The Exchanges

Q If you read what everybody else is reading, I mean, there's wisdom that you're going to think what everybody else is thinking. So you need the diversity and almost like an index fund approach, right? 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 that is contextual.

A Yeah, I think almost everything that people read these days is designed for social approval. Um, you know, all the best sellers are about social improvement, social conditioning. Um, if you really wanted to be successful, happy, blah, blah, blah, all those external metrics, you're looking for a non-average outcome, and so you can't be reading the average thing, to your point. Um, and all these things are actually as old as the hills. You can go read Adam Smith and the Wealth of Nations. You can Go read Benjamin Franklin and his aphorisms and understand how to live your life. You could read, uh, Charlie Munger. You could read, you could read Charles Darwin and understand evolution in the source. You could read Watson and Crick and understand the structure of double helix and DNA. But instead, what we choose to read are just, uh, you know, whatever's number one at the airport bestseller or whatever our friends are reading. Or we read, I know people who have read a hundred regurgitated books of evolution and they've never read Darwin. Uh, Or they've read, they've got, or, or think of the number of macroeconomists, and they're out there. I think there's most of them who have read tons of treatises in economics, but haven't read any Adam Smith.

AI assessment note: “you're looking for a non-average outcome, and so you can't be reading the average thing”

Q What are the books you're rereading now? Um, it's a good question.

A Uh, I'll pull up my Kindle app as we talk. Um, but usually I'm always rereading some books on science. Uh, like I just re I read, uh, uh, seven brief lessons on physics. I think that was the name of it. Um, I've read that one at least twice. I'm rereading Sapiens again because I love that book so much. Um, I'm pretty much always reading, rereading something by either Jiddu Krishnamurti or Osho. Those are kind of my favorite philosophers. Um, I'm reading a book on Rene Girard's mimetic theory. It's more of an overview book because I couldn't make it through his actual writings. Um, I'm reading Tools for Titan, Tools of Titans, Tim Ferriss' summary book of what he's learned from a lot of gay performers. I'm, I'm rereading Stories of Your Life and Others by Ted Chiang. It's one of my favorite sci-fi novels. I'm reading a book on, uh, called, uh, Thermo Info Complexity. It's actually by a friend of mine. It's not published yet. I just finished reading Persuasion. Well, I should say I finished skimming Persuasion with Robert Caldini. Um, I don't think I needed to read the entire book to get the point, but it was still good to read it, to read what I did. Um, I, I re, I recently reread, uh, The Lessons of History by Will and Ariel Durant. Um, it's a great little book. Yeah. I am, I'm currently reading The Story of Philosophy also by Will Durant. Um, I have a young kid now, so I've go…

AI assessment note: “I'm rereading Sapiens again because I love that book so much.”

Q I want to circle back and ask you a few more questions about life before we wrap up. 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?

A Yeah, the rational part means that I have to reconcile with science and evolution. Um, so, uh, and I have to reject all the pieces that I can't verify for myself. So 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 of these things I've verified for myself. And some of the beliefs that come out of Buddhism, um, I believe and follow because again, I've verified or reasoned with thought experiments there myself, but what I will not accept is Is things that are written down as just so. Like, oh, you're, there's, there's a past lives that you're paying off the karma for. Well, 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, you know, your third chakra is opening and your second chakra is, I don't know, this is fancy nomenclature, right? 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 I just, then it may be true, it may be false, but it's not falsifiable. So I cannot view it as a fundamental truth. Um, on the other side, I do know that evolution is true. I do know that we are, uh, you know, evolved survival and replication machines. Uh, I do know that we have an ego so that we get up off the…

AI assessment note: “the rational part means that I have to reconcile with science and evolution.”

Q That's a thingy explainer, right? The book, I think?

A Oh, yeah. I'm sorry. You're right. The name of the book is Thingy Explainer. Yeah. And upgoer five is one of the pages. There's another great book that I've called Thinking Physics. I open this one all the time. And I love, on the back cover, it has this great little pitch. It says, the only book that's used in both grade school and graduate school. And it's true. It's all simple physics puzzles that can be explained to a twelve-year-old child they can puzzle over, and it can be explained to a twenty-five-year-old grad student in physics. And they all kind of have fundamental insights in physics. They're all kind of tricky, but anyone can get to the answer through purely logical reasoning. Um, I love reading, uh, the history of how scientists came up with their various breakthroughs, and if you, uh, have ever gone, like, for example, relativity. Relativity is a fascinating thing. It's a very advanced concept, but in a way, it's very simple, because, uh, Einstein came up with it with what are called Gedanken, fancy word for thought experiments. This means thought experiments in German. So he was able to basically just do logical thought experiments in his mind until he came up with relativity, and then he formalized it with mathematics and with Uh, predictions that he made that were later, uh, unfalsified, that were basically shown to be true. So, um, really brilliant physicists…

AI assessment note: “Oh, yeah. I'm sorry. You're right. The name of the book is Thingy Explainer.”

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

A Yeah, that's a big question. I'll give you three, because it's a big question, I'll give you three answers. Uh, one is it's personal. You have to find your own meaning. Any piece of wisdom that anybody else gives you, whether it's Buddha or you or me, it's going to sound like nonsense. So I think fundamentally you just have to find for yourself. So the important part is not the answer. It's the question. You just have to sit there and dig with a question that it might take you years or decades, but when you find an answer you're happy with, that, that will be fundamental to your life. Uh, the second answer I would give is there is no meaning to life. There's no purpose to life. Uh, Osho says it's like riding on water. Uh, or building houses in sand. Uh, the reality is you've been dead for the history of the universe, whatever, ten billion years or more. You will be dead for the next seventy billion years or so until the heat death of the universe. And anything you do will fade. It will disappear just like the human race will disappear. The planet will disappear. Get to Mars, even, even that group will disappear. So no one's gonna 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. Um, so you have to create your own, own meaning, which is what it boils down to. You have to decide, is …

AI assessment note: “one is it's personal. You have to find your own meaning.”

Q When you first pick up a book, are you skimming for something interesting? Like, how do you go about reading it, or do you just flip to a random page and start reading? What's your process for that?

A Yeah. I'll start at the beginning, but I'll move fast. So if it's not interesting, I'll just start flipping ahead, or I'll start skimming or speed reading. Uh, 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. Um, I don't believe in delayed gratification when there's an infinite number of books out there to read. There's so many great books. And there are so many of them that are so well written that, you know, I just can't spend my time on these. Um, one thing I will do though is 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 where the epistemological load of acknowledging that contradiction, sorry to use that 50 cent word, but just, I would have to revisit my entire lifetime of learning, and undo it, and start over. Yes, yes, gravity does not exist. Yeah, exactly. Or like, you know, I had a very, 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, And then he basically said, and as we know, you know, thermodynamics isn't really true. That was the point in which I was like, okay, I gotta discard everything you just said, because the…

AI assessment note: “I'll start at the beginning, but I'll move fast.”

Q 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?

A Uh, by not having a strong sense of self or judgments or, or mind presence, the monkey mind will always respond with this regurgitated emotional response 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. Um, like for example, in January this year, I wrote like a little piece on, 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, right? 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. So I think the number one thing that clouds us from being able to see reality is just that we, um, we just have preconceived notions of the way it should be. Uh, there's a, one definition of a moment of suffering, uh, is that it's that moment when you see things exactly the way they are. So this whole time you've been convinced your business is doing great, and really you've ignored the signs that it's not doing that well, then your business fails and you suffer. Well, it's just because you've been putting off reality. You've been 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. That…

AI assessment note: “by not having a strong sense of self or judgments or, or mind presence”

Q Have your values changed at all, or have you given more thought to them since becoming married and becoming a parent? I mean, how has that changed you?

A Yeah, values almost by definition don't change that much over time, but they take some, it takes some time for you to figure out your own foundational values. I think everybody has them. It's just that maybe we're not that aware of them until later. Uh, and, uh, you know, so it might have changed a little bit, but not a lot. I mean, my, my wife is an incredibly loving family oriented person, and so am I. And so that was one of the foundational values that brought us together. Uh, the moment you have a child, it's this really weird thing, but it's sort of, it answers the built in meaning of life, purpose of life question. And all of a sudden, the most important thing in the universe moves from being in your body into being moving into the child's body. Um, so that, that changes you. And your values inherently become a lot less selfish. Um, you know, I would say that, like, probably the biggest such change was when I was younger, I really, really, really valued freedom. Freedom was one of my core, core values. And ironically, it still is. It's probably one of my top three values, 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. And now I would say that the freedom that I'm looking for is internal freedom. So it's freedom from, it's freedom from reaction. It's freed…

AI assessment note: “so it might have changed a little bit, but not a lot.”

Q What habit would you say most positively impacts your life?

A I think it's the daily morning workout. Uh, that has been a complete game changer. It's made me feel healthier, younger. Uh, it's made me not go out late. Uh, and it came from one simple thing, which is everybody says, I don't have time, right? Basically, whenever you throw any so-called good habit at somebody, they'll have an excuse for themselves. And usually the most common is, uh, I don't have time and I don't have time. It's just another way of saying it's not a priority. So what you really have to do is to say, is it a priority or not? And if, if something is your number one priority, then you will get it. Uh, that's just the way life works. But if you've got a fuzzy basket of 10 or 15 different priorities, you're gonna end up getting none of them. Uh, so what I did there was I basically just said, my number one priority in life, above my happiness, above my family, above my work, is my own health. And it starts with my physical health. And then second is my mental health, and then third is my spiritual health, and then it's my family's health, then it's my family's well-being, and then after that, I can go out and do whatever I need to do to the rest of the world. So there's a series of concentric circles starting out for me, and so because my physical health became my number one priority, then I could never say I don't have time. So in the mornings, I just work out, and…

AI assessment note: “I think it's the daily morning workout. Uh, that has been a complete game changer.”

Q How is radical honesty? Like how radical is your honesty and how is that kind of impacted your life?

A Uh, I mean, it's pretty honest. I'm not like the, I think Ray Dalio from Bridgewater is famously radically honest. Um, so I'm not going to go and call somebody ugly to their face. Like I'm not trying to make a big show of it. Um, I'm not trying to say, Hey, I'm so honest and I'm going to shock you. Um, what, what radical honesty just means that I, 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. Uh, and it also means, you know, Richard Feynman famously said, uh, you should never ever fool anybody, and you are the easiest person to fool. So the moment you tell somebody else something that's not honest, uh, you've lied to yourself, and then you'll start believing your own lie, and then that will disconnect you from reality and take you down the wrong road. Um, so it's really important for me to be honest, but I don't go out of my way volunteering negative or nasty things. Uh, I would combine radical honesty with an old rule that Warren Buffett has, uh, which is praise specifically criticized generally. Uh, and I try to follow this. I don't always follow it, but you know, I think I follow it enough that it made a difference in my life, which is if you have a criticism of someone, then don't criticize the person, criticize the general approach or criticize kind of that Class of, uh, activities. Um…

AI assessment note: “I mean, it's pretty honest. I'm not like the, I think Ray Dalio”

Q 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 times, which was, um, you know, how would you fix it? What's your opinion on the education system? What are your thoughts around that?

A I think there's no question. It's completely obsolete. Uh, the, the education system is a path dependent outcome, uh, from the need for daycare, uh, from the need for prisons for college age males who would otherwise overrun society and cause a lot of havoc. Uh, the original medieval universities had guard towers that face inwards, for example. Um, yeah, cause you, you have to put a curfew in there and you need to lock up the young Uh, 18 year old males before they go out with swords and daggers and, you know, create trouble. Um, so, uh, college and schools, and the way we think about them, they come from a time period when books were rare. Knowledge was rare. Um, babysitting was rare. Crime was common. Violence was prevalent. Uh, there was no such a self-guided learning. So, I think schools are just, uh, byproducts of these kinds of institutions, and now we have the internet, which is the greatest web of knowledge ever created, completely interconnected. So 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, you can get MIT and Yale lectures online, you can get all the coursework, you can get interactivity, you can read blogs by brilliant people, you can read all these great books. So it's, so the ability to learn, the, the means of learning, the tools of learning are abundant and infinite. It's a …

AI assessment note: “I think there's no question. It's completely obsolete.”

Q too in checklists. Um, you mentioned kind of like how you determine if you can trust somebody, and I know you've said in the past you've kind of used Buffett's criteria for evaluating people, which is the combination of intelligence, energy, and integrity. What, what predictive signals do you pay attention to for each? How do you determine if you can trust someone? A large part of your job is-

A That's the hardest one. Yeah, integrity is the hardest one, and integrity is a, it usually comes out in two ways. One is long-term, which is just you've known somebody for a while, and you kind of know, you know, how they think about things. Uh, but the most, the more interesting one, there's a short-term one, which is you just kind of see how they treat other people. So there are lots and lots of people who will, uh, you know, not screw over, screw over is a strong word, but they will do something that is self-feeling or slightly unethical, um, relative to another business partner. Um, but the whole time they'll, they'll say to you, nudge, nudge, wink, wink. Uh, you know, I'm taking advantage of that person cause they deserve it, but you're my friend. I would never do that to you. Um, and the thing is, yeah, exactly. It's very easy to change your definition of who friends are. Uh, I find that the people who really do it, things out of integrity, they have an internal moral compass. So they don't, uh, they don't do, uh, 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. Um, so some of the highest integrity people I know, the worst thing you can do is you can say to them, well, I think you're self-dealing on that one, and they will get so unhappy, because they'll be…

AI assessment note: “a short-term one, which is you just kind of see how they treat other people.”

Q You mentioned happiness being one of your top priorities. What is happiness to you? Like, what does that mean? What does that word mean? Can you unpack that?

A Yeah, it's a very evolving thing. I think like all the great questions, um, you know, when you're, when you're a little kid and you go to your mom and you say, what happens when we die? Is there Santa Claus? Is there a God? Should I be happy? You know, who should I marry? Those kinds of things. There are no glib answers to that because there are no Uh, there are no answers that apply to everybody. Um, so these, these questions, the search for truth, you know, these kinds of questions, they ultimately do have answers, but they have personal answers. So the answer that works for me is going to be nonsense to you and vice versa. Um, so whatever happiness means to me, it means something different to you and it means something different to the listener. Um, but I think it's very important to explore what it is. And for some people, I know it's a flow state. For some people, it's satisfaction. Uh, for some people, it's a feeling of, uh, contentment. Um, The best, my definition keeps evolving. Um, so the answer I would have given you a year ago would be different than what I tell you now, but today I believe that, uh, happiness is, uh, it's really a default state. It's what's there when you remove the sense that something is missing in your life. Uh, and we are highly judgmental survival and replication machines. We're constantly walking around thinking, I need this, I need that, trap…

AI assessment note: “happiness is, uh, it's really a default state. It's what's there when you remove”

Q How do you keep track of that all? Like, what does your typical day look like?

A Well, that's the good part. I don't have a typical day, nor do I want a typical day. Uh, you know, if there is a typical day, I'm usually inside my office at AngelList. Um, but I'm basically just operating mostly on email or phone or meetings or, or, or squirreled up at home. So there are days where I just work completely from home. There are days that I don't work. Uh, I'm actually even trying to get rid of this concept of having to be in a specific place at a specific time. Uh, you know, all I care about is, uh, am I doing what I want to do, and am I being productive, and am I happy? I really want to break away from this idea of 40 hour weeks, or 60 hour weeks, or 80 hour weeks, or nine to five, or roles, or jobs, or identities. Uh, it just all feels like a straitjacket.

AI assessment note: “I don't have a typical day, nor do I want a typical day.”

Q So what's a habit that you're trying to, to change right now? What are you working on?

A Well, I, I did a lot of habit changes over the last few years. So I've now got a daily workout that I do, which is a great habit. I cut down heavily on drinking. Uh, it's not fully eliminated, but it's mostly gone. Uh, I dropped caffeine. Uh, Uh, I'm not on the paleo diet, although I like to be, so I'm on a variation of it that I call the paleo diet, which is I try to be paleo, but I fail constantly, but I don't beat myself up over it, because I feel that even approximating towards it is better than where I have been historically. Um, so, you know, like that, uh, I tried to build a meditation habit, but I, but I failed, but I have made a habit of being meditative. Um, so I've gone through lots of habits. Uh, probably the one that I'm currently would like to cultivate is doing yoga, uh, more regularly, but I haven't really, uh, I haven't formulated a plan around that. And by the way, I reject a lot of the stuff that's being peddled around today about how you perform and break habits. I know there's this very popular book, one that I even recommended, which talks about the science behind habits. And one of its depressing conclusions, I think this came out of Stanford, was that you can't break habits. You can only replace them. Uh, and that's BS. I've definitely broken habits completely. And so I think you can uncondition yourself. You can untrain yourself. It's just hard. Um, so …

AI assessment note: “probably the one that I'm currently would like to cultivate is doing yoga”

Q Yeah, I think that's true. Um, when you're reading, do you just read and it sticks in your head, or is it more... Like, you take notes, do you have a system for how you keep track of that or review them?

A I'm both lazy, and I'm really focused on being present. So 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. Uh, and then who really sits there, you know, uh, years later and goes back and looks at all their trip photos and gets nostalgic. Just go take your next trip. So I, I just don't believe in anything from the past, anything, no memories, no regrets, no people, no trips, nothing. Cause a lot of our unhappiness also comes from comparing things from the past to the present. First time you saw a sunset, it was amazing. It was jaw dropping. You forgot yourself. The second time you saw it, it was cool. You know, the 100th time you say it's nothing. The 1000th time you're saying, and someone shows you a sunset, you're like, well, actually, I saw this one sunset in Mexico this time. That was really cool. You're not even there. So I, I just don't believe in clinging too much to memories, and that includes in reading. So I, I do highlight, I catch myself doing that, but I do it more because it's just kind of a way of rereading and rereading that particular paragraph at that moment in time. Uh, and then once in a blue moon for my especially favorite books, I'll want to reread the book, but I'll be short on time, so I'll just reread the highlighted passages until something catches my eye, and then I get sucked bac…

AI assessment note: “note-taking is even, I think, harder than that, so I, I do not take notes.”

Q Most of the people that I know that read, uh, quite a bit, they have a reading habit like you. You're described as a very habitual person. Where did that come from?

A Oh, that might've come from the Tim Ferriss podcast. Uh, I, I don't think I'm more habitual than anybody else. I think human beings are entirely creatures of habit. Uh, you know, as a young children are born with no habit loops, they're, they're essentially born as blank slates. Uh, and then they habituate themselves to things and they learn patterns and they get conditioned and they use that to get through everyday life. And habits are good. You know, habits can allow you to, uh, background process certain things so that your, your neocortex, your foregroup, Your frontal lobe stays available to solve brand new problems. Uh, but we also unconsciously pick up habits in the background, and we keep them for decades, and we may not realize that they're bad for us, so we're ready to move on from them. Um, to some extent, you know, our attitude in life, our mood, our happiness levels, depression levels, these are also habits. Uh, do we judge people? Uh, how often do we eat? What kinds of food do we eat? Do we walk or do we sit? Do we move? Do we exercise? Do we read? These are habits as well. Uh, and we, you absolutely need habits to function. You cannot solve every problem in life as if it's the first time it's thrown at you, but, but what we do is we accumulate all these habits. We put them in the bundle of identity, uh, ego ourselves, and then we get attached to that. I'm Shane. T…

AI assessment note: “Oh, that might've come from the Tim Ferriss podcast. Uh, I, I don't think”