On this week’s Infinite Loops, strategy consultant turned writer joins me to discuss why bourgeois comfort is more conducive to writing than you think, why choice plots make for better fiction, the eyerolling prevalence of manufactured nonchalance, our shared distaste for Atlantis Bahamas, and MUCH more. We also dig into her excellent novel, The Portrait of a Mirror.
I hope you enjoy this conversation as much as I did. We’ve shared some highlights below, together with links & a full transcript. As always, if you like what you hear/read, please leave a comment or drop us a review on your provider of choice.
— Jim
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Highlights
Success is Succession
“But when I went then to boarding school in Connecticut, different world. The delta between the amount of effort and the effort to shield effort is part of what you are literally learning there because it is such a class signifier. And what classes ultimately function to do is self-perpetuate. Success is succession, as my friend Erica Robles-Anderson, a professor at NYU would say. And manufactured nonchalance is how you show that you are part of the club. And specifically it's not manufactured nonchalance, it's trying to make it as genuine-seeming as possible. And it's very hard to learn that skill. That kind of ease is a function of being raised in privilege.“
Working Hard, or Hardly Working?
“It evolves over time because what I call egoic bifurcation happens. This is where your online ego fundamentally separates from your embodied physical world ego. And we get the phenomena that we see now. There was that HBO documentary "Fake Famous" that's the perfect example of egoic bifurcation because you have people working to pretend they are at leisure, which is of course the antithesis of leisure and is actually miserable to do. So they're lying on some uncomfortable thing where just in the circumscribed shot does it look like they're relaxing at a spa or something and then they're literally lying in a parking lot. And this phenomenon of egoic bifurcation is just getting worse and worse […] you are optimizing for your digital avatar that doesn't actually exist at the expense of your one wild and precious life.”
How to Create Beautiful Art
“Success generally rests on disarming the very cognitive defense mechanisms designed to protect one's fragile psyche […] Our brains are self-protective devices and ironically, you need to tear down your cognitive protection in order to access the type of truth that makes for really good art. The kind of art that when you encounter it, you think, ‘Oh my gosh, that's so true and nobody wants to admit it.’”
Bourgeois Comfort is Good for Writing
“I'm going to be honest, I think that bourgeois comfort is highly conducive to literary art in particular because of the amount of time it takes, the stability it requires and the challenge of it. Meanwhile, so many writers fall into the trap. And this is actually one of my other tips: if you're gonna write about writing, fine, but the bar is higher. You need to be better if you're gonna be writing about writing because it's much harder to be interesting. Having some kind of other job, being a scientist, being anything, gives you stuff to write about and different games to compare between and contrast and think about.”
Books Mentioned
The Portrait of a Mirror; by Natasha Joukovsky
The novels of Jane Austen
Status Anxiety; by Alain de Botton
The Love Song of J. Alfred Prufrock (poem); by T.S. Eliot
Class: A Guide Through the American Status System; by Paul Fussell
Gödel, Escher, Bach: An Eternal Golden Braid; by Douglas R. Hofstadter
Ulysses; by James Joyce
Metamorphosis; by Franz Kafka
Beloved; by Toni Morrison
In Search of Lost Time (Remembrance of Things Past); by Marcel Proust
Collective Illusions; by Todd Rose
The Status Game; by Will Storr
Anna Karenina; by Leo Tolstoy
The Theory of the Leisure Class; by Thorstein Veblen
A Little Life; by Hanya Yanagihara
🤖 Machine-Generated Transcript
Jim O’Shaughnessy:
Well, hello, everybody. It's Jim O’Shaughnessy with another edition of Infinite Loops. I am so thrilled today to welcome Natasha Joukovsky, who has worked in such interesting areas. You've straddled two very different worlds. You worked for years in the art world, where you were at the Philadelphia Museum of Art and at the Metropolitan here in New York. Then you moved on to strategy consulting and, in the few hours that you had available to you, managed to publish a debut novel, "The Portrait of a Mirror," in 2021. You also write nonfiction. And as art mirrors life, you also are the patent holder and inventor of a recursive estimation algorithm. Now you're speaking my language. Hard at work on a new novel. Natasha, welcome.
Natasha Joukovsky:
Thank you so much for having me.
Jim O’Shaughnessy:
I gotta tell you're very, very impressive. Let's talk a bit about, before we get into your first book, how do you straddle these two very different worlds? Keeping in mind that we're going to talk a lot about the unspoken game rules and all of that, they're very different in the art world and the world of consulting and commerce.
Natasha Joukovsky:
You can do everything, just not at the same time. I never worked in consulting in the art world at the same time. I fully switched careers in about 2014 after I finished business school. But then with the novel stuff, with the other stuff, it's three words: leave of absence. I'm very fortunate to work for a company that is large enough with diversity of folks trying to do a huge number of different things that they have a really good program for leaves of absence. I've taken advantage of basically all of them at this point.
Natasha Joukovsky:
I think I did, you can do up to a year unprotected, which I did in 2016, bought one-way tickets to Europe with my husband and that's where I wrote the bulk of "The Portrait of a Mirror." Of course they have maternity/paternity leave. I wrote a lot of the end of my first novel on maternity leave with my son sleeping right next to me. And I took a future leave, which is more like a sabbatical, a protected three-month leave to write the bulk of my new book, which I can't talk about quite yet.
Jim O’Shaughnessy:
But I'm going to tease a couple of at least spoilers.
Natasha Joukovsky:
We can do teasers, yes, teasers, no spoilers. I'm hoping to be able to say more very soon.
Jim O’Shaughnessy:
I'm working on my first novel myself as well.
Natasha Joukovsky:
Oh, what's your novel about?
Jim O’Shaughnessy:
Oh my God. No, no, no. I can't even tease it. But it is so interesting to me though, having written four nonfiction books that all focused on investing, etc. Boy, fiction writing is a whole lot different.
Natasha Joukovsky:
Do you think fiction's harder?
Jim O’Shaughnessy:
Yes, I think fiction's so much harder. But do you also think it's more fun?
Natasha Joukovsky:
Absolutely. No question.
Jim O’Shaughnessy:
Absolutely. It is much more fun. But it is much harder and it's just a wonderful experiment for me. But let's talk about your book. The characters in your book might fit very comfortably into the world of consulting or into the art world. It's focused on warring desires. Which social norms do we transgress, which do we adhere to? Why do we do that? What you infer as the illogical and bizarre American etiquette norms.
Natasha Joukovsky:
Yeah.
Jim O’Shaughnessy:
So essentially you're following two well-off couples. And it seems to me themes are recursion, innovation, mythology and glamour.
Natasha Joukovsky:
You did your research.
Jim O’Shaughnessy:
I did. I'm a research junkie.
Natasha Joukovsky:
The themes came first. The novel was admittedly a vehicle for themes, a vehicle for ideas. And I don't know how familiar you are—I'm guessing a bit because of your relationship with Anna Gát—but I didn't know about René Girard yet when I was writing the book, but I had come across many of the same insights incidentally and in literature, and was writing very much in that tradition of exposing the romantic lie and the imitative nature of desire.
Jim O’Shaughnessy:
Girard, I knew a lot about because I thought his work was very helpful in trying to understand auction markets. In fact, I did a thread on Twitter using the conceit of Titanic. Remember in Titanic where Rose is buying all of the artists who go on to become the greatest masters? But at the time, everyone thought it was just junk and scribbling. And so I changed it. The ship doesn't sink, she does marry the bad guy and sets up a salon in New York City. And then I talk about mimetic desire of all the couples joining this glamorous couple. And maybe that's how the art got very important. I find it really interesting that you started with themes. I'm kind of doing the same thing with mine.
Natasha Joukovsky:
Yeah.
Jim O’Shaughnessy:
Art mirrors life. But in the real world, you have a patent on a recursive estimation algorithm, which to me kind of lives at the higher end of quant probability modeling. And yet in your book, you've turned recursion into a literary engine of doubt and self-reflection. Talk about that a little bit.
Natasha Joukovsky:
Well, we were chatting a bit before we started recording about Douglas R. Hofstadter's "Gödel, Escher, Bach." The recursive nature of reality writ large on so many different levels is a pattern that just emerged to me in many different areas. I think I knew I was interested in it before I would have known to call it recursion, probably since college and the exposure to it in the Narcissus myth of Ovid's, the stories within the stories that you have. You have the frame and the structural layer. You have all of the reflections of reflections in the layers of the art within the story of Narcissus looking at himself, but then Echo being an echo of Narcissus and the visual and auditory thing operating at all of these different levels, but the same sorts of isometric patterns.
Natasha Joukovsky:
I would say that I don't think I draw the hard lines between literary and quantitative that a lot of people do. I think that the patterns emerge in both in similar ways to me and mutually reinforce each other. I always kind of joke that studying Ulysses was more instrumental in a good consulting education than business school was. Looking at how unstructured data is composed and patterned is something I'm sure you deal with all the time in your businesses and when you're thinking about investing in something—whether the folks are tapped into these fundamental recursive patterns.
Jim O’Shaughnessy:
I have been absolutely fascinated by them for a long time, and I think that you're right. You see them in literature a lot once you're exposed to it. It's like the reticular activating system. I did an experiment on it once. You don't see things unless you've planted an instruction to see them. I was reading that and I thought, I think that's kind of bullshit. And so it gave an exercise and it said, think of something you don't see very often and write it down. And then for one day, see how many of them you see. So I thought, well, I don't see very many really green cars. I see a lot of black cars, a lot of white cars, a lot of blue cars, but I rarely see a green car. And so I wrote down green cars. And then it asked me, estimate how many you think you will see over the next 24 hours. And my estimate, I think, was five. I saw 43.
Natasha Joukovsky:
Oh my God. Well, the recursion is like that too. If you're seeing 43 rather than five green cars, recursion is just—you can't not see it everywhere in everything. It becomes the pattern of life, the fractals that you see in coastlines and even tree branches. You can't look anywhere without seeing it truly everywhere. And I think that one of the great things that "Gödel, Escher, Bach" does is show these isomorphisms so explicitly in such different realms. The realm that I think he really forgets or doesn't do justice to is the literary realm. Because if you look at Gödel is what, like 1930s?
Jim O’Shaughnessy:
Yeah, early 20th century.
Natasha Joukovsky:
Early 20th century. Escher is mid-century. Bach is 18th century. But Ovid is in the first century A.D. And not only do you see Escherian, Bachian, Gödelian patterns in the Metamorphosis in particular, but you have the multiple layers of reflection about those patterns themselves. The story of Narcissus is a story of those patterns. The story of Pygmalion is a story of those patterns. The story of Medusa is a story of those patterns. There's so many. I think it's a miss. I'm going to try and pitch a review somewhere to do a metadialogue style review of "Gödel, Escher, Bach," accusing world-historical genius Douglas R. Hofstadter of leaving Ovid out of one of the most brilliant, perfect books of all time.
Jim O’Shaughnessy:
I love that. Way to counter-signal, by the way. Excellent. "Hey, Hofstadter, the book was okay, but dude, you missed all of the literature. What is up with you?" It's so funny because, like Mandelbrot, I'm sure you're a fan of his as well.
Natasha Joukovsky:
Big fan, big fan.
Jim O’Shaughnessy:
Talk about torturing myself. I reread "Gödel, Escher, Bach" about 10 years ago. I read it first when it came out and I was young, so I was 19 and probably not really well equipped to read it. But I insisted I was going to make my way through it. And we were talking about both of our experiences of reading it. I would read a page, make notes, etc. I was very diligent and I would turn the page and I would look up and I would think, I don't think I understood a single thing he said on that last page.
Natasha Joukovsky:
But honestly, I bet you were as ready to read it as ever. When could you be ready to read it? I've been thinking about recursion and related phenomena basically nonstop for over a decade. And this book totally blew my mind. There's no way to prepare yourself. The book was in my house for 20 years because my husband picked it up in college and read it so young that he'd forgotten enough about it. I'm so mad at him that he never told me, "You have to read this book." I'm mad at everyone that I've ever met who has read this book and didn't implore me, beg me, get down on their knees saying, "You have to read this. You're going to be obsessed with it." But I just don't think that a lot of people have actually read it.
Jim O’Shaughnessy:
Yeah, we completely agree. I'm a big fan of the Dao De Jing and I often do threads on Twitter about how you can apply it to other aspects. Investing is one theme that I did many threads on. And I always knew I got into this recursive pattern where when somebody would ask me on Twitter, "Which translation should I read, Jim?" I knew two things. I knew, number one, they were never going to read the book. And number two, they were signaling. It's like just doing a cover pick of "Gödel, Escher, Bach" and putting up "currently reading."
Natasha Joukovsky:
Current read. Yeah. I don't think you should be allowed to post this book until you've read it.
Jim O’Shaughnessy:
I agree, I agree.
Natasha Joukovsky:
It's kind of like on literary Twitter, back when there was literary Twitter, there's a whole theme about not being allowed to read "Remembrance of Things Past" in public until you were at least 100 or so pages in and that it was just too cringe, too embarrassing. You had to get through a certain chunk of this in private before you were allowed to read it.
Jim O’Shaughnessy:
I will admit that I did not get through Proust's "Remembrance of Things Past." I tried.
Natasha Joukovsky:
I haven't finished it yet either.
Jim O’Shaughnessy:
I tried really hard, but I just didn't get there.
Natasha Joukovsky:
I'm on the third book. I'm not going to say that I haven't gotten there. I'm going to say I haven't gotten there yet. And that it is a book that takes a really long time to read. I've loved everything that I have read. But you also just need to be in a specific mindset and it requires, like "Gödel, Escher, Bach," 100% of your attention. And as we all know, it's getting harder and harder to give that, isn't it? But I want to go back to what you said about translations and how translation is signaling. Because there's actually a scene in "The Portrait of a Mirror" where one of the characters signals to another about their high status and erudition by specifically recommending a specific translation of "Anna Karenina."
Jim O’Shaughnessy:
So there you go.
Natasha Joukovsky:
And you know that they're never going to read it, of course, but she does because only if you're in love.
Jim O’Shaughnessy:
I think that it's really interesting because so much of your book does cover the status game, for lack of a better term—Will Storr picked that beautiful title for his bestselling book.
Natasha Joukovsky:
Yeah.
Jim O’Shaughnessy:
You've written about kind of an arms race in manufactured nonchalance. And I remember when I was preparing for this, that's kind of like one of the ways that I was raised. It was never overtly said to me—an unwritten game rule—but I got it from my parents, I got it from the rest of my family. And that was never make it look hard, always make it look easy. Which I kind of lived by for a big portion of my young life until I was really working very hard on setting up a company, etc. And I just had this insight like, this is bullshit. This is really hard. And yet I've got to continually say, "Yeah, that was nothing."
Jim O’Shaughnessy:
Why do you think that is such a unique aspect of certain classes in America where it's definitely a class thing?
Natasha Joukovsky:
It absolutely is.
Jim O’Shaughnessy:
How do you talk to me about that? Give me your thesis on that.
Natasha Joukovsky:
Well, off the cuff, it is utterly ingrained in our elite education system. My public school in central Pennsylvania, where I went until eighth grade, there was a certain level of it. It's an upper middle class, academically inclined environment around Penn State, etc. And there was some sense that maybe you wanted to make it seem like you weren't trying quite as hard. But when I went then to boarding school in Connecticut, different world, the level of the delta between the amount of effort and the effort to shield effort is part of what you are literally learning there because it is such a class signifier. And what classes ultimately function to do is self-perpetuate. Success is succession, as my friend Erica Robles Anderson, a professor at NYU would say. And that manufactured nonchalance is how you show that you are part of the club. And specifically it's not manufactured nonchalance, it's trying to make it as genuine-seeming as possible. And it's very hard to learn that skill. That kind of ease is a function of being raised in privilege. And it did not come so easy to me, coming from State College, Pennsylvania as it came to many of the kids from New York, from Boston etc. But that's probably why I worked all the harder for it.
Jim O’Shaughnessy:
Well, Alain de Botton writes about status anxiety. I don't know whether you've read my friend Rob Henderson's "Luxury Beliefs."
Natasha Joukovsky:
Yeah, I'm familiar with luxury beliefs.
Jim O’Shaughnessy:
In one view, modern meritocracy increases, at least according to de Botton, our status anxiety precisely because we're told that anyone can succeed under the merit system. "Hey, doesn't matter that you went to state school, doesn't matter where you come from, you can succeed." And that can cause a lot of anxiety to people who think, "Wait a minute, I went to an Ivy League school and a prep school." Have you read Paul Fussell's "Class"?
Natasha Joukovsky:
Oh, you better believe it. Right around the end of college. Very few books have influenced me more. I thought it was a riot. Paul Fussell's influenced my work immensely.
Jim O’Shaughnessy:
I love that book and it's kind of a guilty pleasure because he is so caustically funny, but so funny. He just nails it.
Natasha Joukovsky:
He nailed it from when was that published? In the 80s? Like 40 years ago.
Jim O’Shaughnessy:
Yeah, like 40 years ago.
Natasha Joukovsky:
Even by the time I was reading it in the late aughts, it was already outdated in some ways, but it was familiar enough. My favorite part of that book is the Living Room diagnostic. I die over it because what's really funny about that book is the whole creation of the X class gives him an out. It's a very status-conscious thing for him to do to try and remove himself from what David Brooks would go on to glob on in the early aughts around the Bobo Bohemian movement. That is very self-consciously in the Fussellian tradition of class books. But the Living Room thing I thought was hilarious. But it was also very relevant at that point in my life where I gained some social confidence, having gone to boarding school, having gone to university, feeling like I could manufacture nonchalance a little better. To go back and see, "Oh my gosh, no wonder I could eventually do it." I grew up in an upper-class living room. With old valuable paintings and lots of books and all the things even if it was in the middle of nowhere, Pennsylvania and my parents were effectively not wealthy at all, just academics and professional class folks.
Jim O’Shaughnessy:
And I think that it's just—his target which he skewers brilliantly but kind of viciously is the middle and middle upper class. And he basically says there is where a constant state of anxiety is ever present. And I love the way he sets up the nine different classes with the top out of sight as what he calls the richest or the highest class and then the bottom out of sight and basically says they're the same.
Natasha Joukovsky:
Yeah, they're the same.
Jim O’Shaughnessy:
That.
Natasha Joukovsky:
But what's so funny is he skewers the bourgeois strivers. But that actually to me is less impressive than how much he gets away with skewering the lower middle classes in ways that really would be politically incorrect these days. But everyone except for the top out of sight, bottom out of sight, and the X class, he's merciless. You almost can't imagine a book like that today.
Jim O’Shaughnessy:
It's laugh out loud funny. And there's a mid-20th century author, Stephen Potter, who wrote a series of books on gamesmanship on how to one-up the other person.
Natasha Joukovsky:
Oh, that's funny.
Jim O’Shaughnessy:
It pairs nicely with Fussell. But you're right about the way he skewers the lower class. Like the pro gap in the suit.
Natasha Joukovsky:
And the kitsch like all of the little dolls. I don't even know what they're called.
Jim O’Shaughnessy:
Gnomes.
Natasha Joukovsky:
Gnomes. The garden gnomes. And all of the kitschy stuff like unicorns and stuff. I don't know. That actually was the least relatable part of it.
Jim O’Shaughnessy:
Right.
Natasha Joukovsky:
It was hilariously funny. But I think those trends maybe turn over faster and they were gone by the time I was reading the book.
Jim O’Shaughnessy:
Whenever I recommend it, I always say, "Now you gotta understand this is a very old book and a lot of things are not gonna resonate with you because we don't have them anymore." But I'm reminded of the comedic movie "Arthur" with Dudley Moore. He plays this super rich, complete malcontent with a great sense of humor. But he's a drunk, he doesn't do anything. And so his family does an intervention on him to get him to stop drinking. And they go to AA and they're all in their little circle and somebody takes him on and says, "You know, you're just a drunk, just like all the rest of us." And Moore delivers the line perfectly. He leans back in his chair and he goes, "You know what? You're absolutely right. I am just a drunk, just like the rest of you. But unlike the rest of you, I am a drunk who knows exactly where his next drink is coming from."
Natasha Joukovsky:
You think about this a lot, though. Alcoholism is seen very differently by social class, and it is judged so much more harshly when you actually don't have the resources to support it. Early in life, it can get almost glorified as, "Oh, he's a party boy. She's so much fun." You're only fun and a party boy if you have the means to sustain your addiction. That's just one example. There are so many examples where the exact same behavior reads not just more or less offensively, but like antithetically based on your social class. At a certain point, look at the Olsen twins. You want to talk about top out of sight and bottom out of sight, they absolutely still exist. The Olsen twins can dress sometimes like crazy homeless bag ladies. And that's a $150,000 bag that they're carrying. But if somebody else was wearing that same thing, nobody's going to be putting it on vogue.com.
Jim O’Shaughnessy:
But that's also interesting to me because we have changed so much from where social status was pretty easy to signal in the physical world.
Natasha Joukovsky:
Yes.
Jim O’Shaughnessy:
Like a bespoke suit, a beautiful watch, a beautiful home, etc. But we now live so much of our life through screens, and it doesn't land. In fact, often it lands the opposite, where you get mocked. Like, if you're putting up just like the person who puts up the picture of "Gödel, Escher, Bach."
Natasha Joukovsky:
Yes. Yeah.
Jim O’Shaughnessy:
The people who are kind of really switched on just chuckle. And so you've got this disconnect between the person striving like, "Oh, I want to show the world that I can read 'Gödel, Escher, Bach'" or I can do this particular thing and then it backfires. What do you think about that?
Natasha Joukovsky:
Oh, I have a whole theory on it.
Jim O’Shaughnessy:
I would love to hear it because Veblen goods aren't the thing anymore.
Natasha Joukovsky:
Damn it, Jim, you beat me to it with Veblen! I did an addendum to Veblen a couple of years ago, "The Theory of the Leisure Class on Instagram". The central nature of my evolution is that his theory basically holds in terms of all of the phenomena—pecuniary emulation, conspicuous consumption, etc. But that the mediation of screens and particularly image-based social platforms has it skew very differently. And we can actually chart starting in 2012 the evolution of Veblenite behaviors. In 2012 there wasn't yet that much difference. It was really just pictures of the bespoke suit and the vacation and whatever. It evolves over time because what I call egoic bifurcation happens. This is where your online ego fundamentally separates from your embodied physical world ego. And we get the phenomena that we see now. There was that HBO documentary "Fake Famous" that's the perfect example of egoic bifurcation because you have people working to pretend they are at leisure, which is of course the antithesis of leisure and is actually miserable to do. So they're lying on some uncomfortable thing where just in the circumscribed shot does it look like they're relaxing at a spa or something and then they're literally lying in a parking lot. And this phenomenon of egoic bifurcation is just getting worse and worse. And if anything I think that is definitely tied to mental health problems and challenges.
Natasha Joukovsky:
We are often solutioning our lives and the status games we play—all of what de Botton and Will Storr and these guys are saying is true but it fundamentally changes when you are optimizing for your digital avatar that doesn't actually exist at the expense of your one wild and precious life. It's really crazy, but we all do it. I was so addicted to Instagram at one point when I was writing "Portrait." It's really hard not to do it. You can be extremely sophisticated in thinking about these things and still get sucked into the whole process because it's moreish and it's such an effective status mechanism. As it gets easier to fake status, status itself changes and the signifiers themselves change and evolve away from the ease of communicating status. This is where you get things like the phenomenon that I kind of end with in my post-Veblen piece where you see a lot of what I call conspicuous crap. The ultimate flex online, at least a few years ago, was like Timothy Chalamet posting a picture of his sneaker with a cup of noodles. And it gets 3 million likes. Getting that many likes for something that dumb is where the status comes from. You're effectively saying, "I am so cool that I can do the dumbest shit imaginable, like actual brain-dead kind of stuff. And you're just gonna eat it up."
Jim O’Shaughnessy:
And I think part of that is because at its core, status is associated with scarcity. And the problem is we're moving towards more and more abundance, at least of material goods. And so people are kind of at sixes and sevens for how to counter-signal like Timothy did with his ratty sneaker and whatnot. But thinking back to that emergence, I was not an Instagram guy for a long time, until my wife, who is a street photographer and has a different picture every day on her Instagram account, said, "Hey, it'd be nice if you followed me." And I thought, "Okay, I'm not an Instagram guy, but I will." And so I started on Instagram and we have a friend, Joel Meyerowitz, who is kind of the granddaddy of street photography. And we were together at dinner and he turned to me and he said, "Jim, I have to tell you, your Instagram account is my absolute favorite."
Natasha Joukovsky:
I should check out your Instagram account. I only do it on my desktop. That's my secret.
Jim O’Shaughnessy:
But you should have seen my wife's face. She looked at him and she goes, "But Joel, Jim just posts random shit all day long. That and the grandchildren. That's what Jim posts." And Joel looks at her and he goes, "That is precisely why I love it." And then we got into a conversation about authenticity. And how do you fake authenticity? Groucho Marx had that great line, if you can fake authenticity, you've got it made. I'm butchering it, but it was something like that.
Natasha Joukovsky:
Oscar Wilde has an even better one on this, which is "Naturalism is just a pose, and the most irritating one I know."
Jim O’Shaughnessy:
I love Wilde. He would have killed it on Twitter.
Natasha Joukovsky:
He would have killed it everywhere. I don't think there's any age where he wouldn't have been a celebrity. He would have been amazing on reality TV. Can you even imagine?
Jim O’Shaughnessy:
Oh, amazing. But the idea of the flipping, from the person lying at leisure and they're really lying on a sidewalk. I remember learning about people who would rent private planes for like 10-minute allotments.
Natasha Joukovsky:
I read that too. I read that it wasn't just private planes, that somebody actually set up a fake private plane that looks like a private plane for people to rent out and take their picture, which is crazy. There are also all those hacks about using a toilet seat to look like you're flying. These things are—you can't make it up. It's so crazy. And then in little ways I catch myself doing it and falling for it and having to tell myself, "Wait a minute, that's not real." It's all of it. All of it is the highlight reel. Even your grandkids, you're posting the best picture of your grandkids. Presumably it's not the one where they're crying. And maybe these things go in cycles too. Because I'm going to amend what you said about scarcity and we're getting dangerously close to my new book, so I'm going to have to be careful.
Jim O’Shaughnessy:
But I told you I was going to sneak it in.
Natasha Joukovsky:
It's not scarcity, it's rarity. Scarcity is lack of necessities. You have a scarcity of water, there's never a scarcity of diamonds. Nobody needs a diamond. You can only have scarce resources that are needs as opposed to wants. And it's rarity, not scarcity, that I think really drives a lot of status games and recursive cycles around what becomes cool and uncool and that accelerating sense of cycles as it becomes harder and harder to gatekeep signifiers and so they have to shift faster and faster in order for everybody to show their rich and cool status.
Jim O’Shaughnessy:
And yet it also bleeds downward. You had the piece on Atlantis, the hellhole that I absolutely despise in the Bahamas.
Natasha Joukovsky:
Oh my God. So you've been there too.
Jim O’Shaughnessy:
I've been there very reluctantly and against my will because of the duty to the children that my wife used to get me there. But the moment I got there, I looked at her and I went, "I hate cruise ships too."
Natasha Joukovsky:
Oh, I've never been on a big cruise ship.
Jim O’Shaughnessy:
I've never been on one of the big ones, but I just hate them, just looking at them. And I get to Atlantis and they clap that little wristband on you.
Natasha Joukovsky:
Oh God, I know, the colored wristband.
Jim O’Shaughnessy:
And literally I looked at my wife and I said, "You have brought me to a cruise ship on land."
Natasha Joukovsky:
I died with some of the theming like where the Trojan horse is on top of the child area. I could not deal with that place. At the same time, my husband was like, "We've got to practice taking our son," who was 4 or 5 at the time. "We're about to go on some big trips like Japan and Scandinavia. This is going to be our trial run to start traveling and being people again." And I was like, "Okay." But then I negotiated. I was like, "If we go to this place, you better book the nicest thing, the nicest part of it." And then I will admit that when they slapped the wristband on my hand, I was like, "I have the best wristband. I'm in the least shitty circle of hell."
Jim O’Shaughnessy:
I like your optimistic attitude towards that, but my wife is just like, "All right, just stop. You're not going to ruin this trip. And what I want you to do, Jim, is just take your notebook and sit by a pool and do your anthropological expedition." And that's what I did.
Natasha Joukovsky:
You can't though, because at least you can only do it from like 9 to 10:30am because at 10:30am even the adults-only pool starts getting rowdy. You can't even read at that pool. This is part of what my husband sold me on. He's like, "There's an adults-only pool. You'll be able to sit there and read while Dorian's in child care." And that's what I got sold on. And then it was like this third-rate Miami club. I couldn't handle it.
Jim O’Shaughnessy:
It's the same reason that I hate Las Vegas. It's basically just a monument to ersatz and being false. I used to have to give a lot of speeches in Las Vegas when I was in asset management and they would do big conferences there. I would always stay at a hotel that did not have a casino. In my day, it was the Four Seasons. But when I was wandering through one of the places where I was speaking, it had a huge casino. And I recommend it, actually, because if you want to see a perfectly tuned Potemkin village of persuasion, go onto the floor of a casino. You'll notice there are no clocks. They take time away. The slot machines close to the entrance are rigged to pay off bigger than the ones inside the casino. So it gives the illusion to people coming in that, "Oh my God, look at how easy it is to win." It could be a master class in trying to persuade people to get them to give you all their money.
Natasha Joukovsky:
Yeah, we had to walk through one in Atlantis. They have one in Atlantis.
Jim O’Shaughnessy:
Yes, they do. Well, it wouldn't be Atlantis without one.
Natasha Joukovsky:
It wouldn't be.
Jim O’Shaughnessy:
My parents had a tiny villa on an out island in the Bahamas on Abaco. And nobody went there at all. And our neighbors down there loved that fact. They loved the fact that nobody was there. And then the owners of the hotel and complex tried to get cruise ships to come in. And I remember I was a teenager, but I still remember the conversation. The woman's name was Frankie Corbett, and she was talking with my mom, and she was very irate. Because she called the people who came off the cruise ship "package people." And then she turned to my mom and she goes, "Free drinks ruin everything."
Natasha Joukovsky:
Don't get her to sponsor your wedding, man.
Jim O’Shaughnessy:
Well, she was an old school New England type. But I always loved that line because there's a lot of truth to it.
Natasha Joukovsky:
What are they doing in the casino too? They ply you with free drinks.
Jim O’Shaughnessy:
Absolutely.
Natasha Joukovsky:
As long as you're gambling, you get to drink however much you want.
Jim O’Shaughnessy:
And of course, it also has a very definable objective.
Natasha Joukovsky:
Yeah.
Jim O’Shaughnessy:
Get you drunk because you're gonna play any of those games much less well when you're drunk than when you are concentrating and sober.
Natasha Joukovsky:
And for longer.
Jim O’Shaughnessy:
And for longer. Let's shift gears to choice plot versus no-choice plot.
Natasha Joukovsky:
Yeah, one of my favorites.
Jim O’Shaughnessy:
Let's talk a bit about that and bring in, are the streaming algos that we now face today flattening out the various literary forms? First off, tell our listeners and viewers what you mean by choice plot versus no-choicr plot, and then we'll talk about the effect of the algos. Are they maybe turning the modern world into a no-choice plot?
Natasha Joukovsky:
At least behind the scenes, I think that there's a lot of evidence that they are. But first, to start with what I mean by the choice plot and no-choice plot. A couple years ago now, Parul Sehgal had a great piece in the New Yorker against the trauma plot. And she talks about the trauma plot versus the marriage plot. This piece had me thinking for a long time, even more broadly because what it was, was Toni Morrison. I could not wrap my head around why I loved her books and why "Beloved" was one of my favorite books versus the general trend and how much I don't like trauma literature and prefer marriage plot literature. And Morrison seemed to be such an exception. There's so much trauma in her books, and yet they are amazing. What I realized is when I think about what I really like versus don't like in novels, it's not just about is there marriage structurally or is there trauma structurally. It's a slightly broader category around the level of agency that the characters have as they move through the world of the novel.
Natasha Joukovsky:
Most marriage plot novels are choice plot novels and most trauma plot novels are no-choice plot novels. But there are exceptions. And when I was looking for a framework that better aligned with my own literary tastes, it couldn't just be sentence level because I'll take my least favorite book ever, "A Little Life." Very good on the sentence level. And yet I think it's just a steaming pile of garbage. And it comes down to not that it's traumatic so much as that just no one makes any choices. This poor character is just brutally, pedophilically raped over and over again. That's the whole novel. And the problem with the no-choice plot isn't that it's traumatic per se, it's that without choice, it's boring. Because choices are interesting. If you have no agency, where does the tension come from? So that's really what I landed on.
Natasha Joukovsky:
Of course, I need strong sentence-level writing to enjoy a book too, but it's a necessary condition, not a sufficient one. And I fundamentally gravitate toward novels where the characters have some sort of agency. I'll talk about "Beloved" again because you may look at that as like, "What do you mean? There's so much out of her control." Yeah. But the novel hinges around the last choice, the most difficult choice that Sethe has. And it's heart-wrenching because she has to make it because only she can make this choice, and she does. And thus she has no one to blame as Beloved comes back and all these things happen but herself. And it's tied to her own, the one voluntary action she had left.
Jim O’Shaughnessy:
I agree entirely on the idea of agency being interesting. I long ago kind of took the idea that I'm just going to decide once and for all that I am responsible for everything that happens to me. A ridiculous idea, because I'm not. But it really helped me because it stopped me from ever blaming other people. When something goes wrong, the tendency to want to push it off and say it's somebody else's fault is just almost overwhelming. And so I just decided I am going to act as if I am responsible for everything that happens to me, good and bad. And it really offers you actually, oddly, a much broader menu of options because you're like, "Okay, if I'm responsible, I've got to take this, I've got to really think this out. I've got to really learn from all these screw-ups and mistakes and everything else." But the idea of agency being much more interesting—it's like if you're reading something where there are no choices and it's just this horrible situation. I mean, it's kind of like Kafka's "Metamorphosis."
Natasha Joukovsky:
Well, that's, to me, that's probably the least bad.
Jim O’Shaughnessy:
Right.
Natasha Joukovsky:
This is actually a very elegant story.
Jim O’Shaughnessy:
It's a beautiful story. By the way, it might be apocryphal, but I don't think it is. I think it's been verified through letters and everything. Do you know that he wanted to have his friend burn everything he wrote?
Natasha Joukovsky:
Yeah, I've heard that.
Jim O’Shaughnessy:
And oh my God, that friend had agency and didn't do it.
Natasha Joukovsky:
I also think it's the kind of thing that you don't say to someone if you really want them to do it. If you want your stuff burned, you burn it. You don't tell somebody else to do it. That's part of the status posturing.
Jim O’Shaughnessy:
I think that's a great point. That's a really great point. So it's like, wink, nudge, nudge. "Yeah, burn my stuff."
Natasha Joukovsky:
"Burn my stuff."
Jim O’Shaughnessy:
"No, don't." And then the guy goes to get the matches in the next scene. "No, no."
Natasha Joukovsky:
"I wasn't serious."
Jim O’Shaughnessy:
"I wasn't serious. You're crazy." But what advice would you give to an aspiring novelist who, to paraphrase Eliot, in "The Love Song of J. Alfred Prufrock," "I shall come back and tell you all. I shall tell you all." And then he ends it with the woman saying, "That's not what I meant at all." What tip would you give somebody who is really trying to serve beauty and truth but has something that they want to convey, has some moral conviction that they want to convey. Is it possible?
Natasha Joukovsky:
I actually don't know because I was really interested in what you said about always taking the forced misconception that you are in control of everything and giving yourself that illusion. On negative things, on things that damage our egos, we are psychologically hardwired to try and blame everybody else. So I think that my technique is probably a little bit different than yours in that I do the exact same thing on stuff that's unflattering to me. On the unflattering stuff, I try very hard to actively counteract that bias and overtake because I know that I'm going to give myself an out and think, "Actually, no, you have more to do with that than you'd probably like to admit." But on the other side, I actually do the opposite because we're psychologically hardwired to think that everything that we do well and every success is due to our greatness rather than any sort of luck. So on that side, I actually tend to attribute success to luck.
Jim O’Shaughnessy:
Oh yeah, I should amend my statement because I do that as well.
Natasha Joukovsky:
Yeah.
Jim O’Shaughnessy:
Harry Truman said, "If you don't mind who gets the credit, it's amazing what you can accomplish."
Natasha Joukovsky:
It really is.
Jim O’Shaughnessy:
And one of my favorite thinkers, Lao Tzu, talks about the best rulers being those where the people don't believe they have a ruler at all, where the people say, "We did it ourselves." And he puts the worst ruler as the one who rules through fear and intimidation. And then the next is the one who takes credit for everything. And then the next is one who tries to be loved. But the best ruler, the absolute best ruler, is that which makes the people think, "We did that ourselves." So I'll amend. Yes, I do actually apply it the same way you do.
Natasha Joukovsky:
I wonder if you do this at your companies, but I am really big on self-organizing teams and the really flat agile structures that structurally allow best for that sort of thinking to take hold.
Jim O’Shaughnessy:
That is exactly how we organize everything at O'Shaughnessy Ventures.
Natasha Joukovsky:
I'm not surprised. I'm always trying to do that on every one of my work teams. But to answer your question on my advice to an aspiring novelist with this challenge, I actually have a whole set of 10 of these things that Lit Hub published a couple of years ago for the aspiring aesthetic novelist. But it is number one on the list. Success generally rests on disarming the very cognitive defense mechanisms designed to protect one's fragile psyche. So the ones that we've already talked about are among them. But there are more too. Our brains are self-protective devices and ironically, you need to tear down your cognitive protection in order to access the type of truth that makes for really good art. The kind of art that when you encounter it, you think, "Oh my gosh, that's so true and nobody wants to admit it." So much of the greatest literature is about mimetic desire. All of Girard's insights would count among these things. Things that we just don't like to admit exist.
Natasha Joukovsky:
So many of our problems are based on the fact that we can't even admit as people that we care about positionality and positional status more than absolute benefit. And so when we're trying to solve systemic problems like how to do taxation or big, naughty, hard things, we can't even frame the problem correctly because we're unwilling to admit the basic things about how our own brains work.
Jim O’Shaughnessy:
That is beautifully put and I completely concur. It is one of the biggest challenges. I faced it personally. I always believed that I had escaped the status hierarchy and that I was not signaling. And then I got to know Will Storr and I read all of his books and I got to know Rob and I read all of his writings and then I thought to myself, "Oh, I'm signaling all the time."
Natasha Joukovsky:
All the time, all the time. I was fascinated by the way I think you were talking to Alex Danco about the whole not name-dropping Harvard game. That is deeply related to that and the number of recursive layers that get between this. Your defense mechanisms are on top of defense mechanisms are on top of defense mechanisms. So it's like, "I don't want to signal that I went to Harvard, but I want to signal that I went to Harvard. I don't want to use the word but." So that in and of itself is this loop of self-deception around what somebody is doing. But you have to admit, "I want the other person to know that I went to Harvard because it is high status, and status is important to me." And status, like anything that is so basic, it's really not that embarrassing because no one is immune from status.
Jim O’Shaughnessy:
No.
Natasha Joukovsky:
Some people are better at manufacturing nonchalance than others. I have a line in "Portrait" about one of the characters almost passing the Turing test. The most impressive aspect of her algorithm being the inability to see that the algorithm was there. Some people are really good at hiding it. Sometimes it comes close to crossing into second nature, but almost everyone is interested in status. We are social creatures.
Jim O’Shaughnessy:
We definitely are. And it was talking with Will and reading all of his stuff who finally convinced me. I'm like, "Okay, I surrender. You're right, Will." And the whole Harvard thing—another thing that works really well on all of these misconceptions and misperceptions is humor.
Natasha Joukovsky:
Oh, humor is the best.
Jim O’Shaughnessy:
So I immediately thought when you were talking about Harvard of the joke: a Texan who went to Harvard doesn't know which to mention first.
Natasha Joukovsky:
Exactly. And this goes to the fact—why Paul Fussell, we don't mind. We can take it when there's humor in it. It makes it so much more palatable. Now, better yet, if it's both humorous and there is an obscuring layer that allows us to still keep our own ego out of it. So my friend Luke Burgis has this great example of "Seinfeld" that the reason "Seinfeld" is so popular is because they're taking advantage of all the underlying natures and mechanics of mimetic desire, but they're doing so in such a way that you're laughing at rather than with them, and yourself can have the satisfaction of saying, "Oh, how silly. That's a them problem."
Jim O’Shaughnessy:
Yeah.
Natasha Joukovsky:
"I've seen this in so many other people, but not me." Whereas, you get into some of the other stuff, you get into Proust, for instance, and there it becomes much, much harder to divorce yourself from the insights that you're seeing in Marcel.
Jim O’Shaughnessy:
And the other thing that ties into is something that I got worried about around 2013-2014, about what I was noticing, especially in younger people, was basically presenting things that they did not believe in as if they did. So falsifying their preferences. And falsifying their preferences because they were worried that if they were honest about their true preference, revealed preference, that they would be in some way excommunicated from the group. Todd Rose wrote a really good book about this called "Collective Illusions," where it's like, if you believe that everybody believes something, you're going to go along even if everybody's just faking it, even if everyone doesn't believe that. And that can lead to some really bad outcomes.
Natasha Joukovsky:
They have the academic psychological studies to prove this. All of those studies where it turns out that the group is brought in and to the one person who is a subject, it seems that all five or six of the people are subjects. And then you have two lines and publicly the five people have to say, are they the same length or different, which one is longer? And very often, I don't know, it's like ⅓ or ¾ of the time, the one subject who's not in on the joke will join the group with the obviously empirically wrong answer.
Jim O’Shaughnessy:
And what I find interesting about that is it gets back to how do you determine if somebody is a high agency person. They're the person who—and low in agreeability if you're bringing the Big Five in. It's like the whole mimetic Girardian idea. I'm very interested in the person who throws the first stone. That's the person I want to figure out because they are the one that allows all of the other stone throwers to let them have it.
Natasha Joukovsky:
Oh yeah.
Jim O’Shaughnessy:
But we mostly copy. And Robert Anton Wilson has written extensively about this kind of riffing on the idea of reality tunnels. We all see the world very differently. And then he gets into game rules, that unspoken thing that we all know is there. But different people play that game better. Basically, the person who has no fluency in being able to infer what the game rules are is gonna appear pretty stupid to the people around them.
Natasha Joukovsky:
Yeah.
Jim O’Shaughnessy:
And yet he gives examples like in driving. That's an easy one. Obviously there are official traffic rules. You stop at the red light, you give way on the yield. But there's a whole host of unwritten driving rules. The letting somebody come in, the thank you wave, all of that can cause huge road rage if you violate them. Office politics, being reasonable, all these things are separate reality tunnels kind of clashing. And then he has this great line where he says, what it does is it makes it very difficult for people to have actual substantive communication and conversation with one another. And the way he puts it is, if I'm a dog and I say woof to you and you're a cat and you go meow, we're both going to think the other one's a bit dumb and we're really not going to be able to communicate. And we're going to make assumptions that simply are not true simply because a dog doesn't speak cat or a cat doesn't speak dog. And I saw a lot of that in your work, kind of the game rules.
Natasha Joukovsky:
Oh, yeah.
Jim O’Shaughnessy:
Like one of your characters, I think it was Dale, who, your characters in certain parts of the book treat their romantic partners like college admissions.
Natasha Joukovsky:
Oh, yeah.
Jim O’Shaughnessy:
Dale is Vivian's backup, right?
Natasha Joukovsky:
Yeah, yeah.
Jim O’Shaughnessy:
And it's like, what's your backup here? So let's get back to the differences because I'm fascinated by the fact that you live in two really different worlds.
Natasha Joukovsky:
That's actually what I was going to relate it to. And this is relevant to the novel too, because I bring both of those worlds in. But one of the things that I'm really interested in, kind of industry to industry, is what the points are and how that changes. In so many ways, business is way more simple because the dollars are the points. They're material, they're easily quantifiable. We all have a shared understanding of what they mean. Money is a really successful cultural story that has been very successful. It's killed it over history. And part of the reason is because it's so easy because it's so clear.
Natasha Joukovsky:
So that side of things is less interesting in many ways just because it kind of is what it is. When you get into the prestige industries, which I experienced firsthand in the big museums, but also in publishing, it's really interesting because the dollars are no longer the points. The points are metaphysical, they are difficult to understand. And oftentimes you need to be getting dollars from somewhere else even to play. So they are two totally different games governed by different social rules that have varying amounts of respect for each other.
Natasha Joukovsky:
One of the most interesting things that I found, which you may appreciate, is that in my day job and consulting job, my boss and my co-workers are way more interested and supportive of my literary career than I think the publishing industry is. I think it's very much looked down upon as a kind of sellout move. Like nobody wants the consultant to publish a book over the people who have given their lives and sacrificed their material well-being for this great work.
Natasha Joukovsky:
But I'm going to be honest, I think that bourgeois comfort is highly conducive to literary art in particular because of the amount of time it takes, the stability it requires and the challenge of it. Meanwhile, so many writers fall into the trap. And this is actually one of my other tips: if you're gonna write about writing, fine, but the bar is higher. You need to be better if you're gonna be writing about writing because it's much harder to be interesting. Having some kind of other job, being a scientist, being anything, gives you stuff to write about and different games to compare between and contrast and think about.
Natasha Joukovsky:
So I think operating in multiple worlds in both a materially and a metaphysically driven industry at once has been very helpful for me in thinking about the ideas that drive my fiction a lot of the time.
Jim O’Shaughnessy:
I agree. Many high-achieving people kind of have portfolios of status games, and that many times causes envy, because they're like, "You're this great consultant, you write great literary fiction, you're pretty, you're stable, you're all of these things." And then you can feel the envy. But I definitely think that you're onto something because you're right. The trope of the artist starving in a garret somewhere doesn't really work. Van Gogh, he didn't have an easy life.
Natasha Joukovsky:
He also was a visual artist, which is, again, the medium is different. I say literary art specifically.
Jim O’Shaughnessy:
I know, I know.
Natasha Joukovsky:
Within literary arts, though, the starving artist archetype is a much better fit for poet than a novelist.
Jim O’Shaughnessy:
Totally agree.
Natasha Joukovsky:
You can write a beautiful poem in an afternoon and being there for the inspiration in your garret. I don't necessarily think that poverty is particularly at odds with great poetry and maybe it's even conducive to it, but good Lord, unless you're Jack Kerouac and I know precious few people who actually write this way, where you're just kind of streaming and going very fast. The stability is part of it. I can speak at least for myself, when I am able to work full time on one of my leaves of absence that I so wonderfully get to take, it's just so much easier. When you have those big chunks of time, the leisure—it's conducive to working. I think a lot of what Cal Newport talks about in slow productivity. Jane Austen's his first example in that book. And it's totally apocryphal that she was scribbling in between her social obligations. No, she had these set periods of massive amounts of leisure, and she crushed it during those times and then often went years without writing much. She had a really difficult period in Bath where she was barely writing at all.
Natasha Joukovsky:
And I'm sure you've seen this too, with all of the hats that you wear as an investor and as an author, etc. You're not necessarily writing all the time. Over how many years have you written your four books? I would imagine that you weren't always in the act of writing one. Even in my last two books, 80% of my most recent novel was written in my three-month leave of absence where I was spending 14 hours a day on it.
Jim O’Shaughnessy:
The luxury of having time to concentrate, time to really do deeper work is, at least in my experience, necessary. And because I had in most instances my own companies that I'd founded, I could say, "Yeah, Jim, you can take that 90 days off." But it is really something that has to be there. And I'm very fascinated by the pretense that these various social systems that collide with one another have. They have different pretenses. Like in the literary one, there's a lot of "How dare you? You can't have a bestselling book. You're a money manager. You can't do that."
Jim O’Shaughnessy:
And yet over in the world of asset management, they're like, "Huh, maybe I should write a book too."
Natasha Joukovsky:
I think that part of it is, it goes to rarity too. As lofty as we tend to think of asset management or high-end consulting or investment banking as being, it is infinitely easier to get one of those jobs than to publish a novel. It's not in the same realm. They're rare in a certain sense. I mean, it's still not easy, but it's not that hard. Most people, if you really want to be a management consultant and you are willing to put in the effort and go listen to Victor Cheng for 100 hours before your case interviews, most people could probably do it.
Natasha Joukovsky:
I think the vast majority of people could work their whole lives and never write a good book.
Jim O’Shaughnessy:
Oh, totally. I couldn't agree more. It's much harder. I love the rarity concept. That's a better way to look at it than scarcity, as I'm thinking about it. Much better actually. So thank you for that. I will definitely steal that from you. Before we go though, I'm just gonna touch on your new book because we don't want to give spoilers, just teasers. Your new book is about probability, basketball and narrative illusion. Tease it a little bit for what people can look forward to.
Natasha Joukovsky:
It is another—well, my first book was a modern reinterpretation of the myth of Narcissus, the new one is a modern reinterpretation of two myths. It is the story of a modern Icarus as narrated by a modern Cassandra.
Jim O’Shaughnessy:
I love that.
Natasha Joukovsky:
I was really tickled by the idea of—I never thought I would write a first-person novel, to be honest. I'm very of the Austenian tradition. She's the voice in my head, the reason I wanted to be an author, etc., and my first book was very much in her 19th century third person. But I was really tickled by the idea of an omniscient first-person narrator. I just thought it was funny.
Natasha Joukovsky:
And so I had an idea for a Cassandra novel and I had an idea for an Icarus novel and as happened to me with "Portrait" too, I really realized I had an idea when I realized that those two novels were actually one novel and that Cassandra needed to tell the story of Icarus. But I think all three of them, all three of the myths that I've been really drawn to, to the level of wanting to put a whole book around, just hold up in our modern world. You talk about algorithmic determinism, for instance, and there's a lot of Cassandras running around saying this stuff. Some of that stuff makes everyone feel a little bit like Cassandra. I feel like Cassandra all the time with that stuff. And Icarus flying too close to the sun and just our world's obsession with fame and flight and status, highness, high-medium, lowness. And of course, Narcissus is probably the most obvious. I went for that one first for obvious reasons.
Natasha Joukovsky:
I mean, you start looking for—you talk about seeing something everywhere when you start looking for it. But count how many times something reminds you of the myth of Narcissus during the day, like in a single scroll through the social media platform of your choice. It's all narcissists.
Jim O’Shaughnessy:
Yeah. And it's all echo. And on Twitter there's that handle "VCs congratulating themselves."
Natasha Joukovsky:
Oh, gosh, I've never heard. I'm not very Twitter savvy. So you gotta tell me.
Jim O’Shaughnessy:
You should check it out. It's hysterical because it's kind of like the old Goldman Sachs elevator, which is just basically making tremendous fun of these people who are so tone deaf. They don't understand that they're making Narcissus look modest by comparison.
Natasha Joukovsky:
I have to think that you must to a certain extent, and I'm curious if I can ask you this, if you feel that you have a competitive advantage as a VC in the way you've expanded beyond that role with this podcast, with Infinite Books, where you're just often talking to people like my friend Julia Galef about charm. Things way outside of necessarily what somebody reading your Wikipedia article would think of as your core interests. Do you think that has given you an advantage? In terms of the novelist-consulting thing, I'm curious if you think all of your other endeavors make you better as a VC too.
Jim O’Shaughnessy:
I think that's probably true, but my origins were really in public stock management, so VC, I didn't really start doing private investing until about 2006. But definitely it has very much influenced the type of venture investing we do. For example, we love what they call pre-seed and seed. That's when things are just getting started. And we love that because it's not as crowded as sort of Series A and Series B. We're not playing in the "my brand is better than your brand," which happens a lot with the marquee Series A and Series B. And the ability to glean insights from our other verticals like films, books, social media, YouTube, Substacks, etc., is very helpful. But it also helped me understand what I'm not good at.
Jim O’Shaughnessy:
Sometimes it's really good to understand your own limitations. And I kind of suck at the Series A Series B. I'm not built like that. I'm built much more for the "Oh wow, this guy, this woman over here, she's got a great idea. Let's give her some seed money and see if it plays out." We enjoy it more. We have a lot more fun because we can actually help. And when it comes up to when the business model's been proved and every kind of thing like that, we're not going to really be of much help.
Natasha Joukovsky:
So you're avoiding the mimetic hype train.
Jim O’Shaughnessy:
Yes.
Natasha Joukovsky:
Where you get interested in something because other people are interested.
Jim O’Shaughnessy:
In fact, one of the rules that we have across all our verticals is we don't participate in auctions. Meaning, if there is an author for Infinite Books that we really love, but it's got to be an auction environment, we'll wish them well. We'll support the book even when the other publisher pays up for it. And we'll continue to support the author. But if there's an auction, we don't play. Same with VC, same with films, same everywhere. Because of the mimetic nature and because I'm a fairly competitive person.
Natasha Joukovsky:
It's hard to avoid.
Jim O’Shaughnessy:
It really is. And so I put rules in place to remind myself, "Hey, dummy, if you're gonna do that, you're gonna regret it and you'll end up not having as much fun." So we try to avoid and yet understand the mimetic nature of many markets. Literary markets, financial markets, movie markets. It plays in all of them.
Natasha Joukovsky:
Oh yeah, because it's human.
Jim O’Shaughnessy:
Exactly. And that's kind of like Will Storr's conclusion about status games, whereas de Botton basically says, "Hey, be a bohemian or do the arts or philosophy," Will just says, "We're human and we're never gonna stop playing this game."
Natasha Joukovsky:
My response to de Botton on this is interesting too because I think his position is interesting. I'm more sympathetic to some than others because I actually think that art, for instance, is a very good conduit at lessening the impact of status anxiety around just life. Because status anxiety isn't pleasant. And facing it head on and facing it in many of the conduits that de Botton recommends are actually helpful. It's that you can't fool yourself that those arenas themselves are devoid of the thing you're looking to escape. As if the art world isn't brimming with status games. Find me a more intense status game structure than the art world.
Jim O’Shaughnessy:
You can't, you can't.
Natasha Joukovsky:
Or one of his is religion, or philosophy. You think big-name philosophers aren't competitive with each other for academic status and their chairs and accolades? Dream on. It exists everywhere. So face it, realize that you can't escape it, realize no one else can either. It's not embarrassing and do your best to keep it in perspective.
Jim O’Shaughnessy:
Perfect segue to our final question.
Natasha Joukovsky:
Okay.
Jim O’Shaughnessy:
The most fun.
Natasha Joukovsky:
Me too. We have a heck of a lot in common.
Jim O’Shaughnessy:
We absolutely do. So our final question here is a little game. And that game is we're going to make you empress of the world.
Natasha Joukovsky:
Love it.
Jim O’Shaughnessy:
Only for one day. And there are two rules. You can't kill anyone and you can't put anyone in a re-education camp. But what we're gonna allow is we're gonna hand you a magic microphone and you can say two things into it that will incept the entire population on planet Earth. Whatever their next morning is, they're going to take the two things that you've incepted and they're going to say, "You know what? I so rarely act on things that are ideas to me, but I've just had two of the best ideas and I'm going to actually act on them." What two things are you going to incept into the world?
Natasha Joukovsky:
Okay, the first one, read Jane Austen. All six novels. All six of them. No better way to understand the world. And the second one's very selfish, which is read all of mine.
Jim O’Shaughnessy:
I love that. You're gonna have 8 billion copies sold.
Natasha Joukovsky:
I sure hope so.
Jim O’Shaughnessy:
Your book, what a great inception point. Natasha, this has been so much fun. Thank you so much for coming on and best of luck with the book that shall not be named, but hopefully is coming out sometime within a year maybe.
Natasha Joukovsky:
Let's sure hope. Thank you so much for having me. The pleasure was mine. What a treat.
Jim O’Shaughnessy:
The treat and pleasure were mine.
