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 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