Ryan Holiday on The Economics of Book Writing, Why You’re Monetizing Your Media Business All Wrong, His Split with Tucker Max, and More

what what do you do with your money yeah yeah i know you got a ranch i think you literally he lives that forever that i mean that was like my house that so it's it's not like it wasn't like a hot like a luxury property or whatever like kanye having a ranch in wyoming you actually live there because you wanted to live there sam sam i think has some some similar aspirations but what do you are you like i'm investor you just do something boring with your money what do what do you do with well i spent a lot of it on this bookstore i i i bought two buildings in this in this small town of ba originally is gonna be a bookstore in a coffee shop now it's a bookstore and i rent out half of it to a a record store but i wanted i needed like a space to do all my stuff so up top is like my office my wife also wanted me to take all my books out of our house so that that was part of it it was like getting all the the shit out but no i don't really do anything i don't really do anything with it i invest it i'm i like investing in things that are very different than internet things so most of it's like in income producing how do you describe yourself you know i don't do it very well you you you nailed i i would sort of if i had to say what do i identify as i would say identify as a writer and then i i sort of have these other things that i do in that are somewhat related and somewhat unrelated but like if i had to sort of only pick one thing or like what what do i feel like i was like meant to do it's it's writing so i identify first as that sean do you remember this did i ever show you this coin i used to carry around i i would have it with me a lot particularly in the old san francisco office i had a coin you remember face of you no i've never never seen your coin what do you do two face of me no it was it said it say momentum worry say ryan yeah which means like you're you're gonna die you only live once right i i don't you love that sam carried around for years doesn't know what it says on momentous it's i knew that it meant like mobile momentum you have to live today like you're gonna die yes right and i was thinking about it i bought one for twenty six dollars and i was thinking about i was like this is the greatest business of all time i just bought a like a fake coin from ryan for twenty six dollars it cost them it was just probably a post like a stamp just to mail it to me so only fifty cents there's gonna not gonna be any returns there's no it's one size fits all and it made me happy and i carried it around and i i was like this is the is that the greatest business of all time selling coin it's it's been in it's been in a nice business better than the publishing business right like what's interesting about books is like like the the new book so you spend two years of your life writing something it's like sixty thousand words you have to you know the publishers taking the managing all of it so you know they're they're the middle man and all of it but like that book is twenty six dollars and people if if that book was thirty two dollars people would be upset because there's like a sense of what a book should be right like this is what people are willing to pick and what regardless of how good the book is or not it's exactly something of this shape i pay either nine dollars thirteen dollars or twenty six cents right and so what one of the things as as daily s which i started as this email list became sort of big if the idea was like okay are we gonna advertise are we gonna monetize this via advertising or are we gonna like is there stuff we can sell that you know makes it a business to pay for itself and as we were thinking about stuff you could do because i came from the apparel business before i was a writer i was like we are not doing t shirts under no circumstances are we doing t shirts first off because t shirts are like are you know it's kinda cheap you know but t shirts are the worst business you can do so like bands become popular people build a brand the first thing they always think is t shirts but what i remember is just how fucking complicated t shirts are first off because you have to get someone to make them but if you sell one t shirt that's already at a minimum three skews right small medium large if you wanna do extra large and and yeah extra small and now five skews and then you're like okay we're gonna do white then we're gonna do black so now you have ten skus right and it's in and then then they don't fit there's quality control issues all so i was like we're not doing shirts and also like shirts even though all of that people will only pay certain amount for sure because we don't value it as a thing so i was think i i was like i wanna make something that's better margins that's less work all of that so i was just really thinking about it and then one day i at the airport i at the austin airport and i was thinking about this idea of momentum mori which is like if you look in a lot of old like renaissance paintings the philosopher always has a skull on its on his desk and and so the there was a as a philosophical genre of like reminders of mortality and i was like it would be really cool to have a reminder of that what would that be i was like well i could get a tattoo and then i was like i don't really wanna get a tattoo and so i was what could i have and the idea of the coin popped into my head and it turned out to be really cool we actually use this mint in minnesota that invented the the alcoholic anonymous chip like that you get it like ten years or twenty years so they've been in business since eighteen eighty eight wow that's cool i think i think we're their biggest customer now and that's also is a really cool business that i've been fascinated with but yeah that was that was close i'm gonna i'm gonna ask you about the mix admit in a second because i have another minute admit that i think you're gonna go kick out of but do can you reveal how many of those coins we sell year or do not talk i i don't wanna say exactly how many but like ten tens of thousands it's a a lot of them and people like i'm giving a talk in marble falls next week and like they bought one for each of the attendees so it it also became it's a really cool way to like what i'm interested in is not like cha keys or like just random mass merchandise but like what our f is what our physical manifestations of the ideas that i talk about that could actually provide value in some way so like i have i have this this one on my desk but then the other one that i have this for my others this is this one says tempe fu which means time flies this is like a parenting one it's just a reminder that like to be present as a parent so i i kind of start with stuff that would be helpful to me and then if if it works for other people it's good i do think entrepreneurs tend to think about digital products first and not physical products that have good margins and this so that's been really cool well how much does the coin cost you a dollar more than that because more than that and then there's also packaging and all all that all that kind of stuff but but yeah it's i'll honestly it's it's a good it's a good margin but but yeah it's a good not as good as a digital product but good enough that business i feel like you know i have this phrase you you know you you are what you admire which is like if you admire things enough you you end up moving in that direction and that's a type of business that i've really like the thing the the little thing you just said gets like the highest amount of respect for me like okay elon can send a rocket to mars you know steve jobs can fucking you know where his turtleneck can do his thing but at entrepreneur who says well i wanted to create i really interested stoic so i created this free thing to give it away and i didn't know what the business would be the traditional model doesn't really work ads it would like you know how kinda of shitty would a stoic use newsletter be if it was just plastered with ads but i did it anyways betting on myself that i'll figure it out and then i figured it out first by having my little framework of like what's a thing that represents this belief that has high margins that has low headache that like i have a d business with over like three thousand skews so when you're saying that my body just like you know inside just s up and dying and i'm like oh wow what how amazing would it be if i had one sku that was just high margin and like i could just make that skew amazing so hearing you pull that off and you know the way it kind of like sam has it and people to conference by to me that's like you know top level respect because the creativity that that requires and the thoughtful that that requires is is kind of amazing i think most people would just kind of declare creative bankruptcy and say i don't know don't know how to figure it out and just never never this way i think shopify is gonna be like the biggest company in the world because they like let people do that do you what i mean like you you just come up with an idea and then you know it plugs into a third party warehouse although i have fulfillment center here in austin where i do some of the stuff out of the bookstore but just like that you can just come up with stuff and make it and sell it to people is it to me is gonna unlock like so much potential and part of the reason i'm able to have the books to like a physical space is that because most of what i sell online can subsidize like a in person retail also right sean have you heard of the the story is gonna come full circle not till the end have you heard of stuart res stuart res no alright have i bet you've heard oh i think i know this guy they own the pistachio company right yes so when you go to the store and juice or whatever yeah they own this it's a privately owned company it's probably one of the lot linda and stuart res it's probably one of the largest privately owned companies at america they do multi billions in revenue his he started like a security business that he's sold and you got some money and then now he owns palm one like the the drink palm drink he owns pistachio and a bunch of stuff anyway he one of his first businesses after he sold his security company made a little bit of money he bought this thing called the franklin mint and the franklin mint i knew i knew ryan i knew you're gonna know this was and the franklin mint basically started out by selling coins eventually they expanded to a bunch of other the collectible bowls but they started selling coins and up until somewhat recently they are one of the largest i think advertisers of digital and not digital print media and so like if you would open up a magazine like a usa like a like a tv and news guide like the got things they were always selling coins and it was franklin mint and he sold it for like two or three hundred million dollars when he was done with it and you know who bought it recently was ty lopez oh wow didn't he by radio shack also and a budget of shit he's bought so much shove hold on i'm i'm kinda stupid what these mint okay is the mint literally a coin factory so they take metal and then shape it into a coin of your choosing and then they they sell it or they they you know they provide it to to you who sells it is that the i do is a coin factory is that what a mint is yeah although the franklin admin mint is like comme quarters and dollars and stuff right but they but do they have they do like was like prince that no but yes they but they got actually sued because they use like a princess diana coin or they've done like like i don't know like something like famous person that like middle america moms like care about you can buy like a coin with their face interesting i've met this guy who has a very interesting path that like interacts with the silk road and other things and he had said something like he's like yeah what i'm doing now is i'm buying these email lists of like hundreds of millions of people like the you know like the leaked madison breed or whatever what it was not madison was it stop ashley madison yeah email list for like linkedin got hacked cool i'll take all those emails and like you can't you can't really even send to that big of a list it's like too dirty and you'll get like banned or whatever but he like had some like expertise and how to send mass emails and he i was like what are you gonna do with this like just start a new thing and he's like no i'm just gonna find people who like trump and gonna sell them coins i'm just sell coins and hats to trump fans and i was like i was like wow and he's like yeah like if point two percent of my list point o two percent of my list i've whatever ever converts like it all just make billions of dollars passively sending these emails i was like wow this is the the one of the craziest business plans i've ever there's an argument that fox news basically exists for the sake of like reverse mortgages gold coins and other forms of g like you if you watch fox news just the commercials you get a sense of like just how dumb the audience is to be perfectly honest and then you realize why the content it's almost as if like i heard this great thing about spam they were saying like like you know you get an email from like a nigerian scammer and you're like oh this is obviously spam that's because it's not for you right it's for someone who's dumb enough to to not be bothered by how all the red flags that are there and so well even even further it's they want people who after they get scammed won't really know how to like have course yes so they they won't be able to get back at you and so they they filter out all the people who have like lawyers yeah and so when you watch fox news and you get the sense oh this exists to create the kind of customer that would fall for these like obscene high margin almost criminal enterprises i know this is an exaggeration what but but like right on this side of what's legal or not businesses that tend to exploit not very smart or savvy people that's why the content is what it is is to set up the commercial break where people won't buy real things when you turn on pretty much any other form of entertainment you're not seeing those advertisers because right you're that's not who it's appealing it reminds me of in india i don't wanna do a deep dive on this at some point but there's like india has this culture of guru right so like in first in terms of gods we have like whatever fifty gods so the and then then the gods all have like they're guru and this the kind of like the saints type of people who give you know genuinely good advice but then they also kind of like do magic tricks and you're like to show that they're like you know you know the the the the man of god it's like he can produce something in his hand but it's like literally an illusion yeah like a magic trick but the way they work is they have this like vi virtue virtuous brand of being this person who only wears their white robe and they like don't have any material possessions whatever but when you go to visit them and people i mean there's like miles long lines like going wait like crawling up mountains literally they crawl to show their devotion to get to this person's like thing and you donate your gold chains you donate like gold and so these guys inevitably get raided by the government because they pay no taxes and they like you know are involved in crimes and they go they find like tons of gold literally like the physical the measurement tons of gold in their house and they have like and then they'll like license these like chip brands and like popcorn brands and stuff like that and it's like the face of this group but he's selling like you know potato chips dude to yoga vi yoga had ketchup up i think yeah it's crazy yeah no it's it's it's it's very strange once you get into sort of the back end of how some of this stuff works do you know anyone ryan who's out selling you in terms of coins it's selling more coins no i mean i do sometimes was wondering like when when when we order like we'll order like you know a bunch of the coins from the from the mint which is in minneapolis and they'll be like oh no we're really backed up like sorry your order will be like in a couple weeks or whatever and i'm always like who is in who is ahead of me but but there there is i mean so so i was thinking about it like i was thinking like okay wanted a reminder of momentum mori and then i thought coin and and i it didn't occur to me because i had a bunch of them already so i was probably a but there is a a genre of there's a a thing called a challenge coin that like the military gives out or police officers give out or firefighters give out sometimes it's like a comme like you visited this place but like if you did like you know this tour of duty and operation enduring freedom or whatever like they'll they'll often give you challenge so i think a lot of them are like government clients or like you know profits or there there's like that but like i could get them done like we're talking about margins they would be much cheaper for me to make them in in large bulk like from china but but we haven't done that we've always used this this original place wanted to do made in usa but then and then as it happened during the pandemic it was great because it was like we never ran out of stock of any of our products because everything we sell is made in us that's awesome no brian i wanted to ask you because you've done a bunch of different things okay so you're a your college dropout correct you you worked for tucker max and you consulted with tucker max robert greene who's the kind of forty eight laws power or whatever you've written a bunch of books you've you own a independent books shop you got your coin business you sell courses on that you've done a bunch of different things okay so i wanted to play a little game just to get to know you game and and it's called first worst best best last week okay and basically it's job okay so what was the first job and does be like a job it could be like a side hustle you had so what's was the first kinda dollar you earn i worked at it i worked at a deli at a grocery store called obi in in home california right on lake tahoe and what were you doing at the like making sandwiches and i worked in the stuff like just like a like a just a kid i was fifth fifteen fifteen fifteen sixty yeah fifteen but you know just like six dollars an hour whatever minimum wage was in california then just a you know kid who worked at a little little small town grocery and what what was it like because you you can make six dollars an hour i don't know how many hours you're working but you end up with like you know couple hundred bucks after you know a couple weeks that's a lot of money to a kid do you remember like what you did with the money or how you felt about that that amount of money at that time you know what i don't remember what i i was super in a snowboarding so i probably bought a snow order or something but yeah i it occurred me the other i was just thinking about this that i basically worked nonstop since i was fifteen years old like that i worked at i worked at wendy's after that if i remember correctly that was a lifeguard card so i've had like a brazilian jobs but that was that was the first one and then like i feel like at age like eighteen or nineteen or something stupid you're like the boss of american apparel or something like just like something ridiculous or like at eighteen you like worked for robert greene riding forty eight laws of power well forty eight laws power came out when i was like eleven years old but so not not exactly but i did i started working for robert when i was twenty and then i was the director marketing in american apparel like in my in my early twenties so so you when you dropped out you dropped out because what you just hated to school or you had something you wanted to no i liked school but i wanted to be a writer and so i i had this i was going to use riverside so i was i was working for tucker who was at that point one of the first bloggers to to have a book deal so i was like i was working for him doing like marketing and online stuff and then he got me a job at a talent agency where i did like yee i could see you fitting up that yeah i was look answering phones and stuff but i worked on like new media like so this is right like youtube it just sold so everyone's sort of interested in internet talent so that's what i was working on and then this summer i was at the end of that summer that i was working there i was supposed to go back it's a college and within one week i got an offer to to stay on at the talent agency to to i was working with this movie producer there to be his assistant and then i've met robert greene and robert greene needed a research assistant on a book he was writing called the fiftieth law and so why did all these people like you why did tucker hire you when you're eight team what did you what did you do to get hired by him because at the time he's writing basically like funny dating stories and sex stories right like that was like his blog at the time of if i remember correctly i think i was very young very ambitious very hardworking working and i was just obsessed with the internet like what what this sort of internet culture would become and i loved books like i just i've always loved books and so i i think they sense that i wanted to be a writer and case sir i sort of went under their wing as like an apprentice in you know how how to do how to do what they did did you just cold email number so when i i met tucker because i was writing for the college newspaper and i wrote an article about him which is what i was doing and i would write articles about people in the way that now you'd be like go i wanna meet this person noah will you come on my podcast right yeah but but this is before pocket so i would just interview people and write articles about them so that's how i met tucker i was a huge robert green fence so i met robert through through tucker and then the talent agency the guy who i worked for was producing a movie about tucker book first book so they're all sort of connected and then it was through robert greene that i met dove charlie who was the director or it was the founder of american apparel so it all kind of was all swirling about each other and what was the first kinda of like personal hustle did right you're helping and tucker achieve his goals you're helping robert greene and achieve his goals you're helping the talent you find talent when did ryan go into business for ryan that's a good question i don't know what like the first thing i would have i mean i started my marketing company in two thousand eleven when i was writing my first book but i think the the first big bet i made on myself was i mean i i've done other like little stuff before but the first big i in two thousand eleven i basically quit at american apparel to go write what was my first book trust me line so that was like the first big bet on myself and that was a hit i mean that was that was pretty it it seemed like it took off another it got a ton it i sold it for a good chunk of money for for at least to me then it got a ton of attention it ironically it will it sold well but it will earn it will probably earn out its advance by this summer which will be the tenth anniversary of it like by the the the i'm it's looking like the the royalty statement i will get in july of twenty twenty two which would be the ten year anniversary of the book it will finally go from from negative to positive on the advanced statement what was your advantage i was two fifth it two fifty i was it was two hundred with some incentives although when i announced it i announced that it had been sold for five hundred thousand dollars because i know i knew people did nobody actually fact checks press releases so trust me yeah so so the whole point the book was to prove that like the problems i was talking about in the in the media system in the book were real so i i promptly doubled the advance when i announced it and and nobody nobody checked that's funny did you so you got a big advance do you didn't have that big of a following at that time how did you fin angle us any advance at alone like a quarter million dollar advance your first so the bet on myself was that i i left and i wrote the book first almost all non fiction is sold with a proposal and then you go write the book but i didn't i didn't necessarily need to do that so i wrote the book so i had what was like i had a i had a it's like i had a good piece of property like i i wrote something yeah that was like unlike all the other books at that time that and i don't think really there's been that many books like it or that i would maybe chaos monkeys would be another like similar book that i i'd sort of which i thought was good but but so i sold it that way so i i wrote it so then i had it but it was mostly just all the authors that i knew i had sort of got in because i i'd worked for tucker i'd worked for robert i'd worked for tim ferris at that point so had a pretty good sort of role decks of people who got me in the door when i when i sold that book are you still doing the deals now those type of deals now with all your latest books or are you self published i'm still at the same publisher actually i've done all my books with the same publisher i've self published a children's book and then i've self published two high end editions of traditionally published books that i have like i have a leather edition of the daily stoic and the obstacles is the way but other than that everything's been traditionally published i guess i own the audio rights do i connect just like from the outside you know i think a lot of entrepreneurs feel this way it's like oh publishing you know record labels and book publishers it's all just middle and they're they take advantage and the authors see so little to you know blah blah and someone like you you have a a lot of business sense b yeah now have a track record c you have a independent audience you could sell to so there must be some reason that you say no actually people don't get it that you do wanna publish it for these reasons why at it on a a case by case basis you're just you're really doing the math will will the what they're paying for it plus the royalty what what are you thinking you earn you know in a short amount of of time or or you know in a certain amount of time so i i just do the math on each project so every time i think about a book just because i have a publisher if obviously if no one one's was interested in publishing it there be a different story but i i you know i conceive of what the book is and then i take it out my publisher has a first look deal at my books i and i see what you know what they what they think what they're willing to pay and then you know i an agent and so we obviously try to get that number up as high as possible and then once i have that number then i think okay what would this look like if i did it myself so what would it cost me to do it myself what am i likely to sell myself how much work is that gonna be how much of a distraction is that gonna be and ninety percent of the time you know the math the math tends to go towards traditional publishing in my experience the the kid's book that i did the publisher just wasn't wasn't in wife wasn't in their wheelhouse they didn't totally get the project but so i did it myself it's been great and really fun and artistic fulfilling but also just an incredible amount of work i mean like the coins i sell directly from my store right the manufacturer makes them they drop it off at the warehouse they get shipped fulfilling books through amazon is like in an like and then also the thousand independent retailers in the united states plus every international edition you know is extraordinarily logistically difficult and i remember you you gave this talk one time that was awesome where you showed a chart of the sales of your book versus the normal book so normal book you get a peak and then it pretty much just kinda goes away but then for some of the classics you get a peek and then it goes down a little bit but then it kinda quickly comes up to the point the word even like it's pretty steady throughout like a catcher in the rye or something like that or even sometimes it'll it'll it'll suck early on and it just slowly get better your books if i remember correctly they they popped just like everyone else they went down a little bit just like everyone else but then they like raised and were pretty steady with daily sales and you're like that's because i make shit that can last a long time and this was actually for when you're running perennial seller i think you're like proving this point is is is that still the case and considering all of your other businesses is book is making books still where you make the majority of your income or you're just using that because you love it and it happens to make money and you go but you make the bulk of your money from other shares right it's a most non fiction authors make more money from speaking than from books that's because speaking can be more lucrative but it's also because most authors don't sell very many books right so i i'm in an unusual space where my books do sell consistently and i have a lot of them so i i make a good living from that but probably make more money from stuff other than books than books all all in dude that's crazy that that you're like the man and yet still it's like the well that that's like that's another reason to traditionally published right so so like you your a publisher does not take any percentage of speaking does not take any film or tv adaptations does not take any ancillary products any merchandising anything like that so really this the book is it's not a loss leader because people pay for books and and and books have value to people but like the the the ideas in the book everything else is downstream from whether that that takes hold or not does that make sense so if the book doesn't land all the other stuff you know doesn't really matter but if the book works all the other stuff happens and then the success of the book is slightly less less significant i think what my so so in publishing there's the front list and the back list front list is anything within one year that like the year of release that's considered a front list title and then it becomes a back list title after a year so most titles stop selling when they leave the back list at when they leave the front list and become on the back list but almost all of the income in publishing is from the back list so so for me it's about like i'm i've tried to create that in my own my own catalog of like titles that sell every year as opposed to like a big book that comes out gets a lot of attention then then three four years later i have to write another new book because the other one is like not relevant anymore it's like it's like michael bub a or or mariah carey running a christmas song you know you you want that christmas hit you want that at a new yeah i mean so so like my book the daily stoic when when when my agent was like we should do a page you you should do a page today about doses and i was like i don't know and he was like it will be your best selling book and i was like there's no way that doesn't make any sense he's like yes it will every new like it will and he's right it the book sold more copies this already this january than last january amazing what what do you do with your money yeah yeah know you got a ranch i think you live he he lives that forever that i mean that was like my house that so it's it's not like it wasn't like a hot like a luxury property or whatever like kanye having a ranch in wyoming you actually live there because you wanted to live there sam sam i think has some some similar aspirations but what do you are you like i'm investor you just do something boring with your money what do what do you do well i i spent a lot of it on this bookstore i i i bought two buildings in this in this small town of ba originally was gonna be a bookstore in a coffee shop now it's a bookstore and i rent out half of it to a a record store but i wanted i needed like a space to do all my stuff so up top is like my office my wife also wanted me to take all my books out of our house so that that was part of it was like getting all the the shit out but no i don't really do anything i don't really do anything it i invest it i'm i like investing in things that are very different than internet things so most of it's like in income producing real estate in which state texas and florida and you're just buying like what like multi family some multi family i have saw mostly single single family and then some like vacation rentals and you have a manager who what do you are you hands on with that is a headache for you yeah i try i i mean i try to have it be as little headache as possible most of them are managed by yeah property managers but but i like it's not that i think the the stuff that i do will go away but i like the idea of like like my decision to write trust me lying and not having to think about needing to sell it upfront there was a similar one when after i wrote trust me i'm lying i was like hey for you know for my next book i wanna do this book about ancient philosophy and they were like are you pretty sure you know like they so they gave me less than half i got seventy five thousand dollars for the obstacles as the way which is sold you know many many times more copies than trust me online and you know obviously set up all all these other things but when they came back with that offer i was like okay sure whatever you know it it wasn't i didn't have to think about whether i could live on seventy five thousand dollars for however long it took me to write the book because my life wasn't set up around needing that's that's really like when people hear a book advance it can sound like a lot of money like even you know two hundred thousand dollars trust me in i'm line so it's just like a salary right for two years but even worse than that right so i let's say i left my job and then eighteen months later the book came out from from like when i left so you two hundred thousand dollars over eighteen months that's that's pretty good but like i said it hasn't earned another dollar for ten years so so over eleven and a half years two hundred thousand dollars is not is not great but i really i wanted that's the book i wanted to write and obviously it opened up other business opportunities but i like to be able to do my creative work and not have to think about does it make sense in the dollar and instead and this is this is how the entertainment business works as well like almost all the money is in the catalog in owning the intellectual property over the long term but you can't do that if you are dependent like you get paid as an author every six months so and you're getting paid for the previous six months of earnings not like okay ended yesterday here's your thing you're you're getting essentially a paid from a year ago and so that's like you know that's a you can be living hand to mouth that way even if you're a very well known person who's in you know the media all the time and so i i wanna be in a position where that's not the case sean do you remember like have been maybe two thousand and fourteen i think basically when when you and i were just gonna to know each other there was this article that went viral and it said you can buy ghost town in california for like one point two million dollars do you remember that like like you could buy like old mining ghost town yeah and people did a group did it right and i think yeah i saw your hey and ryan was involved in that i think ryan and his ryan so ryan correct me if i'm wrong you i've never met the other my my best buddy yeah oh really okay so listen to this shot okay so devil is good friends at brent so i've heard all about them if you go on youtube sean and you type in like ghost town brent you'll see this channel where this guy named brent he's this really cool dude who's got like one point five million subscribers on youtube he started living in this ghost town that he bought a while ago but just when the covid when pandemic hit he just moved there and it it went to the moon and it's the best youtube channel i'll watch anyway ryan weren't you like the you and brent were like the my the brains behind it you were just kind of the quiet i was one i was one of the investors there's there's a bunch of investors i think we know you probably know like half of them this point or more more than half but i to be perfectly honest i thought it was a terrible idea i was like you're you're gonna save all your money this is not gonna work but i mean i've known brent for so long i i just sort of was like one of the small token investors but i and i didn't see it becoming what it was becoming i i should have like i was thinking about it in terms of real estate because brett and i have invested in in in real estate in austin before and so i was thinking about it in real estate and you know being from california was like that area is like a like a pit you know anyways i didn't think about it as a content play and that's obviously what what it old ultimately probably will become i mean you could make more money off the youtube channel than the actual any money you can make off just turning it into a hotel that's one of the things i found with the bookstore and that's kinda where where the the it clicked for me was realizing that so opening the bookstore that like that making money from selling books might be the third or fourth like least important revenue stream or or use of the property like the office being number one the space to film and make stuff like content being number two and then like real estate being number three and then you know like the actual brick and mortar retail business being like four or five that's amazing so you basically are like you bought a set the set actually just kinda functions it's like but mean it's like the okay coffee it's like three hundred acres in the middle of mountains yeah have you seen it sean no no don't talk about the book but it's the same thing though i mean the the the ghost down is an enormous set it's a set piece to film and create content and have coffee a a life and a brand that people care about you know and so so hold on so it's been many years now so what's actually what is that today is there i don't watch the youtube channel is there like a functioning town do people can visit what the pandemic obviously made hospitality business you know not very viable so right now it's it's mostly just in the sort of rebuilding phase they're like rehab all these different cabins and then he films you know if someone's videos there and they do like merchandise and stuff like that it's really but like my son like my son is five he watches one of those videos every night before bed he's like obsessed with it it's beautiful it's like a beautiful youtube channel it's and brent is very end it's awesome and it's i mean it's crazy that the quality of stuff you can make a one person can make with like a drone a gopro and like you know one decent like sony camera like you can i mean he's he he was a one point putting out like a forty five minute video a week like he was putting like a television quality show out for millions of people you know for like a couple thousand dollars a a month that's crazy what you can do anyway it went from like zero to like one point five or one point i forget exactly over a million subscribers in like eighteen months yeah i mean you got tons of media attention it's done like hundreds of millions of views i'm very bullish on youtube as a social there i'm like late to youtube ironically considering that's like what i left school to focus on like i i saw at this down agency i signed their first youtube client and i remember this agent coming up to me and he's like what are you gonna do you're gonna commission their advertising revenue and i was like i guess yeah and like that's like of course that that's way better than commissioning checks from you know a television series because you this what you actually own own the stuff but i've seen it even with with daily s like like as an author you get recognized like every everyone once in a while it's actually been weird for me in the pandemic because like i haven't done that much stuff and so every time i if i go out or i do something like i was i i saw someone in austin a couple weeks ago and then i was was just in new orleans and like because of youtube and and like instagram reels like the amount of like fans i see in person it's like exponentially different than what i was getting from like who i was i see you want tiktok like every day you're in my tiktok feed every day oh well i'm sorry to hear that telling me to like you know think marcus aurelius said yeah the yeah telling me something's of ancient dude to you know said about you know remembering i'm gonna die or like you know not not being anxious about the future and i'm like yeah actually this guy's talking some sense so i like it and in this in the the video quality is is really good like i don't know if you're i don't know what you're doing for that but like it's like a gopro a gopro nine hero it costs six hundred dollars and you can shoot in four k video with a it doesn't even have an external mic it's like it's crazy what you can do but you could do a four k video on your iphone but when i upload on four k my i shit never looks like go i think the gopro corrects but i don't know the gopro does incredible the the lighting in the building i had to say not something i control is is quite good it looks like you're on like a farm and you're leaning on the like you're in the middle of the you're like in the middle wall i mean the gopro are better for outside stuff but yeah you just i mean you just put it there and it shoots like you know super high quality stuff and then somebody cuts it up do you edit you just hand that off to somebody's i i shoot for a week and then i i try to shoot i try to think about what i want them to make when i'm shooting in and sometimes i'll give notes i'll be like okay you know cut this here or whatever but i'm mostly yeah i'm mostly just shoot in like small blocks and then the idea is like okay so if i'm shooting in a in you know between thirty and one minute thirty second and one minute chunks okay so that goes a content of that size can go on twitter instagram as a real can be a facebook video and it can be tiktok so you've got like four shot four bytes at the apple there then that content can be packaged together to make videos on on youtube so i'll take like eight of those and that can become an eight minute youtube video and so so by shooting like these little things i get like lots of different like platforms that they can go out on so basically well so ryan i i had i i made a living with a daily email sean sean just released this new business that he's working on which is amazing sean i gotta reply of your email it's called the milk road it's pretty hilarious and it's like a a bit a crypto daily email that he's working on with his partner ben but you have the daily stoic which is awesome but you have this new ish thing that seems to be like working out really well and honestly i think could be one your bigger businesses i also think it could be bigger because you could sell it because it's not exactly like the ryan show but it's called the daily dad do two daily emails slash podcast daily dad and daily joke who's who's writing all the daily data i write them moment i write daily dad and daily s what how big that business or how big is the email daily dad is like sixty thousand people i think it's weirdly not as big as i want and not just wanted it to be but i actually thought it would grow faster than daily s did and it's actually been a little bit slower but how big still daily s a hundred oh my god yeah really holy shit do you advertise to grow or what are you're just through content then you capture you you make videos i make content social drives a lot of the sign ups and then the the book i mean the books sold you know well over a million copies but yeah so i i write both of them and then it's it's mostly organic but i'm trying to i'm having to get more serious about sort of i think some of the low hanging fruits probably been picked so i'm having to start to think more seriously about it as a as a business not just to content that i make man you you you oh my god you're killing me why weren't you advertising like three or four years ago it was so much cheaper you could go acquire an email for a dollar fifty now it's like five six seven dollars i i should've have asked you so you you're hanging out with people all the time that are you know super successful know bunch of people who know you and i think you're respected in the kind of like the business world and entrepreneurial world but i feel like the matthew mc mckenna hay world i feel you you are pretty grounded and you're i don't get the vibe from you that i get from a lot of people i hang out with which is just like more more not enough i'm not there yet i gotta go bigger or bigger and and really is just kinda like i haven't succeeded enough yet i haven't earned enough yet i want more money more success and i don't get that vibe from you are you just hiding it or is that the case i mean i definitely have there's definitely a part of me that's in that i mean i've written twelve books in ten years if i was just like oh i'm good you know like clearly there's a drive there or even some might say a comp i think so so there's a part it but i i have so i've been with my wife since we since i was twenty so we met like right as all this stuff is happening and so and then i i have kids five years ago so i've always been a little bit more of like a normal person i don't mean that in like fucked way but i haven't been like oh i'm a digital no or like you know i'm i'm gonna go live in puerto rico for two years like know like i've been more of just like a regular like i don't wanna say a nine to five person but like i've just been like more rooted in like regular people life than i think a lot of like creative entrepreneurial people i know who i tend to find her a bit more like chaotic it sounds judgmental but just it's a different lifestyle and so i think that's i think that's a part of it no i i know what you mean like for example right now a whole bunch of my friends are either you know like you say they're crypto rich moving puerto rico i don't pay taxes they're going to miami because i heard the actions there right now doing this doing that and i'm just like but you know like i just got gotta i have two little babies and i'm like what the idea of moving like i mean the idea of like getting the kids into the car to go to the park is like overwhelming let alone like uproot my life in some way in any way taking like massive risks now just is not like appealing to me in the same way well like when i was twenty four i remember i moved i picked up i moved to silicon valley i didn't know what i was gonna do but i was like this is where the action so i'm just gonna move to silicon valley and then i ended up getting this job working with this like billionaire dude and the office he had this dope office and i remember i slept in the office like two hundred thirty two days out of the three hundred sixty five days and i was just loving it i wasn't like i was being forced nobody's forced before the the office had an apartment right i don't know it was like it was like it was like it had like two million dollars of the furniture it was a love it was a billionaire a better imagine peter till office yeah i wasn't sleeping in the garage like the bathroom floor was heated in the morning so your feet weren't your toes weren't cold so you know it wasn't super rough but nonetheless i basically was choosing to ob obsessed and like go all in in a way i was like excited about that and been able to do it in a way that i couldn't as real life stuff layered on like relation chip kids and things like i remember when club house blew up like a couple months ago or six i was like what like i i was like i don't even wanna go to a real conference let alone be in like an internet room conference like i it was just totally inc to me that anyone would wanna do it have the time to do it it that's so that's sort of not been i i actually like writing you know what mean so the other part of it is is not just like the sort of wanting to have more of a normal sort of rooted life although i feel like i do weird unusual i i take risk in other ways like letting know this farm and stuff but it was also like for me like i i writing to me as a calling that's a little bit different than i don't know making money in crypto or something like it it's it's a blessing and a curse right it's a blessing in that it's fulfilling it gives you purpose it's artistic it's like a thing you master there's also i think a ceiling on it you know and and like you can you can be good at it there's obviously the jk k rallies of the world but like you know but but there's not a ceiling to being famous i mean you know we're both friends with tim ferris and like his fame allowed him don't know what he's worth but he's probably worth hundreds of millions of dollars because of his investment yeah i mean there the there's not a ceiling on being well known in getting access to no but i mean you sort of you end up in different niches right if you if you're called to be a poet you know obviously it'd be more lucrative to write business books but like you are where you are you know there's a certain amount of like you don't choose what muse visit you i know that sounds a little mystical but like you i like sometimes people have been like oh he's writing about stoic to get rich which i always laugh at because like again i if i if being rich was what was motivating to me i would do literally anything but this right like this is the worst possible of the things to affect but i i guess my my thing is like i i really like the routine and the ritual of sitting down to right which is also i think inherently a bit grounding in a way that like some of these other pursuits maybe aren't what is your normal workday look like i mean are are you doing like a nine to five no nine to five like i wake up early i go for a run or walk with the kids whether we're at my farmer or my place in in town i don't check my phone in the morning i don't eat in the morning i usually journal in the morning and then i go i write usually for two or three hours and then the rest of the day after that is business other work stuff and i'm i'm done by four almost every day so i probably work eight thirty to four seems like a good ass i like it i try to i but i i like it's import there are also i i don't know to me being really great at what you do and somehow managing to be like a somewhat normal person to me is actually like a rare thing to do than to to just be great at what you like i think if anyone decided to be like tom brady is tom brady but there's a cost to being in tom brady but like if you choose to be that singular dedicated to what you do it's easier to be better at what you do than to say like i'm gonna work nine to five and be like great at what i do if that makes sense so you used to work for tucker max you then became buddies with them and you had a a a business together but i've never asked either of you about this you've probably it's based off of some of the stance i know that you've seen you've written some great stuff about like a letter to your dad about voting for trump i know that you're against like a some a lot of these statues and you've donated money to that and tucker i think has gone the other way where no i wouldn't i wanna call it the opposite because of course he's probably against a lot of things or four a lot of things you are but maybe different and he actually recently came out this article that sean and i talked about it's called doom day optimism and it's about how very bluntly but he's such a good writer that like everything he writes it seems like convincing but basically he talks about how he thinks like the american government is basically gonna collapse in two to four years and how he's preparing for doom day and it was like crazy fascinating but i what is your opinion on that i i've been eager to ask you what you think about that and what if you have an opinion on it tucker was very good to me early in my career and set me up for the success that i've had so i i feel very grateful for that in a lot of ways he and i live in very different realities now i think i don't know exactly what caused that or or what what the driving force of that is i mean i have some theories but a lot of that stuff that i see in read i think it probably has nothing to do with whatever he's talking about it's it strikes me as as driven by driven by something else which i've seen a lot of like i think the pandemic brought it out in a lot of people they're probably so we both know but i've noticed a kind of a radical rationalization or an un ent from people that otherwise i would have assumed we're in in alignment on i've just noticed an un ent that i don't i don't know where it's going but it it certainly worries me is that a diplomatic answer yeah and i don't really like that answer because i understand what you're trying to do i i i think you could you could not agree with his opinion and still be respectful towards them but i understand that you're trying to like keep it you know be cool but like in one regards i could be like well i i i i actually could see ryan they almost something similar because he lives in the country and he likes privacy and like he you know you're like so so high iq that high iq people typically are like quirky and have like weird opinions but then on the other side i know like some of the things that you stand for and i could see you just laughing on that being like what are you ridiculous yeah but it's it's in it's it's weird i i've noticed this sort of trend in like sort of tech entrepreneurial people where had almost say fad but it it's almost like these idea viruses sort of enter the community and some people end up taking them to like very strange extremes so like poly was won a few years ago and then crypto is one i i i i've i like i'm not anti crypto i i've i i i think there's a lot in crypto i've i'm invested in it too but then then it then in the pandemic there was like then there was this sort of anti va anti lockdown anti like covid denial that was one and then i'm i'm very alarmed by some of the people that i know in that space that are now going in sort of like a it's it's worse than a trump direction it's more of like a january sixth like end of the like a like a toxic like we gotta buy guns and i have guns but there there's this like almost like like doom day like disaster c direction that it's going in and i i don't it strikes me as coming from somewhere other than like what they're actually say it's coming the past does that makes sense and by that do you mean the belief is coming from some other like kind of reasons or the motives meaning like like money yeah like if we perpetuate this we'll get more notoriety we'll get more money we'll get more attention like you know there's some people like clickbait is in general is that right like i may not believe this like if you watch a sports talk show yeah on espn they don't necessarily think that lebron james is better than michael jordan but they know if they say it it gets clipped and it gets shared and so there's like this yeah i i do i i perform versus like do you think that the belief has come from somewhere or the motive might be driving them to dream in a radical i think both those things so i think number one all these people are are very smart right and so if you've built your whole career being smart and being a contra it can put you in an uncomfortable position where you're like dream rejecting things that make sense because that's instinctively where you go like this is what happened with with with dove at american apparel his whole everything he did was fucking insane i'm gonna start a usa apparel company i'm not gonna use professional models i'm gonna pay a living wage none of that makes any sense that was all those individually are very bad ideas but he somehow built a billion dollar company out of it so then when people were like you need to hire a professional operator inside you know you need to hire a real cfo and a real cmo and all this stuff he was like no right so we just got used to rejecting everyone's advice and it it it led to this downward spiral so i think that there's a little bit of that i think there's i think there is this sort of as people become like i think there's you know what audience capture is where you sort of get used to telling the audience what they wanna hear and so the algorithm is very deductible it tends to reward like obviously controversial things it rewards you know polarizing things and so i think what happens as certain people's relevance slips they are more prone to the it's like you know you're always putting stuff out and if what you've put out in the world hasn't been working and then suddenly you like you chance upon something as as compelling as like anti va or this or that that then it if you it's like you're getting it's like a a blast from the past you're like fuck this is it right so i think they're i think there's some of that that that's taking that spiraling people i also think just the pandemic fucks with people said it's it's been a lot like like we're not meant to live like this i think it's that the other thing like in in like a joe rogan or some of the intellectual dark web people i'm also noticing i just like when you've been very mistreated by like say the media or just like elite culture it's very hard for you to agree with those people even when they're right so you end up going back to the contra you end up like going against things that ordinarily you wouldn't agree you would totally agree with but from a tribal perspective you know you you it's imagine if trump had gotten reelected like how many liberals would have trouble with the vaccine because you would have to then agree with a trump thing i think i think we're seeing that i think this is why in a lot of men who have been sort of not media darling are going towards some of the direction of things we're talking about it's just a sort of like i'll die before i agree with those people on anything right there's a there's a chart i saw was amazing it was in a it was in a crypto annual report and said yeah what is what are some of the underlying things that drive this like crypto was like a religion it's like a cult it's like you this very very strong it's not just the same as like i like this business i i'm gonna invest in this asset you know people don't feel the same way about bitcoin as they do you know a piece of property in dallas and so it's a it was this chart and the chart basically was on the on the on the y axis it was like do you believe it was about institutions it goes do you believe that institutions are like credible or not credible meaning like are they honest or are dishonest it was i think the way they put it and then on the other side was are they competent or incompetent it's like rank these institutions i was like the us government it's like dishonest not not competent incompetent and then it was the cdc and it's and it showed how they've been moving over time and basically every institution that you could think of whether it's universities whether it's the health organizations the nih and who and and cdc whether it's the us government they are all sort of traveling towards dishonest and incompetent as the general public viewpoint of them and this has a bunch of implications is like well so peep so the things that reject institutional beliefs so you see joe rogan just explode and pop you know he's bigger his show is bigger than quote unquote mainstream media he is more mainstream than mainstream media but his brand is not an institution and he doesn't look like them doesn't read off a tele helicopter and so he's got this like appearance of higher honesty higher competency and so the same thing is true with crypto which is non government money blah a lot and so all these things are like on trend right now and that doesn't necessarily make them more honest and competent but it is the perception that's yeah and i when i was listing the different things the other one i put in there is i think like psychedelics is another one where it just becomes like this idea of virus and i'm not saying that i have a disagreement about it i'm just it's very interesting how these things just sort of infect these different subgroups and become almost a new it's their identity is primarily in that the the map the it's like you it's very tempting to fall within where you're smarter or better than other people that sort of outsider mentality and so i think i'm just i'm very wary of how that's affected people that i know and i'm worried it's taking some of the more fragile people into a dark potentially dangerous direction where they're just they're fucking with things that once you fuck it they're very difficult to un fuck and speaking of of psychedelics dogs and we'll wrap up in a second here i saw i follow so we've talked about aubrey marcus on the podcast because aubrey has a crazy story because his dad like invented like the flashlight and then he like kinda par that into building this awesome supplement empire but i got this instagram ad or maybe i just saw on his page so sean i know if you saw this aubrey marcus the guy we talked about yeah he has this this documentary where somewhat recently he spent i think seven days in complete darkness like and and i heard maybe he was in ce go am i getting into the details no definitely not at ce go oh i know he has ransom not corona maybe it was there oh okay well for some reason i thought i was a yours okay i'm wrong then but didn't did am i right though and that it was like five or three or seven like multiple days it complete pitch i don't i have i've not heard of about that but i am oh man i like i like aubrey alive no aubrey a long time but he's i i'm i'm a little worried about him he he's a wild man sean you didn't see this so me why did he be this i so basically he had a a night vision camera looking at him and he was in a small room with a bed and basically pitch dark and after twenty four hours or something like that he kinda starts hall and kinda goes crazy and he's talking to himself and the whole documentary is is basically showing the night vision camera of him talking to himself and then like a voiceover over in some flashbacks of him talking like what he was experiencing to that point and he was trying to go through like almost a psychedelic experience because i guess there's something where i i don't know the science behind where you're in the dark for a long time you start going nutty and have some realizations i don't know if it's sure or not but it was fucking insane it was crazy i mean it the way that i see it is like to me it's like it i don't care if i'm an outdoors if i see a huge epic mountain i'm gonna be in awe and that's how i was with aubrey marcus this documentary i'm like i don't care about drugs i don't care about this guy you just saw your head i just saw i i i watched parts of it i started watching parts of it because he released like five minutes at a time on his instagram i started watching parts of it he is it's the fucking craziest thing like i've ever seen the guy's insane you have to watch this shit it is just did you come out okay the other side or you haven't gotten to the end well this was filmed like a year ago like instagram so so we we assume it all worked out well the reason i didn't buy it is it i'm afraid i'm kinda afraid to watch it but like he's wild man because i watch his instagram and i see some of shit he does and i'm like this is i'm just i'm very guys i'm very concerned that these people are messing with their brain chemistry in a way that it's hard to come back from and you know i i i am i am not a fan of this sort of like a prescribed medicine for yourself to heal unnamed traumas like i i i don't i think it's gonna end very badly i'm maybe i'm a little conservative and i'm missing out on something but i i don't think you should fuck with your brain the way some of these people are fucking with their brains and i i think it's gonna i think we're are we're starting to see some of the ramifications of it with some of the stuff we're talking about here but i i think this is hard to put back in the bottle yeah this is this is wild this is i are you looking it up yeah i'm reading about it right now what does it say is it seven days it was like days so like okay there's a part of this i can get behind which is like you know people whether they go try to climb out everest or wim hof getting in a cold cold bath every day to like you know challenge themselves to like like it's say you know there's a form of meditation for a example so he said my thinking was this if the prospect of sitting in the dark with just your own thoughts frighten you maybe that's exactly where you need to be oh my god and oh rattle stay scare too i don't need to get a bit by rattle thing and so oh on it for me there's a part of this that i actually like i get part of that which is like i think the more comfortable you could be with yourself and buy yourself and not need stimulation not need others not need constant entertainment i do think that that is like a direction personally that i would like to go in where i can i can be at peace and happiness without something going on now in this and this one i think is less it to me it's less scary than like being like yeah i'm gonna start micro dosing lsd or like i'm gonna go on this ayahuasca trip in the fucking forest because i heard joe rogan say that it was transformational to me that's like way higher risk and maybe not necessary compared to you know i guess the darkness thing is a little bit less permanent feeling for me but and is it that's what they do also just justification to like break them i i don't think it's something you wanna be messing but again yeah maybe it is like deeply traumatic i'm not sure hey you know what the phrase is whatever doesn't it kill you makes you weaker seriously man i don't i don't know i whatever it doesn't kill you fucks you up really bad i always read these to me these are like these are content stunt right this is no different than jackass and and a bunch of other things like maybe some people come from a good place and i'm just kinda skeptical about all the stuff like for i'll give you brian i'll get make it personal for you which is like i saw the daily stoke was like oh that's smart stoic is this growing trend he probably likes stoic but like you can like it without having to do all the work of creating a daily email and content around it like that is the opportunistic side of this like kind of cool niche thing that's clearly growing and i said i don't know you right so i'm just thinking from a farm i'm thinking oh that's smart and you know he probably recognized this growth and said okay i could build a cool brand around this thing that i like and i see is growing and so when i see and you know so for example if i see you make it i tiktok every everyday about stoic i think to myself well you know i don't know how much of that is like well this content is gonna work so i'm gonna do it versus i really just needed to get this off my heart and share this with the world so similarly when i see you know these stunt i think to myself well they know this is content that's gonna hit and they can get a bunch of attention from it and like did he really need to do this and want to do this i'm not sure right those motivations get mixed i know for myself they get mixed because you know if i i've had a bunch of tweets go viral i you know i added two hundred thousand twitter followers last year is very addictive and in i don't know if you saw his the the the stand up a special that that husband is doing right but did you see him when he was in austin he has this part in it did you see when he was in austin i saw him in san francisco i in san francisco so i saw him when he was here and he's got this whole part where he's basically like you know he's like i challenged you know this dictator who was doing this thing and then boom that clip goes viral i've made fun of trump at this thing boom that clip goes viral the likes the views the followers the comments pete and he's just like fucking inject this into my veins i need that next hit so i went after the next big dictator and then the next big fish and then all of a sudden like you know there was a price to be paid for it he talks about how he received something in the mail that was like you know some something like anthrax thing and it got on his kid and it turned out to be all okay but like his wife was like dude you have to figure out how to we shouldn't be poking very important and that's kinda of what you're talking about right guys figure how to keep that on a leash and i think about that a lot and i think about it you know even with what i do i remember i was i was on some big morning show and i remember thinking like there's a i know what i could do to make this like national news like i i know i could i'm i've got a you know an audience of several million people right now what i what and then just going like life is too fucking short and then also i wanna continue to live in reality and so i think what happens is certain people get desperate or maybe their judgment is not good or they don't have someone in their life it's like you know that could work but what about this this this and this as a consequence and you can you could become un unchanged very quickly especially if there is any also you know comorbidities with like a mental illness or you know like and so i it most of the people who wanna be in the public eye you're already a little you know like that and so you gotta be really really careful and i'm i'm worried about where some people i know are going yeah sam as a fitness influence i've been wanting to talk to you also about your excessive exercise and what this might be leading to and man like you might spend three days in darkness only doing squats just to you know hit the you hit those views i'm in a good place my friend i'm i'm doing everything right at the moment we'll see how long i could last ryan this has been oscar man i i appreciate you coming on this is fun thanks for thanks for coming and the they we didn't even say the name of the book curt just calling right it's awesome i i've not read that one yet but i'm gonna buy i've read everything else perennial seller way i guess i've read four conspiracy and trust me i'm lying and then the middle two what our there's the stillness one i haven't read that one still of the the key and then he goes to the enemy is the one i think you're missing you go damage is very good and obstacle is always is very good those are both both great well and you get your awesome i appreciate you thanks so much