43: Mario Gabriele - Reality is Story-Shaped

[00:00] The way to escape competition is through authenticity. Almost like staring at the sun. Yeah. It's like you can't really like look right at it. I'm curious how you have approached trying to get closer to it. I guess the things that have brought me closer to authenticity are doing things myself and putting myself in positions where there are few to no excuses that you can rely on. That's so good. Founding The Generalist was like, in many senses, the most authentic thing I've done professionally. [00:30] well-adjusted, and seems like full of ambition. Like, there's always something. People might tell you that's the case. There are founders you talk to who say, oh, I had a wonderful childhood. And then you'll find out 10 things where you're like, [00:41] You had a wonderful childhood. Why are stories so useful? Stories are just like the hyper effective version of language in my view, because I think that's how our minds are so wired. Like if I tell you something in a parable or a story, there's a reason that's like the foundation of all of our religions and political systems. In one part of your professional and creative life, you are the one kind of observing and creating these stories. And another part in your investing life, you're almost the one divining them or listening to them and interrogating them. Do you almost have like a skeleton key because you are a storyteller yourself? [01:10] Wow, that's a really interesting observation. I hadn't put that together. [01:14] Welcome to Dialectic episode 43 with Mario Gabriele. [01:18] Mario is a writer and investor. His primary focus for the last several years has been The Generalist, where he writes a subscription publication focused on technology, entrepreneurs, investors, the broader shape of the industry, and does so through a remarkably narrative lens. He's ultimately obsessed with stories, and so he brings the rigor and analysis you might expect of someone oriented towards investing, but also does so in a form that is much more narrative and makes it

[01:48] Mario has described it as having the rigor of Wall Street analysis in the style of a New Yorker profile. Stories run through everything Mario does, but he also brings a remarkable level of ambition as well as authenticity to the work. [02:18] the ways he can continue to raise the bar and widen his personal aperture. Obviously, I think part of this is what makes him good at being so attuned to the entrepreneurs he invests in. And he and Hummingbird both are quite focused on evaluating founders above anything else. [02:33] Mario also has an amazing podcast as part of The Generalist where he interviews founders and investors, so it was fun to flip the tables on him and do so here in London. I hope you are inspired to play to your comparative advantage and also to continue to raise your gaze for what might be possible. [02:49] Before we get into the episode, I'd like to thank Dialectic's presenting partner, Notion. [02:54] Notion is a collaborative workspace for your life's work, for just you or your entire team. And they are on the cutting edge of the ways that AI and agents can be brought into the work and give you more leverage. So rather than automating the real deep thinking work, they're focused on whether it be Notion AI itself or most recently custom agents being able to give you all kinds of additional leverage. I use Notion AI in how I prepare for the episodes

[03:24] and patterns across individual episodes and across the broader body of work. I think in many ways, dialectic is part of my ongoing project to create a curriculum of learning for myself and hopefully for you. Being able to rely on Notion AI both to get more insights, but also to actually help with the packaging and the process of putting out these episodes allows me to focus on the most important thing, which is getting to immerse myself in somebody's mind in their writing for the conversation and then getting to have a conversation with them that feels deeply alive. [03:53] With that, here is my conversation with Mario Gabrielli. [03:58] Here we are. Mario Gabriele, thank you for being with me. [04:01] Being here with me, I should say, being with me. [04:04] I'm sorry I didn't nail the Italian pronunciation. Alas, I did my best. No, I think a very good one. It's great to be here. I feel like the turntables have turned. [04:15] You're right in your normal spot, so it's fun to be here in London with you. I'm going to have to pull myself back from getting into interviewer mode and let you take us where we should go. Well, I want to start with stories, probably unsurprisingly. You have a great... [04:33] And I'm not quite sure how recent it was. Maybe a year ago, you wrote this list of observations about how you think and things that feel true to you. And there's a bunch of them that resonated. But one of them was you become the stories you tell about yourself. [04:47] And so I'd like to start by asking you maybe to reflect on [04:51] the essential or kind of like dominant stories that have been,

[04:56] felt true for you over time. Um, [04:59] and to the extent those have persisted or compounded or totally changed, evolved. Obviously, you don't have to run through everything, but I'm curious if there are kind of dominant themes that come to mind as you look back. Well, we might not get to a second question, I think. Oh, man. I don't know. I feel like this is infinitely deep as a sort of place to explore. I'm trying to think of how I would do this. It's interesting that I make that observation, and yet I don't have – [05:25] like obvious things that I would say, oh, definitely. Maybe that's the kind of story in itself that I'm a little, I think that is based on myself. Probably the stories I would tell about myself are, you know, a lot of my early life would have been, [05:41] Hyper... [05:43] focused, achievement oriented and like outwardly very linear. I was like a very serious student, very perfectionist in that sense. But where with sort of. [05:55] some amount of... [05:57] of an inner life that maybe didn't get reflected in that sense where it was much more about stories and these different explorations and, [06:05] I don't know, I think adulthood is in some sense rediscovering [06:09] the most childlike version of yourself. Um, and so I feel like I'm closer to that than I was 10 years ago. Certainly. And the point you were making when you said like, uh, when you're younger, it was more consumption. It was like more inputs than outputs perhaps, or, um, or more like living in other stories than your own story. Yeah. I mean, I think, you know, very young, the most natural and sort of innate part of myself, I think from, you know, the mythologies you hear

[06:39] So I think that's like very authentic to who I was from almost birth. [06:44] then I think you try on different identities as you become an adolescent. And there was a period where I was going to be, you know, a very serious trial lawyer and a politician. And that was a very sort of [06:56] striving, thrusting, you know, phase of, of, uh, [07:00] you know, early... [07:02] adulthood perhaps. And then I think you sort of integrate lessons from all of it, but hopefully come back to yourself. I think that's right. You've talked about [07:12] I think this is a quote, but if not, I'm slightly paraphrasing. The most efficient and enjoyable way to learn is stories. [07:20] I do believe that, yeah. [07:22] which isn't, [07:23] I think some people might totally resonate with, other people might be like, stories aren't true, or something. Why... [07:32] Why are stories so maybe maybe a silly way of putting it, but why are stories so useful? Well, in some level, I think you could make the complaint stories aren't true in the same way you could say language isn't true. Right. Like it's a distillation. [07:46] of some like platonically perfect piece of information. And so this is the best we have. And stories are just like the hyper- [07:57] effective version of language in my view because i think that's how our minds are so wired like if i tell you something in a parable or a story there's a reason that's like the foundation of all of our religions and political systems uh you need founding myths uh and those just happen to be like a thousand times

[08:16] Maybe I'm even underselling it by many orders of magnitude. So much more durable and magnetic than anything else we can come up with. So I think it's just a construct of the way our brains work. It's not an objective reality. It's just a species subjective reality. [08:34] That's a fun... Yeah. Yeah, it's almost like... [08:38] we have to resort to this. Yeah, exactly. This is what our minds want. And so this is the story we have to tell ourselves. Yeah, that's true. Again, a very open-ended question, but I'm curious if, [08:50] If you find yourself... [08:52] noticing any patterns in the types of stories you tend to gravitate to. Yeah, I did actually a funny exercise there. [09:00] where I had Claude look across everything I've written and all of my... [09:06] sort of read wise highlights, the pieces I've shared, uh, saved, um, [09:12] and sort of try and think, what are you interested in? What do you actually seem to gravitate towards? And it was actually, I thought, reasonably... [09:19] It resonated with me, which is that... [09:22] There's some... [09:23] Axis between like madness and greatness that I'm really drawn to. [09:30] And. [09:31] Yeah, what it takes to be great, the level of sacrifice and the uncomfortable parts of [09:36] of these great personalities and sort of that nuance. Because I guess I... [09:42] At some level, I'm just like really... [09:45] interested in the psychological piece there because usually that gets collapsed one way or another it gets collapsed into a hero or it gets collapsed into a villain um and the interplay there is like

[09:58] Really deeply intriguing to me. So something about, yeah, ambition and what that takes. [10:04] Do you... [10:06] I'm curious, do you relate? [10:09] Everyone relates to themselves as the hero of their own story. With that comment in mind, like... [10:15] Do you ever find yourself kind of like monitoring your... [10:20] tendency to place yourself as the hero. [10:22] Essentially, I think that's like a really deep, interesting question and seems like the answer would be yes to me. Like, I think I. [10:31] for better or worse, find it very easy to slip into other people's perspective on things. Oh, cool. [10:39] And the good part about that is I can really, you know, almost – [10:44] intuitively i think sort of understand an argument from another perspective and almost begin to believe it in some sense like i'm like yeah i can i can see the the jumps that you're making to get here and it's not the jump i would make but uh [10:57] There's a logic to it. The downside is that sometimes you can... [11:02] Think about those things so much that sometimes... [11:05] it maybe takes me an extra beat to listen to myself and like hold firm. And the idea that like, no, no, this is also a valid way of, of parsing this. I was going to say, I think it involves on some level, pulling yourself back or making yourself a little bit smaller for some period of time. Yeah. Um, in a way that you have to like reinflate or something. Yes. But I think frankly, like the, the, the work that you do as a podcaster that I'm trying to do, like in some sense you have to be putting yourself a little bit into the other

[11:35] That's part of the fun, but also, yeah, maybe part of the challenge once the episode ends. Yeah, I wonder if perhaps that is... [11:43] a common theme amongst storytellers or especially writers. Like it's telling that obviously there's some counterexamples, but like often writers or writers throughout history aren't the like grand figures or the heroic figures that you think about somebody like, I don't know, I was thinking a lot about Proust this week because of a couple of people I interviewed or other folks like that who are kind of these like, certainly not to compare you to him, but like the, there is an element of the, [12:10] There is the hero and then there is the storyteller. Yeah, definitely. Talking about the hero. Yeah. And I think I'm more comfortable as the storyteller in that sense. Yeah. There are a lot of fearful writers in that sense. Kafka is a terrified person. Right. Right. You don't get that many Hemingways. [12:27] That's exactly who I was thinking of. [12:30] What, maybe on that note, like what else do you think, again, possibly way too open-ended, but what else do you think makes for really great storytellers? Or at least the storytellers that you tend to admire? A level of... [12:43] Obsessive observation. I think great writing is often just some version of like very precise writing and not in the sense that you're going into everything in very granular detail, but you're like observing a feeling or observing. [12:59] a... [13:01] experience or an occurrence of [13:04] with such fidelity that you're able to make a comparison that someone else can't you know that's sort of the basis of a good simile or a good metaphor is just having that element of surprise it's almost like a joke in that way you know you need there to be some surprise for it to feel fresh yeah um

[13:20] And then for me personally, I like hugely care about just the quality of. [13:26] words. And that's hard to be too prescriptive about, I think, because I more or less disagree with a lot of [13:35] writing advice. And so I don't know if you can really... [13:42] Put. [13:43] uh a set of dictums on what is likely to be good writing because the way good writing forms is like insanely diverse and what one person can pull off another person can't and so on and so forth yeah you wrote somewhere i think in that list of maxims almost all writing advice is actually like copywriting advice yes yeah that's like why do you think writing advice tends to not be good or what are the what types of things are typically missing well i think most people who give writing [14:13] And so you get a bunch of good ones are keeping the secrets. Like what? No, it's not worth their time. It's like, they understand that mastery is like not easily. It's kind of tacit distilled. Yeah. Into these like set of rules. Um, yeah, [14:25] Also, frankly, like the people who... [14:28] gain attention in the modern attention economy are not like literary novelists um they don't want to play that game in most cases and also are probably not very good at it like you know there's a level of uh [14:42] that I think is almost like directly opposed to most good literary writing. So, yeah, it tends to just be the case then that, [14:50] the dominant writing advice for people in our rough milieu is like,

[14:55] here's how you write a really good blog post or something like that. And that is just copywriting advice, more or less. Or it's sort of like a version of LinkedIn writing advice where it's like, you start with this. You start to write a really good list. Yes, yes. Here's a really stupid hook. And then, you know, here are 10 things that you should say and, you know, et cetera, et cetera. So I don't like that because I think it destroys the... [15:21] information landscape that we all have to occupy uh it's like a pollutant uh so i try and avoid it i don't know if i'm always successful but um [15:30] I don't recommend people think about it too much unless they're purely pragmatically minded towards, you know, I don't know, if you're running a business and you need LinkedIn views, then whatever, do what you got to do. You know, there are worse crimes to commit, but it wouldn't be my preference, certainly. [15:50] I heard you sort of saying... [15:52] a lot of good storytelling is sort of like seeing what's there. And it's not the specific phrasing you use, but there's something to that. I was thinking about and reading about Herzog or Herzog, this, um, [16:04] this week and there's all these kind of examples of him doing what I think he calls ecstatic truth um and this idea that like he's not that interested in facts there's a story of him like uh some kind of guy who had been in like had some kind of trauma around the military or something and it's like he has this part where he closes and opens the door like several times and like

[16:26] as this almost like OCD tick to signal like, um, [16:31] He wants to be sure they can get in and out. And like Herzog added it in. Like the guy doesn't actually do that. Oh, wow. Really? [16:39] And I, [16:40] Obviously, that's a very specific example, but I do think there are, there's a writer I really like named Benjamin Lavitude who wrote When We Sees to Understand the World. He talks about something similar where it's like fiction is this sort of shape we give to reality. I heard you saying something like that, and I'm curious how you think about it. [16:58] you do work that in many ways is really interested in what's there and what's true and maybe even the facts or the robust analysis. And yet, like storytelling, to tell a great story, first of all, let alone to tell maybe even the quote unquote truest story doesn't always like, [17:28] is true. Well, I love that Herzog. [17:32] anecdote. I suppose... [17:35] I fundamentally do agree with the point that, [17:38] There are deeper truths in fiction than in nonfiction a lot of the time, and that sometimes... [17:45] To explain something with really high fidelity, you almost have to resort to imagination or fiction. I think for something like The Generalist, [17:55] The only way I feel comfortable doing that is if I'm sort of explicit that this part is, you know, imagination. And so there are there are pieces I've written where there is sort of like a flight of fancy like that. Like, I think I'm recalling.

[18:08] Uh... [18:10] a piece on rocket internet where, you know, they're at the gates of, uh, St. Peter's gates or something like that. You know, like there, there's, there's those sorts of things where I'm okay with, [18:18] trying to [18:20] make some kind of larger claim, but I wouldn't ever want someone to confuse those things with [18:29] oh, this actually happened. Because then I think you lose trust in the whole enterprise somehow. Right. [18:36] Right. [18:37] Yeah, and also... [18:38] There's a there's a sort of central conceit or premise in the container you've created that is promising some love, some baseline. Right. Yeah. At some level, at some point in my life, I hope I'll write a novel about VC in tech. And, you know, then I can talk about truths that are. [18:59] through that lens. But still, you have a lot of latitude when you write these pieces. You can bring in influences, or you can tell other stories. This is what's interesting about Herzog. He's a documentarian in some sense. So there's a fuzziness, but I also hear you on the stakes of getting it right, quote unquote. But I guess he tells you that it's not real, right? I don't think he does. He doesn't. Not in the documentary. Not in that example. But I think he's doing a lot of this. Which is why, again, he's doing something. He's doing a project. Even [19:29] I don't know, he's studying humanity or something. He's doing a project that has a different tenor than yours does, but I do think every writer's doing a little bit of this in some way or another. Definitely. I'm reminded, maybe I won't be able to remember the name of the movie, but it's a documentary by a documentarian who studied the Indonesian genocide. Do you know what I'm talking about? No, I don't. I think the second one is called maybe The Look of Silence, but the first one is...

[19:56] he the documentarian goes and meets a bunch of the people who perpetrated the genocide um who are now sort of heroes in indonesia because they won in some sense uh and he goes in almost portraying what he's about to do as you know a heroic version of retelling their story uh but in doing so he [20:20] Wow. And it's fantastical and not true in some incidences, but in some cases it's deeply true and is the first time they're really confronting people. [20:28] what they've done. So I really admire people who, [20:31] managed to [20:33] play with that boundary and [20:35] yeah, say something like insanely deep because of it. Um, so I, I, yeah, I certainly haven't approached anything of that level yet, but, um, [20:43] I think what you're pointing at is very, yeah, very profound. Hmm. [20:47] I'll find it and link it to it. One other note on this. In your Hummingbird piece on... [20:56] Barant? Yeah, Barant. Barant. Yeah. He's talking about, you're talking about him and you're talking about kind of this like story underneath the story. You say it is the job of the venture capitalist to listen to such stories and to poke at them, to find the holes yet to be darned and stick a finger through the fabric, to find the story beneath the one being told, hiding, to hear what is being said and what is not. And we'll talk more about this later, but it is interesting that [21:22] in one part of your professional and creative life, you are the one kind of observing and creating these stories. And then in another part in your investing life, you're almost the one divining them or listening to them and interrogating them. And I'm curious,

[21:36] about the way that that [21:38] influences like are those two totally different modes are do you almost have like a skeleton key as the listener because because you are a storyteller yourself wow that's a really interesting observation i hadn't put that together um [21:50] I think the unifying principle is just that I'm a collector of stories. Like I just want to hear as many as I can. And my wife sort of makes fun of me for this because if I have, [22:02] five spare minutes i'm trying to like consume some kind of story whether that's you know like reading something on a book you know you know i have a little uh ebook in that sense um or listening to a podcast or watching it like a youtube like my mind is [22:17] like hyper-oriented to almost eating as many stories as I possibly can very greedily as often as I can. And founders just happen to, I think, have some of the most interesting possible stories. So I don't know if it gives me... [22:34] Well, I don't know. [22:35] I don't know. Maybe I can say it gives me some sort of rough advantage in understanding these stories. You can see the moves people are making and if it's a little too neat. [22:44] there's something that's always a bit disconcerting with that. Like if someone's too clean a narrator of their own story, then it's been polished through use. Right. Uh, and then, uh, [22:55] That to me... [22:56] makes you think a ton about what's being said. [22:59] delighted um [23:01] - Yeah, it also, maybe there's a good meta reminder that all stories have layers, implicitly or explicitly, including the ones, and it's maybe like, you're reading a great, one of your amazing, you're writing about Founders Fund or whatever, and you're seeing the work you're doing about the kind of surface level stuff and the things working underneath, but

[23:22] every story we hear and every story we tell has this, this kind of inner workings, a good reminder. Yeah. There's a, you know, the sort of, [23:30] the photographic negative of every story in some sense. Like you have the story being told and then you have the story not being told. I want to talk about [23:41] kind of the different modes of [23:43] the way you work. But before we do that, maybe a few minutes on kind of like navigating the path to the kind of current set of things. Um, [23:54] Another maxim from you, it should concern you if you have never failed at something. You should fail badly relatively often. Otherwise, you are playing it too safe. [24:03] uh, [24:04] cliche but probably cliche for a reason i think on some level um and i like the way you frame it specifically um which is not necessarily like fail often yeah but um [24:13] Are there any times that... [24:15] you failed badly, that you... [24:17] would be willing to share yeah for sure i mean i i have a bunch but at least very memorable or formative ones [24:24] Yeah, I mean, one of the biggest failures for me... [24:27] which was... [24:29] instructive was [24:31] It's not like a super legible failure in some ways, but I studied abroad in Nepal during my junior year. [24:41] uh of undergrad and that was like a very formative experience for me because i was hyper isolated like there were a few other people in the program but nepal during that period had [24:51] I don't know if it's still the case today, but lots of load shedding. So you had very limited...

[24:56] periods of electricity, which meant you had even more limited periods of internet. And when you did, that was, you know, sort of not the best connection anyway. So it was just very hard to [25:08] sort of leave everyone I knew, uh, [25:12] be in an environment where [25:14] Maybe the people around me spoke English, but go one degree out. No English. Very different environment. [25:21] And I call it a failure just because I struggled so much. Like, I think I went into it thinking, well, [25:27] You know, almost within that same to take us back to the beginning of the conversation, the sort of costume of the person who can do anything and, you know, can be put in any environment. Be comfortable in any environment. Yes. You know, you have almost like a conqueror's mindset. You're like, ah, and this is a new place. And there I shall, you know, I shall make make this just as magical as anywhere else for me. [25:53] And. [25:53] I, you know, [25:55] I found it productive because it forced me to sort of tear down all of those stories about myself. But I was like deeply tormented mentally. And I feel... [26:06] Still a bunch of sadness about it because I feel I failed to experience so much of what that place had to offer and a bunch of the things I wanted to do going into it. Like I had, you know, visions of... [26:18] Devoting myself to more serious Buddhist study and meditation and meditation. [26:23] you know, doing Everest Base Camp and these sort of things that are a bit of bucket list, these sort of things. And, you know, it sounds silly. And maybe the lessons I took were.

[26:32] in some sense more important, [26:34] certainly more important. But it was a big failure. And as I [26:39] As I reflect on it, that one still feels a bit sore. [26:42] Hmm. [26:44] Perhaps it will come back around as these things, in some strange way. I don't know. These things tend to... [26:50] land in the way maybe it's just us narrativizing reverse but they intend to land in the way that we need not the way we intend especially things like that I'm grateful for it in some sense and still bugs you in some sense too [27:09] One of the cool things about the amazing, basically, book you published on Founders Fund is this kind of overwhelming theme of returning to originality. Obviously, Teal's kind of core idea is resisting the memetic... [27:25] flow of the world, you... [27:28] On one hand, I think I've just already done a lot of different things over the course of your life, whether it be the law stuff and the IR stuff or the... [27:35] fiction and startups and working at the restaurant like so many different things so many things probably i don't even know about um mike's a lot in that piece he says the way to escape competition is through authenticity and you talk a lot about this kind of finding your own specific game i think authenticity is both something like i'm really drawn to and care a lot about and it's also like kind of blurry or it's like almost like staring at the sun yeah it's like you can't really like [27:59] look right at it. I'm curious how...

[28:03] you have approached trying to get closer to it. [28:06] Maybe not as like a threshold to cross, but like a continuous gradient. [28:12] Hmm. [28:13] I guess the things that have brought me closest... [28:16] or closer to authenticity are doing things myself. [28:22] and putting myself in positions where [28:25] They're... [28:26] are few to no excuses that you can rely on. Um, that's so good. Yes. Uh, I think you either like rise to that or you, you don't. Um, yeah. [28:39] And so actually, you know, Nepal was a good example because that, you know, stripped away actually a lot of the artists. Like a distillation, right? Yeah, yeah, exactly. So maybe that's a good example. But the generalist founding the generalist was like, in many senses, the most important. [28:53] authentic thing I had done professionally precisely because it had that structure of like... [29:00] having to do something [29:01] purely yourself being purely reliant on yourself and what i think i've come to believe about myself as a story maybe i tell about myself is that like [29:10] I work best in those environments. And so that's a nice story to believe in some sense, because it makes you predisposed to take on more of those risks. But I think there is truth to it. At least my experience, and I think other people relate, is these things that [29:25] very obviously authentic in reverse. Or looking back, maybe for you starting the generalist, or whatever it might be, there was actually a lot of friction in crossing into that. - Yes. - Have you found that to be the case? Has it gotten easier when you're adding things now that feel more authentic, or is it always like almost this jujitsu or something?

[29:43] I think birth is always painful. I think this is a universal constant and starting a newsletter is much less painful than real birth, I imagine. But for as much as I can... [29:54] Uh, [29:55] Yeah, sort of think of it from my own perspective. It was like the amount I thought it was a risk, the amount I vexed over it and asked for advice and all these things when, you know, action produces so much information. You could just try and it would be fine. And if it didn't work, that would also be OK. [30:14] I think it was helped by the fact that I had tried on so many of these different costumes of various points that I almost didn't tie my identity too much to it. It was like looser. Yeah, it was like, OK, well. [30:25] Thank you. [30:26] This feels really true, but if it's not... [30:29] I'll survive. That's fine. Yeah, I'll keep figuring it out. [30:33] Hmm. [30:34] There's another kind of related thread around [30:37] maybe like not being well-rounded. Two quotes I liked. First, how you do anything is how you do everything is a perfect encapsulation of what is not true. Brilliance is context-dependent. Energy is context-dependent. Insight is context-dependent. See Steve Jobs' pathetic job application. And then in your conversation with Paki, you were talking about Founders Fund, but you said, when I asked almost everyone at the fund [31:02] What their big lesson from Peter was, it was that you just have to focus on your comparative advantage at the expense of everything else. And that's another way of saying that in a sense. And so if I was to take one lesson from the piece as a fund manager, it would be to find that comparative advantage and then design a game so that you can just do that.

[31:21] uh, maybe with the previous question in mind and acknowledgement that it's like maybe a directional gradient and not a threshold, like, [31:29] How... [31:30] what is your comparative advantage? And then like, how have, how have you like dialed in the resolution of that over time? I have to first say how much I truly hate the expression that how you do anything is how you do everything. It really like even hearing you say it, I find it so, so stupid. Like it's so incorrect, obviously, but it sounds like something that has the rough shape of wisdom. And so people have like attached themselves to this idea. Yes. And like, I'm not [32:00] prosecuting it sounds sort of like it has the rhythm of wisdom like it's phonically wise but it is semantically so unwise and so untrue and like i think there are i guess why i hate it so much is because there are a thousand things like that that we [32:17] Maybe I'm just really cued into that one. There's something where that's bouncing off of you. Yeah, but there's probably a bunch of others that I'm taking in as like, wow, someone paused in just this right way. And now I think that's true when it's like there's nothing that has no calories in it. And there was a period in my life where I would hear someone say that, especially as an authority figure, perhaps like, you know, when I was just getting into the tech world, there were probably. [32:41] founders or venture capitalists who would say something like this and i would think gosh well [32:46] I'm not like that. You know, I know that I have differences in how I do. Different intensities. So I must not be up to it. I don't have the juice. I don't have the juice because, look, I'm so much better at writing than I am at something else. Or I'm so much, you know, I don't care about this or that. And so...

[33:04] These are all such nonsensical things that we use to... [33:08] to sort of interrogate ourselves, but the person who gave you that horrible piece of wisdom, who put that little software bug in your head, didn't even think about it for one second if they said it, in my opinion. I want to push slightly, which is my sense is, I tend to agree with you, although my sense is, at least if I think back to when I'm hearing that, the good part of it, in theory, is, [33:32] It's like to the person who doesn't quite have the job they want yet. It's about personal standards. [33:38] and integrity and like and so basically like show up at the level you want to be showing up even if it were like your dream job but again i'm i'm doing a lot of work you're doing a lot of work that's not in there um look i look forward to someone coming out with a good defense yeah yeah yeah we welcome yeah that i can hear and think if i think there's anything to it i don't believe it but um whatever this is why why you know people have different interesting opinions on things [34:08] for that. I don't know what your question was because my rage clouded me. Comparative advantage. [34:16] Again, I'm sure part of it is the story thing, but acknowledging that [34:20] it's, [34:21] Your answer in five years is going to be different. Like the direction of travel on that, like the comparative advantage and particularly like how you've started to dial it in, like see it a little bit. [34:29] higher resolution. I'm a pretty good writer, and I think that's actually...

[34:34] Rare. [34:35] I think there are not that many people who take writing seriously in the world as a as an activity. And then there are fewer people who really put in a ton of hours to get good at it. And I definitely did that throughout my life. And so I think I have the ability to distill information differently. [34:58] into a story that is [35:00] at its best moments, elegant and true. [35:03] And then I think particularly with the generalist, [35:07] I have the benefit of [35:09] having a decent grasp of technology and venture, um, [35:13] Both of these things are infinitely deep, so I don't want to pretend like I'm, you know, uh... [35:19] It's a comparative advantage. It's a comparative advantage. Yeah, but, you know, put those two things together, I'm good enough at both that that's, you know, that's enough. And then I think the more... [35:31] fundamental pieces, I think I have a pretty good [35:35] Ability to connect to disparate threads and like see patterns across different things where. [35:42] that [35:43] helps you reveal something that's maybe true or to make a connection more deeply, um, and, [35:50] So something in that in that zone. [35:52] I agree. Oh, thanks. To talk about writing a bit. [35:56] Uh, [35:58] You... [35:59] write about things that are relevant. Um, but it's very good, not just in narrative, very grounded in, um,

[36:07] Historical context. [36:09] At the very least, like the bigger picture. And I think you've talked about, like, you're not very interested in, like, news. Yeah, yeah. [36:17] Like why, and maybe I would add like the technology world, the world you operate in, the BC world, whatever, is like very, not only hyper present, but like the current thing kind of complex, but even like very self-referential and like insular. And so I'm curious how, maybe it's just the background in writing and fiction and in literature, but like why that's so important to the work you do. [36:38] I guess a lot of the... [36:40] more insular references. I don't know. I'm struggling to think of a good example. But for the most part, I find they don't super land for me. If someone is writing and doing more of that in-jokey stuff... [36:52] It doesn't fit the way my brain really parses this information. [36:58] That's another good point is that I think it does the way you do it. [37:01] also makes your writing, it both has the depth and it actually probably makes it more accessible. Yeah, I think that's probably true, hopefully. And then the other piece of it is, [37:10] that [37:11] Sometimes I think when you... [37:13] tell a story in such a, you know, I'm using provincial, not pejoratively here, but sort of, you know, literally in a more provincial sense, you kind of miss... [37:25] the [37:26] the big shape of it, the big architectural thing that's happening here. And sometimes the best way to show people like, hey, this actually isn't so different or this is extremely profound because, you know, XYZ is to say, we've seen some version of this. We actually understand what this might mean or what this might do.

[37:46] And so, yeah, and then there's probably some degree of like, [37:51] ego and bombast where I'm like, just, I like thinking in these grander settings. And that's also can be a weakness where, you know, you imagine every new feature is like, you know, some part of the Roman empire or the Mongol horde. And it's like, you know, well, let's, let's dial it back. Is what you do journalism? No, I don't think so. I think I've never perceived [38:21] Um, um, [38:22] What is the difference between those? I don't know. I think you could, a journalist would probably say... [38:28] Yes, this is journalism. And maybe the... [38:33] The argument would be like, oh, by not taking on that mantle, you're giving yourself too much of an out or you're giving yourself too much latitude. [38:42] I think I try and adhere to journalistic standards, but it's true that I've never worked in a newsroom, so I don't – [38:48] I'm intuiting that along the way. I always want to be honest and conduct interviews. [38:53] deep research and fact checking and all those sorts of things. But, uh, [38:57] I am sure someone who's worked at the Guardian or the New York Times or one of these places would have a different way of processing information. But an analyst to me is still fundamentally doing some of that fact based work, but is happier taking a bit more of an opinion, a bit more of a stance and.

[39:18] It's also, you know, in the connotations of the financial venture equity analysis world, like more about the investment lens. Right. And I think. [39:29] That is. But it's typically far less narrative or far less story. Like, which that's what's interesting to me about the. But I guess I don't find most journalism that narrative. Interesting. Like I find a lot of I don't know what you call like the atavist journalism. Sort of. Yeah. But it's it's really much more like long form magazine writing. [39:59] Yeah, like the New Yorker writers, I kind of don't, maybe I'm totally wrong, but I think a lot of them don't. [40:04] wouldn't say like, I am a journalist. They'd be like, I write for the New Yorker. I'm partially asking people. I've met a few people over the last year that I've been doing the podcast and people ask me or have asserted that I am a journalist or ask me if I'm a journalist. And one of the things that I feel that I think really see you. One of the things that [40:20] is rooted in the question that is both true for analysts and journalists, is there's a tremendous amount of rigor, which is rare in this world, in the world that you do. But it's next to this thing that I relate to, which is you overwhelmingly... [40:33] are writing positively. And that doesn't mean it's a puff piece. I think people, if they wanted to be super cynical, could call it marketing. Some of that's about incentives, but it's this interesting combination of tremendous rigor, the rigor, quote unquote, of a newsroom, but framed in this, like, I want to tell you about why this might be great. Yes, it's true. There is a filter that I'm running most of the time, which is

[41:00] do I want to write about this thing that I really think is interesting? And in some level, like, [41:06] uh, or important. Uh, so there's a positive valence on like the topics I pick. Um, and, [41:14] I think there are plenty of things where I end up in the process of talking about a very thing that I, you know, something in a positive valence actually like poke a lot of holes or talk a lot about risks that. [41:27] in many cases other people have missed. Right. [41:30] Because I don't want it to be... [41:33] a puff piece or marketing, but it is, it's undoubted that there is like that, [41:38] That feeling and almost that's axiomatic because part of the generalist was a response to the sense that all tech coverage was like hyper negative and actually missed information. [41:50] much of the exciting stuff happening. I think that's right. [41:54] - There's this interesting thing where you always refer to the generalist, you talk about the generalist, not Mario. You use the pronoun we more than I. [42:05] Maybe that's just a habit or whatever, but I'm curious if there was any conscious decision inside of that, and maybe if it relates to any of this other stuff around what the thing is. There are a lot of returns to... [42:16] it being the [42:18] Mario podcast or the whatever. Like the brands are dead, personalities rule, and yet there's something subtle maybe in the way you've done it. [42:26] Interesting. Well, it's an interesting linguistic observation.

[42:32] On the one hand, there's a structural reason for that now, which is that there are three of us full-time at The Generalist. So I run it with my wife. And then we also have a third employee, Kian, who's great. So now that is a very real reality. But I think probably to begin with... [42:51] I don't know. Maybe I was trying to project a greater size than than it really was. A greater seriousness that. Oh, I love that. I have a founder friend who he has this old doc when he started his company and he he's writing a commission statement. It's always. Oh, yeah. It's just me. Yeah. There's something where you're trying to say, like, listen, maybe it is just me. But like, you know, I'm I'm I'm staring. I'm swinging for the fences here. Yeah. [43:14] And then, you know, [43:16] not calling it the Mario show. I don't know. I really am allergic as much as possible to that, you know, attaching identity to work that directly like that. That feels really interesting. [43:30] I don't know why. A quote on observation, maybe. You say, the finest practitioners of a given discipline are often the worst at articulating their craft. It's kind of a tacit thing. Too much of their skill comes from inherent qualities or abilities illegible even to themselves. Better to watch these people rather than ask them to explain. Case against podcasting. Yes. What makes you good at watching people? Yeah. [43:56] I think I have a pretty good beginner's mind. Like I will really... [44:00] Uh... [44:01] enter something.

[44:03] with. [44:04] as much of a childlike openness as I possibly can. And, and, [44:09] uh, [44:10] especially if I think this person might have a secret in some sense. It relates to what we talked about at the top around sort of like making, reducing your own size a little bit to have it. Yeah. That's right. Yeah. Yeah. So maybe it's that. It's sort of that, that willingness to sort of, [44:25] be a little smaller in that space and not come to too many judgments in advance. [44:33] And also... [44:35] I find that many people... [44:37] R. [44:38] Hidden teachers. [44:40] if you present as the student, the teacher emerges. [44:44] And so... [44:45] A little naivety can go a really long way. [44:48] It'd be the dumbest one in the room, ask the question. Yeah, exactly. And people mostly take... [44:54] pity or in some sense on that person such that they will explain it to you. It's kind of like the say the wrong thing on the internet. Yeah, exactly. It's like an obtuse version of it, but there's an element of that. I mean, also, that's like one of the greatest... [45:07] intelligence gathering techniques of all time elicitation and you know sort of um saying the wrong thing so [45:14] Yeah, I don't mind that. I feel natural in a position of a student. [45:20] you have something about respecting your process. If you do your best work at 4 a.m. with a bowl of candy ginger, do that. Give yourself the latitude to be a difficult artist when necessary. Felt... [45:31] a little bit of [45:32] piece in reading that, but I'm curious if there are any dysfunctional habits that you've

[45:37] like allowed yourself to just accept. Yes, of course. I mean, I think there are many and I cycle through them. You know, there was a period, this is like, [45:47] But you, like, I guess, just to clarify, like, you've allowed... [45:50] I'm sure we all have dysfunctional habits. I have lots, but I'm not very good at like, except like, nope, this is just how it is. I have to like, this is going to be how it's going to be. Well, I mean, I suppose some of these things that I write are like things that I'm telling myself. [46:05] You know, there was a period where I was writing The Generalist very early on, and I was, you know, on a weekly cadence, sometimes a couple times a week. [46:15] I was going like as hard as possible, super fast. And for whatever reason, [46:20] when I would take a break, I would just watch YouTube videos where people would explain how to beat a certain horror movie. Like it would be like how to beat Saw. And they, it's like, you know, the sort of voice, how to not die. Yeah. And they'll be like, you know, well, if you think about how to, you know, you could use this tool to, you know, unplug this new genre. I've not, I'm not coming across this. That's hilarious. I almost don't have the stomach to [46:50] somehow compelling to me in like 10 to 20 minute increments okay and this goes against in some ways the ideal version i would have of myself of like no i'm a more [47:01] literary person who would who would pollute their brain with this nonsense but i needed it high low you gotta have high yeah exactly so you know that's a that's a

[47:10] That was my candied ginger for a period of time. I like it. You've evolved the generalists a lot over time. [47:17] one of the things I really appreciate about anybody doing something creative is they like, there's a mix of conviction and like a lightness to like rotate through things. Um, at a super high level, I think you have like a, [47:29] and maybe this is, [47:30] I don't know how old this is and if it's even still true, but somewhere you talked about sort of like the goal or the mission is to build the most thoughtful tech publication in the world. You talked about some other things too. I'm kind of more specifically interested in like, [47:44] specific goals. I had an experience... [47:48] last year where I had two very specific goals in a way that I hadn't in the past, which was, one was to get to 21 episodes of the podcast before mid-year. The other was to run the marathon. And those were both very like, [47:58] not, there was no like [48:01] input goal, there was no like, it was just like, these are hills I have to climb, and I can climb them by any means necessary. And so it was an experience of learning the value of very specific ambitious goals. [48:14] I think I mentioned this earlier, you talk about the equity... [48:17] uh, analysis meets New Yorker thing. Like that's kind of a goal, but more of a vision as well. Like, to what extent, [48:24] I mean, do you think about stuff like revenue and viewership and subscribers? Like, do you, are you, is it much more like putting one foot in front of the other? How do you relate to the kind of like ambition, raising your bar with specific kind of points on the horizon or whatever? Yeah, I think there have been definitely points in the journey where I've sort of said this year.

[48:41] XYZ subscribers, whatever it might be, uh, revenue, uh, [48:46] And probably more so like... [48:49] "Okay, this year we launched the podcast," or "This year we really give this a good effort." [48:55] I would say I probably think about that a lot less now because on some level – [49:00] I don't... [49:02] mind too much if we grow a lot in terms of like, [49:06] top line subscribers. It's 160,000 people. I would love more people to come in. That's great. You're like number six on business sub stack. You've done pretty good on that front. Yeah, it's good. I mean, it could be many, many times better, but I'm not convinced that having more people is better in that sense. I do think there's sort of this trade-off between popularity and influence. And I'm not sure. [49:32] I'm okay sort of [49:34] of focusing on influence and that could even mean a smaller audience in some situations um and so i don't really think about that i more think of like this year um [49:44] Can I write a piece that footnotes the last best piece I wrote? [49:48] Is that just purely a vibes thing? Like I'll know when I've done it. [49:51] Yeah. Okay. Yeah, I think so. [49:55] Good luck beating Founders Fund. That's going to be as far as high. I think I'll beat it this year. I think I will... [50:00] confidently beat it. Uh, but it was clear founders fund was definitely the best. Like, uh, there are other pieces maybe I, I love more or I feel, you know, closer affinity towards, but like, [50:10] So objectively, that was the best one. You talk about a debt to modernity. You say, to make an impact on the world, you must pay a debt to modernity. It is romantic to imagine succeeding just as your heroes once did, but they lived in a different time in different circumstances. A concession to the present day is necessary.

[50:28] Has there been anything about the past, especially as a writer, like has there been anything about the past that has been most tempting for you to... [50:34] to be romantic about or wish that [50:37] was the case. As someone who's been very good at building a modern media company, maybe. I think... [50:44] Just trusting... [50:46] that your work will eventually find a home and sort of its quality will speak for itself almost without caring about the distribution through the Internet. That was always super tempting to me. And it was why I wrote for 10 plus years before starting The Generalist, thinking that, you know, [51:05] This will once I do the work, it's just going to happen. [51:08] But that's not how things work. No. [51:10] No, and it's a blessing and a curse. Yes. Blessing as well, though. Blessing, yeah. [51:15] Many writers like find something that works and, [51:18] And then they like keep hitting the ball. I love Ben Thompson. Like he's added the pie cap, but like he is a thing that works. Yes. You have evolved a lot. You've explored so many different types of series, like in formats and even doing the podcast now. And it seems like you're shifting towards this much kind of maybe slower, bigger, more like why so much of that? [51:41] iteration, given that you've been successful kind of throughout? I think I have to keep it interesting for myself. Uh, I, I, [51:49] would not be... [51:51] excited to write the same style of piece for the next 20 years. I'm interested in many, many things. And I'm

[52:00] I want to pull down the bigger pieces that I can do as my ability grows. It feels like in some ways it would be unambitious. And I don't mean to cast aspersions on anyone else. Like everyone else has their own versions of ambition. But for me, it would feel unambitious if I was like, okay, I've developed a lot as a writer and a researcher and a thinker, and I'm going to just do it again. Why wouldn't I try and do something like much, much bigger and much, much deeper? That's harder. That's more interesting. [52:30] Like you need the friction. Without the friction. Little meaning. Yeah. So. So I'm. [52:37] I think it's a reflection of the fact that I... [52:39] I'm trying to learn a bunch of different things and hopefully the generalist is enough of a vessel to support that and enough of a vessel to support it as my ambition grows and I want to try and go bigger and bigger. [52:53] Have you kept anything constant? [52:55] Is there anything that's sacred? Yeah, the writing. I think... [53:00] There would be a version of The Generalist that I haven't been able to get behind where I had like many more writers or where I aggressively at this point used AI to write drafts and like. [53:15] It's close enough in some senses. I think the sacred part is just [53:19] really caring about [53:21] the sentences and the flow and all of that, um, in an obsessive way. And I think that was true at the beginning, uh, when I had less skill and hopefully true now, and hopefully true in the future when I'll think I was doing a terrible job now. Yeah. It's the cliche, like find the thing you don't want to automate. Um, I love David Senra talks about this and he's like, why people will be like, why don't you have someone read the books for you? And he's like, the whole point,

[53:51] you also have changed a bunch and explored a bunch of different business models and like variations of the business model. I found something in November, 2022, you were saying that like the paywall doesn't make as much sense, makes more sense to put content. [54:05] make it free. Sponsorship is a much better business model. I think you also had a core part, at least around then, a core part of the subscription was actually about this community [54:14] piece of it. Yeah. Um, a lot of sponsorship as well. Then generalist capital, obviously now humming, but like, [54:21] I'd mainly just be curious for your reflection on maybe one precise question, which would be putting like the, like the entire founders fund thing behind the paywall. I mean, I think you were thoughtful about how you did that, but like, um, yeah, [54:35] why the paid subscription actually makes sense, especially for someone of your scale, and then more broadly, reflections on navigating the business model side of all this and why you've landed where you have, even including monetizing it via investing. Yeah, I think... [54:51] There have been different... [54:53] seasons in a sense of of how i've thought about the business and where the advantages are and what i've come to realize is i probably thought about sponsorships versus subscriptions like much too much as a binary and i'm [55:07] It's... [55:08] Probably not an accident that every media company eventually sort of like tends to converge on doing both. I do think there are reasons why it made sense to be sponsorship heavy at the beginning, though, because you're trying to build the audience as much as possible. And so having more work open.

[55:25] like on balance probably makes sense. Um, [55:29] And then, you know, it can make sense, I think, more to have a subscription model when you maybe have like a really deep archive, like the value of what you're giving people just hopefully keeps compounding if the things are evergreen in some sense. So in some sense, they reflect the maturity of the business. But the things that really didn't work were. [55:49] We're the community and having that as a big part of the community. [55:54] And not because, you know, there were really some amazing people I met through that and some really good sort of friendships that formed. So I'm glad I did it. Because I've heard of, you know, from some folks that they ended up meeting sort of a co-founder or really, you know, good connection. But from a business perspective, I think. [56:13] It's really hard to do that, I think, well. It requires a lot of gardening. Yeah, and it's just not my strength. [56:22] And also we have such a... [56:24] various audience that it's not clear what people are sort of joining for. So, yeah. What about investing? Like when did that first show up? I mean, [56:35] You, I'm trying to remember, did you, had you done any investing prior to the journalist? Yeah. So I'd worked as a VC for a few years. Um, and so that was sort of, you know, part of the reason the generals has the lens it does, um, was, was coming into it with that, uh, that mindset. Um, yeah. [56:52] And I sort of never properly stopped investing. There was maybe like a year where I didn't

[56:58] do much. But pretty quickly, I was doing some scouting, then I was doing some angel investing. And then once the generalist felt like it was [57:07] you know past the stage of survival yeah then it was exciting for me to be able to do that more seriously with with generalist capital [57:15] and why [57:16] We'll talk more about Hummingbird, but why was it Generalist Capital and not plugging into... [57:22] a kind of bigger... [57:24] Entity, at least back then. [57:26] I think I was just like, I want to do everything myself at this point. I just that was the biggest lesson I had learned was suddenly I'd made. [57:34] much more progress than I'd ever made in my professional life and felt much more myself. So I couldn't, I couldn't conceive of the idea. It goes back to your answer about the authenticity question, actually, which is like letting, but like, it's all up to me. Yeah. There is. Yeah. So I, you know, I wanted to do it. Yeah. [57:52] I want to talk a lot more about investing. One place to start maybe is, I think also from the maxims, you say energy is a selling point. If you have nothing else, you can give a founder, at the very least, give them this. [58:03] How is energy underrated? Maybe specifically in this context. Well, I think a lot of people come into conversations, uh, [58:11] more wishy-washy or [58:14] maybe for good reasons, sort of more default skeptical, and you definitely need that as an investor. But there is a point at which, [58:21] You know, it can be sometimes intangible, but some point the conversation flips from one person selling to the other. Right. And I don't know if people always understand that transition or are ready for it.

[58:37] And I find that it is extremely powerful. [58:40] Uh, if you can be the truest believer authentically, um, you, [58:46] That's like that's really attractive to people in any walk of life. But but with founders, certainly. [58:53] There's one reading of this. It's just like, be warmer and more excitable. The last bit, you mentioned doing it authentically. Like, how... [59:01] even in terms of the energy you have to give. Some conversations are very energizing, and it's easy to have energy run off, and other conversations aren't. [59:10] Do you have any relationship to, I don't know, I don't want to say faking it, because I think that's actually definitely wrong, but how can you bring energy to the table consistently? [59:23] in a way that isn't [59:25] contrived i guess i i think of it you know [59:30] You have to perform. And not like an actor performs, but like an athlete performs. You know? Like you... Yeah. When the race is... When the starting pistol goes off, it doesn't really matter if you're... You have to show up. Yeah. You have to show up. You have to... [59:42] And that is a part of showing up. [59:52] You're not feeling great or I don't know the other person's not giving you much like your responsibility. Yes. [59:57] Yes. That rhymes with, I talked to Chris Peck about this as well. He has this, there's this episode of the bear, um, and he's talking about every second counts and he, he related to it that way, which is like this 8am zoom meeting I have, like might be the most important meeting of somebody's month. Yes.

[1:00:12] And like, I have to show up for that. And it might be the most important meeting of your life or year or, you know, maybe not life because, you know, that sort of discounts too much family stuff. But yes, you don't know what day I talked to Andrew Reed about this, too. Like, you don't know what day is going to be the thing you get pulled into the thing. You're like, oh, yeah, yeah, exactly. You don't know who's walking through the door. I think this relates maybe a little, which is you also talk about like this very special relationship of being the first check. [1:00:37] My assumption would be that you've had at least some amount of, or at least being close to that. What is so special about that relationship? I'd always heard that from other VCs where they were like, the reason I was able to double, triple down into this winning company relationship [1:00:55] despite it becoming insanely competitive was because I was the first one there. And I sort of was always a bit skeptical because I thought, well, I've had good relationships with founders. But I really do think there's something special there about being the first believer. And it's sort of the same thing. [1:01:12] thing as [1:01:13] I think Tyler Cowen has written about – [1:01:17] One of the best things you can do for a talented young person is just to have them say, like, you can do 10 times more than you're doing, essentially, almost dogmatically, just raising the ceiling for someone. And so I think there's something to that of just... [1:01:32] being the first person to say like, I actually see your talent and believe in you. And I think this can [1:01:36] be massive. Yeah. Um, [1:01:38] is very memorable. Yeah, I've talked with people more in the kind of like grants side of things, although I think there's actually some overlap with early estate investing, which is like,

[1:01:47] Sometimes the... [1:01:48] That [1:01:50] conviction is [1:01:51] maybe not more, but close to as valuable as the money. Yeah, 100%. I think much more valuable. Especially if it's a small dollar amount, right? Yeah, like you're the sort of... [1:02:02] Person who, you know, you're the boatman taking them across the river in some sense. They would have gotten across anyway, but. Right. Right. Maybe you pulled them, pulled them forward. Exactly. Exactly. [1:02:12] You say, "The best investors often need little more than a sentence to explain why they've invested in a company. The longer and more convoluted your investment rationale is, the more skeptical you should be of it." I've heard this. [1:02:23] pattern across certainly not just venture capital as well from different very successful people can you either give an example or reflect on like [1:02:32] the people you know who are very, very good at this, or the ways you even become like... [1:02:36] Yeah, what is that? [1:02:37] it's a really cool line to hear. And I think... [1:02:42] doing that in practice is actually like insanely hard. And so I'm curious what, either who's good at it or examples of it, or even just how you, you have this other thing where you're like, you say somewhere like, um, [1:02:53] It's not the same exact idea, but if a rationale can't be distilled onto a note card, then you probably don't have enough clarity. [1:02:59] I think for investing, there's often so much skepticism around venture, which part of it is earned, where people will be like, oh, the average VC, their rationale for something would be on a napkin or anything. [1:03:14] That's actually good. That's really, I know a very serious investors who are not VCs that have the same kind of mental framework. Yeah. Opportunities. Yeah. And in interviewing so many of these people through the generalist over the years and asking them about their best investments at first, I was really frustrated that a lot of times they would be like, this founder is just insanely good. And you're like, like what, but why? Like, you know, come on, help me out here. Um,

[1:03:42] And I think what you've come to come to realize is one, the best practitioners are not always great at articulating their craft. Right. And two is that like on some very deep level, they've actually parsed through a ton of information. And that's actually the decisive point still is just this person is special. And that's infuriating, I think, in some level more earned, maybe, by the way. Yeah. Like that's the thing you don't see is they've earned the ability to like let everything else fall away. Yes. And that for them saying this person is extremely good or insanely good. [1:04:11] mean something very actually quite specific. Yeah. Um, [1:04:14] To me, those are many of the best articulations of why great people invest in a company, even if it doesn't give you exactly what you want. [1:04:26] A couple of things on the, on the, on the maybe founders fund teal front. Um, [1:04:31] There's this thing where you say, I can't remember if it was in the piece or in a podcast, you frame it as sort of like Michael Moritz is like, [1:04:38] orientation is like do right and teal is be right which i think is there's i mean there's so much there but like i'm curious how you like where do you sit in that like how do you relate to that idea [1:04:50] Oh, interesting. [1:04:51] And I guess you could, obviously you could take that in this like very blown out kind of moralistic sense. But I'm also just curious about it in the investment sense. I think I'd probably not... [1:05:02] Axiomatic about [1:05:04] either case, but I would imagine I lean more [1:05:08] Moritz. There's some part of me that is more like, well, let's make sure we do everything kind of the right way. And I've come to appreciate more that you really...

[1:05:20] not in a legal sense, but in a sort of philosophical sense, need to learn when you're breaking the rules cleverly. [1:05:27] Well, and there's a tinge of it too. [1:05:29] around see the world as it actually is. - Yeah, that's right. That's right. - You also observe that Teal is, I think you frame it as, unusually creative at hanging on to talent. [1:05:39] Hmm. [1:05:40] Maybe in a broader sense, why do you think... [1:05:45] great talent hangs around, whether it be with Teal or otherwise. [1:05:50] Well, Teal is so smart in the sense that he's built like the Peter Teal cinematic universe of different entities. [1:05:58] And so... Rube Golder, you're just falling through the labyrinth of... Yeah, exactly, of Lord of the Ring names. [1:06:05] And... [1:06:06] And there's almost no incentive to leave. It's like, you know, Google having laundry on the premises and stuff like that. Like if you can give someone a great new mission, there's enough different kinds of roles and different scales of companies, etc., etc. that I think he has a lot of cards at his disposal that he can sort of... [1:06:26] make it easy for someone to find their next big thing. [1:06:31] You know, in terms of [1:06:32] retaining talent more generally in some sense i'm [1:06:36] like very much just learning that from other people but it feels uh like people are always sort of [1:06:42] maximizing some version of a few things of, you know, [1:06:46] compensation learning curve, uh, and autonomy. Maybe there's one or two others in there, but, uh, you're just trying to optimize for, for that configuration for different people. My sense is there's an element of, um,

[1:06:57] at least with teal. [1:06:59] But maybe in that second thing, too, is... [1:07:02] One of the things that really compounds and is really hard to start in it with is trust. [1:07:08] Yeah. And so like... [1:07:09] If you can manage those other things you said, you get to stay in the field of trust, especially for Teal, that is – [1:07:17] that really [1:07:18] compounds you think about like any of us for any of our relationships like when you're in year eight with somebody it's it's a very different thing than rebuilding i think that's very true and i think it's especially true with him because the people that stick around seem to hold him in just insanely high regard uh such that i think if he says you should go do this thing you're like i don't know i i think i probably should yeah he tends to be right yes exactly uh [1:07:46] I know you are generally... [1:07:48] oriented towards founders and how you think about investing, you've described Hummingbird as the best founder-focused firm in the world. A couple of quotes. You say, you cannot expect to underwrite founders well if you do not focus your attention on who they are. Too much time is spent on CAC, LTV, and product features, and too little on the texture of someone's mind. And then Hummingbird's chief virtue is its ability to ask questions that give these anomalous founders the comfort to open their metaphorical ice boxes and reveal the strange [1:08:18] raw edges of their personality inside. I'd love to hear you talk more about the texture of someone's mind. Um, and then maybe around that, how do you ask questions or how do you approach things in a way that creates enough intimacy for some of that to actually come through, given that these relationships are often formed pretty quickly? Yeah, it's really hard to, to do that. Uh, I,

[1:08:42] People seem to have their own ways of making that happen. [1:08:46] You know, Barand, I think, has a very unique genius of, like, creating that environment for people, sometimes almost... [1:08:55] Out of nothing instantaneously, you know, there's a there's a yeah. [1:09:00] a sort of divine genesis that yeah a jujitsu move or something right it's pretty remarkable um farat you know the other um that you know the managing partner hummingbird has his own way that again is like [1:09:12] pretty magical to see. So I think everyone has to find their own style. I think, you know, you're having to do that in a podcast. You know, you're having people sit down probably the first time meeting them and asking them really deep questions. So you have a way to do it too. I [1:09:30] that I've seen at least, [1:09:32] or I don't want to say most, certainly many, uh, [1:09:36] almost haven't oriented themselves to do that. They're almost more information gatherers. [1:09:44] And I think that serves them well in lots of, you know, in lots of environments, in lots of places. [1:09:50] But Hummingbird does something very different. [1:09:53] And it's much more similar, I think, to what you would do in this sort of a conversation and what I try and do in the generalist. [1:10:01] And so that just like speaks to me and makes sense to me in some way. Yeah, what's interesting about that is, [1:10:07] I have some challenge in what I do, but I also have no quote unquote, it's, [1:10:11] ulterior motive. In theory, my job is just to make

[1:10:15] Maybe if you want to be more cynical, just make the best content. And really what I think my goal is, is to make the person shine in a way that I see them or whatever. Whereas... [1:10:24] What they're doing or what you're doing now is – [1:10:26] is that maybe partially, but it's also, there is this objective function running through it. And if both parties know this, which is really fascinating, like, and there's a little bit of like, [1:10:35] I'm sure performance, but also it's, it goes back to the story underneath the story. Yeah. There are, you know, there's always the game in the meta game. Yeah. Um, and, [1:10:44] And, uh... [1:10:46] Yeah, I think personally, I think that's happening. [1:10:49] In every conversation. I think I think that's true, even for a podcast or even for maybe maybe not with your very dearest people. Sure. But but probably at some level. Right. So or in some way, it doesn't always have to be, you know, it sounds so cynical. I don't think it has to be. [1:11:08] So that is there, but I think it's there all the time, whether you sort of see it or not. Yeah. A related piece to kind of the texture of somebody's mind around motivations. It was less about let's go into the weeds and tell me why you invested in this company. It was more around, hey, man, why are we sitting here? Why are you doing this? And why are you building the firm the way you're building it? [1:11:29] How important is, maybe I'll backdrop it, we both know Anjan Kata well, who runs Daylight, and Anjan is a remarkably idealistic founder, deeply mission-driven. And there are personal motivations inside of that mission, but it's idealistic. So my question is, how important is the why, in the almost external sense of the mission, versus...

[1:11:57] the like quality of ambition and like the fuel around like the person's [1:12:03] I don't know. Um, [1:12:05] I have something to prove or something. Does that delineation make sense? Maybe I'm forcing it, but there are two different kinds of motivations, maybe? Yeah. [1:12:15] I think you have to have the second one. [1:12:17] I... [1:12:20] Think you can also have the first one? That is not a given. I don't think that most people are taking that input. Like, I think many people might actually assume the inverse. Yeah, and that would not be my observation so far. Right, right. I think the second one's actually at a much deeper level and is, like, much more essential to your personality and the way that you grew up and, you know, the way you're formed. Right. There's a... [1:12:47] idea that Barron talks about that reminds me of, I've heard other investors talk about, Chris Peck frames it as like, are they post-death? Barron says, or this is you writing about him, how did it change them? What residue had it left on their selves, their souls, their lives? In particular, he, Barron, was interested in how many entrepreneurs had undergone something that affirmed their fragility, their mortality. He hoped to convince founders to share such experiences, creating a kind of compilation of hardship. It relates to the prior question too, [1:13:17] Thank you. [1:13:18] I assume you're familiar with the good fuel versus bad fuel frame. No, what is that? Sort of like bad fuel would be like... [1:13:27] there's like a remarkable Patrick was Sean, as you will talk about, like there's a remarkable number of really successful people. Who's like dad died when they were 14. Ah, yeah. Um, yeah.

[1:13:35] Or just some kind of self-punishing. And good fuel, I think, can be very internal. It can be this artistic, kind of authentic. But it could also be like, I need maybe the idealistic thing we were talking about earlier. It sounds like, maybe I'm answering my own question, but it sounds like you're kind of saying... [1:13:51] The importance is that there's fuel at all, like some kind of rich fuel. I guess I need to read more about it, but I'm sort of skeptical about the idea of good fuel. [1:14:01] Ah. Maybe that's too cynical, but what's an example of truly good fuel? I think the... [1:14:10] I would say someone like Rick Rubin presents as [1:14:15] Somebody who's just like doing it for the love of the game. There was this whole thing recently about Alyssa Liu, the figure skater, the American figure skater at the Olympics. And she had quit. And like she literally competed in the last Olympics. Overbearing dad. Quit. It was like, I don't love it. It's like too intense. She took two years off and she came back and was like, we're doing it my way. Like, I have to do this for love. I have to do this for art. And she won the Olympic gold. And like, obviously, some aspect of that is somewhat romantic. [1:14:45] grind. Yeah. But like, [1:14:47] It seems broadly that as you, and maybe it's just a narrativization thing, it's stories, stories we tell ourselves. But as artists, as people become more successful over time, in theory, at the very least, people tend to shift from bad fuel to good fuel. I see. Something that allows you to go farther, longer, and so on. Okay, I could see that. To me, though, that's a story of you had this thing that made you who you were, and that forced you to become great.

[1:15:17] level yeah you you find new sources of energy and and things like that but i don't think you become the person [1:15:24] who is able to manifest this good fuel without the overbearing dad story like i i don't know i have not seen someone who's so well adjusted and and seems like full of ambition like there's always something people might tell you that's the case i mean there there are founders you talk to who said oh i had a wonderful childhood and then you'll find out 10 things where you're like you had a wonderful childhood i mean this is actually um have you ever seen the documentary [1:15:54] these guys who are trying to surf. The Lord Hamilton type guys? Yeah, like the newer generation, older generation. [1:16:00] They're going to Nazarene, Portugal, trying to surf these monster waves that, you know, if you fall, you're like falling off a skyscraper. That's moving underneath you. It's insane. No one should try and do this. But these people are doing it, and I hugely admire them. But the sort of protagonist is this guy, Garrett McNamara, this old sort of grizzled surfer. [1:16:20] And, you know, his wife's like, yeah, he always says he had this great childhood and that he has a great relationship with his mom. Meanwhile, you know, he got separated from his brother as a kid. He was raised in a cult for a period of time. He had no shoes, no money. You can't trust the narrative. [1:16:36] I genuinely would be, I don't say this to be dogmatic. I would be sincerely interested if someone has like a case where they're like, this person was hyper ambitious and is, [1:16:47] came from a very, very, very well-adjusted background. Yeah. Yeah, there's a...

[1:16:52] there's a kind of a tenor of tenacity throughout a lot of stuff you've written about, but especially the hummingbird stuff, like almost a ferociousness that runs through it. And I think an important backdrop for this also is like, we're not even just talking about a specific type of, like some level of ambition. We're talking about kind of like true world beater kind of elite, elite performance. And there is... [1:17:18] Again, it maybe comes back to seeing things as they are, which is like, [1:17:22] - What does it take? It takes everything. - Yeah, it takes everything. [1:17:25] And, you know, even when you look at these stories, sometimes maybe they look like they... [1:17:31] They had a lovely childhood, but because of the way this person's mind works, it was torture. There are different ways that people perceive the same set of circumstances. So anyway, yeah, I think it takes everything is the right way to put it. [1:17:47] There's a bit at the end of that hummingbird piece where you're talking about messiness in the same theme. Hummingbird's greatest talent is that it sees the world as it is, not as we think it should be. It meets reality and invests in it. [1:18:01] as it is. It is a pragmatic act, but it is also a philosophical one. By successfully investing in the world it sees, Hummingbird affirms reality's integrity. Wanda Brand and Larry can generate a return by capitalizing the unreasonable because innovation is unreasonable. Because progress is messy, we scrabble with fingernails full of mud. We pound our bodies bloody against a barrier to

[1:18:31] we do not like, and still we should feel grateful for them. This is the world as it is. Beautiful writing. I think my question would be, [1:18:40] This almost feels a little bit at odds with your obsession with stories. And clearly it isn't, but... [1:18:49] this radical obsession with what is truly, grittily real, without any of the... Even when you're talking to Baran, he doesn't want to tell stories about himself. And yet you're someone who is... [1:19:01] without losing any rigor, or even necessarily what is true, [1:19:05] A lot of your writing has a poetic nature to it. Do you see what I'm getting at? It feels like in theory there would be some conflict between these two things, and yet it doesn't seem that there is for you. It's telling that you have just joined this firm that is so radically obsessed with this. I guess I think that stories are really true, or the best stories are the one that is sort of truest in some sense, [1:19:35] way um yeah yeah and yeah i think the same is true of poetry right poetry is sometimes just so acute um that it says something much more truly than uh dispassionate facts could and so uh that's maybe the the place where those two things meet in some sense [1:19:58] I like that answer. [1:19:59] There's just a short bit where you were...

[1:20:02] you had met with Gort and Nomads when you were raising for the generalist. Gort, maybe I have that name wrong? Yeah, no, I think that's right. You say, Gort and his colleagues asked questions I received from no other LP. It was reminiscent of conversing with a relentless, precocious child, each question begetting another. What type of founders did I look for? What did that mean? What did that mean? After three or more of these burrowing questions, you begin to realize what you really think and how deeply that thinking goes. [1:20:29] I'm probably projecting a little, or I'm expanding it out to maybe the broader hummingbird kind of world. [1:20:34] But I'm curious how you and now your new-ish team, how that vibe or that tenor or that maybe even specific way of doing things comes up. [1:20:45] in the daily work, in the work with the founders, in how you even challenge each other. It definitely comes up, I think, in how we challenge each other. Like, you know, we'll talk a lot about a meeting we had with the founder, and okay, he said [1:21:00] this thing like what i thought it meant i thought he was sort of this is how it made me feel or this is what i observed ah like i didn't notice that or [1:21:08] I actually totally parsed that in a very different way than that. [1:21:13] You know, I think earlier in the piece, uh, [1:21:16] Salar, the CEO of Monumental, talks about Barand being the most linguistic VC. I was going to bring that up. [1:21:24] I think I would compare you in some way. Yeah, I mean, hopefully I'm linguistic. I have to prove that I have a long way to be at Barand's level from an investor perspective.

[1:21:35] But yeah, there's an obsession with words, language, down to like an insanely granular level. I can't overstate that, honestly. Maybe it relates to you earlier. [1:21:46] point about stories and like how much context, how much is, how, how much resolution is held within them. Um, one reading would be that like overly focusing on words is like missing the forest through the trees. But the other reading is telling that they also compare it, they're comparable in the linguistic sense to Michael Moritz, who's kind of known as this obviously legendary, but also very intuitive. And I think that it's, it's almost like taking words so seriously that you know how much is possibly contained in them and thus like require actually [1:22:16] uh, consideration, precision, evaluation, whatever. Yeah. Also I have to say, it's not just the words like there's, there's like a huge body language, a tone thing. Like there's [1:22:27] Uh, [1:22:28] You know, in... [1:22:30] If he was a therapist or a psychological profiler, he would be elite. Same for Farah. They're just hyper-observant about everything, and words just happen to be a big part of that. [1:22:45] you [1:22:47] A couple months ago now, joined them full-time, maybe longer. And you wrote about this in that piece. You said, for six years, I had built the generalist on the conviction that I am only truly myself inside of the structure of my own design. You talked about this earlier. When I thought of prior versions of myself, they always seemed ponderous and hazy by comparison. Because of that, similar approaches from funds to join forces over the years had been met with an automatic refusal. But in this instance, for the first time, a refusal did not instinctively arrive.

[1:23:17] Rather than being forced to fit a certain form factor to evolve in a specific way, Hummingbird might actually sharpen what made me different rather than sand it down. Obviously, this rhymes a lot with the earlier stuff around authenticity and playing your own game and kind of leaning into your strengths. [1:23:32] What were the... [1:23:33] I'd love to do a show. You talk about the emotions... [1:23:37] going into that decision, maybe the things... [1:23:40] Time will tell, but the things lost, the things gained, maybe the ways you're noticing yourself sharpening even already. [1:23:48] My... [1:23:48] Ability to observe and ask questions has definitely, like, I think. You can discover some things for yourself, but somehow seeing two people who are sincerely world-class at this, you can't help but observe and... [1:24:05] you know, look back on a conversation and think, how did they, how did that exactly happen? Or, you know, all these sorts of things. Um, yeah. [1:24:13] So that to me has been... [1:24:16] Yeah, like a real... [1:24:18] gift and something I've loved so much about that period. You know, I think the [1:24:23] feeling I have so far and it's been proven very true over the past year plus has just been like how intuitive it has felt. I never thought I would find a place where I'm, [1:24:37] I really sensed I fit in and we had sort of like the same ability to connect at this like very high fidelity. [1:24:44] beyond maybe your very old friends or your spouse or your partner um

[1:24:49] And this was a case where in a very small number of meetings, it was like a real mind meld, but also where there's enough diversity that keeps it sharp and allows you to spar well. So. [1:25:03] The experience with joining Hummingbird was really almost this massive intuitive pull, even as like some set of rules I had almost set for myself held me back at first. I was like, no, no, no, but don't forget, you're only good if you do your own thing. And at some point, I think I learned to let go of that. You seem to have... [1:25:25] this maybe relates a little to the evolving the generalist, like you do seem to have a healthy relationship with your own kind of structures. [1:25:32] And maybe this was a pretty rigid one, but you seem to be pretty good at allowing them to serve you and then being able to drop them or evolve them as... [1:25:40] As things change. Yeah. I think someone shared the saying, sometimes you have to know when to kill something before it kills you. And I think there's something really true about that. And I may be particularly minded towards that. I'm okay killing off things early. Yeah. [1:25:59] You say, learn to respect the process of the unconscious mind, especially in creative matter. Sometimes you cannot chase the answer. You must wait for it to come to you. [1:26:07] Maybe it wasn't quite like that for this decision, but I am curious about how much of an actual [1:26:13] will I, won't I decision it was, where you really had to sit and weigh the rationale, or it was just something that quickly became, or maybe not quickly, but...

[1:26:22] eventually became [1:26:24] inevitable and so obvious i definitely weighed uh the rationale when i sort of was first uh starting to work with them as a venture partner uh just because of i think some of the lessons of the previous years and and so and also it's just the way i'm a little bit wired where i want to like analyze something from every possible angle before i um i'm [1:26:46] I commit. And I think you have to be [1:26:49] willing in some sense to [1:26:52] change your mind up to the last moment of something. You know, you never know what information or signals you're going to get. And so I think sometimes we can overcommit to something different. [1:27:03] Too fast. You know, you want something to be true. And so there was certainly plenty of that. But I will say that from the very beginning, there was like some intuitive sense that this is right. And so it was really more about me, me checking that. [1:27:21] Is there anything you think you've lost? Or maybe a better way of asking the question is like, [1:27:25] Is there anything you feel like you really had to give up? [1:27:28] Yeah, of course. I mean, you you give up total control of your schedule, right? Like there there's a level of control that I get to have just when the generalist is, you know, my thing where. [1:27:42] If I don't want to do any meetings for... [1:27:45] a week. That's totally fine. This firm, apparently, people are meeting 30 companies a week? Yeah, sometimes. Insane!

[1:27:53] Not me, but people on the team are. I was like, there's no way these pieces are good. No. I mean, frankly, Hummingbird's insanely... [1:28:02] anti-structure so I think if I was sort of like hey [1:28:05] I need time to work on something. There would be no problem with that. But ultimately, you don't want to disappoint people that you're working with. And so you want to not be the bottleneck in anything. And so there's just a different level of... [1:28:20] that you have to have in the same way that you know when you're a [1:28:25] either a single adult or, you know, someone without a child or without a dog or, you know, any of these things, there's just different levels of wrangling and planning you have to do to [1:28:36] accommodate other other people's needs yeah [1:28:39] Yeah, we match. We... [1:28:41] we meet the intensity required yeah exactly uh and for the most part i feel like that's [1:28:47] been not something lost but like something that has been actually really good for me yeah yeah [1:28:52] Haha. [1:28:53] One other maxim, you say picking a career your seven-year-old self would find exciting is a pretty good heuristic. You know yourself better at seven than at 22. [1:29:05] How does your current work or your current life fit maybe what seven-year-old Mario would have aspired to? Well, I think seven-year-old Mario loved writing and books and also then went through a sharp turn, maybe around eight or nine, into wanting to be a trader in the stock market. No way. So there's some good threads there. Easy plug.

[1:29:32] You also talked about, you were talking to somebody and you were saying like one of the most generous things you can do for somebody is to push them like – [1:29:38] well beyond what they're expecting of themselves. You alluded to this earlier too. You talk about scaling your own kind of expectation of yourself. Um, [1:29:46] this relates to maybe the conversation about being able to drop things and so on. How do you... [1:29:53] How do you almost like build rhythm or systematize or something like build, um, [1:30:00] consistency of like continuing to raise the bar or like widen the aperture? I think the secret is being a very dissatisfied person is having deep psychological issues. No, I mean, I'm sort of joking, but there is something where I'm just congenitally [1:30:17] dissatisfied with the state of things. And that's [1:30:21] you know, the... [1:30:23] the thing that most philosophy, certainly on the Stoic front, or something like dedicates you to be grateful for what you have and accept what you can't control. But as much as I admire those philosophies and read them, I don't. [1:30:37] Something doesn't seep down to the bedrock. I'll invert it then. What are you most... [1:30:42] Or what have you been maybe at different stages, like other things that you have been most proud of? [1:30:48] There are a few minutes after a piece I've written goes out that I feel sincerely proud. [1:30:56] And that almost immediately transmutes into anxiety and expectation. But yeah, sometimes that can last more or less time.

[1:31:06] Um, [1:31:08] There are sentences which I'll read sometimes and still think, hey, that was a good one. So some of the ones you've read, I think when I hear you read that, I think, oh, that was good. I haven't stumbled over them too poorly. No, no. And then there's some you read and I think, I got to get back in there. Like, I want to tell you that. Can't do that. Can't do that. [1:31:26] Honestly, a good string of words makes me proud at times. Yeah, it should. I have a handful of kind of... [1:31:34] miscellaneous things before we wrap up. Um, [1:31:37] First of all, you, and I would encourage people to read it, I think it was in your 2026, like, [1:31:42] it's almost unexpected. It's like a list productivity stack or something. Yeah, it is unexpected. You have this just amazing, you talk about how you use Cloud basically in all of these amazing ways. [1:31:52] even for something as simple as like you say GM in the morning and it like prompts you on all these, like it's really cool. Um, as well as like using it as this really robust, um, [1:32:02] personal tutor and sort of building a personal curriculum. I've talked with other people about this. We were just talking about Henrik's early lives, geniuses, like this tutoring thing. [1:32:10] I think my question is a little higher level, which is just like you have – [1:32:14] Maybe it's actually what we were just talking about, but you have this seeming... [1:32:19] level of like a deep level of intellectual humility. [1:32:22] in the way you show up, in the way you [1:32:25] And I'm sure part of that is what makes a good writer and a good investor and so on. But [1:32:29] Is that something you aim to... [1:32:32] to develop or maintain [1:32:34] I mean, I hope I don't lose it. I think it's mostly true. I think there are probably things where I'm sure someone...

[1:32:40] in my life would be like, actually Mario was like an egomaniac about this. You know, we all have our flights of fancy, but... [1:32:48] No, I mean, one of the things that I think you learn... [1:32:51] studying great founders, reading great books, [1:32:56] is like, wow, I'm barely scratching the surface here, right? Of what ambition means, of what greatness means, of what doing great work means. So, yeah. [1:33:07] Yeah, I wouldn't want to foreclose my ability to... [1:33:13] to create great work by imagining I've arrived? Yeah, I think the answer is fairly similar to the previous question, but I respect that a lot. I also just love, like, yeah, I would encourage people to read. You're like, I don't know enough about Genghis Khan, and I don't have really time to read about Genghis Khan, but, like, there are a lot of ways to learn. One maybe element of this, actually, is, like, you... [1:33:35] Claude created a pedagogical approach to teaching Mario, like Markdown Dog. [1:33:43] How do you make yourself more teachable? [1:33:46] Hmm. [1:33:47] Well, the great thing about these AI systems is, [1:33:50] It has to figure out how to teach me. I don't have to make myself that much more teachable. Most people aren't. [1:33:54] Again, part of this is just like, [1:33:57] You're right. Part of this is you have an intensity and desire, but like people are trying to learn with these things a lot of time and they're not they're not as effective as you. Maybe I guess I'm. [1:34:07] how do I make myself more teachable? I mean, I give it a lot of feedback. I'm like, this was a terrible way to teach me. Or, you know, why are you in, you know, sometimes they will index on a set of questions where I'm like, these are actually not deep questions, what you're asking. And so you can sort of,

[1:34:23] take on the role of the precocious student who is questioning the teacher. Versus like, ah, isn't that good? I'm going to stop. Yeah. Yeah. Cause it can get better. Uh, and also, uh, [1:34:32] if you tell it to like, it'll also push back on you where it's like, Hey, I actually think this is a deep question. Uh, and so I actually have learned to more or less trust, uh, [1:34:42] that pushback where, you know, sometimes I'll push back and they'll be like, I think you're actually maybe letting yourself a little off the hook. You should understand this. Um, but, [1:34:50] And there's productive sort of conversation there. And then I think the things that you have to do to make yourself a good student are force yourself to articulate what you've learned. I mean, that's just the difference between. [1:35:02] consuming and learning. Also a very strong case for writing. Yes. Yes. I also really enjoyed your, uh, kind of notes summary on improv. Um, and there were a couple of things that stood out. One is, [1:35:14] you're, [1:35:15] there's this huge section on status, like learning to play status. You say, one bit stood out, a CEO who wants employees to brainstorm creatively will have much better luck if they lower their status rather than raise it. No one writes poetry in front of a firing squad. In what ways are you actively holding that model in your head or holding this kind of play status thing in your modes as a writer and as an investor? [1:35:39] Hmm. As a writer, that's really interesting and I haven't thought about it too much. Yeah, maybe investors a little more intuitive. Yeah, as a writer, probably I'm playing high status a lot of the time. [1:35:49] Well, there's sort of something almost default high status in saying everyone should read this.

[1:35:56] But hopefully there are times where I can play low status in writing. Also, I would imagine in the, some of the Founders Fund, like you're, [1:36:02] or really any of the entrepreneurs you work with, [1:36:05] the [1:36:06] Imports. [1:36:07] maybe are more low. Yeah, 100%. Yeah, yeah, definitely. And then you are sort of hopefully emerging as at least some kind of authority. Yeah, yeah. Otherwise, why are you sharing it? There are obviously styles of writing where you can play low status, like comedy writing, you could certainly play low status. Investing, I think I'm definitely... [1:36:27] always interested in what the person is playing and how fast they can flip. Are they a status expert, as Johnstone would say, where they can play low status if it suits the situation and high status at another moment? [1:36:42] He also talks about unlearning. And I'm curious if anything immediately comes to mind as things you've had to unlearn. Yeah. I mean, I think so much we have to unlearn, right? Like our, I don't know if this resonates, but. [1:36:54] I don't know. Most advice you're given growing up as a kid from like authority figures is mostly not good. I actually think the advice my my parents gave me was really good. But teachers, things like that, you know, I. [1:37:08] You learn to set in your mind a very specific set of options that are the realities. There's much more available to you. Certainly. Maybe have there been any things that have been particularly hard to unlearn? [1:37:24] Hmm. [1:37:25] Hard to let go of, almost.

[1:37:28] I think there's something about... [1:37:30] learning to let people meet you halfway on things. [1:37:36] Yeah, I've had to unlearn some some aspect of like going the extra mile and that in some situations, that's actually really not the right thing to do. [1:37:47] pragmatically but more sort of [1:37:49] spiritually philosophically um so that's something i i i'm still on learning [1:37:56] I don't know that these are at odds, but you also write about [1:38:00] You have lots of great advice about being good at asking or being good at helping people, allowing people to help you. Yeah. [1:38:07] which [1:38:08] at least on the surface, could be a little at odds with the halfway thing. Definitely. How do you think about that? Because I think you seem to at least perceive yourself to be quite good at the asking thing. Yeah, I think you have to go above and beyond when you're asking. But when you're being asked, sometimes people will ask you for something, but they actually kind of want you to go 90% of the way. Yes, yes. And that's a place. Let me help you. Yeah, and I think that's a place where you can learn to maybe hold that ground a little bit more. [1:38:37] holding your ground is a good, is a good mental thing to hold on to. Um, [1:38:43] I love this. This is just kind of out of pocket, but you said most products people contend have taste, show no sign of true deep quality. They simply encapsulate the aesthetic preferences of a high signal group. When someone says this, better to think of it as someone telling you, I am this kind of person.

[1:39:01] What, and I think you, if people want examples, you do a, you, you list all the things you use, but what, what is a sign of true deep quality in a product? [1:39:09] generosity, [1:39:10] sort of meeting the user where they are. And I think that's actually true of writing as well. [1:39:17] There's a lot of writing that almost assumes a huge amount of knowledge. [1:39:21] And you have to calibrate it, you know, for your audience. So it wouldn't make sense for me to start every piece talking about what technology is or what software means. But I do think by and large, there's not a lot of generosity in product and in writing. And so, you know, that could be as simple as having like a really beautiful empty state or onboarding or whatever that might be. [1:39:50] I... [1:39:52] Yeah, I think there's more to be done in that. Even the last two things you said, Silicon Valley claims to be obsessed with. [1:39:57] Perhaps this is your point, but like, yeah, I don't, I don't. [1:40:01] Uh... [1:40:02] We want to build delightful products. Yeah, delightful. But delight often just means like there are really nice gradients or there's like a really great dark mode or something like that. I don't know. I do think there are people who care about this deeply and there are obviously many beautiful products. But we also set in place like a set of really strict heuristics at various moments of what we think good is or how certain things are supposed to work. Right. And it seems to take a long time for us to interrogate those things.

[1:40:32] anew like even just now the way that we're seeing finally some different form factors around consumer electronics and hardware emerging like we've been really fixed on a certain form factor for a really long period of time and there are things there are good reasons why that's the case and there's been lots of attention given to making it [1:40:49] effective and efficient in certain ways but i'm not convinced that it's right or it's generous or you know it has some of these qualities that um [1:41:00] I'd want to tie myself to too much. Yeah. [1:41:04] You wrote that you spent nearly a year studying what may be one of the most important companies of our era. Curious if you can give us any kind of teaser for what that might be. Oh. [1:41:15] It's okay if not. Yeah, I mean, I think it will be obvious what the most important companies are right now in the world, right? There's a certain set of companies that are changing the technology industry. [1:41:29] And, you know, [1:41:30] playing major roles in the way that [1:41:32] Great power conflict is being waged. And so hopefully I can write a piece that captures one of those companies at a really low. [1:41:42] deep level of fidelity. [1:41:45] Are you still working on the novel? Yeah. [1:41:47] As if there were not enough things. How's that going? How is it going? It's going quite well compared to a year ago. Okay. [1:41:57] I started working with a really incredible editor, a writer.

[1:42:03] Who is like one of the most... [1:42:07] acute readers I've ever met and who has been, [1:42:13] been able to diagnose some of the things that I've [1:42:16] felt were wrong with it, but couldn't [1:42:18] put my finger on enough. [1:42:21] And so I've really learned a huge amount about [1:42:25] that [1:42:27] Yeah, about structuring things and why certain things work and certain things don't that I was missing before. Right. [1:42:36] I actually feel I'm the closest I've ever been to... [1:42:41] getting a version that I'll be happy with, but I'm also... [1:42:45] very aware that my time is sparser than it's ever been. Um, and so I'm kind of, [1:42:52] That's the part where I feel a bit upset about or a bit stressed about where I'm like, I can now kind of see how to get there for the first time. But I need it's you know, it's not going to magically happen. So who knows how long it will take. [1:43:09] Something interesting about maybe a great editor can be generous in the way you're talking about the same with products. Yes. Yeah. People often talk about things they most regret. I'm curious to flip that for you, which is... [1:43:21] if there's anything that comes to mind that you're most glad you did. [1:43:24] I mean, the most obvious one is go to my best friend's or one of my best friend's birthday parties and meet my wife. That one's certainly...

[1:43:36] the best thing I ever did. [1:43:39] And the best professional one is undoubtedly start the generalist. If I have to go back a little further, I would say take a night school class at NYU while I was working at a law firm for fiction writing. [1:43:53] and [1:43:55] begin as a 22-year-old to imagine that you are supposed to be writing every single day, not just being sort of a good writer in school and writing when you feel like it. That sort of forced a habit that... [1:44:08] Uh, [1:44:09] I think I would not have been able to do the generalist as well if I hadn't started at that point, like taking it super seriously. Sort of becoming the person you imagine yourself to be. Yeah, exactly. [1:44:23] You mentioned your wife. You say, love is easy. The difference between bad relationships and meeting your spouse is not a matter of degree, but category. Compatibility is unignorable and effortless. [1:44:35] That's a wildly opinionated and probably a banger. [1:44:42] How does your wife make you better? [1:44:44] I almost disagree with the premise. [1:44:48] Like, I don't... [1:44:49] She makes me better in many ways, but like, why... [1:44:52] that's too focused on me you know she's just incredible in in every in every way and not because she does something that like [1:45:01] changes my chemistry. [1:45:04] Yeah, most people, I think Kate Hall had a really good post being like, I liked a lot of Mario's observations, but I totally disagree with this one. So, people feel differently, but for me it was just

[1:45:15] Yeah, so, so obvious. [1:45:18] and so effortless. So I'm very lucky in that sense. So she makes me better. But yeah, she's just miraculous in her own sense. [1:45:28] I have one last thing. A pair of quotes, I suppose. This is you first. Over the course of my career, I have imagined many paths for myself, but the best have always felt like a mix of shock and inevitability. I would never have thought of running a newsletter, and yet once I'd begun, it was strange that it had taken me so long. So many of the best things that have happened to the publication, to my investing, to my thinking, have arrived from directions I did not anticipate. And then a quote. [1:45:56] from Oscar Wilde, who I think Byron brought up with you in that joining Hummingbird piece. Wilde says, if you want to be a grocer or a general or a politician or a judge, you will invariably become it. That is your punishment. If you never know what you want to be, if you live what some might call the dynamic life, but what I will call the artistic life, in each day, you are unsure of who you are and what you know will never become anything. [1:46:26] Mm-hmm. [1:46:27] How is this reward of not knowing, of being maybe a generalist, we could say, how's that going? [1:46:35] No complaints so far. I think... [1:46:38] I think that remains one of the truest things that I believe about myself is that I really don't know what I'm supposed to become still at this point. I know there are some things that will always be true. I'll always love writing and I'll always love stories. And I'll always love sort of studying these fascinating, incredible people that tech has an abundance of.

[1:47:03] But I try not to get too attached to the certain form factor. [1:47:08] myself in a few ways in the years ahead. Onwards. Well, thank you very much. That's all I got. Thank you. [1:47:15] As a reminder, you can find all notes, transcripts, and links at dialectic.fm, and in this case, slash Mario-Gabrielli. Thank you for listening to my conversation with Mario. And once again, I'd like to thank Notion for presenting Dialectic. Notion's biggest new product is custom agents, and custom agents are really just a remarkable way to bring in collaborators to how you and your team work. As I mentioned, these can be really small and almost trivially simple in just ways that [1:47:42] remove little bits of friction. But increasingly, these can also be quite ambitious. And I'm excited to see all the ways that I can continue to collaborate with a team of agents to build out dialectic. Also, if you enjoyed the conversation, please give it a thumbs up or five stars wherever you're watching and also subscribe. It actually really, truly helps. And if you do subscribe, it will ping you anytime there are new conversations. I've got lots in the hopper. I can't wait to share with you. Thanks again, and I'll see you next time.