The Tim Ferriss Show - #410: Ryan Holiday — Turning the Tables

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Starting point is 00:05:04 Well, hello, boys and girls, muskrats and squirrels. This is Tim Ferriss. Welcome to another episode of The Tim Ferriss Show. This is Tim Ferriss. As I think I may have already said, it is usually my job to sit down with world-class performers of all different types from different areas to tease out the habits, routines, favorite books, and so on that you can apply and test in your own lives. This time time we have a turning the tables episode. What does that mean? It means I'm not doing the interviewing. Instead, I will be getting interviewed by my friend Ryan Holiday. He and I wanted to get together, so we figured why not record the entire thing. And who is this Ryan fella anyway? Ryan Holiday on Twitter and Instagram

Starting point is 00:05:43 at Ryan Holiday is one of the world's foremost thinkers and writers on ancient philosophy and its place in modern life. He's a sought after speaker and strategist and author of many bestselling books, including the blockbuster, The Obstacle is the Way, which has been used by many of the top coaches and competitors in the NFL, military and elsewhere. Ego is the Enemy and The Daily Stoic. His books have been translated into more than 30 languages and have sold more than 2 million copies worldwide. He lives with his family outside of Austin, Texas. You can subscribe and receive his writing at ryanholiday.net. It does some really, really good reading list recaps and recommendations,

Starting point is 00:06:20 and dailystoic.com. Ryan was also the fourth ever podcast guest on this podcast in the very, very beginning. So he's been along for the ride and he's written multiple popular guest posts for my blog, which you can all find at tim.blog, including beginner's guides to stoic philosophy, of course, which I have spoken about and written about a lot, including in the TED Talk, which can be found at tim.blog forward slash TED. Ryan's latest book is Stillness is the Key, which was an instant number one New York Times bestseller and Wall Street Journal bestseller. I also recommend, if you'd like video, checking out the interview, this interview on YouTube, since we captured video from multiple

Starting point is 00:07:05 angles for this conversation. You can find that at youtube.com forward slash Tim Ferriss, of course, with two R's and two S's as per always. Please enjoy. I've known you for a long time, and I was thinking one of the biggest changes that I've seen in you as a person came when you got your dog. And I remember you approached it in very Tim Ferriss fashion. You didn't just like, hey, like me, like I got a goat one day because we saw it on Craigslist and we just like went and got it.

Starting point is 00:07:35 But that's not the Tim Ferriss way. Yeah. You were like, you talked to a bunch of people, you read a bunch of books, but you ultimately end up, was it 10 years ago you got a dog? Four and a half years ago. Maybe five. But it's been an interesting pivot in your life. Why do you think it impacted you so much? outside of any type of self-indulgent reflection slash obsessive compulsive rumination.

Starting point is 00:08:17 Sure. who has had a history of depression, which is being stuck in the past, and I think being highly self-referential. Depression is, I think, as someone who's experienced it a lot in life, very self-obsessive. When you have something in front of you that requires and demands care, or it's going to pee on your carpet every two and a half hours, like Molly, my dog, it's incredibly anti-depressive in that sense because it forces a complete refocus. I also, I think, realized very quickly how absurd some of my reactions are to things or have been historically in the sense that if you have a problem at work, you have a problem with your partner, your spouse, your girlfriend, boyfriend, you can get upset and sort of create an imaginary agenda that they have where they deliberately did A, B, or C to upset you. But with a dog, that's completely absurd.

Starting point is 00:09:23 Like at face value value it's completely absurd right so some of the problems are your fault it's your fault right so if your dog chews on your shoes that's your fault it's a dog and you left your shoes out right so a big part of i think raising a puppy well is making it extremely difficult to make mistakes that then become habits. That's an approach or at least a lens through which you can look at raising a puppy. And if you don't want your dog to develop a taste for chewing on shoes, don't leave your shoes out. Put them on something or in something that makes that impossible.

Starting point is 00:10:00 And similarly, peeing in the house. To avoid that, use something like crate training. And so I think that when I became, particularly in the early periods of training Molly, upset because she wouldn't follow my instructions. Yeah. After an initial period of just getting upset, which I think was my default and has been a default for a long time, anger has been a go-to, emotion, which I think Krista Tippett once said it's fear shown in public or something like that, which I tend to agree with on some level.

Starting point is 00:10:37 Getting upset is fear shown in public? Getting angry. Yeah. Yep. And it's a coping mechanism. Some people shut down. Some people learn to get angry. I to get angry like when I was when I was little so doing that though with this dog who does not speak English was so

Starting point is 00:10:56 ridiculous and ineffective that I had to resort to doing other things that lo-and-behold translate to other people and even to yourself, like positive reinforcement. Yeah. Right? I didn't, through sports and coaching and teaching or receiving teaching, had a little bit of positive reinforcement, but not a whole lot. Yeah.

Starting point is 00:11:16 And so I've learned to go without it, even though that is unhealthy. Sure. And reading about animal training, if you really want to take it seriously, if you look at, say, training marine mammals like dolphins, you can't get pissed and hit it with a rolled up newspaper. It doesn't work underwater, and they're faster than you are. So you have to figure out how to use whistles and different clickers and means of marking the desired behavior and then rewarding. Sure.

Starting point is 00:11:42 And getting into the habit of providing positive reinforcement, I think, led to me doing that more. I could still do it more with other people. And how you treat other people, I think, impacts how you treat yourself and relate to yourself. So I think that those are all pieces of the puzzle. And then last but not least, feeling unconditional love, although granted giving your dog food and treats helps a lot. But feeling this love from an animal and experiencing that in the absence of language, I think is really powerful.

Starting point is 00:12:25 Yeah. As someone who tends to get tangled in their own inner voice in the form of language, to experience that type of deep, positive emotion and connection without language to trip over has been really impactful for me. Do you think it was giving you something to care about, like to be responsible for that wasn't, there's no reason to have the dog. Like you have the dog because you love the dog.

Starting point is 00:12:56 You know what I mean? You're not getting anything out of it in the sense of like, sure you have a nice car, you have to take care of the nice car, but you know what I mean? I think so. I mean, you get a dog because you want a dog take care of the nice car, but you know what I mean? I think so. I mean, you get a dog because you want a dog. It's, in a sense, a very selfish act. Yeah.

Starting point is 00:13:10 Even though you can adopt and do all these other things, as I did with Molly, that one would hope have some positive karmic impact. But ultimately, you are choosing to have a dog. Right. Similarly, I think having kids is, and this isn't a bad thing, it's not a value judgment, but it is a selfish decision. You have kids because you want to have kids, right? Yeah. And I remember Mike Maples, who's this very well-known investor and friend of mine, said

Starting point is 00:13:38 to me, he's like, rule number one with kids is they owe you nothing. Their job is to receive love, not to give you love. Because you decided to have the kids. Right. And I think that's true to dogs as well, or any type of pet. And for that reason, I do not recommend that everybody get dogs, right? Because I think that for a lot of folks, as I felt for a really long time, I was too self-focused slash obsessed. And the only way I could see having a dog was to kind of wedge it into the open spaces that were left over once I had already executed on everything else I wanted to execute on or fixate on. And when I ended up getting Molly, I made the decision that I was going to actually reverse that and get Molly prioritize really taking good care of her and then fit everything else around

Starting point is 00:14:31 the dog right and that's those are two fundamentally different ways to look at it and I think if you look at sort of the realm of behavior in humans and dogs like most animals including humans are poorly trained yeah and to do it well takes a lot of effort and consistency so if someone's ready for that then i i suggest you know adopting ideally but otherwise i've i've seen people who would who get dogs and then just neglect them. Sure. And I'm conflicted as to how to feel about that. Because on one hand, if they're rescuing a dog from a kill shelter. Probably better.

Starting point is 00:15:14 Probably better. One could argue that's better. But I don't know. I'm not, yeah, I'm no professional ethicist. No, there's a thing David Brooks talks about when his son was born. Someone sent him an email and said, this is his first kid. They said, you know, like, welcome to unavoidable reality. And the idea being that up until then, sure, you have responsibilities as work and life, but like pretty much anything you don't want to have to put up with, you don't have to put up with.

Starting point is 00:15:42 Right, yeah. But as soon as you take on something like that, like with a kid, it's like you think, okay, I'm going to go to this thing at 1 o'clock. But if your kid falls asleep at 12.59, you're going to the thing when your kid wakes up. And I think dogs have an element of that too. Suddenly you're responsible for this thing that is totally dependent on you. And the dog decides what the schedule is, not you, which if you're successful or self-absorbed,

Starting point is 00:16:08 and they're kind of the same thing in different ways, it forces you to pivot your reality in a way that makes you a better person, I think. I think so. And you develop, I don't really want to use the word patience. I think it's something else, maybe greater self-awareness and resilience in the face of the unpredictable equanimity is what i think yeah equanimity we

Starting point is 00:16:34 could use because it's like all right molly gets sick i'll give you an example like i remember one morning i woke up to the like the most awful stench imaginable at like 4 in the morning. Right. And I'm very protective of my sleep. Historically, one of the best ways to get me really spun up and upset is to negatively affect my sleep. Okay. And it's like 4 in the morning, went to bed at 1. Yeah.

Starting point is 00:17:03 And the most horrible stench you can imagine. I wake up, I turn on the light, and Molly has just shit everywhere in the bedroom, including on the wall, which I thought was very impressive. I'm like, what possesses a dog to shit against the wall? I don't know. Nonetheless, it's like, all right, this is what you're dealing with for the next hour, two hours, is putting on your hazmat gear and dealing with this and i think you develop or i have developed to some extent i don't think i'm the best at this but the ability to

Starting point is 00:17:33 put my better put myself in other people's shoes sure because in a situation like that it's clear to me molly doesn't want to do what she's doing right there's something I do this to ruin your sleep she's not good to ruin my sleep and it's it's it's not just unhelpful but it's damaging to lose your lose your husband said lose your shit but to get really upset in a situation like that. It actually makes it harder to train your dog effectively. So the unavoidable reality piece, I think, is a big part of it. And I think there's something to be said for a phrase I heard recently. This scientist I've come to know really well, when he had his first kid, and he had his first kid pretty late by his standards.

Starting point is 00:18:28 He's a lot older than I am, so I'm like an 80-year-old when it comes to possible procreation these days. But he said his brother, who had a few kids at that time, said, oh, welcome to the human race. His first kid was born. Sure. And I do think that it doesn't need to apply to everybody, but there is a certain self-absorption that is encouraged and fostered in modern life that I think is relatively new. Yeah. Does that make sense?

Starting point is 00:19:02 Because even in a densely populated city, you can be very physically isolated and you don't have responsibilities or things to care for that for the vast majority of our evolution would have been commonplace. You're not even kids at like 19 or 18. You don't live with your grandparents. You don't live with your grandparents. You're not hunting and gathering where dogs would certainly have played a role and did play a role. So I think that in some way, having a dog or

Starting point is 00:19:43 having a garden or having kids, these are all things we've evolved, sort of co-evolved with. Totally. And in the absence of that, you develop a lot of neuroses, which I was sort of the poster child for, for a really long time. And probably still am on some level, but less so. I think that's really interesting. The idea of like sort of consciously developing empathy is, and how almost you could argue that the way society is set up now consciously stunts the development of empathy. Like the famous one, you're like, oh, you hear someone else like,

Starting point is 00:20:15 how was your flight? And they're like, oh, it was terrible. I sat next to this like crying baby the whole time. Then you have kids and you're like, you get on a plane, you hear a crying baby. You don't go, oh, there's a crying baby. This is bad for me. You go, that baby is upset.

Starting point is 00:20:27 It literally never occurred to you that the baby was crying because there's something wrong with the baby and that this isn't fun for the baby. And it's definitely not fun for the parent. They don't want it. So I think with dogs too, you hear dog barking, you hear about those, you like oh i've been through that or oh that's not fun for you yeah it sort of forces you i think that's what they mean by that

Starting point is 00:20:50 idea of welcome to the human race not welcome to the human race you now have like made you know you're reproducing it's welcome to the human race you're no longer like a lone wolf you like understand like how you understand what everyone else has been dealing with while you've been self-absorbed this entire time yeah it's sort of also like welcome to the human slash hominid condition yes that was the norm for right like millennia yes has been the norm and like thank god you've snapped out of your aberrant strange behavior that is really kind of a new luxury yeah that's right did you have you felt like moving to Austin has has had an impact on you in a similar way like I feel like that there is also something selfish and strange

Starting point is 00:21:38 about the New York life or the San Francisco life or the the LA life, that I've just experienced the South and Texas being a little bit different. Yeah, well, Texas, the South, and Austin are all a little different. A little different, but I understand what you mean. I think that Austin has been so far, let's call it three years in, three, four years in, however long it is, has been very refreshing and rejuvenating in part, and this is coming back to your point about observation about New York and LA and so on, in part because there is no one mono-conversation.

Starting point is 00:22:21 And that could be seen as symptomatic of a huge benefit of living here or a huge drawback meaning there's certain there are certain locations in the world like New York for finance in New York you have finance yeah true in other places to say London if you want to be in the NBA all-star game of finance, it behooves you to go to one of those places. Sure. As a result, it attracts people who are highly driven in certain fields, whether that's fashion, finance and so on.

Starting point is 00:22:59 As you've mentioned to me before, I think there's a high correlation between self-absorption and professional success on some level. Yeah, it has to be. And if you look at Los Angeles, even though Los Angeles is a huge, in reality, combination of different cities, entertainment is the predominant mon conversation. Whereas here in Austin, you have more of a medley. Yeah. And for that reason,

Starting point is 00:23:33 I find it, I find that I don't overtax a single sort of conversational track or part of my brain. You can quite easily hop from lily pad to lily pad and maintain some degree of mental dexterity emotional dexterity there's just there's just more to easily dip your toe into here yeah and it does exist in a place like san francisco but it takes more effort to avoid the mono conversations.

Starting point is 00:24:08 Don't you think one of the downsides of the mono conversation is also, let's call it mono thinking, right? So I think we have tended these days to define diversity as merely a function of race or gender. a function of race or gender, but I think diversity as far as lifestyles, thinking, careers, interests, you know, is also super important. The main downside of the mono conversation is mono thinking. And a group think that produces an echo chamber that at least in my experience doesn't stress test a lot of your own beliefs because you end up succumbing to this preaching to the choir yeah and that i

Starting point is 00:25:00 think is um i think it's very dangerous yeah i think it's very dangerous i think in silicon valley where you have so much capital and so much power so much culture shaping technology that uh you really want to have not necessarily a court jester but someone who can poke fun at the status quo and challenge deeply held beliefs, or I should say better yet, deeply assumed beliefs. Yeah. And that is very increasingly difficult to do in the Bay Area and in much of certainly culture in the United States. And we're in Austin, which is jokingly referred to as the blueberry and the tomato soup.

Starting point is 00:25:51 Yeah, the blue dot in the red ocean. Yeah, and so it is, one might think that Austin is just a smaller version of San Francisco, but it's not. You do have a commingling of sort of political, artistic, and financial interests that I deeply enjoy. And the ability to easily, for instance, I mean, we're sitting here right above a restaurant called Jeffrey's and next door is Josephine House and I had dinner at Josephine House

Starting point is 00:26:34 with someone, I won't mention by name, most people wouldn't recognize him, but an extremely successful investor, a financier who came in from out of town, came in from elsewhere in Texas, very well educated, extremely smart, and also a sort of staunch Republican on many levels, not all levels, right? It's easy to paint with that broad brush. And when you have the ability to sit down with someone like that easily here, it becomes harder to do

Starting point is 00:27:07 what is so frequently done in San Francisco as a place where I spent a lot of time, almost two decades in the Bay Area, to say, oh, right-wingers are all knuckle-dragging idiots. It becomes much more difficult to paint. Because you know by direct first-hand experience that that's not true. It's not that.

Starting point is 00:27:29 It's not true in many cases, and it's just not that simple. Right. Right, it's just not that simple. And it forces you to contend with, I think, a messy reality that it behooves all of us to recognize as messy. Yeah.

Starting point is 00:27:45 It just requires more thought. But I like the fact that it's not as easy to kind of divide this country into like a left-right civil war. Yeah. Of smart versus dumb, rich versus poor, this versus that. It's not as easy to do here.

Starting point is 00:28:05 And I like that. Yeah. I also think that it would be difficult for me to live in many places outside of Austin in Texas. Sure. Right? Which is not a slight against Texas. It just means that Austin has a combination of factors. It's the combination of factors that makes it interesting to me. And the

Starting point is 00:28:25 fact that it has some of the ingredients, and we'll see if this backfires over time, it might, but that made Silicon Valley, Silicon Valley. You have large, famous research universities with world-class talent from dozens of countries around the world and and it attracts a very intellectual crowd yeah and as you and i know i mean there is an incredible writing scene here there's some fantastic writers and uh it it it has a lot of the ingredients i like about silicon valley without the sort of smug self-satisfaction that I find so unappetizing. You know what I think is important when I was sort of like thinking about places to live is like you're naturally a competitive person. You're sort of keeping up with the Joneses part of it. Like it's very easy for life to become an arms race, right?

Starting point is 00:29:26 And when you live in a place with more diversity, where you live where there's not sort of one industry or one scene that dominates all the others, you become more inwardly focused on what you want to do and what's important to you, rather than going, oh, did you hear what so-and-so just got? And I think that's a healthier way to live also. Yeah, I think that's a very good observation.

Starting point is 00:29:49 There's no one lead dog to follow. Yes. Right? And as a result, you have to make more conscious decisions about who you might want to emulate. It's not an immediate default. Yeah. And I like that.

Starting point is 00:30:07 I also don't know if Austin would be the right place to live. It probably wouldn't for many industries if you are in your 20s and looking to cut your teeth and make your mark and kind of summit the mountain. Sometimes you need that to drive you forward, but that maybe isn't how you want to spend your whole life. Yeah, I think that there's a point, at least there was for me, where you've basically alternated between park and sixth gear.

Starting point is 00:30:37 And you're like, oh, wait, there are five other gears. I don't actually need to have this binary lifestyle that is either like rest and recover or full out sprint for the Olympic gold medal. other ways that were I geographically located in one of these no holds barred type A cities, I probably wouldn't give myself the slack in the system to discover. I would like to think it doesn't matter where I am. I can cultivate all these amazing habits and types of awareness that will allow me to blah blah blah blah blah but the reality is uh i'm highly flawed with all sorts of predispositions and i am to my benefit and often to my detriment highly highly competitive yeah so if i'm if i'm thrown into any game even if it's a stupid game

Starting point is 00:31:45 that I shouldn't participate in, You want to win. I'm going to want to win. And recognizing that is important. I remember having Peter Thiel on the podcast long ago. I've listened, yeah.

Starting point is 00:31:58 Yeah, and I believe, I don't remember the context exactly, but one of the questions, and I'm paraphrasing here, I believe one of the questions he asks himself is, in what areas of my life can I be less competitive to be more satisfied or more content? Yeah. And if your default is competition, I think it pays huge dividends to be aware of that and to ask those types of questions. My favorite line from him is that competition is for losers.

Starting point is 00:32:28 Competition is for losers. No, but I think what is interesting about you, though, is you are a very competitive person. And yet, and this is something I wrote down to ask you about, you have a habit of walking away from things that you're at the top of, right? So, correct me if I'm wrong, but I think your decision to sort of stop angel investing or stop actively angel invest coincides with their decision to

Starting point is 00:32:51 move to Austin or that overlaps? Yeah, very, very much an overlap. Yeah, 2015 and then shortly thereafter. So how much, one, I'm curious about your decision to sort of, you you know you're not putting out a book a year even though you could make a lot of money and sell a lot of copies you sort of have have sort of been disciplined about what you don't do but how much of that is also related to like designing a life or a day-to-day reality you know how much are how much are they connected? I think they are all really interrelated. And I'm not going to try to fabricate some grand master plan because I don't have one. But I do think that I tend to pause and try to reflect and ask a lot of questions. When I feel that my decisions in any area of my life begin to bleed into fear of missing out or scarcity or fear-based decision making, not perfect. But in the case

Starting point is 00:33:58 of angel investing and the reason I stopped effectively all of it in 2015 or so is that I realized the conditions were becoming more difficult to place effective bets, especially as an individual using their own capital versus a fund with a nice 2% management fee and 20% carry when you're using other limited partner money, which is a fine model. I don't have an ethical issue with it. But I realized that to do a good job with an increasingly high number of decks in the blackjack game, in the form of bloated terms higher prices uh foreign capital flight from places like china coming into the u.s and affecting terms i would either i could no longer do an effective job part-time yeah and that i if i wanted to continue to compete in that game i would need to create a fund do it semi full-time and that world, I would be effectively replaceable. I would be in a long line of people trying to do the same thing.

Starting point is 00:35:10 And that my drive to do that would be predominantly driven by fear of missing out and I think a sort of cortisol-driven scarcity mentality that is really fostered in the world of startups. Sure. And even if I were to win that game, I felt like the toll it would take would not be worth the sort of Faustian bargain. Yeah. In other words, from a mental health perspective, from a physical health perspective, from an emotional health perspective, that it would end poorly. And I tried to make a realistic assessment of my track record in angel investing, which has been very good to date, but a lot of it's on paper.

Starting point is 00:36:02 And I began investing around 2008, 2009. I was like, okay, so if we flash forward, that's about six years. Many of these bets, and the jury's not out until the final outcome. Until the wire transfer comes in. Until the wire transfer comes in. And that final outcome for many of the startups that you bet on will take seven to 12 years. So looking at that timeline, I thought to myself, well, I've placed between 50 and 70 bets. I'm not yet convinced that I'm good at this. So why would I commit to doing this full time if I'm not yet fully satisfied that I am good at this? Or that things are sufficiently influenced by elements under my control that I can help steer outcomes. Yeah.

Starting point is 00:36:50 Right? You can be the best at picking the initial horses, but by the end of the race, if they're falling apart, it doesn't make a difference. So these were all questions I thought about. And that, in addition to many other things, a very close friend of mine asking me to please not stop writing. Yeah. This is Kamal. Kamal Ravikant, great guy. Given the feedback that he'd seen at events with readers of mine, he said, you'll never have that impact investing.

Starting point is 00:37:20 Right. So please don't stop writing and those all then coincided when i asked many of those questions which were uncomfortable because i've done very well financially in investing i've done better in investing by far than i have in writing and i've been certain fields are more lucrative than other fields so not all success is created equal yeah for sure and if you're if you're trying to get rich when people are like i'm just going to sell a few million copies of books, I'm like, God bless you, good luck. Because that is a really, it's difficult to make that math work. There are far easier ways to make money.

Starting point is 00:37:53 When I began to ask those questions, I realized that much of my being in the Bay Area was predicated on maintaining and building a competitive advantage in investing. So if you remove the investing, and you look at your surroundings with fresh eyes, you're like, well, wait a second. A lot of my best friends have left. So my social reasons for being here are few to none. Not none, but a few. If I remove the investing, my professional need to be here is non-existent. Sure.

Starting point is 00:38:26 So why am I here? Yeah. What do I like? What do I dislike? And a lot went into the decision, but led me to consider a number of different places, but predominantly Austin, which I'd wanted to move to right after college, just didn't get the job at Trilogy Software. And if you look at some of these decisions, they're almost all catalyzed by a breakdown of some type. Wearing out, some type of burnout. That happened with the four-hour chef leading to podcasting.

Starting point is 00:39:01 I was flamed out because I tried to do what should have been a three- or four-year project in a year or a year and a half, which was a suicide mission. And that extreme pain and burnout then led to test driving the podcast. Right. So a lot of my walking away at the top, so to speak, I would like to say is this grand philosophical insight

Starting point is 00:39:26 and balls of steel. You're not looking at the pile of chips and going, I have enough, let's walk away. You're actually going, this is awful and miserable. It's often both. Yes, right. But it starts with, this is awful and miserable. Right. It's sort of the breakdown equals breakthrough, I'm borrowing that from someone that is catalyzed by wearing out.

Starting point is 00:39:48 And I suppose where I've been fortunate or made some good decisions is instead of just plowing through that, sometimes it's physically impossible. I will say I have enough chips where I don't need to race into the next decision. Let me take some time to journal, journal, journal, journal. I do a lot of journaling, asking questions. I don't find my thinking to be clear at all unless I'm writing. I think Kevin Kelly was the one who said this to me, amazing guy, that he doesn't write to put his ideas down, he writes to think. He writes as a means of thinking. And in doing that, I then have

Starting point is 00:40:28 looked at options like stopping all angel investing. I like to ask these absurd questions. What if I left the Bay Area entirely, moved to Austin, Texas? And I think that another reason I've been comfortable pulling the trigger on a lot of these things, trying the podcast, is that I view them all as, and I don't know why it seems, I don't know why I find this so easy, but a lot of people find it hard. I'm not sure why that is. I think it's practice predominantly. Like, what would a meaningful but reversible experiment look like? That's it. Right.

Starting point is 00:41:06 Okay, with the podcast I committed to, I think it was six episodes. Yeah. And if I don't like it, I can walk. That's it. And with Austin, it's like you can always, I can always move back to the Bay Area if my realization is, oh my God, I didn't realize how much I loved these things I now miss. I can always move back. It's completely reversible. I think it's a great, because I remember I was asking you recently for some advice on something

Starting point is 00:41:29 that was like sort of a big purchase. It would be a big lifestyle transition. And you're like, well, how else are you going to find out if you want to do it or not? And you said, like, why don't you just commit to doing it for two years? And that's totally right. Because I remember when I dropped out of college, I was like, I'm dropping out of college college this is the biggest decision i've ever made in my life i remember i went to someone they're like you know you can go back right and it like it didn't even occur like even when i went to drop out i was like i'm here to drop out and they're like you there's not a form for that there's a take a semester off form you know but we think these lifestyle decisions are irrevocable and life-altering. And really, they can start very small.

Starting point is 00:42:09 They can start really small. I want to just highlight something you just said, which I think gets missed oftentimes in the romanticizing about dropping out of college that for many of the folks who are like the name brand titans who have who have adopted dropping out of college as one of their favorite stories and drums to beat if you have the the zuckerbergs the teals or whoever might be although teal is not a great example of dropping out himself but yeah you talk about these incredible icons of entrepreneurship who dropped out of school. It's really important to realize

Starting point is 00:42:52 that when you drop out of Harvard or Stanford, those administrations effectively say, come back anytime you want. Yeah. And that is a really important sort of footnote that people need to be. Yeah, although what I would add to that is I actually think the Zuckerbergs and the Gates are proof of the experimenting thing, right? Because I hear from people who want to drop out of college all the time.

Starting point is 00:43:15 They're like, I'd like to be an entrepreneur. I want to drop out of college. Mark Zuckerberg left college because Facebook was successful, right? He wasn't dropping out of college to then go start the Facebook. And so you can do the thing now and then if it's working, you can transition away. You can decide to go, hey, what would it look like

Starting point is 00:43:34 if I committed full-time to this for six months? What would come of that? And I think it's not like you'd never been to Austin before and you sold everything you own and you were like, I'm gonna see if I think it's not like you've never been to Austin before and you sold everything you you own and you were like I'm gonna see if I like it like you you can experiment you you dip your toe in these things in a bunch of different ways and then yeah you are jumping off a cliff but there's also an exit strategy yeah I I almost never burn the ships yeah I can't think of offhand a single example of me burning the ships and throwing caution to the wind and just leaping into the unknown.

Starting point is 00:44:07 That's just not how I do things. It's also because you don't need to do them. I think you don't need to do that. And by you, I think that means most people. Most people should not sort of jump headfirst into the shallow end and hope that they figure it out. I think that's a terrible idea. And if you look at some of the entrepreneurs who are thought of as these swashbuckling risk takers, Richard Branson, Sir Richard Branson, I've had on the podcast, as one example, they're actually, when you peek under the hood and start looking at the details,

Starting point is 00:44:40 they are better called experts in risk mitigation and capping the downside. He figured out how to lease planes, I think from Boeing, might have been Airbus, for Virgin Atlantic. Yeah. And set up a structure such that the financial risks usually associated with airlines were dramatically mitigated. Yeah. And he made a lot of exciting, unusual unusual bets most of which were survivable bets yeah right yeah jeff bezos says i don't believe in bet the company bets yeah he's like i want to be constantly taking risks small risks that are survivable i don't want the if this doesn't work

Starting point is 00:45:22 we go out of business he's like you've waited too long if you have to take those risks. Yeah. And as you mentioned with Austin, I mean, I've been to Austin 15 times. Yeah. I had spent increasingly long periods of time here each trip to South by Southwest. So I had already done more than dip my toe in the water. And it was really a question of whether I would enjoy living here. I knew I enjoyed being here for short periods of time.

Starting point is 00:45:47 Would I enjoy living here, which is a whole separate question. And there are ways to test. So I think my comfort with walking away at the top is a result of a high degree of comfort with and a large amount of practice in thinking about my life as a series of experiments yeah and it's it's also just being a student of recent history right look at dave chappelle he's crazy he walked away from 50 million and then he comes back and he does i don't know what the numbers are exactly what 100 million dollars with netflix yeah dave chapelle's fine yeah sure and uh people who really focus on being good at their craft can almost always come back uh no one no one i can't remember who said this this was in tribe

Starting point is 00:46:43 mentors but someone said you know if will smith doesn't do a movie for two years, people aren't like, whatever happened to Will Smith? Will Smith can take all the time he wants. And I think that underscores the importance of just focusing on being as good as possible at your craft. Yeah, that's the Cal Newport thing. Like, if you're so good, they can't ignore you. You get to dictate your terms. Yeah, yeah. And I am extremely risk-averse.

Starting point is 00:47:16 Risk defined as something with a high likelihood of an irreversible outcome. Yeah. The bet the farm. Yeah yeah so do you have any strategies for mitigating like what if you're thinking about doing something what do you look at to sort of separate good risk and bad risk good risk for me has a few characteristics two of the key characteristics would be high, high 90 plus percent likelihood of developing or deepening skills that will transfer to other things. Okay.

Starting point is 00:47:54 Whether now or in the future, even if this project fails. Another characteristic of good risk would be developing relationships that can transcend this project, even if it fails. And this is borrowing from Scott Adams quite a bit, the creator of Dilbert, who talks a lot about this type of thing. How to win even if a project fails. Another characteristic of good stress would be something that will help me to develop attributes or emotional resilience or to take things less seriously, which I think often go together. To try something that is scary to me or to most people that I can demystify in such a way that it's less intimidating. Yeah. The podcasting and doing six episodes is a great example.

Starting point is 00:48:44 Yeah. The podcasting and doing six episodes is a great example. Yeah. Because in the beginning, the idea of podcasting in my head was having this big studio and all this equipment and it's this American life with a staff of 40 people. And no, it's not. After doing six episodes, it's like, oh, all right. Actually, I'm not scared by audio at all. Because these mics, these cables, and the recorder that's on this chair

Starting point is 00:49:03 are like 500 bucks and you're locked and loaded. And the editing is actually pretty straightforward. So those are three characters of good risk. And then bad risk, I think, is largely a function of allowing unknowns that don't need to be unknowns. And so I do a lot of homework for many of my bets. If I'm looking at, say, Austin, I want to understand what the landscape, political, legal, and so on, looks like in Austin.

Starting point is 00:49:37 I want to look at population growth. I want to look at employment growth. I want to look at median home costs and how prices are moving, not just in Austin, but compared to my other options on the table. So the opportunity cost of the decision. It's a relative decision. It's not an absolute decision.

Starting point is 00:49:59 And I'm also going to look at, let's say if I stay in San Francisco, what are the risks of the status quo? What are the knowns that I dislike? And then what are the possible changes that I might dislike? So not just looking at the potential upside and downside and pros and cons of the new option, but comparing it to the current option. That sounds so self-evident, but it is not common practice, right? Most people just assume, all right, this is my known, and I'm going to look at the risks and pros and cons of this new option. I'm always looking at relative. I'm looking at not just opportunity cost, but the sort of relative attractiveness, right? And that can apply to just about anything.

Starting point is 00:50:48 I mean, it can apply to startups, certainly. And in terms of bad risk, I do look at financial risk. I look at reputational risk. I look at legal liability risk. And I do more comprehensive risk assessment than I do opportunity assessment. In part because I want to look for asymmetric bets in the sense that if I know I can cap my downside, that there is little or I can manage or completely eliminate reputation on legal risk by asking for, let's say, an indemnity clause and having a written record of what we agree my responsibilities will or will not be, and I'm putting in $50,000. Yeah.

Starting point is 00:51:48 In a sense, if I can control my time that is allocated to this, my max downside risk is 50%. Right. But if I'm investing in software as a service company. $50,000. Sorry, $50,000. If, though, I'm investing in a sector, in a vertical, in a type of company, like software

Starting point is 00:52:05 as a service or whatever that has comparables which show 100x returns, 1000x returns, I'll take that bet all day long. If the team and so on give it a reasonable likelihood of success, that is a great asymmetric bet. I think you can do that outside of investing in startups. I think investing helps to hone the questions you ask and the types of lens through which you look at things and how you might consider arbitrage and so on. But Austin, for me, it's a very simple bet where it's easy to cap the downside. It seems to me that's the main strategy in your life is capping downside.

Starting point is 00:52:54 So it's like, okay, you put $50,000 in the startup. The most you can lose is $50,000. You spend $500,000 on a real estate investment. You're responsible for the cost of maintaining the property. It's a totally different. And I think that explains your experiment thing. So it's not, I'm starting a podcast. Now I have to have a podcast forever.

Starting point is 00:53:16 You're thinking, I'm committing to six. So the most, if I don't like it, the most I have to do is six episodes of something I don't like. Do you know what I mean? You're capping so it's not endless amounts of losses, whether that's time, resources, happiness, money. Yeah. And I always try to cultivate walkaway power with my own projects. How do you do that? I'll explain or try to explain why I think it's important first.

Starting point is 00:53:54 If I feel like I have to do something, you lose your optionality. Yeah. And furthermore, you begin to make decisions out of fear or guilt which in my experience turn out almost always turn out poorly yeah similar if you're making decisions out of prestige can turn out very poorly I think I borrowed that from Maria Popova and what she said once on the pot on the podcast but cultivating walk away power is a function for me of a revisiting how little you actually need yeah frequently yeah this is seneca yeah seneca not timor's paupers huts but you know i will set aside a certain number of days each month or whatever it is to get by with the scantest.

Starting point is 00:54:47 Scantest or scantiest? I always mess that up. A fair. But practicing periods of poverty or... It's like being okay with a rock bottom. Yeah, making do. I just did this last week i'm making do for a while with just like instant coffee and like oatmeal in a bag that you cook with boiling water yeah and everything's great and granted it's different when you do it for an extended period of time it's different if that's your only option but nonetheless constantly revisiting and confirming how little is actually needed is number one. Number two is doing fear setting, this exercise that I talk quite a lot about,

Starting point is 00:55:33 which is, of course, borrowed directly from stoicism and cognitive behavioral therapy, which is also largely based on stoic, of what is the term in Latin? It is meditatio. Oh, premeditatio malorum. Yeah, meditatio malorum. Meditating on the possible evils or risks. So I have a written format for your setting. People can check out tim.blog forward slash TED

Starting point is 00:56:03 if you want to see what that looks like. It's all free. I do that routinely. So we're recording this in January, 2020. And I did a lot of fear setting around. Us talking, how poorly this could go. How poorly this conversation with Ryan could go and how I would possibly repair the incredible reputational damage around stopping just about everything.

Starting point is 00:56:25 So even though I'm not seriously considering, nor do I feel compelled to say stop, stopping the podcast, I would write down like, stop the podcast, question mark. What if I stop this? What if I stopped all involvement with real estate? What if I stopped all travel? What if I stopped? And now I will go through the thought experiment of what if i stopped all travel sure what if i stopped and now i will go through the thought experiment of what if i completely stopped these various things categorically and when you run

Starting point is 00:56:55 through the kind of so what so what so what so what yeah each of those ultimately realize you're going to be fucking fine with all of them. And to that extent, I think that making good decisions is often negotiating with yourself. And that the person you want to have win that negotiation, and this is advice I got a long time ago, is the person who cares the least. And that's not a value judgment. If you have two people negotiating against each other and one feels like they have to do the deal and the other person has 20 different BATNAs, best alternative to negotiated agreement,

Starting point is 00:57:43 and they don't give two shits whether the deal happens or not, or at the very least, they're very comfortable walking away. He or she who cares the least wins. Yeah. And I like to cultivate the side of me that can see how a lot of the glossy veneer aspects of life add at the end of the day to the core of what you need to feel content on a regular basis. So that might be a lot of word salad at once, but those are at least some of the ways that I think about it. No, I think that ties into,

Starting point is 00:58:22 we were just talking about the Stokes. Marcus really says this thing. He says, like, ask yourself at every moment, is this necessary? Like, what you're thinking, what you're doing, what you're desiring, is this necessary? And that seems, you used to have a sign in your house that said, like, simplify.

Starting point is 00:58:37 Still have it. Yeah, that seems like you guys are in alignment. You're like, do I need this? Do I want this? What would happen if I didn't have it? Why does everyone else want it? It seems like you're constantly questioning that i am uh or try to do it at regular intervals i mean i get caught up in the slipstream and start swimming against the riptide all the time i mean i get sucked into stuff all the time. I mean, I get sucked into stuff all the time. But I do very frequently take plane rides

Starting point is 00:59:11 and so on to journal. And to also try to identify, this is relatively new, I mean, in the last few years, but especially crossing 2020 and looking at not just 2019, but the last decade yeah and the better decisions that i had made and the poorer decisions and that i'd made which is which are different from

Starting point is 00:59:37 good and bad outcomes yeah there's like right but just the so where I made mistakes and decision-making and some of the sort of catastrophes and things that really caused me a lot of angst and upset one of the corollaries is I to the bad decisions is that or correlations rather is that I wasn't paying attention to energetic management or like energy management and I'll explain what I mean by that so it's managing your own energy yeah it's pretty simple I mean as I get older I'm still feel like I'm in good shape yeah but if I don't sleep well for two or three nights, life is not good generally. And that's a really simple example. But the point being, when I'm considering doing a project, partnering with someone, embarking on some type of creative endeavor,

Starting point is 01:00:43 the question that I'm trying to ask myself now is, over the intermediate or long term, which to me could be, you know, three months. Will this give me more energy or take away or deplete me of more energy? Sure. So it's not like the hell yes or hell no. It's like, what does this do to my energy levels? Yeah, which are closely related. But some of the things that give me a lot of energy are not necessarily a hell yes.

Starting point is 01:01:17 They're a yes, like swimming regularly. This is a great town for that. It is a great town for that, yeah. Yeah, you love Barton Springs. It's a great location. There are a lot of pools here. So swimming regularly, I always feel better, and I always feel more energized. I feel more emotionally resilient after swimming. And it's not a hell yes, like for some people going to Burning Man for the first time or something.

Starting point is 01:01:42 Right. It's not that volume. It's not like chocolate cake hell yes. No, it's not that volume. It's not like chocolate cake, hell yes. No, it's not that volume of like jump up and down on the table. Hell yes. But it is a great investment for building up energy reserves. Yeah. And so I've tried to make more and more decisions keeping that in mind.

Starting point is 01:02:04 Yeah. And I've turned down a lot of what on paper would look like fantastic opportunities because it will involve dealing with a huge bureaucracy which i know is going to drain my batteries and historically has always drained my batteries and it's like you know it's it's it is on paper a great opportunity but this is going to take 10 times longer yeah than it's spec'd out to take. And it's going to be draining. And I would much rather do something smaller that doesn't have that effect on my energy,

Starting point is 01:02:32 even though one could argue that this would be better for my career, whatever the hell that happens to be. I still don't know what that would be. I think a lot of people, you were talking about the difference between good and bad decisions is not the same as good or bad outcomes. And so I think a lot of people make decisions, and I do this, but I have to counteract it. But we go like, is this going to make me more or less money? Is this going to make me more or less famous? Is this going to make me more or less successful? Is this going to make me more or less interesting?

Starting point is 01:03:00 We think about the outcomes. And often that outcome is very far in the future and very much the decision isn't like if you do this, you are guaranteed X. Or if you do this, you're guaranteed X. It's like, hey, if you continue to do this over and over again, you might get this thing in 20 years. And I think one of the things I took from the four-hour work week and that I've gotten from you regularly is you tend to think more about quality of life right now. So don't work a crappy job that you hate so in 50 years you can retire and go to the beach. Think about what decisions you can make now that give you the access to the beach in the intermediate or short term. So I tend to think more like… As an experiment, right?

Starting point is 01:03:45 Yes. Specifically. Yes. Because you may get to the end of the line and be like, oh shit, I actually don't like sailing. Totally. And this was my made up dream for 50 years for which I sacrificed all these other things.

Starting point is 01:03:55 Yeah, so I think it's like, is this giving me day to day what I like more or less? You know, so that's my version of the energy thing. It's like, am I having the time and the life that i want not am i doing this so maybe i get that in the future and it seems like as a person who popularizes lifestyle design that's kind of your core message it's like are you designing a life you actually like living in that is that is, I think, a huge piece of it. And if we wanted to parse that out effectively be a contrasting sort of philosophical lens through which to look at career and personal development. development that is juxtaposed with the kind of slave, save, retire, I am going to cash in my chips in 20, 30, 40 years that will then redeem this period of doing many things that I disliked doing.

Starting point is 01:05:17 Which is not to say you're always going to enjoy doing everything. I don't know many people who love doing their taxes. There are things that you need to do, but outside... No one gets exactly what they want when they're 20 years old. You have to earn and build and invest. There is a period of testing that goes on to determine where you are particularly adept. Looking at... We don't have to do a rehash of the book,

Starting point is 01:05:48 but suffice to say, there are ways that you can test and should test the hypothesis that in X period of time, when I do Y, it is going to give me Z amount of pleasure that will make up for these decisions I'm making in the interim. That is a theory that is contingent on many things being accurate. And in my experience, effective lifestyle design is effective testing and awareness. Investing is, for me at least, has been effective testing and developing keen awareness of things that most people don't pay attention to or a lot of people don't pay attention to. So if we're looking at, for instance, living in New York City versus living in Austin, someone might say, well, I'm just going to live here for another 10 years. I'm going to have these following promotions and my investment banking job. And then I'm going to move to Hudson Valley. I'm going to move to Santa Barbara. I'm going to move to and then live the good life. Sure you will. Right. Yeah. So if that is your life plan, like let's spend some time developing experiments to prove or disprove that before you dedicate the next 20 years to it. But people will very often spend more time planning their Memorial Day weekend than they will specking out tests.

Starting point is 01:07:19 So if you look at, so A, is there anything in your historical record to suggest that you will be able to walk away from something like that? Right. Anything. Yeah. If you are type A, right? Yeah. And by definition, in that circumstance, you're probably type A. Yeah.

Starting point is 01:07:36 And there are many, many, many, many faulty assumptions yeah so I think that I I am very very accepting of the fact that there are many things I don't know and there are many things that I take for granted and there are many things that I don't see yeah therefore I spend a lot of my time developing experiments. And that's my constant framework. Like, how can I be sure that I know X? Yeah. Which relates to, in 2015, walking away from startup investing.

Starting point is 01:08:16 So I was like, all right, if I look at the track record of these various companies, not only in my portfolio but others, for the biggest wins, it's taking, if we're looking at, say, Uber, etc., it's taking 7 to 12 years to come to fruition. And your final tally is not known until you've liquidated all of your holdings effectively. I mean, it's a little more complicated than that, but not by much. and also in exits, I could convince myself that I am good at this, and people tell me I'm good at this, that remains to be seen. Yeah. And so I stopped. And the larger assumption,

Starting point is 01:08:57 just because you're good at something does not mean you have to keep doing it for the rest of your life. Yeah. There are many things I'm good at that I shouldn't do at all. Yeah. And it's challenging for anyone, myself included, to shift gears.

Starting point is 01:09:13 If you're good at something, being rewarded for something, and yet you have this creeping dread that you no longer want to do it, that is a challenging situation for, I think, just about anyone and certainly has been challenging for me. But the parachute, right, the safety net is realizing that for almost anything, you can leave and come back.

Starting point is 01:09:41 Yeah. Almost anything. And I'm sure there are exceptions, but if we're talking about businesses and professional capacities and careers, if you are really good, that's a big... That's the ultimate leverage. That is a huge hurdle that you need to be able to pass. But if you are really good and dedicated to your craft or crafts, it could be a combination of unusual crafts, right? Right. You might be a quant who's also really good at writing and then you have a newsletter. Sure.

Starting point is 01:10:16 It could be an unusual combination of traits like Warren Buffett and public speaking and writing or Jeff Bezos and writing, entrepreneurship, et cetera. You can always come back. Right. Right. So I try to keep that in mind when making a lot of my decisions. You know what's interesting? It's like you're taking it all very seriously, but then you're also not taking it that serious. So I was thinking, because we were talking about the Stokes more,

Starting point is 01:10:41 one of the things that sort of weaves its way through, I think, the thinking you're giving. And I know I gave you one of these. But the memento more. One of the reasons you shouldn't do the thing for the rest of your life just because you're good at it is that you only get one life. And one of the reasons I think you're always questioning. It seems like part of your fear setting thing is like, what if I die? Does any of this matter?

Starting point is 01:11:03 Do you know what I mean? Yeah, the costs of inaction. Yeah. I think that thinking very carefully about the costs of inaction and telescoping out 6 months, 12 months, 18 months, what effect does continuing to do what you do have on you and your loved ones from a financial emotional physical perspective right yeah and uh i think about death all the time and it's not a morbid sullen exercise

Starting point is 01:11:37 for me it's this becomes easier the older you get because friends start dying, family members die, and you realize this is not an indefinite lease. Yes. Like you have... Or that it is a lease. You don't own it. Yeah, it is a lease. Yes. And that having the, I don't want to call it time pressure,

Starting point is 01:12:03 but awareness of that impermanence, for me, I find, this might sound strange, but greatly encouraging because it drives a sense of urgency. Yeah. Or at least time sensitivity to a lot of my decisions.

Starting point is 01:12:22 And so that's on one hand, sort of prizing this fleeting, non-renewable resource that is time and realizing that it doesn't matter how much money you're willing to pay on your deathbed, you're not going to be able to buy back more time. Right. And then simultaneously, I guess meditating is the best way to put it, or contemplating how little a lot of this matters or all of it matters. In so much as Naval Ravikant once said to me, he's like, yeah, we're just a bunch of monkeys on a spinning rock. And spending time, this is going to sound so highfalutin, but whatever, reading about the cosmos or contemplating as, I believe it was Ed Cook, an incredible memory competitive champion and entrepreneur, memorizes his company, M-E-M-R-I-S-E, and Coach, also a writer, had said to me, and BJ Miller,

Starting point is 01:13:30 who's a hospice care physician, I think did something very similar, but they would look at, say, the stars and imagine that it's possible, and I'm not an astrophysicist, so maybe this isn't possible, but that it's possible that the star you are seeing is in fact light that is hitting your eye from a star that no longer exists. Yeah, right. And to just sort of contemplate that when you're freaking out

Starting point is 01:13:56 because you have some problem with Amex, or there's some disagreement and it's like somebody bad-mouthed you at work or whatever it is. Right. Okay. Number one or number two on the New York Times bestseller list or all the things that we... Who cares? Yes.

Starting point is 01:14:15 All dust. Yes. As our friend Marcus would say. Yes. Like all dust. Nobody gives a shit. Right. Not even you in the future will give a shit.

Starting point is 01:14:24 Yeah. It's all going to be just completely irrelevant. And so holding those two in my mind has been a practice. And I do think about death a lot and there was a person featured in I think it was Tribe Mentors Muneeb Ali who's involved very heavily involved with cryptocurrency

Starting point is 01:14:54 very very smart guy maybe better put blockchain very smart guy and it's funny to me how certain things stick and certain things don't stick. Or certain things have like a time release. So I read this and I was like, oh, that's interesting.

Starting point is 01:15:10 And then months later it sort of resurfaced and I've thought about it a lot since, which was he will routinely ask himself when he's overwhelmed or feeling scattered, how much would I pay to relive this experience like 20 years from now 30 years from now 40 years from now and I'm paraphrasing so that's not not not perfectly stated but and I think about that where I'll be if I think about the experiences that I would pay the most for and I'm being honest with myself, it's not the professional successes or the glamour shots. It's usually something very simple.

Starting point is 01:15:52 It's the moments of stillness and quiet and peace and relationships. Waking up in bed with my girlfriend on a beautiful sunny day and patting the bed and having my dog jump up and having a little snuggle fest it's very it sounds so cheesy like the 20 year old tim would just be vomiting all over himself right now but nonetheless 20 year old tim is pretty miserable fuck so uh i feel like

Starting point is 01:16:16 i've improved on that front and asking yourself like all right if i were 80 and like molly has long since passed away maybe my wife has passed away how much would i pay for that yeah right and that really to me is part and parcel of the valuing of time these slivers of experience as more valuable than making a speculative decision about earning more in the future based on doing something that takes you away from those people. Right. Or agreeing to something because you might get some honor or, you know. I'll just add one more thing, which is I really think that even if you keep all your money in a mattress, studying good investors is worth a lot.

Starting point is 01:17:11 Not necessarily in financial return, but in temporal return, in how you think about time. Because humans overall are very sloppy. I'm no mathematician, so I'll put myself in the same category. When it comes to thinking about probabilities, probabilistic thinking is not, it's not a strong suit for humans. And so you might hear like, oh my God, there's a room of 300 people

Starting point is 01:17:40 and these two people have the same birthday. That's crazy. But mathematically speaking, it's not that crazy right and in fact at some point it becomes totally expected right and similarly developing a basic sort of mathematical literacy with respect to investing so i think most people watching and listening to this will have as i did i mean i stopped taking math in high school because i had one bad math teacher, even though I was good at it. I became totally turned off. My brother went on to get a PhD in stats. And it was the same year. He had a good math teacher and I had one who was just a ball buster. And you can see how we split in different directions. But I have a

Starting point is 01:18:16 deep-seated insecurity when it comes to math. Nonetheless, studying, investing has helped me to develop my understanding of certain concepts like expected value. So if you think that you are going to, you could make $100,000 or $1 million or $10,000 at Y point in time, is making that decision in your mind actually worth 10, 100,000 or whatever it might be? Yeah. Well, it depends a lot on the probability of that happening. Right.

Starting point is 01:18:53 And then you can do some basic multiplication and be like, all right, actually the expected value of that, given that it's low probability or 50% or 30% is instead of $100,000, it's actually worth $25,000. That could very, very deeply influence how you make that decision about how you're gonna spend your time over the next six to 12 months. Because if there's a sure bet, it's a $50,000 return, but it's 80, 90% likely to happen.

Starting point is 01:19:19 It's worth more. It's worth more, right? If you're thinking about it in a structured way. And there are some really fun books on investing It's worth more. It's worth more, right? If you're thinking about it in a structured way. And there are some really fun books on investing that don't necessarily touch on this exactly. One is called More Money Than God. It's about hedge fund investors. It's a super fun book.

Starting point is 01:19:36 It's kind of like Liar's Poker, but instead of purely bonds, it's all sorts of different characters and types of investing. There are other books. I think there's one called How to Measure Anything, which is worth taking a look at. That was recommended by co-founder of ZocDoc named Nick Ganju, who is a fantastic teacher, really, really good teacher. He's taught me a lot about music and math. Math is too scary. Just like how to think probabilistically. Because life is probabilities.

Starting point is 01:20:09 And whenever, for instance, and I'm dragging myself into the deep end a little bit here because I'm not a scientist, but if you look at science and studies, this is another reason to become sort of probabilistically literate, is you'll be better able to separate fact from fiction and fact from hyperbole in medicine and science. People get so confused about these things and people end up dying and making bad decisions or choosing quacky doctors without this basic literacy. There's a great book called Bad Science by Ben Goldacre that I recommend to everybody. I excerpted some of those chapters in the appendix of The 4-Hour Body because I think it's so important.

Starting point is 01:20:58 But suffice to say, if someone says, these studies prove X, it's not really true. They suggest at a high probability. They suggest for a very small sample size, it had a slightly greater than average probability that X. And it could be an incredibly strong signal, but it is not 100% certainty. It might never have been replicated. It might never have been replicated it might never have been replicated there could be experimenter bias who knows how tight the design was and it changes how you relate to the world and decisions and opportunities and risks when you

Starting point is 01:21:37 start thinking in terms of probabilities right because to remove all risk is a fool's errand. I spent a lot of time trying to do that. And chasing that tail end of the last, let's just call it 10% of risk, you could spend all your time, 24 hours a day, every day trying to do that. And you would still not succeed. You'd just have to lock yourself in solitary confinement in the box. And it would be no life worth living. But this has been a real game changer for me. Even though I don't do, I mean, I invest.

Starting point is 01:22:10 Anyone who's alive invests. I think you're investing time, energy, capital. You're choosing where to allocate resources. But I read all these books on investing. Or Think Twice is another one that's good, related to cognitive biases. Not because I'm playing the stock market at all. That's not why I'm reading these books.

Starting point is 01:22:36 I'm reading it because it helps me to think in a more structured way about good decision making. Yeah, I want to come back to the studying thing because I had a question for you. But when we were talking about sort of happiness, money, young, old, Sepp Kampar, who we both know. Yeah, brilliant guy. He did this massive study where he scraped all these blog posts and social media posts about what people were saying.

Starting point is 01:23:06 I think the book is I Feel Fine. This is like the result of the findings. But he was talking about how young people, when they say like I feel happy, it tends to be followed with statements about accomplishments or activity. And as you get older, the statements drift steadily towards feelings of contentment or connectedness.

Starting point is 01:23:28 And so we can make a lot of decisions. It's like we know objectively that's where we're going to end up. That's what we're going to care about. But then we spend most of our lives focusing on piling up accomplishments. Do you know what I mean? Yeah. And sort of knowing, I think that idea of thinking about what you're going to care about if you are lucky enough to get old is really important because it puts the things

Starting point is 01:23:51 that feel important in perspective. Yeah, Sepp's an amazing computer scientist and just a sweet heart of a guy. Totally. heart of it. And this observation that you just made, that in younger years, let's just call it 20s and maybe 30s or early 30s, I am happy, I'm doing great because, and then accomplishment versus the contrast with connectedness and so on when older raises a lot of interesting questions for me right so is it that independent of how well someone does professionally that that shift exists yeah or is it that those people who are being polled happen to be at say stanford where sep has spent a lot of time so those people who are being polled happen to be at, say, Stanford

Starting point is 01:24:45 where Seb has spent a lot of time? No, people aren't being polled. This is unsolicited statements that you make on social media. Okay, I got it. So that answers that. To me, it's important to me at least to immediately not be a cynic but to ask a lot

Starting point is 01:25:08 of questions so i understand the nature of what is being implied right yeah because could it be that the people who experience or value connectedness in later years sort of paid their dues cut their teeth yeah and therefore they're like, all right, I'm on my second home. I have checked off all these wrongs on Maslow's hierarchy of needs. Great, now I can focus on self-actualization. Or does it happen independently? I think if I had to place a bet, I would imagine that it probably happens somewhat independently

Starting point is 01:25:44 as you become more aware of your mortality. Yes, I think that's what it is. But this is another facet that I think underscores how beneficial it is to study good investors, or good scientists. But I think that investing has more sex appeal for a lot of people. The distinction between correlation and causation yeah right and or is there a third is it possible there's a third or fourth factor yeah that could be causal or at least highly correlated right so you might see an observational study of some type where women who do yoga between the ages of this and this report a higher level of well-being and lower blood pressure. Therefore, the headline in some… Huffington Post.

Starting point is 01:26:38 Wherever, right? Therefore, yoga decreases blood pressure. Wait a second. Where was this done yeah it's like oh san diego okay what's the median household income okay what else are they doing oh they're seeing they have ppo instead of hmo and they're seeing some of the best doctors in the country oh okay all right and you begin to realize uh how tricky it can be to establish a causation, right? Yeah.

Starting point is 01:27:06 But I don't find, at least the more I dig into this stuff, I find that more enriching and exciting than anything else. I know that it's frustrating because it means you can't rely on, say, most media reports of scientific findings or studies to be accurate and the claims that are extrapolated. But at the same time, to me, what it highlights is how much there is in plain sight that is really misunderstood. Yeah.

Starting point is 01:27:38 And that's exciting for me because to me, that spells opportunity. If it's possible, for instance, and there's some pretty good examples of this. I think that if you even look at, for instance, before we started recording, we were talking about the big short. If we look at some of these mortgage-backed securities, short bets that ended up producing these multi-billion dollar windfalls. Some of those positions were based on looking at publicly available data and drawing some pretty common sense conclusions. Right. It wasn't AI, proprietary AI

Starting point is 01:28:22 from the Chinese government that was cracking this code. It was looking at what's right in front of certain people and seeing something different and also asking a lot of questions about incentives. Right. Like if you ask a venture capitalist if things are going to turn south, they are highly, highly, highly, highly, highly subconsciously or consciously disincentivized from saying things are going to go south.

Starting point is 01:28:49 Unless they have a large bet that things are going to go south. Which they would have to have either outside of venture capital. Right, sure. It wouldn't be associated with their fund. Or they'd have to have some counter-cyclical startup bet, which they may or may not. Conversely, if you're looking at, say, hedge fund investors, I know that's a term that's fallen out of favor, but nonetheless, people who can place both long bets, we think this is going up or growing, and short bets, we think this is going down or decreasing in value. Their view of the world is going to be very different than what they're willing to talk about. Yeah. So I find it incredibly, both really exciting and entirely terrifying that there are so

Starting point is 01:29:34 many blind spots. Well, Tyler Cowen talks about this with the three-point revolution in the NBA. Like, three-pointer has always been worth more than two-pointers. Right. And so you can miss a higher percentage of them and still score more points. Right? So, you know, percentage making of a three-pointer is on average worth more than a field goal. Right? And it's like, literally, people were paid millions of dollars, billions of fans watched

Starting point is 01:30:03 this game, and no one was like, hey, why don't we shoot more three-pointers? And then somebody did it. And the entire game changes. Yeah. I wonder who that was. Like Steph Curry or someone comes in and just. But like that it was even, not just like within our lifetime. Like it was within the last half decade that the game fundamentally changed.

Starting point is 01:30:21 And it's not like they figured out the physics of shooting a three-pointer better like yeah just now there's incentives and so people shoot more three-pointers and they make more and that a game literally that millions of people watch just nobody noticed this thing right in front yeah yeah or like you look at certain inventions right wheels on luggage like yeah for god's sake yeah right how long does that long does that take? And it's sitting there right in plain sight. Yeah. And I think there are still practically infinite number of opportunities like that. And for me, at least, it all that has been developed at places like IDEO or Frog Design or these different product development industrial design firms, a lot of it's asking questions, right? Yeah.

Starting point is 01:31:14 And trying to not just test the assumptions but find the assumptions, identify the assumptions in something like grocery cart design. What have we just completely taken for granted because this is the way it is and this is the way it's always been? And I find that really exciting when it comes to, and I like to try to ask a lot of those questions. There's a great doc documentary called objectified yeah which is about a lot of this uh and then i saw it a long time ago made by the same filmmakers i believe who did a film called helvetica about a good documentary yes such a great doc that brings up a lot of this and when I see something that doesn't make sense or doesn't feel good, doesn't work well,

Starting point is 01:32:10 I like to ask a lot of questions and also combine that with studying incentives. Like, is there any reason besides a design blind spot that there weren't wheels on luggage earlier? Like, is there some? Is someone incentivized in such a way that would make that, like did that idea exist 30 years earlier but it never came to fruition? And if so, why might that be the case? Okay, let's do that as a thought exercise.

Starting point is 01:32:39 Yeah. And for instance, I remember whenber is a great example of this right i mean i was involved with with uber before it was called uber it was uber cab llc way back in the day in like 2008 yeah and uh we'll just refer to it as uber for simplicity was widely mocked i mean it was it was put on angel lists which is another company I'm involved with, angel.co if people want to check it out. It was offered to investors and turned down, I want to say by hundreds of investors

Starting point is 01:33:11 as ludicrous. the math behind some of the ridicule looked at the existing market for, I want to say, black sedan car services and limousines.

Starting point is 01:33:29 And in that analysis, in retrospect, we can see there are a bunch of false assumptions. Right. Right? They thought it was always going to be high priced. Yeah. Where many things start out being prototyped among the privileged. Yeah. Recycling.

Starting point is 01:33:44 Yeah. Another great example of that. But then with scale, prices go down. It also assumed a relatively fixed market size. It's like, here's the existing market of black sedan use. We only see X percent of single digit growth. Yeah. This is a shitty business

Starting point is 01:34:04 because they'll never capture more than Y percent. Missing the possibility and ultimately the reality, which was that ride-sharing would expand that market exponentially and create its own market. And then you look at, let's just say, incentives of media coverage. Yeah. At the time, and even more so now, it's very much in fashion to attack anything that seems like it's catering to the 1%. Right? Even though it's really critical to prototype with people who are price insensitive

Starting point is 01:34:49 in the early stages of a lot of product development because if you're making one-offs, they're going to be fucking expensive. And if you're testing things and it's very rough around the edges, you can have these rich people, exactly, subsidize the product development that will ultimately lead to mass adoption. So I find the whole thing just endlessly fascinating.

Starting point is 01:35:14 And I think it's also safe to assume that at almost any given point in time that almost everybody is getting it wrong. With many, many, many, many, many things. And that to me says that if you just have, because this is not an intrinsic capability that I have. This has been, if we're talking about it from an investment perspective or opportunity spotting perspective, it is absolutely something that I have honed over time. And there are many people much better than I am.

Starting point is 01:35:49 But when I've found questions I like, I borrow those questions and I put them into an Evernote notebook under investing. I have these questions. When people point out misperceptions to me and I'm like, holy shit, I totally missed that. How could I have missed that? I write those down. I'm like, wow. I completely, this never. How could I have missed that? I write those down. I'm like, wow. This never would have occurred to me now that they've said it. It's entirely self-evident.

Starting point is 01:36:11 How did I miss that? And why did they not miss it? I really think about these things. you can develop this very learnable skill of seeing things that other people don't see, which for me is mostly a byproduct of asking a lot of questions. Well, that actually ties into what I was going to talk to you about next. There's a quote in Ego's Enemy. I have a quote from Bismarck where he says any fool can learn by experience I prefer to learn by the experience

Starting point is 01:36:48 of others and it seems like so you're doing experiments you're doing trials but you're also it seems like that's one bucket of learning for you then the other bucket is like a network of smart people you ask lots of questions of and then the third one is like a network of smart people you ask lots of questions of.

Starting point is 01:37:05 And then the third one is like you read widely and deeply from different kinds of books, from history, from philosophy, from psychology. So you're not spending 30 years of your life learning a lesson you could have learned on a $3 used Amazon purchase. Oh yeah, I much prefer to not make my own mistakes if I can avoid it,

Starting point is 01:37:28 recognizing that, of course, I'm going to make all sorts of terrible mistakes. And to give an example of the second category and learning from other people and how I might approach that, we can talk about something we were discussing very briefly before we started recording, which is right now I've noticed and my team has noticed some kind of odd behavior

Starting point is 01:37:52 when it comes to email deliverability and open rates. And we have, by most measures, a large list, 1.5 million or something like that, for Five Bullet Friday and these various newsletters. And we have already looked on Google, we've already talked to some of the parties involved, but these parties have various incentives that may or may not be totally aligned with ours. Not to say they're in any way malicious or nefarious, it's just different companies,

Starting point is 01:38:22 different people, different parties in a different collaboration or transaction have different incentives. So I and my team have been putting together a draft email to send to people like yourself. It's really five or six people I know already who have large lists to ask a handful of questions. But if I simply email all of you with a handful of questions, it's a very one-sided interaction. I'm asking someone to take time out of their day to help me with nothing in return. So what we've done is underneath each question,

Starting point is 01:38:57 we are adding what we've tried. Here are the three things we've already tried to address this. Here are the results, but we're still looking for for more what have you done or what would you do right step one or question one question two question three question four and that could at some point turn into we were joking earlier the conversion cabal registered trademark am funnel, here we go. I'm not going to do that. But that could turn into some type of brain trust with a handful of people who then exchange best practices. Where everyone is currently, or most people, are very siloed. So they're all trying to solve similar problems and have similar aspirations, yet even though all the newsletters that I'm thinking of, which are owned by people like yourself and these other folks, they're all

Starting point is 01:39:52 non-competitive. They're all in different areas with different demographics. And it would make a lot of sense to have some information exchange. And that will start, the initial volley will be this email, right? Where I'll share a bunch of stuff, and we may or may not get replies. I hope we get replies. That would be an example of trying not to just make our own mistakes. No, I'm going tomorrow. I'm flying to Arizona, and I'm meeting with five or six authors who you know. We go to this house in Sedona.

Starting point is 01:40:21 They've all sold, each one of us has sold hundreds of thousands of books, best-selling authors, and we just shoot the shit about stuff that's going on. We ask each other questions. And you could even argue that some of us are competitive. I don't think books are competitive, but the point is why would we compete

Starting point is 01:40:37 where we don't need to compete? Let's compete on making great stuff. You know what I mean? That's what's been amazing for me with sports um watching these like coaches give book recommendations to each other you like you'd think they would be competitive but it's like actually they're getting the easy stuff out of the way and then on sunday they're competing yeah and so just i think people can be really precious with information when actually you're almost always better sharing

Starting point is 01:41:05 information. Yeah. And on top of that, I can very safely give my playbook for almost anything to thousands of people and almost no one's going to implement any of it. And that's not to say that prescriptive how-to stuff doesn't get used. It does. Particularly when it's simple, right? Like slow-carb diet for our body.

Starting point is 01:41:35 Hundreds of thousands of people, maybe millions, have used this diet successfully. It's simple. It's easy to follow. Everyone is following a diet, whether they choose to or not. Sure. But when it comes to say launching a book yeah right and i lay out this monstrous post because i got tired of answering these questions as one-offs right how to i think it's called how to publish a bestseller how to how to publish a best-selling book this year or something like that how to write a best-selling

Starting point is 01:42:02 book this year i can't remember the exact title. But it's this monster compilation post of like everything you can imagine related to writing, prepping, titling, publishing versus self-publishing, marketing, PR, all of it. Blurbs, you name it. Every stone is turned. And people don't do it yeah if they're just like no I want that I want the silver bullet easy answer like can I hire someone to do that for me yeah yeah it's like yeah no this is that I mean maybe

Starting point is 01:42:37 you can but like this is my blueprint right I've used it repeatedly it works but guess what you still have to write a fucking good book right and not to say my books are the best in the world they're not I mean I would like to see

Starting point is 01:42:49 I would like to think they're very useful but I'm not Tolstoy I recognize there are better writers out there nonetheless I

Starting point is 01:42:57 take the vast majority of energy and it goes into the writing yeah but man yeah it's it's uh it's pretty wild how how little adherence there is well to go to that last bucket maybe that's a place to wind up uh what do you think about reading like how do you find what you read what's your methodology

Starting point is 01:43:20 for breaking down books like do you where do you get the knowledge that saves you painful trial and error? I very rarely read anything that isn't recommended to me by either someone I know is very selective and snobby about book choice. Yeah. Like, say, Naval Ravkant or my brother. Yeah. There are certain people who already have such a tight filter that anything they read has passed a very high bar. Yeah.

Starting point is 01:43:59 And anything they recommend has passed an even higher bar. Yeah. That is one way I get books referred to me that I take seriously. Another would be triangulating multiple points of recommendation. And then very often what I'll do is let's just say I get a book recommended from people on social media or readers or listeners. And I will prompt recommendations quite often by asking for the best books on a certain topic. And perhaps a year ago or two years ago,

Starting point is 01:44:38 I was very interested in learning more about the contemporary art world. Not just the artists, but the gallerists and the entire industry, the market, the black box, all the craziness that goes into that. And this book called The $12 Million Stuffed Shark popped up repeatedly. I'm like, okay, let me take a look at that. And I looked at it, seemingly written by an economist. I go down then on Amazon, in this case, to the reviews. I don't read the one-star reviews because they're like, I thought this was an Instapot.

Starting point is 01:45:14 This is stupid. Mine came damaged in the mail. Yeah, or they clearly didn't read the description. They're like, this wasn't a novel at all. It's like, yeah, dummy, it's not a novel. So I don't read the one star. I don't read the, what is the highest, five stars? I don't read the five stars.

Starting point is 01:45:33 I will read the most helpful three and four star. Because I already have the gestalt. If the reviews are more than a few hundred reviews, I make the assumption that it is more or less reflective of the reality of the book. Amazon reviews can very easily be gamed on a smaller level, but most authors are not going to be motivated enough to do it over a long period of time. So I assume if there are hundreds of reviews or even 100 plus and I look at them and there are substantive reviews that the overall star ranking is a broad indicator of how much people

Starting point is 01:46:18 have liked the book. Then I look at the most helpful three and four star reviews because they will very often be, say, three paragraphs to two pages long, and they will really accurately lay out the structure of the book and the strengths and weaknesses. Sometimes they make you read the book better because sometimes it spoils what's in the book, but then you actually understand it when you're reading it. Yeah, absolutely. So I do that and if at that point I'm interested, I download it on Kindle.

Starting point is 01:46:53 I try to do almost all of my reading on Kindle, which gives me the ability to highlight very easily and then I can go to Notebook on Amazon or use any number of other services to grab those highlights and look at them on laptop put them into evernote whatever it might be but before i get there i will look at the most popular highlights i will also look at goodreads i like looking at goodreads for quotes from given books if you don't like if you don't love yeah somes for quotes from given books. If you don't like, if you don't love some of the quotes from the books, that's like hating the movie trailer and then going to see a three-hour movie.

Starting point is 01:47:30 You're not going to like the movie. So I look at Goodreads, and let's just say then I have the Kindle version. I will, I'll read two chapters, three chapters, and if I don't, if I'm not really grabbed, if I don't want to take a photograph of some of the highlights and send it to a friend, I will consider stopping reading.

Starting point is 01:47:52 Because life's too short? Life's too fucking short. Tim Urban of Wait But Why has so many great pieces, and one is called The Tail End, and he talks about the number of books he's likely to read in the rest of his life. And it's a shockingly, frighteningly low number. Small number, yeah. and one is called The Tail End, and he talks about the number of books he's likely to read in the rest of his life. And it's a shockingly, frighteningly low number. Small number, yeah.

Starting point is 01:48:08 So I don't have enough time left in my life if we're assuming I'm going to die. And I've looked at the death ages of my grandparents, great-grandparents, et cetera. Then I've isolated the males I've looked at. So there's a pretty decent chance I'll die somewhere between 80 and 85. I'm 43. There's not that much time left,

Starting point is 01:48:32 especially if you consider sort of cognitive decline and so on. So I've got, let's just call it, who knows, 20 to 30 years left of good book reading. You could also get hit by a bus. I could get hit by a bus. So all that is to say, I don't have enough time to even read the classics I know the titles of that I've heard of.

Starting point is 01:48:54 I don't have time for that. I don't have time to read all of those. So the idea that I would pick up a book and think to myself, this is pretty mediocre and dedicate a week to reading it is pure insanity. So I drop a lot of books. When I looked at, and I put up a blog post recently looking at everything I read in 2019, all the books and favorite articles.

Starting point is 01:49:17 And I included all the books I bought from Amazon and I ended up completing somewhere between 30 and 40 percent of all the books that already made the cut to the point that I bought them sure sure uh and some of those I simply just never got around to but a lot of them I I stopped I like the rule a hundred pages minus your age that's that's's the taste test? Yeah. That's when you quit. Oh, okay. So as you get older, you become more ruthless.

Starting point is 01:49:50 As you get younger, you have to give it, because you don't know what the fuck you're talking about. Yeah, yeah, yeah. I like that. I like that. Yeah. I like that. But no, I think people are, they're like, I paid for this.

Starting point is 01:49:59 That's the sunk cost fallacy. They're like, I paid for this. I should finish it. It's like, you hate this book, so you're going to give it hours of your life, weeks of your life, just to prove that you could finish a David Foster Wallace book? I mean, like, come on. Yeah. And I was just thinking one way you could maybe trick yourself into making better decisions with books

Starting point is 01:50:18 is to imagine that the book you're reading is someone you're having dinner with. Yeah. And it's like, would you really sign up for, like, five more dinners with this person? Right. If this is how you felt while you were reading someone you're having dinner with yeah and it's like would you really sign up for like five more dinners with this person right if this is how you felt while you're reading it sure no you wouldn't right and uh the call that you'd make up an excuse and you'd leave the dinner you're already at yeah yeah exactly so uh books are also a great way to procrastinate, sort of a socially validated way to procrastinate. So I try to be ruthlessly honest with myself about that. Interesting. I will, there are a lot of great books out there.

Starting point is 01:51:01 Yeah. I could spend all day every day reading great books. Yeah. And produce absolutely nothing of value yeah so i uh have increasingly tried to block out time i have less i would say less and less time i dedicate to reading and i'm going to be publishing a post this week which is a public pronounce, which helps with setting policies for saying no. Describing why I'm not going to read any new books in 2020. So anything that is published in 2020.

Starting point is 01:51:36 My general rule is I almost always go towards older books. Can I say one thing? So I'm going to put out that post also to hold myself accountable. Right. Right? Right. Because if I get caught then reading something new, it makes me look like a liar or a hypocrite,

Starting point is 01:51:53 and I use public... I don't want to do the book blurbs. Oh, I definitely won't want to do those and don't want to do those. So this is a single decision that makes, as Greg McKeown of Essentialism, which is a great book I recommend, would say... Not new anymore, so people can read it. Oh yeah, yeah, it's a fantastic book. Looking for the single decisions that remove hundreds of decisions, right? So not reading any books in 2020 removes a lot of decisions.

Starting point is 01:52:26 Someone says, oh my God, you should read this book. It's new. Sorry, I can't do it. It preserves so much of my cognitive decision-making bandwidth and energy for other things to make that one public. And for me, public is to a large audience, but in other areas of my life, I make public commitments to

Starting point is 01:52:47 one or two or three friends or to my girlfriend so that they can hold me accountable. Sure. And I find great value in that. If you're trying to guard against your lesser self, I find that really useful. No, and I think with, it's like, so the cost of a book is financial, primarily time, and then what you're going to put in your brain. I don't want to read things that are going to be subsequently or very quickly proven irrelevant or proven incorrect or out of fashion.

Starting point is 01:53:20 You'd be better off sitting down and reading Shakespeare's plays because that has not only had 500 years of cultural impact, but will probably have 500 more years of cultural impact. So I think looking at the half-life of information and deciding to consume information that's likely to remain true over time, it forces you to be both more general but also more timeless. Meanwhile, if you read a book about the first year of the Trump presidency,

Starting point is 01:53:50 or how many books, like a couple years ago, or a year or so ago, somebody wrote a book about Uber, and then the founder was fired shortly after the book came. It's like that book is, the guy who finished that book

Starting point is 01:54:02 wasted his time because it's already irrelevant by subsequent events. i think we have a newness bias that prevents us from accumulating wisdom where we could be talking about anything, right? We could be talking about human behavior, we could be talking about the rise and fall of nations that are kind of like the tectonic plates. Sure. I'm more interested in those because there's a bit more certainty and a higher degree of confidence

Starting point is 01:54:47 in identifying and understanding some of those elements, right? If they've been shown over and over again throughout history or proven or, I suppose, based on what I said earlier, shown to be very likely repeatedly in science. So this all makes me think of this quote by, I think I'm getting the name right, Donald Nuth, K-N-U-T-H, who was at, I want to say IBM. Might be IBM, but doesn't really matter. The point being he stopped using email at one point.

Starting point is 01:55:27 Yeah. Completely stopped. And he said, for people who want to stay on top of things, email is great. He's like, but I want to get to the bottom of things. And I've thought about that a lot. Yeah. Because keeping on top of things is a losing game. Yeah.

Starting point is 01:55:44 It's just... By definition. Yeah. New keeping on top of things is a losing game. Yeah. It's just... By definition. Yeah. New stuff's happening. It's a losing game, and there are people who are going to be more dedicated and obsessive with current affairs. I have no competitive advantage. I have no information advantage.

Starting point is 01:55:58 I actually have a lot of information advantage, but I have no desire or behavioral advantage with current events. And it also breeds sort of emotionally and physically a life driven by cortisol and FOMO and so on. myself enough, which I partially do through this public accountability, to focus on studying things that have endured, I just feel much better in life in general and I make better decisions. Yeah, look, they didn't have the news 250 years ago. Do you know what I mean? They did fine.

Starting point is 01:56:43 Yeah, yeah, yeah. They did fine. Yeah, they did just fine. So, oh man. Yeah, the news. Happy to miss the news. Yeah, of course, of course. I'd rather have truth than trivia.

Starting point is 01:56:57 Yeah. So Ryan, I suppose this is the time when we say goodbye. Yep. Tearful, tearful, stoic holiday goodbye. Yeah. Where can people find you online, learn more about you, and what would you like to tell people

Starting point is 01:57:11 about your current projects? Yeah, maybe check out Daily Stoic, which is a stoicism-inspired email each morning. Also at Daily Stoic on most platforms. And then I'm Ryan Holiday, pretty much any bookstore. Across the socials and across the bookstores. Yes.

Starting point is 01:57:29 Is there any, if people look at your selection of books and think to themselves, I don't know where to start. Yeah. Where would you suggest people start with your writing? It's a good question. I'd start with the obstacle is the way or stillness is the key. It's like if you're going through something tough, I'd start with the obstacle is the way or stillness is the key. It's like if you're going through something tough, I'd start with the obstacle is the way. If you're maybe dealing with some of the stuff we're talking about,

Starting point is 01:57:50 which is sort of life optimization, what do I want? How do I manage? Maybe I'd do stillness. All right. And there you have it, folks. Thank you, Ryan. Yeah, it was awesome. And as those listening probably know, this is Tim Ferriss signing off for now

Starting point is 01:58:06 thank you for listening and until next time experiment well experiment widely and test those assumptions hey guys this is Tim again just a few more things before you take off number one this is five bullet Friday do you want to get a short email from me and would you enjoy getting a short email from me every Friday that provides a little morsel of fun for the weekend? And Five Bullet Friday is a very short email where I share the coolest things I've found or that I've been pondering over the week. That could include favorite new albums that I've discovered. It could include gizmos and gadgets and all sorts of weird shit that I've somehow dug up in the world of the esoteric as I do. It could include favorite articles that I've read and that I've shared with my close friends, for instance. And it's very short. It's just a little tiny bite of goodness before you head off for the weekend. So if you want to receive that, check it out. Just go to 4hourworkweek.com.

Starting point is 01:59:06 That's 4hourworkweek.com all spelled out and just drop in your email and you will get the very next one. And if you sign up, I hope you enjoy it. This episode is brought to you by 99designs, the global creative platform that makes it easy for you to find and work with amazing graphic designers online.

Starting point is 01:59:24 Long-time listeners of this podcast know how much attention I pay to detail, how obsessively I approach nearly all elements of my work, because the small things often end up being the big things. So whether it's your logo, your business cards, website design, even your email templates, all of these visual elements tell your customers, tell your users who you are and what you're about. So I think it's worth sweating the details. I've been using 99designs for years now to ensure that many of my creative projects, whether big or small, are as cohesive, professional, and beautiful as possible.

Starting point is 01:59:54 I've worked on draft mock-ups of book covers. I've worked on all sorts of things. Most recently, I've been working with a designer at 99designs to update the illustrations and layouts for all of my downloadable ebooks. I've developed a really great working relationship with the designer who goes by the username Spoonlancer, and I intend to continue working with him to bring ideas to life one project at a time. I've also used 99designs for all sorts of high-end illustration for different books, like the Tao of Seneca. You can see a bunch of examples on my Instagram

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Starting point is 02:01:27 I certainly have had that experience multiple times. I've made a lot of mistakes. I am not eager to repeat any of them. So I try to do as much vetting as possible now on the front end. Today, with more qualified candidates than ever, but certainly more noise than ever, employers need a hiring solution that helps them find the right people for their businesses without wasting time, without wasting money. LinkedIn Jobs provides just that. LinkedIn Jobs screens candidates with the hard and soft skills that you specify that you're looking for, so you can quickly find and hire the right person. They also look beyond work skills,

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The Tim Ferriss Show - #410: Ryan Holiday — Turning the Tables

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The Tim Ferriss Show - #410: Ryan Holiday — Turning the Tables

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