The Daily Stoic - Balancing Purpose and Profit | Sam Parr PT 1

Episode Date: March 23, 2024

In this two-part conversation, Ryan talks with entrepreneur and CEO, Sam Parr. Together they discuss being (or not being) goal oriented, adding sustainability into their lives, monetizing what you enjoy doing, and more. Sam Parr is the founder of The Hustle, which is one of the fastest-growing media companies in the country, and Hustle Con - a one-day conference that teaches non-technical startup tactics. Sam recently co-founded Hampton which is a highly vetted membership community for entrepreneurs, founders and CEOs. Alongside his companies, he is also a prolific podcaster, hosting "The Hustle Podcast" and co-hosts "My First Million".With his diverse skill set, extensive experience, and passion for entrepreneurship, Sam Parr continues to make waves in the business world, inspiring others to pursue their own ventures and redefine the future of commerce.IG and X: @TheSamParrNewsletter: The Anti-MBA✉️ Sign up for the Daily Stoic email: https://dailystoic.com/dailyemail🏛 Check out the Daily Stoic Store for Stoic inspired products, signed books, and more.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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 St 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 for a walk, to sit with your journal, and most importantly to prepare for what the week ahead may bring. Hey, it's Ryan Holiday. Welcome to another episode of the Daily Stelic Podcast. If you're following closely, which I assume you all are, with bated breath, my recovery, I got my first run in on Monday, did a mile, walked a mile. Then Tuesday, I ran two miles, walked a mile.

And then today I ran four miles. I'm not exactly back, but I feel better. Actually, I felt a little blister popping up on my heel, which was unpleasant. And then also I said, I'm grateful for it, right? Because it means I'm getting to do the thing that I like. And I will pay the tax, as Seneca said, I'll pay the tax. If a blister is a result of getting to run again,

I'll take it. But it's funny because the topic actually came up when I had today's guest on the podcast. I was talking about how I was a little bit out of commission because of the ankle and that I was having to think about it as its own kind of marathon or ordeal to not get to do this thing that I get so many physical and mental benefits from. I would have to practice the virtue of temperance in holding back as opposed to pushing forward. And we talk about that more in the second half of the podcast, which I'll bring you later in the week.

But in the first one, Sam jokes that this is the business edition of the Daily Stilett, because we talk about money, we talk about growth, we talk about newsletters, we talk about being goal-oriented and how to do things that make you happy, and of course, how to build a life or a business or a career around that. Also, Sam is someone I've known for a very long time. I've known his work for a long time

because he's the founder of The Hustle, which was a huge newsletter and media company. And we met at a conference in Colorado, I think, and hung out and became friends. And then he moved to Texas and we've gotten to see each other quite a bit as well. I've been on his podcast, My First Million a few times. So I'll link to those episodes. But in the meantime, I wanted been on his podcast, My First Million, a few times, so I'll link to those episodes.

But in the meantime, I wanted to bring you part one of my conversation with the one and only Sam Parr. You can follow him on Instagram and Twitter, at the Sam Parr. You can get his newsletter, The Anti-MBA, and check out his podcast, My First Million. I'll talk to you in the next episode. If you want to focus more on your well-being this year, you should read more and you should give Audible a try.

Audible offers an incredible selection of audiobooks focused on wellness from physical, mental, spiritual, social, motivational, occupational, and financial. You can listen to Audible on an incredible selection of audiobooks focused on wellness from physical, mental, spiritual, social, motivational, occupational, and financial. You can listen to Audible on your daily walks. You can listen to my audiobooks on your daily walks. And stillness is the key. I have a whole chapter on walking, on walking meditations, on getting outside.

And it's one of the things I do when I'm walking. Audible offers a wealth of wellbeing titles to help you get closer to your best life and the best you. Discover stories to inspire, sounds to your best life and the best you. Discover stories to inspire, sounds to soothe, and voices that can change your life. Wherever you are on your wellbeing journey, Audible is there for you. Explore bestsellers, new releases, and exclusive originals. Listen now on Audible.

I'm Matt Ford. And I'm Alice Levine. And we're the hosts of British Scandal. In our latest series, we're visiting one of British Scandal. In our latest series we're visiting one of the rockiest sibling relationships ever. Okay so I'm thinking Danny and Kylie. No no no I'm thinking Anne Boleyn and the other Boleyn. No no Barry and Paul Chuckle. No it's Noel and Liam Gallagher. Now these two couldn't be more different but they're

tied to each other in musical dependency. Despite their music catching the attention of people around the world, Liam's behaviour could destroy their chances. However, their manager saw an opportunity to build a brand around their rebellious nature. It's got fights on boats, fights on planes, fights on land. They just fight everywhere. If you like fights, you'll love this. To find out the full story follow British Scandal wherever you listen to podcasts or listen early and ad free on Wondry Plus, on Apple podcasts adjustment than the pain from the thing.

Yeah, do you lift weights? Not like a lot. I mean, I have like a gym, but I Don't think I could do that either On your upper body you could yeah, but so I need I need the high of cardio. I feel that yeah Yeah, and I I mean you just got a swim or something which I know you're in the swimming. I do like swimming I'm I told myself I would do like a week completely of nothing because I mean it's you're still using your ankle when you're swimming but of nothing, because I mean, you're still using your ankle when you're swimming. But, like when I do, like when, it doesn't matter what I do, I still need the card, especially if I'm writing,

which I just started the new book, and so, if I don't have it, I go like out of my fucking mind. And dude, do you have like a whole like complex here, like a team and everything? Yeah. I didn't realize how. I think we talked about this when I was on your thing yeah you talked it you said you had five or six I don't know it just we're all remote it just doesn't feel as cool it feels cooler now that yeah that you have stuff here yes like my team

I've got a lot of people but it's like I'm in my bedroom that's true yeah no it's like a real it's an office right it's an office that's also a bookstore and that's like cool now right oh to have an office is cool yeah like cuz like I mean I had an office like this three years ago. And that's like cool now, right? Oh, to have an office is cool? Yeah, like, cause like, I mean, I had an office like this three years ago, but now I'm like fucking in my bedroom in my pajamas, like the numbers are good, but like that's nothing else is good. I'm lonely. Yeah.

Yeah, I don't know. Like the original idea was this was all gonna be a complex. That was from the beginning. We set it all up. And then like, I think we hired our first two people was this was all gonna be a complex. That was from the beginning. We set it all up and then, like I think we hired our first two people in February of 2020. So then that all went out of the,

you know, out the window for like two plus years. And then now it's like, every once in a while my wife and I would be like, oh wait, this is what we're, like this is what we were planning on happening. Like this is, it sort of snuck up on us. Where do your kids go to school? Around here?

Yeah, around here. And your wife is, she works with them? She was here, she just went to go pick one up from school. My wife was gonna come, but her baby was crying too much. Yeah, I think you start, maybe we were late on it, but anytime you can avoid getting in the car, you should just avoid getting in the car. I know, but she loves loves you and we've been to the bookstore before and she wanted to get out But anyways, yeah, I'm just I don't it's I'm only like four days in so I don't I haven't got the withdrawals yet

But the withdrawals will happen from what not exercising. Oh, you're only four days in so this is the second time I did like my foot's all bruised up and everything. So like, I'm trying to like, I'm actually like, I decided to think about it. Like, okay, the marathon is like, how long can I go and not lose my mind? That's a good way to think about it. Do you see Casey broke three?

Three hours on the marathon, I did see that. That was a great video he made about it. It was, it's really cool. He's like hardcore. Like he runs like a lot. Do you know who Sahil Bloom is? He's a buddy of mine. Right. No, he doesn't live here. But he started training and seven months after training, he did two fifty seven.

A marathon. Yes. That's nuts. Nuts. Which marathon? Or you just just 20? No, no, he did. He did a real race. I don't remember, but he did somewhere in Boston or something, not Boston, but somewhere around there. Wow. He did it.

And he told me he was gonna do it. And I was like, no, you're not. You're not gonna be able to do that. And then he ran 17.45 in the 5K. A lot of people are very big on goals. I don't really do any fitness related goals whatsoever. I don't think he had a goal. He was just like working out and he was like,

I'm gonna try this race. Let's, I guess it was a goal, but it wasn't like, he was just like, this is fun. Let's just keep going. You had something, you were doing the combine or something? Yeah, I do it. Yeah, yeah, I did really well. I did average for a wide receiver.

Really? Yeah, but- So walk me through this. I'm a, are we recording? Yeah, yeah, yeah, we, yeah. I was a division one track and field athlete. Okay, it's not like I roll up roll up the couch. Like I was built. But how long ago was that? Years ago, but I still train for it. Yeah, I still like workout and I and fast twitch muscles like you either have it or you don't.

So like me trying to run a marathon, it would be it would be very challenging for me to no amount of training would make it as easy for me as it is for someone who's slow twitch muscle. Yes, right. Someone who can do long distances for someone who it's hard to do long distance. Yes. And like I could roll out of bed and jump 30 inches in the vert like I was always able to do that. And I can still do that. And so I trained for a quarter to do it. I ran for six in the 40. I

jumped 33 inches in the vert 10 10, seven in the broad, and then I benched 225 16 times. And that's like almost about average. How far from that was your, was it from your average though? Like, so when you were High school and college, I did a lot better. Okay. But I mean, when you were like, hey, I'm gonna, I'm gonna see how I can do in the NFL combine. Did you have a baseline? Like, how far is that from where you were when you had the idea to do this crazy thing? Not significant. I was 70% there. Wow. Yeah, but I just

didn't get out of shape. Because I work out a lot. And I pick a new goal every quarter. But also, again, it's like, you sometimes you have it or you don't like there's some shirt and that just happens to be my skill set. And I was born a little bit built to do that stuff. And I've always been able to squat heavy weights Like I I could roll out of bed and squat like 380 or 400 like without too much training But if you try to get me to run a marathon I would I could I mean I couldn't run one mile right now faster than Seven minutes you pick a fitness goal every quarter. Yeah, typically right now. I had a kid

So like I'm a little wanderer. Right now I'm like just stay fit while working the least amount in the gym. Yeah. But yeah, I usually pick a quarter. Usually it's lately it's been like a bench or squat goal, the combine. Right now I'm slowly gearing up. I want to do an ultra marathon. Before that it was... Have you done a marathon between there? No. I've done... What's the longest distance? I've done a half Ironman. Okay. So I ran 15 or 18 miles before in a training run. But the ultra seems easier actually than running a marathon fast. You know what I mean? Yes. Yeah, sure. Sure. Sure. Because an ultra marathon is like, are you alive at the end of it? Yeah. That's success versus like how fast can you do this thing? Right.

And I actually think running 50 miles at a slow pace will be easier than running marathon when you're red lighting. You know what I'm saying? Maybe, yeah, I don't know, I haven't done that. Well, neither have I, so we'll see. No, as a theory, it makes sense to me. Like, and the competition is less

in the sense that everyone in the ultra marathon I would make up is just trying to not die versus the marathon which is like you're racing against each other. You don't pick goals? I don't, I don't pick any fitness goals. So do you have programming? Like how do you know what you're gonna do next week? I just do the same thing like every week.

I just run every day or sometimes I break it up with swimming or biking, but for me, it's more I just do that thing to get to even every day. So typically the way that you gain muscle is you have to do progressive lifting. Yes. Meaning more weight or more reps, less rest, whatever it is, you don't have any progressive.

No, I would say it's almost entirely mental and emotional regulation. And the fact that it is a physical activity is a coincidence. That's funny. No, I like to have some type of target, like a benchmark where I can see some type of improvement. So it could be like stretching.

It's like this quote I'm gonna try and do the splits. Like let's just see what I could, I like improving. There was a joke on Eastbound and Down where someone asked if he's training for a marathon or something and he goes, I'm trying not to be the best at exercising. No, he's like, I play real sports. I'm not trying to be the best at exercising.

I sometimes think about that. I'm not trying to win at my hobbies. I like doing my hobbies. Yeah, I understand that. I'm like that with reading. So when I read, I tell people I don't read to learn. Huh? I read because I like reading interesting topic. Yes. And so I like I was looking at your bookstore. There was like the self health section. I was like, Oh, between the age of 20 and 28. I read all

of these. Yeah. And then now I haven't read any of those in years. And it's just strictly what I find interesting. So with reading, it's strictly interesting. Learning sometimes happens. Well, it always happens. But that's not the main point. Yes. But yeah, with working out, I tell people, well, actually, Scott Galloway was on your pod. He said, I want to he said something that was amazing. Okay. Do you remember what he said about he exercises? He says, I want to be able to kill and eat everyone in the room or outrun them. And I was like, that's great.

That's like I kind of work out that way. But I also just say I want to look awesome, feel awesome and live to be old. Yes. And feel great while I'm old. And that's basically it. Yeah, I think I see this with reading where people are like into speed reading or they tell me they listen to audio books

on like eight speed or whatever. It's bullshit. And I go, why? Like I enjoy doing it. I don't try to rush through it. In fact, like there's- Well, I think speed reading is nonsense, right? Well, of course, I think it's a scam.

But the point, there are people who are trying to do it faster, right? Like even if speed reading does not exist, there are people who are trying to do it faster, right? Even if speed reading does not exist, there are people who are trying to read faster. Meanwhile, there's slow eating, actually pleasurable activities. People try to make take up more time, not less time. Yeah. For building companies, I've been trying to build companies slower now.

Like, projects, like businesses build slower. Yeah. Because what's the point? I'm trying to build companies slower now. Like projects, like businesses build slower. Yeah. And I've been- Because what's the point? What are you rushing towards? It not being over? In the next thing?

I used to rush towards things and I'm happy I did. No, I'm saying that to me the question is like, why are you trying to get this over as quickly as possible? Like I thought you enjoy doing it, you know? And obviously running, if you're not doing it quickly, you're not really running, right? And so you're not getting any of the, like, I also walk, but the point is there are some things-

How many steps a day do you walk? I don't know, I don't check. You think you get 10,000? Easily, easily, yeah. Really? I mean, obviously not the last- Eight days. Yeah, or whatever. But no, I'm always walking. And I usually do my phone calls walking.

I do everything walking, but I'm always walking. And I usually do my phone calls walking. I do everything walking, but I'm not trying to get it over with. I like doing it. Like lately I've been running in the morning, so I run, I watch the sun come up while I'm running, then I come home, and then I sort of go. I'm trying to get to an emotional and like hormonal place where I'm chill.

And if I don't, I can feel it. Like I can physically feel it. Well, because you're not a chill person. Oh yeah? No, you are a kinetic, you have kinetic energy. Like when I hung out with you a few years ago, like you do what I do as well. Your legs are bouncing. Like you need to move.

I don't think you're a chill person. I think maybe you're a chiller. No, no, I was joking. I'm definitely not a chill person. You're not chill though. You're not a chill person. I think maybe you're a chiller. No, no, I was joking. I'm definitely not a chill person. You're not chill though. No, I'm not. No, not at all. I think I'm an intense person and that is,

I would rather get that energy out there than in other places. No, and I feel that usually when I think about working out, it's just like, you know, like when your dog, like you're like, he needs to go for a run. Like he's insane. That's how I kinda, I feel about it. I it's just like, you know, like when your dog, like you're like, he needs to go for a run. Like he's insane. That's how I kinda, I feel about it.

I'm like, I'm going insane. I gotta get out, I gotta move. I gotta tire myself out. Yeah, of course. No, and so, and I know when I'm writing, I'm usually generating a certain amount of frustration, right, because you're not anywhere close to finishing. And you're, basically, when you're in the midst of a creative thing,

there's some parts of it that are pleasurable, but for a good chunk of it, what you're doing is just inventing problems for yourself, right? Because you're just going into areas that you then have to figure out and solve for, right? Like, well, maybe I'll say this, or maybe I'll say this, and then I still have to figure out how solve for, right? Like I'm, well, maybe I'll say this, or maybe I'll say this, and then I still have to figure out how that's gonna go. And it will be months from now until that's like perfect.

So I'm just creating a bunch of open-ended frustration effectively, right? So if I don't have outlets to work out that frustration, other things are going to get the brunt of that frustration. So that's what the practice is for me. Do you, with your family and you have kids and everything, do you acquire a lot of things?

Like physical things? Yeah. Are you a conscientious consumer? Were you trying not to buy a lot of crap? I try to get rid of crap, but I'm not super conscious about not acquiring crap. But I'm also not conscious about acquiring crap. Well, you said something about, um, you're doing this project and that just creates

more product problems for you lately. I've been noticing I'm like becoming gone, like so into not buying things that like give clutter in my life. Sure. Cause it wears me down so much. So I've got to, I I've had like nice cars and I'm like, this fucking sucks. Like this sucks. Like these tires are $2,500.

I don't even wanna drive this thing. It breaks or- You go to turn it on, the battery's dead. There's just like, oh, you have to have special insurance for that. You don't realize how many problems you are purchasing. No, and then I have an assistant to help me manage a lot of this stuff.

And then I gotta go buy a bigger house to store the stuff. And then I've gotta pay money for 1-800-GOT-Junk to come and throw away the stuff that held the stuff. Then I've gotta buy some more stuff to store the stuff. I'm like, that's been my thing lately in 24 is I can't stand stuff. I'm trying to get rid of everything and I don't want anything.

There's a George Carlin joke about how do you, it's stuff to other people it's shit. And then realizing also like as soon as you're not there, what it is to other people, how quickly it becomes obviously trash. Like if you're going through someone else's house or you are moving or whatever,

you suddenly see all this stuff you've acquired from a different lens. It's the worst. You're immediately able to get rid of it. Whereas, I think one of the hard parts about having kids is so much stuff acquires a certain emotional significance to you, even though it is the same garbage. And I'm angry at myself because I'm like,

I need this stuff. Yeah. So what I've been trying to live by is, you know the phrase reduce, reuse, recycle? Get rid of the recycle part. That's bullshit. Yeah. You know like recycling is nonsense.

Like it gets all thrown away. Yes. Metal is easy to recycle. Everything else is done. Yeah, but like, you know the blue bin? Yeah. That's bullshit. Like you can't just throw like cardboard with ketchup on it,

a green glass and a soda can into the same thing and it magically gets turned into a thing the only we think all Plastics are the same but every plastic melts at a different temperature gets turned is you can't just not all plastics No, yeah, and it doesn't like and now China used to buy a lot of recycling They don't really do that anymore So like I went and talked to for some projects we to do, I had an interview like people who owned waste management companies, I'm like, dude, this all gets thrown away. This all goes to the garbage.

And so I'm like, all right, let's just get rid of recycling. I'm just gonna reduce reuse. That's it, reduce reuse, that's it. It just not acquires stuff. And anyway, it's been bothering me. Yeah, I mean, like I went through my garage the other day and I looked and I was like, this garage is a graveyard. It's a graveyard of kids I don't have anymore, right?

Like in the sense that, okay, here's like the single stroller, then the double stroller, then the running stroller that we use, but then I broke, so then I got another one. And it's just all this stuff from eras of my kids. And my kids aren't even that old, right? They're like, oh, this is seven. But already at seven, you have all these different phases that they've been

through and are not in anymore. And the garage is just, all these different things are like little gravestones of a thing I won't do anymore. And so, there's part of you that just goes clear it out, and then there's the other part of you that goes, I loved that, and then you don't wanna get rid of it, and then you just keep it. And like my parents now just like unsolicited,

it's like, oh, here's another package of plastic from my childhood. I can't stand it. And then what they're basically saying is like, here you throw this away because they won't do it. You have this book called Perpetual Seller, right? Perennial Seller, yes. Sorry, Perennial Seller.

I saw you give this great presentation on, I think you mentioned like zildjian zildjian symbols. Yes. How do you say it? Yeah, zildjian, I think. And like brands that last 100 plus years and classic books that last and they actually sell more. And I think that you're on track to doing that. And so you might be familiar with this. But have you heard of the buy it for life? There's a buy it for life movement. You know what that is? So it's a big subreddit and there's groups on Facebook for it. But it's this idea, and I used to do this all the time where I'm like, well, I don't need the thousand dollar thing. I'll just buy the $50 thing. But the $50 thing you end up throwing away and you buy much more of that stuff. And so what I've been really gung-ho about is the buy it for life movement. And so you buy things that can last decades. So for example, or hopefully like time

So for example, we're buying a crib right now for my kid Yeah, I want to get like I've been suckered into this Amish thing which I don't even know if it's truly Amish but the concept of like people did this by hand and Like there's this one crib that it's a normal crib and then it turns into a toddler's bed Yeah, and then you get this insert then it turns into a toddler's bed. And then you get this insert and it turns into a full-size bed. So ideally they can have it from age zero to 18 or whatever.

And then they say, and then their kid can actually use the same thing. And so what I'm trying to buy is things that can last a lifetime or more. Hello, I'm Hannah. And I'm Saruti. And we are the hosts of Red Handed, a weekly true crime podcast. Every week on Red Handed, we get stuck into the most talked about cases. From Idaho student killings, the Delphi murders, and our recent rundown of the Murdock saga.

Last year, we also started a second weekly show, Shorthand, which is just an excuse for us to talk about anything we find interesting because it's our show and we can do what we like. We've covered the death of Princess Diana, an unholy Quran written in Saddam Hussein's blood, the gruesome history of European witch hunting, and the very uncomfortable phenomenon of genetic sexual attraction. Whatever the case, we want to know what pushes people to the extremes of human behavior.

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Hello, I'm Emily, and I'm one of the hosts and music, or by subscribing to Wondry Plus in Apple Podcasts or the Wondry app. pop star and shuttlecocks, you know who I'm talking about. No? Short shorts? Free cocktails? Careless whispers? Okay, last one. It's not Andrew Ridgely. Yep, that's right, it's stone-cold icon George Michael. From teen pop sensation to one of the biggest solo artists on the planet, join us for our new series, George Michael's Fight for Freedom.

From the outside, it looks like he has it all, but behind the trademark dark sunglasses is a man in turmoil. George is trapped in a lie of his own making with a secret he feels would ruin him if the truth ever came out. Follow Terribly Famous wherever you listen to your podcasts or listen early and ad free on Wandery Plus on Apple Podcasts or the Wandery app. Interesting. My parents did send me like my wooden high chair from when I was a kid, but I would never put my kid in it. It's like a death trap, right?

Like, so the problem is some of the stuff, it was designed to last, but it was designed around assumptions that haven't held up. Sure. But I do, speaking of kids, there's one, I think I put it in the talk sometimes. There's like, I saw this picture of like an LL Bean jacket. It's like an LL Bean kids jacket. And it has like, you know, the spot where you write your kids' names so they don't lose

it at school. But then underneath it, it has another line and another line and another line. And the idea is like, you should be writing multiple kids names in this jacket. And Patagonia, if you go to Patagonia's website, they have a used section, like where they're encouraging people to resell their products, which ostensibly deprives them of revenue

from the new stuff, right? The planned obsolescence is a capitalistic assumption built into most brands. And here though, the marketing of it is, I think, important. They're saying, first off, we actually do care about the environment. We care about the environment more than us making more money. But they're also saying our stuff has resale value

because it's not garbage. Yeah, and I'm a big fan of all that stuff right now. Yeah. Like that whole movement. Yeah, I think that's right. I mean, I have a pair of Red Wing boots that I'm on a big fan of all that stuff right now. Like that whole movement. Yeah, I think that's right. I mean, I have a pair of Red Wing boots that I'm on my fourth sole. Me too. I need to, I was gonna bring them into the office.

I found there's a little boot store, like a shoe repair thing across the street that's been in business since like the 40s, and I was gonna bring them there and have them send them in and they turned into like a new pair. It's crazy. That's awesome. And I remember when I bought them. And they turn into like a new pair. It's crazy. That's awesome. And I remember when I bought them- And they look prettier, they look cooler.

Yes, of course. Well, I remember when I bought them, they were $300. And that was expensive. I thought that was insane. I mean, I've since bought like sneakers that cost that much money that are already falling apart. Meanwhile, yeah, almost 15 years into these shoes.

And they're amazing. What I've been focused on lately is things that last forever. I think that's right. I think our generation, if you stay in the same house forever, if you don't move a lot, there were assumptions that I think made it, that society shifted, it made it easier

and it made it a lot more sense to like get your stuff from Ikea than to get like a really good dresser because you were never gonna move that, you weren't gonna be driving that dresser across the country or moving it multiple times. Like, you know, like if a couple is getting married at 20 years old and then staying together forever,

it makes more sense to like invest in stuff that lasts. If everything, the problem is so many other parts of our lives have become ephemeral. So it becomes harder to like invest in stuff. Do you think you'll live in your current home forever or own it forever? I think so. I mean, I haven't found anything that I like better and I've looked, you know, yeah, I think so. I mean, I haven't found anything that I like better

and I've looked, you know? Yeah, I think so. I mean, but I'm different. I bought like, not different, like I'm special, but like we bought like a ranch. You're not supposed, it's not like a house you sell and then buy a bigger house than a bigger house or something. We're gonna probably sell our house

and I'm gonna rent until I find the dream home that I want. And I'm gonna buy a home that I intend to live in for 50 years. But how do you know what that place is? Well, I don't. That's why I'm gonna rent. I'm not gonna rush. I'm just gonna rent a place. You know, our friend Remy, he's like all gung ho about renting and I tend to agree with him of like I'm just gonna rent until I know what it is I really want for a long period of time. When I interviewed Tim, he sat right there. He said he loves this expression, rich enough to rent. He rents too? No, his point is that there are things that like, it's in many cases more efficient to buy something, right? Not in all cases and maybe at homeownership it's not true. But the point is we go like, they do the math and you go like, oh, it's more efficient if I buy it, right?

Or I could save some money over the long term if you buy it. But if he's saying, what if you can get to a place financially? We don't care. We don't care, you're just doing the thing that is easier and less of an imposition for you. Yeah, so I'm now renting, starting in a few weeks, a furnished home.

Yeah. And I'm not gonna own it. I'm bringing my clothes. Wow. Yeah, that. Yeah. And I'm not gonna own it. I'm bringing my clothes. Wow. Yeah, that's it. And I'm getting rid of everything. I don't want any of this stuff. Okay, you mentioned Scott Galloway earlier.

I messaged you when I saw the clip, but I was very struck by, you had him on My First Million, and you guys were talking about money. Dude, that clip went viral, and I got made fun of so much in the comments, and I think they missed the point. Well, I wanna hear the point,

because I thought it was, I've known you a while, and I thought it was very vulnerable and real, if not rather unrelatable for probably 99.9% of the population. But basically he was asking you, you'd sold your first company and how much you'd made. And it seemed like you were ashamed to say that you made only $20 million.

I wasn't ashamed. So let's recreate the clip. So Scott Galloway, I'm a huge fan of Scott's. Yeah, he's great. Wildly successful. Yeah. On the podcast, somehow, well, it always comes this way because it's called My First Million.

We talked about money. Yeah. And he was like, basically, he said, he's worth over nine figures. So he's like, I have a hundred million plus liquid. And I was like, that's wild. How much you spend per month? And he's like, sometimes 400 grand a month.

And I was like, that's intense. That's insane. That's wild. That's stressful. And then he goes, all right, I'm sitting here telling you everything. You tell me, what about you? I didn't tell him my net worth,

but basically I had a company that I sold three years ago and I walked away with around $20 million. And he asked me that and I kind of choked up at first. And then I said the number. The clip has been seen millions and millions of times and everyone thought that I was ashamed. I don't know if I was ashamed. Maybe, so I guess the thing about making money and earning money is there's like crazy amounts of levels. So someone may have saw my clip and they're like,

no way out, we'll ever have 20. But then I'm with a guy who's got 100 and then I've got friends that have billions. And so maybe there was a little bit of like, well, I'm on a good track, like, you know, it's working out, not necessarily like I'm done. Yeah. Because it certainly doesn't feel that way.

But it's like, oh, I'm on the right track. But also like, he put me on the spot and like, I had like. No, you're talking real numbers instead of hypotheticals. So there's something I think inherently vulnerable about that. And then I could see someone being ashamed for the complete opposite reason also, like they're self-conscious and they think money

isn't something that you should talk about, right? Like I could see someone being embarrassed for that reason also. But yeah, I took from your body language and your answer that you didn't feel like that was, something you didn't feel like it was a lot, like you need more, but you felt like comparatively, that wasn't a big success.

Well, I do feel that way. Yeah. I don't think I'm ashamed of that though, but I do feel that way where I feel like that is a nice, that's a nice chapter in my journey. And there's more, I'm gonna have more chapters. And it's not necessarily the money, That's a nice chapter in my journey. And I'm going to have more chapters. And it's not necessarily the money.

It's just that we were talking about fitness and we were talking about running. I said I like goals. I get a rush. It's exciting for me to see progress in my life. And it's nice having a goal to do more. Additionally, my podcast is a lot about money and I have crazy successful people on who are both successful in the traditional sense

but also they're happy, I admire them, whatever. You've been on, I admire you, all these people I admire. And a lot of people look up to me and they'll ask me questions, they'll ask me for a photo and I'm like What the fuck these guys are way cooler like they're the ones I like And so I get a little self-conscious about being considered a guru and things like that where it's like no I need to be I need to do what i'm talking about. I'm not someone who talks about it. Do you think uh,

There was part of you that wanted much much more and that's so much money. And at the time, at the time, I was like, I don't know if I was going to be able to do that. I was like, I don't know. I was like, I don't know. I was like, I don't know. I was like, I don't know. I was like, I don't know. I was like, I don't know. I was like, I don't know.

I was like, I don't know. I was like, I don't know. I was like, I don't know. I was like, I don't know. I was like, I don't know. I was like, I don't know. I was like, I don't know. I was like, I don't know.

I was like, I don't know. I was like, I don't know. I was like, I don't know. I was like, I don't know. I was like, I don't know. I was like, I. Oh, the business or like, you know, personal life? No, personal life. And I was like, that's so much money. And at the time I was spending 3,000 a month in San Francisco. I was spending nothing. I lived for very cheap and I was basically like, I was pretty much almost poor. And he just said that number.

And I was like, okay, well, what sum do I need to have that I could spend that if I wanted to and never run out of money for the rest of my life? And I came up with that number roughly $20 million. And so I said by 30, I want to post post tax have that invested into index funds and bonds like liquid money, not net worth liquid money. Maybe I'll have other stuff, but that's what I want. And so I did it by 31. I sold the company when it was 31. And so I worked backwards. And so my company now is worth probably significantly more.

Some of my competitors who I'm great friends with now, they're probably worth two to 250. And so do I regret selling? Not a chance. I had a goal, I'm happy I hit the goal, and I don't regret it. But I definitely want more, not necessarily for the lifestyle,

but partially because I'm just like, I didn't grow up with a lot, and I'm like always afraid of running out. Even though I don't wanna acquire nice things, I'm just crazy afraid. I think it's just like, it's a personality defect, but also because like, it's like bench pressing. Like I did 295, let's see if I can get 300

in two or three weeks. Like wouldn't that be exciting? Yeah, the paradox of whatever the attitude that makes someone good at growing and achieving, right? The ability to look back and see what you could have done better and to primarily focus on how you could have done more or better. That's obviously a propulsive force. Yeah, and there's downsides. Yeah, the downside is that

it makes it hard to enjoy or appreciate because you're doing that even when you have so surpassed whatever the mark was. Like I wanted to write one book. I thought if I could write one book, that would be success. That would make you an author. I would look at it, it would be, you know? And then I did that at 25, and then I somehow did it like literally every year since then and well past whatever the economic need to do that thing.

So that's not what's driving me. I felt like each time I'd said everything that I needed to say, but then yeah, there's just this part of you that just keeps going. You are who I look up to you because you're like, you're a wise man. Like you're a wise person. Like you, like I read all of your old blog posts,

the stuff that used to be on Thought Catalog. Like I've read off everything. I watched the Daily Stoic. I consume all your, I text you all the time. I'm like, dude, this video was really good. I love this video. My takeaway was that, like I actually consume all your, I text you all the time, I'm like, dude, this video was really good. I love this video, my takeaway was it. Like I actually consume all your stuff, I admire you. Thank you.

But, and even you are like, it'd be nice to be better. Who'd realize to be more, more, more. And so I accept that that's like a natural part of just like, I think everyone, particularly people who are self starters, of which I self identify as. So I just think it's just like, it comes with the territory. Like for example, last night,

I spent an hour cleaning this thing and putting it on Facebook marketplace and I sold it for $400. A, I loved it. Like it felt awesome. Like to get that- What was it? A cabinet.

Like a workbench. Cause you're moving? Well, I'm downsizing and I'm gonna move. But like I get, or like I had an old Xbox that I didn't even know I had. I got a hundred bucks for it. Someone's coming tonight. And like I get joy out of that.

Like that A, brings me joy. But B, there is like a fear of like losing. And so I'm like, oh, I can't just throw this away. I need this. I can't have waste. And I think that that it just comes from, I don't know what it comes from, but it's the same personality type, or it's the same personality

trait of like, this is the numbers that the business did this month, we got to increase that by 20% next month. Here's how. Yeah, there is this kind of, I don't want to trauma sounds like a strong word, but I was listening to I think it's trauma. I was listening to Ramit's podcast a couple of months ago, he was talking to this couple that was very cheap, and they were trying to trace back why they became cheap. And the guy sort of traces it back to his grandmother who survived the depression, and so whenever he would visit as a kid,

she would hear that he saved up his money and bought this toy or bought a piece of candy. She would like, shouldn't do that, you never know where it's gonna come, when you're gonna lose it, or whatever. And he was talking about how that sort of this curse that he and his wife have like born their whole life. And then Ramit goes, and how would you feel

like if your daughter was that way? And you would think that he would go like, well, the whole point of being successful would be to like break this generational trauma and to free my daughter from this sort of sense of scarcity about money and finance. And then immediately the guy's like, well, you know, it's been like, he's immediately going like,

but it served me so well, I have to like pass it on. And so he couldn't see that like his grandmother had like effectively abused him or his parents and then his parents had abused him and now he was abusing his daughter even though they had millions of dollars, they were like sweating over like, who picks up the tab at dinner or something or whether they could afford to like go on this small.

And Rameet criticizes me for this all the time. Of course, no and I do think that one of the, again, this is a first world problem compared to so many other problems, but like whatever was a large amount of money to your parents becomes like a baseline for you, right? And so one of the tricky things that comes along with succeeding financially,

or even just existing in a new world where things, the market is different and money is worth different amounts is to be able to look objectively at amounts and see money as it is, not in whatever lens your parents made you think about it, especially when you've like so blown past that. And I think you see that when you ask someone like,

what's an amount of money that you sweat, you know, and someone will be like, oh, you know, I wouldn't want my wife to spend more than $200. I think I don't have a number generally, it's like different things, which is kind of the problem. Like you should be able to get to a place where like you don't think about anything below this number. Yeah, it's like, you could be like,

what's your hourly rate and is it worth that hourly rate? For me, if I see like clothing, if I see like a disposable good that's like above a thousand, I'm like, do I really want that? Like when I sit down to eat, I don't like think about how much this stuff is on the menu. But then like, if I find out eat, I don't think about how much this stuff is on the menu. But then if I find out, sometimes I just go like, did they overcharge me on this thing? For some other bill for the same amount of money.

Do you know what I mean? Well, I'm paranoid about being taken advantage of. And that's one of the reasons why I got nervous when Scott asked me that. Really? Yeah, I'm paranoid about being taken advantage of. I feel like I get taken advantage of. So you thought he would say like oh You should have sold the company for a lot more money. No about just vultures asking for stuff

Oh, oh you thought by giving the number you were making yourself vulnerable to be yeah, like I'm very nervous about that Yeah, I get quite nervous about that and I'm like like first they have I have a ranch as well and if like I've got like Let's say I have a Tesla at the ranch when I have a vendor coming over to fix my driveway. Like I'm like, I gotta hide, I've gotta hide the car. Really? Yeah, I'm like quite nervous about that. There's a story about Epictetus, he's in his house one day

and he's like in another room and he hears like rustling and he comes in in this slave who sort of clawed his way up from nothing. That's what Epictetus has this like, he has this shrine in his house and he sees a man is stealing a lamp from the silver lamp from his shrine to the gods and running out. And Epictetus is like distraught at first. And then he goes, you know what?

No, I'm being foolish. He says, you can only lose what you have. And he says, tomorrow I will go and buy an earthenware lamp. And he buys a cheaper lamp. He's like, I shouldn't have anything that I'm afraid of being stolen. And I think about that sometimes, like the thing, like I'm purchasing the nice thing,

but I'm also purchasing the worry or the stress or the vulnerability to other people. What I phrase, what I'm really trying to do is, I own my things, they don't own me. Cause I remember like being a kid and like we dented the car playing hockey. My dad flipped and I'm like, I don't ever wanna be like that.

I won't flip, I own it. And so I really work hard to do that. Have you heard, have you read the book, The Courage to be Disliked? So it's like a set in Japan. It's supposed to, I think it's a nonfiction book, but it's about, is it Arthur? Is it Kant?

Kant? Kant, Kant. So, you know, he's one of the big four, like big psychologists, whatever. And the takeaway from that book was basically like, you choose to be anxious a little bit. And you self-identify as an anxious person, therefore you will continue to be anxious.

And when people talk about the stuff, well, at least when I talked to Ramit about this, he's like, dude, you're being a tightwad because you are self-identifying as a tightwad and you're gonna continue perpetuating that, particularly with your children, with your wife, with the rest of your family, because you have self-identified that.

And it's not particularly easy to not self-identify that. That requires- His point is actually the reason it's so hard to not be cheap is that most people who are cheap think it is a virtue and not advice. Correct. He's like, you are taking pride in this stupid thing. Yes. And I believe him to be right. I believe he's right. But that is a very, like, you know, that's a hard thing to overcome. But I believe that that mentality is correct. you know, that's a hard thing to overcome. But I believe that that mentality is correct. No, the ability to adjust what that amount of money is relative to your net worth is work, right?

So, you know, when you were young and struggling to save up a thousand dollars to put it in the stock market or whatever, you were so proud of that and you should have been proud of it. And then as you get older, that number has to be 10,000. And then if you get to 100,000, then you hear about, you know, I don't know, some billionaire makes a hundred million dollar bet on something. Like that seems like a lot of money and it is to you. But to them, it's relative to their net worth, a reasonable amount of money with the certainty

or the certainty they have about the bet or the potential upside they have about the event. And so to be able to adjust as you grow what is reasonable or unreasonable is really important. Otherwise you are it's like it's like you were an animal in one size cage, and now you're in a bigger cage, but you're only pacing like this little outer bound and you don't understand that you have a lot more space or freedom And and that that seems it seems foolish to be artificially constrained Well what I told my wife yesterday was like my personal philosophy and my personal operating system is not scaling with

Yes, some of my success or some of the demands that I have people have of me or whatever and that's that's actually a Pretty significant failure that needs to be addressed. Well, and you learn it, really you learn a lot of these lessons as a business before you learn them personally. So like as a business, you go, well, I could do all this myself, but I need businesses hire people.

So I'm gonna hire someone. And then you understand, oh, when I hire people, it helps me make more money or it helps me scale what I'm doing. Or if I don gonna hire someone. And then you understand, oh, when I hire people, it helps me make more money, or it helps me scale what I'm doing. Or if I don't hire someone, all that money just goes to the government, or whatever, right? You sort of, you're able, because the business is not you,

the business is this external thing. You go, hey, we need office space, or I need this tool, or what, you know, you're able to see- There's a much clearer ROI. Yes, and then in your personal life, you struggle to make some of those very same judgments, even though the same thing applies. What's that phrase? A penny poor pound. What is it? Penny wise pound foolish. Yeah, that's exactly what it is. Do you do you do you and your wife

track your spending and income? Like do you have like a meeting once a month or once a quarter or once a year? No. So do you just make decisions on like, oh, let's just do this? Yeah. Really? Yeah.

How does that make you feel? Do you think that's the right thing or not? I think in some ways it's the right way, in some ways it's not. I think one attitude I have, maybe you disagree with this, but I go like. I'm not saying my way is the right way. No, no, no, I'm just saying like,

I try not to think that much about money. Right, to me that's like, I think if you are thinking about money all the time, you're not rich. Yeah, I agree. You know, and so I try to be efficient, I try to be smart, I try not to be reckless, but I also try not to like,

I don't know, obsess over everything in a spreadsheet or like some sort of interface with a graph. Like I just try to make good decisions, I try to set up systems that automate most of what I should be doing, I try to have just generally good habits, tastes, practices, and then I try not to obsess that much about optimizing. I'd rather focus on optimizing the things

that I get a lot of meaning out of, which would be like my work, let's say, as opposed to my final financial picture. What I do is I just look at what my, like the fifth of the month, I'm like, what was my income last year? Because I've got a variety of sources and I'm like, how do we do, whatever. And then I say, like, well, we'll like say like, all right, what do we want to be in

five or 10 years? Like, let's try to average roughly this per month and spend. And I don't actually care entirely where the money goes. I'm just saying like, ballpark, this is what, like hey, we're way under this month. If like, just so you know, like, if you want, like, you don't have to, you know, you could splurge a little bit. Do you think a month is too small of a unit of measurement

for what? No. Is it a much larger, bigger picture? I think it's annual. I think of it an annual, but like, I'll just like, like I don't have categories set up on my budget. I'm just like, our spend, we spent this much money this month.

I'm just like, all right, that's interesting. That's cool. I'm like, wait, what was this $2,000 purchase here? Like, oh shit, we forgot to cancel this thing. So that's usually why I look at it. I'm like, oh, I forgot to do this thing or whatever. Like just admin shit like that. But it's just like, generally,

this is how much I know we're gonna spend. If we go over, that's no big deal. If we are way under, I'll be like, hey, you know, like, we're not spending nearly enough that we said we wanted to spend. Do you want any like services? Like, is there like, would the cleaning lady coming every two days make you happy?

Like, what would make you happy? And so I try to be like conscientious of like what makes me happy and like go spend More on that. Yeah, I think I think one of the things I found with a business that's been helpful is like, okay You understand there's certain like just costs associated with the business and you pay them There's taxes associated with the business you pay them You or other people make mistakes in the business and you just have to pay that, right? There's breakage, stuff gets stolen, you know, there's just like, there's just things that you eat, you know?

But in your personal life, I think because it's a business, you go, that's business, I don't control that. But then in your personal life, people think they have much more control over it than they do and so each one of those things that they have to eat control over it than they do. And so each one of those things that they have to eat goes down much more painfully. Whereas if you can treat your life a little bit more like a business, you won't sweat every one of those things. Like Seneca says, you pay the taxes of life gladly. I don't think he meant just like the taxes you pay the government.

I think he just meant like there's a cost associated with all the things in life. But I think we have this fantasy of control or of getting it perfect. And that makes us anxious and stressed out about a bunch of things that if you just sort of shrugged your shoulders to, not only would you be happier, in the end, your final like sort of picture would probably be Exactly the same as it was if you were sweating it and have you heard of um the company nerd wallet

Yeah, so it's like a credit card. Uh, yeah review website I uh was buddies with the founder tim and jake the two guys started it I think it's publicly traded now at like a one and a half billion dollar valuation. It's like a huge great company, whatever. He advised the hustle when I first started. He gave me a lot of advice and he was a small investor. And I remember when our business hit 100 grand per month in expenses, I think we were making 150,000 in revenue or something like that. And I went to him and I go, Tim, I'm so stressed. Like look at my spreadsheet. Like we're spending 100 grand a month. Sometimes I went to him and I go, Tim, I'm so stressed. Look at my spreadsheet. We're spending 100 grand a month. Sometimes I don't even know what we're spending on.

And he's like, yeah, but you made 150. He's like, let's try to like, what can we do to make you spend 200 grand? And then now you'll make 300. And I was like, wait, what? Doesn't that stress you out? He goes, no, dude, it's just a number on a spreadsheet. And I'm an investor. He's like, as CEO, I'm just investing capital into things that can turn to more.

So if I have a machine that turns $1 into $1.50, I wanna spend all of my money into that machine. And he had that talk with me, I was like 25 trying to figure this out. And my mind was blown. I was like, you're right. It's just with the business, it's way easier. It's just like, there's an input

and then you have to build a machine that has the output that's higher than the input. And that's actually kind of easy to do, or rather, it's simple to do. Yes. I'm Peter Frankenpern. And I'm Afro-Hersch. And we're here to tell you about our new season of Legacy, covering the iconic, troubled musical genius that was Nina Simone.

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at just $50 a month, backed by our Wi-Fi satisfaction guarantee. Visit rogers.com. But it's kind of a bedrock assumption that you either get and that allows you to make things that grow in scale or that so challenges your sort of scarcity mindset or desire to control things that you're just not cut out for business or risk. Yeah, and that totally changed my perspective

of spend more, spend more profitably rather. Yes. And that was kind of a paradigm shifting moment that he had with me. Yeah, it's like you wanna keep costs low, but when your costs were lower, you almost certainly were making less money as a business. Yeah, so I was like, spend more.

Because he's like, no, you're not spending, you're investing, invest more. And I was like, oh my God. I think for a long time I had this impediment, I just didn't wanna hire anyone, I just didn't want any employees. You have six? Oh no, way more.

It's probably like 15, maybe more. I don't know. But this is like for years. This is more when I had the marketing company. And I think there was some good reasons for doing it. Like I had this idea that if I had fixed costs, then I would have to take on clients to pay for those fixed costs

that I didn't actually want to work with. Well, yeah, that's because an agency business sucks. Yes, it does. And so it wasn't until I moved from an agency business, which Brashech was for a long time, to making my own stuff, which is when Brashech started Daily Stoke and Daily Dad and the bookstore and other stuff,

that it was like, oh wait, like, I believe in all the stuff that I'm doing. And so the more I can grow, the more of that stuff I can do. I think Casey said that to me one time, Casey and I said- Does he have a team? He goes back and forth, I think. Like sometimes he does, it depends on what he's working on.

But he said something like, he's like, we don't do projects to make money, we make money to do more projects. And the idea of like, oh, okay, the more I can scale and the more I can bring in, the more stuff I can make, because it's not free to make stuff. Yeah, he had this great thing about, he did this video about being a creator

or something like that. And I think he had a hundred million views before he turned AdSense on or whatever it's called on Google. He didn't monetize his videos. And he was like, I thought I was punk rock. He was like, I thought I was sick. I was doing like, fuck the man.

Like, I don't need this money. And he was like, that was so stupid of me. Because I couldn't afford to make videos, I had to go do all these side gigs in order to make money to continue making this awesome daily vlog. And then he's like, it's also selfish. Like, I have a family, like, I should have been providing. And I completely agree with that mentality of people who don't monetize certain things too early. I'm like, well, is your product good? And they're like, yeah, I'm like, do you want to keep doing it? Yeah Yeah

Then fucking charge money and make money so you can continue doing it And also there's an arrogance in it, right at some point in the future You're going to want to keep doing stuff and people are going to be less interested in hearing from you and doing it Right, and at that point you're going to be desperate for someone to pay you or support you or fund you, right? Yeah, you always gotta get it while it's hot. So get it while it's hot. Like when people are paying you to make stuff or wanna be a part of what you're doing,

the idea where you're like, no, no, no, I wanna keep it artificially small is, I think, silly. I think it's silly. Yeah, I mean, I get that. It's, for what I do, like I talk about ancient philosophy. So there's some people that think the idea of monetizing in any way or supporting it with ads or selling stuff,

they just don't like it. And I get it. Maybe if I was on the outside, I would see it that way. And maybe I see it that way with things that I like. But what these people fail to realize is it's not free. It's not free to have the studio. It's not free to have this studio. It's not free to have this pocket.

Like when you start, when you don't have an audience, all the, even the online tools are free, right? But when you start to have a large audience, they pay you to access that audience. Like it costs hundreds of thousands of dollars a year just to send like the daily stoic email. Who do you, are you using ConvertKit? Yeah, ConvertKit doesn't charge hundreds of thousands

of dollars. But it's a lot of money. But it's a lot of money. And then also I have to have someone edit them. I have to have, there's a lot of management that goes in. If you put out, if you're putting on a show for a million people every day, which is what the daily stoic email is by itself, you can't just do that from your bedroom and do it at a high level, right? It

costs money. And so to be able to continue to do it and to be able to continue to accept new people into it, you have to be able to make money. And then what you find when you make money is that you can then go, okay, I'm going to keep a little of this to myself like you know pay for my house or send my kids to school or whatever and then I can reinvest the bulk of it into making more stuff that I give away for free. Is this gonna turn into your business episode? What do you mean? We want to do a business episode because I want to ask you a question. Let me ask you a question. Go for it. I don't know if your listeners will like this so we could we could move past if you don't like this. Is the email newsletter potentially

one of the greatest business models of all time? It's insane. Mine or all email newsletters? No, not all, if you set them up the right way. So at The Hustle, right now, I've sold it so I don't have access. I think they have close to four million subscribers. Yes, every day four million people get this thing.

Do you know how many people it takes to write that? Three. Yeah, that's people get this thing. Do you know how many people it takes to write that? Three. Yeah. Three people. Yeah. Now, the reason I remember, we had 30 or 40 employees when we sold because we had to monetize it, then we had accounting and all this other stuff. But we, I don't remember the numbers, but I think, so let's say we were doing, we were

doing well over a million a month. I think we're going to do 20 million a year we sold. But let's just say for round numbers, we were doing a million a month and we sent 26 emails per day. So that's like, what is that? So 25 divided by, so that's like, is that what? 40,000 per time we hit send. And we have three people writing. And it's a beautiful business model if you could nail it. So you have a lot of people, right? So Daily Stoke is about a million people a day. It's a beautiful business model, if you could nail it. So you have a lot of people, right? So Daily Stoke is about a million people a day. It's insane.

Obviously we don't send 25 emails a day. No, sorry, we did 25 a month. Oh, sorry. 26 a month. Yeah, so- That's every day but Sunday, I think. Yeah, we send out every weekday, and then there's some other. But let's say we send it every single,

we send it more or less every single day. Now, obviously it's less monetizable than email about business or, you know, like it's a different audience because it's so, it encompasses everyone, which is great, but then from a business standpoint, that's less great than like, these are these people who do this thing.

But that's 25 million impressions or whatever it is. It's crazy. It's a lot. And you basically, it's basically can be, it potentially, it depends on how hard you wanna work, it'd be you and an editor. Yeah, yes, yes. It's insane.

It's a great business model. And I think I recognize that when my agent came to me with the idea for a book, he said you should do this page a day book. And I was excited about it for two reasons. One, I thought I could build something. That's the daily stoic? Yeah, the daily stoic.

I thought, okay, I'll do the book, but then what comes after the book? I thought I would do it like, I could just keep going. It would be something that would allow me to write every day on sort of meditations about this thing every day. But I also liked the idea that it wouldn't be me in the sense that like the word I does not appear in daily stoic and in the emails the word I does not appear. It's a it's depersonalized.

I still write them all. Sometimes I like my editor will help me here or there. I can have someone sort of put together the bones of one for me. So it's scalable a little bit, but it's not like what does Ryan have to say to it? Let me tell you something about my life, right? Which as you write as yourself, it's much harder because it's personal and then you have to think. But the idea of just having this thing that goes out every day

and just the sort of practice of doing it every day has been like amazing. And then yeah, it's a great business because you are creating, you are talking to people every day and then you get to say, while I have you, let me tell you about this other thing, whether it's a sponsor or whether it's one of my books

or there's something that like I just think is cool and should exist and so amazing. Versus your thought catalog days, you some were massive hits. Yes. you, some were massive hits. Yes. Probably most were not massive hits. Yes. That's like the rule of virality is like. Are you writing to subscribers, which is a base, or are you writing for an indetermined unknown audience that you hope will, you will reach person by person. And you can just write better when you are writing to an audience.

Because- That's crazy you have a million people. That's so much. It's nuts. I mean, it started, I, what happened was I sent out an email to my email list then, just like as me, Ryan. And I think about nine or 10,000 people signed up.

This would have been the summer of 2016. And so now eight years later, it's yeah, it's about a million people. Is it all organic? Like, you mean, have we done ads for it? Maybe here or there, like the occasional like the gen thing where you're trying to convert people who are following you on another platform. But no, no, I was looking at our spending. I was looking at when I sold the company, I was looking at the numbers, I think we had spent $400,000 the month before we sold on growing the email list. Yeah, that's crazy.

It's insane. That's crazy. This is just word of mouth about something that really on its face is laughable that there is word of mouth for. Yeah, it's insane, but that's why it's awesome. Yeah, it's great. I love it.

It's the coolest thing. And then obviously we started it's awesome. Yeah, it's great. I love it. It's the coolest thing. And then obviously we started it with the Daily Dad, which is like the second one. You write that one too? I do both. I just write a couple, like I wrote one Daily Stoke email today. I think I did a Daily Stoke and a Daily Dad email yesterday. And I just, yeah, I just chip away at it.

So I think we're right now we're like three months ahead for Daily Stoke, maybe two months ahead for Daily Dap. So our newsletter was news. So there is no, different business. You don't get ahead. And so it was every night, you got to do it. It was really hard. I did it for the first little while. It was very hard. So you made $20 million. What did that change for you? I had less of a chip on my shoulder. I felt like I could be a bad-ass business operator and I still feel like I'm not quite there yet, but I had some, I had some,

it was like, just my parents would be like, shouldn't you be working today? Like when I'm home on Christmas break cause I'm on my phone, I'm like, dog, I am working. And like just getting like a Wall Street Journal headline. It's like See, I told you like this is real. Did you feel like that's who you were trying to prove it to? Yeah for sure and like every ex high school girlfriend like yeah Yeah, like, you know, like people like try to tell you not to be like you probably say this all time

Like don't have rage and like forgive people and I'm like, I don't know It's kind of awesome fuel to improve yourself. The problem is it's hard to turn off. Yeah, and so there's massive downside. But I would never deny someone that it can be very productive. But did it, so it got you there,

but did you feel like when you did it that you had proved it? Because maybe you didn't. Well, it's not binary. It's not binary. So it was like, all right I'm on to something. Like I'm getting closer to having a seat at the big boys table. Like I can some people might take me a little bit more seriously now. Like I have some type of evidence that I'm good at my job and I'm talented at the the trade that I'm trying to master. Which is business. Which is business. You

know I read Mastery by Robert Greene, it changed my life. That's why I purposely use those words of trade and mastery. I remember reading that book, it blew my mind away. So it felt some type of like a sense of, all right, I'm decent at this gig. And it does bring a massive amount of relief. Like, dude, being poor sucks. Like I paid myself, so I sold I think in year four in year one I paid myself 20 grand a year year two 20 grand a year year three

I think it was 50 and then year four. I did pay myself a lot like half a million and because the business was doing good and But like for those first like two or three years in San Francisco, I was on Obamacare because I was like under the limit of like I didn't have a lot of money. And so that shit drags you down. And so the people who say money doesn't make you happy, it definitely makes you happier. And so there was a sense of like, all right, this whole thing that I've spent a lot of time and effort on, like it's given me some sense of security and like, because like if

Gmail made a change, I'm done. You know what I mean? So that felt, that was very high stress. So I did feel a significant amount of relief. The big boys table that you mentioned, I think that that's interesting. Cause I think a lot of people are like, I wanna get into the club.

Or I wanna be one of the guys. A lot of these are male metaphors, of course, because that's unfortunately what business is sort of there. It's actually indicative, right? Because there's this kind of like, immature dude energy to it. Yeah, I think it's a lot of rooted in just like high school being bullied. Yes. Totally.

But there is this sense that you'll arrive at some point, you'll get it at some point, you'll be accepted at some point, you'll get it at some point, you'll be accepted at some point, you'll have proved it at some point. Do you feel like that is real? No, no, no, no, no, no. Arriving is not real. Maybe getting closer to that ever-changing destination is closer, or is reality, but no.

Arriving is not the reality. I still have massive insecurity. I think the difference is that I understand that having the insecure feelings is very normal. So I used to, the hustle, there was a daily newsletter, we also hosted these huge events. So I don't know if you ever spoke to one, but we'd have people like you, or we would have like the founders of the largest companies, startups like in the world. So I remember I was backstage one time and I was with Miguel, the guy who started WeWork. And back then we thought WeWork was-

He worked at American Apparel for a while. Yeah, and I thought, and he's a great guy. When I hung out with him, it sucks that he, it was weird. It was a really weird combo. But, and this was back then when we worked, I actually thought it was a $50 billion company. There was this woman who started Away, like the suitcase business, Casper Mattresses,

Casey Neistat was there one time. then like there was like another billionaire there. And I remember they were complaining. One guy who had a multi-billion dollar company, he was like, because what I would do is I would tell people you talk at one, you got to be here at 11 for soundcheck. There's no soundcheck at a conference. Like I just wanted to hang out with them backstage. So I would tell them you got to arrive two hours early and we would all be in this room about this size with couches and I wouldn't backstage. So I would tell them, you gotta arrive two hours early and we would all be in this room about this size

with couches and I wouldn't say shit, I would just listen. And I was like, dude, to hang out with all these ballers is awesome. And they all fucking complained. They all said- What did they complain about? One guy was like, and it wasn't bad complaining, but it was like, I gotta fire this person that has worked, but I've had to fire him for a year,

but I'm afraid of the confrontation. Or this other person was just in the New York Times for this $100 million raise and they're like, I don't know if we're going to figure this out. And it was just all a bunch of people complaining. And at that moment, it felt as though I had bad eyesight and I was able to put eyeglasses on where it's like, oh, it's awesome that I can be insecure and good at my job and succeed. And that made me feel so good.

I remember there was one guy named Sam Yagin. Sam Yagin started OKCupid, and then he was the CEO of Match. I think it's Match, it's a public traded company. And then there was Payall. Payall started a class pass. Okay. And I remember they were both so nervous to speak. We had like 3,000 people there.

And I was like, you guys have 3,000 people at your company, why are you nervous? And they were just really nervous. And I was like, hey, you want some water? And I remember Sam kind of snapped at me. And I was like, dude, have 3000 people at your company. Why are you nervous? And they were just really nervous. And I was like, hey, you want some water? And I remember Sam kind of snapped at me and I was like, dude, I'm here to help you. I'm gonna call me down. We got this, we can do this.

And I just remember feeling so relief, so much relief that these people who I admired so greatly were nervous to talk in front of people, were afraid of confrontation, felt insecure. And I remember like, so that moment and then selling and realizing I'm different. All of that stuff, I was like, it's so awesome and relieving that I can have insecurities, I can have flaws and still succeed and hit my goals or whatever. Insecurity

won't go away. way. so much to us and it would really Wondery Plus in Apple podcasts.