Ryan Holiday Interviews Tim Ferriss | The Tim Ferriss Show

Ryan Holiday 0:00 [upbeat music]

Ryan Holiday 0:15 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, I..." Like me, like, I got a goat one day 'cause we saw it on Craigslist, and we just, like, went and got it. But that's not w- for the Tim Ferriss way. [laughs]

Tim Ferriss 0:34 Yeah.

Ryan Holiday 0:34 You were, like, you were ta- 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?

Tim Ferriss 0:41 Four and a half years ago.

Ryan Holiday 0:43 Okay.

Tim Ferriss 0:43 Maybe five.

Ryan Holiday 0:44 But, but it, it'd been a, an interesting pivot in your life. W- why do you think it, it impacted you so much?

Tim Ferriss 0:54 Uh, I think that there are a few aspects to it. Number one is caring for a puppy, at least if you do it well, takes your attention outside of any type of self-indulgent reflection/obsessive compulsive rumination.

Ryan Holiday 1:15 Sure.

Tim Ferriss 1:15 And as someone who has had a history of depression, which is being stuck in the past, and I think being highly self-referential, I mean, it, it, it... Depression is, I think, as someone who's experienced it a lot in life, uh, very self-obsessive, right?

Ryan Holiday 1:31 Yeah.

Tim Ferriss 1:31 So when you have something in front of you that requires and demands care, or it's gonna 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, uh, I think realized very quickly how absurd some of my reactions are to things, or have been historically, in the sense that if

Tim Ferriss 2:03 you have a problem at work, you have a problem with your partner, your spouse, your girlfriend, boyfriend, you can get upset and, uh, sort of, uh, create an imaginary agenda that they have where they deliberately did A, B or C to upset you.

Ryan Holiday 2:17 [laughs] Sure, sure.

Tim Ferriss 2:18 But with a dog, that's completely absurd. Like, at face value, it's completely absurd, right? So, so-

Ryan Holiday 2:23 'Cause all the problems are your fault with your dog.

Tim Ferriss 2:25 It's your fault, right. So if, if your dog chews on your shoes, that's your fault. It's a dog, and you-

Ryan Holiday 2:30 Yeah

Tim Ferriss 2:30 ... left your shoes out, right?

Ryan Holiday 2:32 Right.

Tim Ferriss 2:32 So a big part of, I think, raising a puppy well is making it extremely difficult to make mistakes that then become habits, right? That's, that's, that's, uh, 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.

Ryan Holiday 2:54 Right.

Tim Ferriss 2:54 Put them on something or in something that makes that impossible. And similarly, peeing in the house. To avoid that, use something like crate training. And so, so I think that when I became, particularly in the early periods of training Molly, upset because she wouldn't follow my instructions-

Ryan Holiday 3:16 Yeah

Tim Ferriss 3:17 ... uh, 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, um, emotion, which, you know, I think is, 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.

Ryan Holiday 3:35 Getting upset is fear shown in public?

Tim Ferriss 3:37 Getting angry.

Ryan Holiday 3:38 Yeah.

Tim Ferriss 3:38 Yep. And it's a coping mechanism. Some people shut down.

Ryan Holiday 3:41 Right.

Tim Ferriss 3:41 Some people learn to get angry. I learned to get angry, like, when I was, when I was little. So th- uh, doing that, though with this dog who, uh, does not speak English, uh, was so 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.

Ryan Holiday 4:03 Yeah.

Tim Ferriss 4:04 Right? I didn't, through sports and coaching and teaching or receiving teaching, had s- a little bit of positive reinforcement, but not, not, not a whole lot.

Ryan Holiday 4:13 Yeah.

Tim Ferriss 4:13 And so I've learned to go without it, even though that is unhealthy.

Ryan Holiday 4:17 Sure.

Tim Ferriss 4:18 And, uh, reading about animal training, if you really wanna 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.

Ryan Holiday 4:29 Yeah.

Tim Ferriss 4:29 Doesn't work underwater.

Ryan Holiday 4:31 Yeah.

Tim Ferriss 4:31 And they're faster than you are. So you have to figure out how to use, like, whistles and different clickers and means of marking the desired behavior and then rewarding.

Ryan Holiday 4:39 Sure.

Tim Ferriss 4:40 And getting into the habit of providing positive reinforcement, I think led to me doing that more. I sh- could, could still do it more with other people. And, like, how you treat other people, I think impacts how you treat yourself-

Ryan Holiday 4:54 Sure

Tim Ferriss 4:54 ... and relate to yourself. So I, I think that those are all pieces of the puzzle. And then last but not least, uh, feeling unconditional love, although, granted, giving your-

Ryan Holiday 5:07 It's very conditional [laughs]

Tim Ferriss 5:08 ... g- giving your dog food and treats helps a lot.

Ryan Holiday 5:10 Yeah.

Tim Ferriss 5:11 But feeling this love from an animal, uh, and experiencing that in the absence of language, I think is really powerful.

Ryan Holiday 5:23 Yeah.

Tim Ferriss 5:23 As someone, 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.

Ryan Holiday 5:40 Do you think it was, it was sort of giving you something to care about, like, to be responsible for that wasn't, there was, there's no, uh, there's no reason to have the dog. Like, you have the dog 'cause you love the dog.

Tim Ferriss 5:53 Right.

Ryan Holiday 5:53 Do you know what I mean?

Tim Ferriss 5:53 Yeah, yeah.

Ryan Holiday 5:53 Like, there's, 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, but-

Tim Ferriss 6:00 No

Ryan Holiday 6:00 ... y- you know what I mean?

Tim Ferriss 6:02 I, I think so. I mean, you w- you get a dog because you want a dog. It's, in a sense, a very selfish act.

Ryan Holiday 6:07 Yeah.

Tim Ferriss 6:07 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.

Ryan Holiday 6:14 Sure.

Tim Ferriss 6:14 But ultimately, you are choosing to have a dog.

Ryan Holiday 6:17 Right.

Tim Ferriss 6:17 Uh, similarly- I think having kids is, uh, and this isn't a bad thing, it's not a value judgment, but like it is a selfish decision. Like, you have kids because you want to have kids, right?

Ryan Holiday 6:30 Yeah.

Tim Ferriss 6:30 And, uh, I remember Mike Maples, who's this, um, very well-known investor and friend of mine said to me, he's like, "Rule number one with kids is, like, they owe you nothing. Like, their job is to receive love, not to give you love."

Ryan Holiday 6:41 Yeah.

Tim Ferriss 6:41 "Because you decided to have the kids."

Ryan Holiday 6:42 Right.

Tim Ferriss 6:43 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 sort of self-focused/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-

Ryan Holiday 7:12 Sure

Tim Ferriss 7:13 ... executed on everything else I wanted to execute on-

Ryan Holiday 7:16 Yeah

Tim Ferriss 7:16 ... 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 the dog.

Ryan Holiday 7:29 Right.

Tim Ferriss 7:29 And that's, those are two fundamentally different ways to look at it. And, uh, I think if you look at sort of the realm of behavior in humans and dogs, like, most animals, including humans, are poorly trained.

Ryan Holiday 7:45 Yeah.

Tim Ferriss 7:45 And to do it well takes a lot of effort and consistency. So i- if someone's ready for that, then I, I suggest, you know, adopting ideally. But otherwise, I've, I've seen people who, who get dogs and then just neglect them.

Ryan Holiday 8:01 Sure.

Tim Ferriss 8:02 Uh, and I'm conflicted as to how to feel about that, 'cause on one hand, if they're rescuing a dog from a kill shelter-

Ryan Holiday 8:09 Probably better, yes

Tim Ferriss 8:11 ... probably better. One could argue that's better. But I don't know. I'm not, um, yeah, I'm no professional ethicist, so.

Ryan Holiday 8:20 No, there's a, [clears throat] there's a thing David Brooks talks about when his son was born. Someone sent him an email and said, this was his first kid, they said, "You know, like welcome to unavoidable reality."

Tim Ferriss 8:30 [laughs]

Ryan Holiday 8:30 And the idea being that up until your, up until then, sure you have responsibilities with work and life, but like pretty much anything you don't wanna have to put up with, you don't have to put up with.

Tim Ferriss 8:40 Right, yeah.

Ryan Holiday 8:40 But as soon as you take on something like that, like with a kid it's like you think, "Okay, I'm gonna go to this thing at 1:00." But if your kid falls asleep at 12:59-

Tim Ferriss 8:51 Yep

Ryan Holiday 8:51 ... you're going to the thing when your kid wakes up.

Tim Ferriss 8:53 Yep.

Ryan Holiday 8:53 And I think dogs have an element of that too. Suddenly you're responsible for this thing that is totally dependent on you.

Tim Ferriss 8:59 Yeah.

Ryan Holiday 8:59 And the dog decides what the schedule is, not you, which if you're successful or self-absorbed, and they're kind of the same thing in different ways, it forces you to pivot your reality-

Tim Ferriss 9:10 Yeah

Ryan Holiday 9:11 ... in a way that makes you a better person, I think.

Tim Ferriss 9:13 I think so. And you develop, I don't wanna e- I, I s- I don't really wanna use the word patience. I think it's something else, maybe greater self-awareness and resilience in the face of the unpredictable.

Ryan Holiday 9:28 It's equanimity is what I think it is.

Tim Ferriss 9:30 Equanimity.

Ryan Holiday 9:30 Yeah.

Tim Ferriss 9:30 Yeah, equanimity we could use. Because it's like, all right, Molly gets sick. I'll give you an example. [laughs] Like I remember one morning I woke up to the, like, the most awful stench imaginable at like 4:00 in the morning.

Ryan Holiday 9:44 Right.

Tim Ferriss 9:45 And I'm very protective of my sleep. Historically, they're, like, one of the best ways to get me really spun up and upset is to like negatively affect my sleep.

Ryan Holiday 9:56 Okay.

Tim Ferriss 9:56 And it's like 4:00 in the morning, went to bed at 1:00.

Ryan Holiday 10:00 Yeah.

Tim Ferriss 10:00 And it's the most horrible stench you can imagine. I wake up, I turn on the light, and Molly has just shit everywhere in the bedroom.

Ryan Holiday 10:06 Right.

Tim Ferriss 10:06 Including on the wall, which I thought was very impressive. I'm like-

Ryan Holiday 10:08 Of course

Tim Ferriss 10:09 ... what possesses a dog to-

Ryan Holiday 10:10 Yeah

Tim Ferriss 10:10 ... shit against the wall? I don't know. Nonetheless, it's like, all right, this is, like this is what you're dealing with for the next-

Ryan Holiday 10:15 It's unavoidable reality

Tim Ferriss 10:16 ... hour, two hours-

Ryan Holiday 10:18 Right

Tim Ferriss 10:18 ... is putting on your hazmat gear and dealing with this. And, um, I think you develop, or I have developed, uh, to some extent, I don't think I'm the best at this, but the ability to put my- better put myself in other people's shoes.

Ryan Holiday 10:34 Sure.

Tim Ferriss 10:35 Because in a situation like that, it's clear to me Molly doesn't want to do what she's doing.

Ryan Holiday 10:42 Right. [laughs]

Tim Ferriss 10:43 There's something that's-

Ryan Holiday 10:44 She did not do this to ruin your sleep.

Tim Ferriss 10:45 She, she did not do it-

Ryan Holiday 10:46 Yeah

Tim Ferriss 10:46 ... to ruin my sleep. And, uh, it's, it's, it, it's not just unhelpful, but it's damaging to lose your, lose your, I was gonna say lose your shit-

Ryan Holiday 10:58 Sure

Tim Ferriss 10:58 ... but to get really upset in a situation like that. Uh, it-

Ryan Holiday 11:02 Sure

Tim Ferriss 11:02 ... it actually makes it harder to train your dog effectively. So the unavoidable reality piece, I think, is, is a, is a big part of it. And I think there's something to be said, uh, for, uh, 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, right?

Ryan Holiday 11:25 Yeah.

Tim Ferriss 11:26 He's a lot older-

Ryan Holiday 11:26 Yeah

Tim Ferriss 11:26 ... than I am, so like I'm, I'm like an 80-year-old when it comes to-

Ryan Holiday 11:30 Yeah

Tim Ferriss 11:30 ... possible procreation these days. But he said his brother, who ha- had a few kids at that time, said, "Oh, welcome to the human race."

Ryan Holiday 11:37 Yeah.

Tim Ferriss 11:37 Like when his first kid was born.

Ryan Holiday 11:38 Sure.

Tim Ferriss 11:39 And I do think that, this doesn't need to apply to everybody, but there, there is a certain, um, self-absorption that is encouraged and fostered in modern life that I think is relatively new.

Ryan Holiday 11:59 Yeah.

Tim Ferriss 11:59 Does that make sense?

Ryan Holiday 11:59 Mm-hmm.

Tim Ferriss 11:59 I mean, because we're, even in a densely populated city, you can be very physically isolated. Uh, and you don't have responsibilities or things to care for that w- that for the vast majority or, of our evolution would have been commonplace, right? You don't have to-

Ryan Holiday 12:19 Totally

Tim Ferriss 12:19 ... you, like you're not having kids-

Ryan Holiday 12:21 Yeah

Tim Ferriss 12:21 ... at like 19 or 18.

Ryan Holiday 12:22 You don't live with your, your grandparents.

Tim Ferriss 12:24 Right. You don't live with your grandparents. You're not-

Ryan Holiday 12:27 Not hunting together

Tim Ferriss 12:28 ... hunting and gathering-

Ryan Holiday 12:29 Yeah

Tim Ferriss 12:30 ... uh, where dogs would certainly have played a role-

Ryan Holiday 12:33 Mm-hmm

Tim Ferriss 12:33 ... and did play a role. So I, I think that in some way, having a dog or having a garden or having kids, these are all things we've evolved, sort of co-evolved with.

Ryan Holiday 12:47 Totally.

Tim Ferriss 12:48 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.

Ryan Holiday 12:57 No, I, I think that's really interesting, the idea of, like, sort of consciously developing empathy-

Tim Ferriss 13:01 Yeah

Ryan Holiday 13:01 ... is, a- and, and how almost you could argue that the way society is set up now consciously stunts the development of empathy. Like, like, the, the famous one, you're like, "Oh." You hear someone who's like, "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." Like, it literally never occurred to you-

Tim Ferriss 13:27 Yeah

Ryan Holiday 13:27 ... that the baby was crying because there's something wrong with the baby, and that this isn't fun for the baby, right? Or, and it's definitely not fun for the parent. Like, they don't want it. So it's like I think with dogs too, you, like, you hear a dog barking. You, you, like you hear about those, you're like, "Oh, I've been through that," or, "Oh, that's not fun for you."

Tim Ferriss 13:44 Yeah.

Ryan Holiday 13:45 It sort of forces you, I think that's what they mean by that idea of welcome to the human race, not welcome to the human race, you now have c- like, ma- you, you know you're reproducing. It's welcome to the human race, you're no longer, like, a lone wolf.

Tim Ferriss 13:58 Yeah.

Ryan Holiday 13:58 You, like, understand, like, how... You understand what everyone else has been dealing with while you've been self-absorbed this entire time.

Tim Ferriss 14:06 Yeah. It's sort of als- like welcome to the human/hominid condition.

Ryan Holiday 14:11 Yeah.

Tim Ferriss 14:11 That was the norm for-

Ryan Holiday 14:14 Right

Tim Ferriss 14:14 ... like, millennia.

Ryan Holiday 14:16 Yes.

Tim Ferriss 14:16 Has been the norm, and, like, thank God you've snapped out of your aberrant, strange behavior that is-

Ryan Holiday 14:23 Totally

Tim Ferriss 14:23 ... really kind of a new luxury.

Ryan Holiday 14:25 Yeah, that's right.

Tim Ferriss 14:26 Uh.

Ryan Holiday 14:27 Did you, have you felt like moving to Austin has, has had an impact on you in a, in a similar way? Like, I, I feel like that there is also something selfish and strange about the New York life or the San Francisco life or the LA life-

Tim Ferriss 14:40 Yeah

Ryan Holiday 14:40 ... that I've just experienced the South and, and Texas and it being a little bit different.

Tim Ferriss 14:47 Yeah. Well, Texas, the South, and Austin are all-

Ryan Holiday 14:50 A little different, but-

Tim Ferriss 14:51 A little different.

Ryan Holiday 14:51 Yeah.

Tim Ferriss 14:51 But I, I understand what you mean. I, I think that, um, Austin has been so far, let's call it three years in, three, four years in, however long it is, has been, uh, very refreshing and rejuvenating in part, and this is coming back to your point about, or observation about New York and LA and so on, in part because there is no one mono conversation.

Ryan Holiday 15:18 Yeah.

Tim Ferriss 15:19 And that could be seen as symptomatic of a huge benefit of living here or a huge drawback.

Ryan Holiday 15:26 Right.

Tim Ferriss 15:26 Meaning there are certain, there are certain locations in the world like New York for finance. In New York, you have finance.

Ryan Holiday 15:34 Yeah.

Tim Ferriss 15:35 True in other places too, say London. If you want to be in the NBA All-Star game of finance-

Ryan Holiday 15:43 Yeah, well

Tim Ferriss 15:43 ... it behooves you to go to one of those places.

Ryan Holiday 15:46 Sure.

Tim Ferriss 15:46 And as a result, it attracts people who are highly driven in certain fields, whether that's fashion, finance, and so on. And, uh, as you've mentioned to me before, I think it's, th- there's a high correlation between self-absorption and professional success-

Ryan Holiday 16:05 Yeah

Tim Ferriss 16:05 ... on some level.

Ryan Holiday 16:06 There has to be.

Tim Ferriss 16:07 And if you look at Los Angeles, even though Los Angeles is a huge, in reality, combination of different cities, entertainment is the, the predominant mono conversation, whereas here in Austin, you have, um, more of a medley.

Ryan Holiday 16:28 Yeah.

Tim Ferriss 16:28 And for that reason, I find it, I find that I don't overtax a single sort of conversational track or part of my brain. Like, you can quite easily hop from lily pad to lily pad and maintain some degree of, um, mental dexterity, emotional dexterity. There's just, there's just more to easily dip your toe into here.

Ryan Holiday 16:56 Yeah.

Tim Ferriss 16:56 And it does exist in a place like San Francisco.

Ryan Holiday 16:59 Sure.

Tim Ferriss 17:00 Uh, but it takes more effort to avoid the mono conversations.

Ryan Holiday 17:05 And don't you think one of the downsides of the mono conversation is also, m- let's call it mono thinking, right? So I think, I think w- w- we have tended these days to define diversity as merely a function of race-

Tim Ferriss 17:18 Yeah

Ryan Holiday 17:18 ... or, or gender, but I think diversity as far as lifestyles, thinking, careers, interests, you know, i- is, is also super important.

Tim Ferriss 17:31 The main downside of the mono conversation is mono thinking, and, uh, 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.

Ryan Holiday 17:55 Yeah.

Tim Ferriss 17:56 And that I think is, um, I think is very dangerous.

Ryan Holiday 18:03 Yeah.

Tim Ferriss 18:04 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-

Ryan Holiday 18:23 Yeah

Tim Ferriss 18:23 ... and challenge deeply held beliefs, or I should say better yet, deeply assumed beliefs.

Ryan Holiday 18:31 Yeah.

Tim Ferriss 18:32 And that is very increasingly difficult to do in the Bay Area.

Ryan Holiday 18:37 Yeah.

Tim Ferriss 18:37 And in much of, uh, c- ... certainly culture in the United States. Uh, and we're in Austin-

Ryan Holiday 18:47 Yeah

Tim Ferriss 18:47 ... which is jokingly referred to as the Blueberry in the Tomato Soup.

Ryan Holiday 18:50 Yeah.

Tim Ferriss 18:50 Uh, right?

Ryan Holiday 18:51 Yeah, the s- the, the Blue Dot in the Red Ocean.

Tim Ferriss 18:53 Yeah.

Ryan Holiday 18:53 Yeah.

Tim Ferriss 18:53 And, uh, so, so it, it, it is a... One might think that Austin is just a smaller version of San Francisco, but it's not.

Ryan Holiday 19:02 Yeah, yeah.

Tim Ferriss 19:02 It's, it's, uh, you do have a commingling of sort of political, artistic, and financial interests-

Ryan Holiday 19:13 Yes

Tim Ferriss 19:14 ... that I deeply enjoy. And the, the ability to easily, for instance, I mean, we, we're, we're sitting here right above a restaurant called Jeffrey's and next door is Josephine House. And I had dinner at Josephine House with someone, I won't mention by name, um, most people wouldn't recognize him, but an extremely successful, uh, investor, financier, who, uh, came in from out of town, came in from elsewhere in Texas. Very well-educated, extremely smart, and also a sort of staunch Republican-

Ryan Holiday 19:55 Yeah

Tim Ferriss 19:55 ... on many levels. Not all levels, right? It's easy to paint with that broad brush.

Ryan Holiday 19:59 Yeah.

Tim Ferriss 19:59 And when you have the ability to sit down with someone like that easily here, it becomes harder to do what is so frequently done in San Francisco as a place where I-

Ryan Holiday 20:12 Yeah

Tim Ferriss 20:12 ... spent a lot of time, you know, almost two decades in the Bay Area, to say, "Oh, right-wingers are all knuckle-dragging idiots."

Ryan Holiday 20:19 Yeah.

Tim Ferriss 20:19 It becomes much more difficult to paint-

Ryan Holiday 20:23 'Cause you know by direct firsthand experience that that's not true.

Tim Ferriss 20:26 It's not that. It's not true in many cases, and it's just not that simple.

Ryan Holiday 20:31 Right.

Tim Ferriss 20:31 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.

Ryan Holiday 20:43 Yeah.

Tim Ferriss 20:44 It just requires more thought. Uh, but I, I like the fact that it's, it's not as easy to kinda divide this country into like a left-right civil war-

Ryan Holiday 20:54 Yeah

Tim Ferriss 20:56 ... of smart versus dumb, rich versus poor, this versus that. It's not that, it's not as easy to do here, and I, and I like that.

Ryan Holiday 21:04 Yeah.

Tim Ferriss 21:05 Uh, I s- I, I s- also think that it would be difficult for me to live in many places outside of Austin in Texas.

Ryan Holiday 21:11 Sure.

Tim Ferriss 21:12 Right? Which is not a slight against, uh, 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 fact that it has some of the ingredients, and we'll see if this backfires over time, it might, but, uh, that made Silicon Valley, Silicon Valley.

Ryan Holiday 21:34 Yeah.

Tim Ferriss 21:34 You have uni- 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.

Ryan Holiday 21:51 Yeah.

Tim Ferriss 21:51 And as you and I know, I mean, there is an incredible writing scene here.

Ryan Holiday 21:54 Yeah.

Tim Ferriss 21:54 There's some fantastic writers.

Ryan Holiday 21:56 Mm-hmm.

Tim Ferriss 21:56 And, uh, it, it, it has a lot of the ingredients I like about Silicon Valley without the sort of smug-

Ryan Holiday 22:05 Yeah

Tim Ferriss 22:05 ... self-satisfaction that I find so unappetizing.

Ryan Holiday 22:10 Do you know what I think is important of when I was sort of like thinking about places to live? Is like you're naturally a competitive person and sort of keeping up with the Joneses part of it. Like, like it's very easy for life to become an arms race, right? 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-

Tim Ferriss 22:32 Yeah

Ryan Holiday 22:33 ... you become more inwardly focused on what you wanna do and what's important to you, rather than going, "Oh, did you hear what so-and-so just got?"

Tim Ferriss 22:41 Yeah.

Ryan Holiday 22:41 Or, you know, like y- and I think that's a healthier way to live also.

Tim Ferriss 22:44 Yeah. That's, I, I think that's a very good observation. There's no one lead dog to follow.

Ryan Holiday 22:51 Yes.

Tim Ferriss 22:51 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.

Ryan Holiday 23:02 Yeah.

Tim Ferriss 23:03 Uh, and I like that. 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-

Ryan Holiday 23:15 Yeah

Tim Ferriss 23:15 ... and make your mark and kinda summit the mountain.

Ryan Holiday 23:18 Sometimes you need that to drive you forward, but that maybe isn't how you wanna spend your whole life.

Tim Ferriss 23:25 Yeah, I think that there's a point, at least there was for me, where you've, you've basically alternated between park and sixth gear-

Ryan Holiday 23:36 Yeah

Tim Ferriss 23:36 ... and you're like, "Oh, wait. There are five other gears."

Ryan Holiday 23:38 Yeah.

Tim Ferriss 23:39 "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." There are actually all of these gears in between that allow you to experience and enrich life in myriad 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.

Ryan Holiday 24:17 Yeah.

Tim Ferriss 24:17 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.

Ryan Holiday 24:39 Yeah.

Tim Ferriss 24:40 So if I'm, if I'm thrown into any game, even if it's a stupid game that I shouldn't participate in-

Ryan Holiday 24:44 You wanna win

Tim Ferriss 24:45 ... I'm gonna win. I'm gonna wanna win. And recognizing that- Uh, is important. I, I, I remember having, um, Peter Thiel on the podcast long ago.

Ryan Holiday 24:56 I've listened, yeah.

Tim Ferriss 24:56 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-

Ryan Holiday 25:09 Yeah

Tim Ferriss 25:09 ... to be more satisfied or more content?"

Ryan Holiday 25:11 Yeah.

Tim Ferriss 25:12 And if your default is competition, uh, I think it pays huge dividends to be aware of that and to ask those types of questions.

Ryan Holiday 25:24 My favorite line from him is that, "Competition is for losers."

Tim Ferriss 25:27 Competition is for losers.

Ryan Holiday 25:28 No, but I, 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 like I, I, correct me if I'm wrong, but I think your decision to sort of stop angel investing or stop actively angel invest coincides with your decision to move to Austin or that overlaps.

Tim Ferriss 25:51 Yeah. Yeah, very, very much an overlap. Yeah, 2015 and then shortly thereafter.

Ryan Holiday 25:57 S- so how, how much... W- one, I'm, I'm curious about your decision to sort of, you know, you're, 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, 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, a day-to-day reality? You know, uh, how much are, how much are they connected?

Tim Ferriss 26:21 I, I think they are all really interrelated, and I'm not gonna try to fabricate some grand master plan because-

Ryan Holiday 26:28 Yeah

Tim Ferriss 26:29 ... 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-

Ryan Holiday 26:52 Right

Tim Ferriss 26:52 ... or fear-based decision-making. Not perfect, but in the case 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-

Ryan Holiday 27:18 Sure

Tim Ferriss 27:18 ... with a, with a nice like 2% management fee and 20% carry when you're using other, uh, limited partner money, which is a fine model.

Ryan Holiday 27:27 Sure.

Tim Ferriss 27:27 It's, it's, I don't have an ethical issue with it, but I, I realized that to do a good job with an increasingly, um, increasingly high number of decks in the blackjack-

Ryan Holiday 27:41 Yeah

Tim Ferriss 27:41 ... game-

Ryan Holiday 27:41 Yeah

Tim Ferriss 27:42 ... in the form of bloated terms, higher prices, uh, f- foreign capital flight from places like China coming into the US and affecting terms, I would either, I could no longer do an effective job part-time.

Ryan Holiday 27:55 Yeah.

Tim Ferriss 27:56 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 in that world, I would be effectively replaceable.

Ryan Holiday 28:07 Yeah.

Tim Ferriss 28:07 I would be in a long line of people trying to do the same thing. And that my drive to do that would be predominantly driven by fear of missing out and a, I think a s- a sort of cortisol-driven scarcity mentality that is really fostered in the world of startups.

Ryan Holiday 28:30 Sure.

Tim Ferriss 28:31 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.

Ryan Holiday 28:41 Yeah.

Tim Ferriss 28:41 And in other words, from a mental health perspective, from a physical health perspective, from an emotional health perspective that, that it would, uh, it, it would end poorly. And I tried to do, uh, to make a, 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.

Ryan Holiday 29:02 Yeah.

Tim Ferriss 29:03 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, uh, the, the jury's not out until the final-

Ryan Holiday 29:16 Till the wire transfer comes in

Tim Ferriss 29:17 ... outcome.

Ryan Holiday 29:17 Yeah.

Tim Ferriss 29:17 Until the wire transfer comes in. And that final outcome for many of the startups that you bet on will take 7 to 12 years.

Ryan Holiday 29:25 Yeah.

Tim Ferriss 29:26 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?"

Ryan Holiday 29:42 Right.

Tim Ferriss 29:42 Or that things are sufficiently influenced by elements under my control that I can help steer outcomes.

Ryan Holiday 29:51 Yeah.

Tim Ferriss 29:51 Right? You could 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, uh, that in addition to many other things, a very close friend of mine asking me to please not stop writing.

Ryan Holiday 30:09 Yeah. This is Kamal.

Tim Ferriss 30:11 Kamal Ravikant, great guy. Given the feedback that he'd seen at events with, uh, readers of mine, he said, "You'll never have that impact investing."

Ryan Holiday 30:21 Right.

Tim Ferriss 30:21 "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.

Ryan Holiday 30:31 Yeah.

Tim Ferriss 30:31 I've done better in investing by far than I have in writing. And I've been very-

Ryan Holiday 30:35 Well, certain fields are more lucrative than other fields, right?

Tim Ferriss 30:37 Yeah, certain fields-

Ryan Holiday 30:38 So not all success-

Tim Ferriss 30:39 Yeah, yeah

Ryan Holiday 30:39 ... is created equal.

Tim Ferriss 30:40 Yeah, for sure. And if you're, if you're trying to get rich, when people are like, "I'm just gonna sell a few million copies of books," I'm like, "God bless you. Good luck." Because that is a really-

Ryan Holiday 30:49 Yes

Tim Ferriss 30:49 ... it's difficult to make that math work.

Ryan Holiday 30:51 Yeah.

Tim Ferriss 30:52 There are far easier ways to make money. 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.

Ryan Holiday 31:05 Right.

Tim Ferriss 31:05 So if you remove the investing-

Ryan Holiday 31:07 Why am I here?

Tim Ferriss 31:07 ... 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."

Ryan Holiday 31:18 Yeah.

Tim Ferriss 31:19 Not none, but few. If I remove the investing, my professional need to be here is nonexistent.

Ryan Holiday 31:27 Sure.

Tim Ferriss 31:28 So why am I here?

Ryan Holiday 31:29 Yeah.

Tim Ferriss 31:30 What do I like? What do I dislike? And a lot went into the decision, but, uh, led me to consider a, a number of different places, but predominantly Austin, which I'd wanted to move to right after college, just didn't get the job-

Ryan Holiday 31:43 Yeah

Tim Ferriss 31:43 ... at Trilogy Software. Uh, and if you look at some of these decisions, they're almost all catalyzed by a breakdown of some type.

Ryan Holiday 31:55 Yeah.

Tim Ferriss 31:55 Wearing out. Some type of burnout.

Ryan Holiday 31:57 Yeah.

Tim Ferriss 31:57 That happened with the, uh, 4-Hour Chef leading to podcasting.

Ryan Holiday 32:02 Yeah.

Tim Ferriss 32:02 I just flamed out 'cause I tried to do a, what should've been a three or four-year project in a year or a year and a half, which was a suicide mission. And that, that extreme pain and burnout then led to test driving the podcast.

Ryan Holiday 32:17 Right.

Tim Ferriss 32:18 Right? So a lot of my walking away at the top, so to speak, I would like to say is this sort of grand philosophical insight and, like, balls of steel and-

Ryan Holiday 32:29 Yeah, 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. I'm miserable."

Tim Ferriss 32:35 It's often both.

Ryan Holiday 32:36 Yes, right.

Tim Ferriss 32:37 But it starts with this is awful and miserable.

Ryan Holiday 32:39 Right.

Tim Ferriss 32:40 So it's sort of the breakdown equals breakthrough, I'm, I'm borrowing that from someone, that is catalyzed by wearing out.

Ryan Holiday 32:48 Yeah.

Tim Ferriss 32:49 An- and I suppose where I've been, uh, fortunate or made some good decisions is instead of just plowing through that, sometimes it's physically impossible.

Ryan Holiday 33:00 Yeah.

Tim Ferriss 33:00 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.

Ryan Holiday 33:06 Yeah.

Tim Ferriss 33:06 Journal, journal, journal.

Ryan Holiday 33:07 Mm-hmm.

Tim Ferriss 33:07 And I do a lot of journal- journaling, asking questions. I don't find my thinking to be clear at all unless I'm writing.

Ryan Holiday 33:13 Yeah.

Tim Ferriss 33:14 Uh, and I think Kevin Kelly was the one who said this to me, amazing guy, uh, that he doesn't write to put his ideas down, he writes to think.

Ryan Holiday 33:23 Yeah, sure.

Tim Ferriss 33:23 He writes as a means of thinking. And in doing that, I then have looked at options like stopping all angel investing.

Ryan Holiday 33:32 Yeah.

Tim Ferriss 33:33 Right? I like to ask these, 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 s- I don't know why I find this so easy, but a lot of people find it hard. I, I'm not sure why that is. I think it's practice predominantly.

Ryan Holiday 34:00 Yeah.

Tim Ferriss 34:00 Like, what would a, what would a meaningful but reversible experiment look like? That's it.

Ryan Holiday 34:07 Yeah.

Tim Ferriss 34:07 Right? Okay. With the podcast, I committed to, I think it was six episodes.

Ryan Holiday 34:10 Yeah.

Tim Ferriss 34:10 Then if I don't like it, I can walk. That's, that's it. And with Austin, it's like you can always, I can always move back to the Bay Area-

Ryan Holiday 34:17 Yeah

Tim Ferriss 34:17 ... if my realization is, "Oh my God, I didn't realize how much I loved-"

Ryan Holiday 34:22 Sure

Tim Ferriss 34:22 ... "these things I now miss," I can always move back. It's, it's completely reversible.

Ryan Holiday 34:26 I think that's a great... 'Cause I remember I was asking re- you recently for some advice on something that was like sort of a big purchase. It would be a big lifestyle transition. And you were like, "Well, how else are you gonna find out if you wanna do it or not?" And you said, like, "Why don't you just commit to doing it for two years?" And, and that's totally right, 'cause I remember when I dropped out of college, I was, it's like, "I'm dropping out of college. This is the biggest decision I've ever made in my life."

Tim Ferriss 34:48 Yeah.

Ryan Holiday 34:48 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 were like, "You li- there, there's not a form for that. There's a take a semester off form." You know?

Tim Ferriss 35:00 Yeah, yeah.

Ryan Holiday 35:00 But we think these lifestyle decisions are irrevocable-

Tim Ferriss 35:04 Mm-hmm

Ryan Holiday 35:05 ... and life altering.

Tim Ferriss 35:07 Yeah.

Ryan Holiday 35:07 And really, they can start very small.

Tim Ferriss 35:10 They can start really small, and I want to just highlight something you just said which i- which I think gets missed oftentimes in the romanticizing about dropping out-

Ryan Holiday 35:21 Yeah

Tim Ferriss 35:21 ... of college, that for many of the folks who are, like, the name brand titans who have a-

Ryan Holiday 35:29 Yeah

Tim Ferriss 35:29 ... who have adopted dropping out of college as, uh, one of their favorite stories and, uh, drums to beat, if you have the, the Zuckerbergs, the Teals, or whoever it might be, although Teal's not a great example of dropping out himself, but-

Ryan Holiday 35:44 Yeah

Tim Ferriss 35:44 ... you talk about these incredible icons of entrepreneurship who dropped out of school, it's really important to realize that when you drop out of Harvard or Stanford-

Ryan Holiday 35:55 Different

Tim Ferriss 35:55 ... those administrations effectively say, "Come back anytime you want."

Ryan Holiday 36:00 Yeah.

Tim Ferriss 36:01 And that is a, a really important sort of footnote that people need to be-

Ryan Holiday 36:09 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 wanna drop out of college all the time. They're like, "I'd like to be an entrepreneur. I wanna drop out of college." Mark Zuckerberg left college because Facebook was successful.

Tim Ferriss 36:23 Right.

Ryan Holiday 36:23 Right? Um, he wasn't dropping out of college to then go start the Facebook.

Tim Ferriss 36:27 Yeah.

Ryan Holiday 36:28 And so it, you can do the thing now, and then if it's working, you can transition away.

Tim Ferriss 36:33 Right.

Ryan Holiday 36:33 You can decide to go, "Hey, what would it look like if I in, if I committed full time to this for six months? What would come of that?" And I think it's not like you've never been to Austin before and you sold everything you, you own.

Tim Ferriss 36:45 Yeah, no.

Ryan Holiday 36:45 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.

Tim Ferriss 36:56 Yeah. I've, I almost never burn the ships.

Ryan Holiday 37:00 Yeah.

Tim Ferriss 37:00 Yeah. I, I can't think of offhand a single example of me burning the ships and throwing caution to the wind and just-

Ryan Holiday 37:06 Yeah

Tim Ferriss 37:07 ... leaping into the unknown. That's just not how I do things. And-

Ryan Holiday 37:10 It's also 'cause you don't need to do them. That, like, pe-

Tim Ferriss 37:12 Yeah

Ryan Holiday 37:12 ... I think you don't need to do that. It's, and that's sort of the-

Tim Ferriss 37:14 And by you, I think mo- that means most people.

Ryan Holiday 37:18 Yeah.

Tim Ferriss 37:18 Like, most people should not ... sort of jump headfirst into the shallow end and hope that they figure it out.

Ryan Holiday 37:23 Yeah.

Tim Ferriss 37:23 I think it's a terrible idea. And if you look at some of the, 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, they are better called experts in risk mitigation and capping the downside.

Ryan Holiday 37:48 Sure. Yeah.

Tim Ferriss 37:48 Right? Like he figured out how to lease planes, I think from Boeing, might have been Airbus, for Virgin Atlantic-

Ryan Holiday 37:54 Yeah

Tim Ferriss 37:54 ... and set up a structure such that the financial risks usually associated with airlines were dramatically mitigated.

Ryan Holiday 38:02 Yes.

Tim Ferriss 38:03 And, uh, he made a lot of exciting unusual bets, most of which were survivable bets.

Ryan Holiday 38:11 Yeah.

Tim Ferriss 38:12 Right?

Ryan Holiday 38:12 Yeah, Jeff Bezos says, "I don't believe in bet the company bets."

Tim Ferriss 38:16 Yeah.

Ryan Holiday 38:16 He's like, "I wanna be constantly taking risks, small risks-

Tim Ferriss 38:20 Yeah

Ryan Holiday 38:20 ... that are survivable. I don't want the 'if this doesn't work, we go out of business' risk." He's like, "You've waited too long if you have to take those risks."

Tim Ferriss 38:28 Yeah. Yeah, and a- as you mentioned with Austin, I mean, I had been to Austin 15 times.

Ryan Holiday 38:34 Yeah.

Tim Ferriss 38:34 I had spent increasingly long periods of time here each trip to South by Southwest. So I, I had already done more than dip my toe in the water.

Ryan Holiday 38:43 Yeah.

Tim Ferriss 38:44 And it was really a question of whether I would enjoy living here. I knew I enjoyed being here-

Ryan Holiday 38:47 Yeah, right

Tim Ferriss 38:48 ... for short periods of time. Would I enjoy living here, which is a whole separate question. And there are ways to test.

Ryan Holiday 38:54 Yes.

Tim Ferriss 38:54 So I, I think my comfort with walking away at the top is a result of a high degree of comfort with, and a, a large amount of practice in thinking about my life as a series of experiments.

Ryan Holiday 39:14 Yeah.

Tim Ferriss 39:14 And it's, it's also just being a student of recent history, right? Look at Dave Chappelle. He's like, he's crazy.

Ryan Holiday 39:25 Yeah.

Tim Ferriss 39:26 He walked away from $50 million or whatever.

Ryan Holiday 39:27 Right.

Tim Ferriss 39:27 And then he comes back and he does, I don't know what the numbers are exactly, what, 100-

Ryan Holiday 39:30 Yeah

Tim Ferriss 39:30 ... $100 million with Netflix?

Ryan Holiday 39:31 Yeah.

Tim Ferriss 39:31 Dave Chappelle's fine.

Ryan Holiday 39:32 Yeah. Sure.

Tim Ferriss 39:33 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 of 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?'"

Ryan Holiday 39:50 Right. Sure.

Tim Ferriss 39:50 Like, Will Smith can take all the time he wants.

Ryan Holiday 39:52 Yeah.

Tim Ferriss 39:53 Uh, and I, I think that underscores the importance of just focusing on being as good as possible at your craft. That's-

Ryan Holiday 40:06 Yeah, that's a Cal Newport thing. Like, if you're so good they can't ignore you, you get to dictate your terms.

Tim Ferriss 40:11 Yeah. Yeah. And, uh, I am extremely risk-averse. Um, risk defined as something with a h- with a high likelihood of an irreversible outcome.

Ryan Holiday 40:24 Yeah.

Tim Ferriss 40:26 The, the, the bet the farm.

Ryan Holiday 40:28 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?

Tim Ferriss 40:37 Good risk, for me, ha- has a few characteristics. Uh, two of the key characteristics would be high, high 90-plus percent likelihood of developing, developing or deepening skills that will transfer to other things.

Ryan Holiday 40:55 Okay.

Tim Ferriss 40:56 Whether now or in the future, even if this project fails. Uh, another characteristic of good risk would be developing relationships that can transcend this project-

Ryan Holiday 41:11 Yeah

Tim Ferriss 41:12 ... 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, uh, or to take things less seriously, which I think often go together.

Ryan Holiday 41:35 Yeah.

Tim Ferriss 41:35 Right? 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.

Ryan Holiday 41:44 Yeah.

Tim Ferriss 41:44 Right? The podcasting and doing six episodes is a great example.

Ryan Holiday 41:46 Yeah.

Tim Ferriss 41:47 'Cause 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.

Ryan Holiday 41:56 Yeah.

Tim Ferriss 41:56 And no, it's not.

Ryan Holiday 41:56 Right.

Tim Ferriss 41:56 After doing six episodes, it's like, "Oh, all right. Actually, I'm not scared-

Ryan Holiday 41:59 Sure

Tim Ferriss 41:59 ... by audio at all."

Ryan Holiday 42:00 Yeah.

Tim Ferriss 42:00 Because these mics, these cables, and the recorder that's on this chair-

Ryan Holiday 42:05 Yeah

Tim Ferriss 42:05 ... are like 500 bucks and you're-

Ryan Holiday 42:07 Right

Tim Ferriss 42:07 ... locked and loaded. And the editing's actually, uh, pretty straightforward. Uh, so those are three characteristics of, of good risk. And then, uh, 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, right? I want to understand what the landscape, political, legal, and so on looks like in Austin. Uh, I wanna look at population growth, I wanna look at employment growth.

Ryan Holiday 42:43 Yeah.

Tim Ferriss 42:43 I wanna look at median home costs-

Ryan Holiday 42:46 Yeah

Tim Ferriss 42:47 ... and how prices are moving, not just in Austin, but compared to my other options on the table.

Ryan Holiday 42:54 So the opportunity cost of the decision.

Tim Ferriss 42:55 It's a relative decision. It's not an absolute decision.

Ryan Holiday 42:58 Yeah.

Tim Ferriss 42:59 Uh, because, uh, uh, and I'm also gonna look at, let's say if I stay in San Francisco, what are, what are the risks of the status quo?

Ryan Holiday 43:11 Yeah.

Tim Ferriss 43:11 Like, what are the knowns that I dislike, and then what are the possible changes that I might dislike? So not just looking at the, the potential upside and downside and pros and cons of the new option- But comparing it to the current option.

Ryan Holiday 43:26 Sure.

Tim Ferriss 43:26 That sounds so self-evident, but it is not common practice, right?

Ryan Holiday 43:31 Right.

Tim Ferriss 43:31 Most people just assume, "All right, this is my known, and I'm gonna look at the risks and pros and cons of this new option." I'm always looking at relative.

Ryan Holiday 43:41 Yeah.

Tim Ferriss 43:41 I'm looking at not just opportunity cost, uh, but the sort of relative attractiveness, right? And that can apply to just about anything. I mean, it can, it can apply to startups certainly. Uh, and the... In terms of bad risk, I, I, I do look at financial risk. I look at reputational risk. I look at legal liability risk. And, uh, I do, I do, I do more comprehensive risk assessment than I do opportunity assessment, in part because I want to look for asymmetric-

Ryan Holiday 44:26 Sure

Tim Ferriss 44:26 ... bets.

Ryan Holiday 44:27 Yeah.

Tim Ferriss 44:27 In the sense that if I know I can cap my downside, that there is little or n- I can manage or completely eliminate reputational and legal risk by asking for, let's say, an indemnity clause-

Ryan Holiday 44:41 Yeah

Tim Ferriss 44:41 ... and having a written record of what we agree my responsibilities will or will not be, and I'm putting in $50,000.

Ryan Holiday 44:49 Yeah.

Tim Ferriss 44:50 In a sense, if I can control my time that is allocated to this, my max downside risk is 50%.

Ryan Holiday 44:56 Right.

Tim Ferriss 44:56 But if I'm investing in software as a service company-

Ryan Holiday 44:59 It's $50,000 you mean.

Tim Ferriss 45:00 Sorry.

Ryan Holiday 45:00 Yeah.

Tim Ferriss 45:00 $50,000. If, though, I'm investing in a sector, in a vertical, in a type of company, like software as a service or whatever, that has comparables which show 100x returns, 1000x returns, I'll take that bet all day long.

Ryan Holiday 45:17 Yeah.

Tim Ferriss 45:18 Right? If the team and so on-

Ryan Holiday 45:20 Sure, sure

Tim Ferriss 45:20 ... give it a reasonable likelihood of success, that is a great asymmetric bet. And 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, uh, and how you might consider arbitrage and so on. But, like, uh, Austin for me is a very, um, it's a very simple bet where it's easy to cap the downside.

Ryan Holiday 45:51 It seems to me that's the main strategy in your life is, is capping downside. So it's like, okay, you put $50,000 in a startup, the most you can lose is 50,000. You spend $500,000 on a real estate investment-

Tim Ferriss 46:06 Mm-hmm

Ryan Holiday 46:06 ... uh, you're responsible for the cost of maintaining the property. You know, like, it, it's a, it's a totally different... And so, and I think that, that explains your experiment thing. So it's not I'm starting a podcast, now I have to have a podcast forever. You're thinking, "I'm committing to six, so the most... If the, if I don't like it, the most I have to do is six episodes of something I don't like."

Tim Ferriss 46:29 Yeah.

Ryan Holiday 46:29 Do you know what I mean?

Tim Ferriss 46:30 Yeah.

Ryan Holiday 46:30 You're, you're, you're capping, you're capping so it's not endless amounts of losses, whether that's time, resources, happiness, money.

Tim Ferriss 46:38 Yeah. And, uh, I always try to cultivate walkaway power with my own projects.

Ryan Holiday 46:50 How do you do that?

Tim Ferriss 46:51 Uh, w- I'll explain or try to explain why I think it's important first. If, if I feel like I have to do something, you lose your optionality.

Ryan Holiday 47:02 Yeah.

Tim Ferriss 47:02 Right? Uh, and n- furthermore, you begin to make decisions out of fear or guilt, which in my experience turn out, almost always turn out poorly.

Ryan Holiday 47:12 Yeah.

Tim Ferriss 47:14 Similar if you're making decisions out of prestige.

Ryan Holiday 47:16 Yeah.

Tim Ferriss 47:16 Can turn out very poorly. I think I borrowed that from Maria Popova, uh, and what she said once on the po- on the podcast. But cultivating walkaway power is a function for me of, A, revisiting how little you actually need-

Ryan Holiday 47:36 Yeah

Tim Ferriss 47:36 ... frequently.

Ryan Holiday 47:37 Yep. This is Seneca.

Tim Ferriss 47:40 Yeah, Seneca. Not Timur's Pauper's Huts-

Ryan Holiday 47:43 Yeah

Tim Ferriss 47:43 ... but, you know, I will set aside a certain number of days each month, or whatever it is, to get by with the scantest, scantest or scantiest, I always mess that up, affair. But practicing periods of poverty or, uh, making-

Ryan Holiday 48:00 It's like knowing, being okay with a rock bottom, so you're not-

Tim Ferriss 48:02 Yeah, making do.

Ryan Holiday 48:03 Yeah.

Tim Ferriss 48:03 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-

Ryan Holiday 48:12 Yeah

Tim Ferriss 48:12 ... with boiling water.

Ryan Holiday 48:13 Yeah.

Tim Ferriss 48:14 And everything was great. And granted, it's, it's different when you do it for an extended period of time. It's different if that's your only option.

Ryan Holiday 48:20 Sure, yeah.

Tim Ferriss 48:21 But nonetheless, constantly revisiting and confirming how little is actually needed is number one. Uh, number two is doing, uh, fear-setting, this exercise that I talk quite a lot about, which is, of, of course, borrowed-

Ryan Holiday 48:37 Yeah

Tim Ferriss 48:37 ... directly from stoicism and cognitive behavioral therapy, which is also largely based on-

Ryan Holiday 48:43 Yeah

Tim Ferriss 48:43 ... stoic philosophy, of, um, what is the term in Latin? It, uh, is meditate- medi-

Ryan Holiday 48:52 Oh, premeditatio malorum.

Tim Ferriss 48:54 Yeah.

Ryan Holiday 48:54 Yeah.

Tim Ferriss 48:54 Premeditatio malorum. Meditating on the, the possible evils or risks. So I have a written format fear-setting people can check out, tim.blog/ted if you wanna 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 s-

Ryan Holiday 49:16 Us talking, how, how poorly this could go. [laughs]

Tim Ferriss 49:18 How poorly this conversation with Ryan could go, and how I would possibly repair the-

Ryan Holiday 49:22 [laughs]

Tim Ferriss 49:23 ... the incredible reputational damage. Uh, around stopping just about everything. So even though I'm not seriously considering, nor do I feel compelled to say stop stopping the podcast-

Ryan Holiday 49:34 Yeah

Tim Ferriss 49:34 ... right, I would write down, like, "Stop the podcast?" What if I stop this? What if I stop-

Ryan Holiday 49:40 Yeah

Tim Ferriss 49:40 ... all involvement with real estate? What if I stopped all travel?

Ryan Holiday 49:44 Sure.

Tim Ferriss 49:44 What if I stopped... And I'll, I will go through the thought experiment of what if I completely stop these various things categorically. And when you run through the kind of so what, so what, so what, so what-

Ryan Holiday 50:00 Yeah

Tim Ferriss 50:00 ... for each of those, ultimately realize you're gonna be fucking fine-

Ryan Holiday 50:04 Yeah

Tim Ferriss 50:04 ... with all of them.

Ryan Holiday 50:05 Sure.

Tim Ferriss 50:05 And, and to that extent, I, I think that making good decisions is often negotiating with yourself. Uh, and that the, 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 th- that's not a value judgment. But if you have two people negotiating against each other and one feels like they have to do the deal-

Ryan Holiday 50:37 Yeah

Tim Ferriss 50:37 ... and the other person has a, has 20 different BATNAs, right? Best alternative to negotiated agreement, and they don't give two shits whether the deal happens or not, or at the very least, they're very comfortable walking away-

Ryan Holiday 50:50 Yeah

Tim Ferriss 50:51 ... he or she who cares the least wins.

Ryan Holiday 50:53 Yeah.

Tim Ferriss 50:54 And I, I like to cultivate the side of me that can see how little a lot of the glossy veneer aspects of life, uh, add at the end of the day to, like, the core of what you need to feel content on a regular basis. Um, so that might be a, a lot of word salad at once, but th- those are at least some of the ways that I think about it.

Ryan Holiday 51:23 No, I think that ties into, we were just talking about the Stoics. Marcus really says this thing. He says, like, "Ask yourself at every moment, is this necessary?"

Tim Ferriss 51:30 Yeah.

Ryan Holiday 51:30 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."

Tim Ferriss 51:38 Still have it. Yeah.

Ryan Holiday 51:39 Yeah. That seems like you guys are in alignment. You're like, "How, do I need this? Do I want this? What would happen if I didn't have it? Why does everyone else want it?" Uh, it seems like you're constantly questioning that.

Tim Ferriss 51:51 I am. Uh, uh, or I try to do it at regular intervals. I mean, I get caught up in the-

Ryan Holiday 51:56 Yeah

Tim Ferriss 51:56 ... slipstream and start swimming against the riptide all the time.

Ryan Holiday 52:02 Sure.

Tim Ferriss 52:02 I, I mean, I get sucked into stuff all the time. But I do very frequently take plane rides 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-

Ryan Holiday 52:27 Yeah

Tim Ferriss 52:27 ... and the better decisions that I had made and the poor decisions, uh, that I'd made, which are, which are different from good and bad outcomes.

Ryan Holiday 52:42 Yeah.

Tim Ferriss 52:42 There's like the-

Ryan Holiday 52:42 Right

Tim Ferriss 52:43 ... but just the, n- so where I made mistakes in decision-making and some of the, the sort of catastrophes and things that really caused me a lot of angst and upset. Uh, one of the corollaries is I, to the bad decisions, is that, or correlations rather, is that I, I wasn't paying attention to energetic management or, like, energy management. And I'll, I'll explain what I mean by that.

Ryan Holiday 53:17 Oh.

Tim Ferriss 53:18 So it's, it's-

Ryan Holiday 53:18 You're managing your own energy?

Tim Ferriss 53:19 It, yeah, it's pretty simple.

Ryan Holiday 53:20 Yeah.

Tim Ferriss 53:20 I mean, as I get older, I still feel like I'm in good shape.

Ryan Holiday 53:24 Yeah.

Tim Ferriss 53:24 But if I don't sleep well for two or three nights-

Ryan Holiday 53:28 Yeah

Tim Ferriss 53:29 ... life is not good-

Ryan Holiday 53:30 Right

Tim Ferriss 53:30 ... generally.

Ryan Holiday 53:31 Right.

Tim Ferriss 53:31 And that, that's a really simple example, but the, the point being when I'm considering doing a project, partnering with someone, embarking on some type of, uh, creative endeavor, the, the question that I'm trying to ask myself now is w- over the intermediate or long term, which to me could be, you know, three months [laughs] .

Ryan Holiday 53:53 Yeah.

Tim Ferriss 53:54 Uh, will this give me more energy or take away or deplete me of more energy?

Ryan Holiday 53:59 Sure.

Tim Ferriss 54:00 And-

Ryan Holiday 54:01 So it's not like the hell yes or hell no. It's like what does this do to my energy levels?

Tim Ferriss 54:06 Yeah, which are, which are closely related, but it's, but-

Ryan Holiday 54:10 Yeah

Tim Ferriss 54:10 ... some of, some of the things that give me a lot of energy are not necessarily a hell yes.

Ryan Holiday 54:15 Right.

Tim Ferriss 54:16 They're a yes, like swimming regularly.

Ryan Holiday 54:18 Yeah.

Tim Ferriss 54:19 It-

Ryan Holiday 54:19 This is a great town for that.

Tim Ferriss 54:20 It is a great town for that, yeah. Yeah, you love Barton Springs.

Ryan Holiday 54:23 Yeah, yeah.

Tim Ferriss 54:23 It's a great, great location. There are a lot of pools here. Uh, so swimming regularly, I always feel better and I always feel more energized. I feel more emotionally resilient-

Ryan Holiday 54:34 Sure

Tim Ferriss 54:35 ... after swimming.

Ryan Holiday 54:35 Yeah.

Tim Ferriss 54:36 And it's not a, a hell yes like for some people going to Burning Man for the first time or something.

Ryan Holiday 54:42 Right, sure.

Tim Ferriss 54:43 It's not that vi-

Ryan Holiday 54:44 It's not like chocolate cake, hell yes.

Tim Ferriss 54:46 No, it's not that-

Ryan Holiday 54:46 Of course I want this, yes

Tim Ferriss 54:46 ... it's not that volume of like-

Ryan Holiday 54:48 Yeah

Tim Ferriss 54:48 ... jump up and down on the table hell yes. But it is a great investment for, uh, building up energy reserves.

Ryan Holiday 54:59 Yeah.

Tim Ferriss 54:59 And so I've tried to make more and more decisions keeping that in mind.

Ryan Holiday 55:05 Yeah.

Tim Ferriss 55:05 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 gonna 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 gonna take 10 times longer-

Ryan Holiday 55:24 Yeah

Tim Ferriss 55:24 ... than it's specked out to take, and it's gonna be draining. And I, I would much rather do something smaller that doesn't have that effect on my energy, 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 the, what my-

Ryan Holiday 55:40 I think that's, I think a lot of pe- 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, I do this, uh, but I have to counteract it, but we go like, "Is this gonna make me more or less money? Is this going to make me more or less famous? Is this gonna make me more or less successful? Is this gonna make me more or less interesting?" We, we think about the outcomes.

Tim Ferriss 56:02 Yeah.

Ryan Holiday 56:03 And, and often that outcome is very far in the future and very much the, the decision isn't, it isn't like a if you do this, you are guaranteed X, you know? Or you, 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.

Tim Ferriss 56:20 Yeah.

Ryan Holiday 56:21 And I think one of the things I took from The 4-Hour Workweek and that I, I've gotten from you regularly is you tend to think more about like 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.

Tim Ferriss 56:36 Yeah.

Ryan Holiday 56:36 Think about what decisions you can make now that give you the access to the beach-

Tim Ferriss 56:40 Mm-hmm

Ryan Holiday 56:41 ... in the, in the intermediate or short term, short term. So I tend to think more like-

Tim Ferriss 56:45 As an experiment, right?

Ryan Holiday 56:46 Yes.

Tim Ferriss 56:46 Specifically.

Ryan Holiday 56:47 Yes.

Tim Ferriss 56:47 Because you may get-

Ryan Holiday 56:48 You may hate the beach, actually

Tim Ferriss 56:49 ... to the end of the line and be like, "Oh, shit, I actually don't like sailing."

Ryan Holiday 56:51 Totally.

Tim Ferriss 56:52 "And this was my made-up dream for 50 years for which I sacrificed all these other things."

Ryan Holiday 56:56 Yeah, so I think it's like is this giving me like day to day what I like more or less, you know? So that your, your ver- that's my version of the energy thing.

Tim Ferriss 57:05 Mm-hmm.

Ryan Holiday 57:05 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?

Tim Ferriss 57:12 Yeah.

Ryan Holiday 57:12 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?

Tim Ferriss 57:21 That is, that is a, I think a, a huge piece of it and if we wanted to parse that out even further, it's, it's really trying to cultivate an acute awareness of knowns and unknowns. Uh, and if you look at lifestyle design, for people who aren't familiar with the term, so lifestyle design would ef- effectively be a contrasting sort of philosophical lens through which to look at career and personal development that is juxtaposed with the, the kinda 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 dislike doing.

Ryan Holiday 58:17 Right.

Tim Ferriss 58:18 Which is not to say you're always going to enjoy doing everything.

Ryan Holiday 58:21 Yeah.

Tim Ferriss 58:21 Right? Like, I don't know many people who love doing their taxes.

Ryan Holiday 58:24 Yeah.

Tim Ferriss 58:25 There are things that you need to do, but outside-

Ryan Holiday 58:28 And no one gets exactly what they want when they're 20 years old.

Tim Ferriss 58:32 Right.

Ryan Holiday 58:32 You know what I mean?

Tim Ferriss 58:32 Yeah, very-

Ryan Holiday 58:32 Like, you have to earn and build and-

Tim Ferriss 58:34 Yeah

Ryan Holiday 58:35 ... invest and yeah.

Tim Ferriss 58:35 Yeah, there is a, there is a period of, uh, testing that goes on to determine where you are particularly adept, uh, looking at, we don't, we don't have to do a rehash of, of, of the book, but suffice to say there are ways that you can test the, 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 ve- that is a very contin- that is a theory that is contingent on many things being accurate.

Ryan Holiday 59:14 Yeah.

Tim Ferriss 59:15 And in my experience, effective lifestyle design is effective testing, uh, and awareness. Investing is, for me at least, has, 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, don't pay attention to. So if we're looking at, for instance, living in New York City-

Ryan Holiday 59:41 Yeah

Tim Ferriss 59:41 ... versus living in Austin, someone might say, "Well, I'm just going to live here for another 10 years."

Ryan Holiday 59:45 Yeah.

Tim Ferriss 59:46 "I'm going to have these following promotions in my investment banking job and then I'm gonna move to Hudson Valley."

Ryan Holiday 59:53 Yeah.

Tim Ferriss 59:53 "I'm gonna move to Santa Barbara. I'm gonna move to..." And then live the good life.

Ryan Holiday 59:57 Sure you will.

Tim Ferriss 59:58 Right. Yeah. S- so you've, that, if that is your life plan, like let's spend some time developing experiments to prove or disprove that-

Ryan Holiday 1:00:10 Yeah

Tim Ferriss 1:00:10 ... before you dedicate the next 20 years to it, but people will very often spend more time planning their, their Memorial Day weekend than they will speccing out tests.

Ryan Holiday 1:00:19 Right.

Tim Ferriss 1:00:20 So if you look at, so, so A, is there anything in your historical record to suggest that you will be able to walk away from something like that?

Ryan Holiday 1:00:28 Right.

Tim Ferriss 1:00:29 Anything.

Ryan Holiday 1:00:29 Yeah.

Tim Ferriss 1:00:30 If you are type A, right?

Ryan Holiday 1:00:31 Yeah.

Tim Ferriss 1:00:32 Uh, and by definition in that circumstance, you're probably type A.

Ryan Holiday 1:00:36 Yeah.

Tim Ferriss 1:00:37 And, uh, there are many, many, many, many faulty assumptions.

Ryan Holiday 1:00:42 Yeah.

Tim Ferriss 1:00:43 So I, I think that I ha- 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.

Ryan Holiday 1:01:00 Yeah.

Tim Ferriss 1:01:00 Therefore, I tr- I spend a lot of my time developing experiments and that's, that's my constant framework. Like, how can I be sure that I know X?

Ryan Holiday 1:01:12 Yeah.

Tim Ferriss 1:01:12 Which, you know, relates to in 2015 walking away from startup investing 'cause 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, Shopify, Uber, et cetera, it's taking 7 to 12 years-

Ryan Holiday 1:01:26 Yeah

Tim Ferriss 1:01:27 ... to come to fruition. And your final tally is not known until you've liquidated all of your holdings effectively.

Ryan Holiday 1:01:35 Yeah.

Tim Ferriss 1:01:35 I mean, it's a little more complicated than that-

Ryan Holiday 1:01:36 Yeah

Tim Ferriss 1:01:37 ... but, but not by much. So even though on paper- And also in exits, it would, I could convince myself that I am good at this, and people tell me I'm good at this. That remains to be seen.

Ryan Holiday 1:01:53 Yeah.

Tim Ferriss 1:01:54 Right? And so I stopped. Uh, and-

Ryan Holiday 1:01:57 And the larger assumption, just because you're good at something does not mean you have to keep doing it for the rest of your life.

Tim Ferriss 1:02:03 Yeah. There are many things I'm good at that I shouldn't do at all.

Ryan Holiday 1:02:06 Yeah.

Tim Ferriss 1:02:06 And, uh, it's, I think it's, it's, it's challenging for anyone, myself included, to shift gears. If y- 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, that, that is a challenging situation-

Ryan Holiday 1:02:25 Yeah

Tim Ferriss 1:02:25 ... for, I think, just about anyone, and certainly has been challenging for me. But the, the, the parachute, right, the, the safety net is realizing that for almost anything you can leave and come back.

Ryan Holiday 1:02:42 Yeah.

Tim Ferriss 1:02:42 Almost anything. And, uh, 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-

Ryan Holiday 1:03:00 That's the ultimate leverage

Tim Ferriss 1:03:01 ... that's, that is, that is a, a huge hurdle that you-

Ryan Holiday 1:03:06 Yeah

Tim Ferriss 1:03:06 ... need to be able to pass.

Ryan Holiday 1:03:06 Yeah.

Tim Ferriss 1:03:06 But if you are really good and dedicated to your craft or crafts, could be a combination of, of unusual crafts, right?

Ryan Holiday 1:03:13 Right.

Tim Ferriss 1:03:14 You might be a quant who's also really good at writing and then you have a newsletter.

Ryan Holiday 1:03:17 Sure.

Tim Ferriss 1:03:17 It could be an unusual combination of traits, like Warren Buffett and public speaking and writing-

Ryan Holiday 1:03:21 Sure

Tim Ferriss 1:03:22 ... or Jeff Bezos and writing, entrepreneurship, et cetera. You can always come back.

Ryan Holiday 1:03:27 Right. Right.

Tim Ferriss 1:03:28 It's, so I try to keep that in mind when making a lot of my decisions.

Ryan Holiday 1:03:33 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, like, I, I, I was thinking as we were talking about the Stoics more, like, one of the things that sort of weaves its way through, I think, the thinking you're, you're giving, and I know I gave you one of these, but the-

Tim Ferriss 1:03:49 Yeah

Ryan Holiday 1:03:49 ... the Memento Mori. Like, like, part, 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-

Tim Ferriss 1:03:55 Yeah

Ryan Holiday 1:03:55 ... you only get one life.

Tim Ferriss 1:03:56 Yeah.

Ryan Holiday 1:03:56 And one of the reasons I think you're always questioning the... Like, it, it seems like part of your fear setting thing is, like, what if I die? Like, does any of this-

Tim Ferriss 1:04:03 Yeah

Ryan Holiday 1:04:03 ... matter?

Tim Ferriss 1:04:04 Yeah.

Ryan Holiday 1:04:04 Do you know what I mean?

Tim Ferriss 1:04:05 Yeah, the costs of inaction.

Ryan Holiday 1:04:07 Yeah.

Tim Ferriss 1:04:07 Right? I think, um, that thinking very carefully about the costs of inaction and telescoping out 6 months, 12 months, 18 months, you know, what effect does continuing to do what you do have on you and your loved ones from a financial, emotional, physical perspective, right?

Ryan Holiday 1:04:28 Yeah.

Tim Ferriss 1:04:29 And, uh, I think about death all the time, and it's not, um, a morbid, sullen exercise for me. It, it's, uh, this becomes easier the older you get because friends start dying, family members die, and you realize this is not an indefinite l- lease.

Ryan Holiday 1:04:51 Yes.

Tim Ferriss 1:04:51 Like, you have-

Ryan Holiday 1:04:52 Or that it is a lease. You don't own it.

Tim Ferriss 1:04:54 Yeah. It is a lease.

Ryan Holiday 1:04:55 Yes. Yes.

Tim Ferriss 1:04:55 And that having the, I don't want to call it time pressure, but awareness of that impermanence, for me, I find, uh, this might sound strange, but, like, greatly encouraging because it drives a sense of urgency.

Ryan Holiday 1:05:17 Yeah.

Tim Ferriss 1:05:18 Uh, or at least time sensitivity to a lot of my decisions. And, uh, s- so that's on one hand sort of prizing this fleeting-

Ryan Holiday 1:05:30 Yeah

Tim Ferriss 1:05:30 ... non-renewable resource that is time and realizing that doesn't matter how much money you're willing to pay on your deathbed, you're not gonna be able to buy back more time.

Ryan Holiday 1:05:39 Right.

Tim Ferriss 1:05:40 And then simultaneously, uh, I guess meditating is the best way to put it, or contemplating how little a lot of this matters or all of it matters.

Ryan Holiday 1:05:52 Yeah.

Tim Ferriss 1:05:53 Insomuch as, you know, as Naval Ravikant once said to me, he's like, "Yeah, we're just a bunch of monkeys on a spinning rock."

Ryan Holiday 1:05:58 Mm-hmm.

Tim Ferriss 1:05:58 And, uh, spending time, this is gonna sound so highfalutin, but whatever, reading about the cosmos or contemplating as, uh, I believe it was Ed Cook, an incredible, uh, memory competitive champion and, uh, entrepreneur. Memrise is his company, uh, M-E-M-R-I-S-E, and coach, also writer, ha- had said to me, you know, he would... And BJ, BJ Miller, 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-

Ryan Holiday 1:06:41 Yeah

Tim Ferriss 1:06:41 ... 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.

Ryan Holiday 1:06:51 Yeah.

Tim Ferriss 1:06:52 Right?

Ryan Holiday 1:06:52 Right.

Tim Ferriss 1:06:52 And to just sort of contemplate that-

Ryan Holiday 1:06:55 Yeah

Tim Ferriss 1:06:55 ... when you're freaking out because you have some problem with Amex-

Ryan Holiday 1:06:58 Right

Tim Ferriss 1:06:58 ... or there's some disagreement and, like, somebody badmouthed you at work or whatever it is. You're like-

Ryan Holiday 1:07:08 Right

Tim Ferriss 1:07:09 ... "Okay, to-"

Ryan Holiday 1:07:11 Number one or number two on the New York Times bestseller list or, you know, all the things that we-

Tim Ferriss 1:07:15 Who cares?

Ryan Holiday 1:07:16 Yes.

Tim Ferriss 1:07:16 All dust.

Ryan Holiday 1:07:17 Yes.

Tim Ferriss 1:07:17 Right? As, as our friend Marcus would say.

Ryan Holiday 1:07:18 Yes.

Tim Ferriss 1:07:19 Like, all dust. Like, it, nobody gives a shit.

Ryan Holiday 1:07:21 Right.

Tim Ferriss 1:07:21 Like, it's all-

Ryan Holiday 1:07:22 Not even you in the future-

Tim Ferriss 1:07:23 Yeah

Ryan Holiday 1:07:23 ... will give a shit.

Tim Ferriss 1:07:24 It's, yeah. It's, it's, it's all going to be just completely irrelevant. And, uh, so the, so holding those two in my mind, uh, has been a practice. Uh, and, um, I do think about death a lot and, um, there was, um- Person featured in, I think it was Tribe of Mentors, Muneeb Ali, who's involved, uh, very heavily involved with cryptocurrency. Very, very smart guy. Might, um, maybe better put, blockchain. Very smart guy. And it's, it's funny to me how certain things stick and certain things don't stick.

Ryan Holiday 1:08:06 Yeah.

Tim Ferriss 1:08:06 Or certain things have like a time release, right? So I read this and I was like, "Oh, that's interesting."

Ryan Holiday 1:08:10 Yeah.

Tim Ferriss 1:08:10 And then months later it sort of c- resurfaced, and I've thought about it a lot since, which was he'll, he, he will routinely ask himself when he's o- overwhelmed or feeling scattered, you know, "How much would I pay f- to relive this experience like 20 years from now, 30 years from now, 40 years from now?" And I'm paraphrasing-

Ryan Holiday 1:08:30 Yeah

Tim Ferriss 1:08:30 ... so it's not, it's 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, it's not the professional successes or the glamour shots. It's usually something very simple.

Ryan Holiday 1:08:50 Right.

Tim Ferriss 1:08:51 Like wa-

Ryan Holiday 1:08:52 It's the moments of stillness and quiet-

Tim Ferriss 1:08:54 Yeah

Ryan Holiday 1:08:55 ... and peace and relationships.

Tim Ferriss 1:08:55 Like wake, yeah, waking, waking up in bed with my girlfriend on a, like a beautiful, sunny day, and like patting the, patting the bed and having my dog jump up.

Ryan Holiday 1:09:03 Right.

Tim Ferriss 1:09:04 And having a little snuggle fest. It's, it's very, it sounds so cheesy. Like the 20-year-old Tim would just be vomiting all over-

Ryan Holiday 1:09:09 Right

Tim Ferriss 1:09:09 ... himself right now. But nonetheless, twen- 20-year-old Tim was a pretty miserable fuck.

Ryan Holiday 1:09:13 [laughs]

Tim Ferriss 1:09:14 So, uh, I feel like I've improved on that front. And asking yourself like, "All right. If, 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?"

Ryan Holiday 1:09:30 Yeah.

Tim Ferriss 1:09:30 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-

Ryan Holiday 1:09:50 Right

Tim Ferriss 1:09:50 ... on doing something that, say, takes you away from those people.

Ryan Holiday 1:09:52 Right, or agreeing to something because you might get some honor or-

Tim Ferriss 1:09:56 Mm-hmm.

Ryan Holiday 1:09:57 You know-

Tim Ferriss 1:09:57 You know-

Ryan Holiday 1:09:58 Go ahead.

Tim Ferriss 1:09:58 Can may I just add one more thing?

Ryan Holiday 1:09:59 Yeah.

Tim Ferriss 1:09:59 Which is I really think that even if you keep all your money in a mattress, studying good investors is worth a lot.

Ryan Holiday 1:10:10 Yeah.

Tim Ferriss 1:10:11 Not necessarily in financial return, but in temporal return, right? In like, in, in, in how you think about time.

Ryan Holiday 1:10:18 Yeah.

Tim Ferriss 1:10:18 Because humans overall are very sloppy, uh, I'm no mathematician, so I'll put myself in the same category, when it comes to thinking about probabilities.

Ryan Holiday 1:10:30 Yeah.

Tim Ferriss 1:10:31 Like probabilistic thinking is not, it's not a strong suit for humans. And, uh, so you might hear like, "Oh my God, there's a room of 300 people," and like-

Ryan Holiday 1:10:41 Yeah

Tim Ferriss 1:10:41 ... "These two people have the same birthday. That's crazy."

Ryan Holiday 1:10:43 Yeah.

Tim Ferriss 1:10:44 But like mathematically speaking, it's not that crazy.

Ryan Holiday 1:10:46 Right.

Tim Ferriss 1:10:47 Um, and in fact, at some point it becomes totally expected, right?

Ryan Holiday 1:10:49 Yeah.

Tim Ferriss 1:10:49 And similarly, developing a basic sort of mathematical literacy with respect to investing, which I think, uh, 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, so it, it... And it was the same year. He had a good math teacher, and I had one who was-

Ryan Holiday 1:11:12 Right

Tim Ferriss 1:11:12 ... just a ballbuster, and you can see how we split in different directions. But I've, I have a deep-seeded insecurity when it comes to math. Nonetheless, studying investing has helped me to develop, uh, s- my understanding of certain concepts like expected value. So if you think that you are going to, you could make $100,000 or a million dollars 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?

Ryan Holiday 1:11:50 Yeah.

Tim Ferriss 1:11:50 Well, it depends a lot on the probability of that happening.

Ryan Holiday 1:11:53 Right.

Tim Ferriss 1:11:53 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."

Ryan Holiday 1:12:06 Right.

Tim Ferriss 1:12:06 That could very, very deeply influence how you make that decision-

Ryan Holiday 1:12:10 Right

Tim Ferriss 1:12:10 ... about how you're gonna spend your time over the next 6 to 12 months.

Ryan Holiday 1:12:12 Right.

Tim Ferriss 1:12:13 Right?

Ryan Holiday 1:12:13 Sure.

Tim Ferriss 1:12:14 'Cause if there's a sure bet, it's a $50,000 return, but it's 80, 90% likely to happen-

Ryan Holiday 1:12:19 It's worth more

Tim Ferriss 1:12:20 ... it's worth more, right? If you're thinking about it in a structured way. And, um, there are some really fun books on investing that don't necessarily touch on this in exactly. One is called, um, More Money Than God. It's about hedge fund investors.

Ryan Holiday 1:12:35 Okay.

Tim Ferriss 1:12:35 And it's a super fun book. It's kinda like Liar's Poker.

Ryan Holiday 1:12:37 Yeah.

Tim Ferriss 1:12:37 But instead of purely bonds, it's-

Ryan Holiday 1:12:40 Yeah

Tim Ferriss 1:12:41 ... it's all sorts of different characters and types of investing. Uh, 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. Uh, math is too scary. Just like how to think probabilistically, um, because life is probabilities.

Ryan Holiday 1:13:08 Yeah.

Tim Ferriss 1:13:09 And, uh, whenever, for instance, and I'm, I'm dragging myself into the deep end a little bit here because, um, I'm not a scientist, but if you, if you look at science and studies, you will very... 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-

Ryan Holiday 1:13:36 Yeah

Tim Ferriss 1:13:36 ... medicine and science. People get so confused about these things, and people end up dying and making bad decisions-

Ryan Holiday 1:13:41 Right

Tim Ferriss 1:13:41 ... or, and choosing quacky doctors without this basic literacy. There's a, there's a great book called Bad Science.

Ryan Holiday 1:13:48 Yeah.

Tim Ferriss 1:13:48 ... by Ben Goldacre that I recommend to everybody. I, I excerpted some of those chapters in the appendix of The 4-Hour Body-

Ryan Holiday 1:13:55 Wow

Tim Ferriss 1:13:55 ... 'cause I think it's so important. Um, but s- suffice to say, if, if someone says, "These studies prove X," it's not really true.

Ryan Holiday 1:14:05 Right.

Tim Ferriss 1:14:06 Like, they're, they're, they suggest at a high probability-

Ryan Holiday 1:14:08 They suggest for a very small, uh, uh, sample size-

Tim Ferriss 1:14:13 Yeah

Ryan Holiday 1:14:13 ... it had a slightly, uh, greater than average probability-

Tim Ferriss 1:14:17 Yeah

Ryan Holiday 1:14:17 ... that, uh, yeah.

Tim Ferriss 1:14:18 And it, and it could be an incredibly strong signal.

Ryan Holiday 1:14:20 Right.

Tim Ferriss 1:14:20 But it is not 100% certainty.

Ryan Holiday 1:14:22 Right.

Tim Ferriss 1:14:22 So-

Ryan Holiday 1:14:23 It might never have been replicated.

Tim Ferriss 1:14:24 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 start thinking in terms of probabilities.

Ryan Holiday 1:14:39 Yeah.

Tim Ferriss 1:14:40 Right? Because to remove all risk is a fool's errand.

Ryan Holiday 1:14:44 Yeah.

Tim Ferriss 1:14:44 I, I spent a lot of time trying to do that, and chasing that tail end of, like, 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, right? You'd, you'd just have to lock yourself in solitary confinement in a box.

Ryan Holiday 1:15:00 Right.

Tim Ferriss 1:15:01 And it, it would be no life worth living. But, uh, this, this has been a real game changer for me, even though I don't, I don't do... I mean, I invest. Anyone who's alive invests.

Ryan Holiday 1:15:12 Right.

Tim Ferriss 1:15:12 I think that's, you're investing time, energy, capital. Like, you're choosing where to allocate resources.

Ryan Holiday 1:15:19 Sure.

Tim Ferriss 1:15:19 Um, but, uh, I read all these books on investing, uh, or Think Twice is another one that's good, uh, related to cognitive biases. Uh, not because I'm playing the stock market.

Ryan Holiday 1:15:34 Yeah.

Tim Ferriss 1:15:34 At all. All right? That's not why I'm reading these books.

Ryan Holiday 1:15:36 Yeah.

Tim Ferriss 1:15:36 I'm reading it because it, it helps me to think in a more structured way about, uh, good decision-making. Yeah.

Ryan Holiday 1:15:46 Yeah. I, I wanna come back to the study and things, 'cause I had a question for you. But I, I was, when we were talking about sort of happiness, money, um, young, old, um, uh, Sep Kamvar, who we both know.

Tim Ferriss 1:15:57 Yeah. Brilliant guy.

Ryan Holiday 1:15:58 Uh, he, he did this massive study where he scraped all these blog posts about, like, and social media posts about what people were saying. 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.

Tim Ferriss 1:16:28 Mm.

Ryan Holiday 1:16:28 And so, uh, we can make a lot of decisions. It's like we know objectively that's where we're gonna end up, that's what we're gonna care about, but then we spend most of our lives focusing on piling up accomplishments.

Tim Ferriss 1:16:40 Mm-hmm.

Ryan Holiday 1:16:40 Do you know what I mean?

Tim Ferriss 1:16:41 Yeah. I do.

Ryan Holiday 1:16:42 And, and sort of knowing... I, I think that idea of thinking about what you're gonna care about if you're lucky enough to be old, get old-

Tim Ferriss 1:16:49 Yeah

Ryan Holiday 1:16:49 ... is really important, 'cause it puts the things that feel important in perspective.

Tim Ferriss 1:16:54 Yeah. It d- it, uh... Sep's an, an amazing computer scientist.

Ryan Holiday 1:16:59 Yeah.

Tim Ferriss 1:16:59 And just a sweet heart of a guy.

Ryan Holiday 1:17:01 Totally.

Tim Ferriss 1:17:02 Uh, and this, this observation that you just made, uh, that, uh, in younger years, let's just call it 20s and maybe 30s or, or early 30s, "I am happy. I'm doing great because," and then accomplishment.

Ryan Holiday 1:17:22 Yeah.

Tim Ferriss 1:17:23 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?

Ryan Holiday 1:17:40 Yeah.

Tim Ferriss 1:17:41 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-

Ryan Holiday 1:17:47 No, people aren't being polled. This is-

Tim Ferriss 1:17:49 Oh, this is-

Ryan Holiday 1:17:49 ... unsolicited-

Tim Ferriss 1:17:50 Oh, this is from blog posts

Ryan Holiday 1:17:50 ... statements that you make-

Tim Ferriss 1:17:51 Okay

Ryan Holiday 1:17:51 ... uh, on social media.

Tim Ferriss 1:17:52 Okay. I got it.

Ryan Holiday 1:17:53 Yeah, yeah.

Tim Ferriss 1:17:53 So, so that, that answers that. These, like, to me, the... It's important to me at least to immediately not be a cynic, but to ask a lot of questions so I understand the nature of what-

Ryan Holiday 1:18:07 Sure

Tim Ferriss 1:18:07 ... is being implied, right?

Ryan Holiday 1:18:08 Yeah.

Tim Ferriss 1:18:08 'Cause could it be that the people who experience or value connectedness in later years sort of paid their dues-

Ryan Holiday 1:18:18 Had the accomplishments

Tim Ferriss 1:18:18 ... cut their, cut their teeth.

Ryan Holiday 1:18:19 Yeah.

Tim Ferriss 1:18:20 And therefore they're like, "All right. I'm on my second home. Uh, I have checked off all these rungs on hi- Maslow's hierarchy of needs."

Ryan Holiday 1:18:29 Sure.

Tim Ferriss 1:18:30 "Great. Now I can focus on-

Ryan Holiday 1:18:31 Yeah

Tim Ferriss 1:18:32 ... you know, self-actualization." Uh, or does it happen independently? I think, I think it, if I had to place a bet, I would imagine that it probably happens somewhat independently as you become more aware of your mortality.

Ryan Holiday 1:18:42 Yes.

Tim Ferriss 1:18:43 And-

Ryan Holiday 1:18:43 I think that's what it is.

Tim Ferriss 1:18:45 Uh, but the, uh, this is another facet that I think underscores how beneficial it is to, to study good investors, and that is, uh, or good scientists, but it's, it's, I think that investing has more sex appeal for a lot of people. Uh, the distinction between correlation and causation.

Ryan Holiday 1:19:05 Yeah.

Tim Ferriss 1:19:07 Right? And, or is there a third... Is it possible there's a third or fourth factor-

Ryan Holiday 1:19:13 Yeah

Tim Ferriss 1:19:13 ... that could be causal? Uh, 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-

Ryan Holiday 1:19:25 Right

Tim Ferriss 1:19:25 ... report a higher level of wellbeing and-

Ryan Holiday 1:19:28 Yeah

Tim Ferriss 1:19:28 ... lower blood pressure. Therefore, the headline in, uh, some-

Ryan Holiday 1:19:33 Huffington Post is, is-

Tim Ferriss 1:19:34 Yeah. Wherever, right?

Ryan Holiday 1:19:35 Yes.

Tim Ferriss 1:19:35 Therefore, uh, yoga decreases blood pressure and so on.

Ryan Holiday 1:19:39 Right.

Tim Ferriss 1:19:39 Wait a second. Where was this done?

Ryan Holiday 1:19:42 Yeah.

Tim Ferriss 1:19:42 It's like, oh, San Diego. Okay.

Ryan Holiday 1:19:43 Yeah.

Tim Ferriss 1:19:44 What's the median household income? Okay, what else are they doing? Oh, they're seeing, they have a PPO instead of HMO, and they're seeing- ... some of the best doctors in the country.

Ryan Holiday 1:19:53 Yeah.

Tim Ferriss 1:19:53 Oh, okay. All right. And you begin to realize, uh, how tricky it can be to establish a causation, right?

Ryan Holiday 1:20:02 Yeah.

Tim Ferriss 1:20:02 Um, but I, 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.

Ryan Holiday 1:20:34 Yeah.

Tim Ferriss 1:20:35 And that's exciting for me because to me, that says op- that spells opportunity. If, if it's possible, for instance, and, um, you know, 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.

Ryan Holiday 1:20:49 Yeah.

Tim Ferriss 1:20:50 And if we look at some of these morga- like mortgage-backed securities, uh, short bets-

Ryan Holiday 1:20:55 Yeah

Tim Ferriss 1:20:55 ... that ended up producing these multi-billion dollar windfalls.

Ryan Holiday 1:20:59 Right.

Tim Ferriss 1:21:00 Uh, some of, some of those positions were based on, uh, looking at publicly available data and drawing some pretty common sense conclusions.

Ryan Holiday 1:21:12 Right.

Tim Ferriss 1:21:13 Right? It wasn't-

Ryan Holiday 1:21:14 Well, we think, we think-

Tim Ferriss 1:21:15 ... AI, proprietary AI from, you know, the, 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.

Ryan Holiday 1:21:34 Right.

Tim Ferriss 1:21:34 Right? Like, if you ask a venture capitalist if things are gonna turn south, it's they're highly, highly, highly, highly, highly subconsciously or consciously-

Ryan Holiday 1:21:43 Sure

Tim Ferriss 1:21:43 ... disincentivized from saying things are gonna go south because-

Ryan Holiday 1:21:46 Unless they have a large bet that things are gonna go south.

Tim Ferriss 1:21:48 Which they would have to have-

Ryan Holiday 1:21:50 Yeah

Tim Ferriss 1:21:50 ... uh, either outside of venture capital-

Ryan Holiday 1:21:52 Right, sure

Tim Ferriss 1:21:53 ... so it wouldn't be correl- it wouldn't be associated with their fund. Or they'd have to have some, like, counter-cyclical startup bet, which they may or may not, right? Conversely, if you're looking at, say, hedge fund investors, I know that's a term that's fallen out of favor, but-

Ryan Holiday 1:22:08 Yeah

Tim Ferriss 1:22:08 ... nonetheless, people who can place both long bets-

Ryan Holiday 1:22:11 Yeah

Tim Ferriss 1:22:11 ... we think this is going up or growing, and short bets, we think this is going down, uh, or decreasing in value, their view of the world's gonna be very different-

Ryan Holiday 1:22:20 Sure

Tim Ferriss 1:22:20 ... in what they're willing to talk about, right?

Ryan Holiday 1:22:22 Yeah.

Tim Ferriss 1:22:23 Uh, so they're... I find it incredibly, uh, both really exciting and i- entirely terrifying that there are so many blind spots.

Ryan Holiday 1:22:33 Well, Tyler Cowen talks about this with the, the three-point revolution in the NBA. Like-

Tim Ferriss 1:22:38 Mm

Ryan Holiday 1:22:38 ... three-pointer has always been worth more than two-pointers.

Tim Ferriss 1:22:41 Right.

Ryan Holiday 1:22:41 And so you can miss a higher percentage of them and still score more points, right?

Tim Ferriss 1:22:46 Mm-hmm. Yeah.

Ryan Holiday 1:22:46 Like, so, so, you know, a percentage making of a, of a three-pointer is on average worth more than a, what, than a field goal.

Tim Ferriss 1:22:54 Yeah.

Ryan Holiday 1:22:54 Right? And he's like, "Literally people were paid millions of dollars, million, billions of fans watch this game-

Tim Ferriss 1:23:00 Yeah

Ryan Holiday 1:23:00 ... and no one was like, 'Hey, why don't we shoot more three-pointers?'"

Tim Ferriss 1:23:03 Right.

Ryan Holiday 1:23:03 You know? And, and then-

Tim Ferriss 1:23:04 Yeah

Ryan Holiday 1:23:04 ... somebody did it, and the entire game changes.

Tim Ferriss 1:23:07 Yeah. Wonder who that was. Like Steph Curry or someone comes in and just-

Ryan Holiday 1:23:10 But, like, that it was even not just, like, within our lifetime, like it was within the last half decade-

Tim Ferriss 1:23:15 Yeah, yeah

Ryan Holiday 1:23:15 ... that, that the game fundamentally changed.

Tim Ferriss 1:23:18 Yeah.

Ryan Holiday 1:23:18 And it's not like, it's not like they figured out the physics of shooting a three-pointer better. Like-

Tim Ferriss 1:23:22 Yeah

Ryan Holiday 1:23:23 ... just now there's incentives and so people shoot more three-pointers, and they make more. And the, a game literally that millions of people watch, just nobody noticed this thing right in front of them.

Tim Ferriss 1:23:32 Yeah, yeah. Or it's like you look at certain inventions, right? Wheels on luggage. Like-

Ryan Holiday 1:23:37 Yeah, I've heard you talk about this one

Tim Ferriss 1:23:38 ... for God's, for God's sake, you know?

Ryan Holiday 1:23:39 Yeah. Right.

Tim Ferriss 1:23:39 How long did that take? And it's, it's, it's sitting there right in plain sight.

Ryan Holiday 1:23:43 Yeah.

Tim Ferriss 1:23:43 And, uh, I think there are still, I mean, practically infinite number of opportunities like that. And for me at least, it all comes from just a better set of questions. And, um, if you look at the process behind or that has been developed at places like IDEO or Frog Design or these, these different product development, industrial design firms, a lot of it's asking questions, right?

Ryan Holiday 1:24:10 Yeah.

Tim Ferriss 1:24:11 And trying to not just test the assumptions, but find the assumptions, identify the assumptions-

Ryan Holiday 1:24:20 Yeah

Tim Ferriss 1:24:20 ... in something like grocery cart design.

Ryan Holiday 1:24:22 Yeah.

Tim Ferriss 1:24:22 Right? Like, what have we just completely taken for granted because this is the way it is and this is the way it's always been?

Ryan Holiday 1:24:27 Yeah.

Tim Ferriss 1:24:28 And, uh, I find that really exciting when it comes to, uh, it... And I like to try to ask a lot of those questions. Uh, there's a, there's a great doc, documentary called Objectified-

Ryan Holiday 1:24:44 Yeah

Tim Ferriss 1:24:45 ... which is about a lot of this. Uh, and then, uh, I saw it a long time ago, made by the same filmmakers, I believe, who did a film, uh, called Helvetica about-

Ryan Holiday 1:24:54 Such a good documentary. Yeah.

Tim Ferriss 1:24:55 Yes, such a great doc.

Ryan Holiday 1:24:57 Yeah.

Tim Ferriss 1:24:57 That brings up a lot of this. And w- when I see something that doesn't make sense or doesn't feel good, doesn't work well, uh, I like to ask a, a lot of questions and also combine that with studying incentives.

Ryan Holiday 1:25:14 Yeah.

Tim Ferriss 1:25:14 Like, is there any reason besides a design blind spot that there weren't wheels on luggage earlier?

Ryan Holiday 1:25:21 Yeah.

Tim Ferriss 1:25:21 Like, is there some, is someone incentivized-

Ryan Holiday 1:25:24 Sure

Tim Ferriss 1:25:25 ... in such a way that would make that... Like, did that idea exist 30 years earlier but it never came to fru- fruition? And if so, why might that be the case? Okay, let's do that as a thought exercise.

Ryan Holiday 1:25:36 Yeah.

Tim Ferriss 1:25:37 Uh, and for instance, I remember when... Uber's a great example of this, right? I mean, I was involved with, with Uber before it was called Uber. It was UberCab LLC way back in the day in like 2008.

Ryan Holiday 1:25:49 Yeah.

Tim Ferriss 1:25:50 And, uh, we'll just refer to it as Uber for simplicity, was- Widely mocked.

Ryan Holiday 1:25:57 Yeah.

Tim Ferriss 1:25:57 I mean, it was, it was put on AngelList, which is another company I-

Ryan Holiday 1:26:00 Yeah

Tim Ferriss 1:26:00 ... I'm involved with. Angel.co if people wanna check it out. It was offered to investors and turned down, I wanna say by hundreds of investors as-

Ryan Holiday 1:26:09 Yeah

Tim Ferriss 1:26:09 ... ludicrous.

Ryan Holiday 1:26:10 Yeah.

Tim Ferriss 1:26:10 And the, the math behind some of the ridicule looked at the existing market for, I wanna say, black sedan car services-

Ryan Holiday 1:26:22 Right

Tim Ferriss 1:26:23 ... and limousines. And in that analysis, in retrospect, we can see there are a bunch of false assumptions.

Ryan Holiday 1:26:31 Right.

Tim Ferriss 1:26:31 Right? They thought it was always gonna be high priced.

Ryan Holiday 1:26:33 Yeah.

Tim Ferriss 1:26:34 Where many things start out being prototyped among the privileged.

Ryan Holiday 1:26:40 Yeah.

Tim Ferriss 1:26:40 Recycling-

Ryan Holiday 1:26:41 Yeah

Tim Ferriss 1:26:41 ... 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, of black sedan use. We only see X percent of single-digit growth.

Ryan Holiday 1:26:59 Yeah.

Tim Ferriss 1:27:00 This is a shitty business 'cause they'll-

Ryan Holiday 1:27:01 Right

Tim Ferriss 1:27:01 ... never capture more than Y percent.

Ryan Holiday 1:27:03 Right.

Tim Ferriss 1:27:04 Uh, missing the, the possibility, uh, and ultimately the reality, which was that ridesharing would c- create, ex- expand that market exponentially-

Ryan Holiday 1:27:20 Sure

Tim Ferriss 1:27:20 ... and create its own market, right? And, uh, then you look at, let's just say incentives of media coverage.

Ryan Holiday 1:27:29 Yeah.

Tim Ferriss 1:27:30 Right? Okay. At the time, and even more so now, it's in, it's very much in fashion to sort of attack anything-

Ryan Holiday 1:27:37 Sure

Tim Ferriss 1:27:37 ... that seems like it's catering to the 1%, right?

Ryan Holiday 1:27:40 Yeah.

Tim Ferriss 1:27:40 Even though it's really critical to prototype with people who are pro- price insensitive in the early stages of a lot of product development because-

Ryan Holiday 1:27:51 Sure, they can subsidize it

Tim Ferriss 1:27:52 ... if you're, if you're making one-offs-

Ryan Holiday 1:27:53 Yeah

Tim Ferriss 1:27:53 ... they're gonna be fucking expensive. And, uh, if you're testing things and there's a, it, it's very rough around the edges, you can have these rich people, exactly, subsidize the product development-

Ryan Holiday 1:28:02 Yeah

Tim Ferriss 1:28:02 ... that will ultimately lead to massive adoption.

Ryan Holiday 1:28:05 Yeah.

Tim Ferriss 1:28:06 So I find the whole thing just en- endlessly fascinating.

Ryan Holiday 1:28:11 Yeah.

Tim Ferriss 1:28:11 And I think it, it's, it's also safe to assume that at almost any given point in time, that almost everybody is getting it wrong, um-

Ryan Holiday 1:28:19 Yeah

Tim Ferriss 1:28:19 ... uh, with, with many, many, many, many, many things. Um, and that to me says that if, 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. But, but I've, I've, when I've found questions I like, I borrow those questions and I put them into an Evernote notebook-

Ryan Holiday 1:28:51 Yeah

Tim Ferriss 1:28:51 ... under investing. I'm like, 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?"

Ryan Holiday 1:29:00 Right.

Tim Ferriss 1:29:00 I write, I write those down. I'm like, wow. Like, I completely... This never would've occurred to me. Now that they've said it, it's com- it's entirely self-evident. Like, how, how did I miss that, right? And why did they not... Wait, why did they not miss it?

Ryan Holiday 1:29:13 Yeah.

Tim Ferriss 1:29:13 I really think about these things, and over time you can develop this, 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.

Ryan Holiday 1:29:32 Well, that, that actually ties into what I was gonna talk to you about next. It, there's a quote I, in Ego's Enemy, I, I have a quote from Bismarck where he says like, "Any fool can learn by experience. I prefer to learn by-

Tim Ferriss 1:29:42 [laughs]

Ryan Holiday 1:29:42 ... the experience of others."

Tim Ferriss 1:29:44 Right.

Ryan Holiday 1:29:44 And it, it seems like, like, so you're doing experiments, you're, you're try- you're doing trials, you're do... But you're also ha- You, 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, you read widely and deeply-

Tim Ferriss 1:30:03 Yeah

Ryan Holiday 1:30:04 ... 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've learned on a $3 used Amazon purchase.

Tim Ferriss 1:30:18 Oh, yeah. Yeah. I, I much prefer to not make my own mistakes if I can avoid it.

Ryan Holiday 1:30:23 Yeah.

Tim Ferriss 1:30:23 Recognizing that of course I'm gonna make all sorts of terrible mistakes. And to give, to give an example of the second category-

Ryan Holiday 1:30:33 Yeah

Tim Ferriss 1:30:33 ... 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, uh, I've noticed and my team has noticed some kind of odd behavior when it comes to email deliverability and open rates.

Ryan Holiday 1:30:50 Yeah.

Tim Ferriss 1:30:50 And we have a, a, by most measures, a large list. You know, 1.5 million or something like that for 5-Bullet Friday and these various newsletters. And we c- we have already looked on Google, we've already talked to some of the parties involved, but these parties have various incentives-

Ryan Holiday 1:31:08 Yeah

Tim Ferriss 1:31:08 ... that may or may not be totally aligned-

Ryan Holiday 1:31:09 Sure

Tim Ferriss 1:31:10 ... with ours. Uh, not to say they're in any way malicious or nefarious.

Ryan Holiday 1:31:15 Sure.

Tim Ferriss 1:31:15 It's just different companies, different people, different parties in a different collaboration or transaction have different incentives. So I and my team have been putting together an email, a draft email, to send to people like yourself, and it's, it's really five or six people I know already who have large lists-

Ryan Holiday 1:31:34 Yeah

Tim Ferriss 1:31:34 ... 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.

Ryan Holiday 1:31:42 Yeah.

Tim Ferriss 1:31:42 Right? 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 we are adding what we've tried.

Ryan Holiday 1:31:55 Oh.

Tim Ferriss 1:31:55 Right? Like here-

Ryan Holiday 1:31:56 Yeah

Tim Ferriss 1:31:56 ... here are the, here are the three things we've already tried to address this. Here are the results. But we're still looking for more.

Ryan Holiday 1:32:02 Yeah.

Tim Ferriss 1:32:02 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.

Ryan Holiday 1:32:14 Yeah.

Tim Ferriss 1:32:15 [laughs] Registered trademark. IM funnel, here we go. I'm not gonna do that. But the, that could turn into some type of brain trust-

Ryan Holiday 1:32:24 Sure

Tim Ferriss 1:32:24 ... with a handful of people who then exchange best practices, right?

Ryan Holiday 1:32:29 Yeah.

Tim Ferriss 1:32:29 Where everyone is currently, or most people are very siloed.

Ryan Holiday 1:32:33 Yeah.

Tim Ferriss 1:32:33 Right? So they're all trying to solve similar problems and have similar aspirations, yet even though all the newsletters that I'm, that I'm thinking of, which are, uh, owned by people like yourself and these other folks, they're all non-competitive.

Ryan Holiday 1:32:48 Yeah.

Tim Ferriss 1:32:48 They're all in different areas-

Ryan Holiday 1:32:49 Right

Tim Ferriss 1:32:49 ... 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?

Ryan Holiday 1:32:59 Yeah.

Tim Ferriss 1:32:59 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.

Ryan Holiday 1:33:08 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.

Tim Ferriss 1:33:16 Yeah.

Ryan Holiday 1:33:16 They've all sold, each one of us have 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.

Tim Ferriss 1:33:25 Yeah.

Ryan Holiday 1:33:25 And y- you could even argue that some of us are competitive. I don't think books are competitive, but, like, the point is, like, why would we compete where we don't need to compete? Let's compete on, like, making great stuff.

Tim Ferriss 1:33:37 Yeah.

Ryan Holiday 1:33:37 And let's get the other ... You know what I mean? Like-

Tim Ferriss 1:33:39 Yeah

Ryan Holiday 1:33:39 ... um, I, that's what's been amazing for me with sports, um, watching these, like, coaches give book recommendations to each other.

Tim Ferriss 1:33:46 Mm.

Ryan Holiday 1:33:46 You, like, you'd think they would be competitive, but it's like-

Tim Ferriss 1:33:48 Yeah

Ryan Holiday 1:33:49 ... actually they're getting the easy stuff out of the way, and then on Sunday they're competing.

Tim Ferriss 1:33:53 Yeah.

Ryan Holiday 1:33:53 And so just, I think people can be really precious with information, when actually you're almost always better sharing information.

Tim Ferriss 1:34:00 Yeah. And on top of that, uh, [laughs] I can very safely give my playbook for almost anything-

Ryan Holiday 1:34:11 Right

Tim Ferriss 1:34:11 ... to thousands of people.

Ryan Holiday 1:34:13 Yeah.

Tim Ferriss 1:34:14 And, uh, almost no one's gonna implement any of it. Uh, I, and, and that's not to-

Ryan Holiday 1:34:20 Right

Tim Ferriss 1:34:20 ... and that's not to say that prescriptive how-to stuff doesn't get used. It does.

Ryan Holiday 1:34:24 Right.

Tim Ferriss 1:34:25 Uh, particularly when it's simple, right? Like slow carb diet for our body. Hundreds of thousands of people, maybe millions-

Ryan Holiday 1:34:31 Right

Tim Ferriss 1:34:31 ... have used this diet successfully. It's simple, it's easy to follow. Everyone is following a diet-

Ryan Holiday 1:34:37 Yeah

Tim Ferriss 1:34:37 ... whether they choose to or not.

Ryan Holiday 1:34:39 Sure.

Tim Ferriss 1:34:40 But when it comes to, say, launching a book-

Ryan Holiday 1:34:43 Yeah

Tim Ferriss 1:34:43 ... right? And I lay out this monstrous post because I got tired of answering these questions as one-offs, right?

Ryan Holiday 1:34:50 Yeah.

Tim Ferriss 1:34:50 How to, I think it's called How to Publish a Bestseller, How to, How to Publish a Bestselling Book This Year, or something like that. How to Write a Bestselling Book This Year. I can't remember the exact title.

Ryan Holiday 1:34:58 Yeah.

Tim Ferriss 1:34:59 But it's this monster compilation post of, like, everything you can imagine related to writing, prepping, titling, publishing versus self-publishing, marketing, PR.

Ryan Holiday 1:35:12 Yeah.

Tim Ferriss 1:35:12 All of it.

Ryan Holiday 1:35:13 Yeah.

Tim Ferriss 1:35:13 Blurbs. You name it. Every stone is, is turned. And people don't do it.

Ryan Holiday 1:35:21 Yeah.

Tim Ferriss 1:35:22 It, they're just like, "No, I want the, I want the silver bullet easy answer."

Ryan Holiday 1:35:25 They're like, "Can I hire someone to do that for me?"

Tim Ferriss 1:35:27 Yeah.

Ryan Holiday 1:35:27 Yeah.

Tim Ferriss 1:35:27 And it's like, yeah, no. This is, like, I mean, maybe you can, but, like, this is my blueprint.

Ryan Holiday 1:35:33 Right.

Tim Ferriss 1:35:34 I've used it repeatedly. It works. But guess what? You still have to write a fucking good book.

Ryan Holiday 1:35:38 Right.

Tim Ferriss 1:35:39 And not to say my books are the best in the world. They're not. I mean, I mean, I would like to see they're v- I would like to think they're very useful, but I'm not Tolstoy.

Ryan Holiday 1:35:47 Yeah.

Tim Ferriss 1:35:47 I recognize there are better writers out there.

Ryan Holiday 1:35:50 Sure.

Tim Ferriss 1:35:50 Nonetheless, I take the vast majority of energy and it goes into the writing.

Ryan Holiday 1:35:56 Yeah.

Tim Ferriss 1:35:57 Uh, but man, yeah, it's, it's, uh, it's pretty wild how, how little adherence there is.

Ryan Holiday 1:36:07 Well, to go to that last bucket, and 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 for breaking down books? Like, do-

Tim Ferriss 1:36:18 Mm-hmm

Ryan Holiday 1:36:19 ... uh, where do you get the knowledge that saves you painful trial and error?

Tim Ferriss 1:36:24 I very rarely read anything that isn't recommended to me by either someone I know is very selective and snobby about book choice.

Ryan Holiday 1:36:36 Yeah.

Tim Ferriss 1:36:37 Uh, like, uh, say, Naval Ravikant or my brother.

Ryan Holiday 1:36:42 Yeah.

Tim Ferriss 1:36:43 Uh, there are certain people who already have such a tight filter that anything, anything they read has passed a very high bar.

Ryan Holiday 1:36:53 Yeah.

Tim Ferriss 1:36:53 And anything they recommend has passed an even higher bar.

Ryan Holiday 1:36:56 Yeah.

Tim Ferriss 1:36:58 Uh, that is one way I get books referred to me that I take seriously. Another would, would be triangulating multiple points of recommendation. And then, uh, very often what I'll do is, let's just say I get a book recommended from, uh, people on social media-

Ryan Holiday 1:37:19 Yeah

Tim Ferriss 1:37:19 ... or readers or listeners, and I will prompt recommendations quite often by asking for-

Ryan Holiday 1:37:25 Yeah

Tim Ferriss 1:37:25 ... the best books on a certain topic. And, uh, perhaps a year ago or two years ago, I was very interested in learning more about the contemporary art world. Not just the artists, but the gallerists and-

Ryan Holiday 1:37:40 The whole industry

Tim Ferriss 1:37:41 ... the entire industry, the market, the black box, all the craziness that, that goes into that. And this book called The Twelve Million Dollar Stuffed Shark popped up repeatedly.

Ryan Holiday 1:37:52 Yeah.

Tim Ferriss 1:37:52 I was 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, 'cause they're like, "I thought this was an Instapot."

Ryan Holiday 1:38:08 Yeah.

Tim Ferriss 1:38:08 "This is stupid." You know?

Ryan Holiday 1:38:09 "My, my, mine came damaged in the mail."

Tim Ferriss 1:38:11 Yeah. Or it's just they d-

Ryan Holiday 1:38:13 Yeah

Tim Ferriss 1:38:13 ... 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, I, I- I, I don't read the one star.

Ryan Holiday 1:38:21 Yeah.

Tim Ferriss 1:38:21 I don't read the, uh, what is the highest? Five stars?

Ryan Holiday 1:38:24 Yeah.

Tim Ferriss 1:38:25 I don't read the five stars. I will read the most helpful three and four star.

Ryan Holiday 1:38:30 Right

Tim Ferriss 1:38:31 Because I, I already have the gestalt. If, 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.

Ryan Holiday 1:38:43 Yeah.

Tim Ferriss 1:38:44 Uh, Amazon reviews can very easily be gamed, uh, on a, on a smaller level, but most authors are not gonna be-

Ryan Holiday 1:38:52 Right

Tim Ferriss 1:38:52 ... motivated enough to do it over a long period of time. So I assume if, if there are hundreds of reviews or even 100 plus, and I look at them and there are substantive reviews, that the overall star, star ranking is a, is a, is a broad indicator-

Ryan Holiday 1:39:11 Yeah

Tim Ferriss 1:39:12 ... of how much people have liked the book. Then I look at the most helpful, uh, three and four star reviews because they will, 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, like, the strength and weaknesses of-

Ryan Holiday 1:39:32 Sometimes they make you read the book better because you-

Tim Ferriss 1:39:34 Oh

Ryan Holiday 1:39:35 ... it sort of, sometimes it spoils what's in the book-

Tim Ferriss 1:39:37 Yeah

Ryan Holiday 1:39:37 ... but then you actually understand it when you're reading it.

Tim Ferriss 1:39:39 Yeah, absolutely. So I, I do that. Uh, and if, if at that point I'm interested, I download it on Kindle.

Ryan Holiday 1:39:46 Yeah.

Tim Ferriss 1:39:47 I try to do almost all of my reading on Kindle, uh, which gives me the ability to highlight very easily and then I can go to Notebook on Amazon or, uh, 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.

Ryan Holiday 1:40:13 Mm-hmm.

Tim Ferriss 1:40:13 I like looking at Goodreads for quotes from given books. If you don't like, if you don't love-

Ryan Holiday 1:40:19 Yeah

Tim Ferriss 1:40:19 ... some of the quotes from the books, that's like hating the movie trailer and then going to see a three-hour movie.

Ryan Holiday 1:40:24 Right.

Tim Ferriss 1:40:25 You're not gonna like the movie.

Ryan Holiday 1:40:26 Yeah.

Tim Ferriss 1:40:26 So I look at Goodreads and, uh, let's just say then I have the Kindle version. I will, uh, 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.

Ryan Holiday 1:40:45 'Cause life's too short?

Tim Ferriss 1:40:46 Life's too fucking short. At that, at, and, uh, Tim Urban ha- 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.

Ryan Holiday 1:41:01 Small number, yeah. Totally.

Tim Ferriss 1:41:03 So I don't have enough time left in my life if we're assuming I'm gonna die, and I've looked at the, the, the death ages, uh, of my grandparents, great-grandparents, et cetera. Then I've, like, isolated the males and I've looked at it.

Ryan Holiday 1:41:18 Yeah.

Tim Ferriss 1:41:18 So there's a pretty decent chance I'll die somewhere between 80 and 85. Right? I'm 43.

Ryan Holiday 1:41:23 Yeah.

Tim Ferriss 1:41:23 There's not that much time left.

Ryan Holiday 1:41:26 Mm-hmm.

Tim Ferriss 1:41:27 Especially if you consider sort of cognitive decline and so on.

Ryan Holiday 1:41:30 Yeah.

Tim Ferriss 1:41:30 Right? So I've got, let's just call it, who knows-

Ryan Holiday 1:41:34 Yeah

Tim Ferriss 1:41:34 ... you know, 20, 20 to 30 years left of, of, like, good book reading.

Ryan Holiday 1:41:38 You could also get hit by a bus.

Tim Ferriss 1:41:39 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.

Ryan Holiday 1:41:46 Right.

Tim Ferriss 1:41:47 Right? That I've heard of.

Ryan Holiday 1:41:48 Yeah.

Tim Ferriss 1:41:48 I don't have time for that.

Ryan Holiday 1:41:49 Right.

Tim Ferriss 1:41:49 I don't have time to read all of those.

Ryan Holiday 1:41:51 Sure.

Tim Ferriss 1:41:51 So the idea that I would pick up a book and, and think to myself, "This is pretty mediocre," and dedicate a week to reading it is pure insanity. So I, I drop a lot of books. When I looked at, and I, I put up a blog post recently looking at everything I read in 2019, all the books and-

Ryan Holiday 1:42:09 Yeah

Tim Ferriss 1:42:10 ... favorite articles, and I included all the books I bought from Amazon, and I ended up completing somewhere between 30 and 40% of all the books that already made the cut to the point-

Ryan Holiday 1:42:26 Right

Tim Ferriss 1:42:26 ... that I bought them.

Ryan Holiday 1:42:27 Sure, sure.

Tim Ferriss 1:42:28 Uh, and some of those I simply just never got around to, but a lot of them I, I stopped.

Ryan Holiday 1:42:32 I like the rule 100 pages minus your age.

Tim Ferriss 1:42:37 That's, that's the, the taste test?

Ryan Holiday 1:42:39 Yeah. That's when you quit.

Tim Ferriss 1:42:41 Oh, okay.

Ryan Holiday 1:42:41 So, so as you get older, you become more ruthless.

Tim Ferriss 1:42:44 Yeah.

Ryan Holiday 1:42:44 As you get younger-

Tim Ferriss 1:42:45 Right

Ryan Holiday 1:42:45 ... you have to give it, 'cause you don't know what the fuck you're talking about, so [laughs]

Tim Ferriss 1:42:48 Yeah, yeah.

Ryan Holiday 1:42:49 I, I like that.

Tim Ferriss 1:42:49 I like that.

Ryan Holiday 1:42:50 Yeah.

Tim Ferriss 1:42:50 I like that as a-

Ryan Holiday 1:42:51 But no, I think people are, they're like, "I paid for this." That, that's the sunk cost fallacy. They're like, "I paid for this, I should finish it." It's like-

Tim Ferriss 1:42:56 Yeah

Ryan Holiday 1:42:57 ... you hate this book, so you're gonna give it hours of your life, weeks of your life-

Tim Ferriss 1:43:01 Yeah

Ryan Holiday 1:43:01 ... just to prove that you could finish a David Foster Wallace book? I mean, like, come on.

Tim Ferriss 1:43:06 Yeah. And I've, you know, just thinking one way you could maybe trick yourself into making better decisions with books is to imagine that the book you're reading is someone you're having dinner with.

Ryan Holiday 1:43:16 Yeah.

Tim Ferriss 1:43:16 And it's like, would you really sign up for, like, five more dinners with this person?

Ryan Holiday 1:43:20 Right.

Tim Ferriss 1:43:21 If this is how you felt-

Ryan Holiday 1:43:21 Yeah

Tim Ferriss 1:43:22 ... while you were reading it?

Ryan Holiday 1:43:22 Sure.

Tim Ferriss 1:43:23 No, you wouldn't.

Ryan Holiday 1:43:24 Right.

Tim Ferriss 1:43:24 And, uh, the ca-

Ryan Holiday 1:43:25 You'd make up an excuse and you'd leave the dinner you're already at.

Tim Ferriss 1:43:28 Yeah.

Ryan Holiday 1:43:29 Yeah.

Tim Ferriss 1:43:29 Exactly. So, uh, books are also a great way to procrastinate, sort of socially validated way to procrastinate.

Ryan Holiday 1:43:39 Yeah.

Tim Ferriss 1:43:39 So I try to be ruthlessly honest with myself about that.

Ryan Holiday 1:43:49 Interesting.

Tim Ferriss 1:43:50 I, I will... There are a lot of great books out there.

Ryan Holiday 1:43:54 Yeah.

Tim Ferriss 1:43:54 I could spend all day every day reading great books-

Ryan Holiday 1:43:57 Yeah

Tim Ferriss 1:43:57 ... and produce absolutely nothing of value.

Ryan Holiday 1:44:00 Yeah.

Tim Ferriss 1:44:00 So I, uh, have increasingly tried to block out time. I have less, uh, I would say less and less time I dedicate to reading.

Ryan Holiday 1:44:12 Hmm.

Tim Ferriss 1:44:13 And, uh, I'm going to be publishing a post this week which is a public pronouncement which helps with setting policies for saying no-

Ryan Holiday 1:44:21 Yeah

Tim Ferriss 1:44:21 ... describing why I'm not gonna read any new books in, in 2020. So anything that is published in 2020-

Ryan Holiday 1:44:27 Oh, that's, my, my general rule is I almost always-

Tim Ferriss 1:44:29 Yeah

Ryan Holiday 1:44:30 ... go towards older books.

Tim Ferriss 1:44:31 Yeah. Can I say one thing?

Ryan Holiday 1:44:34 Yeah.

Tim Ferriss 1:44:34 So I'm gonna put out that post also to hold myself accountable.

Ryan Holiday 1:44:37 Right.

Tim Ferriss 1:44:37 Right?

Ryan Holiday 1:44:38 Right.

Tim Ferriss 1:44:38 Because if I get caught then reading something new, makes me look like a liar or a hypocrite, and I use public-

Ryan Holiday 1:44:46 People have to do the book burns

Tim Ferriss 1:44:47 ... public, I, oh, I definitely don't, don't, won't, won't wanna do those and don't wanna do those. So this is a, this is a single decision that makes, as, uh, Greg McKeown of Essentialism, which is a great book-

Ryan Holiday 1:44:59 Yeah

Tim Ferriss 1:44:59 ... I recommend, would say-

Ryan Holiday 1:45:01 Not new anymore, so-

Tim Ferriss 1:45:02 Not new, yeah

Ryan Holiday 1:45:02 ... people can read it.

Tim Ferriss 1:45:03 Oh, yeah. Yeah, yeah, it's a fantastic book. Uh, looking for the single decisions that remove hundreds of decisions, right? So not reading any books in 2020 removes a lot of decisions. Someone says, "Oh, my God, you should read this book. It's new." Sorry, can't do it.

Ryan Holiday 1:45:19 Right.

Tim Ferriss 1:45:19 Right? 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 for, um, in other areas of my life, I make public commitments to one or two or three friends.

Ryan Holiday 1:45:39 Right.

Tim Ferriss 1:45:39 Or to my girlfriend, so that they can hold me accountable.

Ryan Holiday 1:45:42 Sure.

Tim Ferriss 1:45:43 And, uh, I, I find great value in that. If you're trying to guard against your lesser self, I find that really useful.

Ryan Holiday 1:45:48 No, and I think, I think with, it's like, so the, the cost of a book is financial, primarily time, and then what you're gonna put in your brain. I don't wanna read things that are gonna be subsequently or very quickly proven irrelevant-

Tim Ferriss 1:46:04 Yeah

Ryan Holiday 1:46:04 ... or proven, you know, uh, incorrect or out of fashion. Like, you'd be better off sitting down and reading, uh, Shakespeare's plays, because that is g- that has not only had 500 years of cultural impact-

Tim Ferriss 1:46:20 Yeah

Ryan Holiday 1:46:20 ... but will probably have 500 more years of cultural impact. So, like, I think to, 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, or, or how many books, like, like, uh, a couple years ago, s- or a year or so ago, somebody wrote a book about Uber, and then, like, the founder was fired shortly after the book came. It's like that book is, the guy who finished that book wasted his time because it's already irrelevant by subsequent events. And I think we have a newness bias that-

Tim Ferriss 1:47:00 Yeah

Ryan Holiday 1:47:00 ... prevents us from accumulating wisdom where we could be finding it.

Tim Ferriss 1:47:04 Yeah. I, uh, I'm more interested these days in the pieces of the puzzle, and by the puzzle, we could be talking about anything, right?

Ryan Holiday 1:47:20 Sure.

Tim Ferriss 1:47:20 We could be talking about human behavior, we could be talking about the, the rise and fall of nations-

Ryan Holiday 1:47:26 Yeah

Tim Ferriss 1:47:26 ... that are kind of like the tectonic plates.

Ryan Holiday 1:47:28 Sure.

Tim Ferriss 1:47:29 I'm more interested in those because there's a bit more certainty and a higher degree of confidence in, uh, identifying and understanding some of those elements, right?

Ryan Holiday 1:47:43 Yeah.

Tim Ferriss 1:47:43 If they've been shown over and over again throughout history, or proven, or I suppose based on what I said earlier, um, you know, shown to be very likely repeatedly in, in science, right?

Ryan Holiday 1:47:57 Yeah.

Tim Ferriss 1:47:57 So this all makes me think of this, uh, quote by, I think I'm getting the name right, Donald Knuth, K-N-U-T-H, who was at, I wanna say IBM. Might be IBM, but doesn't really matter. The point being, he stopped using email at one point.

Ryan Holiday 1:48:18 Yeah.

Tim Ferriss 1:48:18 Completely stopped, and he said, for, you know, for, for people who want to stay on top of things, email is great. He's like, "But, but I wanna get to the bottom of things."

Ryan Holiday 1:48:27 Ooh.

Tim Ferriss 1:48:28 And I've thought about that a lot.

Ryan Holiday 1:48:30 Yeah.

Tim Ferriss 1:48:31 Because keeping on top of things is a losing game.

Ryan Holiday 1:48:34 Yeah.

Tim Ferriss 1:48:34 It's just-

Ryan Holiday 1:48:35 By definition.

Tim Ferriss 1:48:36 Yeah, it's a-

Ryan Holiday 1:48:36 New stuff's happening

Tim Ferriss 1:48:37 ... it's a losing game, and there are people who are gonna be more dedicated and, and obsessive with current affairs. I have no competitive advantage. I have no information advantage. I have s- I actually have a lot of information advantage.

Ryan Holiday 1:48:50 Yeah.

Tim Ferriss 1:48:50 But I have no desire or behavioral advantage with current events.

Ryan Holiday 1:48:56 Right.

Tim Ferriss 1:48:56 And it also breeds, sort of emotionally and physically, uh, a life driven by cortisol and FOMO and so on. Whereas if I'm able to discipline myself enough, which I partially do through this public accountability, to focus on studying things that have endured, um, I just feel much better in life-

Ryan Holiday 1:49:23 Sure

Tim Ferriss 1:49:23 ... in general, and I make better decisions.

Ryan Holiday 1:49:27 Yeah, look, the, they didn't have the news 250 years ago.

Tim Ferriss 1:49:31 Yeah.

Ryan Holiday 1:49:31 Do you know what I mean?

Tim Ferriss 1:49:32 Yeah.

Ryan Holiday 1:49:32 They did fine.

Tim Ferriss 1:49:33 Yeah.

Ryan Holiday 1:49:33 You know? [laughs]

Tim Ferriss 1:49:33 Yeah, yeah. Yeah.

Ryan Holiday 1:49:34 They did fine.

Tim Ferriss 1:49:35 Yeah, they did just fine. So, oh, man. Yeah, the news. Happy to miss the news. [laughs]

Ryan Holiday 1:49:44 Yeah, of course. Of course. I'd rather have, uh, truth than trivia.

Tim Ferriss 1:49:48 Yeah. So Ryan, I suppose this is the time when we say goodbye.

Ryan Holiday 1:49:51 Yep.

Tim Ferriss 1:49:52 A tearful, tearful, stoic holiday goodbye.

Ryan Holiday 1:49:56 Yeah.

Tim Ferriss 1:49:56 Uh, where can people find you online, learn more about you, and what would you like to tell people about your current projects?

Ryan Holiday 1:50:04 Uh, yeah, maybe check out Daily Stoic, which is a stoicism inspired email each morning.

Tim Ferriss 1:50:09 Mm-hmm.

Ryan Holiday 1:50:09 Um, also @DailyStoic on most platforms, and then I'm Ryan Holiday pretty much any bookstore.

Tim Ferriss 1:50:17 Across the socials and across the bookstores.

Ryan Holiday 1:50:19 That's true. Yes.

Tim Ferriss 1:50:19 Is there any, if people look at your selection of books and think to themselves, "I don't know where to start."

Ryan Holiday 1:50:25 Yeah.

Tim Ferriss 1:50:26 Where would you suggest people start with your writing?

Ryan Holiday 1:50:28 It's a good question. Um, I'd start with The Obstacle Is the Way or Stillness Is the Key. Y- y- depending, 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, which is sort of life optimization, what do I want, how do I manage, maybe I'd do Stillness.

Tim Ferriss 1:50:46 All right.

Ryan Holiday 1:50:46 Yeah.

Tim Ferriss 1:50:48 And there you have it, folks. Thank you, Ryan.

Ryan Holiday 1:50:51 Yeah. This was awesome.

Tim Ferriss 1:50:51 And, uh, as those listening probably know, this is Tim Ferriss signing off for now. Thank you for listening, and until next time, experiment well, experiment widely, and test those assumptions.