you look for in founders or the red flags that disqualify an investment or a founder?

    4. NR

      Yeah. So number one, intelligence. Um, you gotta be smart, which means you have to know what you're doing to some level, and that's a fuzzy thing, but, uh, you talk to people, and you kind of get a sense of, uh, do they know what they're doing or not? Do they have insight? Do they have specific knowledge? Have they thought about this problem deeply? It's not about the age. It's not how many years they've spent, but just how deep is their understanding, um, of what they're about to do. So intelligence is key. Uh, energy, because being a founder is brutally difficult. It takes a long time, and in the long run, the people who succeed are just the ones who persevere. So if someone runs out of energy or if they're doing this in some, uh, hesitating, preliminary way where they're looking for constant positive feedback, uh, or if they're easily thrown off course, then they're not gonna make it to the end, uh, especially in the highly competitive startup context. And then finally is integrity, uh, because if you have someone who's high intelligence and high energy but they're low integrity, what you've got is a hardworking, smart crook. [laughs]

    5. TF

      Yeah. [laughs]

    6. NR

      Uh, and, and especially in the startup world, things are very dynamic. They're very fast-moving. Uh, people are very independent, so if somebody wants to screw you over, they will find a way to do it. Um, and fundamentally, ethics and integrity are what you do despite the money. Uh, if being ethical was profitable, everybody would do it. So what you're looking for is a core sense of values, uh, that rises above and beyond the pure financial incentives. So for example, if I'm talking to a founder, and they offer to do something that is slightly unfair to another shareholder or employee or founder in exchange for making me happy, that's a red flag. Uh, s- because if they can do it to them, they can do it to me.

    7. TF

      For sure.

    8. NR

      Uh, a- and integrity is the hardest one to figure out because it requires longitudinal relationships. Um, and s-

    9. TF

      Meaning long term.

    10. NR

      Exactly. So I, I've just become more hyper-aware of that piece as time goes on. Uh, but those are kind of the three things that I look for. And then I would just say orthog- you know, a thing that isn't really about success, but it's more just about personal time, is when you invest in s- somebody or you work with somebody, you start a company with somebody, you're signing up to spend the next decade of your life having them in your life.

    11. TF

      Right.

    12. NR

      Uh, and so you just have to make sure you actually genuinely like these people. You don't consider work to have to answer a phone call or take a meeting or spend time with them. If it's exhausting, if they're downers, if they're negative, if they're difficult, no amount of money is worth it. Uh, you know, you and I will both die with money in the bank, and so i- it's not about money at this point. It's about, uh, do I wanna spend my scarce time, resources, mental energy, spirit, uh, interacting with these people? Uh, my favorite founders are actually the ones who I learn from. So every time they call me up 'cause they need help with something, I jump on it because I know that walking around the block with them for an hour, I'm gonna walk out much smarter.

    13. TF

      Who are some that come to mind just offhand? Uh, y- re- recognizing that there are many others you could name.

  8. 28:32 – 36:58

    Founder examples and “being right when everyone else is wrong”—plus common VC myths

    1. NR

      Oh, there, there are tons, but just to give you a very recent example, there are these, uh, two basically kids, uh, Corey and Michael, who started this company called One, which now runs a product called After School. Uh, and they're young. I think Corey was 19 when they started the com- he might've been 17.

    2. TF

      How do you spell One?

    3. NR

      Mi... Uh, just O-N-E.

    4. TF

      One.

    5. NR

      That was the name of the c- that was the name of the company, but they have different products. And, uh, Michael Callahan is his co-founder. Um, and these guys are just brilliant. They're, they're young. They're kids, but the level at which they think about, the depth to wh- that they put into social products is absolutely mind-blowing. Uh, another one is Ryan Breslow. I recently invested in his company. He started a company called Bolt, uh, which does stuff in the financial payment space. Uh, you know, this founder has assembled a crack team of engineers out of Square and Twitter and Stripe, and he's, he's done very little so far. He's a very young guy. Um, and then when I asked to invest in his company or I was getting to know him, he reference checked the heck out of me, you know, at every, every step of the way.

    6. TF

      [laughs]

    7. NR

      Very professional, very quick, very thorough, uh, but he did more diligence on me than I did on him. [laughs] Uh-

    8. TF

      How did he, how did he do that without being a pain in the ass to people you know? 'Cause I know people, for instance, they're entrepreneurs I shall not name, who-

    9. NR

      Yeah

    10. TF

      ... try to pitch me, and they have, like, 30 people. They just bombard 30 of my friends-

    11. NR

      Mm-hmm

    12. TF

      ... to try to get to me, and it's a complete turnoff if they're just using-

    13. NR

      Yeah

    14. TF

      ... kind of brute force. How did he do it the right way?

    15. NR

      It wasn't brute force. He asked me for references. He also did his own back channel. He was very quick. He was very transparent. Uh, and then he actually compiled the feedback he had gotten on me and gave it to me-

    16. TF

      Oh, wow

    17. NR

      ... as if he, as if he had done a peer review of me-

    18. TF

      [laughs]

    19. NR

      ... and he thought I should have the data.

    20. TF

      [laughs]

    21. NR

      And I was so blown away by his professionalism, uh, especially for such a young person. He's just probably one or two years out of school.

    22. TF

      That's amazing.

    23. NR

      Maybe a little bit more. Uh, so, uh, it's just certain people, uh, certain entrepreneurs, you get the feeling they really care about what they're putting together. Uh, every early move that they make, they consider it as they're putting bricks in the foundation of a skyscraper that they're gonna build, and you can see that right away. A founder who comes barreling in decides very quickly, uh, you know, treats it like a flip, says, "Well, you know, if I get a good offer, I'll sell this thing," or, "I'll do whatever's pragmatic to make money," those founders are not in it for the long haul. And you learn very quickly that all the returns in this business are made with a huge, huge outcomes, at least for an investor. And so you start becoming hypersensitive to these founders who actually apply care and are very meticulous about how they go about things.

    24. TF

      Yeah, I haven't had... And granted, you've been in. I mean, how many, how many individual and fund-based investments have you made to date, would you say, if you had to guess?

    25. NR

      I lost track. It's probably north of 150.

    26. TF

      Yeah. You have a lot more experience than I do, of course, but I haven't had, I don't think, a single good outcome from any company led by a founder who was like, "Well, if the wind blows this way, then this. If the wind blows that way, then that." They've always had a very clear vision of some type or some type of true north. Um, and, and-

    27. NR

      That's right

    28. TF

      Yeah.

    29. NR

      Yeah. In this industry, you get paid for being right when everybody else is wrong [laughs] . Uh, so unfortunately, that means a lot of them run full speed and crash into a wall, uh, which is painful, but they'll get up and they'll run again at somebody, at, at something else. Uh, but you get paid for being right when everybody else is wrong. So if you're looking for, uh, how to operate based on what everybody else around you thinks, uh, then, you know, you're, you d- you're, you probably don't have what it takes. That said, these people are also very hard to separate from delusional crazy people [laughs] .

    30. TF

      [laughs] Right. Right. I mean-

  9. 36:58 – 40:52

    Internal state and decision-making: emotions, bias control, and learning from stoicism and “rational Buddhists”

    1. TF

      Uh, what, uh, what books or people outside of the startup world have most Uh, improved your ability to invest, um, and maybe, maybe broadly speaking, just res- resource allocate

    2. NR

      Yeah. So that's a really good question, and so this is a very deep question that's gonna have lots of answers. But at the end of the day, I think you have to work on your internal state, uh, until you are free of as many biases and, and conditioned responses as you can be, and it will improve every aspect of your life, including investing. Uh, and I am a bookworm, so I read an enormous amount. Uh, I mean, like I was raised essentially in a library as a daycare center. And so, uh, I've just read so much that I don't [chuckles] even know where to start. But if you work on your internal state, one of the things you start realizing is, as an investor, uh, emotions dominate. Investors are very emotional, even though we act or we pretend to be very rational. For example, you'll decide in the first five minutes of a meeting usually whether you wanna invest in a company or not. And if a company doesn't take your money in the first round, you get annoyed with them or you feel like they crossed you, then you have to undo that emotional state so when the second round comes along, you can still be a positive force and continue helping the company and maybe have a bite at the apple a second time. Uh, and these kinds of skills are extremely hard to build. They're not things you're gonna build by, by reading one book, and then you're like, "Aha." So I don't believe in the epiphany theory of self-development, uh, where you read some book, you have an incredible epi- epiphany. You read one phrase, you're like, "Okay, that's great. This changes my life," and then you scrawl it down on a piece of paper, and you keep looking at it, or you put it as a backdrop to your computer screen. Life doesn't work that way. Um, what you kinda have to do is you have to build skills. Uh, and I think happiness is a skill, nutrition is a skill, diet is a skill, investing is a skill, self-awareness is a skill. And skills get built up over decades with feedback loops, and you just have to constantly keep working at it on it. So the books that have helped me a lot, I, I think there's a class of books that I would kind of put in the stoicism category, uh, and I know you've been a big advocate of these in the past, and I sort of discovered them, uh, independently, but they were very influential. So s- uh, you know, Seneca and Marcus Aurelius, uh, both stand out. Meditations by Marcus Aurelius was absolutely life-changing for me because it's, it's the personal diary of the Emperor of Rome, and here's a guy who was probably the most powerful human being on Earth the time where, that he lived, and he was writing his own diary to himself, not expecting it to be published. Uh, and when you open this book, you realize he had all the same issues and all the same mental struggles, and he was trying to be a better person. And so right there, you figure out, okay, uh, success and power don't improve your internal state. You still have to work on that. Uh, and so that, that, that class of books is very influential. Um, I, I, I, I like to pay attention to what I consider the rational Buddhists, uh, because a lot of Buddhism is drowned in mysticism and Hinduism and sort of, uh, worship this guru or do this ritual. It's like I don't pay any attention to that. Um, but I pay a lot of attention to what I consider rational Buddhists, where they can make the case very intelligently with reasoning along the way as to how you should train your mind to work or how you should observe your mind. Sam Harris, who you mentioned earlier, is great. Uh, Jiddu Krishnamurti, who's a lesser well-known guy, but, uh, an In- an Indian philosopher who lived turn of the last century, um, is extremely influential to me. He's an uncompromising, uh, very direct, uh, person who basically tells you to look at your own mind at all times. Uh, and so I have been hugely influenced by him. Probably the best book of his, uh, that I like is the one called The Book of Life, which is sort of excerpts from his various speeches and books, uh, that are stitched together. Um, oddly enough, Bruce Lee wrote some great philosophy.

    3. TF

      Definitely.

  10. 40:52 – 51:42

    How Naval reads: quitting the “finish every book” rule, and standout blogs and writing lessons

    1. NR

      Uh, and, uh, Striking Thoughts is a book that is a good summary of some of his philosophy. Um, but I could go on and on and on. I mean, there are... You have to read hundreds of these things, literally. Blogs. The blogs are, I, I feel, an underappreciated resource. Uh, we're now in a day and age of Twitter and Facebook. We're getting sort of bite-sized, pithy wisdom that's really hard to absorb. Uh, and books are very difficult to read as a, as a modern person because we've been trained, uh, well, we've got two contradictory pieces of training. One is our attention span has gone through the floor because we're hit with so much information all the time that we wanna skip, summarize, skip. We wanna get to the TLDR, cut to the chase, too long, didn't read. Uh, you know, what's the 140 character version? What's the Instagram version? On the other hand, we're also taught from a young age that books are something you finish. Books are something that are sacred, that you treat books as a... You know, when you go to school, and you're assigned to read a book, you have to finish the book. So over time, we learn, uh, we forget how to read books, or we get in this contradiction where everyone I know is stuck on some book. Everyone is stuck on some book.

    2. TF

      [laughs]

    3. NR

      I'm, I'm sure you're stuck on some book right now. It's like page 332. You can't go on any further, but you know you should finish the book. So what do you do? You give up reading books for a while. Your Kindle or your iPad or whatever you use, or even your paper book is in a stuck state. And, uh, that for me was a tragedy because I, I grew up on books, and then I switched to blogs, and then I switched to Twitter and Facebook, and then I realized I wasn't actually learning anything. I was just taking in little dopamine snacks all day long. [laughs]

    4. TF

      [laughs]

    5. NR

      Uh, I was getting my little 140 character burst of dopamine, and then I'd retweet, and then I'd see who retweeted my tweet. Then I'd get into an argument on Twitter. And, you know, it's a fun, wonderful thing, but it's a game that I was playing. I wasn't actually learning anything. So-

    6. TF

      Usually with, uh, Startup L Jackson is, uh [laughs]

    7. NR

      Yeah, Startup was a great character on Twitter. Uh, so I- I, I realized, like, I have to go back to reading books because when you're talking about solving old problems, the older the problem, the older the solution. So if you're trying to learn how to drive a car or fly a plane, uh, absolutely you should read something written in the modern age because this problem was created in the modern age, the solution was created in the modern age. But if you're talking about an old problem like how to, you know, generally keep your body healthy, how to stay calm and peaceful of mind, uh, what kinds of value systems are good, um, how should you raise a family, these kinds of things, uh, the older solutions are probably better, and they withstood the test of time. Any book that survived for 2,000 years has been filtered through a lot of people. Now, it may have some stuff in it that we now know to be true, but the general principles are more likely to be correct. Um, so if I wanna learn the theory of evolution, which I kind of use as my binding principle whenever I'm trying to explain any human action, uh, people read all kinds of blog posts and tweets on evolution. Everyone has a loose understanding how, of how evolution works, but how many have actually read The Origin of Species? I mean, you can get it for five bucks on Kindle, and it's a very easy read. It's not a difficult read. Um, and you can read the actual source, and you can see the source of the brilliance, and you can see how Darwin came up with stuff back then that we're still trying to figure out or statements he made that we're still trying to prove out. But there's very little that's incorrect in that book, and it is a, a source book. So I wanted to get back into reading these source books. Um, and I knew it was a very hard problem 'cause my brain had now been trained to spend time on Facebook and Twitter and, and these other bite-sized pieces. So what I did was I came up with this hack where I started treating books as throwaway blog posts or as bite-sized tweets or Facebook posts, and I felt no obligation to finish any book. So now anytime someone mentions a book to me, I buy it. At any given time, I'm reading somewhere between 10 and 20 books. I'm flipping through them. So I'll f- I'll ski-- If the book is getting a little boring, I'll skip ahead. Sometimes I'll start reading a book in the middle because some paragraph caught my eye, and I'll just continue from there. And I feel no obligation whatsoever to finish the book. If at some point I decide the book is boring or if it's got, uh, pieces of it that are incorrect so now I can't trust the rest of the information in there, I just delete it, and I don't remember them at all. So I treat books now as other people might treat throwaway light pieces of information on the web, and all of a sudden, books are back into my reading library.

    8. TF

      Right.

    9. NR

      And that's great because there's a lot of ancient wisdom in there.

    10. TF

      And y- you, you mentioned blogs being potentially a source of good information. If-- Are there two or three blogs that you have particularly liked or do particularly like that you could recommend to people?

    11. NR

      Yeah. So blogs are great because now all of a sudden you have some incredibly smart people who before may have had niche audiences or may not have, you know, their full-time job is not to be a writer. Um, so they, they can, they have a voice now. And the reality is books are long because that's the size you need to justify printing up a, you know, cutting up a tree and printing a physical object and sending it to a bookshelf, when reality a lot, uh, a lot of the wisdom in these books is can be encapsulated in a few pages. Uh, but you can't charge somebody $20 retail for a couple of pages of info. So I, I feel like blogs are actually a very efficient source of information, uh, and there are some absolutely brilliant people out there that, that you should take advantage of. Now, the problem is if you read enough information on the internet or in books, it all cancels to zero. [laughs] And you're, and you're probably, you have a lot more facts, but you don't have much more wisdom. So you do have to be careful what sources you, you get information from. So one of the criteria I use if, if somebody is a deep expert and they're talking about things, but then they start making, uh, errors in rationality or judgment or clear biases start showing through, then I basically put that blog or I put that book down because now I can't trust what they're saying. Um-

    12. TF

      You put it on probation, probationary period?

    13. NR

      E- essentially because you have to f- you have to filter the information that comes at you. For example, you could read news articles all day long, and all that would end up happening is you would end up a hyper-stressed, anxious individual, and you wouldn't even know why. At some core level, your brain would have been rewired to assume that every bad thing that's happening is happening next door instead of tens of thousands of miles away. Um, so I filter my blogs very carefully. I have a long reading list that I use of, uh, couple of hundred blogs. But like a recent standout is a blog called Melting Asphalt. Um, it's, uh, written by a guy named Kevin Simler out of New York. I've never met him, uh, but I read his blog, and it was mind-blowing. He just really digs deep into all these topics, uh, that we take for granted. He, he figures out an orthogonal viewpoint on it. He makes some nice observations. But very often he'll end with questions or no conclusions. He'll just sort of meander off. And to me that-

    14. TF

      What types of topics does he explore?

    15. NR

      He'll talk about like how the brain works, how human cognition works. Uh, he'll go into topics like why do we dance, uh, you know, basic economics theory leading to bad outcomes. I, I just highly recommend reading it for anyone who's intellectually and scientifically curious. Um, and what I like about it is that a lot of times he, he doesn't feel the need to wrap up with a conclusion.

    16. TF

      Right.

    17. NR

      It's very clear that he's exploring the space and learning. Um, like for example, you know, your, your blog is great for what I consider sort of these quick one-off hacks.

    18. TF

      Mm-hmm.

    19. NR

      Or you're, you're great at surprise, the twist, right? Tim's gonna tell you how to, uh, you know, how to peel a hard-boiled egg like instantly.

    20. TF

      [laughs]

    21. NR

      Uh, by the way, I blew up one on my kitchen counter. I had yolk everywhere. [laughs]

    22. TF

      Yeah, yeah. Sometimes it-

    23. NR

      It turns... Yeah.

    24. TF

      If it's soft, soft boiled, not a good idea. [laughs]

    25. NR

      That was-- Yes, that was my learning there. Um, so, you know, everyone has their style. Uh, but your style is very much you have to have a conclusion. Uh, I have not seen a Tim Ferriss blog post that does not lead to an ac- actionable conclusion because you've built your brand around being a, a fast learner lifestyle hacker. I feel like if I go into Tim's blog, the promise that I get is I can get 98% of the benefit by doing 2% of the work, which is very seductive. Um, whereas on, on Melting Asphalt, what I know is gonna happen, I'm gonna have this massive exploration of a deeply interesting and complicate-- complex topic, uh, with a couple of different hypotheses and no real conclusions.

    26. TF

      Yeah.

    27. NR

      Um-

    28. TF

      Which is, which I think is important for people to balance out with the prescriptive, uh, b- Sort of Scooby Snacks of how-to solutions. I think it's important for people to be able to sit with uncertainty. I mean, I think that's why Richard Feynman's so interesting also to ... I mean, training yourself to be a, a good scientist does not require college degree or a PhD. It requires, like you said, not fooling yourself and having good questions. And sometimes you just have to sit with those questions and evaluate whether they're the right questions or the wrong questions, or if there's a better tweak to that question. So it sounds like The Melting Asphalt author, uh, is kind of, uh, along the same lines of a Freakonomics, but without necessarily the conclusions.

    29. NR

      Yes. And in that sense, I actually even like it better than Freakonomics. The original Freakonomics is fantastic, don't get me wrong, but now they just have to fill a lot more volume, so of course the quality goes down. Um, but it's still a ... Freakonomics is still great. Another one is, uh, you introduced me to this guy. He's a childhood hero of mine growing up, uh, Scott Adams.

    30. TF

      Yeah.

  11. 51:42 – 1:00:57

    Big wins, big misses, and the real regret: time—especially advisory roles

    1. TF

      Doesn't mean your answers have to be rapid fire, but I'll just throw out a couple to add some color and sort of connective tissue to what we're talking about. What are some of your biggest successes in the investing world? Just the sort of greatest hits of, of Naval.

    2. NR

      Yeah. So I've thrown a lot of darts. [laughs]

    3. TF

      [laughs]

    4. NR

      And, uh, you know, half of it is just showing up, frankly.

    5. TF

      Yeah.

    6. NR

      Uh, if you're in a tech business, the best thing you can do for yourself is move to Silicon Valley. Just like if you're in acting, you probably have to go to Hollywood. And if you're in finance, you used to have to go to New York, although now there are more options. Uh, so I, I don't necessarily take credit for it in the same way that some people might say where they were very thoughtful and did a lot of diligence. Uh, you know, some of it was luck. A lot of it was luck. Um, but I was in, uh, the first round, uh, investor in, uh, Twitter, um, when it was first getting started. Uh, I was the first round investor in Uber when it was getting started. Uh, Thumbtack, uh, uh, Wanelo, Flipagram. Uh, there's a couple of others. Um, I was, uh, early in Postmates. I was actually probably the first real investor in there, um, after they got out of an incubator. Um, there's a bunch of them that goes on and on. It's hard for me to draw the full, the full list, but the fund that I ran is on track to return, uh, 10 or 20 times the capital that it had raised. Um, and my individual portfolio is up by, you know, dozens of times.

    7. TF

      Congratulations-

    8. NR

      Thank you

    9. TF

      ... once again. What about the-

    10. NR

      Dumb luck, dumb luck. [laughs]

    11. TF

      Well, well let's talk about dumb luck on the flip side. So what are some of the biggest misses, like deals you've passed on? Your anti-portfolio. I think it's ... Is it Sequoia that has that or Accel?

    12. NR

      Yeah.

    13. TF

      The antiport- [laughs]

    14. NR

      I think, I think Bessemer pioneered it, but it's a-

    15. TF

      Okay, got it

    16. NR

      ... it's a, it's a, it's a nice thing to do, which is to keep yourself intellectually honest. Um, Warren Buffett also pioneered it in a sense in that, uh, he goes on record at the annual meetings, uh, and talks about their biggest mistakes from the previous year. And then he'll literally look at the previous annual meeting what he talked about, and he'll go through it and he'll talk about what he said that was wrong. Uh, so to some extent he does these annual meetings just to keep himself intellectually honest. Um, and in terms of biggest mistakes, I passed on Twilio very early on, and Jeff Lawson, the founder, is a great founder, and he gave me every chance to invest. Uh, I passed on Pinterest. Uh, [laughs] Ben Silbermann gave me every chance to invest. I was sitting in bed next to my, at the time, fiancée, and-

    17. TF

      I thought you were gonna say next to bed. I was like next to bed?

    18. NR

      No, no. [laughs]

    19. TF

      I was like, wow.

    20. NR

      Yeah, exactly. We were that close.

    21. TF

      [laughs]

    22. NR

      Sorry, Ben. No, no insinuation implied. Uh, nothing implied. Uh, I was sitting in bed next to my fiancée, and, uh, Ben had just ... We'd helped him a little bit with AngelList, although not a lot. We were just getting started. And he was raising money for Pinterest, and I saw the numbers go up month to month to month, and I had a chance to invest the first time, the second time, third time. And he kept offering it to me, and I was sitting in bed next to my fiancée, and she was obsessively using Pinterest.

    23. TF

      [laughs]

    24. NR

      And she said, "I think you should do this." And I was like, "Ah, I don't get it. You know, it's images. It's, like, flickery. Who's gonna use this? How is this gonna make money?" And so I passed on that. Um, but you know, I've got lots of stupid ones like that. I could've been an advisor to YouTube in the early days. I helped them out, but I didn't take any stock, uh, even though they were kind enough to offer it. Um, you know, there's lots and lots of misses. Uh, Square I could've done the first round. I just thought it was too expensive. Even Twitter where I did my piece, I did a much smaller piece than I was allocated just 'cause I thought it was too expensive. [laughs] So-

    25. TF

      Yeah, I did, I did the same thing in like 2009. I was like, "This is never gonna work out, but whatever."

    26. NR

      [laughs]

    27. TF

      Put some money in. The, uh- The, uh, rule, you mentioned Warren Buffett. So Warren Buffett often talks about, you know, the, the two rules of investing. Rule number one, don't lose money. Rule number two, pay attention to rule number one, or something along those lines. When you've made investments, um, that in retrospect you look back on and you're like, "I knew it. I shouldn't have done that deal," what are the things that lead to you making those bad investments or overriding your rules or intuition?

    28. NR

      Yeah. I, I don't actually dwell on the bad investments much because in the startup business is j- uh, the exact opposite of Warren Buffett's value investing business. He's investing at a much later stage where you have a lot more data and you're putting much bigger amounts to, uh, uh, in there and, and you're betting that you're gonna make a compounded return of 17, 20, 30% a year. Uh, in the startup world, you're betting that 90% of these companies will go to zero or just return your money, and then the remaining 10% are gonna post huge multiples and markups. So the Twitter investment is probably now up 400X. Uh, Uber is probably up around 4,000X. Uh, so then the, the returns to the winners can be staggering and can overwhelm the losses in the portfolio. So you always focus on the upside. You don't really pay attention that much to the downside.

    29. TF

      Yeah.

    30. NR

      Uh, and I would say most of my downside mistakes that I think about are mistakes of omission, not mistakes of commission.

  12. 1:00:57 – 1:07:05

    Meditation that fits real life: choiceless awareness, fear-based thoughts, and waking up from “dreaming”

    1. TF

      Do you have a current meditative practice?

    2. NR

      I have a couple. Uh, like most people, I talk about doing it, but don't really do it all that well.

    3. TF

      [laughs]

    4. NR

      [laughs] I think med- meditation is like, uh- You know, like a dieting or where everyone is supposed to be following a regimen. Everyone says they do it, but nobody actually does it. Uh, the real set of people who meditate on a regular basis I found are pretty rare. Um, and I've identified and tried at least four different forms of meditation. Uh, the one that I found that works the best for me is, uh, something called choiceless awareness or non-judgmental awareness.

    5. TF

      Right.

    6. NR

      Where you essentially don't sit in a corner and don't stay quiet. You walk around. Um, you're going about your daily business. Uh, but hopefully there's some nature around. You're not talking to somebody else. And what you practice is you just learn to accept that moment that you're in without making judgments. You don't say, "Oh, there's a homeless guy over there. I better cross the street." You don't say... You don't look at two people running by and say, "Oh, he's, he's out of shape," or, "I'm in better shape than him," or, "That person's better than me," or, "This one's better," or, or, "I should go get a coffee," or whatever. You just don't make any decisions. You don't judge anything. You just accept everything. And, uh, if you do that, I find if I can do that even for 10 or 15 minutes walking around, I end up in a very peaceful, grateful state. Uh, and so that one works well for me.

    7. TF

      And when, when those thoughts come up, right? When you see the guy with the bad hairdo and you're like, "That guy has no, no business having that unmanageable hairdo," or whatever ridiculous thought comes to mind-

    8. NR

      Right

    9. TF

      ... what is the internal response to that?

    10. NR

      What I do is, uh, I, for those of you who have programmed, uh, I'm basically trying to run my brain in debugger mode. Uh, I'm trying to be very, very alert and watch my thoughts. You're not trying to judge anything, including your own thoughts. And, uh, you know, there's a great definition that I read that says, "Enlightenment is a space between your thoughts." Uh, which means that enlightenment isn't this thing you achieve after 30 years sitting in a corner on a mountaintop. It's something you can achieve moment to moment, and you can be certain percentage enlightened every single day. So you wanna create as much space between your thoughts as possible, and the way you do that is by being aware of what your thoughts are and why you're having them. So if I saw the guy with the bad hairdo or the toupee, um, I would look at that and I would... At first I'd be like, "Ha ha, he has a bad hairdo." And then I'd say, "Well, why am I laughing at him? Oh, to make me feel better about myself. And why am I trying to make me feel better about my own hairdo? Oh, 'cause I'm losing my hair, and I'm afraid it's gonna go away." And what I find is that 90% of thoughts that I have are fear. 90% are fear-based. The other 10% are probably desire-based, and as any, um-

    11. TF

      That's a very tactful way to put it. [laughs]

    12. NR

      Yeah. And as any, as any Buddhist will tell you, that desire is just fear by another name. It's the other coin.

    13. TF

      Oh. [laughs]

    14. NR

      The other side of the coin is fear.

    15. TF

      I thought... Oh, I thought you were talking about something else entirely.

    16. NR

      Ah. [laughs]

    17. TF

      The, uh-

    18. NR

      No, for lust

    19. TF

      ... there's this-

    20. NR

      Lust? Yeah. [laughs]

    21. TF

      There's this, there's this cartoon. I don't know if you know who Harry Crumb is. He has all of these very sort of profane comic strips and was very famous, and there's a great documentary about him as well. I... Wait, Harry Crumb, I think that's actually a comedy. Uh, but, uh-

    22. NR

      Mm-hmm

    23. TF

      ... R. Crumb. Maybe I'm, I'm mixing it up. In any case, somebody can correct me in the comments. But-

    24. NR

      Yeah

    25. TF

      ... there's this one cartoon of his. I think it's a single cell, kinda like The Far Side in its format.

    26. NR

      Yep.

    27. TF

      And it's, uh, it's basically a drawing of people on the street in Manhattan, and every man has a thought bubble above his head with a vagina in it.

    28. NR

      [laughs]

    29. TF

      And every woman has a thought bubble above her head with a penis in it. [laughs] And there's everybody walking. Which, uh-

    30. NR

      Well, it is, it, that- that's why the Adam and Eve story is there, right? Original sin is lust. Uh, it's a thing that makes you fall out of heaven. Uh, the same way, at a... Maybe some of your readers have this, read this book called Siddhartha, but it's a beautiful parallel story to the making of The Buddha by Hermann Hesse. It's a great book. I highly recommend it. But even in that book, our, our protagonist is out there seeking enlightenment and gets really close, and the thing that drops him out of it is lust. He, he meets a woman that he falls in a, he feels lustful towards, and that sort of slowly becomes his undoing into everything. Um, but anyway, so to, to answer your original question, when I'm, when I'm doing the choiceless awareness form of meditation, which by the way isn't, as far as I can tell, it's not taught in any school. Um, it's something that I discovered mostly by reading enough of Krishnamurti's book and piecing together what he meant, 'cause he's a very, uh, he's not a, he's not a very clear speaker at times. Or he is clear, but in a very different kind of way. Um, and then I realized that, okay, so the point of meditation is to clear your mind, and the way to clear your mind is, yes, you can sit in the corner and struggle with it, which doesn't really get you the outcome, or you can do transcendental meditation, which is where you're using this chanting to create a white noise in your head to bury your thoughts. Or you can just very keenly and very alertly be aware of your thoughts as they happen. And as you watch them, you realize how many of them are just fear-based. And the moment you recognize it as fear, without even trying, it sort of goes away. And then after a while, your mind quietens. And when your mind quietens, you stop taking everything around you for granted. You start noticing the details of, oh my God, I live in such a beautiful place. It's so great that I have clothes on me. Uh, yeah, I can go into a Starbucks and get a coffee anytime I want. How rich am I? Uh, look at these people. They're, you know, each one has a perfectly valid and complete life of their own in their own heads that's going on. Um, so it sort of drops us, uh, it pops us out of the story, the dream that we're always in, the story that we're constantly telling ourselves. And if you stop talking to yourself for even 10 minutes, or if you stop obsessing over your own story for even 10 minutes, you'll realize that we are really far up Maslow's hierarchy of needs, and that life is pretty good.

  13. 1:07:05 – 2:04:00

    Habits and health: daily routines, the $50 teppanyaki grill, dropping caffeine/alcohol, and morning design

    1. TF

      The, uh... What is a bad habit that you're working to overcome right now?

    2. NR

      Very good question. So I, so this is something that I learned through our Polish trainer friend, Victor. [laughs] Currently Victor. Uh- Habits are everything. Everything. Uh, I think that we are, we are trained in habits fr- from when we are children, uh, including potty training and, uh, when to cry and when not to, and how to smile and when not to, and all of these things become habits. These are all behaviors that we learn and that we then integrate into ourselves. And then what ends up happening when we're older is that we're a collection of thousands, maybe tens of thousands of habit loops that are constantly running, uh, subconsciously, and they're internalized, and then we have a little bit of extra brain power in our neocortex for solving new problems. And so you become your habits. And one of ... And, and what really brought this to light for me is our, our friend, uh, our trainer gave me a routine to do every single day, and before that I had never worked out every single day. Um, and it's a light workout. It's not tough on your body. But I did this workout every single day, and I realized just the incredible, astonishing transformation that it had upon me, uh, both physically and mentally, because I think to have peace of mind, you have to have peace of body first. Uh, so that taught me the power of habits, and after that I started realizing that it's all about habits. So at any given time now, uh, within a six-month period, I'm either trying to pick up a good habit or I'm discarding a previously bad habit. And it takes time. So for example, if someone says, "I wanna be fit, I wanna be healthy, but right now I'm out of shape and I'm fat," well, nothing is gonna work for you in three months that's gonna be sustainable. It's going to be a 10-year journey at least. And in the 10-year journey, what you're gonna do is every six months or every three months, depending on how, how fast you can do it, you're gonna break bad habits and you're gonna replace them or you're gonna pick up good habits. So I think it is all about habits. There is nothing else. Um-

    3. TF

      So I was just gonna add some color to what you said. For those people who are curious, the, the morning routine is it's basically a mobility movement practice. It's not intended to give you a big burn or anything like that, and you're basically taking your joints to the end range of movement. And I think what's very unique about it also, and this is, uh, ties into the Laird Hamilton pool training and so on that was in a previous episode, is that you are ... You're, you're controlling your breathing in a very particular way and holding your breath at certain moments, and I think that has a lot to do with the kinda present state value of that routine. But, uh, you know, I could be ... I c- That, that's just one man's opinion. I ... Furthermore, I'd like to just add, and since you're always so, uh, forthcoming in a valuable way with, with, uh, pushing back, I'm gonna push back a little bit or maybe just revise-

    4. NR

      Mm-hmm

    5. TF

      ... from my mind what you said about the three months versus 10 years. So if you're, if you're fat, you can make a tremendous ... I, I think that people underestimate what can be done in a short period of time, and they, but they underestimate how quickly they can fall back into bad habits.

    6. NR

      Yes. Yes.

    7. TF

      Does that make sense?

    8. NR

      I, that's absolutely right.

    9. TF

      Yeah. So it's a long-term project, uh, because it's not a diet. It's a way of eating, for instance, that's required to keep you from not being fat in the future, right? But you can lose, say, 20 pounds in a month and do it surprisingly easily. But like you said, you have to sort of keep track of those habits, and I think measurement is a really great way to concretize. That's probably not a word. Make concrete, that was a little Don King, the- these types of changes. Uh, The Power of Habit by Duhigg is actually a very good, uh, book on this type of thing as well.

    10. NR

      Yeah. So basically, like examples of habits I've picked up in the last 12 months or I'm still working on, uh, and, and I, I don't ... I'm, I'm kind of, uh, I'm one of these people who wants everything, [laughs] right? So I don't wanna give up anything. So for example, if I want to stop eating bad foods, if I wanna lose weight by fixing my diet, uh, I don't go around, I, I don't say, "These foods are bad. I'm not gonna eat them," and then suffer, and then feel like I'm not eating tasty food. Instead, what I do is I do some combination of changing my taste buds to actually like the foods that are healthier for me, and substituting unhealthy tasty foods with healthy tasty foods, um, so that I can sustain it forever. I'm not interested in anything that is unsustainable or even hard to sustain. I want my life to be effortless. So once I've created a good habit, it has to be the kind of habit that I can sustain with no effort. The classic example for most people who have successfully lost weight in the last decade is most of them, not all, but most of them have been on some variation of a low sugar diet, uh, or a paleo diet or s- or something where they're just... Or a slow carb diet where they're just watching the simple carbs. And if you stay on one of those diets for a little while, what you realize is you lose your sweet tooth. And when you s- when you drink like a sugary drink, it's an overwhelming amount of sugar. It just doesn't taste good. Um, so I think there are, there are ways to fix your habits and do it in a very sustainable, gentle way.

    11. TF

      Mm-hmm.

    12. NR

      Um, so most recently I've star- I've, I've developed a lot more Japanese tastes in eating, uh, which has helped me a lot because now the food that I find tasty and flavorful is actually not sauced, not curried, not cream, not carb. Uh, and I find that kind of food sloppy. I find it hard to even look at.

    13. TF

      So-

    14. NR

      Uh

    15. TF

      ... so l- this ties into, uh, not to interrupt, but I was going to ask you, and I suspect this is related, what the, what $100 or less purchase has most positively impacted your life in the last six months. [laughs] And, um, I think this might tie in. Um-

    16. NR

      Yeah, yeah.

    17. TF

      Yeah.

    18. NR

      It's, it's a teppanyaki grill. It's like a little tabletop grill. And what I learned was that for food, the freshness and quality of the food going straight from the grill to your mouth is way more important than what you do with it. For example, in most recipes, in most restaurants, we sauce the heck out of everything, and we cream it, and we overprepare it, and we overprocess it because it's sitting under a heat lamp for 10 minutes. And by the time it gets from the cook to your plate to your mouth, 15 minutes have passed, and that's an eternity when it comes to food. Whereas the Japanese teppanyaki style of cooking is you have a tabletop grill, and you have high quality meats and vegetables, and you slice them thin, and you put them on top, and they're cooked a minute later, and then it goes straight from the grill to your mouth within 5 or 10 seconds. And literally all it needs is salt, and maybe not even that. And you can cook the vegetables in the oils from the meat. Uh, and it's the best tasting meal that I can imagine. I ... When I eat out now, I feel like I'm making a sacrifice on taste. So my meals at home taste better, and they're very simple to prepare. And the, really the hack is straight from the grill to your mouth because we're evolved as humans to eat cooking around the fire.

    19. TF

      [laughs]

    20. NR

      We're not evolved, uh, this is back to my evolution as a binding theory, we're not used to somebody going off and cooking the food and then coming to us 10 or 15 minutes later with the meat that's got cold on a plate. But now to make it taste good, they've put in all kinds of sauces on top. Um, so that, that is an example of a hack, and that $50 grill that I bought is the best investment for my health that I've ever made. The next best-

    21. TF

      Do you, do you know the brand offhand?

    22. NR

      I think it's a Presto tabletop grill.

    23. TF

      Yeah. Yep

    24. NR

      You know, it's not, it's not perfect 'cause it's got the non-stick surface on it, and I would rather not deal with whatever chemicals are coming out of there, but it's a start. Uh, same way, you know, this workout that we were talking about earlier, it's done with a light 20-pound pair of dumbbells, uh, you know, which I bought at Sports Basement for 20 bucks. Uh, and the beauty is I can do that anywhere I am. I can do that in my hotel room. I can do that in my bedroom. I can do that first thing when I roll out of bed. So there's no overhead of going to the gym. So this new daily workout for me, because it's only 20, 30 minutes, uh, right in my living room, uh, takes me less time than the old model of getting into a car and going to the gym and working with a trainer 'cause this is all the overhead that was involved in that model. So I think what you wanna find is you wanna hack in habits that are actually more pleasurable, that are easier, and then they replace your bad habits or, or your not-as-good habits. So the most recent one is I dropped caffeine, for example, which was great. It was fantastic. Uh, and I'm, I'm dropping hard alcohol altogether, and even wine, I don't really drink much anymore. So those seem to me almost unconquerable. For anyone who's gotten used to drinking a lot, it seems like a really difficult habit to break, but it is breakable.

    25. TF

      So how did you crack caffeine, and why did you feel the need to crack caffeine?

    26. NR

      Well, I had a, I had a health issue a few months back, which is a great wake-up call. I think at the, at the beginning of this, uh, session, I talked about how, uh, everything great comes from something bad. And so one of the definitions, Krishnamurti has this definition of suffering that I really liked, where he says, "Suffering is that moment when you see reality exactly as it is, when you can no longer run away from it, when you can no longer deny it." For example, you have a bad relationship with your wife. You're in denial about the whole thing. You're always covering it up. You're always sort of escaping around it or, or, uh, putting a, a finger in the dike and making it work. And then one morning you wake up, and she leaves you.

    27. TF

      [laughs]

    28. NR

      And you're in suff- and you're in suffering. You're in pain. And the suffering is there because now you can no longer deny that things were going poorly. There's no more denial. You're forced to face reality. And when you for-- when you face reality, that is when you will change. So I always look upon suffering as a teacher. Now, it's hard to do when you're actually going through it, but, uh, when you're not, y- you know, that's how you should, like, prepare yourself for it. So in this case, I actually had a bacterial infection is what it turned out to be. Uh, but it could have been a lot worse. So my internal state was bad. I was unhealthy and not feeling well. So literally in one week I dropped, uh, alcohol, caffeine, dairy, red meat, uh, you know, went completely zero carb. Basically, I just switched entirely to meat, salad, water. And all my bad habits disappeared overnight because my body was giving me a very tight feedback loop. Oh, eat the wrong thing, you feel terrible. Uh, and so that was a gift because when I'm 41, my body turns around and tells me, "This is how you need to eat to be healthy." And if I ate perfectly, then the symptoms were a lot less worse.

    29. TF

      Right.

    30. NR

      Now, it was a bacterial issue. Antibiotics killed it. But it was, it was actually amazing because outside of the issues that I was having from the health condition, I felt great. I felt high energy. I felt clear-headed. I felt light of feet and light of mind. Uh, and I became... A- and I wasn't-- I was never before aware of what caffeine does to you. I think we, those of us who drink a lot of coffee slide into it without really realizing what's going on. And once you stop caffeine, for two weeks I was really tired and sleepy, but then I became aware caffeine is a s- is a real stimulant. It would... What it would do is in the morning when I had my-- before I had my coffee, I would wake up like a zombie. I would be groggy and not quite functional. And then I'd have my coffee, and I would be functional, but what happened is my heart rate would be slightly elevated, and I would be slightly stimulated. It's just, it's absolutely a stimulant. And then that would run for about six or seven hours until my next coffee. And then it would slow down, then I would crash, and then I'd be low energy for the night. And when I was forced to drop caffeine, I realized how, uh, I was very consistent energy. I didn't get that stimulation boost at the beginning, uh, but I also didn't get that crash at the end. And as we all know, the candle that burns twice as bright burns half as long.

  14. 2:04:00 – 2:16:28

    Meaning, loneliness, and closing requests: “accept,” book recommendations, and where to find Naval

    1. TF

      Yeah. And for people who've, who feel lonely out there, two recommendations j- that, that I've seen help a lot of people, including myself, check out Couchsurfing. Consider becoming a host for Couchsurfing. And, uh, take a look at AcroYoga if you're in a place where you can find AcroYoga practice. It is one of the most enjoyable, awesome things you will ever do. Um, two more quick questions. If you could have one billboard anywhere with anything on it What would it say? Where would you put it?

    2. NR

      [laughs] Uh, I don't know if I have messages to send to the world. Uh [laughs] , but, uh, there are messages that I, I like to send to myself at all times. Um, one, one message that really stuck with me when I figured this out was that what is desire? And desire is a contract you make with yourself to be unhappy until you get what you want, and I don't think most of us realize that's what it is. I think we go about desiring things all day long and then wondering why, why we're unhappy. So I like to stay aware of that, uh, because then I can choose my desires very carefully.

    3. TF

      Mm.

    4. NR

      I try not to have more than one big desire in my life at any given time, and I also recognize that as the axis of my suffering. I realize that that's where I've chosen to be unhappy.

    5. TF

      Mm.

    6. NR

      Uh, so I think that, that is an important one. Um, or even a simpler one is, uh, you know, in a lot of meditative... Like you said, you did a transcendental meditation course. They give you a mantra. Um, the mantra's supposed to have actually no meaning. Maybe the universal mantra, you know, that's been derived through the ages is om, where you kind of just sit there and say om in your mind to yourself.

    7. TF

      Right.

    8. NR

      It's strange. You can say it to yourself all day long in your mind, and it'll make you happy and more peaceful. You start chanting it out loud, and they'll lock you up. [laughs]

    9. TF

      [laughs] Sim- similar to I will be an amazing cartoonist.

    10. NR

      Exactly.

    11. TF

      I wanna, I wanna interview the guy who, like, sat outside the bathroom and was like, "There's no fucking way I'm going in there."

    12. NR

      [laughs]

    13. TF

      "I'm gonna get murdered."

    14. NR

      Exactly, until Scott Adams shuts up.

    15. TF

      [laughs]

    16. NR

      Um, but om, om has no meaning, I think, but to me it has a meaning, and the meaning is just accept. Just accept. Uh, in any situation in life, you only have three options. You always have three options. You can change it, you can accept it, or you can leave it. Those are your three options. What, what, what is not a good option is to sit around wishing you would change it but not changing it, wishing you would leave it but not leaving it, and not accepting it. So, uh, it's that struggle, that aversion, uh, that is responsible for most of our misery. So probably the phrase that I use the most to myself in my head is I just tell myself one word: accept.

    17. TF

      Accept.

    18. NR

      So any time I look at myself and I'm judging something, I just say accept. And, and it's only very, very, very few things that I will choose not to accept. And if I don't accept something, it's for one of two reasons. Either I'm aware that this is something that I, it's just so important to me right now that I can't accept it, and now I'm gonna put up with a mental battle for it, or more likely, I've just lost control of my thoughts. I'm no longer present. I'm dreaming. I'm in a highly emotional state.

    19. TF

      I need to do more of that myself. And, uh, I'm sure that there, we could go on for a very long time, and I'm sure we will continue [laughs] to do this another time.

    20. NR

      [laughs]

    21. TF

      Uh, but what ask, if any, or request would you make of the people listening to this?

    22. NR

      Well, I mean, I, I think I love books. I love to learn. Uh, I wanna be good at, you know, everything that matters to me for, for, for my own reasons, not, not to, uh, impose or show off anything to anybody else. Um, so what I would ask you is, uh, what is the one book that you've read, uh, that had the greatest influence on your life? Uh, it can be anything. Um, but with the realization that all knowledge is ultimately personal. Uh, you know, none of us should be, uh, we should never be taking our advice and thoughts in pre-bundled beliefs and systems. Uh, both Bruce Lee and Krishnamurti were, uh, real believers in this. Like Bruce Lee was... You know, he set up a school of Jeet Kune Do, which was his style of fighting that he created, and they set up the school, and then he sort of had a realization that no, no, all real learning is, is, uh, unique to the person who's doing the learning and, and you cannot be taught. You have to learn for yourself. Um, so he actually tried to dismantle the school. [laughs] He, he decided that it wasn't the right way to go about 'cause the act of teaching alone caused you to formulate a system, and that system traps you from, from thinking outside of the box and, and really self-discovery. So I, I don't, I, I don't want to turn anything that I've recommended, nor what people recommend to me, as a prescription, "This is how you should live your life." But what I would love to have is just a collection of amazing books that have great insight, um, from people who have solved hard problems.

    23. TF

      Cool.

    24. NR

      And, and generally, the older the book, the better it is.

    25. TF

      Mm-hmm.

    26. NR

      That's m- that's one of my criteria. So don't hesitate to recommend something that might be 500 years old.

    27. TF

      And would you, would you like people to put those in the comments on the blog post that's going to ac- uh, accompany this podcast or let you know on Twitter? What's your preference?

    28. NR

      Yeah, I think either mechanism. The comments would probably be ideal, uh, so we have them all in one place.

    29. TF

      Yeah.

    30. NR

      Uh, but just pick the one book that has most influenced you. It's probably, it's probably that dog-eared book that you've read 5, 10, 20 times.

Episode duration: 2:16:29

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