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curiosity is the cure for boredom there is no cure for curiosity and if you and I read the same book The Things we'll pull out of it would be different like Jonathan lead them the novelist
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said that if you think something is original you just don't know the sources all of my output is a function of what I'm reading and experiencing we're a vessel for the experiences and ideas we come across who do you admire and can you do your version of that the artists that really
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resonate are when they pull taste and audience taste together in the center of a Venn diagram and the challenge is finding the overlap between those things everyone that's put out work into the world has had the experience of thinking this is the the greatest thing I've ever made and no one likes it conversely you put something out that you think I think this is good but it probably won't do great when I publish it and that thing goes crazy
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viral searching for certainty is just like a tools Sarah because there is no such thing well hello everyone it's Jim O'Shaughnessy with yet another episode of infinite Loops I have been looking forward to having Billy Oppenheimer on my show since I discovered his amazing stuff
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and he was gracious enough to agree to come on and chat with me he is the research assistant to Ryan holiday we'll get into that after a little bit I love the fact that you cold emailed him in in 2018
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and and offered to work for free I love your style welcome thanks for having me Jim I'm a fan of of the podcast I was surreal when you um reached out to to come on oh well I'm happy to hear a
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long time listener this was really cool very very cool uh it's great when people like us discover each other I think so like you you went to work for Ryan who I find very fascinating I read his first book trust me I'm lying and like before he got into the whole stoic thing and everything I
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loved his first book honestly because I thought it was such a great expose I used to do a lot of traditional media and like I I I it just rang so true with me with like how like people get these uh things put in into the traditional media but you ended up working for him so you help with
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this research you helped write edit the five more recent books you grew his email list five hundred thousand okay so listen up uh fans uh you're gonna teach us how to do that or is it a secret
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um well I I wouldn't say I grew it I was I I joined this team when the list was at 50 000 or so um and it was it definitely was having some momentum and I think the one the the main thing I've learned from Ryan is and I've written about it a little bit on Twitter and elsewhere but
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he doesn't have he doesn't even know the login to the software we use to send out the email the key he doesn't know what the list is currently at he's he's solely focused on the content side of things
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um and that's been a big lesson for me is just to focus on putting out good stuff and I think the numbers follow and and the other thing is Ryan is he's not in a rush to grow that that list he's I
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think his exit strategy is is death with the daily stock stuff um so it was just it was just a matter of time before you hit big numbers like 500k and I'm sure it'll continue to grow from there so uh we we Are Spiritual Brothers then because I do not know login to any uh part of our confusion
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to people who are joining us so I'm sitting here waiting on Zoom I don't set up any of these right so I'm like psyched to be talking to Billy and I'm noticing the time is kind of like ticking
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by and I'm like huh I wonder what's going on so I checked my email no email so I I'm like maybe he messaged me on Twitter and you did in fact message and my side fell down and did not send you the appropriate link so I apologize for that uh but like Ryan I have no idea what the logins
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are for any of our stuff at OSB uh I I I learned on Twitter when we got a million downloads for the podcast yeah I I learned it right everyone else did I have this thing which is I I'm naturally
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a fairly competitive person and what I didn't want to happen was I didn't want I knew because like human OS we all run human OS right I knew that if like a show that I really loved like for Brian morescu who had a he was a fabulous book and I loved that podcast and I and I thought
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like this is probably going to do not really great numbers but I didn't look intentionally yeah and I never look I have no idea what our most popular podcast is none the reason I don't is because I
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know that even subconsciously it would bias me right and and so tell Ryan I'm the same as him I have no idea and thank God I have guys like you because I would yeah the [ __ ] show without it yes well I find it's this is kind of a common trait of people who actually do the the work
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almost I most admire and then inspired by is just the sole focus on doing the thing um and then The Accidental byproduct of that is that that they actually have the largest audiences also yeah in in in my uh case I'm not looking for the largest office I I I'm
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intentionally like doing everything wrong yeah yeah because like I want people who are you know it's as selfish of me but I I want to hook up I want to meet people like you I want to meet
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people who are interested in the same things that I'm interested in and right that's very selfish I'll admit it um that's how I find really cool topics and really cool uh people like yourself
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to talk to I want to talk about your stuff the six and six I I love the way that you uh first off you weave things that are people are interested in together right like sports uh literature politics music stories and then you get a couple of great anecdotes and you get a couple of great quotes
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and I think personally it's a great way to tell a story because like you know Stalin didn't say it but it's such a great quote we're going to continue to attribute it to him uh you know one death is a tragedy a million hours statistic right and he really or whoever came up with that
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copywriting and attributed to Stalin that's a good yeah by the way um uh I love uh Banksy and and he said any any [ __ ] sounds smarter if you put the name of a dead philosopher after it yeah
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yes but so so what was this just a natural the six at six the the the storytelling Style um the the way you you you you do it did that evolve is it just something that you naturally fell into talk to me about that it's evolved um so initially when I was starting the newsletter
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um I had a conversation Ryan was encouraging me to start putting my own work out there for a while I was just writing kind of behind the scenes stuck with him and he was starting to encourage
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me to put my own work out there and I knew I was going to start a newsletter um and I didn't know one of the Hang-Ups for me was that I thought I needed to have like my Niche or my my Niche um in the way that Ryan has stoicism and James Clear his habits and a lot of the people I I
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read have kind of their their Niche carved out and I was for a while trying to figure out what that was going to be and I talked to Ryan about that and he was like you just have to start you're
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trying it's like you're trying to map out the whole nine innings just throw the first pitch and so I just I I started to think about what are some things I currently do that would lend itself to newsletter content and I've adapted his note card system that he uses to research his books
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um so I was I was thinking my first idea was to just scan a couple of note cards each week that I had made that week and send them out and I played lacrosse in college and I wore number six so I was
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I was going to call it six something it was just gonna be six note cards each week and then I scanned a few new cards I just didn't like the way it looked um so I and then I thought okay I'll just transcribe these so so the first 10 or 12 editions of the 6.6 newsletter were just six things I was transcribing straight from note cards um and then over time I I kind of evolved it into where I pick and steam each week and all six of
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um of those notes are around one theme but it's still I'm I'm basically still transcribing straight from a note card um but I try to have each note card be uh like a standalone so someone other than me should be able to pick it up and and get what the point is of it so it's not just like
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a quote it'll be the way it might look in it in an article so there's like a a lead into the anecdote um so it's evolved it started out as just six completely different unrelated ideas that I'd come
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across um and now I like the picking a theme and having everything revolve around that one topic which is is very cool because it is very specific to kind of uh The evolutionary mimetic way humans
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learn right and and uh another thing you say often and I like this idea and I I think it was originally Andrew huberman's the introjection where you absorb the qualities of somebody that you're interested in yes I like that idea and and I also like the idea when you don't know
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what to do you say what would you know in my case find men do or a voltaired or or something like that right was that uh just from from your reading uh from from Ryan where did you light up on that
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uh right Ryan and Robert Green are two of my like those are the two people I think of like how would Ryan or Robert write this I'm also a huge fan of Morgan housel who I know I know you've had on the podcast yeah um I I love his writing style he's a big influence on me
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um and he probably is where I along with Ryan and Robert is the biggest influence on me in the way that he I like the way he'll use a story about ice ages for instance and tie it back to compound like the phenomenon of compounding um the way he takes like two seemingly
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desperate ideas and and weave them together in a story um was something I was consciously thinking about when I was starting the newsletter um and he still is is one of my favorite people to to read
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Morgan's really interesting I tried to hire Morgan and he he had my number way before uh I he was quick on the uptake and said no I won't work for you because this is way before Morgan had done much of anything and I'm yeah uh and was super impressed by uh you know his style I
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love that I love the way he he does things too he really understands the power of Storytelling and uh like he's definitely somebody I could learn much from uh because I love as you point
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out right he he marries very different things together yep and that creates this beautiful little ah oh yeah you know this aha moment right and yes and and so it's it's also kind of like uh
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observational learning uh Andrew uh banduro has a what he calls social learning theory um and you know the you mentioned that um you often when you were looking for another research assistant uh to work with you you'd give him a biography and say give me two anecdotes and
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two quotes and and they couldn't do it talk to me about that I find that really interesting yeah um there's just I I think one of the things Ryan is really good at is the gems he pulls out of of books that he reads and it's it seems like it would be
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an easy task but it's interesting we've had tons of people try this kind of trial um task to to potentially do some research with us and the things they come back with just or not interesting or they don't have that eye for what will be interesting to others and
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so like Morgan when he's reading and he comes across a story that he pulls out of a book that hundreds maybe even thousands of other people have read but when they when they read they didn't see what Morgan saw in it there's like an eye for
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what will be interesting to others um and I don't I don't know how it you develop it I think just through repetition I've talked to some other people about like this idea of taste and can it be developed or is it kind of um something you have or don't have and I'm not exactly sure
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what the answer is to that I I think that uh it's both really it yeah is some I I think you need to be incredibly curious which you clearly are and and you know Green Brown says curiosity is a [ __ ] starter and I love that quote because I also love that Dorothy Parker
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um you know curiosity is the cure for boredom there is no cure for curiosity and and like I I am just like I I cannot I just can't stop being interested in stuff and so that how what
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happens is you dive down the rabbit holes and I'm just looking at my notes that I was doing working off your stuff and uh John Myers definition of a writer's block is the there's two people inside
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your head uh yes writer and the reader I love that that was yes I'd seen that uh I don't know whether you read David Shields reality hunger no but you might enjoy it because he's an essayist and he's like really hardcore uh basically one of his great pull quotes from it that you know I just
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always have in my mind is he's going on this diet tripe about how digital media is going to destroy the old copyright Network because digital it's not a fair fight right digital wants to be free
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and and any and he puts it so beautiful hopefully I put it up on Twitter a couple of times but his tagline I love is reality can't be copyrighted and I think that that's really really true and one of the things that it made me think of that I wanted to discuss with you is this idea of
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uh Jung Carl Jung the uh the uh student of Freud and ultimately the Rival of Freud had this great quote which is people don't have ideas ideas have people yes you do you agree yeah I think so um another person um I'm really inspired by is Rick Rubin and he talks about
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um nothing begins with us like everything is kind of we're a vessel for the experiences and ideas we come across and I'm I'm a big like everything that I all of my output is a function of what I'm
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reading and experiencing and um so I definitely I definitely agree with that so like Nikola Tesla he he believed that our brains were essentially receivers and broadcasters and that literally you pulled your best ideas out of what he would call The Ether
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um and Rupert sheldrake is a morphic field guy with same kind of idea um and and I wonder like back to taste for a minute right um like there's artists I can't remember who said it but it was along the lines of like
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there's three different kinds of artists right those who innately see beauty and then have the ability to have others see beauty as well and and then the second type of artist was uh he this person said even more impactful and he referenced Van Gogh and and he said these artists are Time Travelers they see what others will see but they see it like 50 years before everyone else can see it right and and then he said in the the rarest cat I
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can't remember who's wrote this I I read a lot and I remember what I read but I don't always note who wrote who wrote it yeah um but the the third one that I thought was fascinating was he goes the third category of artists that really I am obsessed by are the ones who are seeing
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things that I I simply as far into the future as I try to look I can't see so like I will I wonder about practice you know practice your scales you you had a thing about Kobe Bryant spraining is uh
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ankle in the in the uh championship and I loved I loved his solution to it like oh okay so what is something I can do that would make my ankles stronger than anything else and he discovers tap dancing yes do you follow a similar like when you're coming up with all your ideas for your
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newsletter and and pitching stuff to run is is that how you go about it do you just is it like this is what I'm trying to solve and then you go broad how do you do it talk to me a bit about your
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process yeah I think of I think about that uh the scales thing a lot and I I've recently realized that the the note cards are like that's the Tyler Collins question right he's like what do you do
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that is like a a Pianist practicing scales and I think for me it's it's making no cards um and one of the things I've I think has helped my taste develop is getting to send things to Ryan and have him either say this is good or this is bad or drafting an
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article and sending it to him and he rejects it and says these are the things you need to fix about it and then I iterate on those notes um so I and over time like now when I send him
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a draft it's closer to where it needs to be on the first the first pass than it was two years ago um but the the note cards are big because uh especially doing it by hand I think because there's times where I'm going back through a book and if I can't convince myself to go through
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to put the energy or the effort into transcribing something from a book I'm reading onto a note card um it's probably a good sign that that thing is not worth capturing like Mitch Hedberg had this
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joke about how he would keep his pen on the other side of the room because if he had an idea for a joke if you couldn't convince himself to get up and go get his pen he was he would convince himself that the joke wasn't good enough and people often email me because I have this article
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about my new the note card system and they'll be like you know you can set up kindle to have it go directly into notion and I that's that's like the exact opposite of what I want to do um because I when you read a book on the first go like everything I I underlined and highlighted
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a bunch of stuff and then you go back through and you realize that a lot of those highlights don't hold up as as interesting and through the practice of identifying which ones are worth transcribing
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onto a note card over time your ability to to pinpoint those things gets better and better um so I do think it's like the a really solid form of practice I agree uh and obviously I have some motivated reasoning is I've kept more than 40 Years of handwritten journals and oh wow I'm going to uh have them all digitized so that the AI can explain me to me uh but I you know I I this is speculative because I haven't found
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anything like that can really confirm that this is correct I think that there's something different uh it occupies it different and for those of us who are listening I'm holding up a pen here
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if you're watching you'll see me holding it up um but I think that it goes to a different part of our brain when we actually write it out with our own hand and the unfortunate thing is I want to kind of find like a scientific reason for it and most of the reason for it are pretty
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and not opposed to woo-woo I think that some woo-woo actually makes a lot of sense yeah um like I am convinced that it you're physically getting a thought out of your head and putting it into the real world or else perceive as the real world yeah and and so I do persist in writing
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notes rather than doing like all of the uh most of the folks who are teammates of mine are like your age and yeah and they're all like will you please just put it all in notion and like you are this
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chaotic attractor and we want you to capture it all here and I'm like but that's how like all this works for me right and and I love that forcing function of keeping the pen on the other side of the room that's yeah wait I'm gonna I'm gonna steal that for sure yeah and because I like you
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I do read on Kindle or Kindle for iPad right and and it's so funny that you say that because what I do is I export the notes the highlights right and the notes that I piped into the iPad but then
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that's my raw material right let me go then I go through that and I'm like I have no idea why I highlighted this that kind of yes down right yeah yeah yeah and then and then I write the ones that I think are worthwhile hold up yes right and and so it's like that
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iterative process and it just it it leads you to a better outcome I think at least it does for me but like one of the things that I wanted to ask you about is I I I'm mostly just because of what
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I'm doing now I'm mostly reading non-fiction I also love fiction I'm a huge fan of fiction and you know do you do you try for a balance between fiction and non-fiction when you're you know doing your your newsletter what about cultural blind spots like I know I've got tons
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of blind spots right we all um How do you first off let's deal with the fiction versus non-fiction and and then how do you have a solution for cultural blind spots I read mostly non-fiction um
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I my favorite genre is biography I I just love reading um about artists and people throughout history that um like right now I'm I'm going through uh I recently read this this biography of Dr Seuss and it was the biographer that wrote it has written five
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or six others so I ordered those I'm just going through it through his his work and that tends to be what happens for me is I get um I find a writer who I really like and I just order all their like that's that's what got me uh that's what happened with Ryan for instance is somebody
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recommended one of his books and I enjoyed it so much that I ordered all of his others and I still have that habit of just finding someone and going down the rabbit hole of their work um
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and it tends to be non-fiction writers I think because that's the style of of writing I'm doing um I'm attracted to that that genre um I definitely do have a blind spot for Perfection um and I don't know what this the solution is I I sort of just I'm trying to follow
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what interests me like I I quit a lot of books if if they're they haven't hooked Me In by chapter three or four I'm I move on because um I'm just trying to find the things that that really hook me in um yeah I don't have a good solution to the blind spot question
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yeah I mean what one of the things uh I'm a uh I I probably uh you left to my own devices would probably read more fiction than non-fiction uh just because I like I do the same thing as you
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do by the way when I find a writer like Robert Anton Wilson I always quote him yeah I found one of his books and then I had to read all of them yeah I thought like he was such a cool guy same
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with Bucky Fuller bucket puller is much harder to read though to be honest yeah and it's like um you know the hero's journey he is so much easier to listen to his interview with uh I'm talking about Joseph Campbell um oh yeah the power of myth yeah but yeah the power of myth but the the
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interviews that he did with Bill Moyers for PBS are much easier and get the it across much better yes his own books but like um like in fiction uh David Mitchell is probably my my most favorite uh
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literary fiction author he wrote Cloud Atlas and um he's just a he's like a really great writer um and and so what I find some of the times helpful is I see connections between non-fiction and biographies you must love David senra's uh Founders podcast love it yeah David's a great
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guy he's so insane oh [ __ ] for for a while I I listened to that podcast and I thought he had somebody else in the room with him because he often will do something where he'll say like you and I have been talking about this for weeks and I thought he was talking to like a co-host or
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something and then only recently I realized it was just him in there I was like how does this guy have the energy that he has when it's just him in a room recording unbelievable he's amazing
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and he's like that in real life too yeah I had lunch with him when I was down in Miami and like I he just crackles with enthusiasm and I just can't help but be drawn into it right yes like when he when you get into a conversation with him you just lose all sense of time
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yes like we had this incredible conversation over lunch and I looked like looked up and it was three and a half hours yes he's someone I've talked to a bunch about the taste question because
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I'll often listen to one of his episodes and then I'll order the book that he does an episode on and I'll read through it and almost always David has pulled out all the best parts he has unbelievable
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taste and he it's a great like service that he does in that he he takes these long biographies and does an hour and a half episode and and gives you the best parts from from that book totally and like that that is I think you know one of my uh ideas about the new world that we're
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moving into is that for the first time all like ever you'll be able to be a solopreneur if you have good taste and you are an excellent curator David is exhibit a of that like David that's his he found his calling yes and he has outstanding taste yes like when we were talking about
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um certain things like he would tell me oh but did you think about this and I'm like no I didn't but that is such a great idea so he's like this he he is able in in AI one of the things that you want
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to be able to do is compress ideas yes right and and David is like a a a definitely a human large language model that can compress ideas down to their core but but not too much right it's just
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right and I definitely think that yeah that taste you can learn through repetition to have better taste right like when I read stuff that I wrote originally it basically it sucked it was horrible and I you know like I have these journals going back to when I was 19. uh
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but you know just through repetition repetition repetition that's why propaganda works right yeah and so you just repeat repeat I wonder good well I was gonna say for you um do you think the repetition in in terms of developing tastes has it been writing reading
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both is it is it reading great writers some of that rubs off on you you think totally you know um uh uh Hunter S Thompson actually typed out the Great Gatsby yes and and the reason he did it was
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he said he wanted to feel he wanted to know what it felt like to write a masterpiece I I first off I love that guy yeah secondly I what a what a cool way to to do something I would have never
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thought about doing that the one thing I did do when I was young is I memorized 100 poems um because I just thought that that would somehow help me if I like have in my database like to his koi mistress had we about world enough in time this coinless lady were no crime right
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and that's yeah marvelle and then that that brings up Shakespeare's sonnets which brings up Dean xanaduated Kubla Khan a stately pleasured um decree so I definitely think there's something to that but I did that before no I'm knowing about Thompson typing out Gatsby so I definitely think
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that the that you can learn to have better tastes I I definitely think that that's true but I wanted to ask another question that kind of links to our friend David I wonder is do you think that
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we could learn um like because everyone we tend to read is survivorship bias right and Survivor surprise gets way overused by the cognitive bias crowd like yeah I I often will say you know people people who say that everything is due to luck uh the way I transformed that was
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everything is due to luck said the most unlucky person in the world hey yes but but I wonder like that isn't something and I just thought about this when I was going over your stuff like do you
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think there would be value in like looking at like abject failures but right probably I mean yeah I don't know um I'm not sure I'm trying to there's there is a writer who talks about um studying bad work as well and there's a story that uh John Grisham I think tells when he was
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first thinking about writing I forget the first book you wrote um but he was a lawyer turned novelist and he was thinking about making the break from being a lawyer to write to a writer and
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he said one of the things that pushed him to go for it was uh reading bad books and that gave him the confidence that he could do it too so I think there's probably something to studying bad work um I don't actively go out looking for it but I'm I don't know
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I'm not sure I'm in the same camp as you I'm not sure either and but as as I was getting ready to talk to you I'm like huh I wonder if he's ever kind of thought about that right uh because like there's talk about sample size would be a huge sample size of [ __ ] yeah
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yeah well maybe and um like I've heard the Pixar guys uh Jon Lester talked about um when they were setting out to do their first feature film they made a list of what they didn't want it to be um all the elements in the movies there they watched at the time that that they didn't like and they were trying to actively avoid those things so I think similarly it could be useful to study people who wear failures as okay let's not do these things
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um but I and I think that you get some of that when you do read about the the people who have um survive the survivorship bias like in every biography you read tons of stories about you pick up tons of lessons of what what to try to avoid um
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so I don't know yeah Douglas Adams said um that um humans were uniquely qualified to learn from the mistakes of others and yet apparently highly disinclined to do so which is just so true yeah and and I like your your statement about
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um when you read about these incredible people you're also reading about all the times they [ __ ] things up right yeah definitely I I [ __ ] things up all the time and I I find that that is
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where that that is where your maximum opportunity for learning something new comes right I think so yeah if your uh Nabokov had this great line which was basically curiosity is insubordination in its purest form and I I love that because I am by my nature insubordinate and yeah uh you know
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ungovernable and when people even when I was a kid um and ask what I wanted to be I said unemployable yeah wow because you know I I just I I had that natural kind of inclination but I also believe very much I mean if you look at like the way we manage money was all process
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and so I'm a big believer I I note that you you talk you mean like you learn by doing like it was through actually no I I learned by studying I learned by looking at data uh and saying I I
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learned by saying I have no [ __ ] idea what the best in way to invest is I guess I'm just gonna go to the videotape as the old Sports guy said right let's go right right and and that's what I did that's what quants do we go to the videotape meaning we're like okay let's let's look at how
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buying the stocks with the lowest priced earnings ratio did over the last 50 years right and right and the mistake that people make is they say well companies were different back then it doesn't hold
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now and it's like yeah companies were completely different human nature was exactly the same right you know human nature prices Securities so you can look directionally across all the data and
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you can do really really well by just following what what uh the the data suggests right wow cool and so like Annie Duke is a friend of mine and and I know that you like her uh with the process persistence and she has the idea of she she calls it resulting yes really what a lot of
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this is is is process over outcome right like if if you are an outcome thinker what Annie calls resulting you're [ __ ] kind of because you you are essentially only as good as what your last result was right our process you can you can have a bunch of bad results and just keep going and yeah you have this idea that progress is ultimately uh provides magnitude of consistency talk to me about that a little bit yes um
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where that trying to remember where I think that was my takeaway from reading something Morgan had written I'm forgetting what it was but I remember that article stem from something I I read of Morgan and in the way that he sees something and
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ties it to finance I saw that and tied it to the creative process and um I think Ryan's a good example of this and the note card system as well is is it he he's now working on a book where he's using note cards that he made 10 years ago and
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the the function of the process there is that um he was doing the work without expectation of when this was going to pay off and now 10 years later is paying off um but a lot of my favorite
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artists are like that they're they're so solely focused on doing the work um and they have that long-term View and knowing that the overtime just stacking those pieces of the process leads to enormous results that that you can't foresee when you're in the day-to-day of it but um
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I'm really trying to remember where where I read about that from from Morgan house because I wish I could credit him but um I forget what it was and another thing you say though is that um I think
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you called it um the repetition repetition the magnitude is and you said panic in your brain is your brain calling you out for not putting in the work yeah and and I thought that was great because what you what you weave together there was emotions are really predictions from your brain or
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your mind or whatever you want to call it saying like how much work have you put in yeah if if you put in a lot of work you tend to be pretty chill you're easy to Vibe with if you haven't put in the work you tend to be like really jumpy and like why why would you ever ask me that like yeah yeah
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you know I I and and then I think unfortunately a lot of people go immediately to [ __ ] right like oh of course I know right because our brain is is thinks that it knows everything and of course it
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doesn't at all yes and and so you know the the whole skill versus Talent is another thing that you talk a lot about that I'm really interested in because do you do you need to have a natural
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Talent first to build the skill or do you can you build the skill like I think you can build so that that distinction is I I got from uh dharmesha the HubSpot founder and he said that skill is the ability to do something Talent is the rate at which you acquire the ability to do
45:13
something and he was saying that he doesn't feel like he's had a natural ability for anything he's done he's just put in the work and over time he's acquired that ability and as I've thought about
45:28
I I really resonate with that because I never felt like I was naturally good at anything by putting a lot of work and got good at things um and that's I do think that the skill can often be acquired um it's just a matter like how fast you acquire it will vary
45:50
from person to person but um I do believe that it's kind of universally acquirable I think so too um I I don't know where I come out on the um on the how much nascent I mean like I loved class I love all music so I love EDM I my grandson who's nine is starting got
46:16
getting into techno and EDM and he when he learned that I loved it he was like Haba are you kidding and and so I made him a a Spotify playlist and and uh the greatest I think it was one of the nicest things I ever heard said about me uh he said
46:34
to his other grandfather uh gampy I love you a lot but Papa has better music taste that's awesome but you know it's like one of the other things that you say that I really that really resonates with me is care but don't care too much yeah like I think that I just was
47:00
very lucky that I basically when I was young I cared a lot what other people thought about me but that that burned off real fast yeah yeah and and that is like very freeing do you do you do
47:17
you care very much what other people think about you yeah I do I definitely do I'm trying to get uh better at I I think caring less about it but I am I I when I put something out I I it feels good that people say that they like it um I'm not like someone that is solely just I put this out and I don't care what people think um I I like hearing that something I wrote resonated with others or um but I the care about not too much
47:59
I think I'm also pretty good at if I put a lot of care into doing something uh especially with like a written piece of content and then I put it out and it doesn't do well um I'm also okay with that because I I'm I'm happy with the work I put into it um and it
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just for whatever reason it didn't land with with others that's okay but um that's how I often think about the the care but not too much idea um but I do I could probably get better at being less
48:38
worried of others what would others think I think it's fine if you use it as feedback to get better um then it's very useful I I'm more of the like I I really believe like one of the I'm kind of a Taoist so stoic um and and I have found that the the mixing and matching
49:03
of taoism and stoicism works just right for me right yeah like go with the flow um don't react I think people are way too reactive like I I I only get worked up about something is if I think that I could by my actions make something different and better and I don't
49:27
do that then I get worked up but as long as you do it then like the like today on Twitter like there's this whole thing about blue check marks right I saw your yes yeah [ __ ] get it man I I was a legacy check mark I didn't apply for it I got it probably because of my son Patrick to be
49:50
honest the guy was like wow we might as well do the old man too at the same time and so I didn't apply for it I got it they took it away I bought the Twitter blue I wanted to be able to edit my
50:03
tweets and that kind of stuff yes but to see this hysteria around like and they're making this poor woman the character of the day it on Twitter like you're people will die because of this okay
50:18
right you might have wanna re she should have Twitter blue so that she could edit that tweet right right right but like I don't care if if you know if I can't do anything about it like my opinion is just as worthless as everyone else's right and and I I just think that this reactive
50:44
nature of you know general you know shrink wrapped human OS is to be very reactive yeah and definitely I I think that it's better to kind of like lean in to Edith Piaf the French singer had a great thing where she says man if you want to be a star the only way that's
51:05
going to happen is you got to leave into your faulty your defects because like that makes you different that makes you unique right and sure and without I'd be interested in all the kind
51:20
of successful people that you write about and everything have you ever found somebody where they weren't persistent where they weren't process oriented where they weren't focused I don't no I don't think so um
51:44
no no I can't think of anyone my so one of the things I often think about is aminage the comedian um he was asked if he he thought he was going to become before he was a big time comedian he was asked if he thought he was going to become a big time comedian and he said he didn't like
52:04
that question because that question implies that he's doing what he's doing as a means to some end and for him he had already won because he got to do the thing he likes to do which was comedy um and that seems to be a common trait across domains and people that um like David Center I think is a great example of someone who the work is the win like he just loves doing the thing that he does and getting to do it is is the win for him
52:42
and the things I the external recognition the people reaching out to him the cool conversations he gets to have um the cool dinners he gets to go to are a nice cherry on top but for him the best part of it is sitting down in his room and recording a podcast and that
53:05
I think is the common trait that I see across um the people I write about and read about and look up to um so it's for them it's not it doesn't seem like they have to get themselves motivated to
53:19
go do to put in the persistent work it's it's the thing they just are are compelled to do I I have found much the same um I I used to say like the worst thing that you ever hear is oh I want to do this because I want to get rich I can count on my hands I mean that was that's
53:44
my old business right I was an asset manager and right but my clients were all rich and right and when I would talk to them like what I found which really resonated with me was like I would do what
53:58
I do for nothing right I would do it just because I want to do it yeah maybe that's kind of selfish on my part but like I found the same underlying characteristic in all these fabulously rich people
54:10
whose money I was managing it was never money ever it was like if it was Ralph Lauren I'm not saying we managed money for him I wouldn't name somebody if we did right right and infer that I didn't manage from Lauren's money yes but the but the fact is that he did what he wanted because he
54:28
wanted beautiful clothes he he was obsessed by them right like I talked to various people who we did manage money for and like every time it was always no no no no no that was uh out that was a nice byproduct I I would have definitely been doing it which leads to that whole process
54:50
right because you just you're gonna keep doing it whether it has this huge payoff or not and yeah it it kind of also allows you to build an algorithm for kind of success which is David he wouldn't
55:05
put it that way but it's kind of what he's looking for he's kind of looking for the common characteristics that that make these people the way they are and one of one of the things that you talk about which I really like is the this idea of conceptual ancestors right and because as you were
55:26
saying uh about the comedian right I my viewpoint is anyone who is alive today right now has won the cosmic [ __ ] Lottery yes as we are living at the safest time in the Earth's history we are
55:42
living at a time of the most Innovation we're living at like all of these things and we are all the results of millions of years of unbroken progress what do I mean by that well our ancestors procreated and here we are right and for sure and so one of the things that I like about the
56:06
way you approach things is where you talk about Michelangelo was obsessed by Anatomy but that in in uh affected the Sistine Chapel yeah nothing got siled right and Shakespeare's Prosper Prospero
56:21
became Tolkien scandalf and I don't know if you're a fan of the show succession but like Logan Roy is basically King Lear meets Rupert Murdoch right right do you find that that's the way you like
56:38
things come together when you're writing about them yes for sure um I'm trying to remember I'm I'm looking for this line I recently uh on this conceptual ancestors idea um Willa Cather she was a a writer I believe but she said that there are only two or three human
57:02
stories and they go on repeating themselves as fiercely as if they had never happened before um and I I I think that's so spot on like everyone is kind of all the great stories are a version of each other just with different characters and um
57:25
and it's been a big uh a big lesson in like reading biography is the the common through lines you see again and again um but the the conceptual ancestor thing I also not not just in the the context of movies or books or I also think about that
57:53
kind of tied to the introduction introjection thing we we talked about earlier in finding people you admire and kind of becoming letting them be your conceptual ancestors um is is a pretty good strategy for going about like the what you should be doing the kind of work you should be doing who do you admire and can you do your version of that you know as as I Was preparing uh and going over your stuff uh I I I came across that idea of yours
58:34
and and so I do this two quotes two thoughts from series every day yes and and so I thought you know what I'm gonna go look and see what the first ten people that I immediately put up as as maybe maybe
58:50
using your idea of um of conceptual ancestors maybe the first ten that I did arm maybe in some way my conceptual ancestors and so I thought it was like really interesting I'm gonna give it to you so number one bull Terre number two Marcus Aurelius number three Nelson Mandela Victor Frankl
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Aristophanes Bob Dylan Picasso Buckminster Fuller Robert benchley and Isaac Newton those were my ten that I that I quoted first and and I'd never even thought about that until I read your conceptual
59:29
ancestor piece and I'm like I wonder if there's anything there that's super interesting yeah do you like it but you're some of you're some of those people and and and so if I would ask you if you off the top of your head I'm putting you on the spot who who would who would be on
59:48
your list if you were doing two two Thoughts From A Day who would be your first go-to's uh uh definitely Ryan and Robert Robert Greene um I told you I originally read this Dr Seuss biography and I've just been obsessed with him recently so he would be on there um and then after that I read about Jim Henson the creator of Muppets um he would he would be I love the way he uh talked about his work and why he did what
1:00:26
he did uh so he would be on that list Bob Dylan would prob he's my favorite musician uh Bob Dylan and John Mayer two of my musical Heroes um Marcus Aurelius would have to be on there I spent a lot of time with Marcus um to us
1:00:52
uh and I'm looking let me see um I don't know who else I would put on there I think I'll I'll go with those for now okay I'll have to think about but I'm I I I would when you think of the other ones would you put it up on Twitter so so that I can uh see
1:01:22
you or download it out list I would be really my 10 conceptual ancestors yeah yeah because I you know these might not actually be I haven't really I I just did this because I keep everything
1:01:34
on Apple notes because yeah easy and when I'm not writing it out actually by hand it's just really easy for me too and so I just keep the list as I go through people I'm like okay maybe I'll but these first ten were like immediately who am I gonna go for I'm gonna go to Voltaire I'm
1:01:52
gonna go to Marcus Aurelius Etc I would be really interested in your ten okay because I I wonder do you think like do you think everything's a remix like I wonder about that a lot yeah
1:02:07
you do yeah I do I'm a big I'm a big believer in that idea and and maybe distinctiveness emerges from you your unique remix right yes yes I think so um I think the the uh the unique so I was listening to um Rick Rubin just started a podcast and he had um this filmmaker on I I'm
1:02:42
forgetting the guy's name but Rick Rubin asked him is does one script could one script make one movie or could it make 500 different movies and the guy said if you and I had the same
1:02:57
exact script we would make two different movies and it's the same and if you gym and I Billy add that same script we would make different movies so I think there's something about like and if you and I read the same book the things we would pull out of it would be different
1:03:16
um the so we're working with the same raw material but what we find interesting and what we want to pull out and add to our uh remix that's where your kind of unique perspective I think comes in and as well allows uh what we what we think to be original work
1:03:35
um like Jonathan lead them that the novelist said that if if you think something is original you just don't know the sources right yeah and I I agree with that um I think to be original is actually just to have the most obscure sources
1:03:53
that's a really interesting idea it's it's along the lines of uh I was chatting with a colleague earlier and um we were talking about all of the source material that is now available that it's out of copyright it's in the it's in the history books and and then
1:04:16
like I did a deep dive on that once when I read um uh Dan Brown's The Da Vinci Code right yeah I'm a kind of a history nut and and I'm like I'm reading this book and I'm like you know I think I
1:04:31
read something about this and so I went on this I jumped out of that rabbit hole it turns out like the entire thing is based on historical actual occurrences there really was a French aristocratic
1:04:47
family that yeah that they were the descendants of Jesus Christ right and I'm like I'm reading it I'm loving it oh wow to see it everywhere like Men In Black yeah that comes from original interviews from the 1930s and 40s where they would interview people who had seen UFOs and all of them said
1:05:10
different things about the aliens but they all said and yeah A non-descript car pulled up and Men In Black suits came out oh I love that so it's like we were talking so we have different verticals in O'Shaughnessy Ventures and one is infinite media and my colleague that I was talking
1:05:30
to is the lead on infinite media and we're like yeah we could just you know what we could just like go to history and boom you got 12 new uh uh ideas for a book or a movie or or whatnot uh 100
1:05:46
and and you know you you had the your your coffee cup theory of AI which I love I I know you or I don't know if you know but I'm I'm the chairman of stability Ai and an investor in that company and uh but I love where you say uh the artists that really resonate are when they pull taste and audience taste together in the center of a Venn diagram yeah like is there do you think there's a formula for that or is that just
1:06:24
I think it's it's the The Perennial challenge that will never never be solved and whether it's made by a human or by a computer there's no way um so that Venn diagram is like the one circle is the artist's taste and the other circle is
1:06:49
um the audience taste and the challenge is finding the overlap between those things and every everyone that's put out work into the world has had the experience of thinking this is the the greatest thing I've ever made and no one likes it
1:07:07
inversely you put something out that you think I I think this is I think this is good but it probably it probably won't do great uh when I publish it and and that thing goes crazy viral um and so taste is trying to hone in on
1:07:27
better calculating what's going to work with the audience and what isn't I think um and it's really there I don't think there could ever be a formula or you could ever know for sure it's always at best it's an educated guess like uh Matt Damon talks about how um he says they're all bets he was
1:07:47
asked like is there has there ever been a movie you worked on where you knew it was going to be a box office hit and he said they're all bats um you can you can get a great team together a great
1:08:00
script uh all all the ingredients and for whatever reason the the audience doesn't like what you made um and I I agree I agree with that and from my experience of writing online and um and working on on books with Ryan and others it's it's really hard to know for sure what's gonna work
1:08:24
um and I think it's that's kind of the best the best part about creating is um is getting that feedback from the audience and learning what what resonates with others and do you think sometimes that like I think that that that's always been part of my thesis
1:08:52
about why markets work so well yes essentially that's what prices are right prices are feedback right and like you you might not like that feedback right and and and you might rally against that feedback yeah but that's what they are
1:09:13
and that's why I'm better for the most part markets work and you know the more you try to regulatory capture them the more you skew them against the actual best optimized outcome right um and yet like Perfection is is is a myth there is no such thing as Perfection I had a great new writer Edward rooster uh and he had this great line Perfection is a 100 tax and I loved that because like you can't you Perfection is something you strive for but
1:09:54
never reach and like it seems simple to me that you should understand that like Perfection is unobtainable it's unobtainium right and and that doesn't mean that you can't strive to do great things but right like you're never it's never going to be perfect we're all flawed to some degree I I'm a big fan of Jed McKenna the fictional character who it tells us why we're all fictional characters and like one of the things that he is forever
1:10:31
going on about is this idea that like you're you're only fooling yourself if you think like that you know right yeah like searching for certainty is just like a pool's Aaron because there there is no such thing right and he's got this great thing where he says
1:10:54
um uh crazy is a numbers game and then his conversant says what do you mean and he goes and then the conversion says you mean the more people believe it and he goes then it ain't crazy yeah right yeah so like well I also think about um
1:11:17
like Seth Godin has written about pace and he uses the example of um like if you wear a if you wear a tuxedo to a black tie wedding you had good taste but if you wear a tuxedo to um you know some casual to the beach you had bad taste so it's
1:11:43
and this the idea of perfection is like by whose who is the odd like I often think if when people post on Twitter about how AI made this great image um I think like great it like by whose opinion um like who's judging it
1:12:10
um and and I would add did AI make it or did the person working right AI make it who prompted it to to do what it made that that is the art exactly yeah completely agree right it's the human operating eight listen AI is a tool that's what it is it's a great [ __ ] tool
1:12:36
and a very powerful tool but it is a tool we human beings are tool makers we always have been still there is no Steel in nature steel came out of the minds of a human yeah right right right and like
1:12:50
everything surrounding us right now came out of our minds right cumulative cultural Evolution yay because everything that that defines the world around us right now came out of basically the
1:13:06
human mind yes have you seen the the Steve Jobs thing about the bicycle of the mind yes uh I think that's that's when I first came across that a few months ago and I thought this is the greatest analogy for for AI that I've I've come across completely agreed it is it is a very powerful
1:13:31
tool but it's a tool and it's it's like fire I I love the George Carlin thing uh where he says I'm often really curious about the person who came up with the flamethrower yeah that's because he's he says that person is like thinking you know I'd really like to
1:13:52
burn those people over there to death but I'm not close enough to them right right but the point is Right fire is incredibly useful yeah but it can also be used to burn Villages down and burn people so we didn't say no we can't have fire we invented fire departments
1:14:15
fire alarms fire extinguisher fire exits right right right right do the same thing with AI yes it's not it's not it's it's like the tech itself is neutral it's the one utilizing that Tech who's
1:14:31
going to use it for good or ill in my opinion for sure yeah I I was back to humans yes yeah um I've been reading a little bit about Henry Ford and like the pushback when he was trying to build automobiles and I realize like the reason it was so hard for people then to conceive
1:14:58
what automobiles would become is because when he was working on them there weren't things like roads or stop signs or uh traffic lights so I I often like when a new technology comes on like what what's going to be the roads and the traffic sign equivalent in this case like what what is a
1:15:20
what is going to be uh invented or the Innovations created sort of tangential to AI that that may get um make more sense to us I love that reference because you're absolutely right it's like when
1:15:40
when when the people came up with movie cameras what did they think of they thought well let's film a play because that was their reference right right right right right and yeah and and
1:15:53
like when radio um Edison was basically well I guess we could listen to sermons over radio yes yeah yeah yeah I I was reading something recently that when uh I think it was in an Edwin land biography one of David sunrose's uh favorite guys uh when he was developing
1:16:15
that uh Polaroid camera there is worry that it was going to replace painters that the photography was going to replace painting that's and I thought well maybe like AI art would just be there will be AI writing and human writing and the way that like there's painting and photography exactly a new a new uh genre of art yeah it's it's it's additive it is not does not replace and I think that the uh the thing wasn't land with Polaroid but when
1:16:55
they invented the first camera it was all of the portrait artists okay the ref like oh my God my whole living is stunned and then you know uh you you see guys like Francis Bacon selling portraits
1:17:12
for 10 million pounds right thank you I think I think they can co-exist nicely together yes yeah so what like what what about where you're at right now like what do you love what do you like me I'm not so much on loving this like what would you change about what you're doing right now
1:17:40
would you what would you do more of what would you do less of um I'm actually I'm in a pretty good spot and so I'm doing mostly the things I want to be doing so I had a conversation with Ryan like middle of last year about
1:17:55
um some I think that was not wanting to I at the time I was managing the content calendar for um for daily stoic and daily dad and his personal site um and we use convertkit to send out the daily email and I was so I had so much anxiety about logging into convertkit because it I was
1:18:19
a click away it always felt like from sending out an email to hundreds of thousands of people I just and they couldn't escape that because it because we send it out every day like once today's went
1:18:31
out now I'm worried about tomorrow's email um so I was telling him about that and he was like that's just a ridiculous thing for you to be stressed about so we we hired someone um who took over the content calendar and scheduling things in convertkit and those
1:18:47
those sorts of things and that's freed me up to do basically just the the research and writing stuff and it's it's what it allowed me to become more active with my own stuff and doing the Twitter and um all that kind of stuff so I I feel like I'm in a good spot with
1:19:07
with workload and what I'm working on um and most of my day is just reading and researching um so I that was my goal was to to move away from uh the convertkit kind of scheduling things and um we're just kind of in a spot where she the the
1:19:36
woman we hired she's kind of fully now independent and has her her head wrapped around everything and um I feel pretty good about where I'm at very cool um yeah I I think that uh it's very wise to
1:19:58
um understand that we're not good at everything and that uh like find your pain points and guess what uh one man's meat is another man's poison right and right like I like if I tried to schedule my own things like it would be Mayhem yeah literally it would be Mayhem because I'm I'm
1:20:18
a chaotic attractor in that regard yeah thank God I have somebody who's much better than me uh at that although not on this particular time because you didn't get your link on this words with her
1:20:33
um this has been a lot of fun um at the end of uh my podcast as you might know I always say we're gonna make you the emperor of the world for a day you can't kill anybody and you can't put them in re-education camps but we are going to hand you a magical microphone
1:20:52
and you're going to be able to incept all eight billion people on the planet whenever they wake up their next morning they're gonna wake up and they're gonna think that they thought of two things that they're gonna act on but they're gonna actually be inceptions from
1:21:09
you Billy what are you gonna speak into the magic microphone and accept the world's population on um to read more to to uh yeah I think just just and to find like the the love of of reading in the pursuit of interesting ideas um
1:21:39
on the second for so I'm thinking about David senra and what we were talking about as someone who has found the thing they were so clearly meant to do and I often think about that kind
1:21:53
of like alignment between the person and the work they're meant to do uh so maybe I would put everyone on that search to find to to pursue and find that thing for them um because I I I love what I love when I listen to to David is it's so clear that um he's found it
1:22:18
and like we were saying about the people that are persistent in their work um I don't think it's willpower or discipline I think it's just a pure uh love for what they're doing and it's that like alignment um so so finding that would be my second uh command I love it it's like Robert Frost one
1:22:43
of my favorite poets he he said my aim in life is to unite my vocation and avocation as my two eyes make one in sight yes yeah like that that's what I was trying to say yeah you said it but he said it
1:22:59
a little better is amazing this has been a lot of fun thank you for coming on thank you for having me Jim this was this was awesome and uh people can find you uh uh all over Twitter your newsletters um you every you you want to give the other URLs for where where people might want to look no that's probably the best two places Twitter and uh the newsletter Perfecto all right well thank you awesome thank you Jim