Alex Lieberman on Defining Values, Restraining Opinion, and Curating Wisdom

Ryan talks to Morning Brew founder Alex Lieberman about his journey with Stoicism, the false belief that money can change your level of happiness, the higher standard that leaders should hold themselves to, the power of restraining opinion, and more. Alex Lieberman is the co-founder and Executive Chairman of Morning Brew. Alex started Morning Brew as a college student in 2015 and has grown it to over 3 million subscribers. Alex is also the host of the podcast Founder’s Journal, which offers a backstage pass into building Morning Brew. Sign up for Daily Stoic Life to get a members-only gift set, access to all of the Daily Stoic Courses, bonus weekend meditations, and more at dailystoiclife.comGiveWell is the best site for figuring out how and where to donate your money to have the greatest impact. Go to Givewell.org to read more about their research or donate to any of their recommended charities. Enter Daily Stoic at checkout so they know we sent you. Eight Sleep is the most advanced solution on the market for thermoregulation. It pairs dynamic cooling and heating with biometric tracking. Go to eightsleep.com/dailystoic to check out the Pod Pro Cover and save $150 at checkout. LinkedIn Jobs helps you find the candidates you want to talk to, faster. Every week, nearly 40 million job seekers visit LinkedIn? Post your job for free at LinkedIn.com/STOIC. Terms and conditions apply. Stamps.com makes it easy to mail and ship right from your computer. Use our promo code STOIC to get a special offer that includes a 4-week trial PLUS free postage and a digital scale. Go to Stamps.com, click on the microphone at the TOP of the homepage and type in STOIC. 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, FacebookFollow Alex Lieberman: Twitter, Instagram, HomepageSee 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 weekend edition of the Daily Stoic. Each weekday, we bring you a meditation inspired by the ancient Stoics, something to help you live up to those four Stoic virtues of courage, justice, temperance, and wisdom. And then here on the weekend, we take a deeper dive into those same topics. We interview Stoic philosophers. We explore at length how these Stoic ideas can be applied to our actual lives and the challenging issues of our time. Here on the weekend, when you have a little bit more space, when things have slowed down, be sure to take some time to think, to go for a walk, to sit with your journal,

• 0:46Ryan Holiday?

  and most importantly, to prepare for what the week ahead may bring. Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. I love newsletters, of course. Daily Stoic is a newsletter. If you didn't know that, well, you should definitely subscribe. Daily Dad is a daily newsletter we do. There's a bunch of newsletters I like. I've gotten Maria Popova's Brain Pickings newsletter for many, many years. She just renamed it The Marginalia. I like Emily Oster's Parenting Newsletter. That's a great one that I get. I love Tim Ferriss's Five Bullet Friday. That's a great one that I get. One of my researchers, Billy Oppenheimer, has a great newsletter that I love

• 1:29Ryan Holiday?

  that you can sign up for at BillyOppenheimer.com. I like Matt Levine's newsletter for Bloomberg money stuff. I like The Dispatch, David French especially. I love Andrew Sullivan. I love Heather Cox Richardson's newsletter, Letters from an American. I just love newsletters. They're great. It's a great way to get information. They're not filled with ads. It's not a bunch of stuff to click. You read it in the browser. You read it on your phone. You print them out. Just a newsletter I love. It's been a great way for me to learn over the years and, of course, been transformative for me. My Reading List newsletter, which I started like a A decade ago is now a bookstore. The Painted Porch Bookstore here in Bastrop, Texas would not

• 2:14Ryan Holiday?

  exist if I hadn't started that newsletter where I just recommended my favorite books that I read each month, which I'd love to have you sign up for if you haven't. And again, Daily Stoic being the newsletter that fundamentally changed my life and is now the largest collection of Stoics anywhere in the world. So, one of the fastest growing newsletters in recent history has been Morning Brew, sort of a media business newsletter, supposed to give millennials, young people like a rundown of everything that's happening in the world. And my guest today, Alex Lieberman, is the co-founder and executive chairman of Morning Brew. He just sold a majority stake of it to Business Insider this year for reported $75 million.

• 2:59Ryan Holiday?

  It's a huge newsletter. He was an ad age 40 under 40, Forbes 30 under 30 recipient. He has a podcast for fidelity investments. He's talked all over the world. You can follow him on Twitter at Business Barista and of course, sign up for Morning Brew at morningbrew.com. It also happens that Alex is a student, a recent student of Stoicism. I saw him tweeting about it and we connected and we were gonna, you know, you meet people and they go, hey, you want to have a phone call? We should connect. And instead of doing a 20-minute perfunctory phone call, I thought, why don't we just record an episode of the podcast and we'll just talk about Stoicism? We'll talk about life. We'll talk about newsletters. And that's what we've got here in this conversation

• 3:42Ryan Holiday?

  with Alex Lieberman. I think you'll like it. And I was glad to get to know Alex through it. And enjoy this convo.

• 3:52Ryan Holiday?

  Let's start with your introduction to Stoicism because I'm always curious about how people heard about it and maybe what struck them about it.

• 4:00Speaker 01

  Yeah, so, you know, I've known about Stoicism, Stoicism for

• 4:08Speaker 01

  A fair bit of time, I want to say, I don't know, four or five years. And I think I actually first came across it when Tim Ferriss had referenced, you know, a Seneca quote or some quote on Twitter. And I had this perception, right? Like, we all create stories. I created the story of what Stoicism was without even knowing what it was. What was that story? Yeah, the story that I created was Stoicism sounds like it's a derivation of being stoic. And that is the exact opposite of what I'm trying to achieve because, you know, for context, I grew up like in a Wall Street family, not super, like, pretty unemotional.

• 4:53Speaker 01

  And for the longest time, I've actually wanted to do more to tap into my emotions and be an emotive person. And so I just created this very simple story in my head of like, I'm trying to be less stoic, not more stoic. Stoicism is based off of being stoic, therefore I'm not interested in Stoicism. And so that was my story for the longest time. And then what happened was I did this speaking engagement, I don't know, six months ago. And the guy who arranged it, as a thank you for, for me speaking, he sent me a book. And honestly, it was so nice. Like, I'm, I really am not sent books when I'm sent thank you things. And it was like, actually the coolest thing to just get a book in the mail, thanking me for my time.

• 5:38Speaker 01

  And what he basically said is, you know, I read this as I was trying to

• 5:46Speaker 01

  gain more clarity in my professional journey.

• 5:51Speaker 01

  And I really loved it, and I think you'll love it too. And so what the book was is it's this beginner's guide to Stoicism, Tools for Emotional Resilience and Positivity. And What's it called? It's called The Beginner's Guide to Stoicism, Tools for Emotional Resilience and Positivity by Matthew Van Natta. Okay. And it's like a little, it's like a little handbook sized thing and it Has like 150 pages. And so

• 6:19Ryan Holiday?

  Oh, I know this book. Yeah, he's he's sent me this before. Yeah, got it.

• 6:22Speaker 01

  Yeah, yeah. And so this was kind of like the re- reminder to me, the thing that that re-upped it. And I think the reason I actually started reading this was I was feeling particularly lost. I had been doing a lot of soul searching on kind of like how I want to spend my time. And this book was on my bookshelf and I picked it up one day and I read the description again, which was tools for emotional resilience and positivity. And I think I looked at that word positivity. And I was like, this isn't, this isn't, this breaks my story. This isn't part of my story of what being stoic is. So maybe there's a difference between stoicism and being stoic. And so I broke open the book. I went to the dog park with my dog Rambo for two or three hours.

• 7:07Speaker 01

  And I just read the whole thing.

• 7:09Ryan Holiday?

  Yeah, no, it's, it's funny. I think that's a, that's actually an interesting marketing thing you brought up, which is like, so sometimes people will question like certain decisions that I make in how I present work or videos I'll do or whatever. But that like, the idea that every customer or every person has a story, and that this story is often limiting in some way. And that when you present something or you put something out in the world, you're not just having to represent it as it is. But you're also having to anticipate potential objections that people might have. And

• 7:46Ryan Holiday?

  present yourself in a way that you either don't threaten, or you, you, you don't meet those, those reservations. Like, for instance, my, my book, The Obstacle is the Way deliberately says nothing about stoicism on the cover, because I found that stoicism, people have the exact impression that you said. And so if you, if you, if you put stoicism, let's say, in the title, although I obviously did this later with the Daily Stoke, but upfront, you are often limiting yourself. And so that's, that's a very interesting story.

• 8:20Speaker 01

  Well, and what I like about even, you know, I have Daily Stoke in front of me right now also. And it's like, At least for me, and I would assume there are a fair number of people like me because that what I ended up doing is after reading this book, I have a podcast of my own and I did one episode on basically my learnings about Stoicism from reading this book. And I had so many of my listeners who basically wrote back saying the same thing that they were like, oh, this is so interesting. I've heard of this, but I assumed it had to deal with being emotionless. So I never thought to dive deeper. And so, I mean, even in Daily Stoic, right? Like on the cover, you have the 366 Meditations on Wisdom, Perseverance,

• 9:02Speaker 01

  and the Art of Living. To me, that provides more flavor that potentially counteracts the narrative that I and many people have. But yeah, I think it's in a lot of ways, just like a branding question more than anything else.

• 9:17Ryan Holiday?

  Yeah, I mean, I think I say that in the intro of the Daily Stoic, that the phrase Stoic philosophy is like perhaps two of the least appealing words in the English language combined to make a super unappealing phrase. And so if you want to reach people, which obviously you want to do with a book, but you definitely want to do if you have something you believe in that you want people to, you want to reach people with, you have to find a way, if not to subvert it, then to anticipate and address. And you just don't want to be running into a headwind. You want to try to find a way always. Just like I'm sure with the Morning Brew, if you're like, like, there's something sort of light and nice about the

• 9:57Ryan Holiday?

  name that's not like, even though it's a serious email, it's, it's not, it doesn't, it's not like, oh, this is something you're gonna dread doing.

• 10:06Speaker 01

  Oh, totally. And by the way, that's like why we spend so much time in the early days especially, but even today on subject lines, right? Because like, it's, it's like the goal with writing as well, right? It's like, when you write a sentence, your goal is to get someone to read the next sentence. And it's like, you know, if your goal is to get someone to, to learn and benefit from the principles of Stoicism, it's to get someone to be willing to actually learn what those are. And like for Morning Brew, the number one thing that determined if people were going to read our whole newsletter is if the subject line was enticing enough to get them to open. And we would test our subject line, we still do it, where at five in the morning Eastern

• 10:47Speaker 01

  time, we send four batches of emails to a group of 10,000 people, and it's four different subject lines. We let those go out for an hour. And then at the end of the hour, at 6:00 AM, we see what the difference in all those subject line is in terms of open rate. And then we send the remaining, call it 3.4 million email addresses, the winning open rate, because that literally was the difference of, call it 50 to 100,000 more people reading it a day.

• 11:16Ryan Holiday?

  Right. So what do you think hit you about Stoicism, other than this idea that you're very, very repressed and now Stoicism is going to open you up? What do you think, what do you think hit you about the philosophy that, and maybe why it didn't hit you earlier?

• 11:32Speaker 01

  So here's my, here's my honest take on it, which is, you know, after, after we sold Morning Brew in late 2020, call it four months later, was when I moved out of the CEO role into the executive chairman role, which is the role I'm in now. So I'm not in the, the day to day of the business, and I'm spending more time creating content, working with my co-founder on like high level strategy. And I felt, I honestly, I felt directionless. And I felt like I was in this circular reference of a story that I had

• 12:14Speaker 01

  created. And I was basically trying to figure out, how do I get out of this circular reference? And kind of like the, the, what the story was, was, okay, we sold the company. I thought money was going to make a big difference to my happiness in life. It has not.

• 12:39Speaker 01

  It is not going to be a crutch anymore for like try, basically for doing things to get money, because money will give me happiness. You know, I've been given the freedom of time now, and I don't feel any better. This sucks. That was kind of like my circular reference. And, and at the same time as doing that, I had all these doubts that about like, what does the future hold for me? Like, I don't want to be the, the 28 year old who peaked at 28. I don't want to be the one trick pony. I don't know if I could build another business again. Did I get lucky? Like, this was the narrative I was telling myself, right? And it's so different from, I would say, people on the outside, they'd be like, oh, wow, you know,

• 13:22Speaker 01

  those guys from Morning Brew built this amazing media business. They bootstrapped it for five years. Like, they're incredibly talented. And that was totally not the story that I had. And, and so that's why I think I went on this exploration to Stoicism, because I was like, I was like, this sucks. And what I'm realizing is basically, we, we all have, from my perspective, two realities. We have the reality of what actually happens in the world, like objectively what occurs. And then we have our story and our perception of what occurs. And I, I'm, and I want to figure out how I can gain clarity around my story and my perception, and get myself out of this circular reference.

• 14:05Speaker 01

  And so, you know, reading about Stoicism, I think to me, actually, was, you know, I'd spent time studying mindfulness as well. And to me, Stoicism, I almost thought, was a great bridge of some of the things that I've learned in, call it, eight years of doing therapy. So like traditional, uh, Western, uh, psychological practice, that I would say is very much about like labeling, naming, and prescribing. And then mindfulness, which I would say can be very high level, ambiguous,

• 14:45Speaker 01

  up for interpretation. And for me, at least my, my, what I really loved about both your book and this original book I read, was it, it brought specificity to some of these higher level concepts, right? So like, the idea of

• 15:05Speaker 01

  Basically, like how focusing on controlling the things you can control and not focusing on not controlling the things you can't control, right? It's like, it's so obvious. And I think there's so much in, in both Eastern and Western that talks about this. But I just found it to be very approachable when reading Stoicism in a way that made sense to me and it was practical.

• 15:28Ryan Holiday?

  What did you, so I assume that, that the business was, was making a good chunk of money.

• 15:34Speaker 01

  Yep.

• 15:35Ryan Holiday?

  What did you think that suddenly tens of millions of dollars was going to change for you?

• 15:40Speaker 01

  I think part of it was that I, I had money anxiety in general, growing up in the sense of like, I was afraid to spend money, you know, especially after when, when I was a junior in college, my dad passed away and I kind of like, had made this promise to myself that I would be the person to bring in money for my family. And I had anxiety around like, the fact that everyone in the Lieberman household was cash outflow and there was no cash inflow. And, and so I think in my head, the story I told myself was that when I have some large

• 16:25Speaker 01

  windfall of money, that money anxiety will go away because I'll feel like I am able to provide for my family and provide for myself in a way that I will not have any sort of money insecurity or anxiety moving forward.

• 16:38Ryan Holiday?

  So you suddenly actually get like more money than, than a person could possibly need. What, what does that feel like? What, what actually does change? I'm always fascinated, I've not gotten a good self-aware answer from a single person from just sort of regular, successful entrepreneurs.

• 16:56Speaker 01

  Yeah.

• 16:57Ryan Holiday?

  Up to like legit billionaires. But I am curious, like, so suddenly, you know, there's nine or 10 figures in one's bank account. What, what changes?

• 17:07Speaker 01

  Yeah. Um, well, what I would say is.

• 17:15Speaker 01

  Not a whole lot. And I think that's also, that really is a function of values, right? In the sense that like, I just, I don't place a lot of value on buying very expensive things, right? Like, I was actually talking to my executive coach today, and he was like, "What, what do you want when you grow up?" And I was just like, "I want to have a, a family with three kids. I want to have two homes, one in like, the tri-state area, one in Colorado, would be awesome. I'd love to take great vacations with my family. Um, I'd love to, and I'd love to have new experiences with my family and friends. And in doing all

• 17:57Speaker 01

  that, I don't want to have any anxiety about money." That, that's kind of like, that's my image. And I think, part of the reason nothing changed, is, you know, I'm still 28, I still don't have a family yet. None of these massive purchases or things have come up yet. But, in the same sort of way, and I think it's what's making me realize a lot of this, like, moneying, securitying, and anxiety is, is irrational. I think I still have as much insecurity or anxiety about money today as I did before the transaction.

• 18:32Ryan Holiday?

  Wow.

• 18:34Speaker 01

  Which is such a fascinating thing.

• 18:36Ryan Holiday?

  Have you listened to Ramit Sethi's podcast?

• 18:39Speaker 01

  So, I've read some of Ramit's stuff. I haven't listened to the podcast.

• 18:42Ryan Holiday?

  Podcast is great. I know I'm using my podcast to rave about his. But, I was just listening to an episode the other day, where it was a, two, like, a couple, they work at tech companies, they've been successful, they have a net worth of $8 million, and they comparison shop for blueberries, right? Like, they're sort of stuck in this cycle. I think we all get, sort of get scripts, or ideas about money, or, uh, what it means, or what it will do for us. And then, whether you have $80,000, or $8 million, you're still trapped in that thing. It's a, I think you would really like it, but I'm, I'm a big fan of that podcast.

• 19:17Speaker 01

  Yeah, yeah. I'll, I'll listen to it. And, yeah, and I think what you said is like, I, I do think, in general, we get trapped in stories as well, right? Like, this story in my mind, was that, um, money equals success. The more that I have of it, the more successful that I am. Also, the more that I have of it, the less that I have any anxiety around it. Um,

• 19:40Speaker 01

  And I think it's it's one of those things where even even like rationally, where you know, you see those statistics about once someone is making a certain level of income. I can't remember. It depends where you are in the US.

• 19:53Ryan Holiday?

  It's like 70 grand.

• 19:54Speaker 01

  Exactly. Yeah, like, yeah, like 70 grand. Your marginal happiness per dollar you make goes down significantly. Like you hear that and you rationalize it. But at least for me, it was very hard for me to appreciate that until I lived it. And now that I've lived it, I'm just like, no, no dollar is going to change my marginal happiness. And so I really need to look inward to to gain a sense of clarity. And happiness, just through my perception of the world.

• 20:23Ryan Holiday?

  Well, this is really interesting, too, because and I think this is why the Stoics resonate with me more than some of the eastern philosophers is that, although there are certainly impoverished Stoics, Epictetus being one, you know, Marcus Aurelius is very wealthy. Seneca is very wealthy. Cato is very wealthy.

• 20:42Ryan Holiday?

  Zeno comes from wealth, loses it, and then seems to get a chunk of it back. The idea being that they were like real human beings in the real world, who were probably all primed, like we all are, to think that more is better and that you will be happy when you have more. But then they but then, unlike a lot of philosophers, they actually got more, right? So it's like very easy to go like, more will be better or to say more doesn't mean anything. But like, it matters if you actually have tested the hypothesis in the real world, not just in the classroom. And you get you get Seneca basically saying like, look, it's better to be rich than poor in the sense that it's probably better to be tall than short, beautiful than ugly, or to have two arms versus one arm.

• 21:28Ryan Holiday?

  If you had your preference, that's what you would do. But you are also at a place where you don't need it either way. So like when the Stoics talk about indifference, we tend to think indifference means you don't like it, which is obviously the definition of what indifference does not mean. For the Stoics, indifference was like good one way or the other.

• 21:48Speaker 01

  Totally. Yeah, I think I think it totally makes sense. And, you know, as I was reading.

• 21:57Speaker 01

  Both books and, and I think about this general, generally as like, I'm kind of practicing, call it like my inner work is so much of what I'm trying to do is just like unlearn the expectations, anxieties and like regrets that the world has taught to me and not necessarily intentionally. Um, but like in so many ways, when I feel like I'm, I'm, you know, practicing, whatever it may be like controlling things I can control or living in the present or, um, you know, um, separating like my reactions to kind of my final judgments. Like, I don't know, in a lot of ways, I feel like I'm just trying to live like a child again.

• 22:41Ryan Holiday?

  What does that mean?

• 22:43Speaker 01

  Like, uh, in so many ways, when I think about what, when Alex Lieberman was in kindergarten, I would say like Alex Lieberman was his happiest self. Like I, I loved learning in my kindergarten classroom with Miss Golo. I was super creative. I remember in kindergarten, like I, I felt like I was the smartest person on planet earth because I took a pen and a highlighter. I cut them each in half. I taped them together and I was like, I'm a fricking genius. I just made a pen highlighter two in one. And like I'd go on the playground, I'd play with kids, I'd laugh a ton. I wouldn't be think, I, I wouldn't be thinking about

• 23:26Speaker 01

  like, oh, yesterday, um, when Sally said something mean to me in kindergarten class, I still really am dwelling on that. Or I wouldn't say to myself, oh shit, like, am I going to do well in kindergarten, uh, in terms of my final grade at the end of this year? Like those were never thoughts. Right? And, and so obviously it's not realistic because we live in a society where expectations, progress, like it is both measured and it's how society is structured. Well, like, there's so many things I admire about the way I was able to live when I was in kindergarten.

• 24:04Ryan Holiday?

  Well, yeah, I think, I think there's a certain presentness to children and openness to children and acceptance to children, even though they throw tantrums about things. They're just sort of like, they're sort of, I think, aware of how little control they have. So there's like, oh, this is where we're going. Okay, you know, and, and there is a, I think, what comes from that are some things you don't necessarily think about as Stoic, but like, sort of joy.

• 24:31Speaker 01

  Yeah.

• 24:31Ryan Holiday?

  You know, it, it is a more, you know, the Stoics talk about living in accordance with nature, and I think children are more in that state, the, the, the connection to the sort of world. Whereas like, we live in this place where we think we're in control, we have things we're trying to do. We have what, what the Buddhists call willful will, and I think that is at the root of a lot of our unhappiness.

• 24:56Speaker 01

  Yeah, no, a hundred percent. And, and it's even like, I don't know, I was just thinking about how one of the things that really stuck with me in terms of like,

• 25:09Speaker 01

  desiring and focusing on the things that are within our complete control, right? It's, it's such a obvious point when you say it out loud, like, oh yeah, obviously, I'm only going to focus on the things I can control. But then when you actually reflect on the things that drove your emotions in the last 24 hours, how many of those things were based on what you could control?

• 25:31Ryan Holiday?

  Most of what you spend your time on is stuff that's not in your control. Like, it's, it's just like, oh yeah, let's focus on what we control, that's really obvious. And then it's like, okay, but what did I spend the majority of my time, energy and emotional energy on in the last 24 hours? It was the opposite of things that are in my control.

• 25:50Speaker 01

  Yeah, and I would say for me, like, the vast majority of it is like anticipatory anxiety, where it's like, when I would be managing people within Morning Brew, and I would need to, say hypothetically, tell them that they're not doing what's expected of them in work. Especially in the early days when I was a first time manager, I would default to not saying the thing because I'd be so concerned about how they would react. But like, that's, that's kind of like not my thing to own. My thing to own is, how can I deliver this in a way that is clear and empathetic and compassionate? But I can't worry about how someone is going to respond to that if it's going to impact my ability to do what I think is most important and is within my control. And like, I feel like that is the story of 90% of managers.

• 26:34Ryan Holiday?

  Yeah, I think that's right. Well, and I think the idea, to me, where Stoicism really fits well in the idea of, of management, and you know, the Stoics were managers, back to Marcus Aurelius, he's the manager of the largest empire in the world, is like, you wake up and shit goes wrong. That is like, that is the entrepreneur's life, is it's never going the way you want it to go, and you're forced to improvise, adapt, accept, you know, change around what's happening in the world and what's happening with your people. Because that, that's, I think, the tricky part about running a company is that it is

• 27:18Ryan Holiday?

  dependent on a bunch of people who you do not control. Even though you're their boss, you do not control them, you don't control what they think, you don't control what they, you know, how quickly they do. It's this thing that you're only nominally the head of, and you have to figure out how to make it work, however imperfect it is.

• 27:39Speaker 01

  I have, I'm not sure if you know the, the answer to this, but like, something I've thought about, you know, how kind of the Stoics would, would think about this is, like you just mentioned, like shit hits the fan in work all the time, and I think, Actually, my, my thing that happened that was very adaptive and it served me well, but I think there's trade off to it is I learned how to become kind of like numb to shit hitting the fan in work, meaning something would go horribly wrong and I'd always be like, oh, it's fine. We're, we're gonna figure it out. Like that would be kind of my default is I would

• 28:20Speaker 01

  literally not experience the experience because I needed to stay level headed and fully objective. But I think there's a trade off to not fully feeling your emotions or experiencing that emotion in a way that is productive. Do the Stokes say anything about like, how do, I guess, feel or experience your emotion, but do so in a productive way where it doesn't hold you back?

• 28:42Ryan Holiday?

  Well, I think so two things. So one, yeah, that is obviously the job of the leader because if shit hits the fan and then the leader freaks out, like where does that leave everyone else? Right? Like it, it's sort of like if the parents are handling it badly, then the kid either is in real bad shape or the kid has to then go do the adult job, which isn't fair. Right? Um, so I think that there is a higher standard for the leader and Seneca talks about this in his essay on anger. He's like, look, normal people in smaller positions can be angry, have feuds, get worked up about stuff, et cetera. But you, the emperor, he's writing mostly to Nero, it seems like you can't, you can't, it's too expensive for you, right? Like too much is

• 29:25Ryan Holiday?

  dependent on. So you have to sort of be more controlled than the average person. But Seneca also talks about sort of generally with emotions, this idea that like there is the immediate reaction, uh, fantasia, uh, the, that you feel like if somebody jumps around a corner and scares you, um, you can feel that. It's just what do you do in reaction to it after? So, right? To again, to go to the idea of, of anger, like if someone says something hurtful or some employee really screws something up, like you could be upset. This thing just cost you, you know, um, a million dollars, but the decision to call them into your office and chew them out about it

• 30:09Ryan Holiday?

  or abuse them about it, that is where the line is, right? So it's like you can have the emotion, you just have to understand that as the leader. You are circumscribed in your ability to act on that emotion and that this is probably a good thing, right? Like, the idea is to process that emotion, figure it out, instead of just dumping it on someone, which I'm very guilty of myself. So I'm not trying to say this from some place of sageness.

• 30:38Speaker 01

  Totally. And I think, again, the way you put it makes total sense, right? Like, you can kind of, you can have both, but you just can't have one impact the other in a way that holds back your ability to run a business or any relationship with clarity of thought. I will say, at least from my own experience, I found it very difficult at times to create that delineation where it gets blurred. And I think out of fear that I will act emotionally, I end up acting, I would say, more like a robot than someone who's overly emotional.

• 31:12Ryan Holiday?

  Well, this is something that I benefited from in mindfulness and in meditation. The idea of like, you're having, like, so you're sitting there and you're trying to have no thoughts, right? And so the mind's like, here's a thought, here's a thought, here's a thought, right? There's sort of witnessing that this is what your mind does. And then what they teach in mindfulness is the idea of going like, yes, you're having the thought, but you don't have to accept the thought, right? Like, the idea of seeing thoughts as sort of clouds in the sky, they're there, you acknowledge them, but you don't try to grab hold of them. You just sort of let them come in and out of the frame. And like, this is something I've been dealing with, with just like, how screwed up the world is right

• 31:54Ryan Holiday?

  now. It's like, this, you know, it looks like the Supreme Court's gonna do this, and it looks like they're gonna do this, and it looks like this is the latest on this variant, or, you know, here's some awful trend that's sort of looming in the background that you're powerless to do anything about. I'm trying to remind myself, like, you can have that feeling, like, that is scary, it's weird, it's disappointing, it's not what I would choose if I had a choice. And then I can just sort of sigh and then get back to what I should be doing, right? Like, you don't, you don't have to be anguished about it, you don't have to be consumed by it, you don't have to pretend it's not there, but you also don't have to give yourself over to it.

• 32:40Speaker 01

  Totally. Well, I mean, like, even, it's kind of the same exact thought on, call it like, the Western side with a lot of the work I do with my therapist, it's around, you know, I suffer from OCD, it's manifested in many, in different ways over, call it like, the last decade of my life, and there are different ways that you can work through or work with OCD. One way is exposure therapy, the other way is ACT, acceptance and commitment therapy, and it's basically, in my mind, acceptance and commitment therapy is kind of a prescribed or labeled version of meditating or practicing mindfulness in the sense that

• 33:20Speaker 01

  you acknowledge that a feeling is there, but you don't extrapolate it to your entire experience. You know, the way that my therapist has always kind of like, explained it, similar to like, the cloud analogy, or like, the meditation analogy of like, a moving river, with things moving through the river, is, it's like if, if you have like, one of those little swimmers in your eye, and the swimmer is like, in the top-left corner, it is there, it is annoying, it is inhibiting your vision a little bit, but it's not blinding you, it is not blocking your entire vantage point, it's just there, and it's annoying, and that's okay.

• 34:00Ryan Holiday?

  Yeah, I think that's right. I think that's right. It's obviously easy to sort of agree in, in theory, and then, of course, when it's more than just a swimmer in your eye, and it feels really scary, or weird, or upsetting, then it's sort of like, you know, getting yourself under control when you, when you relapse.

• 34:19Speaker 01

  Totally. And by the way, like, I think, in, without getting too much into kind of like, the, the deep discussion about it, like, I, I think we've kind of just seen that on like, the world stage with all the, the conversation around.

• 34:36Speaker 01

  Around the virus and the vaccines is like, kind of, all these different viewpoints on what is the right procedure to stay healthy and safe. Where there's so much information. There's information overload, but there are also a lot of questions that aren't exactly answered yet, right? Even with the new variant, it hasn't exactly been answered yet. You know, how virulent is it? How easily spreadable is it? And I think when there's ambiguity, when people's health is at risk, things get very emotional. And I think it also, it creates a great opportunity for like the separation of emotional and like, logical discussion. It creates a great opportunity for that to happen.

• 35:19Speaker 01

  But kind of to your point, when this is like a very real concern that hundreds of millions of people are experiencing, sometimes it's way easier said than done.

• 35:29Ryan Holiday?

  Yeah, and I don't know when people will be listening to it, but it's a great example, right? So as you and I are talking, we're like three days into the acknowledgement or the, the recognition of the, of the, the new variant, which has a stupid name. Yeah. A great, a great illustration of the failures of communication of the various agencies in the world that they would pick. A long ass variant name that is not clear how to pronounce. Why wouldn't they just call it Omni, right? Or Omni, or any, like, who cares about whether it normally is connected to this alphabet or that?

• 36:04Speaker 01

  Couldn't be easy.

• 36:05Ryan Holiday?

  Yes, I digress. What I think is interesting is they're like, look, this is it. We know that it exists. We don't know, we know that obviously it'd be better if it didn't exist, but we don't actually know the implications of it. And we won't know for approximately two weeks. So everyone's going to have to sit in a period of unknowing, right? Which is about the hardest thing you can possibly ask of people. And you've watched even the last three or four days, people trying to, it's not that they want a shortcut, but they're just like, I know you said two weeks, but could this be the answer? Could this be evident? And so instead of just like, like I was saying, going like, hey, this is there and you're going to have to. The next two weeks of your life with this sort of looming uncertainty,

• 36:50Ryan Holiday?

  people are like, well, what if I doom scroll all day? Will that make the answer come sooner? Or, you know, what if I just freak out? Or what if I start blaming fingers? Or what if I go into denial about it? And it's like, none of those change the fact that you have to sit uncomfortably with this thing for two weeks. And, and by the time people are listening to this, it could be the worst case scenario. It could be the best case scenario, having revealed itself. But nothing that happened in this period will have changed that or made one or the other more or less likely. And people just really struggle. Marcus Rilke in Meditations talks about having no opinion. He says, you always have the power of having no opinion. But that's a power we relinquish, you know, pretty much all the time.

• 37:35Speaker 01

  Yeah, a hundred percent. It's, again, it goes back to control. There's nothing we can do to control the situation. But yeah, ambiguity is, again, like, I, I have personally struggled with ambiguity for my whole life. And I'm just seeing people who I haven't seen struggle with it in the same way that I have for so long, struggle with it as a function of what's going on in the world right now. And it's, like you said, it's, it is really difficult. And well, we don't know what's going to happen. But also it's not within our control to dictate what's going to happen.

• 38:08Ryan Holiday?

  The other thing that I, to me, that connects to us in the pandemic the best, and it's a quote, again, easier said than done, but one of my favorite passages in Meditations, Marcus Rilke goes, look, is a world without shameless people possible? And he goes, no, of course not. He says, a certain percentage of the people are going to be shameless. So when you meet a shameless person, like, why are you surprised first? But second, like, know that this is one of that percentage, right? If it's one out of a hundred, you met one. Okay, that's one out of a hundred. They, you knew they existed. And I think, and I've struggled with this myself, like, there was never a possibility where a hundred percent of the people were going to take the pandemic seriously, where a hundred percent of the people were going to get vaccinated,

• 38:54Ryan Holiday?

  where a hundred percent of the people were going to do any of these things. And yet, we are dismayed every time we meet one of those people. Now, obviously, there's a difference between 30% of the population and 10%. And there is a certain amount of that that's in the control, if not of us, than of like sort of policy and public culture and how one handles things. You can influence that number. But the idea that you're, this was, you were ever going to get everyone on board, was naive and impossible. And so I do take some solace in the like, look, certain percentage of the population is going to be selfish and stupid. Certain percentage of the population is going to be misinformed.

• 39:37Ryan Holiday?

  Certain percentage of the population is going to be misled and used against their own interests, et cetera. So you've just got to accept that when you meet one of those people.

• 39:50Speaker 01

  Totally. Yeah. I, I think it's so well said. And honestly, like what, what a lot of this just has me thinking about. And I've been thinking about this a lot recently as I think about kind of like my journey and, and also as just I've consumed your content is just like, just think about how much, just how many more tools you have personally, given all of like the study you've done in Stoicism, just to navigate life and everything it has to offer. And I've done one, one thousandth of your study, but I have found even tools already. And I don't know, I've just thought to myself recently, like how amazing of a world it would be when people have these new tools through inner work.

• 40:32Speaker 01

  And obviously it feels like things like meditation and mindfulness are so much more prevalent today than even say in my parents' generation. But it still feels so incredibly early. And obviously, as someone who's grown up in media for the last six years and just like the power of building a trusted audience and delivering a message that can have an impact, I have just thought to myself, there's like, I think there's such a white space for I don't know, like whether it's making Stoicism go viral, making mindfulness, making inner work go viral in the sense of like making it approachable to people where it becomes a daily practice at a mass scale. And obviously, I'm assuming that was one of your goals with, you know, things like daily Stoic.

• 41:12Ryan Holiday?

  Yeah, of course, of course. The idea of like, how do you, how do you take these ideas that are simple, but perhaps inaccessible at the beginning and bring them to people? Just like, yeah, there's really nothing in Morning Brew that people couldn't find elsewhere. But the point is, the value proposition is like, now you don't have to find it elsewhere. Like, the point is in the aggregation, right? Or in the collection, or in the lens, or the angle. And, you know, sometimes people will say this, like, they'll be like, oh, why are you reading Ryan's stuff? You should just read the originals. And it's like, literally, nothing would make me happier.

• 41:55Ryan Holiday?

  But that wasn't exactly happening at any, you know, significant number until I started doing this, right? Or it was very unlikely, not to take credit for it then, but there was also very unlikely that this chunk of the population that I'm speaking to would have been doing that. Now they are. And so it's funny how people can get sort of really snooty about stuff when, when actually it is bringing about exactly the thing they claim to want to happen.

• 42:28Speaker 01

  Yeah, I mean, I think about content in three ways. I think about it as original creation, curation, and in that bucket, I put curation and remixing, and then translation. And I think we put so much emphasis in society on creation that like, oh, I need to be a creator. I need to put stuff out. It needs to be my own original thoughts. I need to be the first person that thought of this. Like, you know, the newsflash is that like, pretty much everything that all of us are thinking of is not an original thought. And that's, that's okay. That's not a bad thing. There have been a lot of people on planet Earth that have had Had similar brains to ours. But I think so much of the value, especially in the fire hose

• 43:12Speaker 01

  that the internet has afforded us today, is in curation, remixing, and translation. And that's basically exactly what you've described in the same way like with Thinking Like a Monk by Jay Shetty. Like, I think it did the same thing because I tried reading some Buddhist texts, and I couldn't get through it. And I think also that the hard thing here, the harder thing, which I'm interested how you think about is like with Morning Brew,

• 43:41Speaker 01

  the reason we thought it would stick is because our view is like, a 26-year-old professional wants to look good in front of their boss. And to do that, they need to know what's going on in the world. But they don't have a lot of time to do that. So like, Morning Brew is like stupidity insurance, so you don't look bad in front of your boss. And so, like, every product I think about, I think about how is it a painkiller, or how is it a vitamin? And the issue is, is I think some of the most helpful products in the world are vitamins, but people gravitate towards painkillers, things that alleviate pain today.

• 44:19Ryan Holiday?

  Sure.

• 44:19Speaker 01

  And so, I, you know, in some ways, like, I think about Stoicism and mindfulness, and even personal finance in this bucket of vitamins. And the question is, is how do you create urgency for people to engage in vitamins when the long-term benefit is one that compounds on itself, and you don't necessarily see today?

• 44:39Ryan Holiday?

  Well, I went through this with the trilogy that I did on Stoicism, Obstacles Away, Ego's the Enemy, and Stillness is the Key. It was realizing, especially with the first book, it was like, I wanted to write a book about Stoic philosophy, but I knew that the vast majority of people were not interested in Stoic philosophy. But- Most people have problems, right? Most obstacles are a universal fact of life. And so the idea is, oh, okay, let me present a part of Stoic philosophy as a tool for dealing with obstacles or a solution to your problem. So it was like, very few people, and I remember saying this to the publisher, very few people wake up in the morning and say, I want to know about Stoic philosophy.

• 45:22Ryan Holiday?

  They do say, I have a problem and I need a solution. And so if you can meet people where they are, you can present. So vitamin is effectively preventative, right? And I think that's, people are bad at sort of prevention. But if you say, actually, this vitamin is a painkiller, right? Then, then you.

• 45:45Speaker 01

  Yeah, it becomes alleviation.

• 45:46Ryan Holiday?

  Exactly. And so that, it's like, I want to get you there when you're like, whether it's an athlete who just blew out their knee, or it's somebody who just went through a divorce, or, you know, blah, blah, blah. I want to get you there. And then you go, oh, this actually is a framework worth exploring more fully and can be applied outside the narrow context in which I was originally envisioning it.

• 46:09Speaker 01

  Yeah, I think that makes total sense.

• 46:11Ryan Holiday?

  You seem like you spend a lot of time on Twitter. I was curious about this sort of fire hose. I have, obviously, I have a Twitter account and we use one for, for my account. So, but I just find that I'm never, I never feel better after I've been on Twitter.

• 46:26Speaker 01

  Oh, I've spent, I've spent a lot of time thinking about this and like, because, so I, I would say, I got introduced to Twitter, call it two years ago by.

• 46:38Ryan Holiday?

  That's it?

• 46:39Speaker 01

  Yeah, by my co-founder. Like, like I knew what it was, but I didn't, I didn't really spend time on Twitter. And I, I would say I sometimes feel really good on Twitter. And I sometimes feel really shitty on Twitter. And, and the reason, I would say the reason I feel shitty is actually not the reason that a lot of people feel shitty. I feel like a lot of people feel shitty because they doom scroll on Twitter. They see sad things happening in the world. They see really polarizing conversations and they're like, what's the world come to? For me personally, that's, that's not what makes me feel shitty. What makes me feel.

• 47:22Speaker 01

  Shitty is, is honestly that it is an addictive platform. It is addictive, just like any other social media. I think, one, I procrastinate too much as a function of Twitter. And then I feel shitty because I've effectively not kept my promise to myself of not going on Twitter and doing the thing that I said I was gonna do. And then I feel really bad because if I can't keep my word to myself, who am I gonna keep my word to? And I think the second reason I end up not feeling great on it at times is because I feel that gravitational pull to look at the likes I'm getting and the retweets. And that is the exact, call it like, trigger for enjoyment that I don't want to be perpetuating.

• 48:07Speaker 01

  Right? Like, I was even thinking the other day, I would love to create kind of like a tool or a Chrome add-in where I could publish my tweets, but it never shows likes or retweets or comments going up. All I can look at is the content that I've put out, and that's it. And I have to just have a love for the information that I've put out.

• 48:29Ryan Holiday?

  But you can do, I mean, that's how I sort of do it, which is that I write all the things that I post. But then, one, it goes to someone on my team. But even then, it just gets scheduled, right? So like, I don't interact. It's a, it's a one-way medium, unfortunately. I wish it could be otherwise, but for me, it's a one-way medium.

• 48:48Speaker 01

  And I think that is the healthier way. The only thing that I find that that, that you could possibly miss out on as a function of making it one-way is called like, the amazing conversations and connections that happen in DMs on Twitter. So like, just some amazing people that I've met, like, I wouldn't have connected with you.

• 49:12Ryan Holiday?

  The checkmark, you get, it's like, it's like this weird, like, side door loophole to connect with people. You could never, you would never be in the same room with, you'd never have their phone number.

• 49:25Speaker 01

  Exactly.

• 49:25Ryan Holiday?

  It's weird.

• 49:26Speaker 01

  And so a lot of people that I now actively text with every day, just talking about interesting topics, some related to work, some related to web 3.0 and NFTs, some not related to work at all, and just like kind of the journey that I just discussed, those happened through originally DMs on Twitter, and those happened on DMs on Twitter as a function of them seeing my content on Twitter.

• 49:50Ryan Holiday?

  I think that's how we got connected. You tweeted something about Stoicism, but then somebody sent it to me because they knew I wouldn't see it. And then I DM'd you and here we are.

• 50:00Speaker 01

  Exactly. So we wouldn't have gotten connected otherwise. Or if we would, maybe we would have, it just would have happened at a different time. And so that's the hard thing for me is if I, I think if I treated Twitter in the same way you treat it, there'd be so much benefit. I wouldn't feel really crappy about the validation and happiness I feel from likes and the dopamine hits. And I wouldn't feel like I'm not keeping my word to myself, but I would feel like I've deprived myself of a form of community building and connection. And maybe one could argue you could accomplish that elsewhere. But I just haven't figured out a great alternative yet.

• 50:35Ryan Holiday?

  No, I get it too. I find Instagram seems to be a platform that you get most of the benefits, less of the

• 50:45Speaker 01

  That's interesting.

• 50:46Ryan Holiday?

  The aftertaste. And you still get the same sort of DM benefit, I guess, but

• 50:52Speaker 01

  Yeah, I just, I just got to, I just got to build a bigger audience on Instagram then, I guess, because I'm not getting access to, to cool people to DM with.

• 51:00Ryan Holiday?

  I just find Twitter is sort of radicalized, like otherwise thoughtful people. And so it's, it's just, it's like Twitter is overtly political, whereas like Instagram, the other networks have a political component, but it hasn't, the, the, the, the tail isn't wagging the dog. And so, like, I remember in the early days of Twitter, I was actually in Austin in 2007 at South by Southwest when Twitter launched. I remember I was with Tim Ferriss and Tim was like, I was like, this is the dumbest idea I've ever heard. And Tim invested in it. So I guess that, that shows the difference between us, but

• 51:40Ryan Holiday?

  I remember like people used to talk about pizza on Twitter and there was jokes and it would like Twitter wasn't the sort of toxic cesspool that it's become. And I think there is a part of these networks where you sort of like you get something out of them and then the ratio twists and you gotta, you gotta be able to be like, yeah, I'm getting off this.

• 52:01Speaker 01

  Totally. And by the way, the last thing that I didn't mention that I find to be particularly unhealthy about Twitter for me is again, all of us in life do some level of social comparison. And, and I'm constantly thinking about how can I build more internal sense of self so that kind of like that voice can be quieted a little bit. But I find that it is definitely activated in a very real way on Twitter. And I think that's a function of the crowd that hangs out on Twitter. Because Twitter is so like, has such a concentration of like venture capitalists, venture backed startups and other founders. Honestly, there's, there's a feeling of like

• 52:47Speaker 01

  lack of success that I feel where I see some of these people that I can get, it's almost like it's the, the double edged sword to amazing access. It's like I get incredible access to unbelievable founders and VCs. But on the other side, I'm like, shit, I've only built one business and I'm talking to these people that have built four billion dollar companies. Like what am I doing with my life? And I think that's a really unhealthy thing that I find as well.

• 53:09Ryan Holiday?

  Yeah, no, it sounds like, I think I'm very suspicious of things that are motivated by FOMO. And so like you're saying like, well, what would I miss if I wasn't on it? I'm like, okay, that's like a good thing to not do.

• 53:22Speaker 01

  Yeah, yeah. No, no, I think, I think it's really interesting. And I think almost like another way to frame this is like, how could I find great connection and community without the trade off of my mental health?

• 53:38Ryan Holiday?

  Totally, totally. Well, let me ask you then, other than morning brew, what does, because this is another, I think, source of misery and, and

• 53:49Ryan Holiday?

  Just disorientation for people is what does your media diet look like? As someone who sort of does this professionally, but also probably has peered behind the curtain a little bit, what does your media diet look like?

• 54:05Speaker 01

  I would say the vast majority of what I consume is bookmarks that I have bookmarked on Twitter. It is.

• 54:20Ryan Holiday?

  What does that mean?

• 54:22Speaker 01

  So, so as in like I have, you know, my cure, like I have the people that I follow on Twitter.

• 54:27Ryan Holiday?

  Twitter is like your newspaper.

• 54:29Speaker 01

  Yeah, exactly. And when I see interesting stuff that I follow, I'll bookmark it. And now you can have folders in your bookmarks. So I have one folder for entrepreneurship, one folder for mindfulness and spirituality. And I, every day when I dedicate time to consumption, I go to those folders and I go through the content. And, and, you know, typically like tweet threads have become a big thing, right? Like a string of tweets, that'll be a lot of times stuff that I'm bookmarking. So that's one. The second would be just like close connections, friends, contacts that I'm like texting with, just sharing articles and things for me to read. So referrals. And then the final one, honestly, I read so a bunch of essays.

• 55:14Speaker 01

  Like I actually don't like reading. This, this sounds so ironic because it is. I don't read that much news.

• 55:21Ryan Holiday?

  Yeah.

• 55:22Speaker 01

  Like I read the brew every day. I read maybe one or two other newsletters, but for the most part, I would say 95% of my media diet is ever gray or evergreen, things that were written a while ago or have a longer shelf right life. And a site I always go to, to read essays is, it's called readsomethinggreat.com.

• 55:44Ryan Holiday?

  Oh, I've never heard of this.

• 55:45Speaker 01

  And it's amazing. It's basically, it's a website that has manually curated essays. And it offers you five at a time. And it's always the same categories. The first category is living better. The second category is business and tech. The third category is history and culture. The fourth is science and nature, and the fifth is wildcard. And basically, it's essays that have been vetted by the person who created this site. They, you know, they range from being a two-minute read to a two-hour read. And I just find amazing content here. And what I love about this is it helps me with discovery of great writers.

• 56:27Speaker 01

  And then, once I find a great writer, I'll go down the writer rabbit hole, and I'll just read everything by them. And that actually leads me to another site, which is called alias.co. And honestly, you may even be on alias.co. Let me see.

• 56:41Ryan Holiday?

  I've never heard of it.

• 56:43Speaker 01

  Oh, no, you're not on it yet. Basically, it's a site that allows you to go down the rabbit hole of people. So you go into alias.co, and it has a whole directory of people. So for example, right now, I'm looking at Balaji. I'm looking at Paul Graham. I'm looking at Reshma Sajani, the founder of Girls Who Code. And it has every podcast, YouTube video, tweet, and essay that they have ever appeared on or written. And so it's like, if you want to study the mind of a person, it is the place to study the mind of people that have been curated.

• 57:22Ryan Holiday?

  Interesting. Yeah, this is cool. So wait, so you have to join Alias? Or they decide who is featured on Alias?

• 57:31Speaker 01

  They decide who's featured. So I think, I think as they're spending time on it, like if you go to the search bar, right? You can look up your name, and you'll see it says notify me. I think they basically say, once a certain person has had notify me clicked a lot of times, it's their signal to curate that person's content. And so I think right now, you know, they probably have 50 people on here. And I think their goal is just to expand it over time. But to me, it's like the combination of read something great, reveals really interesting people who think in a new way that gets me to think differently. And then if these people are on alias, I'll go down the rabbit hole of everything they've created on alias.

• 58:11Ryan Holiday?

  Right now, this is interesting. I like, I like read something great. This is cool, too. I do like, I do like sort of people who write long form stuff. That's kind of why I like podcasts, too. Like, the idea of, of a sort of medium that's not dependent on virality. It's just dependent on sort of.

• 58:31Speaker 01

  Quality.

• 58:32Ryan Holiday?

  Yeah, or, but also, it's just like, it's in depth. And the fact that.

• 58:37Speaker 01

  Exactly.

• 58:38Ryan Holiday?

  Yeah, it tends to create better stuff.

• 58:40Speaker 01

  And by the way, this is like, one of my whole thoughts of, it's such an interesting thing, that like, other than for commoditized content, I rarely use Google anymore. And so like, the best content on the internet sits in like, the nooks and crannies of the internet, usually through referral or curation. And it's just so interesting that like, I have to do all these steps to find the most interesting stuff, because it's never going to be the stuff that shows up on Google.

• 59:08Ryan Holiday?

  Right. Yeah, yeah. It's, it's funny, because these two sites you mentioned are like, the opposite of Twitter.

• 59:16Speaker 01

  Exactly. Maybe, maybe I should just spend more time on these sites, unless on Twitter.

• 59:21Ryan Holiday?

  I think so. I think so. No, that's fascinating. What newsletters do you like?

• 59:27Speaker 01

  So, obviously, Morning Brew. I like James Clear's newsletter, 321. I like Not Boring. So, Paddy McCormick's newsletter. He just, he analyzes basically tech trends and up and coming startups. I love Ben Thompson. I just think he's like, one of the smartest thinkers about technology companies. Honestly, I'm looking for more in my newsletter diet that isn't, doesn't have to do with business, that either has to do with, again, like, psychology, mindfulness.

• 1:00:08Speaker 01

  Mental health, et cetera. So if you have any recommendations, I'm interested in those, but those are my top few.

• 1:00:14Ryan Holiday?

  Well, I may recommend the Daily Stoic email, which goes out every morning and it's one thought about Stoicism.

• 1:00:21Speaker 01

  I'm signing up for now.

• 1:00:23Ryan Holiday?

  What do I like that's not? I like, do you like Maria Popova? She does brain pickings.

• 1:00:29Speaker 01

  I've heard of it. I haven't read it.

• 1:00:32Ryan Holiday?

  I think you'd like that one.

• 1:00:34Speaker 01

  Okay.

• 1:00:34Ryan Holiday?

  I like, this one's more business, but Matt Levine's newsletter.

• 1:00:38Speaker 01

  He's great.

• 1:00:38Ryan Holiday?

  Ah, dude, he's, because even though like, it would seem very Wall Street-y, but it's, it's actually.

• 1:00:47Speaker 01

  He's just, he's hilarious.

• 1:00:48Ryan Holiday?

  Yes.

• 1:00:48Speaker 01

  He's hilarious. He has a great sense of humor. I've always thought to myself, if he went off, like away from Bloomberg and onto like Substack's platform, he would be the number one supported writer on Substack.

• 1:01:02Ryan Holiday?

  Yeah, probably because you could charge like $500 a year for it.

• 1:01:05Speaker 01

  Exactly. Yes.

• 1:01:06Ryan Holiday?

  Exactly. No, his is great. I like, I like Emily Oster. I mean, this is more of a parenting thing, but Emily Osters is fantastic. It's a parenting one.

• 1:01:20Ryan Holiday?

  Who else do I like?

• 1:01:21Speaker 01

  I'm not, I'm not a parent yet, so I may have to bookmark this for when I end up becoming a parent.

• 1:01:26Ryan Holiday?

  I do a parenting email each day, each morning too, called Daily Dad. Those are like my, those are the two that I write. But yeah, I do, I think it's a good point. I wish there was more non-political, non-business sort of daily or weekly or whatever, just sort of thoughts about life or psychology or trends or business or whatever.

• 1:01:54Speaker 01

  Yeah. I mean, I've been thinking there, there could be a cool, I have a few newsletter ideas that I haven't started, but I think would be amazing. One being like just a positive email, like literally just like, like, like three things that make you smile to start your day, like a quote, a picture, a video that just get your day going with momentum and realize how, and allow you to practice gratitude through example.

• 1:02:23Ryan Holiday?

  I think that's right. I liked, I liked Tim's Five Bullet Friday. I think that's,

• 1:02:27Speaker 01

  Yep.

• 1:02:27Ryan Holiday?

  That's, I get a lot out of that one. And then actually, uh, one of my, uh, one of my, he started as my research assistant and now he, he does content for Daily Stoic, but he has one called Six at Six, uh, where it's like six things every Sunday. Um,

• 1:02:42Speaker 01

  I like that.

• 1:02:43Ryan Holiday?

  And I, I like that one a lot. Um,

• 1:02:46Speaker 01

  Where do I find that?

• 1:02:47Ryan Holiday?

  Uh, let me see, let me see how, I don't remember, just, uh, let me get the name. Um,

• 1:02:53Speaker 01

  Okay.

• 1:02:54Ryan Holiday?

  Here.

• 1:02:54Speaker 01

  You can let me know later if you want.

• 1:02:55Ryan Holiday?

  Just, it's BillyOppenheimer.com. It's called Six at Six.

• 1:02:59Speaker 01

  Okay.

• 1:03:00Ryan Holiday?

  Uh, for everyone who wants to sign up. But no, I, I think, uh, I guess what we're, what we're hopefully kicking around as we wrap up is that there's a business opportunity and a market opportunity here for people who can create content that does not make people angry at the world when they're doing it, but it, it generally improves their life.

• 1:03:20Speaker 01

  Yeah, I was gonna say.

• 1:03:21Ryan Holiday?

  Something to think about.

• 1:03:21Speaker 01

  Content that invests in yourself and it doesn't have to be investing in yourself at work. Like,

• 1:03:28Ryan Holiday?

  Yes.

• 1:03:28Speaker 01

  I, I, I just, um, because I was feeling that need also, I just started a, a book club, uh, with, with founders. Um, but the whole, like, my whole thing was you're signing up for this if you don't want to read business books. Where like, we can, we can have discussion or we're gonna have a book club, but it's not gonna be business books. It's gonna be about everything from like fantasy to historical fiction to poetry.

• 1:03:52Ryan Holiday?

  That's right. No, no, that, that, that's true. Um, I, I like that. I like that also. I think books shouldn't just be, uh, you know, about current events.

• 1:04:04Speaker 01

  Totally.

• 1:04:06Ryan Holiday?

  Well, this is awesome, man. Uh, I'm, I'm so glad we got connected and, uh, this was a good way to get to know each other, I think.

• 1:04:12Speaker 01

  Yeah, man, I, I love it. I've never done a, an intro conversation in the form of a podcast, but I love it.

• 1:04:18Ryan Holiday?

  Well, I've, I figured, I don't know about you, but I, I've, I've never had a like, let's get to know each other phone call that either wasn't a complete waste of time or wasn't so good that it should've just been recorded. Do you know what I mean?

• 1:04:32Speaker 01

  No, I know. I think it's really smart.

• 1:04:35Ryan Holiday?

  Uh, I figured we'd try it and I think, I think it went well. Well, uh, this was awesome and, uh, I'm gonna check out all these sites and, uh,

• 1:04:42Speaker 01

  Yeah, man, we'll be in touch and let me, let me know if I can be helpful in any way.

• 1:04:45Ryan Holiday?

  You got it. Let me know when you're in Texas.

• 1:04:47Speaker 01

  I will. Talk to you soon.

• 1:04:50Ryan Holiday?

  You know, the Stoics in real life met at what was called the stoia, the stoia po kiloe, the painted porch in ancient Athens. Obviously, we can't all get together in one place. First off, because this community is like hundreds of thousands of people, and we couldn't fit in one space. But we have made a special digital version of the stoia. We're calling it Daily Stoic Life. It's an awesome community. You could talk about, like today's episode, you could talk about the emails, ask questions. That's one of my favorite parts is interacting with all these people who are using Stoicism to be better in their actual, real lives. You get more Daily Stoic meditations over the weekend, just for the Daily Stoic Life members. Quarterly Q and As with me, cloth-bound edition of our Best of meditations, plus a whole bunch of other stuff, including discounts.

• 1:05:35Ryan Holiday?

  And, this is the best part, all our Daily Stoic courses and challenges, totally for free, hundreds of dollars of value every single year, including our New Year, New You challenge. We'd love to have you join us. There's a two-week trial, totally for free. Check it out at dailystoiclife.com.