Tim Ferriss On Generosity And Dealing With Difficult People (Pt 2)

On this episode of the Daily Stoic Podcast, Ryan talks with author and early-stage technology investor/advisor Tim Ferriss on the essence of Stoicism, fear setting, and exaggerating the downside of things. How stoicism helped Tim manage the catastrophe of success and criticism and his podcast Tim Ferriss Show, which is the first business/interview podcast to exceed 100 million downloads. It has now exceeded 900 million downloads. Tim Ferriss has been listed as one of Fast Company’s “Most Innovative Business People” and one of Fortune’s “40 under 40." He is also the author of five #1 New York Times and Wall Street Journal bestsellers, including The 4-Hour Workweek and Tools of Titans: The Tactics, Routines, and Habits of Billionaires, Icons, and World-Class Performers. IG and YT: @TimFerrissX: @TFerriss✉️ Sign up for the Daily Stoic email: https://dailystoic.com/dailyemail🏛 Check out the Daily Stoic Store for Stoic inspired products, signed books, and more.📱 Follow us: Instagram, Twitter, YouTube, TikTok, FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. 📢 Share | ⚙️ Manage Subscription

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:06Ryan Holiday?

  Welcome to the Daily Stoic Podcast, where each weekday, we bring you a meditation inspired by the ancient Stoics, a short passage of ancient wisdom designed to help you find strength and insight here in everyday life. And on Wednesdays, we talk to some of our fellow students of ancient philosophy, well-known and obscure, fascinating and powerful. With them, we discuss the strategies and habits that have helped them become who they are, and also to find peace and wisdom in their actual lives. But first, we've got a quick message from one of our sponsors.

• 0:56Ryan Holiday?

  Hey, it's Ryan. Welcome to the second part of this. I thought I'd give some other Tim Ferriss facts here as I kick off the intro to the second half of the episode. Number one, you may have picked this up in the first episode, but I'm recording here at the Painted Porch. The Painted Porch bookstore would not exist without Tim Ferriss, because he's the guy I called when I was thinking about doing it. The producer of Tim's podcast is someone who I am very fond of, who helped research, I think, I think he started as my research assistant on ego is the enemy. Cristo is, was my research assistant for

• 1:39Ryan Holiday?

  many years, and then Tim poached him, and I was very happy to allow that to happen, because he's just an all-around stand-up fantastic guy, and he was destined for bigger and better things. So that's a, that's a, there's a fact there. And then, little-known encounter, Tim and I were both talking at the next web conference in Amsterdam, this would have been in 2013. We're sitting down, we're having dinner or something, and he says, hey, what are you working on? And I said, you know, I'm working on this book about Stoicism. And Tim had published maybe one of the first articles that I ever published anywhere other than my own website, Stoicism 101. Philosophy for Entrepreneurs and that had helped kicked off the book and Tim was,

• 2:23Ryan Holiday?

  you know, very interested. He said, you know, let me read it. And I sent it to him. I think if I'm remembering it right, I emailed it to him and he came down the next day and said, Hey, I'm doing this thing and I want to buy the rights to the audiobook of The Obstacles Away, which he did and used his enormous Tim Ferriss platform and helped kick that book off, made it a success. And he also did the same for The Daily Stoic and he also did the same for Ego's Enemy. I don't know if you heard about me from Tim Ferriss, but there's a good chance that you wouldn't have heard of me at all had Tim not been such an early and generous booster of all of my stuff. So I feel really grateful

• 3:08Ryan Holiday?

  and I was really excited to have this conversation. He came out to the studio. And then one other person that Tim has poached for me, that's very dear to me, my former assistant Lonnie. Tim stayed at my house, at my ranch out here in Austin when I was, I guess this would have been, when would this have been? 2016, 2017? He was, I guess it would have been early 2017. He was thinking about moving to Austin. He was here for South by and wanted somewhere to stay outside of town. So he stayed at my house while he was shopping for houses and he needed some help with some stuff and my assistant Lonnie pitched in. And now Lonnie has worked for Tim almost ever since then. So Tim is a great identifier of talent. I

• 3:53Ryan Holiday?

  guess I'm pretty good at identifying talent and Tim is a, Tim uses me as a feeder system, which I think one of the roles of a boss or a person in life is to help people go on to bigger and better things. And so I'm very happy for them and all their success. Lonnie was out here recently, actually right before Tim did his episode. Anyways, here's the second half of my conversation with the one and only Tim Ferriss. His podcast is about to exceed a billion downloads, which is just absolutely insane. You can follow him on Instagram at Tim Ferriss, follow him on Twitter at T Ferris. He's on YouTube, Tim Ferriss. And then if you haven't read The Four Hour Workweek, or The Tools of Titans, or The Four Hour Body.

• 4:38Ryan Holiday?

  With A Four Hour Chef, any of his books, you are really missing out. He signed a bunch while he was here. Great author, great dude, always thinks about things in a really unique way. And he's someone who's changed my life, not just professionally, but personally, because I have put so many of the things he talks about into practice. And that's why I was excited to have him on the podcast. And I'm excited for you to listen to this episode.

• 5:09Speaker 01

  I have a question about Stoicism for you.

• 5:11Ryan Holiday?

  All right.

• 5:11Speaker 01

  I figure, given where we are.

• 5:13Ryan Holiday?

  Yes.

• 5:13Speaker 01

  This is the right venue.

• 5:14Ryan Holiday?

  Okay.

• 5:16Speaker 01

  Of, this is a big question. So if nothing else, might immediately, choose whatever floats to the surface, of the, all of the Stoic writing that you've digested, all of the Stoic writing that you've done, all of the lessons in case studies that you've researched.

• 5:37Speaker 01

  There are certain things that people glom onto in a, not negative way, positive way. But there's things that are, I would say, predominantly memorable, right? This is true for my books as well. There's certain things that people tend not to miss.

• 5:51Ryan Holiday?

  Yes.

• 5:51Speaker 01

  Right? So like in The Four Hour Workweek, the, funny enough, one of the things that people always remember is the guest chapter by A.J. Jacobs about outsourcing his life with virtual assistants.

• 6:02Speaker 01

  But they tend to miss, and this is going to lead into my question, the filling the void chapter. Because they're like, oh, good problem to have, ha ha.

• 6:09Ryan Holiday?

  Yeah.

• 6:09Speaker 01

  Yeah, I'll worry about that when I get there. And then people really fuck it up badly and can end up in existentially pretty difficult places. What are some of the things that are really valuable that you wish people paid more attention to?

• 6:23Ryan Holiday?

  Ooh, that's a great question. By the way, I was, I was sitting out in front of Newark Airport, like, maybe a year ago.

• 6:29Speaker 01

  Just smoking your corn cob pipe?

• 6:31Ryan Holiday?

  No, just sitting there, just not waiting inside the airport.

• 6:33Speaker 01

  Yeah.

• 6:34Ryan Holiday?

  And I'm sitting there and like a car pulls up and A.J. gets out with his whole family. I was like, what the fuck is this? What are the chances? And I go, what are you working on? And he's like, oh, I'm pretending I lived during colonial times. Like, he's spent a year of his life dressing like George Washington. Like, oh, no. Yeah, he was living, living by the Constitution. That's what he was doing.

• 6:55Speaker 01

  He has, he has the most patient wife in the world.

• 6:58Ryan Holiday?

  Yeah.

• 6:59Speaker 01

  Like, the year of living biblically.

• 7:00Ryan Holiday?

  Yes.

• 7:02Speaker 01

  Also an amazing book.

• 7:03Ryan Holiday?

  So good. He's amazing. But, okay, so I, I wouldn't even fault the audience for this necessarily. I would fault myself. My initial read on, like, we see what we want to see when we're looking for stuff, right? Or we see what we need to see at that point in our life. And so my early takes on Stoicism, on Stoicism, I would say were primarily about what it could give me, right? How it can make me more resilient, how it can make me stronger, how it can make me smarter, you know, how it can make me more successful. Like, I took, I was looking at Stoicism at, through what it's been for lots of people for thousands of years, which is a form of self-help, right?

• 7:48Ryan Holiday?

  And of course, I understood that he's talking about virtue, he's talking about common good and all these things. But I would say it, it wasn't until later that I understood, so the cardinal virtues of Stoicism are courage, self-discipline, justice, and wisdom. But if you really think about it, the key virtue is justice, because it renders, it decides whether any of the other ones were worthwhile or not, right? So like courage-

• 8:16Speaker 01

  I can't wait to hear this.

• 8:17Ryan Holiday?

  Courage in pursuit of the wrong thing, or a cruel and selfish, or whatever thing, right? Courage in pursuit, like courage or discipline, or was it, like, if it's not rooted towards, like, making the world better, or doing what the Stoics would call the right thing, right? Their, their understanding of justice isn't like the legal system. It's like, what kind of person are you and what kind of code or values do you have? I think I came later than I, than I, I came later to a more full understanding of what Stoicism is asking of you, as opposed to what it can provide you. Does that make sense?

• 8:58Speaker 01

  Yeah.

• 8:59Ryan Holiday?

  And I'm just finishing this book now on Justice Should Be the Third Book in that series, so I've been thinking a lot about it more, but like- Like, almost all the Stoics were active in politics. Almost all the Stoics wrote books to share what they'd learned. Like, there was this sense, the fundamental difference between the Epicureans and the Stoics, Seneca says, is that an Epicurean basically withdraws from the stresses and complications of life into the garden, where they have fun and enjoy themselves and hang out with their friends, and a Stoic is involved in the polis, like, in public life. And so, I feel like my writing has changed and evolved, and my focus on that thing has changed and evolved more.

• 9:38Ryan Holiday?

  So, I can sometimes tell when a fan is upset with me because they're at an earlier place in the understanding of Stoicism, which I once was, and they're hearing from me now, and they don't get, you know what I mean? Like, they want to-

• 9:56Speaker 01

  It's hard for them to reconcile the two, or maybe just to take on both at the same time.

• 10:01Ryan Holiday?

  It's like, they're like, "I wanted you to give me advice on how I could be a better sociopath." You know what I mean? And you're telling me that I'm not supposed to be a sociopath, right? And that's the big one, to me. I mean, I think, I've seen this in your work, and I've always admired it. That's something I was gonna ask you. You, from the beginning, like, before your books were successful, you were donating, like, a percentage of the profits of the Four Hour Workweek to- You've always been focused on not just capturing value for yourself, but I would describe you as a generous person.

• 10:35Speaker 01

  Thanks, I appreciate that.

• 10:36Ryan Holiday?

  And to me, that is like a really key Stoic virtue, right? Or, that's part of that virtue of justice. But it's, talking about that feels kind of judgy or self-righteous. Do you know what I mean? It's easier to go like, seven Stoic strategies to be more productive.

• 10:54Speaker 01

  Yeah, it is, and I think there's, I mean, I've seen this with some of my writing as well, because it tends to be prescriptive nonfiction, and I think that one could make, to speak in the defense of the people who are focused on improving themselves, that people, and then borrowing from Arianna Huffington, at least, I've heard her say this, that you should put on your own mask before helping others.

• 11:20Ryan Holiday?

  You gotta start there, totally.

• 11:21Speaker 01

  Right? Like, put on your own oxygen mask first. And, at the same time-

• 11:28Speaker 01

  Or not at the same time, to just add something to the donation. So since the first book, you're right that a portion has been donated to different nonprofits or causes.

• 11:41Ryan Holiday?

  Yeah.

• 11:41Speaker 01

  I mean, a lot of money at this point.

• 11:43Ryan Holiday?

  Yeah, 5% of the royalties of The 4-Hour Work Week is not a small amount of money.

• 11:47Speaker 01

  Yeah, it may have been, it may be 10, it may be more than 10.

• 11:50Ryan Holiday?

  Oh, yeah, it was 10, yeah.

• 11:51Speaker 01

  Yeah, and that's been true for other books as well. I've far exceeded that. But the point that I was going to make is, part of the reason I did that, and maybe this is a very stoic thing, is you could say there are a few different motivations for that. One is to do the right thing.

• 12:11Ryan Holiday?

  Yeah.

• 12:11Speaker 01

  And to help things that I think are worth helping. Not just to help them financially, but to draw attention to them.

• 12:16Ryan Holiday?

  Sure.

• 12:16Speaker 01

  In ways that may exceed my own financial contribution.

• 12:19Ryan Holiday?

  That's how I heard about Donors Choose.

• 12:20Speaker 01

  Yeah.

• 12:21Ryan Holiday?

  Like, it was, because it was, you were saying, "I'm not donating 10% of this to charity." You said, "A specific charity."

• 12:25Speaker 01

  It's very specific.

• 12:26Ryan Holiday?

  And I said, "What charity is that?"

• 12:27Speaker 01

  Yeah. So that's one. The next is that I have just noticed as a pattern, and this could be false causality, but it's correlation at least, people who tithe in some way seem to be generally happier.

• 12:42Ryan Holiday?

  Yeah.

• 12:43Speaker 01

  Now, you could say, "Well, they're probably also, in most cases, highly religious, so couldn't it be caused by something else?" It's like saying, "Well, people who do yoga are so much healthier and have better teeth." And you're like, "Yeah, but they also tend to be of a higher socioeconomic class, so they can pay for better dental care," et cetera. So I understand the confounders here. But I will say that, from a personal experience, so let's make this the third thing, is that if you give some amount of money away, it's almost like you've created a deliberate hole in the boat that is your finances. And what that does, for me at least, is it loosens my white-knuckle grip on this thing called financial success.

• 13:26Ryan Holiday?

  Yeah.

• 13:26Speaker 01

  Because I've created an automatic release valve where some of it is disappearing. And...

• 13:34Speaker 01

  As a practice, I think that has.

• 13:37Ryan Holiday?

  You're not so precious with the resource.

• 13:39Speaker 01

  Yeah, yeah, like I am, I am assuming from the outset, there is enough, there is a sufficiency. Not saying abundance necessarily, but there's, there is a, there is, there's a sufficiency instead of a scarcity such that I can absolutely afford to give 10% off the top to other things. And that that will be a net life quality multiplier, or at least positive for me as opposed to negative. And certainly that's been my experience.

• 14:11Ryan Holiday?

  Well, this is a chance we can test the theory of Aristotle. So Aristotle says virtue isn't this thing that you are, right, that you were born as. He says virtue is like playing the flute or building houses. You become a house builder by building houses. You become a flute player by playing the flute. And his point was like, you become a courageous person by doing brave things. And he says, you become generous by doing generous acts. So do you think generosity was something you learned? Was it like a skill that you acquired? Or do you think it was just naturally always what you were or it was easy? Like, do you feel like you've gotten better at it?

• 14:46Speaker 01

  Oh, yeah, yeah, I've gotten better at it. And I'm also, I try to be very surgical with it, right? In the sense that I don't diminish automatically feel-good, let's just say philanthropy. I hate that word. Let's call it cause giving. The reason, the reason I don't like philanthropy is because it implies, right, like biophilia, like Phil loving entropy, right, like anthropology, loving humans.

• 15:17Ryan Holiday?

  Yes.

• 15:18Speaker 01

  And I don't actually, I wouldn't say default love humans. I think as, as a species, we're kind of a disaster.

• 15:25Ryan Holiday?

  Yeah.

• 15:26Speaker 01

  And invasive and very destructive.

• 15:28Ryan Holiday?

  Is preserving the environment driven by your love of humans? Or is it actually the opposite?

• 15:32Speaker 01

  So if I'm working on, say, with Amazon Conservation Team, which is one nonprofit I've vetted and feel very good about from like capital efficiency operations standpoint, that has nothing to, well, I shouldn't say, it doesn't have nothing to do with humans, but it's also like preserving ecosystems.

• 15:50Speaker 01

  But where I was going with this is I've become better and better at investing in good vehicles for accomplishing things in a nonprofit capacity, just as I have in the for-profit investing world. The way I look at them is really the same. I also do some feel-good stuff where it's very individual. It is not attempting to scale, which is sometimes important, but more often this word that's thrown around and a somewhat casual way to justify all sorts of oftentimes greedy behavior on the part of rich people who don't want to donate money, like Scrooge McDuck

• 16:34Speaker 01

  kind of stuff, Montgomery Burns, if you prefer. And I do think that from a young age, and I turned this off for a long time, but like a very deep feeler, like a very sensitive kid. So from a very young age, and I don't know if my parents encouraged this, maybe I was just traumatized by UNICEF commercials with the kids with like the flies in their eyeballs. But from a very young age, and my family, I don't come from money, right? Like, my family didn't have very much money. We had to make a lot of, you know, we can get into it, but we did not have a lot of money, suffice to say.

• 17:13Speaker 01

  And I gave, even when I was really young, and by young, I mean like, six, seven, nine, like a part of my life. Wow. If I got like a little bit of allowance or something, I would give a little bit away. Yeah. Because it felt like the right thing to do. But then there was a large period of time where I didn't do any of that. And I was like, hey, you gotta take care of number one first. Kind of Gordon Gekko, let's solve this problem first, and then I can do good later. And then for a host of reasons, I started to question that logic, both for personal fulfillment and for impact, right? Like these, sure, your net worth might be scaling, but is it scaling inflation-adjusted

• 17:58Speaker 01

  at pace with the... The problems that are also compounding, maybe not. Sure. I think in a lot of cases, the answer is early intervention with less money is better than late intervention with more money. Certainly, if that's true in medicine, it's very true with lots of the problems we see in the world, or just causes that we want to further. So for me, I wrote this blog post, god, ages ago, back when I had hair. I mean, it was probably 2007 or 2008. It's hard to believe that they're 1,000-plus blog posts. I mean, I forget about that sometimes. That was an important bridge between the book and other things that I sometimes forget about in terms of connective tissue. But I wrote this piece called, something like, "The Karmic Capitalist,"

• 18:41Speaker 01

  or "Principles of Karmic Capitalism," where I laid out some of my early thinking on this. So I took a long hiatus from that type of thinking and have come back to it. But it is a practice. It is a practice. And I found your comment on justice as sort of the, this isn't going to be the best phrasing, but the sort of master determinant of virtue or lack of virtue, when you're, right? The sort of parent virtue above others, in a sense. I've been thinking quite a lot about mother qualities.

• 19:24Speaker 01

  So for instance, what is the rate limiter? Which is slightly different than what you were saying, but if you talk to like Pavel Tsatsoula about physical fitness, so he popularized kettlebells in the United States and really knows his stuff, and for him, it's like strength first. Like strength, if you look at longevity, if you look at health span, if you look at your ability to execute other things. He's like, "Before you worry about flexibility, before you worry about mobility, before you worry about endurance, strong first." That's the name of his company, in fact. And I was like, okay, that's very, even if it's inaccurate, I happen to think it's accurate.

• 20:03Speaker 01

  It's helpful to sit and think about that for a second and interrogate that concept. And so to give you a window in, right, I do Five Bullet Fridays newsletter, every Friday goes out to a couple million people. And I capture things as I'm out in the world that are gonna later make it into Five Bullet Friday. So as we're recording this, something that I'm working on are a few quotes that are compatible that all touch on the same thing, which is laying out a hierarchy of virtues, and they word it very eloquently. Maya Angelou is one, and she talks about courage as

• 20:41Ryan Holiday?

  Yes.

• 20:42Speaker 01

  the mother virtue, because all other virtues at their testing point.

• 20:45Ryan Holiday?

  Yes.

• 20:46Speaker 01

  Right?

• 20:46Ryan Holiday?

  Yeah, and that quote, that it's all, I think there's a C.S. Lewis version of that same quote.

• 20:51Speaker 01

  There are a bunch.

• 20:52Ryan Holiday?

  That it's, and it's true, and I think I said this in the book I did on courage, that courage is the essential virtue, because you can't do any of the other things without courage, and it's true. It's just, it, the absence of justice, or the absence of it being the right thing, immediately renders whatever it is

• 21:10Speaker 01

  Yeah.

• 21:10Ryan Holiday?

  worthless. Like, if you win the Medal of Honor for the Confederacy, you know, it's like, there's something hollow about, like, there's a, there's a Lord Byron quote, he says, "Tis the cause makes all that hallos or degrades courage in its fall." Like, what it is in pursuit of, like, there's so many lonely stands you could take.

• 21:30Speaker 01

  Those old timers love their rhymes. You gotta start rhyming more.

• 21:32Ryan Holiday?

  Well, that's a poem, but that was from a poem. But the point is, like, there's a lot of lonely stands.

• 21:38Speaker 01

  Doesn't mean you can't do some stoic spoken word stuff. Anyway.

• 21:42Ryan Holiday?

  If you're, if you're taking the lonely stand, but it's wrong, you know what I mean?

• 21:47Speaker 01

  Yeah.

• 21:47Ryan Holiday?

  Or it's inact, like, it's, it's rendered worthless.

• 21:50Speaker 01

  Both of these are interesting. I mean, it's

• 21:54Speaker 01

  I'm glad that you brought up justice space because now I can think about both of these side by side.

• 21:57Ryan Holiday?

  Yeah.

• 21:58Speaker 01

  Right?

• 21:58Ryan Holiday?

  Yeah.

• 21:59Speaker 01

  And if you have a common failure mode, right? It's like if something dysregulated you, if there are certain issues that seem to repeat, if you have certain patterns with your significant other, it's like, okay.

• 22:13Ryan Holiday?

  Right.

• 22:14Speaker 01

  Is this, because justice can also be hijacked by the righteous mind.

• 22:20Ryan Holiday?

  Of course.

• 22:21Speaker 01

  You know what I mean?

• 22:21Ryan Holiday?

  Yeah, yeah.

• 22:22Speaker 01

  Right? So, but it helps to have a list, like a checklist to run through. Anyway, just wanted to say, it's, I'm really glad you brought it up because now I have a completely different lens on a list that I might have automatically ordered with courage at the top, in a sense.

• 22:38Ryan Holiday?

  I'll send you the book. I just sent it into the publisher like three days ago.

• 22:42Speaker 01

  You know what? I'm gonna, I'm gonna let people in on some inside baseball. So, part of the reason, it's done.

• 22:49Ryan Holiday?

  Yeah.

• 22:50Speaker 01

  It's done, it's finished.

• 22:51Ryan Holiday?

  It's finished.

• 22:51Speaker 01

  Hundred percent.

• 22:52Ryan Holiday?

  Hundred percent done.

• 22:52Speaker 01

  Okay, all right. Then maybe I can take a look at it because we've had this experience before.

• 22:56Ryan Holiday?

  You've sent me finished books with pages ripped out. You're like, delete this page, delete this page.

• 23:01Speaker 01

  Yeah, if I get sent a manuscript, part of the reason that I'm just like, I don't read manuscripts, is because I cannot turn off editing. And so, I will, I will do a full book edit that takes an absurd shit ton of time because I can't turn it off. And I actually, I'm not gonna be an editor, but I think I'm a better editor than a writer.

• 23:20Ryan Holiday?

  There's lower stakes.

• 23:23Speaker 01

  Lower stakes, right? I'm just like, yeah, we should definitely take out the appendix. Yeah, no, you don't really need your left toe. We can take that off because I don't have to actually deal with the consequences. But that level of detachment, which I have with very few things, it's helpful, right? Like, when I'm looking for editors, I try to embolden them to be willing to say, yeah, we should lose your left toe.

• 23:43Ryan Holiday?

  Yeah, well, that, I mean, you always, whenever you've sent me your stuff, you always say something like, what's your least favorite chapter? What chapter would you cut? Right? Where is it too long?

• 23:52Speaker 01

  If you had to cut a chapter.

• 23:53Ryan Holiday?

  You're never like, what do you like? You know?

• 23:55Speaker 01

  No, I'm like, if you had to cut 20%, what would you cut?

• 24:06Ryan Holiday?

  So to go back to generosity, the other thing I think would point out, because again, it can feel very sort of first worldly where it's like we associate generosity and money. But of course, there's many ways to be generous, right? Like, can you be just like, I think we talked about competition earlier. It's so easy to live in a world where you think things are zero sum, right? And that if somebody else gets ahead, it means it's coming at your expense in some way. And I think even there, I've had to grow and I feel like I've changed, which is like, I now feel in some ways more excited when I help someone else succeed. Or if I open a door for someone than I do with like with my own stuff, right? Like, and the idea of just that that's, but that's a result of having helped people

• 24:51Ryan Holiday?

  and experienced how wonderful that felt, right? Do you know what I mean? Before you do it, it feels like stupid.

• 24:57Speaker 01

  We can also paint it in a very maybe helpful, self-serving way, which is, let's put generosity aside for a second, although it is one way to describe some of these behaviors.

• 25:13Ryan Holiday?

  Yeah.

• 25:14Speaker 01

  If you, for instance, well, let me just put out an observation first, which is, I think that generosity is inversely correlated to wealth in the first world. As a percentage of what you possess, I actually believe that from what I've seen, like the more money people have, the better they are at the money accumulating game, the less they want to part with it.

• 25:41Ryan Holiday?

  Sure.

• 25:41Speaker 01

  And.

• 25:42Ryan Holiday?

  That's probably how they accumulated in the first place.

• 25:44Speaker 01

  Right.

• 25:45Ryan Holiday?

  Yeah.

• 25:45Speaker 01

  And I think, you know, look, I'm sure I'm guilty of that on some level.

• 25:49Ryan Holiday?

  Yeah.

• 25:50Speaker 01

  Right? Like, you have to value money to accumulate a bunch of it, unless you're just, okay, fine. Like, you got drunk and bought the Powerball and there you go, you have 200 million. That doesn't usually last very long.

• 26:01Ryan Holiday?

  Right.

• 26:01Speaker 01

  If that's the case. But I'll put it this way, if you, and this is something we've been talking about a little bit earlier directly, but mostly indirectly, and that is, if you go into Starbucks tomorrow and you buy, you're paying for your coffee and you give the barista 20 bucks and you're like, I'm paying for the person or two behind me.

• 26:22Ryan Holiday?

  Yeah.

• 26:23Speaker 01

  That act.

• 26:26Speaker 01

  Implicitly says, I have more than enough.

• 26:30Ryan Holiday?

  Yeah.

• 26:31Speaker 01

  That is a very uncommon perception of reality in, say, the United States.

• 26:39Ryan Holiday?

  Yeah.

• 26:40Speaker 01

  In a go, go, go.

• 26:42Ryan Holiday?

  Sure.

• 26:42Speaker 01

  Accumulate capitalist society.

• 26:44Ryan Holiday?

  Yeah.

• 26:47Speaker 01

  It is just, I think, very uncommon. Like, I have more than enough.

• 26:50Ryan Holiday?

  Yeah.

• 26:50Speaker 01

  That is what that act says.

• 26:52Ryan Holiday?

  I have extra.

• 26:52Speaker 01

  I have extra. Not only do I have what I need, I have extra, is what that says. Can you afford? Forget about 20 bucks. Can you give like five bucks? And it's like, hey, whoever comes in under five bucks.

• 27:03Ryan Holiday?

  Yeah.

• 27:04Speaker 01

  If you can afford to go to Starbucks to buy your veinti frappuccino with god knows what diabetes fuel in it, then...

• 27:10Ryan Holiday?

  Your breakfast milkshake?

• 27:11Speaker 01

  Yeah, if you're breakfast milkshake, you can probably afford to pay for someone's, like, next small black coffee. And that is a non-trivial act.

• 27:19Ryan Holiday?

  Yeah.

• 27:19Speaker 01

  As a sort of statement of self-appraisal. It sounds silly, but it's like, try it.

• 27:25Ryan Holiday?

  You're reinforcing it. Actually, the beneficiary of that is you.

• 27:28Speaker 01

  Yeah, yeah. Try it. Like, try it tomorrow.

• 27:30Ryan Holiday?

  You are not just saying that you have enough, you are acting as if you have enough. Like, as they say, act as if. You are acting as if you have enough.

• 27:40Speaker 01

  Yeah.

• 27:40Ryan Holiday?

  And then it becomes truer to you at a more, like, cellular level. And then, so when, yeah, you hear about some natural disaster, or somebody, your employee asks for your raise, or something, you can go like, I don't need to approach this from a scarcity mindset, which is the default setting. I think of the human speech. I mean, we come from a place where there was never enough food, right? Their survival was, we were always teetering on the edge of survival. And then, depending on where you come, like, more recently, you know, your grandparents grew up in the depression, or you grew up as an immigrant in a poor country, like, depending on what that is, it's even compounding the, just the biological urge of like, never enough, save some, winter is coming, right?

• 28:23Ryan Holiday?

  And you're, so you're practicing and teaching yourself, you're developing the virtue, as Aristotle says, by doing the thing.

• 28:31Speaker 01

  Yeah, and like, and practicing gripping it lightly, right? And by the way, that small act of paying for somebody behind you.

• 28:40Speaker 01

  As an easy example, like that transcends money.

• 28:45Ryan Holiday?

  Yeah.

• 28:46Speaker 01

  Right?

• 28:49Speaker 01

  Which is why I think, well, I tend to do better in crisis than I do with like the small paper cuts in life.

• 28:57Ryan Holiday?

  Yeah, yeah, me too.

• 28:59Speaker 01

  So my, like, my work to do is with the little annoyances, often, very often, human factors.

• 29:08Speaker 01

  This is where justice gets me in trouble.

• 29:11Speaker 01

  It's just the principle of the thing, you know, that's, oh, boy, now Tim's about to really punish himself.

• 29:18Speaker 01

  But the, to the extent that I've made progress on the crisis side and to the extent that I've made progress on the paper cut side, I think it's through these little things. And those things compound and they become a habit.

• 29:31Ryan Holiday?

  Well, it's important, you know.

• 29:33Speaker 01

  And it's a habit of thinking, by the way.

• 29:35Ryan Holiday?

  Yes.

• 29:35Speaker 01

  It's, the habit of action leads to a habit of thinking.

• 29:38Ryan Holiday?

  And vice versa.

• 29:40Speaker 01

  And vice versa, you can probably give me the attribution, you're so much better at this than I am, but like, it's easier to act your way into a new way of thinking than to think your way into a new way of acting. This would be an example, I think, potentially of that, they're not mutually exclusive, but that would be, that would be an example.

• 29:56Ryan Holiday?

  It's funny, right, The Obstacle is the Way, which is from this quote from Marcus Realist, he does talk a lot in meditations about how like, difficult circumstances, obstacles are fuel, whatever, but specifically that quote, I truncated, like, I shortened it, I didn't include some of the beginning and I cut out some of the middle.

• 30:14Ryan Holiday?

  But that fuller quote is about annoying obnoxious people. It's about, he says, it's about the people who obstruct us, right? And, I mean, he opens meditations with, he, he was clearly perpetually annoyed with human beings, and he would have had to interact with lots of them, probably many of the worst of them, right, as his job.

• 30:31Speaker 01

  What was, what was, what was this line that was like, when you leave the house today, expect that you will find people ungrateful, rude, entitled, these guys.

• 30:40Ryan Holiday?

  That's the opening of meditations, right? Like, that, that is, for, he, to his credit, the first book is all about gratitude, but then when he gets to the actual book.

• 30:49Speaker 01

  But I still have a few things to say.

• 30:51Ryan Holiday?

  But really, everyone else sucks. Like, these 20 people who helped me are awesome, but everyone else fucking sucks. But even the rest of that quote, you know, he goes like, we're made to work with each other. He's like, these people don't know what they're doing. He's like, he's like, uh, he's like, they can't implicate me in ugliness. And he's like, my job is to put up with them and work with that. Like, it's funny, like, the famous part is like how shitty everyone is. That's what everyone remembers. But he catches himself halfway through that paragraph, and it ends on a very positive note, to be patient and generous and collaborative, you know? So it's funny, like, we see what, we see the confirmation of like, yeah, people are that way. But what we kind of conveniently ignore is what he's saying we have to do with those people,

• 31:35Ryan Holiday?

  which is be good to them.

• 31:37Speaker 01

  I have a top secret Stoic life hack.

• 31:43Speaker 01

  Giving some wording for the thumbnail. And this is borrowed from a friend of mine. I'm not going to name him because the way that he phrased it would actually be much more offensive. But he, he's been, I've observed a, a visible difference in his state of ease in the world. And I was like, what's going on? He's like, oh, basically, I've just decided when I go out in the world, that I'm going to treat everyone as if they have a debilitating disease that affects their like mental and emotional regulation.

• 32:15Ryan Holiday?

  Yeah.

• 32:15Speaker 01

  And it just makes it so much easier to deal with everybody. It's like, you're not going to get angry at somebody if they're handicapped.

• 32:20Ryan Holiday?

  Yeah, right.

• 32:20Speaker 01

  Like, how insensitive would that be?

• 32:22Ryan Holiday?

  Yeah.

• 32:22Speaker 01

  So when you go out, it's just, there you go, folks.

• 32:25Ryan Holiday?

  The philosophical way I've heard that expressed is act as if no one else has free will and only you do, which is, which is like, they are, they are, they are programmed. There's some person pulling puppet strings, making them do all the things that are bothering you, frustrating, so they're utterly blameless and can't be held responsible for their decisions and actions, except for you. You, you do own what you do. And, and there is something about that, that, that I think, I think there's a, there's an element of truth to that. Or it's like, um, You know, act, act as if Adam Smith said, you know, again, we think of Adam Smith as this like ruthless practitioner or philosopher of capitalism, but he also writes a book called

• 33:10Ryan Holiday?

  A Theory of Moral Sentiments about like how we should be good people. But he basically says like, act as if there's an impartial observer following you everywhere, just going, hmm, you know, like to everything that you do.

• 33:23Speaker 01

  Like a little hall monitor with a clipboard.

• 33:25Ryan Holiday?

  Exactly. Just like, could you justify it to that person, you know, and a lot of times, like, they're not God or anything. He's just saying like, they're just watching. Like, how, how much would you do, how much differently would you act if other people were watching? And, and it does kind of, I think, keep you honest. You would, you'd tip a little more, you'd, you'd be a little bit more patient, you know, you'd do all the things that you want to do, but you think you can get away with not doing.

• 33:50Speaker 01

  Here's another lead domino, let's call it, just to get fancy, that if tipped over, tips over a lot of other things. And I will likely be doing this in the next year, probably in the next quarter. And it's so straightforward. And I haven't tracked the author, so I don't know if they've been embroiled in scandal or something. There's, there's no reason for me to expect that, but like, just in case, because I don't want.

• 34:12Ryan Holiday?

  Yeah. I mean, you talked about Scott Adams earlier. People just like, not be awful, so I can use your work, which I like.

• 34:19Speaker 01

  Yeah, just, just for, for the snapshot in time. But I think it was Will Bowen, might be the pronunciation, B O W N. In any case, it's the 30 day no complaint experiment.

• 34:30Ryan Holiday?

  Yes. I think this is the first blog post you ever.

• 34:33Speaker 01

  It was a very early blog post. And if you want to change your life, you put a bracelet on, it could be a rubber band, and every time you complain, you switch it to the wrist. It's maybe 21 days, but it's three or four weeks. And if you make a concerted effort to not complain at all, for, and you achieve a solid, let's call it even two weeks, without switching that bracelet, your quality of life will change completely. If, if you have some improvement, let's just say, that can be gained, which I would say is true for most people. And it, it's a forcing function for a lot of the stock practices.

• 35:12Ryan Holiday?

  It should be a rubber band, and then instead of switching, you just have that.

• 35:16Speaker 01

  I wonder, yeah, you know, I suppose you could do it a whole bunch of ways. You could get like an Opus Day, Cat of Nine Tails. Might be a little awkward in said Starbucks if suddenly bitch.

• 35:27Ryan Holiday?

  Samantha and I found that so like, obviously we work together and so, but we're not always together. So we would like get home in the afternoon or the evening and we'd be like talking about like work stuff. Right. And we realized like our kids thought we were fighting because like we weren't mad at each other, but we were both complaining slash venting about stuff, right? And if you're a kid, you don't really understand what's happening. You're like, why is dad talking negatively to mom? And why is mom talking negatively to dad? None of the animus or the frustration was directed at each other.

• 35:58Speaker 01

  Yeah.

• 35:58Ryan Holiday?

  But it's the person we were communicating it to. And so it was like, we realized, one, we just shouldn't. Well, like first off is like, okay, let's not talk about work around the kids. If that's how we're going to do it. And then second, it was like, this shouldn't be the, everything's going great. You know what I mean? Like at the end of the day, we're actually quite happy with everything. But we're just like picking the end, we're picking to end the day by like ruminating on and complaining about all the things we don't like. Right. We're not setting this angle, this happened well, and this happened well. And what about this? We're, we're just using our limited time together to fucking hurl garbage at each other.

• 36:38Speaker 01

  Kovach.

• 36:38Ryan Holiday?

  Yeah.

• 36:39Speaker 01

  Which is a very, it's a very human thing.

• 36:40Ryan Holiday?

  Of course.

• 36:40Speaker 01

  It's a super human thing. And I'll give just one tip. If people pursue this exercise, read the blog post because I thought about it much more completely. When I wrote that, the no complaint experiment, my name, it'll pop right up. And the book is great. I really, really found the book incredibly helpful.

• 36:59Speaker 01

  What is a complaint? It becomes important to define this before you embark on this experiment. You need to have some, some rules of play. And I would say one of the critical.

• 37:14Speaker 01

  One of the critical details that I at least implemented in my life, because there are going to be times when you have to discuss something that is negative, that sucks, that is just bad, that is a problem. But how do you prevent that from being categorized as a complaint? You talk about what you're going to do about it.

• 37:35Ryan Holiday?

  I'm not complaining, but.

• 37:36Speaker 01

  Yeah, that doesn't work. That's, that's, that's yellow card, switcher band. You talk about what you're going to do about it.

• 37:46Ryan Holiday?

  Yeah, right.

• 37:47Speaker 01

  Right? And you talk about like next actions, who's going to own it? How are you going to prevent it in the future? If you don't, if you don't have that addendum, it is complaint. Do not pass go, restart.

• 37:56Ryan Holiday?

  Well, I'm glad you said that because like sometimes I'll talk about like, you know, the Stoics were, were tried to be dispassionate. They tried not to complain, you know, they tried not to lament. They tried not to be angry and people go, why didn't you tell that to the civil rights movement or something? You know, like, like the, there's, they weren't, Martin Luther King wasn't complaining, right? Like protesting an injustice and then activating a large group of people for a redress of those grievances.

• 38:23Speaker 01

  It's not passive.

• 38:24Ryan Holiday?

  Is, is, that's not a complaint, right? He wasn't like tweeting like this sucks, it's not fair, right? Like he, it was so much more profound than that. So there's a difference between objecting to something or trying to change something and then complaining about it. And that's really, the Stoics are, are, and the complaint challenge, it's really about the reveling in your impotence is the problem. You know what I'm saying?

• 38:51Speaker 01

  That's the title of my next book. A middle aged man's guide to life.

• 38:56Ryan Holiday?

  Yeah. Like, and it's important that we see the Stoics as people who led social movements, people who ran for office, people who.

• 39:08Speaker 01

  You know, you have little like acronyms for books because the title's long. So you, this one could be R I P. All right, Y P, but you could shorten it. Get fancy with some old timey capitalization. Make it a little pseudo German. Anyway.

• 39:22Ryan Holiday?

  But you know what I mean? Like, there's a difference between doing something about a problem and just lamenting.

• 39:29Speaker 01

  Right. And this, so this no complaint experiment with the qualifier that I just mentioned.

• 39:35Ryan Holiday?

  Yes.

• 39:35Speaker 01

  Will force you to think very carefully about what, about what is in your control and what is not. Because if it's out of your control and you start to talk about it and it's negative, guess what? You're fucked. Now you have to switch your band and start over.

• 39:46Ryan Holiday?

  Yes.

• 39:47Speaker 01

  So it's, it's a, it is very much a forcing function. The other, the other pro tip I'll give, if you're gonna try this, delete Twitter from your phone.

• 39:56Ryan Holiday?

  I would just, whatever you're doing right now, just delete Twitter from your phone. Like, you just said, quality of life improver right there. It doesn't matter what, what your resolution is for the year. Just start by doing that because it's not improving your life in any way. And by the way, it wasn't improving your life like a year ago. And now it's like a thousand times worse and more toxic. So it's just not good for you as a person.

• 40:25Speaker 01

  Yeah. If you, yeah, if you want to control your outputs, control your inputs.

• 40:28Ryan Holiday?

  Totally.

• 40:30Speaker 01

  Be very careful about what you put into your mind.

• 40:34Ryan Holiday?

  And if you want to see what it can do to you, just see what it's cost to the richest man in the world. Like, it's not good for your soul. It's not good for your reputation. It's not good for your mind. I, I would say too, like on the complaining thing, one of the, one of the things I try to work on is like, like if you run a company or business, it's not quite complaining, but it's close to. Like, you kind of have to have a policy or you have to communicate inside your culture. Like, don't come to me with problems. Right? Because that's also a form of complaint. Like, this is wrong. It's like, okay, but you should have sat with it for five more minutes and come to me with what we're going to do about it. Because otherwise. Like, imagine, imagine, especially a big company. Like, imagine someone has a thousand employees. The thousand employees come to one person with their problem.

• 41:18Ryan Holiday?

  That person is just gonna kill themselves.

• 41:20Speaker 01

  Yeah, or if they come to multiple people, it just becomes this game of problem hot potato.

• 41:24Ryan Holiday?

  Yes.

• 41:24Speaker 01

  And that's a huge waste of everyone's resources.

• 41:27Ryan Holiday?

  Yeah. What are you gonna do about the problem? What, what is the problem presenting us as far as options? And they might all be bad options, but you can't, it, it can't just be like, here's negative information, do with it what you will.

• 41:40Speaker 01

  Yeah, I have a Google document that is like, the commandments of sort of TFE, which I like, Tim Ferriss Enterprises, right? Which is not the real name of my company, but it's just easy shorthand. And one of them is, at the very top, is, if there is a problem, come to, and it needs to be discussed, you need to have, you need to have at least two options that are ranked order.

• 42:06Ryan Holiday?

  Yeah.

• 42:06Speaker 01

  And you can explain why you've chosen your top option.

• 42:11Ryan Holiday?

  What are the other commandments? Or what are some of them?

• 42:15Speaker 01

  Some of them relate to tactical, basic procedural things, like calendaring, right? So, this is gonna be-

• 42:24Ryan Holiday?

  Put it in, like, it doesn't exist if it's not in the calendar?

• 42:28Speaker 01

  Yes, but it's more specific. So, for instance, this is gonna be very in the weeds, but people might find it helpful. So, if someone, or if I, offer, say, make this up, reviewing annual blood work with a doctor's office, and you send them two times for a potential call.

• 42:48Ryan Holiday?

  Yeah.

• 42:48Speaker 01

  They might take a few days to get back to you.

• 42:50Ryan Holiday?

  Yeah, yeah.

• 42:51Speaker 01

  But if you live in a world where a lot is, a lot is scheduled constantly, you need to block out those potential times.

• 42:57Ryan Holiday?

  Yes.

• 42:58Speaker 01

  And in the entry, in, say, Google Calendar, I would have people put a question mark at the beginning of the entry.

• 43:04Ryan Holiday?

  Yeah.

• 43:04Speaker 01

  That just means it hasn't been confirmed. It's blocked, but it hasn't been confirmed. And if there is not a very-

• 43:14Speaker 01

  Unbend, if there's not an immutable policy for doing that, things are going to get double booked, things are going to get lost, and it's going to get very messy. And then you just create a lot of work. You create more work for more people.

• 43:26Ryan Holiday?

  Yeah.

• 43:26Speaker 01

  So there would be, say, a commandment of that. There's actually a separate Google Doc, which is just calendar rules.

• 43:31Ryan Holiday?

  Yeah, like tactical, this is how I like.

• 43:33Speaker 01

  Calendar rules.

• 43:35Ryan Holiday?

  But what are more, what are some general, like, philosophical commandments then?

• 43:39Speaker 01

  Let me think about this, because I know that we have like two or three pages, but it's been a long time since I've been in that document.

• 43:45Ryan Holiday?

  I have two.

• 43:46Speaker 01

  Let's hear yours, yeah. Buy me some time.

• 43:47Ryan Holiday?

  I wrote down, because I'm going to do a whole list, but my two, they seem related, but they're separate. So one, there's a sign in the kitchenette, per se, that just says, "A sense of urgency."

• 43:57Speaker 01

  Yeah, I've seen it. It was in The Four Hour Chef.

• 43:59Ryan Holiday?

  Yeah, and so like, you have to do things quickly. And related to that, my other rule is, start the clock. So like, let's say it's going to take someone else, like, at a different, like, to get back to us or process something or manufacture. It's going to take a month, right? So if we take two weeks dicking around, thinking about it, it actually takes six weeks, right? Like, part of it we control is when we start the clock. Like, when we hit the ball back into their court and it's their problem. So I am continually frustrated with and appalled by the waste of, like, okay, if we, like, we're a bunch in there, because we're doing it for Christmas, a bunch of signed books.

• 44:38Ryan Holiday?

  If we don't get the books packaged and signed by Saturday at 9:30 a.m., because the shipping deadline is 10 a.m. for the post office here, then we might as well not fucking do it until Monday at 4:00, which is the next shipping deadline, right? So we got to start, like, we're adding two days to that clock by not starting it here, right? And so I find myself repeating a lot, like, start the clock. Don't, if something, if a video editor has to work on something.

• 45:09Ryan Holiday?

  We want them to have as much time as possible. So start the clock by giving them the materials, the outline, all the things they need to start the clock. So that's one of my big things is just, and that's how I think about life, is like, I don't procrastinate, I start the clock. A book's gonna take a year, I don't spend, you know, a bunch of time wondering if I'm gonna do it, when I'm gonna do it, I start the clock.

• 45:29Speaker 01

  Well, what's your current, when do you write typically now?

• 45:32Ryan Holiday?

  The mornings, like nine, uh, like, sorry, like 8:45, depends on school drop off, but let's say 8:45, if I'm still writing by noon, that's like a long day of writing. So it's like, it's very short concentrated windows, and if you do it day in and day out, it adds up. So, but, so if you start the clock, it adds up. If you don't start the clock, it hasn't started adding up.

• 45:55Speaker 01

  So, uh, I have a, a commandment that relates to starting the clock, and it really just relates to making faster decisions.

• 46:07Speaker 01

  When you have, and which is very often the case, incomplete information, or information that might change.

• 46:12Ryan Holiday?

  Yeah.

• 46:13Speaker 01

  It's like, if, if you, if it's reversible, or if it's an acceptable cost.

• 46:18Ryan Holiday?

  Yeah.

• 46:19Speaker 01

  I.e. acceptable loss, just book multiple things, right? If you think, if you, if you think I might fly at this time and this time, but it's gonna take like a week or two.

• 46:29Ryan Holiday?

  Yeah.

• 46:30Speaker 01

  Don't try to hold that in your head.

• 46:32Ryan Holiday?

  Yeah.

• 46:32Speaker 01

  Just book both.

• 46:33Ryan Holiday?

  And then you can cancel one and pay the fee.

• 46:35Speaker 01

  Yeah, exactly. Just, just, just.

• 46:37Ryan Holiday?

  Sure.

• 46:38Speaker 01

  If it can be reversed or canceled at minimal cost, in some cases, it's at full cost, I'm willing to bear the brunt of that.

• 46:47Ryan Holiday?

  Sure. In other cases, it's free, and it was, it was a dichotomy in your head that you couldn't do both.

• 46:51Speaker 01

  Yeah.

• 46:52Ryan Holiday?

  Yeah.

• 46:52Speaker 01

  Then, then, I, I want people to move quickly, in part because working memory is so faulty.

• 47:00Ryan Holiday?

  Yeah.

• 47:00Speaker 01

  And even documentation can be very clumsy, right? With like a million Google Docs scattered all over the place, or notes, and people lose track of things. I mean, we do have basic infrastructure and tools that we rely upon, like Asana and so on, but.

• 47:15Speaker 01

  That would be another one. Effectively, setting rules for people to make faster decisions. And explaining what types of decisions would fall into that category.

• 47:26Ryan Holiday?

  Yeah.

• 47:26Speaker 01

  Is one.

• 47:27Ryan Holiday?

  I have one, it's you better have a reason. And so by that, I mean, like, like, let's say I see someone, they made an editorial decision, or they made a content decision, or they made a business decision, or whatever. And I disagree. And that's just a fact of life. Like, you can't preemptively weigh in on every decision. The whole point of life is you have to delegate decisions, right? And so people on your team make decisions. And I accept that I'm going to disagree with a lot of those decisions. Where I get upset, or where I will come to not be able to work with a person is when I go, "Okay, so you sent this out at this time, or you did it this way." And I go, "Why?" And they're like, "Oh, I don't know." Or, you know, like, "It's just how it came," or whatever, right?

• 48:09Ryan Holiday?

  And if they're, if the decision, even if it's really bad, even if it costs a lot of money, even if I totally disagree, even got a lot of people upset, if they're going, "Well, what I was thinking was..." And then they have logic behind what they did. Then we can have a conversation and be like, "Okay, I totally see that. Here's why I disagree. Here's how I want it to go forward." But what you can't do, if you're making decisions that ultimately reach lots of people, as like a media company does, is just unthinkingly do shit. Right? And so one of mine is like, "I'll respect your reason. I may disagree, and I may correct that reason, and I may override that reason going forward. But you have to have a reason for the decisions that you make." Which you'd think it would be, everyone would always have a reason for why they do things.

• 48:54Ryan Holiday?

  But welcome to life, they don't.

• 48:56Speaker 01

  Yeah, yeah, totally. There's a, there are a bunch. I mean, this is another procedural one, but it saves a lot of time, which is, with rare exception, because there are exceptions. But with rare exception, if someone requests a meeting with me.

• 49:12Ryan Holiday?

  Yeah.

• 49:13Speaker 01

  Or a call. Number one, for me, Zoom, yeah. Number one, Zoom has introduced...

• 49:21Speaker 01

  More problems than it has solved for me.

• 49:23Ryan Holiday?

  Of course.

• 49:23Speaker 01

  Like, phone calls on a cellphone are great.

• 49:26Ryan Holiday?

  Yeah, I can walk or be driving.

• 49:27Speaker 01

  Exactly. I do not need to be sitting in my uncomfortable chair staring at a screen any longer than is necessary. So, there's a hierarchy in terms of what I will and won't do, but in addition to that, if someone requests a call, the first thing is, generally, as a response will be, "Tim would love to do this, he's currently heads down on some deadlines, could you please just shoot over a couple of topics or questions to get the ball rolling via email?"

• 49:53Ryan Holiday?

  Yeah.

• 49:54Speaker 01

  And then, if that leads, after I've reviewed that, probably on a one-on-one call with said employee, if that has been raised to my attention, and there are criteria for that, then if we book a call, almost always it's going to be 30 minutes.

• 50:08Ryan Holiday?

  Yeah. What's the smallest, do you have like a maximum, or like a normal unit of time, right? Like, so, I think people are too casual with hours, right? It's like, "Hey, I'd like to meet," and they go, "Okay," and then they set it in the calendar for an hour, and you've just said it's going to take an hour.

• 50:25Speaker 01

  Yeah, I mean, if someone has requested a meeting with you, which is what I deal with more than the opposite, if you do, if you have a 30-minute block, there's a good chance they can go to 45.

• 50:34Ryan Holiday?

  Yeah.

• 50:35Speaker 01

  If need be. But block it out on 30. I prefer calls that are used for decision-making, not problem-defining.

• 50:42Ryan Holiday?

  Yes.

• 50:43Speaker 01

  So, pretty much always, an agenda, even if it's just a few bullets, will be requested because Tim likes to be as prepared as possible, something like that.

• 50:54Ryan Holiday?

  Yeah, sure.

• 50:56Speaker 01

  These seem basic, but man, do these little things add up over time.

• 51:01Ryan Holiday?

  Yeah.

• 51:01Speaker 01

  And, very small, repetitive tasks done inefficiently can cripple you as an individual contributor, especially if you are trying to block out extended periods of time to do things.

• 51:16Ryan Holiday?

  Yeah.

• 51:16Speaker 01

  So, another yellow/red flag would be, and this is not verbatim what's in the document, but let's just say... That three things come up in a given week in a similar category, like of a similar type, that need to be turned around that week.

• 51:32Ryan Holiday?

  Yeah.

• 51:32Speaker 01

  That were not predicted. A system is broken. Like, there needs to be a process fixed.

• 51:37Ryan Holiday?

  Sure.

• 51:37Speaker 01

  There that that that pattern of related fires.

• 51:43Ryan Holiday?

  Yeah.

• 51:43Speaker 01

  That that urgency.

• 51:45Ryan Holiday?

  Solve it further upstream.

• 51:47Speaker 01

  Should be solved further upstream. That then comes to, and I mean, it might seem strange. Hopefully, it doesn't seem strange, but like, a lot of the stuff in the four hour work week, I still lean extremely heavily on, and the basic framework, I would modify a little bit, although the acronym you'll see in a second is is a little less appealing. But in the in the four hour work week, you have you have DEA L, right? Oh, how clever. Deal. That works. Okay. Definition, elimination, automation, liberation. In this case, I would say it's definition, elimination, automation, delegation. Unfortunately, that spells dead. But the idea is you need to be very clear. If you're going to be trying to determine, say with 80 20 analysis, which I still use all the time, Pareto's law, to identify the few inputs that produce the disproportionately

• 52:32Speaker 01

  large outputs.

• 52:33Ryan Holiday?

  Yeah.

• 52:34Speaker 01

  You kind of need to know what targets you're aiming for.

• 52:37Ryan Holiday?

  Yeah.

• 52:37Speaker 01

  You really need to know. And that's definition. And there's a lot more to definition. Being very clear, if you're not clear on what you want, the the likelihood of the universe delivering that to your doorstep with a bow on top is very low.

• 52:47Ryan Holiday?

  Yeah.

• 52:48Speaker 01

  So, you know, I've said before, and I remind myself of this a lot, that, you know, the world rewards the specific ask and punishes the vague wish. And definition, then, is step one. Then you have elimination, which is like, what, what, what, what's golden fetters or less than golden fetters do you have that are hindering you from?

• 53:15Speaker 01

  Efficiently trying to reach those objectives.

• 53:17Ryan Holiday?

  Yeah.

• 53:18Speaker 01

  Or address those, those things that you have defined. What are the activities, right? The, if we're doing an eighty twenty analysis, right? The twenty percent that produce the eighty. Well, that means hypothetically, you have eighty percent of that pie chart left that you should trim.

• 53:32Ryan Holiday?

  Yeah.

• 53:33Speaker 01

  Okay, elimination, getting rid of as much as possible. Because a lot of people skip that step. And this, we, we're seeing it right now on steroids with ChatGPT. Like people doing a lot of meaningless bullshit very quickly.

• 53:45Ryan Holiday?

  Yeah.

• 53:45Speaker 01

  And like doing something quickly or efficiently does not make it important.

• 53:49Ryan Holiday?

  Yeah.

• 53:49Speaker 01

  So eliminating as much as possible, especially if you're going to have a very lean team, which I would suggest anyone should aim for, even if you have a thousand employees.

• 53:58Ryan Holiday?

  Yeah.

• 53:58Speaker 01

  Right? So definition, elimination, automation, this will be using technology.

• 54:02Ryan Holiday?

  How do you do it more than, so you'll do it once and you get?

• 54:07Speaker 01

  Yeah, setting a, setting a system or a policy.

• 54:09Ryan Holiday?

  Right.

• 54:09Speaker 01

  Which could be very simple, by the way. It could be having a, a, a virtual assistant or an assistant or employee or maybe yourself, where you have a recurring calendar reminder to do this thing so that it doesn't pop up in the middle of your week unexpectedly. Oh shit, property taxes are behind. Oh, wait a second, some guy showed up at the farm saying that I'm. Whatever.

• 54:30Ryan Holiday?

  Here, if you're sitting down and writing out your mortgage check each month, you fucked up. It should be automated.

• 54:35Speaker 01

  Right, like that's something that can be automated. So automation can be a, something that is implemented manually.

• 54:42Ryan Holiday?

  Yeah.

• 54:43Speaker 01

  Right? Like a, I have a reminder every morning, which is like, do these, do these three low back exercises. So I don't need to think about it.

• 54:50Ryan Holiday?

  You're automating the willpower and the, the contemplation.

• 54:54Speaker 01

  Right. So then there's the automation and automation also, by the way, I was looking at some of the tasks that I've assigned to assistants in the past. We don't need to get derailed here, but. I track a lot of the AI developments pretty closely and I do experiment with these tools and I took the language that we had put in several Asana tasks for people to manually do. And I looked at their response, then we loaded the exact, more or less like 95% identical language from that Asana task into ChatGPT to see what the output would look like. And it was like 90% there.

• 55:34Ryan Holiday?

  Wow.

• 55:35Speaker 01

  And it was instantaneous.

• 55:36Ryan Holiday?

  Yeah.

• 55:37Speaker 01

  No comms overhead.

• 55:39Ryan Holiday?

  Wow.

• 55:40Speaker 01

  And there are drawbacks.

• 55:42Ryan Holiday?

  Sure.

• 55:43Speaker 01

  I'm not, we don't have to get into them right now, but the technology is evolving so quickly, as soon as that stuff is really easily, elegantly, seamlessly integrated with OpenTable, integrated with Kayak, or directly with airlines, or the systems, underlying reservation systems with say, concierge services have access to this, they don't need to, they're not calling all the airlines individually to negotiate on your behalf. Once those integrations are there, I really feel like two of the places are going to be massively disrupted and suffer economically from AI. There will be benefits, but will be, as two examples, India and the Philippines, call centers, virtual assistants, it's going to be, it's going to be very challenging.

• 56:25Speaker 01

  But that's an example of some degree of leveraging technology.

• 56:31Ryan Holiday?

  Yeah.

• 56:32Speaker 01

  And reducing interpersonal overhead. And then at the very end, you have delegation.

• 56:36Ryan Holiday?

  Yeah.

• 56:37Speaker 01

  Right?

• 56:38Ryan Holiday?

  Yep.

• 56:39Speaker 01

  And that process is something that I try to instill also in my employees, in my team. Like, think these through in this order.

• 56:48Ryan Holiday?

  Yeah. You don't need to be doing everything, because everything needs to get done.

• 56:51Speaker 01

  Yeah.

• 56:52Ryan Holiday?

  That's your attitude towards them, and that should be their attitude towards tools, systems.

• 56:56Speaker 01

  Yeah. And if you're thinking about, if you're, if you're doing a lot of stuff, because I am not going to keep an eye on all the balls that are being juggled, if there are certain things that are being repeated, come to me with a suggestion.

• 57:08Ryan Holiday?

  Yeah.

• 57:09Speaker 01

  For a systems improvement.

• 57:10Ryan Holiday?

  I don't want your life to suck.

• 57:11Speaker 01

  Yeah. So, we've made a bunch of systems improvements in the last six months, and I think we will continue to do that. The most neglected step in all of that is elimination.

• 57:24Speaker 01

  For a lot of reasons.

• 57:25Ryan Holiday?

  Well, I would say the most neglected step.

• 57:27Speaker 01

  Actually, maybe at the top of the funnel.

• 57:29Ryan Holiday?

  Yeah, to me, and people miss it about the four hour work week and why it's such an important book and why do you think its relationship to Stoicism is so important? The subtitle of that book about lifestyle design, right? Like, what do you want your life to look like? Because maybe, I mean, maybe for some people, they do like to do that stuff. But if you don't think about Seneca's thing is like, if you don't know where you're sailing, no wind is favorable. If you don't know what you want your life to look like, then you can't do any of that stuff. Like, for me, like, like I've said this, I just hired a new assistant and I was like, "Look, my ideal day is there's nothing in this calendar." Not like, "I'm not working." If there's nothing in the calendar, then I'm working all day on things I actually like doing. I'm living my life. And, and so I now know from experience, I don't like meetings, I don't like phone calls, I don't like things that take me away from what I like doing, right?

• 58:14Ryan Holiday?

  And, and that's family and work. And so you've got to start with, like, what do you want your life to look at? What, what are you trying to design for? What are you optimizing for? And then there's all these great frameworks for being optimized, but you've got to know what's.

• 58:28Speaker 01

  And a great, a grace for, a great forcing function for systems if you're, if you don't have a lot of practice, talking about practices, right?

• 58:37Speaker 01

  If you're trying to sort of change your mode of thinking, your way of pattern recognition, your way of problem solving by acting first, consider doing mini-retirement.

• 58:47Ryan Holiday?

  Yeah.

• 58:47Speaker 01

  Like, and that's minimum three, ideally like four weeks off the grid or, which doesn't mean you have to be on like, in a canoe on the Amazon.

• 58:56Ryan Holiday?

  Just take everything away.

• 58:57Speaker 01

  Yeah, it just means you are not allowed to fight any fires.

• 59:00Ryan Holiday?

  Yes.

• 59:00Speaker 01

  If you just go on a one-week vacation or even a two-week vacation, you can let things turn into a blaze and come back and try to fix it. Three or four weeks, very difficult. Typically, that will force you to put in place policies, rules, systems, and ongoing types of delegation that will then persist past the point that you return. That's the whole intention. So that would be another recommendation for folks. If they seem to do a lot of ad hoc things, they're very busy. And they suspect maybe these things could be eliminated, maybe these things could be systematized, but they never seem to have the time to do it because they're just caught up in the day to day. And I end up there too, by the way. Then look out over the next

• 59:43Speaker 01

  six months or year, plan a mini-retirement that will force a lot of things to happen.

• 59:48Ryan Holiday?

  Yeah, we spent a month in LA this year, and so we had a pet sitter like while we were gone at the house. And then it was amazing, right? Because I mean, no one died, everything got taken care of. And we were like, oh, you could have this while you're home, too. You know what I mean? And you could just have the fun part, right? And so you gotta step away and come up with something that operates while you're away. And then you can go, okay, what part of this structure or infrastructure am I keeping? Because what's the point of the success if you're a miserable mess all the time?

• 1:00:18Speaker 01

  Right, yeah.

• 1:00:19Ryan Holiday?

  Dude, this was amazing.

• 1:00:21Speaker 01

  Yeah.

• 1:00:21Ryan Holiday?

  Thanks so much.

• 1:00:22Speaker 01

  Yeah, super fun. Thanks very much.

• 1:00:29Ryan Holiday?

  Thanks so much for listening. If you could rate this podcast and leave a review on iTunes, that would mean so much to us, and it would really help the show. We appreciate it, and I'll see you next episode.