
Writer of StartingFromNix talks beauty, multiple identities, and profiling companies
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A
Everything that you make, whether it's company, a piece of writing, a podcast, is this amalgamation of your experiences in the world, grew up, all the things you read, all of the people you've met. It's a collection of these things brought into the furnace of something and come out the other side. You really see in this very subtle moment is how a person's entire being has gone into this. Any of these very large, significant companies, you can actually trace back the lineage and the sense of affable feeling that it's come from the founder. I have multiple identities and the reason why they feel at odds is because sometimes those identities conflict or come into friction with one another. I don't know if you've read the short story Borges and I, it's about him and having a separate writer self and then himself circling around each other and, you know, one wins, but who is it? And there's always these dueling parts of me, which is one this very serious, intense side and then this more playful, light side.
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So the implication there is that it should be bridged is some separation. Good.
A
Maybe I don't have answers here. It is through seriousness that you find playfulness. Think about Miyazaki, right? He hand drew his frames until well into the 70s. There's this one amazing interview where he says, like, I was thinking about how to make the dragon move. And he's like, I actually went to a restaurant and I looked at the eels wriggling around and I thought, you ever seen an eel move like that? He just has, like constitutionally unable to not care. And I think that is what makes this film so light. And you don't have to have this tyranny of one identity.
B
Welcome to Dialectic Episode 46 with Nicole Saya. Nicole is a writer, investor and a friend who I've had many wide ranging generative conversations with. And so I was excited to be able to capture one of them with you here today. Nicole, or Nicks as you might know her from her writing, writes on substack at Starting From Nicks and just launched a new project called New Ontologies where she's profiling founders and early stage teams and the principles and ideas and craft and humanity that go into them. We talked about beauty, reality and fantasy, writing and ambition and this tension that we circle through so much of the conversation around, which is striving in seriousness and effort and intensity and also the ways that things can just fall into place when you come to love not just fantasy, but reality. I hope you enjoy the conversation and before we get into things. I'd like to thank Notion Dialectic's presenting partner. Notion is a creative workspace for your life's work and has dramatically changed in the past couple of years as they rebuilt the company from the ground up to think about how AI can be used in a way that doesn't just automate away your teammates or automate away the meaningful work, but instead allows you to think from first principles about how you can collaborate with people and with AI to do great work. The theme behind this for Notion is thinking together. As Notion has reinvented itself, the team has evolved incredibly too. My friend and former podcast guest Bree Wolfson and her collaborator Camille wrote an amazing piece for Colossus about the inside of Notion and how they're becoming an AI first company and Notion is growing incredibly fast. I have to imagine that there are a number of Dialectic listeners who would be amazing fits for Notion, whether it be on the product side, the go to market and sales teams who are totally transforming how companies work from the inside out across collaboration with AI and a team that I spend a lot of time with, the storytelling team, as they think about the future of Notion's brand, how Notion can tell amazing stories about people building inside and outside of software across creativity, and how teams big and small are thinking together. If you think that might be you and you're interested in working with Notion, please reach out either to them directly or to me@workaxandall.com and I'll take a look. It would be a true honor to have some of my audience join the team at Notion and get to collaborate together. Notion is a huge part of what makes Dialectic possible. You can also learn more about Notion or check it out if you haven't tried it in a while@notion.com dialectic. Thanks again to Notion and here is my conversation with Nicole Saya. Nicole Saya, thank you for joining me. This is a long time coming.
A
Yeah, I'm excited to be here.
B
I'm excited for this. We've had many long meandering walks and conversations, so I'm excited to hopefully capture a little bit of that in in hi Fi. I want to start with Beauty. I'm going to turn around a line of yours on you. How has pursuing beauty rearranged your life?
A
Yeah, I think a lot about that quote by Iris Murdoch which says that beauty is a version of unselfing. And I've always loved that term of basically beauty taking you out of yourself. And I think one part that one way beauty has rearranged My life is through reading beautiful works of literature. I think just the sentence by sentence construction is really gorgeous to me. I read a lot of translation as well, and I think that seeing the choices that the translator makes, but also the choices the author makes in parallel is something I draw a lot of inspiration from.
B
I like that you have a amazing piece on kind of like different types of beauty, and I want to get into the details on that, but I have a couple of excerpts first. And you start the point almost in this sort of like, I don't want to say it's a negative orientation, but a complicated orientation to beauty, you say? Only later I'd reflect on the sheer inescapability of my longing for beauty. Most women I know grew up haunted by the beauty myth, torn between acceptance and aspiration. All my life I saw beauty as a form of applied effort. Beauty was rarely a quality one owned intrinsically, rather something one maniacally expended money and time to become. I think this is also against the backdrop of a trip to Seoul, which is obviously a very specific place in that world. Then you go on to say, it seems to me there are two predominant types of beauty. A beauty that is solipsistic, oriented around glamour and draws us inward in an ever turning gyre, and a beauty that lies outside of us, that makes us more generous and open. The same kind of essence of that Murdoch reference you were talking about. I'm curious how you relate to this. Sort of like maybe one cut of this or one interpretation I have is like, there's a type of beauty as like a target, like to make something more beautiful, make oneself more beautiful, but certainly also effortfully make words more beautiful or a podcast more whatever. And then there's a beauty as like perception, which is like this just generous orientation towards recognizing the world is beautiful. Do you think that those two things are at odds with each other? And to the extent they're not, or to the extent they. Or like maybe what I'm asking is like, how do you think about intentionality in those two forms of beauty? Because the second one, the perception one, feels much more like I'm not doing anything and the world's just happening to me and I'm perceiving the world as beautiful. And the other feels like very effortful and we'll talk more about that and seriousness and so on. But does that distinction make any sense? I'm curious for your perspective.
A
Yeah, it does, but I mean, I think I would say that both are actually quite intentional because the second is more like Actually, oh, I'm purposefully paying attention to the world. And it's a frame of mind where I think a lot about like, ordinary magic. And, you know, there's a lot of poets that write about this and some of my favorite poetry is always like about regular people, regular days. And I think one aspect of beauty is actually noticing the ordinary and watching it come alive with a new sheen. You know, there's that Simone Whale like, attention is the greatest form of prayer. So I think they're both intentional, just maybe different frames. One is very inward oriented and the other is more external, which is I'm perceiving the world. I'm taking in these inputs and I'm making something out of that, or I'm. Or I'm anticipating or understanding something different about the world.
B
Does it take effort? Does that, does that a type of attention take effort? You relate to it taking effort?
A
I do, yeah. I mean, I do think that, well, sometimes it's like, oh, wow, this mountain range or this thing that I'm looking at is just inherently, you know, nature is beautiful.
B
Yes.
A
But I do think that some, some perception is required, like some perceptual change is required for you to also see the regular world as beautiful. Yeah.
B
There's a Nietzsche idea that you get into in the same piece, and it's almost like a. If that's like one form of two types of beauty, there's a different kind of cut on two types of beauty being sort of like easy to perceive and difficult to perceive. And Nietzsche's talking about music and like the way that some things are like, really easy to consume or really easy to access. He says we need to exercise effort and goodwill in order to endure it in spite of its strangeness. We are finally recompensed for our goodwill, our patience, reasonableness, and gentleness towards what is unfamiliar. By the unfamiliar slowly throwing off its veil and presenting itself to us anew, presenting itself to us as a new, ineffable beauty. That that is. It's thanks for our hospitality. Love too has to be learned. There's someone else you say tolerate strangeness long enough to be changed by it. And you say, I think this is also maybe you in the same piece you talk about perhaps developing a taste for difficult beauty or the ability to tolerate mental discomfort is one of the most important human skills to have. To consume novel things, to accept boredom and sadness, to be patient, to override the aversion of being changed. And so like, there's this. I'm really fascinated by this, like this tension around something being strange and having to sit with it to the point where the beauty inside of that, in it becoming beautiful. We are also changed, which I think I can. Like I've experienced. But it's so non intuitive.
A
Yeah, I mean, I think it's like the frontier of the world coming together and the unfolding that happens between you and the world, which I think we've talked about. Bunch. But, you know, there's lots of ways that. For example, Nisha talks about music. There's another piece by Zadie Smith that I really like called, you know, Attunement or on Attunement. And it's about how she hears Joni Mitchell's song California for the first time. And if you've heard California, it's a little bit of an odd song. It's not, you know, it's not naturally. It's sort of a different register, a different tempo than people maybe were used to or are used to. And she describes a moment underneath a cathedral when she hears a song and it completely flips for her. And it's about context and it's about engagement with the song in a very difficult moment in her life or a moment of reflection. And I think about that a lot for books and different types of media as well, which is. And even people. Right. It's like context matters so much. And I think sometimes we think that everything is very stable and contrived in a contrived state. So maybe you see something or read something once and it doesn't hit then. But I think it requires patience and endurance to actually look at it again, like turn over the stone again and give things second chances. I think I'm a big believer in that.
B
That's a romantic idea and a beautiful one and certainly one that I think most people will connect to, whether maybe it's not quite the same example. I had my own experience of that with Joanie, where I. I already liked Joanie, but I. I had heard Both Sides now many times and like, I was just want to walk one day. And I was. I like fully listened to it for the first time and I was like, oh my gosh, like this. This is one of the best things ever written. Which is a little different than, I think the Zadie example where she actually, like, had almost had an aversion.
A
Like an aversion. Yeah.
B
I guess my question is, like, we have finite attention. Maybe the classic example is like, you read a book or you watch a film and you don't connect with it, and years later you come back and so, like, time is doing a lot of work there. Perhaps to go back to your. The point you were making or the point I was making, a referencing of yours is that I've changed. How do you know when to, like, give something more? Assuming that some beauty is not easy, how do you know when to persist?
A
When it's challenging.
B
When it's challenging versus, like, numb or something or.
A
Yeah, we're sort of neutral. I mean, I think the, like, dispassion thing is. Is probably the signal that maybe there's nothing there. But I think if you feel that there's something there and maybe it's uncomfortable, it's like abrasive. Yeah, it's abrasive. And you're like, oh, I don't like this at all. Then maybe return to it because there's some emotional register there that you're not quite aware of.
B
Do you have. Are there any experiences of maybe art wise or otherwise that come to mind where you've had this kind of like, switch, almost like this horseshoeing?
A
Yeah, there's actually a really good example. I took art history in college, and my art teacher, she was just, I mean, fabulous professor, but she was very moved by art to the point where she would cry in the middle of our lectures. It was great. I was so energized by it, first of all. But there was this one.
B
It's a big class.
A
It's a small class seminar, but there's this big structure called Donald Judd's boxes in Marfa. And it's just like the row of boxes in the fields of like a waste, like a. Like a barren land, basically. And she started like, bawling her eyes out in the center of class. And for a long time I didn't understand it. You know, I was kind of shocked by that reaction, or almost like it's like, come on.
B
Like, are you really?
A
Are you really? But when I. There was like a moment when I looked at some photos of those boxes and there's some. The sun was setting, the light was reflecting off of it. I read the backstory of why did Donald Judd kind of put those boxes there? It's about man made versus artificial and all these interesting dualities. And I thought there was just so much more texture there that I didn't pick up the first time. And so it changed my mind, first of all, to see someone have a really emotional reaction to it. And I also think that's why we enjoy friends recommendations or we trust people to. To show us what. What also hits for them. Maybe you can kind of adjust your. Your view that way as well.
B
I wonder about this because. And it relates to something else we'll talk about. But I know a movie you like a lot is the Boy and the Heron. And it's a good example of a phenomenon that I've had many times, which is I'll experience something. The first time I saw it, I think I saw it the dub, maybe so, which is maybe a slightly different experience. Although Robert Pattinson was really going for it as the bird. And I was like, I love Miyazaki, but like, I don't really don't know what was going on there. And then I read this amazing review by David Ehrlich, who's a film critic. And then I watched the Wind Rises. And so, like, I guess the point I'm trying to illustrate is I got to. Without additional context from other people, I may have watched the Boy and the Heron years later and, like, connected it, but instead I watched the sub, like two weeks after reading this review and a few other things. And then I really connected to it and really loved it. And I had this complicated relationship where I'm like, am I cheating? Like, is the fact that I needed somebody else's additional con? I needed somebody to show me how to see. I like, I. I wonder how you relate versus There's a. Maybe a when it happens on your own, whether it's on a long time horizon or just from a. I don't know, you're going to stand in front of a painting for 10 minutes until you cry or whatever. Like, it's more earned. Like, do you think, is that. Am I just in my head about that?
A
Well, I don't know. I don't really think about sort of instinct as anything earned. I think it's earned to also spend time and engage. I mean, honestly, engage. Engaging could mean staring at something for 10 minutes or it can mean talking to people. I think of attention much more as a communal thing, where learning is a communal thing. And I think for a long time I thought of it as a very hyper individualistic endeavor. And now I'm much more open to the fact that, oh, hey, when I want to understand something or I want to learn a new concept, it's always through community. It's always through hyperlocal experiences of that thing. So I would say I think that's also earned.
B
Maybe I'm like, clinging to some sense of needing originality or something.
A
Right? Yeah.
B
Or even to go back to your communal idea, it would feel more valid, dare I use that word, to like, I'M going to talk with a few of my friends who all saw the Boy in the Heron. But if I, like, outsource an opinion from a professional, very serious person critic, it, like, again, feels. Maybe, maybe. Maybe a better way of asking this question would be, when you're doing this communally, how do you maintain sort of a sense of your own interiority or your own sense of self or ideas versus the risk maybe of like, anything you consume quickly. Trying to, like, make your thinking on that very relational is you. You don't get this aspect of sort of sitting, like, going through something on your own. Like, do you have a relationship to. Maybe it's. Maybe you're oscillating, which is. You're gonna go, I don't know. Use a simple example. Like you. You read a novel or you read a book, and then you spend some time thinking about it, and then you go to the book club and then you journal like it. It does feel that some amount of. Maybe that's what I'm trying to understand or work through is like, you want some of the relational and you want some of the isolated.
A
Yep.
B
And if you don't, and you don't want to overly rotate to one, and maybe I'm. I'm wondering about, like, how those two things blur together.
A
Right. Well, I mean, the danger point is if you actually don't feel anything toward a particular piece of work, but because everyone tells you you should feel something, you've, like, sort of labeled it as meaningful. Um, whereas, you know, if you come to that thing and you still feel something and you. And you've also talked to a bunch of other people, I think that's still a genuine appreciation of the work.
B
Yeah. It reminds me of I. I talked to Celine Wynn, who I think you know, or at least have read, and. And she reminds me of how she talks about Proust, which is like, a different cut on this would be, like, you don't have to like this for some, like, arbitrary reason that, like, you're supposed to like it. But also somebody like Celine being like, this is fun and gossipy or whatever might be a portal in for your own. Yeah, it's a really. I really love the idea that attention is actually just, like, about doing, like. Well, I almost said doing the work, putting in the time.
A
Yeah. I love Celine's work, and I think an important part about what she's doing is, like, sort of expanding the market for literature through her perception and her, you know, her sharing her perspective on things. And I do think that's Very powerful. To go back to what we were saying, which is like, okay, maybe you do need someone to guide you. And there's nothing wrong with being guided sometimes as well.
B
Right.
A
I think I take away a lot of the. I don't have any shame to, like, where I come to things, how I get to things. It's always, how do I feel about this thing at the. At the end of the day? And have I learned something along the way about myself, about the world? And I think that's a much more honest and meaningful way to come at it.
B
There's also, like, less ownership.
A
There's so much less ownership and less pressure, you know?
B
Yeah. It kind of comes back to this idea that, like, the most beautiful things. What I love about that early idea is that it actually relates a little bit. I talked with Henrik Carlson about introspection, and he has this. This Nick Cave example, and he basically talks about, like, pushing ourselves to introspect with yourself as the subject, not as the object. And it feels like beauty is something similar, which is not like, who am I? Or how can I be beautiful? Or how can I. Like, it's just like, what am I noticing? And when you take that orientation, part of what I'm sensing in a lot of your answers is just this, like, very outwardly directed orientation that thus is less concerned about whether it's your idea or somebody else's idea or any of these things.
A
Yeah, exactly.
B
I like that there's a. Maybe a related idea to beauty, which is you write about fantasy and reality and maybe the ways that we cling to fantasy when in fact reality is actually, like, far more rich or real or beautiful. Um, a couple of quick excerpts. But the characters that have captured my heart the most always chose to return to or see reality for how it was and love the deeply fought, flawed human world. Because it was real, not contrived, not airless or soundless or unbruised. It was real and had violence and rapture and bodies that aged and buildings that crumbled. But by that same hand, fervor, courage, and human striving. And then a couple other ideas I expect. When I look back on all the notes I collect this year, I'll see the inverse of fantasy. That what lasts, what feels right, looks nothing like what I first imagined or dreamed about. There are no more fantasies to cling onto. There is no past, no backward place for my longings, only forward into the night, led by the beacon of beauty, which is a really, really sweet sentiment, maybe a really almost sillily open Ended question. But how have you learned to love what is real?
A
Yeah, it's such a great question. And I think I was referring to a lot of different novels in that writing about one of my favorite sort of character arcs is like young man kind of goes for glory and victory and goes and embarks on this insane quest and through that quest realizes, hey, actually what I dreamed about and fantasized about for so long was not real. So. And I have to actually return to reality and live reality. And I'm always really interested in that inflection where you see something and you think it's real, but you realize it's
B
a mirage or it wasn't what you
A
hoped for, it wasn't what you hoped for. Right. And I think that's a very important actually life inflection point where you start to realize like, oh, the things that I dreamed about or hoped for are not coming true. But I can actually chart a new path and actually opens you up to new aperture of thinking. I think in particular, when I think about that novel or these sets of novels, fiction is always a really interesting, very extreme version of reality, which is maybe we don't go on the quest, right? We don't go on this insane quest to Wild west and all these things, but we do go on these little quests and we hope and we dream for things and there's some really fundamental truth to the fact that we don't always get what we want.
B
Yes, the texture of the story is deeply real.
A
Exactly. Yeah, exactly. And the other thing is, when I think about everything that I love and care about, whether it's, you know, a beautiful piece of work or it's a person, it's always actually the moments where they chafe against the edge of reality that I realize that they're human and they're flawed and I'm also human flawed. And that makes it deeply relatable. And so when I reflect on everything that's happened in my life, all of the actually really good moments unfolded in ways that I didn't anticipate for, didn't plan for, and maybe didn't even have the imagination for, which I think is really beautiful.
B
How do you know when you're actually encountering reality? Like much of modern life, we sort of live like a bubble wrapped existence in some sense, at least in terms of reality. In terms of stake, we don't face death very often. That's a very extreme example. Obviously there are times in life where you really get slapped in the face. You have something you desperately want and you don't get it or you lose or whatever you have the job you want. But I think in a lot of the cases, it's a little more subtle. Does that feel true to you, or does it feel like you're kind of, or maybe it's only true in hindsight. Like, I, I definitely find, like, there are, again, there are the glass shattering moments, but a lot of time it's like, I realize like a year later or something.
A
Yeah, I think they're both. I think it's both. I mean, I think there are moments where you're just really shell shocked or you're, there's moments where you're really let down by something, someone, or you just didn't get the, you didn't get the thing you wanted. And then there's other moments where, where it's only with time passing that you kind of reflect back and be like, okay, I didn't get what I wanted, but I got something far better. I think having that mindset is important. You know, I, I, I think prior to the past four years, I, I think I had a very rigid mindset of, or I'm, I'm a big planning personality.
B
Prior to the two. Until four years ago.
A
Yeah, maybe four or five years ago, whenever I started writing, I had like a very. Writing publicly, Writing publicly, I had a very big planning personality. And I think that the process is actually me learning how to not plan for things and be unexpected, be surprised by the unexpected.
B
Is that. I was going to ask, like, what is your strategy of introducing more reality? Is it that, Is it just not planning or are they. Because that's like almost a passive, like, openness to reality. Yeah, but maybe there's like, there's probably another orientation that's like, how do I. It's the Henrik line. Like, make contact.
A
Make contact with the world and make it yield something.
B
Yeah. How do you do that?
A
Yeah, I think it's saying your ideas out loud and testing them. And there's been moments where people have shut down my ideas and it's always really humbling. My gosh, it's really humbling. But in hindsight, I've always been really grateful for those moments as well, because perhaps there was some truth in them. Perhaps there was something I have yet to learn and have to incorporate into the work to make it better. Um, and so having a sort of an intellectual honesty as well is really important.
B
Well, and that often relies on, like, you have to externalize it to be totally intellectually honest. Sometimes.
A
Yes.
B
Like, it's very hard to realize you're in the fantasy world.
A
Right. It's not that thinking alone, you know.
B
Right. Right. Back to the Boy and the Heron. Like that. You. You so. Well, you make such an excellent point. Like, that's what that film is about, basically, is like the fan. The Dreamland is pretty appealing. Like. And it's almost like, why are you. Yeah. Why are you leaving? I. I think it's really easy to lull myself into believing my fantasies unless I'm forced. Like. And I. I don't know. One example is I've been fortunate to have friends who are like, back here, across the face. Oh, there's a. You. You alluded to it earlier. There's a David White quote I think we both quite like a lot. He says, whatever a human being desires for themselves will not come about exactly as they first imagined it or first laid it out in their minds. What always happens to the meeting between what you desire from your world and what the world desires of you? It's this frontier where you overhear yourself and you overhear the world. Maybe this relates to the kind of. The notion you were pointing out of, I think, exchange maybe four or five years ago with the writing. But you had said it's important, referencing that. I think it's important to overhear the world rather than narrate it in advance. And there's an element of the planning thing about that. But again, this is back to the more subtle part of it. What does it feel like to overhear the world?
A
Yeah. Well, maybe this is a naive or innocent point of view, but I do see the world as sort of benevolent and sort of narrating it internally in your head actually closes you off to any sort of external. External information or external redirection or any sort of feedback. And I think it's always dangerous when you close yourself off to feedback or you live in a sealed chamber. It's much more useful to actually see the world, talk to people. And even when you're getting bad feedback, it's actually kind of benevolent. People are telling you, you know, that something's not registering, something's not working. And, yeah, I remember this moment in art class. I used to paint a lot. We can talk about that. But before I wrote and I used to paint acrylics, and my art teacher came up behind me and was like, oh, you know, this painting, it could be so much richer and deeper if you had these different. If you added these different colors to it. And I was like, great, let me just try it out. And the art teacher came to me later and said, you're the least defensive person I've met. You just are ready to try things out. And I'm not sure if it's going to work out, but you were ready to put new colors on the painting. And I always think about that line of putting new colors on the painting as a frame in which I think to view the world.
B
Are you that way with things outside of painting or with writing?
A
Yeah, I think so. Yeah.
B
Huh. What do you think that. Does that come from that experience? Like, what have you always been like that?
A
Yeah. Maybe it's a sense of egolessness. Yeah. Or I believe in, like, it's not necessarily true that I have no ego, but, you know, I think everyone does if we're honest to ourselves. But I think trying the best to be egoless in the pursuit of beauty or in pursuit of craft I think is very important. And you have to balance that with sort of your. Your opinionation about what you should be doing as well. Of course. But there is some aspect of like, okay, don't take yourself too seriously sometimes.
B
So this is. As I was doing the prep for this, like, I was finding myself kind of continuing to swing on this pendulum, and I think this is starting to get at it, which is what you just said has this lightness and this almost like Zen, like, quality of just like, go back to, like, the reality is better than fantasy and I should just be really, really open to it and I should be loose and egoless. And yet you are a person who. And certainly someone who writes about intensity and deep effort and seriousness. There's a. There's a bit where you say beauty is effort. Effort is monstrous and ugly. But it also is the source of everything beautiful in this world and then somewhere else in writing it in life. You need to gnaw on the bone. This kind of goes back to the reality thing. Meaning get under the skin, get into the crevices. Writing has become bloodless and fake, but people crave the real. And so it's if, like, am I making up this tension? Like, it, like.
A
No, there's definitely a tension. Yeah.
B
But like, you're like that, that story about the painter. Like that would. People who don't know you very well would be like, wow, Nicole must just be like, so like L da kind of like very vibes based. Like, and we'll talk more about this later. But like, in. In some sense you're. You have a creative life primarily in writing that is probably a little bit more in that way. But still you write about Timothy Chalamet intensity and seriousness. And then you have a professional life as an investor. That's, like, much harder. Maybe it's, like, hard and soft, but, like. Yeah, that seems. Those two things seem so at odds.
A
Yeah. Well. Well, I think that you put it really well, which is, I have multiple identities, and the reason why they feel at odds is because sometimes those identities conflict or come into friction with one another. I don't know if you read the short story Borges and I. No, Borges, an Argentinian writer. I think you really like his short stories. And I. And it's about his. It's about him and having a separate writer self and then himself, and they're sort of, like, circling around each other, and, you know, one wins, but who is it?
B
Wow.
A
And I don't know. I read that, and I really related because there is these two parts, you know, and there's always this dueling parts of me, which is, you know, one. This very serious, intense side, and then this more playful, light side. And maybe disambiguating those identities has been really helpful to get at that, to separate out that tension as well.
B
Do you. Are you. Are you taking that on from almost like a Persona sense? Like, I don't know. People talk about when I'm. When I'm writing, I'll take on a Persona, or when I'm performing, I'll take on a Persona when I'm at work. Like, do you feel that duality in your. When you're at work versus when you're writing versus when you're in your. The rest of your life, or is it a little bit subtler?
A
I do feel the distinction.
B
Yeah.
A
And it's something I'm. I'm working to bridge.
B
And. And so the implication there is that it should be bridged. Like, is. Is some separation good?
A
Maybe. I mean, maybe. I. I don't have answers here. Yeah. But, yeah, I do think that there is. Maybe you can successfully have them separate. And my personal endeavor is to bridge them slightly more.
B
Yeah. I think maybe not to try to attempt to answer my own question, but it does seem that both aspects of that for you, the playfulness and the lightness and the intensity, kind of are about loving what is real. Like, they're different cuts on that maybe, but they both are in service of that, it seems.
A
Mm. Yeah. I think there's. There are a bunch of books by the German author Hermann Hesse.
B
Yeah.
A
That I love. And all his books are about duality. If you read any of them, like Siddhartha Glaspoon I've only read Siddhartha and Narcissus and Goldman. Narcissus and Goldman is probably the most relevant here. But it's about these two monks. One of them is very ascetic and lives in the tower and becomes this really intellectual and teacher professor of sorts. And the other is sort of this, you know, man of the world, goes into the world, you know, engages in acts of sensuality and violence and all of these sort of like raw things. And at the end of the novel, they come back together and have a conversation. And really, when I left that, when I read that novel, I was like, wow, like, this is us. Like, this is everyone. This is me first of all, and this is everyone I've ever known, which is, there's one part of you that's in the tower and there's one part of you in the world. And you're constantly dealing between the two. And he doesn't pass any judgment as well. It's not like, oh, one is better than the other, but one is. Each is its own integral nature. And you have to fulfill your integral nature. So maybe that's a non answer, but
B
I love that answer. I'm probably stretching here, but it reminds me a little bit of my dinner with Andre, if you've ever seen that film.
A
I haven't.
B
It's not quite the same, but it's a similar element of sort of duality and not there. It really doesn't seem that director is taking too much of an opinion, which is maybe the critical part.
A
Yeah.
B
And that certainly describes Siddhartha too. On the. On the seriousness kind of like effort, commitment thing. You have a bit where you say, when you meet someone with devotion and care for their craft, they have a thinner. They have thinner barriers between their soul and the external world. Their soul shines lightly on the surface of their being. Again, I know I'm hitting this over and over again, but like, that duality is there again, which is like. That's kind of like a surprising description of a very serious person. Like, their soul shines lightly on the surface of their being. Yeah, I think in that piece you're referencing Chalamet. This was a year ago. So when he's doing. And like, I both agree with you, but it seems so like when you think of a seriousness, it's like, yeah,
A
well, maybe my thesis is that. Maybe my thesis is. Or my unspoken thesis is that it is through seriousness that you find playfulness. Or there's. It's through seriousness that you find this level of, I guess Skating through the world. You know, like, if you think about Miyazaki, right? I write about Miyazaki a lot, and I care a lot about his work. And he's a great inspiration to me. He hand drew his frames until well into the 70s when there was all the CGI available. And there's this one amazing interview where he says, I was thinking about how to make the dragon move. And he's like, I actually went to a restaurant and I looked at the eels wriggling around, and I thought, you ever seen an eel move like that? It's amazing. And he just has, like, he's unable, constitutionally unable, to not care. And I think that is what makes this film so light and beautiful. And when you watch a Miyazaki film, it's got all these dualities inside of them too, right? There's all these children who have to grow up too early. There are these wars and famines and fires and lost children and the like. But at the end of the movie, you come away feeling like, oh, that was a beautiful, playful, light expression of art. So I think maybe my thought is that there can be both. There always is both.
B
I think you're really point. I've been wrestling with this a little bit, and it's come up in conversations where it's like, we're. We had this moment maybe that circled around the figure skater, Alyssa Liu. And it was. The whole thing was like. Like having, like the. The intense person gets crushed by the person who's having fun. It's like Djokovic. I like hitting the tennis ball. There's all these stories. I was just talking to Nick Thompson about this. This ultra runner Killian journey, I think, and he's like, everybody's pissed because he's just having a blast out there, right?
A
Yeah.
B
And this also relates to, like, find the thing that feels like play to you, that feels like work to everyone else. And I've had this conversation with a bunch of people in real life who are kind of like, but, like, how much of it should feel like play? Should it be 20%? Should it be 60%? Do other people who it feels like play to 100%? And then meanwhile, maybe it's not true for all creatives, but certainly writers. You talk to writers. Every writer's like, I hate writing, but also, it's so excruciatingly meaningful. And so I'm like, I really struggle with this. Is like, should it feel easier or should it feel intense and hard? And I think. I think your answer is, my sense is to go Back to Alyssa Lou. Like, my sense is Alyssa is someone who is deeply serious, 100%. That doesn't mean it's toxic, but it also doesn't mean it's, like, all loosey, goosey, easy all the time.
A
Right. But the expression of it is playful.
B
Yes.
A
Right. When you see her on ice, she's just clearly having so much fun. Maybe I'm projecting onto her, but also
B
because she's done the work, she put in the work.
A
Because she's done the work. And so then on ice, she can sort of relax in some ways because her body and her muscle memory is carrying her through that piece. Yeah.
B
Yeah. I mean, we could talk about this all day. The challenge, I guess, is like, I don't know if you've seen. Have you seen Miyazaki and the Heron, the documentary they most recently made about. And it's. And I'm sure it's like any of them, like, he's amazing. There's, like, There's a line in there. He's like, if we don't create, there is nothing.
A
Yeah.
B
But, like, I don't think he's having fun. Like, he is deeply burdened. And so, like, I think people usually swing to one way or the other. And that's, like, the thing that my sense is, you were right. I think Alyssa Lou on the ice for the Olympic Gold was really, truly, like, living it, present in it. Maybe that's specific to her performer or whatever. And yet I think she did the work on the interim. Maybe it's just, like, getting to the point where you're, like, able to put in all this intensity and then let yourself
A
drop the dates. Yes, exactly. Well, there's this Joan Didion. I read the Joan Didion collected interviews last week, and one of the lines I saved in there was, salvation comes from extreme and doomed commitments.
B
Write that down. And it's a banger.
A
It's such a banger. But. But also, like, you know, when. And she's asked later, there's an interview where that line is said. And later, the interviewer is like, oh, so you think it's a doom commitment? She said, no, I think it's salvation.
B
She was talking her marriage. Right.
A
I think I saw marriage, children, and writing. And so she's like, no, I think that's salvation, actually.
B
But it's both.
A
But it's both. It's both, right. It's a commitment. It's also salvation.
B
You were referencing that same bit, and you say, I've always related deeply to a romantic ethic for a while Writing was a sort of long haul dread, a seasickness that wouldn't abate even when I reached land. Do you still feel that way?
A
I go in waves. Yeah, I go in waves.
B
That's what you're talking about, right?
A
I'm sure you feel that way too. But there are moments where writing just feels effortless and easy. And there are moments where I know that, oh, I have to dig and excavate something and it's going to require some level of concentration and effort. I'm currently writing a piece about Robert Caro and sort of power broker and also his process and something I really admire. But I actually have to do the reading, which is, you know, man, it's a slog. It's a slog, but it's really meaningful.
B
Yeah, yeah. You have a. There's an old piece you wrote, I think quite old about like peaks and troughs and you're. I forget what the specific word you. Phrasing you're using, but you're talking about. It's sort of just like. Yeah, like I. One of my first guests ever, the podcast, Jason Lou, he says, confidence in the memory, success. And I think there's an element of that. It's like knowing I gotta do this vlog again. But like, I've been here before and like, I know what's good on the other side. Which maybe makes it a little easier as you progress.
A
Oh, yeah, totally.
B
Do you find that the amount of slug is pretty constant or is it. Is it. Are you getting lighter? Like, is it getting more and more easy over time?
A
It's getting easier to accept, right?
B
The paradigm. Yeah, yeah, yeah, yeah. Oh, it's funny. It's really funny. How has again, very much on the same note, but how has on the note of doomed commitments, like, how has commitment to yourself, to your writing, maybe on the note of like sort of making yourself proud, like, how have you used actually maybe a specific kind of silly reference that maybe captured. What I'm getting at is. Is you'd reference Murakami on his routine. He says the repetition itself becomes the important thing. It's a form of mesmerism. I mesmerize myself to reach a deeper state of mind. Maybe it's a simple question about habits. Maybe it's a deeper question along the lines of what you're getting at. But how have you. You're someone who has, you know, you don't write professionally at least currently, and you have a deep, deep commitment to it without some kind of super. Like, you don't have you don't write daily necessarily, you know, weekly. And yet you seem to have a real commitment to that. How does that happen? Is that. Did it start with more scaffolding and now it's lighter? Does it still have a lot of scaffolding?
A
Yeah, I think it's part of my identity now, and I think that's how all change happens, where you integrate it into part of yourself or part of your identity. It's interesting because I've been writing online publicly for four years now, but I've been writing since I was maybe like 10 years old and in lots of embarrassing outlets. I was like Wattpad, Blog Spot, WordPress, Wix, like all of these weird Tumblr, you know, I was on all these weird Internet site, like writing things, and there was always like fan fiction or fantasy and all these things. And so it's sort of a continuation of that younger child in me that was always writing. And I also wrote a pretty big poetry portfolio and thought poetry was the craft. And I still think that there are some poetic sensibilities in the writing, but they're not so condensed in form. But it is sort of a. How do you develop good faith? Right. In other people? You develop good faith by trusting that another person is going to say what they're going to do and show up at the right time and do the thing to the best of their ability. And I think that really applies to yourself, which is, how do you have good faith in yourself is that you actually do the thing you're going to say you say you're going to do. I think that's been a big contributor to continuing the writing because I've told myself I'm going to show up here and I don't want to let myself down the way I wouldn't want to let a friend down.
B
Do you have a relationship yourself with much like most things, with only writing, with some things, multiple things.
A
Writing, creativity. I'm quite serious about work as well as an investor. I'm also quite serious about fitness. So maybe those three. Yeah.
B
Creatively. You reference poetry and painting both. Are those kind of like moons circling the sun of writing or do things kind of come and go? Like, did you ever have that commitment level with painting or other things?
A
I tried. I think that there's only one, really. Maybe this is, you know, maybe it's not true because there's been a lot of artists who are multidisciplinary. But I do think if you actually want to get really good at one particular medium, it benefits you to spend More time in that medium. And painting is just a very long very. You need. You need a lot of patience to paint a lot.
B
I mean, you need a lot of patience to write a lot, too.
A
Yeah. So painting, it's just like, okay, then I have time for nothing else in my life, maybe.
B
Right. You also, you wrote a recent piece kind of referencing this Michael Nielsen idea. And this idea of. One of the questions I was. I was. I was thinking of, as you were speaking is like the good thing about commitments and good faith is that at some point it stops being like a habit or something, or something you're really trying to do, and it starts to become an identity. I am someone who writes. And yet in this kind of piece, and I think in some of what Michael's referencing, he's talking about sort of like the lightness of identity of a writer. You say when you free yourself from what Nielsen calls the tyranny of writing as primary identity, you can be free to choose for yourself what kind of writing you want to do in service your other multiple identities. Scientist, researcher, investor, designer, founder. And then you say, instead, I chose the word sustaining creative aliveness, because creative aliveness is the process of discovery, collection, synthesis, and then finally expression. And so it's funny, like, it seems like you do really have a deep identity level commitment to being a writer or being someone who writes maybe. And yet it seems, maybe even now, as we'll talk about it in a little bit, like, as your kind of creative impression, lives are converging a little bit as you like. Writing is sort of this deep identity thing, and it's this tool. Maybe, maybe the broader point here that I think you. You also get at is, like, many people silo their creative lives and their professional lives, and writing, maybe more so than painting, is easier to bring into other worlds. But yeah, it's like, it seems like you're holding this writing thing really, really firmly, but you're also, like, not needing to let it define who you like, the person you are. It's like it's still a tool.
A
Maybe. Maybe the point that we keep circling back to is that I feel that it's fine to have multiple identities, and writing can be one of those identities and in service of all these other identities, and you don't have to have this, maybe, as Michael Nielsen says, tyranny of one identity. I think when you silo yourself into one particular identity, be it, you know, maybe it's an investor, maybe it's a wr. Or whatever, then you actually close yourself off to all these Other things that you're interested in. And it's actually fine to be, you know, multifaceted and multi identity person and, and it's okay for that to be slightly illegible as well.
B
Do you think that we can form new identities or are we just like disco? Like are. Is it more like harvesting or, or inventing?
A
That's a great question, man. I don't know. I think it's harvesting. Yeah, I think it's harvesting. I think things show up early. You know, I think things show up
B
early, but we maybe neglect that you don't water that or whatever.
A
Yeah. And you don't water it.
B
Right.
A
I'm sure that there's a life in which I could have become a painter, but I chose not to become a painter.
B
Does that life feel totally gone, lost to you?
A
No, I think at some point maybe I'll harvest that identity.
B
Yeah.
A
It'd be another one in my little box.
B
Yeah, maybe that's an elegant sort of model for much of what we've been discussing, which is like there are all these sort of like seeds and things in your garden.
A
Yep.
B
And you can like spend all your time, you can like build a big wall in the middle of the garden. You can just spend your time over here. You can kind of have two kind of core parts of the garden. You can go back to things and then maybe in the, in the sort of fullness of time and maturity, you eventually you like look around and you realize it's just one card.
A
Yeah, I like that a lot. Yeah.
B
Yeah. I, I appreciate you checking me on the mo. On the identity. Clearly I'm, I'm trying to like force everything into one jumble, instinctively or otherwise. You maybe to talk about bringing things together very recently, just yesterday, two days ago launched the beginning of a new project which I think is cool to see at least an aspect of two parts of your identity come together, which is this like one. On one hand, like historically a lot of your writing is like more poetic and personal and for a long time was even synonymous. And then you have this other life which is like someone who's deeply committed to on one hand, like technology startups, but I think really like dreamers building really impressive big things, you say? I enjoy the work I do with early stage software because it's all about telling ambitious stories of technology failure reconstruction and where fantasy confronts reality markets whilst casting a romantic hope for the future. This is beautiful. I'd love to just hear about what new ontologies is, where it came from. We can talk a little Bit about Ando too in a minute. But like, what is, what is behind this and how has it felt to sort of like find this bridging in parts of your, your life?
A
Yeah, well, in sort of the tagline of neo ontologies, the website, the tagline is how do we have, how do we talk more ambitiously about the future? And when I was reflecting on that tagline or reflecting on what this project is, I thought about it as how do we access ambition at different scales? And on one scale and one way to talk about ambition is this really large moonshot vision of the future. How do we make reality malleable to our inventions? How do we, you know that quote, which is like the world is just a museum of passion projects, how do we make those projects come to life? But I am just as interested in that aspect as I am the more individual aspect of it, which is what's our personal locus of possibility and how do we expand it? And so I think where you see these things add up together is, wow, okay, I want to talk about the ambitious future, but I also care about the ambitious future in a smaller way, in a more local way, in a more community oriented way. I want people to wake up and think like, oh, hey, I can do this thing, I can push myself a little bit further. I'm living my internal and external worlds are, are congruent with each other. And I am pushing, you know, I am expanding my worldview. And I think the way I've done that personally is through conversations with friends, conversations with people, building great companies and basically an understanding that my life is very constrained and there are all these possibilities that I'm maybe not aware of. So that's maybe a long answer, but I think the point of neurontologies is to be, to show you like, hey, there's this angle of software can be incredibly empowering. And we can use software to create all these new concepts. And new ontology means sort of like new concepts of the world. And you can enter this rich intellectual world and learn a lot about it. But I also care about, as you go more granular into the individual, which is the founder or the person doing this thing. How did they get here? Why are they doing this? How can we learn from them? And so merging sort of this larger picture, ambition with this more granular ambition is maybe the goal for this project. And maybe that's a lofty goal, but it's something I've been thinking about.
B
Why do you think you're attracted to these types of stories? And clearly you've been long attracted to them, much longer than you were doing this project. I think even on some level being a venture capitalist, there's some draw there or what. What is it about like this kind of corner of the world.
A
I've always loved dreamers. I mean someone, I mean even beginning from, you know, the poetry days or you know, the writing about, you know, fiction days, it's like, oh, if you like fiction, you like dreaming, you like fiction, you like being immersed in a different world.
B
Right.
A
And I think what these founders are doing are creating these new conceptual frames of reality that are very compelling. And a lot of these frames actually become the future landscape of technology. All of these ideas actually harvest and become much larger things. And I've always been really excited about the early days, the early clay of forming things before they're fully legible and they will become legible. And so I'm just interested in that moment of change.
B
Well, it's not just legibility too. There's an element of like it's fantasy and reality.
A
Meaning. Meaning. Yeah, exactly. Maybe it goes back to that which is like oh yeah, we're always looking for when the frontier of when fantasy meets reality.
B
There's a maybe to reference Ando specifically in that piece. The first, the first kind of profile you've done on Ando and Sarah, you say her story reminded me of a Greek term I like techne, which you. I might pronouncing that wrong. Technique Techne. Yeah, it comes up all over your writing technique, which means craft grounded in practice. A founder builds a particular shape of company out of their technique, all their experiences, personal craft and taste that they bring to the work. I'd love to hear about that as a. I think your lofty answer was good. The thing that. One of the things that feels very true about your interest is to cause back to everything we talk about seriousness, but also this project specifically is that even in the like we. You and I had a conversation about this. It's in the piece like the care over linguistics and like little forms and they allude to Tadawa like all these little things like what is it? And. And maybe what, what opportunity is there to. I would expect that's a theme that will to extent you keep doing this will continue to show up in new ways. Like what is. What do you see there?
A
Yeah, well, I think that story was really compelling to me because Sarah is a second time founder and I think much of her learning in that reflection of starting a new company was I'm good at these things. But what am I truly great at? And what is my natural leverage in this world, and what's the type of company that should come out of that? Natural leverage? I don't think a lot of us actually do that really deep work, which is maybe you get pulled into things that you think you're supposed to do or other people have in mind for you. But really, what's your true talent and gift in this world? And how can you put that into practice, put that into motion? And so techne is a very beautiful term and something that I think about a lot. Another sort of related concept is what Rebecca Solnit, a writer, talks about, the cosmology of self, which is like, everything that you make, whether it's a company, a piece of writing, a podcast, is this amalgamation of your experiences in the world, you know, how you grew up, all the things you read, all of the people you've met. It's a collection of these things brought into the furnace of something and come out the other side. And she writes this line, which is like, underneath the task of writing a specific piece is making the self. Who can make the work you're meant to.
B
Yeah.
A
And I just.
B
It's like the exhaust.
A
Exactly. It's the exhaust which is like, you never look at this fully formed thing, and maybe you do, and you think it's wonderful and amazing and this fully formed asset or whatever, but actually, what you really see in this very subtle moment is how a person's entire being has gone into this thing. And I think this applies to companies. 100%. Look at any like, notion, for example, or ramp, or any of these very large significant companies are. You can actually trace back the lineage and the sense of this ineffable feeling that it's come from the founder. Right.
B
It's Apple, Steve Jobs with 10,000 lives.
A
Exactly, exactly. And you and I read Christopher Alexander, who's an architectural theorist, and one of his concepts is all these little patterns are what makes a space come alive. And all these little patterns in, like, everything that you do makes your work come alive, makes your company come alive, makes your. Yeah. Makes your. Your work more whole and more you, if that makes sense. So I'm interested in exploring that.
B
Yes. I'm going to go back to it one more time because I can't help myself. The Sarah example, second company, obviously, like, not quite the same idea, but so much of what you're just talking about is very related to, like, the ikigai, the idea of, like, how do you. How do you sort of find this convergence and that feels. Whereas previously, as I understand it, Sarah's previous company, Alloy, like, less of. But she's also like, maybe like you, like, very intense, driven striver who also cares about these other things, craft. And, and so it's my assumption is that Sarah, in her previous founding role, had more of, like, separate identities.
A
Yes.
B
And now. And so maybe I'm maybe answering my own question, but, like, on one hand, you seem okay with, like, it's okay to have different identities and you don't have to force them together. I think for any young person, it's like, how should I be trying to find the thing that is ikigai now? Or should I, like, do my creative stuff and my professional stuff and then eventually converge it? And you seem so interested, like, it's not, it's not inherently intentioned. I, I, it's not like total paradox, but it does seem that, like, maybe you're just, like, patient with the fact that there are going to be sort of dualities and at some point they'll come together, and when they come together, it's really beautiful.
A
Yeah. Well, I think it's a process of discovery. I think you find ikigai after a long route and you don't force it, and you don't have to force it. Yeah.
B
Yeah.
A
And I'm sure if you, you know, talk to any founder, they're probably like, hey, the thing that I landed on, the thing that worked, actually took a long time to get even think about artists. Like, I mean, look at Monet. I mean, I was just looking at the Monet water lily exhibition, and he painted water lilies 250 times. And it's just incredible. Right. But it's like, okay, it just took a lot of time to get right. And I think having that grace is also really important.
B
Grace is the right word. Yeah. Not only something like, it's you probably, you, you probably literally can't force the convergence.
A
Yeah.
B
I think of Robert Irwin as well, like, drawing the lines, like, just, yeah, just. And I almost wonder what, like, someone like that, maybe. I don't know if Monet did this, but he's, like, almost trying to, like, with, through so much repetition. He's just trying to, like, have the ego part of it, like, fall away. Like, that's probably the main reason we actually can't converge faster is we're just like, it's, it's your. Am I overhearing the world or am I trying to narrow it?
A
Yeah. And I think importantly, as we circle around this question of, like, okay, there's Lots of dualities, lots of identities. You can be multiple things. You can be one thing. All of these, like, you know, different things. Is that I think it's important to note that in my writing, I'm not actually trying to be prescriptive. I am trying to be a peer or, like, I'm trying to stand next to the person. And like I said, whatever is your personal locus of possibility, I want to expand that in you or, like, in the reader. And I'm not actually trying to teach someone or say, how things should be or tell you that you should merge these identities. It's more like, hey, can you walk next to me while I am, you know, trying to figure this out for myself and can we learn something together? So I. I think that's maybe the frame I'm coming from.
B
And it's interesting. I. Perhaps this is incorrect, but it reminds me a bit of Joan Didion in the way that she. I was talking to somebody this week and I was observing that, like, in Slouching Towards Bethlehem, I sort of much preferred her personal writing and notes and things to even some of the reporting. But on some level, like, she tries to convey this. Asp. Maybe this isn't exactly what you're saying. She tries to convey this aspect of, like, I'm not putting myself into this totally. Or at the very least, I'm not trying to tell you any. Like, I'm just kind of observing.
A
Yeah.
B
But in so doing, there's a huge amount of self in it. And it's like, yeah, I don't know. It really works. Well, what do you hope this becomes?
A
New ontologies? Yeah, I hope that it becomes an archive or documenting a very important time in technology. First of all, I think watching the shapes of new companies being built in this time. Well, there's some legendary companies that are going to be built in this era, and I just want to be involved in writing those stories, first of all. And then second, I hope that it touches on that ambition thing again, which is, okay, I am looking at a person creating something new. How can I, in my own life, find the agency and the hope and the ambition to do something of my own? And it doesn't have to be big, it doesn't have to be a company. But how do I actually push myself to achieve greatness or improve myself in this more personal way as well?
B
Hmm. Hmm. You go. Will make you a better investor?
A
Yes, I think so.
B
Why?
A
I think it's. Well, it's something about. So. So I guess some backdrop is, you know, I spent Almost a month with them kind of in and out of the office and lots of walks with Sarah and Uber rides and dinners and I think the, the thing that came out of it was actually just watching someone work ambiently is really important.
B
It's a different level of access.
A
It's a different level of access.
B
Almost anyone's getting it, but certainly a VC or somebody's gonna get, right?
A
And it's just. Yeah, it's a different level of, you know, I think there's always this sense of like masking in some ways when you're meeting in a very contrived state where it's like, I'm an investor and you're a founder.
B
You know, it's just like 30 minute window block of.
A
Yeah, it's like 30 minutes, you know, it's a hard stop. You know what I mean? And I don't really like. I think that the practice of actually not having hard stops is really important. You know, I've always admired people that actually go the extra mile. And an example is someone I know, a partner on the team, flew to this very remote part of Canada for this team and pretended, you know, and acted as their intern and, you know, got them coffee and donuts, you know, so it's just, it's just one of these levels where you get to know someone on a very deep and everyday level, which I guess gives you patterns or helps you understand what you're looking for in people.
B
That's cool. Do you have a call for anything? Any types of founders or companies you're looking for or is somebody who reaching out to you like you would do not want to be a part of any club that would have you as a member.
A
That's funny. No, I'm very, I mean, I'm looking for the right fit with me as well.
B
What does that mean? Maybe, I mean, I'm even curious what that means in your day job too, right?
A
Yeah, I think it's more creative leaning, a little oddball, you know, lyrical, appreciates art, thinks a lot about, you know, both the technical, technically interesting parts that I can share about the product, but also the poetic sensibilities that come with that.
B
Why is that? Not just like, that's cute but like, why does that. Do you think that has any impact on success? If we were to zoom way out and be like, okay, all the humanity, da da da. It's, it's cool that Sarah likes to dawa, but either she's going to sell enterprise SaaS or she's not, right?
A
Well, I push back a little on that because let's use Ando as an example. Ando is like a software product, but it's also in some ways a cultural product. Right. You're going to actually, if we think about Ando is an AI native Slack or a Slack built from scratch for agents. If you think about it, we spend so much time on this platform every single day and the way the notifications impact us is actually psychological, psychosocial. It's, it's, you know, it's actually like a, you know, a really interesting human aspect of it. And so much of what she's trying to do and something I really like is that she's trying to make this experience feel different. And in making something feel different and making an interface feel different, it unlocks this sort of agency or experience in a human being that is almost close to enjoyment or flow or allows you to step into creativity in a different way.
B
Certainly prevent the opposite which, which most messaging, Most messaging platforms just hijack my like.
A
Yeah.
B
Right.
A
And so I do believe that there's something there around. There's something there about like competitive differentiation which is like maybe you need a founder who actually understands culture.
B
Yes. And when there's certainly a. I love the psychosocial point. Maybe there's an always has been element of this but certainly looking forward the delineation that like the tool you use while you're at work eight hours of your day shouldn't like, like it doesn't matter as long as it's useful. It doesn't matter how it feels. Maybe that was tolerated for a long time but like it certainly doesn't seem like it will probably be tolerated for much longer.
A
Right.
B
Yeah. I'm really curious to see. I mean obviously it was partial, partially asking that question to play the devil's advocate. I'm, I'm certainly hopeful that these things matter.
A
Yeah.
B
But I also do wonder if it's a little bit romantic and maybe it depends on the, it depends on the thing like a chat apps probably is like consumer is you're going to get for a. An enterprise tool.
A
Yeah. Well the way you put it. Which is well this kind of product, you don't really do outbound sales on it. And maybe in an enterprise SaaS, if you're selling to maybe insurance carriers, that's maybe a slightly different frame.
B
Right. But why can't that be more beautiful?
A
That can also be more beautiful. Yeah. And use.
B
And now we have enough abundance.
A
Yeah, yeah, yeah. Use and beauty are not also that separate trade offs. Right. Which is like if something's more beautiful, you might use it more. And so I think there is some link there.
B
How do you think about. This is so silly, but what do you think of Amazon? Amazon is so not beautiful.
A
Right. But so useful. Ubiquity and scale is also useful, right? Yeah, but let's say. Well, let's use that example, right? Like if there's an Amazon that has the same ubiquity in scale and has the same. You can buy the same things, but it's a much more beautiful interface. Are you. Are you wedded to Amazon as a brand?
B
Right. And I don't know if I would use the word beauty, but at least effectiveness. There is a case to be made that, like you're looking the wrong thing, that Amazon's buttons don't matter. The beautiful, the beauty in that experience is that you press a button to have something appear. I don't know if it's beautiful.
A
Like, that's a. Yeah, maybe. Maybe the point is that the core of the thing is whatever it is that you're perceiving the core of the thing to be has to align with the. With the. With the pattern of distribution or something like that.
B
Yeah. I mean, to put it a different way, maybe it's like, did you. This is cliche, but like, did you truly sweat the details on the. On the part that really matters?
A
On the part that matters? Yeah.
B
Yeah, I like that a lot. I meant well. I'm very excited for the future of new ontologies. Hopefully there will be many more to come. I want to talk a little bit. I'm just curious to. You did a. And I don't know if you put any of this out publicly, but you did some work on memory earlier this year or last year? Last year. There's a specific thing that stood out to me in reading some of your notes around latent versus living memory and this idea that like you sort of frame it as like latent memory is the. Has the potential to be recalled and shared and living memory is relationally created. How does living memory change when you prompt it or activate it on your own in writing versus when. When it's actually relational? Is there a delineation there?
A
Yeah, maybe. First, to give credit to that idea, it actually comes from Kie Kruttler's work.
B
Oh, cool.
A
On artificial memory and the, you know, the reading that she's done there. And I love that so much and I, you know, used it as part of the presentation. I also talked to Kie, so just want to say that first. But her whole point Is that. Or maybe her point mixed with my point is that the study of memory that I did was two pronged. One is understanding the mediums in which writing and memory and history have changed over time and what has that done? And then the second, which is more of a like, okay, technology, what does memory mean right now? Context management thing. But if we focus back on your question, which is like, how do we think about living memory versus latent memory? I think part of it is understanding how does memory get transmitted communally. So an example of this is in the past, writing used to be on all of these different mediums, like stone, papyrus, tablet, and all of these history and words used to be moved around physically. You'd have to physically be in the room. And with the invention of things like the printing press became this dissemination of a large corpus of knowledge that you could access anywhere. And Walter ong and Marshall McLuhan kind of frame it as, okay, now you're going back into the individual. You can sit alone and reflect on the things that you've written, reflect on the things that you've done.
B
Got it.
A
And so maybe the point that I'm trying to make there is sort of like there is this one form of historical memory that was a transmission, a communal, you know, expression of memory. And then there's one where you're sitting alone in a room and sort of cogitating and, and thinking about things in the past and synthesizing them, bring them to the present, and they're just two different forms.
B
It's funny, that makes me think about like, that's happened to like most of media. Yeah. Like, I mean, it's a silly example. You think about like a film used to be this really almost spiritual experience of like, we're going to go project something on the wall of the cave. Like, we're going to project. You're going to sit in a room with a bunch of other people and project magical story on the wall. And now we sit in our beds, on our phones, privately with our private screens. There's an element of that too that I think probably extends beyond just the memory implications, which is like the. Yeah. The way that, that so much of that experience when it's commute, even when you're just looking at a phone with another person, there's like such a different experience.
A
Yeah, yeah. Well, there's this. I think you'd like this metaphor, but there was this in one of the books that I read, I'm forgetting the name. It's probably in Elizabeth Eisenstein's printing press book was this example of the cave and one of the caves, one of the historical caves that they were looking at or looking into. And I think Werner Herzog talks about this as well in his films, is that you go into the cave and it hasn't been touched. But when you do analysis on the cave, actually some of the drawings were like 10,000 years old and some were like 5,000 years old. There was a continuation of something.
B
Lineage.
A
Yeah, like a lineage. And I think that's really powerful. Right. And I think writing works this way too. Or we return to the point of, like, oh, how do we think about writing as memory? Which is that I think that writing is not a static thing. It's something that people continue to iterate on. They think about your idea and they relate back to a different idea. Like the example of, like, Michael Nielsen. Right. He wrote a piece on developing creative identity, which I remixed and said, hey, this is how I think of creative identity for myself. And so this remix culture or this more communal sense of memory is something that I'm quite interested in thinking about.
B
Do you think we're losing it?
A
Do I think we're losing it? I don't know if I'd say we're losing it. I think there's a lot more remixing happening.
B
It's true. What am I. What was my intuition pointing at there? Yeah. It feels like on one aspect of that muscle, like it's easier for anything to be rigged. Maybe. Maybe what I'm pointing out is we have, like, less collective texts, just maybe a different idea. But I'm thinking of this, like, cannon of the cave of the. Of the thing in the cave and.
A
Yeah, well, maybe if you think about it, where, look, now we have all of these AI tools, then the collection of texts or collection of prompts and responses are like, siloed in these little channels that are just between you and an AI thing.
B
Oh, I see. I thought you were going to go. I thought there's another aspect of which is actually a model trained is sort of a version of this corpus.
A
Right? Yeah, but, yeah, yeah, yeah, they're two different. They're two different orientations.
B
What is. What broadly did you learn or conclude? A ton of this work was specifically around alarms and memory. What did. And even a lot has changed in six months. I think so much of the. At least the technical side of the work was about context windows and so on and so forth. Now they're just getting bigger. But what did. What have you concluded and maybe what perspectives do you have in your personal use of memory with these tools and what's good or bad or what direction things should kind of be pushed.
A
Yeah, well, it's funny, you know, after I completed that research, it was a three month sort of project on memory, I thought, well, maybe this is going to be relevant, maybe not. And then actually, while I was writing the Ando piece, so much of Ando is context management and how do you feed the agent the right thing at the right time? How do you create new. How do you. The longer context window isn't actually better. We were thinking about retrieval and all of these different ways to make language more ergonomic for agents. And so it was funny because it was a weird recurrence where it's like, oh, dang, maybe something. Maybe things always appear when they're meant to. And so actually a lot of the learnings were extremely practical, which is. I don't think I could have understood the end of product without having done a lot of that research and understanding of context engineering from a technical standpoint, which I think is interesting itself in terms of this broader, I guess, memory as a medium kind of work that I've been doing. It's just been pushing me to think about how do I include community more in the writing, how do I continue to remix things and to make writing more open and accessible to other people such that they can remix things. And so maybe that's my orientation towards it, which is creating more open, open spaces for creativity.
B
It reminds me of Tyler Cowan talking about, like writing for the LLMs. Have you seen this?
A
No, I haven't.
B
This is like, I'm trying to, like now, I don't know, he's giving some interview and he talked about like visiting Iceland. And then later in the interview he's talking about this and he's like, yeah, now the LLMs know what I think about Iceland, which is like more useful for me, but also like, I'm like, maybe. I think what he's gesturing at is like you're kind of like bending the. Well, maybe one aspect is maybe you're influencing them, but I think maybe actually better to your point is you're. You're adding to the lineage or something.
A
Yeah, yeah, yeah, exactly.
B
And by externalizing, like as someone who's done a lot of writing, your life, most of which hasn't been public, something has changed in the way that you've contributed to this project of humanity or whatever. Like, not. Not to be overly lofty, but there is something to that, I think.
A
Yeah, it goes back to also I think distribution is important because it helps you reach that one right person for which that writing can hit them at a particular time and they can integrate it into their life. There's been so many short stories or books that I've read where I read it at a particular time, and it influenced the way that I did my work. I was telling you earlier about Robert Caro and Working, Researching and Writing is the name of his book. It's sort of like a side book because if you think of Robert Caro's books, you think like Power Broker and then LBJ and all these different books. But actually, that book was really, really instrumental in me thinking about, oh, hey, how do I go about interviewing Sarah Ando? How do I go about talking to these people? And he talks about this moment where he's sitting in the library with all of the stacks of like, back when there were files, right? He goes into this dungeon of files and he sits along the files and he and his researcher go each of the files, each of the phone books and try to call up different people. And when I read that, I was just like, dang, I'm just like not digging deep enough. I'm not gnawing on the bone hard enough. Like I need to be pushing it, right? And so I think there's like moments like that where, you know, a piece of writing can change one person's life and that's like, really has long term butterfly effects.
B
Very good reminder to the nudge towards externalizing things. I mean, yes, it ties a little something we were talking about way back in the conversation of just like. Yeah, the benefits of making something real.
A
Yeah, exactly.
B
Totally different category of thing, but something that really stood out to me. In a piece of yours, you were referencing a series of quotes from Caroline Knapp's appetites. And it's specifically kind of like a feminine cut on desire and ambition and appetite. This is Caroline. The primarily underlying striving among many women is the appetite for appetite. A longing to feel secure and safe enough to name one's true appetites and worthy and powerful enough to have them satisfied. The question of appetite, and specifically what happens to a female appetite when it is submerged and rerouted? Female appetite moves in guilty, circuitous ways. Where are the lines between satisfaction and excess, between restraint and indulgence, between pleasure and self destruction? We seem to inhabit a realm of essential sparseness, sensuality and strong emotion. Not completely absent, but muzzled and kept least in the yard. Wanting is a frightening thing, especially when you lack models for it or perm Or a sense that your desires are good, valid, insatiable.
A
It's so good.
B
Amazing. And obviously there's a specific. I'm quite interested in the specific feminine part of this, but I think there's also a meta thing which is. I talked with Henrik and I had had a few conversations recently about just like desire in general and wanting and like how often are you really letting yourself into this, like deep, almost like childlike desire. There's a version of this that I think relates to some of the seriousness and effort and that conversation. But I'm. I'm curious how you relate to this, maybe even having since read it and, and letting your appetite grow in a way that feels you feel connected to and healthy and feels like aligned versus maybe a more ravenous or ego based ambition or desire or something.
A
Yeah, I, I think that book was very instrumental in helping me understand that. If you submerge desire or you. Yeah, if you reroute it, it always just comes out in some weird way. You know, like if you're like, she's talking a lot about, you know, appetite and food in some ways, but that's the whole separate conversation. But I think in terms of allowing yourself to feel desire, allowing yourself to say, I want more than this is like, it goes back to the point of like, hey, look, like you, you grew up thinking that all of these things are inbuilt constraints and then you actually learn that they're not inbuilt constraints. I think that's like a really important thing and we've talked about before, which is like, how do you understand that you can be differently. Free. Free in different ways that you're not originally. And some of that is true, just like mere exposure to things that you're interested in. So let's say one example is for a long time I desired having friends in creative circles. I was just like, oh, I have this really interesting creative part of my life and I don't feel like I have. I'd have community there. And so much of writing the blog is being like, hey, I'm creating this community or I'm looking. It's a search query for other people who are creative. Allowing myself to express that desire is not very shameful. It's actually quite empowering. But if you don't, then there's always this feeling that you keep coming back to or it haunts you. In some ways.
B
I love that it's on the note of allowing yourself to want more. Like there's a recursive nature to this where a reflexive like my friend Steph on Go, he has this blog post, nibble on, your appetite will grow. Which is kind of like more of a general thing. But there's an element of that in this too, which is like, okay, do I want to have a creative life or do I have creative friends who are like. And could I, Am I allowed to have that? And then by the way, you write a blog post and you like, oh wow, there's people like. And it start. It compounds on itself.
A
Yes. Yeah.
B
I, I think it's like an underrated element of one of. One of. Not this whole can of worms, but like one of the underrated parts of agency. Is that it. Like it compounds?
A
Yes.
B
Like by being agentic. Makes you more agentic. Confidence is the memory success.
A
Yeah, yeah, exactly.
B
Oh yes. Yeah. It makes me wonder about what are the ways that all of us probably. What are the things I might want or desire that I've not. It's like, yeah, you're allowed to have this. But we wall ourselves off in interesting ways.
A
Yeah. Which is maybe another way to put it is like, what's the truth of the matter? What's the deep down truth? And I think we use a lot of different things to mask that deep down truth. And engaging with it in a non shameful way is actually really relieving. Like one example is I think the past few years since being in venture or having more interesting honest conversations with different people. It's like, oh, actually I could have just said the thing that was underneath the thing. What's the question under the question? Right. And oftentimes we put the question on top of the question so that, okay, eventually we're going to meander down to the question, but like, let's get to the bottom of the question and answer it.
B
It's great for everybody.
A
It's great for everything. It's great in business, it's great in personal relationships. It's just like this thing that.
B
Make it real.
A
Yeah, make it real. It just like comes back to this. Yeah.
B
You brought up differently Free. I'd love to talk about friendship. You have some amazing writing on friendship. Maybe specifically on that note, there's like a tension between. In some other place you had suggested, like your closest friend should make you feel free and safe, which is beautiful. And yet I think it's in the, in the, in the context of the differently free part. You had said relishing the company of people who sometimes make you feel by comparison, uninformed, closed to new ideas, disordered, defensive, rigid, fearful, unambitious. Is an acquired skill. It kicks up shame. It humbles you. It dares you to grow, which is. Yeah, definitely true. Like, relate to that. A beautiful part of the differently free thing. And yet, like, that can be, like, quite alienating. Sometimes being around people who are differently free doesn't make you feel more free. It makes you. It, like, it's deeply humbling. And also it almost makes you, like. Have you noticed patterns in the people who sort of ex. They're. The ways that they're differently free expands you, even if it takes a little time, versus, like, wow, the gap between us is so big, it's almost like, alienating.
A
Yeah. It's a great question. I think when I say they should humble you and dare you to grow, I don't mean that in a direct sense. They shouldn't be like, you're really bad.
B
It's more like, I. Wow, this is out there.
A
Yeah, this is out there. Like, oh, watching Jackson do his podcast inspires me that I can do a podcast. You know what I mean? Like, it's sort of. Well, I mean. I mean, I'm not there, but just by. I think inspiration through witness is what I'm talking about.
B
Yes.
A
Rather than this sort of, like, conflicting. Conflicting, more antagonistic relationship with another person.
B
Yeah. It's bringing it down to earth. Even if it's really great. Like, seeing somebody up close, as we talked about, like, seeing somebody up close does make it more real. And thus, like, on one hand, you see the amount of detail required in the effort required. But also, like, it is real.
A
Yeah.
B
It's not. It's not this imaginary.
A
Well, again, going back to the effort piece. Right. Is if you were looking at someone from the outside, you'd be, you know, you'd be so intimidated by the things that they've created because you don't actually see the inner working of, you know, how much effort they're putting in. I think a lot of my friends that I really admire, I've just seen them put in so much effort and force applied at this very specific angle and eventually works. But I saw the journey from the beginning to get there, and so maybe that encourages you that you don't have to be perfect to actually do the thing.
B
You have to compound.
A
You have to compound and you have to try, right?
B
Yeah, a little bit. You have to show up, you have to do. Can the same person make you feel. Really can do this, like, this freedom thing and make you feel really safe? Are those, like, different roles?
A
I think they can come in the same person that's not intuitive. Yeah. I mean it's. Well, well, one thing that I also write about is, you know, it takes two to think, which is creative partnerships. Right. And there's lots of examples that I look up to like Amos Rski and Daniel Kahneman, even Joan Didion and her husband John, you know, were a creative partnership in some ways. C.S. lewis and J.R.R. tolkien, you know, in Oxford and all those things, which is sort of like, oh, for a long time I was reading this, you know, biography of C.S. lewis and Tolkien and in it was that for a long time they were each other's only audience. Right. But they were also really challenging to each other. Like, I mean, honestly, the friendship was challenging. Like if you read the actual end to that, that they end up having, you know, a bit of a tiff and you know, a bit of conflicts there because of religious beliefs, because of writing beliefs. But I'd argue that they're probably, they probably did both. Like, they're probably like, I'm your biggest supporter, I'm your number one person that I'm going to read this and encourage you.
B
Deep trust but not low standards.
A
But not low standards. And I'm going to push you and it's going to be hard.
B
Yeah. Yeah. I think you're so right. I think you're so right. A couple other things. I'm friends, friends who help us see ourselves in Winterson's the Passion. Henri says this, this about love, but I think it's just as resonant about friendship. It is though. I wrote in a foreign language that I am suddenly able to read wordlessly. She explains me to myself like genius, she is ignorant of what she does then. Each friend represents a world in us. A world possibly not born until they arrive. And it's only by meeting this that new world is born. The Diary of Ane Ninh Mean Nin Maybe there's an open ended part of this or maybe it would be better to get specific. I know you've referenced and you've talked to me a little bit about your friend and former collaborator Justine. But I'm curious what, yeah. What does it feel like to have somebody who can do a friend who can do that for you?
A
Yeah. So for some context, Justine and I went to college together. We lived together for four years and we wrote a blog together. My first substack ever. That's not actually many people don't know about this substack. It was called Copi Club Kopi. It's a. I grew up in Singapore and Kopi is A local drink there. And it was honestly like letters to friends, letters to each other, and letters to the broader world. And I think so much of what Justine helped me see was, number one, sheer encouragement. I think she always believed in me in a way that, you know, maybe didn't make sense at the time. Like, a little bit illegible. And the other thing is that when we were writing together, it truly felt as though we were improvising together. So there's this line that Patti Smith writes about her friend Sam Shepard when she's learning how to improvise with music. And he says, hey, after one beat of the drum, stop getting so rigid about it. You can just add another beat. The music hasn't ended. We can keep going. And I think so much of what Justine and I's friendship is. So that quote is so relevant, because I think whenever I was stuck or lost or listless, Justine would say, hey, let's. Let's keep going, you know? And I think that was a very beautiful thing. We wrote 30 pieces together, and it was. You know, that's a lot. That's a lot to write with another person, let alone by yourself. Right.
B
Yeah. What an amazing. Truly. Truly. One of the great attributes is to. Is when someone makes you feel like things are possible.
A
Yeah.
B
Like, there's road ahead. It makes it easier to step. Yeah.
A
And also, I mean, one other part is, oh, I want to impress my friends. Like, I want. Like.
B
Yeah.
A
I trust their judgment. I want them to feel proud of me as well.
B
Okay. That's a good reason to have. It's a good reason to have high standards.
A
Exactly. Yeah.
B
Again, maybe this applies to Justine, or maybe not. Maybe just broadly. Huasu in Stay True, friendship rests on the presumption of reciprocity, of drifting in and out of one another's lives with occasional moments of wild intensity. This points to something that I. I certainly feel deeply, which is friendship is this strange relationship we have where, like, there's no obligations, there's no rules, at least. And so most relationships, at least, the farther and farther you get away from, like, the kind of confined school, like, parts of your life, or, like, there's this old essay I always reference that's like, your best friend could tell you on a whim, they're moving across the country, and if you protested, it would be weird. And, like, if a romantic partner did that, you'd be a sociopath, Whatever. Yeah. How do you relate to. How do you relate to, again, maybe with people in your life who you don't. Aren't in active proximity with. Which is obviously so important.
A
Yeah. Well, I think you're pointing at something which is really deep and true about friendship, which is that it's sort of under theorized as a connective tissue.
B
Yeah.
A
Like anyone can sort of be a friend in some ways.
B
Yeah. What are we. Are we friends yet? Like what?
A
You know, like. Like people can be friends and collaborators and all of these different things. But I think it's actually about. I'm gonna. I don't know, like soul resonance. Like I feel that if I understand someone's character and soul and. And what they are put on this earth to do, that bond is actually very difficult to sever. And so even when I reflect on Justine lives in London and we rarely, like, honestly we see each other maybe like in person once a year. I'm actually seeing her in two weeks. But you know, we really don't have very.
B
Not a surface area.
A
A lot of surface area. But there's a lot of density. Right. There's just a lot of density. Well, it's similar. Like you and I see each other not that regularly, but when we do, we're like on. Going on three hour walks. Right. So it's sort of depth of friendship rather than breath.
B
One of my theories is that people deeply underrate proximity in relationships. And so you can talk yourself into like, oh, we had this really meaningful walk or whatever. And then when you. Well, part of maybe what I'm getting is I've had. I've gone back into proximity with old very close friends.
A
Yeah.
B
And I thought we were as close as ever. And you realize when you get back into extreme proximity, you're like, oh, this is a little different.
A
Right. Yeah.
B
I think you. It can be maintained with. With the. A very close friend here and there.
A
But how do you think of mental proximity? So like I get physical.
B
Right.
A
But like, you know, you live next door to each other. But like how do you think of like, hey look, we're always in each other's orbit.
B
It. It has to be a non intentional. That's my answer. So if you're in an active group text with multiple other people, it doesn't really work in a one on one. I have two of my best friends who I now live in the same city as who largely Brenner and Andrew, who are big parts of me doing this podcast needed a kick in the ass. Basically. We, for the first like five years of our friendship, we didn't live in the same city, but we had a very active group text.
A
Yeah.
B
Which is different. Than like, hey, man, we should catch up.
A
Right.
B
Which is great. Like, intentionality matters. Hey, I'm thinking of you, but I suspect, again, maybe with your very best friend or a person you like. But for most of the other relationships, if you don't live in the same city, you need to have some kind of. Some kind of rhythm.
A
Maybe there's some threshold as well. Yeah, yeah. There's some threshold that you have to meet to even, I guess, consider yourself close or, you know, enough exposure therapy to. To that person's.
B
Right. It's the physical version of this is like, you want to go on, like, we're going to run some errands together, or we're going to sit in the car and not talk for an hour.
A
Yes.
B
Like, that's a. That's a level you can't really get to with only intentionality.
A
Yes. A hundred percent. Yeah. Sort of like blank space time or white. White noise. White noise time might be.
B
Yes, yes, yes. Not a question, but I just thought it was so cool and lovely. Any thoughts to share on Linda Montano and Tei Ching Shay? And they're tying each other together.
A
Yeah. Oh, my gosh. I loved that art piece where they actually tied a physical piece of rope to each other for 365 days, which is just insane.
B
And they weren't allowed to touch.
A
Yeah. And they weren't allowed to touch.
B
And they weren't lovers also.
A
No, they're just friends, I guess. I guess. I hope they can call each other friends, like, be awkward after.
B
Talk about proximity.
A
Yeah, Talk about proximity. Right. And yeah, it's very. It was a really big. I think a lot of these, like, performance art pieces say something very true about the nature of, like, connection. And so part of that piece was actually just exploring what they did there. And there was this, like, piece of paper that they signed, which is like, we will never be apart. Which I think is when they were finished.
B
Right?
A
When they finished. Yeah, yeah, yeah.
B
That would be. That would be. That would be quite crazy. But it's like, for some reason, it makes me think, have you ever seen. It's not related in any way. So I don't even know why I bring it up, but the Maria Abramovich I have.
A
Yeah, well, which one? The one where.
B
The one where she's sitting in the thing in her old collaborator. It's like this. Maybe the reason I thought of is the extreme antithesis of these two former incredibly dense. It would be like these two people, if they were in love, they didn't see each other. For years. 30 years or something. That is a moment.
A
Yes. Yeah. Well, I think Maria Abramanovic's work is, like, really about human nature. I mean, she also does this one where she's like, you can do anything to her or whatever. And you see some people do some things where you're just a little shocked. And it's really about, oh, what do you do when the human. When all these, like, false pretenses of civility go away and what happens? And maybe it's a little dark. Right. I think there's dark parts to human nature as well that she portrays quite well.
B
Related to friendship, Love, you say. Complexity means appreciating the critical difference between love and attachment, between fantasy and reality. We experience friction when we're faced with the inherent mystery or unknowability of another ties to our conversation about reality and fantasy. You reference or. Excuse me, you recommended me a short story called Closer by Greg Egan. Why is the unknowability of the other so important, so beautiful?
A
Yeah, I mean, I'm curious to hear what you thought of the short story. But basically, the short story by Greg Egan, it's a book axiomatic. It's a science fiction set of short stories. And the book Closer is about this couple where one of them wants to constantly get closer to the other person. And so what they do is this sort of transformation where you can take someone's brain and put it into another person and you can inherit all of their memories and therefore become the same person, essentially. Or union, like, become a union.
B
Closer and closer.
A
It closer and closer. And the moral of the story there is actually that it's the fundamental unknowability or the mystery of another person that interests us. So.
B
Yeah.
A
And that you can. I think it's a very romantic idea to constantly be surprised by another person and to also be seen in a different way by another person. This quote, which is not in Greg Egan, but that marriage is like one long conversation. And I think part of a conversation that keeps it going is that you don't know what the other person's going to say next. And there's some surprise and. Yeah, and there's lots of, like, relationship theorists who talk about this, you know, diamond dynamic as well, which is like, how do you keep the mystery and also the familiarity? And those are two poles of tension that you need to keep in a relationship. But I thought that short story just did a really great job of talking about, oh, hey, what happens when you don't fully know another person? And isn't that Beautiful. And, you know, isn't it hard to actually know? Everyone knows everything about someone. Yeah. You can surprise another person. You can also surprise yourself, I think is the moral there.
B
Yeah, especially you can surprise yourself by way of them, which is. Yeah, yeah, the thoughts. I. I mean, one. It's. It's. It's a. I'd recommend it. It's. It's short and people can read it. It's a really beautiful, beautiful example of the way that reality is more beautiful than fantasy. I think, in a sense, you had some other quote you had said. True resonance arises from the feeling that you are. What you are seeing is real, that it was forged through a complicated and interconnectedness and friction with the world. Ironically, the apex of absolute beauty or symmetry or pleasantness lacks real intimacy. It's flat. You take a doll and feel nothing but the uncanny, but look at a face you love in all its quirks and think it inimitably beautiful. My. Maybe it's a silly thing, but my reaction in part to your prompt about closer is there's an old idea from a friend who. He says, in a relationship, you have to decide whether you rather be bored or annoyed. And it's not quite the same, but I think there's an element of this which is like, yeah, you want both of. The implication is you want to both be deeply seen and known and have more and more intimacy, which by definition, intimacy is knowledge. Right. And yet, as someone who definitely doesn't want to be bored, like, you need to. We need to be surprised. Like.
A
Yeah.
B
And reality is surprising, even if it's abrasive. Again, maybe to the same. Same theme.
A
Yeah. And I think it's very important to have the mindset of you can change and you will change, actually. And anticipating change is also really important. There's a. I think you. You maybe saw this, like. I really love this one particular piece by John Repetti called Yet Byron never makes tea as you do, which is about his wife. And I've quoted it so many times. I hope John Repetti's not annoyed at me.
B
I have that.
A
But. But he. He talks about, you know, seeing the chip in his wife's front tooth and being so enamored in that moment with the story of the tooth. And he's like, well, if you actually looked from the outside, it might look like an imperfection. But to me, it was proof of humanity, sort of. The title, Yet Byron never makes tea as you do comes from this poem by Virginia, a line in Virginia Woolf's book or novel. And in the poem or in the novel. The point is, oh, you're telling me that you do all these things like Byron, but Byron never makes tea as you do. And you spill the pot and you, like, mop it up carelessly and you, like, put the pot in a different place. And all these little quirks are, like, a little bit annoying. Right. Like, you didn't pour the tea perfectly, but that's what makes you you. And so inimitably you that if you were gone, I would weep. And I just thought that was so beautiful. And so I keep sharing it because I think it deserves to be read. And just, like, it's a beautiful piece.
B
One of my favorite bits of that love begins not with me, but with the other. With the little eruption of the real that I experience in the other.
A
Yeah, it's so good.
B
Eruption of the real. Just a few more things. You have a line. You say, I spent a lot of time alone finding myself in the chasm between solitude and loneliness. Loneliness, I should say. What's the difference between solitude and loneliness? What is that chasm? Yeah.
A
I think the chasm comes from you can feel really alone in a crowd of people, and you can be surrounded by people and still feel alone and lonely. In terms of solitude, you can feel really held and seen by a lot of people, and you're just actually doing your own thing. It's like, oh, I have a really vibrant, beautiful community of people that love me and care about me, but I'm just going to do my own thing. And I think that's the difference. Which is like, oh, do I have people who really understand me and get me and hold me and I trust them so that I can be free and. And alone.
B
Yeah. And choose to be alone.
A
And choose to be alone.
B
And what is the chasm is that you're sort of like, dipping in between those two.
A
Yeah.
B
Where?
A
Where it's like, oh, sometimes you forget.
B
Yes.
A
I was going to say, like, I'm just a cyber, individual person in the world. And then. And then you. You realize, like, oh, no, actually, all of this. I'm up of all of these other people. I'm basking in the grace of all these other people around me.
B
It's funny, I thought you were going to go the other way, which is when you sort of, like, are willfully solid in solitude and you forget and you get lonely.
A
Yeah. Maybe you do. Well, I think that's also true. You spend enough time alone and maybe
B
you start to feel like, I chose this. I chose this.
A
I promise. I Chose this. Yeah. Yeah. It's why I can never really go on a silent retreat.
B
Great.
A
It's just like. I love solitude, but I think that's a little bit too much solitude. Yeah.
B
A line on noticing. Here's what I like in people. Perceptiveness, humility, wit, a feverishness toward good ideas. High conviction, an iterative process of self understanding, equanimity. It's easy to distill this into language, but it's hard to notice these things in real life. I think one of Grace Life's greatest skills is being good at noticing either how have you improved at that? Or the people who you really admire who do it, what drives that. It relates to the attention stuff and the beauty stuff. But noticing is a specific word.
A
Yeah. I will have another reference for that, but there's this book that I read recently called A Swim in the Pond and the Rain by George Saunders.
B
I have it on my shelf.
A
Do you have it? I think you'd really like it. But I mean, one of the main. Well, first, one of the main points that he makes in the book is that, oh, every person in this class. It's about his Syracuse MFA class about Russian short stories. He says, every person in this class has come to me already perfect, and I'm just helping them find their singularity. And the whole book is basically like a deep reading of Russian short stories and why they work and the choices that they make and why I bring this up. It seems kind of unrelated to noticing, but. But I think one learning from that book is that to notice deeply means to notice how you feel about a thing and, like, come to a worldview about a thing or about a person or about a piece of writing. And to actually understand the emotional reactions that you have with a thing and interrelationship that you create with anything that you consume or make or any person that you relate with. Noticing that dynamic, I think is really important. Some conversations and some people are, you know, make you come alive and create a new, special world where, like, there's distinct taxonomies and distinct, you know, characteristics of that world. And in living in that world, you. Yeah. Living in that world, you experience a new type of feeling or a new type of way of living. So I think noticing, to me, is noticing the interrelationships a lot.
B
Yeah, A little bit even of, like, noticing the space between, like, what's it.
A
Yeah, yeah. I think he calls it the supra personal. Not interpersonal, not super personal. The supra personal, which I think is cool.
B
There's A line in Before Sunrise and they're sitting in this alley and she says, if God or magic or whatever is real, like, it's like in the. It's in the. It's like when somebody's sharing something. It's like in the space between us trying to understand someone sharing something. Yeah, similar. A quote from Jeff Buckley, I think in a piece about. Of yours, about feeling behind or maybe the. The. The going. Things. Things going the way we think they ought to. Life has its own rhythm and you cannot impose your own structure upon it. You have to listen to what it tells you. It's not Earth that you move with a tractor. Life is not like that. Life is more like Earth that you learn about and plant seeds in. It's something you have to have a relationship with in order to experience. You can't mold it, you can't control it. But not necessarily a new theme. But. Yeah. How do you remember or how do you loosen your grip?
A
I think if you actually look at the through line of my writing throughout time online, which is like four years or five years, maybe four, I think you'll see I've gone through a lot of peaks and troughs. And I'm not afraid to say that I'm also like, oh, this is happening and I'm going to write it down. And I think the act of documenting and also just like little signposts in the journey of life.
B
Yeah.
A
I think is important to remember that you can't control things. Because even when I'm in like, euphoria of having written a piece and like, you know, and like feeling like I'm on track with all these things, I remember that, oh, there's moments of like, great, you know, great loss and great despair and great listlessness.
B
Yes.
A
And I always have to remember that these minima and maxima.
B
You're setting like anchor points, though.
A
You're setting anchor points and remembering that you can reach the maxima again, I think is. Is really motivating.
B
Oh, what a great answer. A little thing from Bob Irwin that you had sent to me that I think I'll read it. This is from that biography. We talked about him a little bit earlier. There is no such thing as a neutral gesture because for that very fact of it being there draws a certain amount of perceptual attention. Let's say it drags a weight of 0.06. Well, then it's got to give back 0.12 in energy. Some mores are major moves, major gestures. I mean, certain things are just support everything doesn't maximize all the time. There's. There's some trade off. But I did come to quickly see this thing about there being no such thing as neutrals.
A
Yeah.
B
It just had me thinking about, especially in the modern era, of, like, it's so easy to do everything.
A
Yeah.
B
And where did. Where did detail on craft come in? And just these little subtleties that. Yeah. Maybe made me think of you and it made me. It just feels like kind of a beautiful philosophy for, like, the little nudges of things. But I don't know, I was just curious if you had a reaction.
A
Yeah, I. Actually, there's a. I have a physical copy of Seeing as Seeing is forgetting the name of the thing that one sees. It's all about sort of like this ineffable feeling that you get when you see something or you understand something. It's not exactly explainable, but actually, that is the line that I underline furiously in the margins because I do think it's important to care about what you put out into the world and care that maybe it's making a statement, maybe it's sharing a perspective on the world and not having it be sort of a waste of space, if that makes sense.
B
Yeah. Yeah. And every. Every little guy just drew lines all day. Every little flick matters.
A
Yeah, a little. Well, small things aren't trivial, especially if
B
you're attuned to them or you notice them. Yes, but it's. Yeah, it's easy. It's easy if you haven't. It can be easy to not notice when you've got. When you've lulled yourself into just, like, focus. Yeah. Focusing on maximizing output. You mentioned Miyazaki. One of my favorite quotes or anything you've ever sent me. A little quote on Miyazaki and effort to endure something is obviously exhausting and agonizing. But at the same time, you must also continue to hold what you regard as important close to your heart and to nurture it. Should you ever relinquish what you truly hold dear, the only path left to you will be that of a pencil pusher. The type of animator whose sense of self worth is determined by the numerical amount of their earnings, or who cycles between joy and despair over the high or low rating his work receives. This is related, I think, to what we were speaking about just now with Bob. But maybe the thing there is about personal standards and like, independent of anybody else, maybe even like an autotelic aspect of it. I think maybe the most interesting question for you would be about writing, but how do you what kind of keeps you pushing.
A
Yeah, that quote is from. I remember the moment we were talking about it, which is in New York on a long run. And I have that saved in my phone and I return to it frequently. And the reason being it comes from his book Starting Point, which is about the first 20 years, which is so funny that 20 years is a starting point.
B
Right.
A
I think that's in itself funny and kind of telling. Right. But I think that the other point that's really important there is that you will always know you have the knowledge within yourself of the craft that you're making is that you will always know how much work that you put in, whether the outside world recognizes it or not. You can always look at the color or the particular hue and know that you chose it specifically. And I think that's like when you can actually point to things that you did for the end is not the means. The means is the end, basically, which is in the process of choosing, in the process of creating. You have the standard for yourself that you meet and it makes you proud and think a lot about sort of creating is always in that middle ground of making the work and the process of making the work rather than the final outcome.
B
Yeah. Yeah, great answer. Two final quotes. But as it is, aliveness means impermanence. We are brief bodies, moment to moment, ourselves turn over and our hands touch different surfaces. Our faces change with every smile, grimace, glance, frown. How could I expect us to say the same? I like this line I heard in the song once, any love I made you feel is yours to keep. Some experiences are sealed into the past, but they were still very beautiful. And then don't covet. Give everything. Give it all. One of my favorite books on the topic is Annie Dillard's A Writing Life, where she writes, anything you do not give freely and abundantly becomes lost to you. You open your safe and find ashes. Creatives tend to hoard notes and lines, thinking they'll be used perfectly once, once, at some point in the future. But writing is a deep well that continues to be refilled by life experience and reading and observations. Use every good sentence you have ever written. Now burn the candles. Feels very fitting, something that came up repeatedly throughout this conversation. How do you remind yourself to. To stay so abundant and so generous?
A
I think it's viewing creativity and the soul that you put into your work as renewable. Ursula Le Guin has this line, that's love is like bread remade every day made new. I think the same is true for creativity. Or there's Always going to be more inspiring things to read in the world or to ingest.
B
And we forget, though.
A
We forget like, we think, like, oh, there's a finite number of interesting people to talk to.
B
I only have so many good ideas. Yeah, yeah, yeah.
A
So many good ideas. But. But actually, look, there's. The deeper you go, the more rich it gets. And so reminding myself that, hey, no matter what I do, I will never reach the bottom of this, well, I think is something that really drives me forward and I think something that's very meaningful.
B
I think it shows. It shows in the work and the way you approach things. So an honor to do this. Thank you.
A
This was so fun. Thank you. Jackson.
B
Thank you for listening to Dialectic with Nicole. You can learn more at Dialectic FM Nix. That's N I X. Also, if you enjoyed the episode, please give it a thumbs up five stars. Subscribe wherever you're watching or listening and especially please share it with a friend if you liked it. Every little bit helps and it would be an honor to have you share it with somebody who you think would really love it. I'd also like to thank Notion one more time for presenting Dialectic in a time when the central orientation towards AI is just about automating everything and moving faster and making every individual more capable, some of which are good things. I appreciate that. Notion's orientation is about thinking together, how we can collaborate with each other with teams big and small and with the AIs, to do better work. At the end of the day, the work I want to do, the work I want to be a part of, and I hope the same is true for you, is to collaborate with amazing people and do great work. For me with Dialectic, that means focusing my time on immersing myself in the minds of the amazing people I get to speak to, like Nicole, having these rich conversations with them and then putting that together in a way that is rich and exciting for you, whether it be the episode or the transcript and lessons and everything else. And I'm using AI on the edges to help streamline that process and focus on doing more of the work I don't want to automate. I'll also link to that great piece by Colossus on working inside of Notion. And as I mentioned, if you're interested, you can learn more@notion.com dialectic or you can reach out to them or me at work@jacksondall.com thanks again for listening and I will see you next time.
Podcast Host: Jackson Dahl
Guest: Nicole Seah (“Nix”) – Writer, Investor, Founder of New Ontologies
Release Date: May 11, 2026
This episode features a wide-ranging conversation between host Jackson Dahl and writer/investor Nicole Seah (“Nix”). They explore the meaning of beauty, the tension between fantasy and reality, the role of seriousness and playfulness, creative identity, ambition, friendship, learning to love what’s real, and the importance of attention and craft. Nix reflects deeply on her creative process, personal and professional dualities, and her latest project, New Ontologies—an initiative chronicling the human and craft-driven side of technology startups. The conversation is dense with references, literary allusions, and memorable insights on living authentically, striving for meaning, and embracing both commitment and lightness.
Opening Reflection:
Nicole introduces the idea that everything we create is an “amalgamation of your experiences in the world” and “brought into the furnace of something, and come(s) out the other side.” She references writer Borges’ notion of dueling identities—one intense, one playful.
Notable Quote:
“I have multiple identities and the reason why they feel at odds is because sometimes those identities conflict or come into friction with one another.” (00:33, Nicole)
Pursuing Beauty:
Nicole draws from Iris Murdoch—beauty is a version of “unselfing,” taking us outside ourselves. She distinguishes two types of beauty: one solipsistic and inward (glamour), another outward, making us more generous.
Intentionality in Perceiving Beauty:
Noticing beauty in the ordinary (referencing poets, Simone Weil—“attention is the greatest form of prayer”). Both ‘effortful’ and ‘perceptive’ beauty require intention.
Effort and Strangeness:
The value in “tolerating strangeness,” referencing Nietzsche’s writing on learning to love the unfamiliar, and Zadie Smith on growing to love Joni Mitchell—sometimes deep beauty emerges only after patience with discomfort.
Notable Quotes:
Experiencing Art Through Others:
Nicole recalls her art history professor’s emotional reaction to Donald Judd’s boxes—inspiration from witnessing others’ passionate engagement.
Context and Guidance:
Jackson discusses how reading about or discussing art can help “show us how to see,” raising questions about originality and dependence versus communal learning.
Interiority vs. Community:
Nicole describes artistic learning as communal, not only solitary—talks, book clubs, and reflection blend together. Danger isn’t in using others’ guidance, but in “labeling something as meaningful” just because everyone else does.
Notable Quote:
“Learning is a communal thing. And I think for a long time I thought of it as a very hyper individualistic endeavor. And now I'm much more open to the fact that... it's always through community.” (15:35, Nicole)
Letting Go of Fantasy:
Nicole reviews literary character arcs—heroes return to reality after chasing fantasy, learning to love “the deeply flawed human world” because it is real.
Embracing Disappointment and Redirection:
Learning when fantasy is “a mirage” and instead finding new possibilities in reality. The “frontier” is where our desires encounter what the world offers back.
Making Contact with Reality:
Nicole suggests “externalizing ideas” and welcoming humbling feedback are key to living honestly in the world, referencing her own transition from “planning everything” to being less rigid and more open to surprise.
Notable Quotes:
Bridging Tensions:
Nicole explains her “multiple identities”—her creative side (serious intensity) and her lighter side—referencing Borges (“Borges and I”) and Hermann Hesse’s dualities.
Seriousness Births Playfulness:
Examples from Miyazaki, whose hand-drawn care and intense devotion produces films of striking lightness.
Integrating Identities:
Nicole is “working to bridge” the personas—writing, investing, painting, and more, noting that both seriousness and playfulness are in service of “loving what is real.”
Notable Quotes:
The Nature of Commitment:
Nicole admires Joan Didion’s idea that “salvation comes from extreme and doomed commitments.” Commitment, both in writing and life, oscillates between ease and struggle (“a seasickness that wouldn't abate”).
Habit and Identity:
Writing becomes easier when it’s integrated into one’s identity; Nicole sees “good faith” with oneself as keeping promises to show up and do the work.
Multiplicity of Identity:
With reference to Michael Nielsen, she advocates rejecting the “tyranny of [a] primary identity.” Writing and creativity can serve, and be served by, multiple roles (writer, investor, painter).
Notable Quotes:
New Ontologies:
Nicole’s project bridges early-stage tech, ambitious storytelling, founder craft, and personal development. It asks “how do we talk more ambitiously about the future?”—not just at world-changing scale, but at the individual and communal scale.
Profiles as Mirrors:
In her profiles like Ando’s founder, Nicole emphasizes “techne”—the personal craft and taste founders bring, the “cosmology of self” (Rebecca Solnit).
Convergence vs. Duality:
Reflects that ikigai—the convergence of passion and work—emerges after much “route finding,” not by force. It’s a gradual process mirroring Monet’s many water lilies or an artist’s lifelong repetition.
Notable Quotes:
The Value of Beauty and Craft in Technology:
Nicole argues that even the design of software—like Ando, an “AI-native Slack”—shapes the psychological and creative experience of users. Beauty and craft enhance both product and human experience.
Utility and Beauty:
Even in utilitarian products (e.g., Amazon), “sweating the details on the part that really matters” creates meaning.
Notable Quote:
Desire, Agency, and Appetites:
Discusses Caroline Knapp’s writing on feminine appetite and ambition: allowing oneself to want more, to express desire without shame, and how agency compounds ("confidence is the memory of success").
Friendship as Freedom:
Honest, inspiring friendships can make us “differently free”—friends who make us feel both safe and challenged, and help us see new worlds in ourselves.
Creative Partnerships:
References to literary and artistic duos—Didion/Dunne, Lewis/Tolkien, Kahneman/Tversky—who provide both support and challenge.
Notable Quotes:
On Proximity:
Deep friendship may rely less on frequency of contact and more on “density”—the shared depth and resonance between individuals.
Performance Art as Metaphor:
Cites Linda Montano & Tehching Hsieh tying themselves together for a year—highlights the power and strangeness of human connection.
Unknowability as Beautiful:
Discusses Greg Egan’s "Closer"—intimacy is richest for being incomplete and mysterious. Also references John Repp’s essay on loving real, imperfect partners (“Yet Byron never makes tea as you do” by Virginia Woolf).
Intimacy and Surprise:
"You can surprise another person. You can also surprise yourself…" (98:16, Nicole)
Imperfect Reality Over Flat Perfection:
True resonance comes from what’s real and flawed, not flat symmetry (“You take a doll and feel nothing but the uncanny… but a face you love… is inimitably beautiful”).
Solitude vs. Loneliness:
“You can feel really alone in a crowd of people…Solitude [is] about: do I have people who really understand me and get me and hold me and I trust them so that I can be free and alone.” (101:35, Nicole)
The Gift of Noticing:
Referencing George Saunders’ “A Swim in a Pond in the Rain,” Nicole identifies “noticing the interrelationships” as a profound creative and relational skill, part of becoming more attuned to beauty, craft, and feeling.
Letting Life Unfold:
Life is not something to mold and control at will, but “more like Earth that you learn about and plant seeds in.” (Jeff Buckley, quoted by Jackson)
Generosity and Creative Abundance:
Discussing Annie Dillard, Nicole urges: “Give everything. Give it all.” Creativity and love are renewable. “No matter what I do, I will never reach the bottom of this well, and that really drives me forward.”
Notable Quotes:
The episode is an intricate meditation on beauty, reality, identity, ambition, and human connection. Nicole Seah offers not only personal philosophy but also practical wisdom for creators, strivers, and anyone wrestling with multiple passions or the desire to bring more beauty and honesty into their life and work. Her signature is a blend of humility and conviction: a refusal to prescribe, a willingness to “walk next to” listeners as peers in the journey, and a reminder that everything meaningful is “forged through a complicated interconnectedness and friction with the world”—always renewed, always real.