Gary Vaynerchuk, David Rubenstein, Ali Abdaal, Emily Oster, Brad Feld, and Randall Stutman on Business and Success | It’s Time To Snap Out Of It

Ryan reads today’s daily meditation and looks back at some of the best interviews on business from 2021. Featuring entrepreneur Gary Vaynerchuk on the best way to maintain long term business success, billionaire David Rubenstein on learning from past historical figures’ successes and from their mistakes, Ali Abdaal on staying productive and getting your life organized, economist Emily Oster on how to communicate positive messaging and weigh out risk vs rationality, venture capitalist Brad Feld on why entrepreneurs have to focus attention inward toward self-improvement, and Randall Stutman on making people better. → We hope you join us in the 2022 New Year New You Challenge. It’s 3 weeks of actionable challenges, presented in an email per day, built around the best, most timeless wisdom in Stoic philosophy. Just go to https://dailystoic.com/challenge to sign up before sign ups end on January 1st! GiveWell is the best site for figuring out how and where to donate your money to have the greatest impact. If you’ve never donated to GiveWell’s recommended charities before, you can have your donation matched up to $250 before the end of the year or as long as matching funds last. Just go to GiveWell.org and pick podcast and enter DAILY STOIC at checkout. Trade Coffee will match you to coffees you’ll love from 400+ craft coffees, and will send you a freshly roasted bag as often as you’d like. Trade is offering your first bag free and $5 off your bundle at checkout. And, this holiday season, give the coffee lover in your life the gift of better coffee too, with their own personalized gift coffee subscription from Trade. To get yours, go to drinktrade.com/DAILYSTOIC and use promo code DAILYSTOIC. Take the quiz to start your journey to the perfect cup. LMNT is the maker of electrolyte drink mixes that help you stay active at home, work, the gym, or anywhere else. Electrolytes are a key part of a happy, healthy body. As a listener of this show, you can receive a free LMNT Sample Pack for only $5 for shipping. To claim this exclusive deal you must go to drinkLMNT.com/dailystoic. If you don’t love it, they will refund your $5 no questions asked. Sign up for the Daily Stoic email: https://DailyStoic.com/dailyemailCheck 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.

• 0:03Ryan 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.

• 0:44Ryan Holiday?

  It's time to snap out of it. Look, guys, there's just nine more days to sign up for the Daily Stoic New Year, New You Challenge. And if you need a last-minute gift for a friend or family member, you want to do it as part of a team or a group together, you can gift the New Year, New You Challenge as well. But let's get into it. Over the last 21 months, you've asked these questions. What day is it? Was that this morning or yesterday afternoon that I showered? It's already December? What even is time? And this collective disorientation dates back at least as early as April 2020, when Kate McKinnon opened the first SNL at

• 1:26Ryan Holiday?

  home with "Live from Zoom" at some time between March and August. And Tom Hanks put it in a way that remains relatable. He said, "There's no such thing as Saturdays anymore. It's just every day is today." And on the one hand, this is funny, and it's funny that searches for "What day is it?" continue to spike, and it's funny that weekends feel like weekdays, and weekdays feel like weekends. But on the other hand, it's alarming. It's alarming the rate at which 2021 flew by. All the things we said we were going to do, the goals we were going to accomplish, the books we were going to read, the projects we were going to complete, the boxes we were going to check off, we didn't get to many of them. Or any of them.

• 2:10Ryan Holiday?

  And that should alarm us. "Every day more of our life is used up and less and less of it is left," Marcus Aurelius wrote. And so quoting Heracles, he said, "Our words and actions should not be like those of sleepers." But that's what so many of us have started to do. We've begun to sleepwalk through life as life is walking, nay, running away from us. Well, it's time to wake up. We must be deliberate. We must snap out of this endless trance. How? Well, we created the 2022 New Year, New You Challenge with an eye towards that. We chose challenges that the Stoics themselves would do when they found themselves, as

• 2:53Ryan Holiday?

  Musonius Rufus put it, "following wretched habit." Seneca wrote about the powers of a cold plunge. Marcus wrote about waking up earlier than his body preferred. Epictetus told his students to seek out a challenge, the way a boxer seeks out a stronger sparring partner when they need to shake things up. Cato, we know, would step outside himself and take a walk around Rome to help others. And as Plutarch said, "He made it his business to salute and address, without help from others, those he met on his rounds." So we built this New Year, New You Challenge around time-tested practices and exercises because we've experienced it too. We've been saying, I've been saying, whoa, where did the year go? We didn't all get to the projects we wanted to get to.

• 3:38Ryan Holiday?

  And so we made this challenge as much for us as for you. We made it so by this time next year, you might be saying, whoa, what a year, instead of, whoa, where did the time go? That's not only what you want, it's what you deserve. So I hope you join me because I do these challenges alongside you. In fact, I design them myself in part in mind. I hope you join me and the 2022 New Year, New You Challenge kicks off in a little over a week, and it's three weeks of actionable challenges presented in one email per day, built around the best, most timeless wisdom and Stoic philosophy. Three weeks that will hopefully reorient your relationship with time and space. As much as is possible in the middle of a pandemic,

• 4:21Ryan Holiday?

  it should help you snap out of this trance we've all found ourselves in and help make 2022 your best year yet, no matter what's happening in the world around you. Go to dailystoic.com/challenge to join us. I'd love to have you. I'm challenging you to join me. I can't wait to see you. Dailystoic.com/challenge.

• 4:43Ryan Holiday?

  Hey, it's Ryan Holiday. Welcome to the Daily Stoic Podcast.

• 4:51Ryan Holiday?

  Stoicism was founded by an entrepreneur, not entrepreneurially founded, but it was founded by Zeno. He's a merchant. He deals in Tyrian purple, suffers a shipwreck, crashes, loses everything, ends up in Athens penniless, and turns to philosophy in a bookstore. As it happens, I named my bookstore The Painted Porch, after the fact that not only was Stoicism founded in a bookstore, right? This is where Zeno is introduced to the works of Socrates, finds his philosophical mentor. But then where does Zeno go to set up his school of philosophy?

• 5:32Ryan Holiday?

  In the Agora at the Stoa, the Stoa Pochyle, the painted porch, right in the center of town, where the idea of philosophy or any innovation being part of the battle of ideas, or the marketplace of ideas, here Stoicism is battling for attention amidst all the other ideas, all the other distractions and temptations of the Agora. And I think that's why historically Stoicism has resonated with not just athletes and military leaders and politicians, but also merchants and business people. And that's been one of the most interesting parts of the Daily Stoic Podcast,

• 6:13Ryan Holiday?

  talking to people who were and are really successful at what they do in the business world. What lessons can Stoicism teach us in whatever pursuit, whatever career, whatever field we're happening? We happen to be in. And in today's episode, we have a bunch of interesting business leaders. And I'll bring that to you now. First, we're going to be talking with Gary Vaynerchuk, who I interviewed in person at The Painted Porch. It was an awesome interview. We had a great time. Gary and I talk about Stoicism, soft skills, becoming your best self. His new book, Twelve and a Half, is great. And we've got signed copies of some of his other books at The Painted Porch and at the

• 6:57Ryan Holiday?

  paintedporch.com. You can follow Gary on pretty much every platform, @GaryV. Great guy. Maybe not what you would associate with Stoicism, but I think there's a lot we can learn from him. Then I talked with David Rubenstein on Patriotic Philanthropy, The Value of History. I love a business person who understands the context in which they are operating under, understands more than just dollars and cents. And David Rubenstein is a fantastic example of that. Founder of the Carlyle Group, one of the richest people in America, and yet seems to be very focused on how to give back, what our obligations are, and how we can learn from history. I talked to Ali Abdaal, the YouTuber. If you don't follow him on YouTube, he's got a whole

• 7:38Ryan Holiday?

  bunch of great and awesome content on productivity. And that's what we talk about. Ali and I talk about the keys to productivity and redefining success. Talk really about what the Stoic definition of success actually looks like, how to stay productive and get your life organized. Early in the pandemic, I talked to the economist Emily Oster on rationality and risk. I think this is one of my best conversations. I love her work. I love her Substack. If you don't subscribe to that, you should. And we talked about how to communicate positive messaging, how to weigh out risk, how to be rational in midst of craziness. And I also talked to the venture capitalist Brad Feld on his book, The Weekly Nietzsche, What Nietzsche Can Teach Us, both pro and con, his connection to the Stoics, and of

• 8:23Ryan Holiday?

  course, the power of daily practice. And then finally, I talked to the guy behind the guy, one of the best business coaches in the world. Seriously, he is. Been a business coach for Fortune 500 CEOs, Fortune 100 CEOs, hedge fund managers, billionaires, some of the best and biggest names in business. He's also a mentor of mine. I've really enjoyed getting to know him and I talked to him also as part of the Daily Stoic Leadership Challenge. This is one of our best interviews of the year. So here I am talking with Randall about how to make people better, which is our job as leaders. And if you haven't checked out the Daily Stoic Leadership Challenge, I'd love to have you do that. Sign up at

• 9:07Ryan Holiday?

  dailystoic.com/leadershipchallenge.

• 9:12Ryan Holiday?

  I'm in this writers group, like James Clear, Mark Manson. We get together once a year. We sit around and everyone gets to talk. We all take turns. We get to talk about the person as if they're not in the room and they can't say anything. All they can do is take notes. And it's super powerful because you get to see how people you actually care about, not just random people on the internet or whatever.

• 9:33Speaker 01

  And is candor, and do you feel like everyone's caught good candor?

• 9:37Ryan Holiday?

  Yeah, yeah. And but because they are in the room, you're still going to be kind, right?

• 9:41Speaker 01

  And you can't go all the way there.

• 9:43Ryan Holiday?

  Right. But you can, you can plant the seed of what they can take back and go, you know what? They're right. I am doing too much of this, or not enough of this, or why am I being held back here? And then you take that back and you work on it. It's ironic because we're talking about self-awareness, but one of the best ways to get it is from other people. I would say a spouse being the primary way because they know you better than anyone and they can also speak to you the most directly.

• 10:09Speaker 01

  I think that it is just a big goddamn deal and all of this is, and it's really time that we actually talk about it as, like, the alternate title to this is, the soft skills are hard.

• 10:23Ryan Holiday?

  Ooh, that'd be a good title.

• 10:24Speaker 01

  Thank you. You know, and so that to me is what, right? Because it's a double, right? Oh, fuck. Anyway, I, I'm just ready for this because I know it to be true. I know it to be true. Of course, you can build an empire by not being nice.

• 10:43Ryan Holiday?

  A lot of them are that way.

• 10:44Speaker 01

  Of course. But if you're on the other side of reading it, wouldn't it be nice to enjoy it? Like, have you met the 70-year-old Titans that did it the other way?

• 10:54Ryan Holiday?

  Nobody suffers more than that person.

• 10:56Speaker 01

  That person's fucking life blows. Like, I love that you put these people on a pedestal. They're not happy. They're not as happy as you think. Like, For real.

• 11:04Ryan Holiday?

  Yeah. No, no, it's uh, you would, if you actually knew what it was like in their head, you would not trade places with them for all the money in the world.

• 11:14Speaker 01

  It's why I always get crazy about that. I'd rather cry in my Ferrari than, but like, how about not crying?

• 11:20Ryan Holiday?

  Yeah.

• 11:21Speaker 01

  How about smiling in your fucking whatever?

• 11:23Ryan Holiday?

  Yeah.

• 11:24Speaker 01

  Ford.

• 11:24Ryan Holiday?

  Or you're jealous of this person who's traveling on a private jet to some exotic, what if you had a life that you didn't need to run away from?

• 11:31Speaker 01

  Right. Like, like, what are we talking about? Like, yeah.

• 11:36Ryan Holiday?

  All right, a couple more quick riffs. Mark Sereless says, uh, strict with yourself, tolerant with others. How do you like that?

• 11:45Speaker 01

  A lot.

• 11:46Ryan Holiday?

  Yeah?

• 11:46Speaker 01

  Yes. I would actually argue that that's where I need to find a little bit of balance. My strictness with me is such a healthy one, and my tolerance with others may be too extreme. Back to lack of candor, I'm trying to get a little better. Coddling? Entitlement. Um, but my strictness with me is really cool. Uh, it's not like I eat at five or wake up at, it's, it's this ability to not compromise on a couple of things. And the biggest one is kindness.

• 12:17Ryan Holiday?

  Yeah, or it's like, if you're driven and ambitious, you work 15 hours a day, it can be really easy to just expect that from other people. One of my favorite videos, you're talking to someone, they're like, you're like, the other people, they're not owners of the business. You can't expect what you expect of yourself of them.

• 12:33Speaker 01

  It's absurd. I, I once said to somebody, I'm like, you're talking as if we're talking about slavery.

• 12:38Ryan Holiday?

  Yeah.

• 12:39Speaker 01

  Like, what the fuck are you talking about? Um, yeah, my, I have zero expectations of others. If I'm being really honest, I take it.

• 12:47Ryan Holiday?

  That way you're always pleasantly surprised.

• 12:49Speaker 01

  Yeah. Like, and I'm accountable. It's like, look, I mean, yeah, I, I love that, and I'm a believer of it.

• 12:56Ryan Holiday?

  Yeah. And look, it's called self-discipline. Right? Not, not, you know, nothing else.

• 13:03Speaker 01

  I think a lot about why people point fingers, why people have fallen in love with judgment of others. And I've come to realize it's because they're practicing on themselves. You know, my inability to overjudge myself is exactly why I don't judge others.

• 13:21Speaker 01

  We're, we're holding ourselves up to, we're the judge and jury and we're putting ourselves into jails.

• 13:28Ryan Holiday?

  Right.

• 13:29Speaker 01

  Right? Like it's nice to have aspir- I mean, I'm ambitious as fuck.

• 13:32Ryan Holiday?

  Sure.

• 13:32Speaker 01

  It's nice to have standards. I'm not saying that, but like this notion of beating yourself up when you fall short on something that is a standard or an ambition is incredibly unhealthy.

• 13:44Ryan Holiday?

  Well, it's like you would never talk to someone else the way that you talk to yourself.

• 13:48Speaker 01

  But what's funny is mine is actually slightly twisted on that. I talk to everybody the way I talk to myself, which is why I talk so nicely to everybody.

• 13:55Ryan Holiday?

  But that's how you want it, right? But most, a lot of people talk to themselves in a way that they would never tolerate.

• 14:02Speaker 01

  Correct, because most people try to prop themselves up by tearing everybody else down.

• 14:06Ryan Holiday?

  Right. Alright, so Marx realized again, uh, the best revenge, the best way to get even is to not be like them.

• 14:15Speaker 01

  My, I think there's something that I like that. Uh, my version on revenge is a little bit more like the inability to even care about their action.

• 14:27Ryan Holiday?

  To shrug it off?

• 14:28Speaker 01

  In, in a more audacious way.

• 14:32Ryan Holiday?

  Okay.

• 14:32Speaker 01

  Not only shrug it off, recognize that you're about to actually stick it to them by not even acknowledging it happened. It's, it's an extreme version of cutting them out of your ecosystem.

• 14:46Ryan Holiday?

  Sure.

• 14:49Speaker 01

  That's how I've dealt with like people that have done really not nice things or trying to go like, it's almost as if it didn't happen.

• 14:56Ryan Holiday?

  Yes.

• 14:56Speaker 01

  It like goes on this nice little shelf. I'm like, that's nice. You can play with yourself in that cocoon of like, whatever you feel about me. You've now become a energy that is just like, not a good use of time. And even giving it time, and to be frank, I've evolved a little bit from that. I'm now- Receiving that energy and kind of deploying really deep sympathy. The thought at this point in my life that you want to spend any of your time hurting somebody else's feelings seems outrageously foreign and really just makes me feel compassionate.

• 15:35Ryan Holiday?

  The ultimate person who suffers from it is them.

• 15:38Speaker 01

  A hundred, all that we're doing out here is, somebody said something to me yesterday, I did something kind of cool, giving away some stuff, and they were like, kind of asking, I was like, late, I was getting home, I was just replying like, it's just because I have so much love to give, I don't know what to do with it all.

• 15:55Ryan Holiday?

  That's sweet.

• 15:56Speaker 01

  And I really think that that's, that a lot of people live the reverse. They have so much pain, they're trying to get it out. You know, for me, it's an abundance of love, of like, fuck it, like, I don't want it, like, what am I, like, this is, like, I better do stuff.

• 16:08Ryan Holiday?

  Right.

• 16:09Speaker 01

  I think that's how hate works.

• 16:11Ryan Holiday?

  All right, so I think anyone who talks about stuff publicly, let alone puts out a book like this, and then mine, I think the tricky part is, it's easy to talk about, it's hard to do.

• 16:22Speaker 01

  Yes.

• 16:23Ryan Holiday?

  Right? Epictetus says, "Don't talk about your philosophy, embody it."

• 16:26Speaker 01

  Yes.

• 16:27Ryan Holiday?

  Or, "Don't talk about it, be about it." Sometimes I wonder, like, if I'd never written about it, but I believed it, could I get convicted of these things in court? Right? Like, if somebody didn't know who I was, they just bumped into me on the street, how close am I actually to the things I write and talk about? How's that journey for you?

• 16:45Speaker 01

  Uncomfortably remarkable.

• 16:48Ryan Holiday?

  Okay.

• 16:49Speaker 01

  I would say that I understate me. I understate the things I live.

• 16:59Ryan Holiday?

  Okay.

• 17:00Speaker 01

  I really believe that.

• 17:01Ryan Holiday?

  How do you get there?

• 17:03Speaker 01

  Well, I get there by doing it.

• 17:06Ryan Holiday?

  Sure.

• 17:07Speaker 01

  I'm doing it.

• 17:08Ryan Holiday?

  Yeah.

• 17:09Speaker 01

  And I get there by understating it. Like, I, I, look, I have Andy and D-Rock here behind the cameras, you know, I'm, they'll probably agree with me, I'm starting to actually, this book and a lot of others, like, the last two years, I would say that I'm starting to peel away my curtain a little bit more and show this stuff more, because it's hard to talk about this stuff. It's like, hey, I'm humble.

• 17:34Ryan Holiday?

  Yeah.

• 17:35Speaker 01

  The fuck is that content?

• 17:36Ryan Holiday?

  Sure.

• 17:37Speaker 01

  So you got to find your balance, because that's not nice. But to answer your question, the thing that I've always loved is...

• 17:46Speaker 01

  I'm more about the things I talk about and I talk about them at scale.

• 17:52Ryan Holiday?

  But earlier you were saying kind candor that you were a 10 before, now you're a 60. So you're still at a D, right? So you're still, you're still moving up.

• 17:59Speaker 01

  Yeah, but this book's also not called 13.

• 18:01Ryan Holiday?

  No, that's a good point. So you feel like.

• 18:03Speaker 01

  Like the book, like the book is like, I stink at this.

• 18:05Ryan Holiday?

  Yeah.

• 18:06Speaker 01

  Yeah, like I don't want, listen, uh, he worked for somebody that used to work for me. I don't want him to know one story from Sam that undermines Gary Vee. I have never wanted, I live very loose. I have admins that have access to everything. My team has, these guys have access to everything. I have no interest in letting any other human being ever have leverage on me. The thought of saying one thing and doing another to then worry if I can control them to never say it is fucking asinine.

• 18:38Ryan Holiday?

  Sure, but I don't know kindness, it's easy to say and then someone does something cruel. Right? Like we have these instantaneous reactions to things. You find, you have to check yourself.

• 18:48Speaker 01

  You know, we got to this a little bit in this talk and it's, I'm starting to like, this is starting to come top of mind for me. I would, do you know how many words I could have put in this book? This didn't have to be these 13 traits.

• 18:59Ryan Holiday?

  Sure, sure.

• 18:59Speaker 01

  There's a lot of other shit. These are the ones that I live, like this is like, you know, this is the ones I live and the ones that I notice and I can see them and yeah, I mean, I'm, I don't feel vulnerable.

• 19:11Ryan Holiday?

  It's good. No, no, no, that's great.

• 19:13Speaker 01

  I think I probably somewhere in hindsight realized 15 years ago, oh, I'm going for it. Right? And when I realized that I probably, you know what I had a good read on? That the internet was going to expose everything, like a very good read. Like I talked about it back then, like in Wine Library TV, like I would reference it. And I think by knowing that and by knowing I was going to go for it, I must have become a much better version of myself on all these things. Because I was like, I don't want the vulnerability.

• 19:44Ryan Holiday?

  But it's something you're, you, you worked on and are working on. These are the ideals and you're aspiring to get there day to day, right? It's not just.

• 19:51Speaker 01

  Yes, but I'd be not authentic if I didn't say that for the 12 of them, they come uncomfortably easy to me, always have and are foundational and why I think have outsized results. I'm really proud of myself because I don't think I could have made, this book would have been called 12 seven years ago.

• 20:09Ryan Holiday?

  You wouldn't have admitted the half.

• 20:11Speaker 01

  I grew up in a family where complaining. Was the single worst thing anyone could do.

• 20:17Ryan Holiday?

  Sure.

• 20:17Speaker 01

  Because we came from the old country and mom and dad had to go outside for a toilet and didn't have bread. So the fuck are you upset that your Nintendo is not working? So we demonized complaining in my family. Somehow I feel like that bled into not being or talking about vulnerabilities.

• 20:33Ryan Holiday?

  Sure.

• 20:33Speaker 01

  And so I don't think seven years ago I could have talked about the vulnerability of candor the way I did here. And I, to your point, I aspire to be more vulnerable over the next 40 years, which I think will push me into new places.

• 20:51Ryan Holiday?

  Here's me talking to David Rubenstein. Yeah, it's, uh, there's that Roosevelt line about how comparison is the thief of joy. Some of the, you know, extremely wealthy people I've met, as you said, objectively, you'd be like, oh, this person has a lot of money and you don't realize that they're, they're of course comparing themselves to the person three spaces above them on the Forbes list.

• 21:16Speaker 02

  Well, look, um, many of the most tortured souls I know are the wealthiest people I know.

• 21:22Ryan Holiday?

  Why is that?

• 21:23Speaker 02

  Well, because you, if you make five billion, you feel I should make 10 billion. If you make 10 billion, you say, how are people telling me, why shouldn't I win the Nobel Peace Prize? I, I want to do something more than just be known as a rich guy. So everybody wants something different, it seems. Nobody's ever happy with what they have. I'm pretty happy with where I am, but of course I'd like to do more with my life. I wish I had accomplished more, but you know, there are some people who feel that unless they are recognized for every, by everybody is, has been universally brilliant and talented and, and deserving all kinds of awards, their, their life isn't going to be pleasurable.

• 21:56Ryan Holiday?

  Do you think part of it is that also sort of tortured people who have some kind of thing they need fulfilled, it's also what draws them to like, let's say, make a lot of money or try to be the best quarterback in the world or the most famous singer in the world?

• 22:13Speaker 02

  Yeah, to be successful in anything, as I was saying in my leadership book, you've really got to put in the time, you got to work hard, you have to drop other things. And that can make you a person that's so unidimensional that, you know, you're not attractive to a lot of other people. They don't want to deal with you. And so after you make all the success, people say, well, I don't really care that you're that successful. I don't really like you. You're not a very likeable person. I know some very wealthy people that nobody likes. People don't like certain wealthy people. There are some wealthy people that people really admire, but some wealthy people have made it in ways that people don't want to do anything with them, unless they just take their money as a philanthropic gift, but otherwise they don't want to socialize with them or see them at all.

• 22:51Ryan Holiday?

  Well, and if you were an easily satisfied person who was happy with, you know, little, you probably wouldn't have like, if Michael Jordan was just happy with being pretty good, he wouldn't have been Michael Jordan, and thus that also makes it hard to enjoy being Michael Jordan.

• 23:09Speaker 02

  I agree. I mean, Michael Jordan, I don't know him, but I assume he's probably not as happy as when everybody was waking up every day looking at his box scores. He's not as big a deal as he once was, though he's still a big deal. But, you know, when you're not in the newspapers every day for what you're doing, and you thrive off that, you may feel that you're not as big as you once were, and therefore you're not as happy as you once were.

• 23:31Ryan Holiday?

  There's a, there's a story I've told a couple of times. You're probably familiar with it, but Joseph Heller and Kurt Vonnegut are at a party of a billionaire, and Vonnegut's teasing Heller, and he says, you know, this, this guy made more money this week than your books will make in their lifetime. And, and Heller says, yeah, but I have something he'll never have. I have enough. Do you, do you find, you meet sort of people that just, nothing is ever enough? Like, no amount of success, no amount of fame, no amount of money will ever make them feel content?

• 24:05Speaker 02

  Well, what's the title of Mary Trump's book?

• 24:08Ryan Holiday?

  Yeah, you're right, you're right.

• 24:10Speaker 02

  So, yes, there are certain people that are never going to get enough attention and praise that they are going to be satisfied. And there's no doubt that psychiatrists are very busy dealing with those people all the time. Yes, it's a challenge, because if you're a driven person, you're just never going to be completely satisfied unless the world tells you you win a Nobel Peace Prize every day and you're President of the United States or something. And that, that doesn't happen, of course.

• 24:38Ryan Holiday?

  And for people who don't know the title of that book, it's Too Much and Never Enough, right?

• 24:42Speaker 02

  Right.

• 24:43Ryan Holiday?

  Is that something you've had to work on yourself? I imagine you were, you know, very driven, very ambitious, very unsatisfied with just being good enough, because you wouldn't have created your company had you, had you had low standards. But then, once you get to the top, have you had to work on that in yourself?

• 25:03Speaker 02

  Well, I'm not sure. I would say I got lucky in a lot of the things I did. So my business was luck and I had good partners and so forth. And I got involved in a lot of nonprofits and I became the chair of a number of the boards and that was luck. Maybe other people didn't want to be the chair. I don't know. I had a lot of luck. I would say I'm pretty happy with where I am. You know, nobody's ever completely happy with everything, but I'm pretty happy with where I am. And, you know, if I died tomorrow, I would feel I've led a reasonably happy life. And, you know, what can I do?

• 25:33Ryan Holiday?

  Let's say you are looking back reflecting on your life, just because I think it's an interesting thought exercise that might provide some clarity for other people. What accomplishments do you think would strike you as the ones you're most proud of? Is it business, family, philanthropy? How do you look at that?

• 25:52Speaker 02

  Well, I think everybody's legacy who has children is ultimately their children. That's probably the most important legacy. I have three children. They're all in private equity, pursuing the highest calling of mankind, as I like to say. But they're all, you know, well educated, adjusted, they're on their own. They're not, you know, depending on me to die and get a trust fund or something. So I think, you know, they're in reasonably good shape. Second is my mother and father lived to see what I was able to achieve. And so when I do interviews, you may or may not have noticed, but I always like to ask famous people, did your parents live to see your success? Because what can be more thrilling for a parent to see a successful child, or a child to see the parent be happy with what they achieved? And my parents lived to be in their mid 80s and they were pretty happy

• 26:37Speaker 02

  with what I achieved. I didn't say to them, I should have done much more. I wish I had accomplished more. I just said, you know, I'm happy that you're happy. And so that was an accomplishment I was happy about. But I take them, probably the most important thing that people talk to me about now is that I've given back to the country. And it's an interesting thing. I, you know, I've done this patriotic philanthropy and some other things and giving back to the country. And people seem to think that's a good thing to do. And I'm glad that people think that.

• 27:03Ryan Holiday?

  How did that start for you? Like, what was the first thing that you felt compelled to do in terms of patriotic philanthropy?

• 27:10Speaker 02

  Well, yes, I did work in the White House when I was very young for four years. I thought that was giving back to the country. But of course, we got inflation to 15%. So people didn't probably think that was such a great contribution.

• 27:22Ryan Holiday?

  But maybe we can beat that record now.

• 27:26Speaker 02

  It's a hard record to beat, believe me. I would say that

• 27:30Speaker 02

  If you hire McKinsey, or the equivalent of McKinsey, and say, "Give me some ideas of how I can do something useful for society," you know, you'll get some good proposals. But I didn't do that. I stumbled into it. As many good things in life happen, they happen by serendipity. I happened to go to a viewing of the Magna Carta, and they told me it was going to be auctioned off the next night, and was probably going to leave the country, and was the only one in the country, and the only one in private hands. So I just said, "I'm going to go buy it." And so that led to my buying other historic documents, and that led to me fixing the Washington Monument when I heard they had the problems, and so it led to fixing up other buildings. So I kind of stumbled into it. And ultimately, I coined this phrase, patriotic philanthropy, and it's kind of evolved into other things. But, you know, I can't say it was a forethought. I didn't sit down and think, "How can I give

• 28:14Speaker 02

  back to the country?" It kind of happened by happenstance.

• 28:18Ryan Holiday?

  No, and look, I think the books are a big part of that legacy. There's something special about books, in that they kind of punch above their weight, right? Like, however much time and energy you spent, and money spent on the books, I've got to imagine, let's call it a million dollars, I imagine a million dollars into this fund or that fund wouldn't have near the impact as, for whatever reason, a bunch of pages glued together between two covers.

• 28:46Speaker 02

  Well, first, when you write a book, assuming it's reasonably literate, people will think you're reasonably intelligent. So, you know, I think that's good. I like to have people think, just because you're a rich businessman, you're not an idiot, just to happen to stumble into a good business situation. And two, I enjoy writing, and I enjoy reading, and so it's a pleasure to put them together. Also, I guess it's a legacy for my children and grandchildren. They'll see that, "Hey, I actually did something that's still hanging around." I am a collector of rare books, particularly those relating to Americana. And I have a very, very large collection, people tell me, by my normal standards. And I'm thinking about, I'm buying these books that people wrote 100, 200 years ago, and maybe, and nobody's not going to buy my books in 100, 200 years, but the

• 29:29Speaker 02

  fact that there's something that's still around 100, 200 years after you're gone is, you know, interesting. And so I just enjoy writing books. My problem was, I didn't think of doing it, or I didn't have the time to do it. To I, you know, I was in my late 60s. So I wish, you know, I read about some people that had written 30 books. I don't know how they had time to do it, but they actually started earlier. And if you have a routine, you can get that done. I think my former boss Jimmy Carter has written, I think, 28 or 29 books.

• 29:56Ryan Holiday?

  Man, he pumps them out and they're all very good. I've been, I've been, I've read probably four or five of them and I'm, it's almost like he missed his, his actual calling.

• 30:07Speaker 02

  So he, you know, and other people have written books, Richard Posner, one of my former law professors, the University of Chicago, he's written about 30 books. And while he was also a judge and a law professor. So a lot of people are much more productive. Teddy Roosevelt, I think, wrote 30 books or so. I wish I had started earlier. I'm now trying to do one a year and I have a formula, formula to do it. I, you know, I have to give up other things. So I enjoy doing it. I hope my brain will keep going for a while.

• 30:34Ryan Holiday?

  Here's me talking to Ali Abdaal. I, it's weird because I'm both a systems person and not a systems person. Like, so I have my note card thing that I do, but which is very methodical. But then, you know, people often ask me like, sort of what tech tools do you use? Blah, blah, blah, blah, blah. And I'm, I'm sort of very rudimentary in that sense. Do you think, do you think there's, I've always wondered, or I guess been suspicious, if part of why people obsess about systems or tools is that it is a substitute for like actually sitting down and doing the hard part, like coming up with what it is that

• 31:14Ryan Holiday?

  you have to say, or that it's just a way to get distracted with like, all this sort of setup and not sort of just putting your ass in the chair and doing the thing?

• 31:26Ali Abdaal?

  Yeah, I think that is actually a big, a big part of it. I see this in my, in myself, probably a year, a year or so ago, when I was deep down the rabbit hole of researching productivity apps and note taking systems and Zettelcast and all this fancy stuff. And realizing that as a, as a nerd, I enjoy reading about systems and I enjoy the feeling that, you know, and partly why I watched your video was like, ooh. What's a secret sauce? Yeah, it's fine at Ryan's secret sauce. Like, what's the system that if I adopt the system, suddenly, suddenly I'll become a magical bestselling author? And the system is just like a whole load of hard work with that just happens to be on flashcards in your little boxes. I was like, okay, fine. There's, there's no getting around the fact that this actually takes a large amount of work.

• 32:08Ali Abdaal?

  And so actually, I've, I've found myself gravitating more towards simplicity on the tech front as well. Like these days, the only real note-taking app I use is Apple Notes. I dabbled with Rome, dabbled with the Zethel Cast and stuff. We, we use Notion for like team stuff because it works nicely for that. But I find that if I just want to open up something and start writing, even when it's like chapters of my book, I'll just start them off in Apple Notes because I just know it works and knows it's easy. And I feel almost embarrassed screenshotting it and sharing it on YouTube because people, I'm supposed to be some kind of productivity nerd who has all these ridiculously elaborate systems. And actually, yeah, Apple, Apple Notes all the way.

• 32:42Ryan Holiday?

  Well, it's sort of like people set up these sort of Rube Goldberg machines instead of just like getting to the fastest thing, which is, yeah, just sitting down and doing the, the work. Like we, we don't, the, the writing sucks or whatever, the, the making the video or coming up with the idea, that, that's the hard part. So I think sometimes we, it's like we add all this stuff on top. I don't know why, but we do.

• 33:08Ali Abdaal?

  I have an example about this. So recently, we put out a video on the YouTube channel that we had to delete because it was just like objectively bad, clickbait title, bad, bad content, not authentic. And that led me on a whole thing of like figuring out, okay, how do we get to this point where we made a video that was just so bad that the comments were like 50% dislikes and had to be taken down? And I realized that what my issue was, is that ever since I discovered the power of like being able to hire people and delegate and outsource aspects of, of, of create creation. I went too far in the direction of thinking, oh, let me build a system and hire people to fill the system such that I never have to think about a video idea ever again.

• 33:47Ali Abdaal?

  And like my, I, I imagined my dream scenario was one where I could sit down on my desk, speak to a teleprompter and just churn out content. Yeah. I was like, all right, cool. Let's work towards that future and so we hired writers and my researchers and all this, all this kind of stuff. And I realized that, you know, we had like the team staged an intervention Zoom call a few weekends ago, saying that, okay, Ali, maybe we've got a problem. The content is starting to lose its charm because you're not showing up. You're not sitting down and doing the work and coming up with ideas and sort of kind of forming them into videos, because that is the work. That is the hard part. And I thought I could outsource and automate and systemize the hard part. But I realized, oh, my God, like, this is actually just was so misguided. So now we've kind of done a whole 180 on that. And I'm now getting so actively involved back in the content.

• 34:30Ali Abdaal?

  And actually, I'm leaving the management side of the team and stuff to other people in the team who are better at that stuff. So I can just focus on actually sitting down and doing the work of doing the content thing. So I think that that really resonates, that even researching systems, even kind of building human systems, hiring and delegating is often a substitute, at least for me, for actually sitting down and doing the work.

• 34:51Ryan Holiday?

  Well, and it kind of goes back to like, you didn't leave medicine to have a YouTube channel that you don't work on. Like, like you, you left medicine because you liked coming up with and making videos more than doing the other thing. So what kind of life is it where you've also outsourced that, right? I mean, it's, you could call it retirement, which might be, you know, something you do at some point, but like, it is a weird thing. I mean, with writing, you you get successful at it and then you can fill up your whole life with lucrative things that are not that thing. Or you can even pay people to do that thing for you.

• 35:33Ryan Holiday?

  But I just, I always try to remember like, but that's the, that's the thing I like doing. And by the way, that's the thing that I'm, if not the best at, I'm at least world class at, or we wouldn't be here, right? Like, we wouldn't, I wouldn't be able to hire people to do it for me if I wasn't, like, if I hadn't done something new or original in how I do it. And what's, yeah, what's the point of succeeding at a thing if the reward for that thing is you don't do that thing anymore?

• 36:00Ali Abdaal?

  Yeah. Yeah, that's very true, especially in the like, in terms of the whole, like, you know, retirement thing, I, you know, what what that ended up looking like was back to back Zoom meetings every single day.

• 36:10Ali Abdaal?

  Okay, this is not, this is not fun.

• 36:12Ryan Holiday?

  Cause you're still, you're still working. You're just not working on the thing you actually love doing.

• 36:16Ali Abdaal?

  Yeah, yeah. But hey, we've, we've now blocked up, blocked out large amounts of time in the calendar for deep work that no one is allowed to book meetings in. Having all the meetings on Mondays, like it's a trying to, trying to work towards the system. Some of that's, I think, what you've got, you know, wake up in the morning, do a few hours of like four hours or whatever it was of writing, hang out the farm, go for a walk. That, that, that seems like a good life.

• 36:38Ryan Holiday?

  Well, yeah, I mean, I think about it as like, what do you want your life to look like? Work being a part of that life. The idea that you would have a really unhappy life for a large period of time and then go do the thing you actually like, seems to me to be a risky bet.

• 36:52Ali Abdaal?

  Yeah, deferred life plan.

• 36:54Ryan Holiday?

  Yeah, yeah, yeah. Um, so speaking of productivity, I mean, obviously you, you do get a lot done. If you had to think about like, what are the biggest tools for you as far as being more productive? Like if someone's like, I'm just a mess, like my life's just a mess. Where would you start?

• 37:12Ali Abdaal?

  Oh, okay. Um, so there's like one underlying theme and then a few tools to help. The underlying theme is for me, I found that actually just optimizing for what's fun has been the single biggest hack for my productivity ever. Um, and finding like that, partly that's like choosing to do a thing which I happen to find fun, you know, follow your passion stuff. But it was, it's, it's only recently that I've had the freedom to be able to do that. For the rest of my life, it was doing things other people slash the schooling system was telling me to do. But even in those, finding ways to make them fun. Um, and so now my, my advice for most people, if they're struggling with productivity is find a way to make it fun. Uh, that's all, you know, all easier, a lot, a lot easier said than done. Um, in, in terms of

• 37:55Ali Abdaal?

  specific tools for, for, for, for, for getting more done, single biggest tip I found is, um, something I came across in a book called Make Time by Jake Knapp and John Zeratsky. They call it the daily highlight. I think similar to Gary Kalas' idea of the one thing like what, what's, what's the one thing I actually want to do today? And I ask myself this every morning, like what's the one thing? All right, cool. Write, write that down. And honestly, if, if I could actually just do that one thing that's most important to me every single day for 365 days, that would completely move the needle on my productivity. Um, so if I only could choose one thing, that would be what I, what I would suggest. If I could choose two things, it would be, uh, deciding what that one thing is and then putting it on the calendar. Because when it's on the calendar, it's going to get done. And if it's not on the calendar, it's, it's not going to get done.

• 38:39Ryan Holiday?

  Do you think about, I guess this connects to the idea of the one thing which I think about is like, and this also goes to the point about delegating, which is like, what is the thing that only you can do? Right? Like, to me, a great organization exploits the law of comparative advantage, which is that everyone should do the thing that they are best at, right? And then we all come together and then we're this sort of superhuman or super organization where you have a bunch of people doing the best thing. This is how a sports team works, right? Not everyone plays whatever position, they just assign people randomly. It's like, you have the best quarterback, you have the best linebackers, you have the best safeties, you have the best players. But I think that's really important, especially if you're in charge of the team,

• 39:23Ryan Holiday?

  which is like, what is your thing? The thing that only you can do? And then, how do you, as you said, make time for that, block it out in the calendar? And conversely, how do you hire people to support or take off your plate all the things that are not that thing?

• 39:43Ali Abdaal?

  Yeah, yeah, absolutely. I did one of those like matrix exercises where it's like, things I love to do and I'm great at, things I like to do and I'm good at, things I don't like to do and I'm good at, and things I hate to do.

• 39:56Ryan Holiday?

  What's that called?

• 39:56Ali Abdaal?

  Can't remember. It was within a book called Attraction by Dino someone, yeah, this is what I was reading. And I did that exercise. I was like, oh, okay, there's a lot of things in this, in the bottom two quadrants, i.e. things I don't like to do, that I am good at slash not good at. And I realized I actually could just write all of those down. And this was how I ended up finding a personal assistant. And genuinely, I feel like, these days, anytime I speak to a sort of creator or entrepreneur, and they don't have a personal assistant, I try and sell them on the idea of just getting a part-time personal assistant. But I think if you can offload those bits that you don't like, that someone else could do, it just gives more of your time to do the stuff you enjoy.

• 40:35Ryan Holiday?

  Here's me talking to the economist Emily Oster. I was fascinated by the Bloomberg profile of you and your family. It sounds like your mother and father had a very interesting way of raising you and your siblings.

• 40:52Speaker 04

  Really? I mean, I think that they, yeah, I guess everybody's family is kind of weird in their own way. And so when you're in the family, you're like, oh, this is totally how everyone does it. And then, you know, when you meet your spouse and you go to their family, you're like, oh, I guess not everybody does it like that.

• 41:07Ryan Holiday?

  But like they were saying, like alternating which days they cooked to show that the role should be shared, even like how you got one last name and your other siblings got a different last name.

• 41:19Speaker 04

  Yeah, yeah, I think that, you know, for my mom, you know, she was a kind of 1970s feminist. And for her, a lot of these, this, like, there were a lot of aspects of modeling that that were just very in the concrete. So, you know, beyond saying men and women are equal, like literally trying to show us that, you know, you could kind of both do all of the things. I think that was just for her, that was a really important way to show that.

• 41:47Ryan Holiday?

  No, but I love that because, I mean, isn't that what parenting is supposed to be? Like, it's easy to say, here's what I believe, here's what's true. And then as a parent, I think you struggle to, you know, like, actually live up to what you think is important.

• 42:01Speaker 04

  Yeah, it's interesting because there's a sort of, there's a little bit of a problem from this from an economist standpoint, because actually, within economics, it is not really that you should split the things exactly evenly, right? Like, people should do the things that they are relatively better at.

• 42:18Ryan Holiday?

  Comparative advantage.

• 42:19Speaker 04

  Comparative advantage. And so actually, my father is a terrible cook, like legitimately terrible. And so like, it was like, you know, every, it wasn't really that great an idea to have him cook every other day because he only could go like two things.

• 42:32Ryan Holiday?

  Right.

• 42:33Speaker 04

  And so you had, you know, and my mom is a fantastic cook. So it would be like, every day, you know, you'd come home, be like, who's cooking today? It was dad, it was like, sesame chicken. That's it. And so, you know, there was this sort of tension about like efficiency versus equity.

• 42:49Ryan Holiday?

  No, it's funny how, I mean, obviously, I'm sure in other cases, it's not true, but it is. It is interesting how much sort of like gender roles can be revealed in the course of these sort of ordinary parental tasks. Like, I remember my dad, so my mom worked a lot, so she would work at night sometimes. She was a school principal at a school that also had night classes. And when my dad would cook, my dad would cook us, he'd cook like ramen noodles, and then he would melt cheese in it. Like, he would put, he called it cheesy soup. And in retrospect, it's so disgusting to even comprehend eating that. But you're also learning the lesson, the same one your parents are teaching, which is that like, the parent's job is to cook dinner for the kids, not the mom's job or the dad's job.

• 43:34Speaker 04

  Yeah, no, I think that's, I think that's right. I mean, I will say, in my family, I do all the cooking. But, but my husband does all of the dishwasher. So, we've sort of split it in a slightly different way, but at least, you know, the kids see kind of both people are, and that both people are contributing to like, making sure the house is functioning.

• 43:52Ryan Holiday?

  Yes, right. And you kind of also have to choose your battles as far as like, what lessons, like, where do you really want to show, like, here's, I mean what I say. Is it, is it to the point where we all have to eat inedible food? Or should we find, you know, bigger battles to fight?

• 44:10Speaker 04

  Yeah, exactly. There's like a sort of, there's like, which hill do you want to die on?

• 44:14Ryan Holiday?

  So, so going to this idea, some of the gender stuff, I was curious about it, because I feel like this is partly why your books have resonated and why I like them, but, but why so many of my wife's friends have liked them as well. Am I wrong in picking up that, like, moms seem to be like a thousand times harder on themselves than fathers? And where is that coming from?

• 44:36Speaker 04

  Yeah, I don't, I mean, I think you're definitely right. How much of that is like societal pressure as opposed to like, you know, uh, like how much you put on, on yourself? I've never quite worked out. Like, I think, you know, the sort of, there's this trope, which is of course a trope, but also not totally wrong, where people feel like, you know, if you, like, when I'm watching the kid for the day, like, everyone should be thinking like, wow, I learned a lot and it was like, and I, I mastered a new skill and the, you know, and, and, and also we had the 17 course bento meal. You know, and then when, you know, when he's watching the kid for the day, it's like, oh, they're not dead. So I, I went, you know, and so somehow like the, the standards are really weird.

• 45:20Speaker 04

  And I do think that it's both society, it's both society and it's, um, you know, and it's probably partially pressure people put on, put on themselves.

• 45:28Ryan Holiday?

  Um. Yeah, there was a story I, I liked one time where Stuart Scott, the, the late ESPN broadcaster was having like, uh, it was, took his, his two daughters out to lunch and they're sitting there with a friend and their kids and someone who recognized him came up and said, oh, it's so great to see you babysitting. And he said, I'm not a fucking babysitter. Like this is my, this is my job, you know, like, but there is an element where it's like, yeah, as a father, it's like, if the kids are alive, success. And a mother, you're judged on, you're judged against the greatest mother who ever lived. And, you know, the TV image of a mother and all these things.

• 46:05Speaker 04

  Right. I, yeah, I think it's not even the greatest mother who ever lived. It's like what other people think that, think is the greatest mother, whoever, you know, like, there's not like there's one version of that that like you could aspire to. It's just like what they think that, you know, should, should be happening.

• 46:19Ryan Holiday?

  Yeah. And there, there's a thing I think that, that the Stoics would sort of point out about that. That's interesting where it's like, there, there does seem to be this like kind of contest women are in with other women about like sort of who can be the most pure, authentic, you know, natural mother. And men obviously have tons of ridiculous contests that we get in with other men. But, but it's, it's, I think in both cases, it's sort of this idea is like, what is making your, you feel like a piece of shit about it? How does it make you better at that thing?

• 46:50Speaker 04

  Right. No, I totally agree. I mean, I think it's not, you know, making other people feel bad is something that we seem to think is a way that we can make ourselves feel good, which is not obvious.

• 46:59Ryan Holiday?

  There's this thing where I think we, I guess what I'm saying is beating on yourself for not being good enough, for not doing it perfectly, it not only doesn't help you, but it doesn't help your kids or anyone. So there's this kind of guilt that we add on top that is not additive really in any way.

• 47:16Speaker 04

  Yeah, no, exactly. It's sort of like somehow by, by feeling bad about things, I am somehow positively contributing to the experience of my, of my children. I think this comes up in pregnancy also around like sort of denying things, right? The idea that like, you know, well, if you're like, you know, well, if you can go without coffee, even if there's like no reason to do it, just the act of kind of making that sacrifice, that is what makes you a good parent. As opposed to like, just, you know, that's just something that makes you miserable and doesn't help your baby.

• 47:48Ryan Holiday?

  Yeah, right. And, and I know some of the studies of it have been sort of disproven or whatever, but I think personally, most people, it's like you only have so much willpower. I think we, we can kind of admit that, that we only have so much energy and we only have so much sort of self-discipline. What are you going to spend it on is a really important question.

• 48:11Speaker 04

  Yeah, yeah. I think you have to like, and we only have so many like mental and physical resources, right? That like you just can't, you can't do all of these things and, and or then you tried to do all of them and you kind of lose it. And now you've, now you yell at your kid. And but that, well, that's also bad. You know, now you did that thing wrong.

• 48:29Ryan Holiday?

  Right, right. Yeah, no, you, you feeling like you're not good enough, you feeling like, you know, you're, you're crappy compared to other moms or dads, et cetera. It isn't making you better with this little person who, who needs you to be strong and confident in all, all these things that parenting requires.

• 48:48Speaker 04

  And happy. Like, I mean, your kids want, like, if you're, if you are happy, that is a way for them to also be happy.

• 48:57Ryan Holiday?

  So where does the premise of your work, which I think is interesting? I was just talking to Tom Ricks, who wrote this book called First Principles, which is really about what did the founders believe as they were creating America? But the concept of first principles seems to kind of be at the root of your work, which is in the sense that you're like, you know, instead of just assuming that all of these things are true, all these sort of lessons or rules or guidelines, why don't we actually explore them and see if this is worth doing, this is not worth doing? Is that sort of how you think about your work?

• 49:33Speaker 04

  Yeah, I mean, I think about my work as basically saying, you know, people told you to do a lot of different stuff. And, you know, especially actually in this world in which you kind of can't do everything, where you're sort of, you're limited in your capacity or willpower, your time, or whatever it is, that it actually is pretty valuable to have those things ranked. And, you know, rather than saying like every single, you know, it's very important that you breastfeed and not co-sleep and that your kid is not in your, they're not in your bed, but they are in your room and that they do that for a year. And also, you know, that you do all these other 50 things, like actually identifying what does the data say about which of these is most important? And, you know, which of them are maybe, maybe even if they matter, that they matter less.

• 50:16Speaker 04

  And that lets you like make informed decisions in a world of constraints. I mean, economics is all about, right? Like optimizing under constraints. And I think sometimes we just assume that parents have like 75 hours in every day. So they know they don't face constraints, but that turns out not to be true.

• 50:33Ryan Holiday?

  Well, and even I think there's also probably some guilt slash fear of optimizing, which implies compromise as a parent, as opposed to just doing everything perfectly, exactly how you'd want it to be.

• 50:46Speaker 04

  Yeah, I think people want, people, people don't want to say like, well, I, you know, even though this thing was like a little bit good, I kind of didn't have the capacity to do it. But I think we should be able to say that because of course, like if you, you know, if you... You may literally be impossible to do all the things people tell you to do.

• 51:04Ryan Holiday?

  Well, I feel like from what I've read of your stuff where it's like, look, if you know that the choice you're making is for the most part rooted in data, then you can feel good about it, even if other people think you're crazy or weird. Marcus really says this great line where he says, "We love ourselves more than other people, but we care about other people's opinion more than our own." There seems to be an element of parenting where it's like, even though we all have pretty good intuition and maybe we have our own experiences, we really just want to make sure we're not doing something weird compared to what our kids, friends, parents are doing.

• 51:41Speaker 04

  Yeah, and I think the other piece of it is not so much, part of it is sort of knowing like what the data says, and then part of it is just knowing that you thought about it. So I think that some of what I'm sort of delivering in the books is like, look, here's like, here's a kind of opportunity for you to sit down and think about, you know, what are the choices I'm going to face? What does the evidence say? How should I think about my preferences? And then to kind of come out and say, okay, well, I decided like to breastfeed, or I decided not to breastfeed, and I decided it because I looked at the evidence and I thought about it, I thought about what worked for me. And then when someone is like, "Oh, you're not breastfeeding?" Then it's a little bit easier to be like, "I'm not breastfeeding, and I thought about it, and I'm not doing it because it's not the thing that works for me." As opposed to just being like, "Oh my God, that person is judging me. Like, maybe I am doing it wrong."

• 52:25Ryan Holiday?

  Right. And also, I'm not like knowing that you're not not doing it because it's hard, right? You know what I mean? Like, you're doing it, there's a logic to your actions.

• 52:36Speaker 04

  Exactly. You made that decision for a reason, not just because you just like on a whim one day, you know, decided that that just wasn't going to be for you.

• 52:46Ryan Holiday?

  Here's me talking to venture capitalist Brad Feld.

• 52:51Ryan Holiday?

  If you're lucky enough to be successful, right? So you start some small tech company and for the first several months or several years, you're maniacally focused on product, customer acquisition and all these things. But if you're lucky enough to be successful, soon enough, you're bumping into the timeless questions of philosophy, which is dealing with other people, dealing with temptation, dealing with focus, trying to find a balance, you know, human psychology, a purpose, meaning, all those questions become not just part of the purview of a leader, but you could argue, as the company becomes really successful, pretty much entirely what the founder should

• 53:36Ryan Holiday?

  be thinking about because they shouldn't be micromanaging all these sort of day-to-day product things. They should be thinking about where does this company fit in the world? Where is the world going? How do I get the most out of the people who have decided to entrust me with their time and retirement savings and all these things?

• 53:56Speaker 05

  Let's play with an important word that you said for a moment, which is meaning.

• 54:00Ryan Holiday?

  Yep.

• 54:01Speaker 05

  And it's so important because so much of entrepreneurship is filled with cliches about what to do and how to do it, or even why you should do it, or what success and accomplishment is. But very rarely do any of those cliches land on real meaning. And often, in some ways, they're really antithetical to the whole notion of meaning. And an example would be the number of entrepreneurs who say, "I want to be an entrepreneur because I want to change the world."

• 54:42Speaker 05

  Or the Steve Jobs cliche of, "I want to put a dent in the..." "Are you going to put a dent in the universe?" And sort of the whole notion that an entrepreneur is approaching that extraordinary impact, right, to change the world.

• 55:04Speaker 05

  In such a casual statement, right? My goal of creating this company is to change the world. What does that actually mean?

• 55:12Ryan Holiday?

  Yeah, that's only the first part of the sentence, right? What are you trying to? Not just why are you changing the world, but what change? I mean, a lot of horrible people have changed the world too, for the worse.

• 55:23Speaker 05

  And it's a, there's a lot of things, you know, where you say, well, I changed the world. And it's like, yeah, except for, for the last, you know, 2,000 years. That change happens every 20 years.

• 55:36Ryan Holiday?

  Oh, sure.

• 55:37Speaker 05

  30 years, like you, you didn't really change the world. You just played a pattern that keeps playing out over and over again. And, and that's just at the functional level of the business. Then you think about, you know, the behavior of the person.

• 55:51Speaker 05

  And, you know, the experience that you have and play with another word, which is why? Why are you doing this? What is the meaning of, of what you are doing? You know, what, what is your own why?

• 56:06Ryan Holiday?

  Yeah.

• 56:07Speaker 05

  And as you, you know, have failure or success or some of both, does the why change? And interestingly, do you ever accomplish your why? And then what? And these are all real questions about being a human and being, you know, part of this species on this planet. And it doesn't have to do with 2021. It could, right? You can instantiate it in 2021. But in, in the context of long arc of meaning, what again does that matter?

• 56:49Speaker 05

  And I think entrepreneurs who don't spend any time going deep on that within themselves. And frankly, it's entrepreneurs or people. Are missing such a huge element of the experience of existence. And at the core, that's the essence of philosophy over a long period of our species.

• 57:10Ryan Holiday?

  Yeah, to flash forward, you mentioned the idea of these trends happening every 20 or 30 years, and that's a hint at Nietzsche's sort of concept of eternal recurrence. But I am struck, for instance, and I remember being struck reading at 20 years old, Marcus Aurelius, and you have this incredibly powerful, successful person who did change the world, sort of meditating on not how meaningless it was, but that it didn't mean what he thought it was going to mean, or he was sort of, it's like he got to the top of the mountain and he wanted to tell people like, hey, don't give up your entire life to get up here because it's not exactly what you think. I am amazed, you know, the number of people who get into entrepreneurship because they

• 57:55Ryan Holiday?

  want to be the richest, or they want to like do this thing that they've seen other people do, even though if you look closely at it, those people sort of also warn against trying to do that. So there's this weird tendency where we're all chasing this thing and then conveniently forgetting that people have gotten there before us and come back to say like, hey, make sure you're doing this for the right reasons.

• 58:27Speaker 05

  Well, the very powerful ending arc of that, I keep a copy of your book, The Daily Stoic, in the bathroom. And each morning I read whatever that day is. And I particularly like December because, you know, December is about mortality and death. And I'm reading a book right now called Quantum, I lost the last name of it.

• 59:04Speaker 05

  It's by David Kaiser. And it's sort of about, he's a physicist and historian. And it's sort of about the different arcs of quantum thinking and all the different things that have happened along the way. And it's both the specifics and the sort of the philosophy of it. And this notion that, you know, there's this big struggle in quantum physics today around, you know, the big bang starting 14 billion years ago. And the different philosophies of, or the different thesis. I don't want to say, I guess they're theories. I was gonna say thesis, but I guess they're really theories of,

• 59:48Speaker 05

  well, what happened immediately before the big bang? And if the universe, is the universe really infinite or is it finite? And then there's now the multiple parallel universe theory that is picking up some steam is that there's this continual instantiation of multiple parallel universes. And this whole notion that as a, as a human being, right? You know, our lifespan is less than, less than 100 years or 100 years would be a very long life for somebody. And the idea that we're 14 billion years into the existing universe that we're in as current quantum philosophy has. And then on top of all of that,

• 1:00:33Speaker 05

  the notion that if you sort of scale way back and look at it, it's kind of no different than, in some ways, a different flavor of religion, right? It's the creation myth of the universe and the role of humans in the context of the universe. And today, we have such a deep understanding in just in the last 100 years of so much more of what's going on than, you know, 2,000 years ago in terms of the mechanics of everything. But if you go back 2,000 years and you think about this notion of meaning, those patterns play out over and over and over again.

• 1:01:13Speaker 05

  Right? The Joseph Campbell hero arc, the incredibly successful person who dies unhappy or penniless, or some tragedy occurs along the way, and even though they had incredible success, you know, the loss of child, family, country, whatever. I mean, these things just play out over and over and over again, and we imbue so much meaning in them. Philosophy and studying philosophy and applying it to our lives gives us a moment to really step back and go deeper on the meaning to us.

• 1:01:57Speaker 05

  Forget about the meaning to everyone else. Forget about what we're told is important. But that introspection and playing around with it is so powerful.

• 1:02:09Ryan Holiday?

  Here's me talking to Randall Stutman. We briefly touched on ego and managing up. Having written Ego is the Enemy, it's ironic, I get all the time, people go, what do I do about my boss's ego? And I usually try to turn it around and go, why don't you focus on yours? Right? You know, that you're asking me about someone else's ego first. But what do you do? How does one get better at managing up or leading up when, you know, they're not the ones that get final say? Right? You can put together the most brilliant plan, you can assemble the most brilliant team, but how do you deal with the difficulty of somebody else also leading you as you are leading others?

• 1:02:54Speaker 06

  Well, you're gonna have to learn how to carry feedback upwards. And sometimes it's about getting curious and asking questions. Like, why do you do what you do? Like, why is this your stance? Like, tell me, like, it just doesn't, it doesn't occur to me, it's not my intuition to think in this particular way. You're the leader, you're somebody that has more experience than I do. Explain that to me. And what you'll oftentimes is just by asking the question. You will shake people up. You will get them to rethink their premises or start thinking about. So for example, you know, you were using the example of yelling in the organization. That doesn't happen very much anymore, but occasionally it does. We'll see organizational cultures that are highly negative. Where the only thing positive is, you know, drug tests and things. But nonetheless, right?

• 1:03:39Speaker 06

  You know, if you had somebody that would yell all the time and say, hey, like, you know, it's not my instinct to yell. So tell me, what do you think it achieves? And tell me why you do it. Maybe I'm going to double down. I don't know, but like, explain it to me. And then what you're going to wind up hearing is, I don't yell. Actually, I think you do, right? Well, so you tell me it's not intentional? Well, what do you mean? I mean, I guess I raise my voice sometimes. And that's all it takes. I mean, that's a big deal. Asking questions in a curious way and carrying feedback, the most negative feedback with questions, is a very, very important way to leading up, right? But here's, here's, you know, my favorite ego, I don't think I've ever shared this with you. My favorite ego story is a Lyndon Johnson story. So Johnson's coming out of the White House. He's coming in, it's a true story because it's written by a Secret Service person who wrote this.

• 1:04:23Speaker 06

  And he's coming out of the White House, talking to reporters through the Rose Garden, walking to a helicopter. It's two helicopters on two different pads. They had just met with some dignitaries and they were going to take those dignitaries someplace else within one helicopter. And because he's talking to the press with his back to things, he's walking to the wrong helicopter. He's moving to the wrong helicopter. So the Secret Service guy taps him on the shoulder and says, President Johnson, you're moving to the wrong helicopter. That's not your helicopter. And Johnson gets a big smile on his face and puts his arm around him and says, son, they're all my helicopters. Okay? This idea of ownership is the biggest problem that I face when we come to ego in organizations. Great leaders are stewards.

• 1:05:07Speaker 06

  They're stewards of their kids, they're stewards of their marriages, they're stewards of their teams, they're stewards of their organizations. We don't own anything, okay? And the moment you have that in your mentality, it really is a problem. So here's my point. The reason I bring that up is not just to tell you a fun story that I like. It's that when you ask me, how do I influence the person upward? Part of it is to say, right, okay, we don't own this, we're stewards of this. So tell me, show me, and you don't have to say it this way. How is this, how are we maintaining this over time? What's the long strategy here? How are we retaining people through these actions? What, what's the stewardship here? And explain to me how it is you're, you and I are acting like stewards. And again, don't say it directly that way.

• 1:05:52Speaker 06

  But when you ask that question, again, you will shake people up because you now remind them of what their true role is. And when you remind people that they're stewards instead of owners, they act entirely differently.

• 1:06:05Ryan Holiday?

  I love that. I was, I was just thinking about that as a business decision on something that, that I own. Like, I was thinking about the profits that are coming in, the revenue that's coming in, and thinking about what is my obligation as the, not as the owner of the business, but as the steward of the business? What is my obligation to invest that? Is advertising my grow it? But is that the best, most honorable use of the funds? Might it be better to do X, Y, and Z instead? And, and I, so I just wrote this down. Am I being a good steward? I think is a question leaders should ask themselves.

• 1:06:39Speaker 06

  Absolutely. And you can ask that of your leader without doing it directly. You can say, how is this, how is this? Cause almost all long-term, right? What's best for the business of it, you know? Anything that isn't about you in the center of it is moving towards stewardship, right? But it's the idea intentionally. My goal and my job is to actually shepherd, right? Where this goes and to keep it alive and to maintain the highest effectiveness and efficiency and efficacy that we can. That's stewardship. When you start owning stuff, which people do so quickly. They own their kids, they own their marriage, they own their houses, they own everything. They're not stewards of things. And as a result, they operate very differently as leaders.

• 1:07:19Ryan Holiday?

  So last question, uh, cause it pertains to that. And I saw some people mention it and I know it's come up. Uh, I've seen you talk to, to different leaders about it. Um, there's that expression and excuse the, the gendered nature of it, but it only works this way if you rhyme, uh, cause it rhymes. Uh, happy wife, happy life, right? How do you think about leadership and their personal life?

• 1:07:41Ryan Holiday?

  Applying being a leader at home, applying, having a balanced, happy home so that you're not bringing your garbage to the office and you're not bringing your garbage from the office home.

• 1:07:53Speaker 06

  So, so three things, there's three things in there that I'm gonna unpack. So this is gonna be, gonna be a long answer, but I think

• 1:07:58Ryan Holiday?

  I love it.

• 1:07:59Speaker 06

  Right? So, so the first thing is, your job as a leader is to make really fast transitions. By that is, you play many different roles in many different places. Your job is not to carry the last conversation. So forget about, you know, how happy things are. Your job is not to carry the last conversation to this conversation. If you're gonna be entirely attentive to me, it's about our conversation. So even during the workday, you know, you, you just had a conversation. We just, we just did this, this conversation. You can't, you can't let that influence what's gonna happen next by mood, by, by focus, by lack of focus, whatever else. Your job is to make fast transitions.

• 1:08:36Ryan Holiday?

  Sure.

• 1:08:37Speaker 06

  And so you've got to, if that means you need to settle yourself and sit out in your car for a couple of minutes before you walk in the house, so you can now be dad, then that's what you need to do. But your job is not to walk into that house and carry with you forward anything that came from before, and that's about conversation. It isn't about happy. It isn't about, you know, disappointment. It's about conversation. And because all of those things reside in conversation. So your job is to make transitions, fast ones, from conversation to conversation, and carry them forward. Right? So that, that's, that's my first piece. My, my second answer, or kind of like, you know, engagement around that idea of, of happy is, listen, this happens to me all the time. I'll, I'll study somebody

• 1:09:20Speaker 06

  and they'll say, I'm, I'm really good at relationships. I go, really? Tell me about that. And he goes, I'm really good with my friends. Have a great marriage. Not so good with my, my colleagues. Not good with my leader. Okay with my clients. What I know is they suck everywhere. They just don't know. Because you can't be good, I mean, really good in one spot. You've never met anyone that wakes up and, you know, who's fast and then wakes up slow. You never meet anyone that's like really smart and then one day they just, they're stupid, right? You know, excellence doesn't turn itself or turn itself on or off. It just doesn't. And so the question really is, is when people tell me like, you know, they need, they need a certain context. I have to be happy here to be happy here. My response is like, okay, it sounds to me like you're not happy anywhere.

• 1:10:05Speaker 06

  So let's figure it all out because it isn't a segue between this and that. You're just not, you're not achieving, you're not hitting on all cylinders every place. So let's figure that out. Right? Because this, you're overestimating yourself, which we all do. Okay. That you're thinking it's more about X than it is Y. It's both of those things. Right? They're happening. You can't turn excellence on and off. Right? My third answer to that is this idea, this idea of work-life balance has created such a horrible metaphor in 2021. It isn't, wasn't a horrible metaphor in 1960, by the way. But, but because we asked for different commitments, there was different engagement. It was an entirely different way of organizing ourselves and like, but in 2021, there is no work-life balance. It's an integrated whole.

• 1:10:50Speaker 06

  Right? It's, it's work-life, you know, Bezos calls it work-life harmony. And I don't like most of Bezos' stuff, but he's got that one right. It's a harmonious way of connecting all the dots. So that you integrate pieces, people that aren't talking to their, the people that matter the most to them in life. You're not talking to your kids all day long. I don't mean little nano texts or whatever else. And you're saying, well, I'm going to save that for the weekend. What I know is you're out of balance. Okay? You haven't integrated in your life. Okay? And so I want all of those things integrated and what you're going to find is when you integrate and create a harmonious balance in your life about everything you're doing. So everything that's important happens all the time. What you're going to find is everything happy.

• 1:11:33Speaker 06

  Has an influence and shaping of everything else. And everything that's unhappy, you have the ability to put in context and keep it. And so happiness will spread itself, if you will, if you're fully integrated. Satisfaction will spread itself. Pride, all the good virtues will spread themselves. And the other things will become moments in time that you can get past. So to me, it's all about integrating and creating a whole rather than separating things out. When we subordinate and separate things out, we get ourselves in trouble as leaders. When I say I worry about the relationship and how people see me later, I've got to get the task done. I'm going to subordinate that to later. Later is one of the biggest dangers that we all face. Everything can be done later. I can procrastinate and do it later.

• 1:12:18Speaker 06

  I can talk about my relationships later. I can push this off for the weekend. We're going to have really quality time this weekend, Ryan, by the way. Okay. And what I'm doing is I'm basically not integrating the whole. And as a result, I'm being less effective as I should be as a leader. And I'm making everybody around me less effective as a result.

• 1:12:36Ryan Holiday?

  No, I love that. You said we didn't quite disagree, but maybe this is a minor point of disagreement. I would say that I have, I would say that I have found that professional mastery. So work on your work does not translate into personal happiness. But personal work, personal development can translate into professional excellence. So that it's, it's not quite a two way street. So the work you do on your relationship with your kids at your home, how your health, all those things can have, can pay real dividends at the office.

• 1:13:10Speaker 06

  Agreed.

• 1:13:11Ryan Holiday?

  You can work 50 hours a week, and that's not a lot. You can work all the time at the office and build a great, you know, workplace culture. That doesn't immediately translate to home the same way that.

• 1:13:25Speaker 06

  You're right, we disagree because you used apples and oranges. You went from a place of saying, I've got, you know, this family and you use a couple of descriptors. I've lost them already. And then you went to say 50 hours and right. What I want you to bring from that work is excitement and pride. Right? And satisfaction of result and those things, right? So when when your kids ask you, why you're, why are you going? Why are you leaving every morning? Like, why are you going away? And you don't, you don't say, because I need to work, right? What you say is, I have this tremendous need to teach and engage other people. And I hope to share that with you, and I can't wait to do it. And then I can't wait to come back with you because we're going to have this, right? There's so many things that you should should, if you're doing it correctly,

• 1:14:09Speaker 06

  that you should be bringing back from work that that should instill in your family and personal relationships in a way that betters them. We just don't think of them that way because we don't compare apples and apples.

• 1:14:20Ryan Holiday?

  That's true. I I guess I would just say there's lots of champions and billionaires and and well-respected artists, etc., who are very good at what they do, but are shitty at home. I would argue there's a lot fewer people who have wonderful, happy, you know, actualized home lives who are not good at the office. Or whatever their profession.

• 1:14:46Speaker 06

  I agree with a hundred percent of that. But here's what I'll tell you, of those musicians and artists and everybody else you described that are really good at what they do, but you know, but are shitty at home, I'm going to guess, I'm going to bet, right? That if I went in there and you and I went and looked at them, they're shitty with the other people that they work with too.

• 1:15:01Ryan Holiday?

  And they could be better at what they do.

• 1:15:02Speaker 06

  It's all, it's all about, and it would make them better. They're all, it's all about relationships, but their talents are so significant that they're able to to do to succeed despite themselves.

• 1:15:12Ryan Holiday?

  Yes.

• 1:15:12Speaker 06

  And and that happens all the time.

• 1:15:15Ryan Holiday?

  Yes. No, to me, that's the point about ego too. It's not that people with egos are never successful. It's that egotistical people could have been more successful if they could have gotten out of their own way.

• 1:15:26Speaker 06

  Oh, a hundred percent. Wow. We see we ended on agreement.

• 1:15:30Ryan Holiday?

  We ended on agreement. Randall, thank you so much. This was amazing. Appreciate it, everyone.

• 1:15:34Speaker 06

  Great talk with you. Good luck with all of this and we'll talk soon.

• 1:15:37Ryan Holiday?

  We will. All right. Talk soon.

• 1:15:39Speaker 06

  Bye bye.

• 1:15:42Ryan Holiday?

  Demand more of yourself in 2022. And one of the ways you can do that is by joining us in the Daily Stoic New Year, New You Challenge. All you have to do is go to dailystoic.com/challenge to sign up. Remember, Daily Stoic Life members get this challenge and all our challenges for free. But sign up, seriously. Think about what one positive change, one good new habit is worth to you. Think about what could be possible if you handed yourself over to a little bit of a program. We all pushed ourselves together. That's what we're going to do in the challenge. I'm going to be doing it. I do the challenges, all of them, alongside everyone else. I'm looking forward to connecting with everyone in the Discord challenge, all the other bonuses. Anyways, check it out. New

• 1:16:25Ryan Holiday?

  Year, New You, the Daily Stoic Challenge. Sign up at dailystoic.com/challenge.