43: Mario Gabriele - Reality is Story-Shaped

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.

Um, that's so good.

Founding The Generalist was like in many senses the most authentic thing I'd done professionally. Have not seen someone who's so 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, "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 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?

Wow, that's a really interesting observation. I hadn't put that together.

Welcome to Dialectic, episode 43 with Mario Gabriele. 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, uh, that is much more narrative and makes it incredibly engaging to consume and to participate in. 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. Mario is also a partner at Hummingbird Ventures as of a couple of months ago, and previously was a venture partner there, as well as the founder of Generalist Capital, which he was running alongside the publication. I think he's deeply attuned to what feels true to him, but also 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. 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. Before we get into the episode, I'd like to thank Dialectic's presenting partner, Notion. 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 as well as synthesize them as I go through all of the lessons and patterns across individual episodes and across the broader body of work. I think in many ways Dialectic is 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. With that, here is my conversation with Mario Gabriele. Here we are. Mario Gabriele, thank you for being with me. Being here with me, I should say. Being with me. Uh, and I'm, I'm sorry I didn't nail the Italian pronunciation. Alas, I did my best.

No, I think, uh, a very good one. Uh, it's great to be here.

Uh, I feel like the turntables have turned. Like, I'm, like, you're, you're right in your, 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, uh, let you, you take us where we should go.

Well, I want to start with stories, probably unsurprisingly. You have a great, uh, I'm not quite sure how recent it was, maybe a year ago, you wrote this like list of observations about how you think and things that feel true to you. Um, and there's a bunch of them that resonated, but one of them was you become the stories you tell about yourself. And so I'd like to start by asking you maybe to reflect on the essential or kind of like dominant stories that have felt true for you over time, um, 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, um, as a, 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 like obvious things that I would say, oh, definitely this. Uh, maybe that's a kind of story in itself that I'm a little—

I think that is, based on some of the—

a little confined myself. Uh, probably the stories I would tell about myself are, you know, a lot of my early life would have been hyper-focused, achievement-oriented, and like outwardly very linear. I was like a very serious student, uh, very perfectionist in that sense. Uh, but with sort of some amount of, uh, 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 I don't know, I think adulthood is in some sense rediscovering the most childlike version of yourself. Um, and so I feel like I'm closer to that than I was 10 years ago, certainly.

Hmm. 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 from your family, is just like obsessed with books and writing and stories. And so I think that's like very authentic to who I was from almost birth. 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 striving, thrusting, you know, phase of, of, uh, you know, early adulthood perhaps. Uh, and then I think you sort of integrate lessons from all of it, but hopefully come back to yourself.

I think that's right. Uh, you've talked about, I think this is a quote, um, but if not, I'm slightly paraphrasing, paraphrasing, the most efficient and enjoyable way to learn is stories.

I do believe that. Yeah.

Which isn't, I don't, I think some people might totally resonate with, other people might be like, stories aren't true or something. Why, why are stories so, maybe, maybe in 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. Of some, like, platonically perfect piece of information. And so this is the best we have. And, uh, 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. Uh, you need founding myths. and those just happen to be like a thousand, you know, maybe I'm even underselling it by many orders of magnitude, so much more durable and magnetic than anything else, you know, we can, we can come up with. So I think it's just a construct of the way our brains work. It's not, you know, an objective reality. It's just a species subjective reality.

That's a fun— yeah. Yeah, it's almost like, uh, We have to resort to this.

Yeah, exactly. This is what our minds want. Um, and so this is the story we have to tell ourselves. Yeah, it's true.

Again, a very open-ended question, but I'm curious if, if you find yourself noticing any patterns in the types of stories you tend to gravitate to.

Yeah, I did actually a funny exercise where I had Claude look across like everything I've written and all of my sort of Readwise highlights, the pieces I've shared, uh, saved, um, and sort of try and think, what are you interested in? Uh, what do you actually seem to gravitate towards? And it was actually, I thought, reasonably, like, resonated with me, which is that there's some axis between, like, madness and greatness that I'm really drawn to. Um, and Yeah, what it takes to be great, the level of sacrifice, uh, and the uncomfortable parts, uh, of these great personalities and sort of that nuance. Um, because I guess I, at some level, I'm just like really 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 really deeply intriguing to me. So something about, yeah, ambition and, uh, and what that takes.

Hmm. Do you, I'm curious, like, do you relate, do you, everyone relates to themself as the hero of their own story. With that comment in mind, like, do you ever find yourself kind of like monitoring your tendency to place yourself as the hero?

Essentially, I think that's like a really deep, interesting question. Uh, and seems like the answer would be yes to me. Like, I I think I, for better or worse, find it very easy to slip into other people's perspective on things.

Ah, cool.

Um, and the good part about that is I can really, you know, almost 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, there's a logic to it. Uh, the, the downside is that sometimes you can think about those things so much that sometimes it maybe takes me an extra beat to listen to myself and like hold firm in the idea that like, no, no, this is also a valid way 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 person's mind and, uh, that's part of the fun, but also yeah, maybe part of the challenge, uh, once the episode ends.

Yeah. I wonder if perhaps that is a common theme amongst storytellers or especially writers, like it's telling that. Obviously, you have some counterexamples, but like, often writers or writers throughout history aren't the, like, grand figures or the heroic figures. You think about somebody like— I don't know, I was thinking a lot about Proust this week because of a couple other 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 there is the hero and then there's the storyteller. Yeah, definitely talking about the hero.

Yeah, and I think I'm, yeah, 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, terrified person.

Right, right.

You don't get that many Hemingways.

That's exactly who I was thinking of. Um, 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 obsessive observation. Uh, I think great writing is often just some version of like very precise writing. Um, and not in the sense that you're going into everything in very granular detail, but you're like observing a feeling or, uh, a experience or an occurrence with such fidelity that you're able to make a comparison that someone else can't. You know, uh, 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, and then for me personally, I like hugely care about just the quality of the words, and that's hard to be too prescriptive about, I think, because I more or less disagree with a lot of Writing advice. Um, and so I, I don't, I don't know if you can really put, 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, 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 right. 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 advice are like not very good writers. And so you get a bunch of—

The 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, also frankly, like the people who gain attention in the modern attention economy are not like literary novelists. 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, bluntness that I think is almost like directly opposed to most good literary writing. So yeah, it tends to just be the case then that the dominant writing advice for people in our rough milieu is like 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, etc., etc. So I don't like that because I think it destroys the 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, I don't, uh, 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, uh, there are worse crimes to commit, but Um, it wouldn't be my, my preference, certainly.

I heard you sort of saying a lot of good storytelling is sort of like seeing what's there. It's not the specific phrasing you use, but there's something to that. I was thinking about and reading about Herzog, Werner Herzog, this, um, 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 military or something. And it's like, he has this part where he closes and opens the door, like, several times. And, like, as this almost, like, OCD tick.

Yeah.

To signal, like, um, he wants to be sure that he can get in and out. And, like, Herzog added it in.

Huh.

Like, the guy doesn't actually do that. Oh, wow. Really? Um. And obviously that's a very specific example, but I do think there are, there's a writer I really like named Benjamin Labatut who wrote When We Cease to Understand the World. He talks about something similar where it's like, um, like fiction is this sort of like shape we give to reality. And so I heard you saying something like that. And I'm curious how you think about like, 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, I'm curious what that tension is between the like very, very precise quote unquote real, um, or the evidence-based or whatever, and the thing that is going to actually tell the story that points you, that, um, that allows you to point at what you feel you have observed is true.

Hmm. Well, I love that Herzog, uh, anecdote. I suppose I fundamentally do agree with the point that there are deeper truths in fiction, uh, than in nonfiction a lot of the time. And that sometimes to explain something with really high fidelity, you almost have to resort to imagination or fiction. I think for something like The Generalist, the only way I feel comfortable doing that is if I'm sort of explicit that this part is, yeah, you know, imagination. And so there are, there are pieces I've written where there is sort of like a, a flight of fancy like that. Like, I think, you know, I'm recalling, uh, a piece on Rocket Internet where, you know, they're at the gates of, uh, St. Peter's Gate or something like that. You know, like, there's, there's those sort of things where I'm okay trying to make some kind of, uh, larger claim, but I wouldn't ever want someone to confuse those things with, oh, this actually happened. Um, because then I think you lose trust in the whole enterprise somehow.

Right. Right. Yeah. And also there's a, there's a sort of central conceit or premise in the container you've created that is promising some level, some baseline, right?

Yeah. At some level, at some point in my life, I hope I'll write a novel about VC and tech and, you know, then I can, uh, talk about truths, uh, that are, you know, through, through that lens. Uh, but still you have a lot of latitude when you write these pieces. Like you can, 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.

Yeah.

So like there's a, there's a fuzziness, but I, but I also hear you on, um, the stakes of like, 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, at least. But I think he's doing a lot of this, which is why I like— again, he's doing something. He's doing a project. Even, I don't know, he's studying humanity or something. Like, he's doing a project that has a different tenor than yours does.

Yeah.

But I do think every writer is doing a little bit of this in some way or another.

Definitely. I'm reminded what's— maybe I won't be able to remember the name of the movie, but it's a documentary by some, by a documentarian who, um, studied the Indonesian genocide. Do you know what I'm talking about?

No, I don't.

Uh, I think there's the second one is called maybe The Look of Silence, but the first one is, um, 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. But in doing so, he makes them reenact these specific scenes, uh, and it's fantastical and not true in some incidences, but in some cases it's like deeply true and is the first time they're really confronting what they've done. So I really admire people who manage to, you know, play with that boundary and, yeah, say something like insanely deep because of it. Um, so I, yeah, I certainly haven't approached anything of that level yet, but, um, I think what you're pointing at is very, yeah, very profound.

I'll find it and link it to it. Um, one other note on this, uh, in your hummingbird piece on, um, Barents.

Yeah, Barents.

Barents.

Yeah.

Um, he's talking about, you're talking about him and you're talking about kind of this like story underneath the story. Um, 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 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. About the way that that influences, like, are those two totally different modes? Are, do you almost have like a skeleton key as the listener because you are a storyteller yourself?

Wow, that's a really interesting observation. I hadn't put that together. Um, 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 5 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, or, you know, I have a little ebook in that sense, or listening to a podcast or watching it like a YouTube. Like my mind is 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 Well, I don't know. Maybe I can, 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, uh, there's something that's always a bit disconcerting with that. Like, yeah, if someone's too clean a narrator of their own story, then it's been polished through use, right? Uh, and then that to me makes you think a ton about what's being delighted.

Um, yeah, it also, it's a, maybe there's a good meta reminder that all stories have layers, um, implicitly or explicitly, um, including the ones, and it's, and it's maybe like you're reading a great, one of your amazing, you're reading, you're writing about Founders Fund or whatever, and you're like, you're seeing the work you're doing about the kind of surface level stuff and the, and the things working underneath, but every story we hear and every story we tell has those, this kind of inner workings. A good reminder.

Yeah, there's a, you know, the sort of, the photographic negative of every story in some sense. Like you have, you know, the story being told and then you have the story not being told.

I want to talk about kind of the different modes of 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, 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. Uh, cliché, but probably cliché 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, I'm, are there any times that you failed badly that you would be willing to share?

Yeah, for sure.

I mean, I, I have a bunch, but at least very memorable or formative ones.

Yeah, I mean, one of the biggest failures for me, which was instructive, was— I don't know, it's not like a super legible failure in some ways, but I studied abroad in Nepal during my junior year of undergrad. And that was like a very formative experience for me because I was hyper isolated. Like, there are a few other people on the program, but Nepal during that period had, I don't know if it's still the case today, but, uh, lots of load shedding. So you had very limited periods of electricity, which meant you had even more limited periods of internet. Uh, and when you did, um, that was, you know, sort of not the best connection anyway. So it was just very hard to sort of leave everyone I knew, uh, be in an environment where maybe the people around me spoke English, but go one degree out, no English, very different environment. And I call it a failure just because I struggled so much. Like, I think I went into it thinking, you know, almost, yeah, 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 this just as magical as anywhere else for me. And I, you know, 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 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 devoting myself to more serious Buddhist study and meditation and, you know, doing Everest Base Camp and these sort of things that are a bit of bucket list-y sort of things. And, you know, it sounds silly, and maybe the lessons I took were in some sense more important, certainly more important, but it was a big failure. And as I reflect on it, like, that one still feels a bit sore.

Perhaps it will come back around as these things, in some strange way, I don't know, these things tend to, um, land in the way, I mean, maybe it's just us narrativizing reverse, but they tend to land in the way that we need.

Yes.

Not the way we intend. Especially things like that.

I think that's right. Yeah, I'm grateful for it in some sense. And, uh, and still, yeah, it still, still bugs you in some sense too.

Hmm. One of the cool things about the amazing, basically, book you published on Founders Fund, uh, is this kind of like overwhelming theme of returning to originality. Obviously, Thiel's kind of core idea is resisting the memetic flow of the world. You, on one hand, I think, have just already like done a lot of different things over the course of your life, whether it be the law stuff and the IR stuff or the fiction and startups and working at the restaurant, like so many different things, so many things probably I don't even know about. Mike Solana at PEC 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 look right at it. I'm curious how you have approached trying to get closer to it. Maybe not as like a, a threshold to cross, but like a continuous gradient. Hmm.

I guess the things that have brought me closest or closer to authenticity are doing things myself and putting myself in positions where there 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, and so actually, you know, Nepal was a good example because that, you know, stripped away actually a lot of the parts.

It's like a distillation, right?

Yeah, yeah, exactly. So maybe that's a, a good, uh, example. But the generalist founding the generalist was like, in many senses, the most authentic, authentic thing I'd done professionally, precisely because it like had that structure of like having to do something 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 I, I work best in those environments. And so, uh, that's a nice story to believe in some sense because it like 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 would relate, is these things that very obviously authentic in reverse, uh, or looking back, maybe for you starting The Generalist or whatever it might be, there is actually like a lot of friction in crossing into that.

Yes.

Have you found that to be the case? Like, has it gotten easier when, when you're adding things now that feel more authentic, or is it always like almost this jiu-jitsu or something?

I think, uh, birth is always painful. I think this is a universal, uh, constant, and starting a newsletter is much less painful than real birth, I imagine. But, um, for As much as I can, uh, 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 okay. Um, I think it was helped by the fact that I had tried on so many of these different costumes at various points that I almost didn't tie my identity too much to it.

I was like, looser.

Yeah, it was like, okay, well, this feels really true, but if it's not, I'll survive.

That's fine.

Yeah, I'll keep figuring it out.

There's another kind of related thread around 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 Packy, you were talking about Founders Fund, but you said when I asked almost everyone at the fund what their big lesson from Peter was, it was that you just have to focus on your comparative, 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 that it would be to find that comparative advantage and then design the game so that you can just do that. Uh, maybe with the previous question in mind and the acknowledgement that it's like maybe a directional gradient and not a threshold, like how, 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. Like, I'm not prosecuting it.

No, I'm not prosecuting it. 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— that 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, huh, wow, someone paused in just this right way. And now I think that's true when it's like there's nothing true 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 like, you know, when I was just getting into the tech world, there were probably founders or venture capitalists who would say something like this, and I would think, gosh, well, 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 These are all such nonsensical things that we use to, to sort of interrogate ourselves. But the person who, who gave you that horrible piece of wisdom, who like put that little software bug in your head, like didn't even think about it for one second if they said it, in my opinion.

Um, I think what's— I want to push slightly, which is my sense is I, I think I tend to agree with you, although my sense is the root, at least how I'm— if I think back to when I'm hearing that, the good part of it in theory is it's like to the person who doesn't quite have the job they want yet, it's about personal standards 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 doing a lot of work.

You're doing a lot of work that's not in there.

Yeah.

Anyway, 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 whatever. This is why, why, you know, people have different interesting opinions on things and maybe that's deeply meaningful to someone, in which case, you know, I'm glad it works for them. I don't know what your question was because my rage clouded me.

Comparative advantage.

Oh, comparative advantage.

Again, I'm sure part of it is the story thing, but like acknowledging that it's your answer in 5 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 higher resolution.

I'm a pretty good writer, and I think that's actually rare. Uh, I think there are not that many people who take writing seriously in the world, uh, 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, uh, throughout my life. Um, and so I think I have the ability to distill information into a story that is at its best moments elegant and true. Um, and then I think particularly with The Generalist, I have the benefit of having a decent grasp of technology and venture. Um, both of these things are infinitely deep, so I don't want to pretend like I'm, you know, uh, it's a comparative, spectacular, 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, uh, that's enough. Um, and then I think the more fundamental pieces— I think I have a pretty good ability to connect disparate threads and like see patterns across different things, uh, where that helps you reveal something that's maybe true or to make a connection more deeply. Um, so something in that, in that zone.

I agree.

Oh, thanks.

To talk about writing a bit, uh, you write about things that are relevant, um, but it's very ground— not just in narrative, very grounded in, um, historical context. Um, at the very least, like the bigger picture. Um, and I think you've talked about like you're, you're not very interested in like news.

Um, yeah.

Like why, and maybe I would add like the technology world, the world you operate in, the VC world, whatever, is like very, not only hyper-present, but like, 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 literature, but like why that's so important to the work you do.

Uh, I guess I, a lot of the sort of 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. Like if someone is writing and doing more of that in-joke-y stuff, it doesn't fit the way my brain really parses this information.

Um, that's another good point is that I think it does the way you do it 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. Um, And then the other piece of it is that sometimes I think when you tell a story in such a, you know, I'm using provincial, not, uh, pejoratively here, but sort of, you know, literally in a more provincial sense, you kind of miss the, 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. Um, and so, yeah, and then there's probably some degree of like ego and bombast where I'm like, just, I like thinking in, in these grander, uh, 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 myself as a, as a journalist. I think of myself as an analyst.

What is the difference between those?

I don't know. I think you could— a journalist would probably say Yes, this is journalism. Um, and maybe the, the argument would be like, oh, by, you know, not taking on that mantle, you're, you know, giving yourself too much of an out, or you're giving yourself too much latitude. But I think I try and adhere to journalistic standards. Uh, but it's true that I've never worked in a newsroom, so I don't, I don't, I'm, I'm intuiting that along the way. Like, I always want to be honest and, you know, conduct deep research and fact-checking and all those sorts of things. But, uh, I am sure someone who's worked at, uh, you know, The Guardian or The New York Times or one of these places would have a different way of processing information. Um, 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 it's also You know, in the connotations of the financial venture, uh, equity analysis world, like more about the investment lens. Right.

Um, and I think that is, but it's typically far less narrative or far less story, like, which is, that's what's interesting to me about the, but I guess I don't find most journalism that narrative. Huh. Interesting.

Like I find a lot of, I don't know, would you call like the Atavist journalism? Sort of. Yeah. But it's, it's really much more like long-form magazine writing, right?

I'm thinking, and you make this comparison, you're like, I'm trying to do kind of like Wall Street analysis in the shape of The New Yorker.

Yeah.

Um, which is a form of journalism kind of, but I hear your point.

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, wouldn't say like, I am a journalist. They'd be like, I write for The New Yorker.

I, 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 relates to you, one of the things I think that is rooted in the question is 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 are writing positively. Yeah, true. And that doesn't mean it's a puff piece. I think people, if they wanted to be super cynical, could call it marketing.

Yep.

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. It's, uh, there is a filter that I'm running most of the time, which is, do I want to write about this thing that I really think is interesting? And, and in some level, like, good, uh, or important. Uh, so there's a positive valence on, like, the topics I pick. Um, 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 in many cases other people have missed. Um, because I, I don't want it to be, uh, a puff piece or marketing, but it is, it's undoubted that there is like that. 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.

Right.

Um, and actually missed much of the exciting stuff happening.

Hmm. Hmm. I think that's right. There's this interesting thing where you always refer to The Generalist. You, you talk about The Generalist, not Mario. You say that, use the pronoun we more than I. Maybe that's just habit or whatever. I'm, 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 like, oh, there are a lot of returns to it being the Mario podcast or the whatever, like the, the, the brands are dead, personalities rule. And yet there's something subtle and maybe in the way you've done it.

Uh, interesting. Well, it's a, it's an interesting linguistic observation. I mean, on, on the one hand, there's like a structural reason for that now, which is that there are 3 of us full-time at The Generalist. Um, so, uh, I run it with my wife. Um, and then we also have a third employee, Kien, who's, who's great. Um, so now that is a very real reality, but I think probably to begin with, I don't know, maybe I was trying to project a greater size than, uh, than it really was, a greater seriousness. Um, that—

Oh, I love that.

I have a founder friend who, he has this old doc on when he started his company and he, he's writing the mission Tim, and it's always, oh yeah, yeah, there's something where you're trying to say like, listen, maybe it is just me, but like, uh, you know, I'm, I'm, I'm staring, I'm swinging for the fences here. Um, and then, you know, 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 Wow. I don't know why. Hmm.

A quote on observation, maybe. You say the finest practitioners of a given craft— or excuse me, of a given discipline— are often the worst at articulating their craft. It's kind of 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?

I think I have a pretty good beginner's mind. Like, I will really, uh, enter something with as much of a childlike openness as I possibly can. And, uh, especially if I think this person might have a secret in some sense.

This relates to what we talked about at the top around sort of like making, reducing your own size a little bit to inhabit. Yeah.

That's right.

Yeah.

Yeah. So maybe it's that. It's sort of that. That willingness to sort of be a little smaller in that space and not come to too many judgments in advance. And also, I find that many people are hidden teachers. If you present as the student, the teacher emerges. And so a little naivety can go a really long way.

Be the dumbest one in the room, ask the question.

Yeah, exactly. And people mostly take 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 obviously obtuse version of it, but there's an element of that.

I mean, also, that's like one of the greatest intelligence-gathering techniques of all time is like elicitation and, you know, sort of saying the wrong thing. So yeah, I don't mind that. I like feel natural in a position of a a student.

You have something about, uh, respecting your process. Uh, if you do your best work at 4 AM with a bowl of candied ginger, do that. Give yourself the latitude to be a difficult artist when necessary. Felt a little bit of peace in reading that, but I'm curious if there are any dysfunctional habits that you've like allowed yourself to just accept.

Yes, of course. I mean, I think, uh, there are many and I cycle through them.

You know, there was a period, this is like But you, like, I guess just to clarify, like, you've a lot— I'm sure we all have dysfunctional habits. I have lots, but I'm not very good at like accept— like, nope, this is just how it is. I have to like— this is gonna be how it's gonna be.

Well, I mean, I suppose some of these things that I write are like things that I'm telling myself. Um, you know, there was a period where, uh, I was writing The Generalist, uh, very early on, and I was, you know, on a weekly cadence, sometimes a couple times a week, uh, I was going, like, as hard as possible, super fast. And for whatever reason, 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—

Like, 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 machine." Okay.

New genre. I've not come across this. That's hilarious.

I almost don't have the stomach to actually actually watch like scary films.

Yeah, I don't either.

But this was sort of 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 literary person. Who would pollute their brain with this nonsense? But I needed it.

High and low. You gotta have high and low.

Yeah, exactly. So, you know, that's a, that was my candy ginger for a period of time.

I like it. Um, you've evolved the Generalist a lot over time. Um, 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, and maybe this is, I don't know how old this is and if it's even still true, but somewhere you, 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, I'm kind of more specifically interested in like specific goals. I had an experience last year where I had two very specific goals in a way that I hadn't in the past, which was to— one was to get to 21 episodes of the podcast before midyear. The other was to run the marathon. Oh, wow. And those are both very like not— there was no like input goal. There was no like— it was just like, these are things I have to— these are hills I have to climb and I can climb them by any means necessary. And so I've been it was an experience of learning the value of very specific ambitious goals. Um, you talk, I think I mentioned this earlier, you like talk about the equity, uh, analysis meets New Yorker thing. Like that's kind of a goal, but more of a vision as well. Like, to what extent, 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 XYZ subscribers, whatever it might be, uh, revenue and, and probably more so like, okay, this year we launched the podcast or this year, you know, we really give this a good effort. Um, I would say I probably think about that a lot less now because on some level I don't. Mind too much if we grow a lot in terms of like top line subscribers. Like there's, it's 160,000 people. I would love more people to come in. That's great.

You're like number 6 on business Substack. Like you're, you've done pretty good on that front.

Yeah, it's, it's good. I mean, it could be many, many times better, but I'm, I'm not, I'm not convinced that having more people is better in that sense. Like I do think there's sort of this trade-off between popularity and influence. Um, and I'm okay sort 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, can I write a piece that footnotes the last best piece I wrote?

Is that just purely a vibes thing? Like, I'll know when I've done it?

Yeah.

Okay.

Yeah, I think so. Um, I think it was—

Good luck beating Founders Fund. That's going to be—

I think I'll beat it this year. I think I will confidently beat it. Uh, but it was clear Founders Fund was definitely the best. Like, uh, there are other pieces maybe I love more or I feel, you know, closer affinity towards, but like, 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. Concession to the present day is necessary. 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 wish, or to be romantic about, or wish that was the case? As someone who's very, been very good at building, like, a modern media company, maybe?

I think, uh, just trusting 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, uh, that was always super tempting to me. Um, and it was why I wrote for 10+ years before starting The Generalist, thinking that, you know, this will— once I do the work, it's just gonna happen. Um, but that's not how things work.

No, no. And it's a blessing and a curse.

Yes.

Blessing as well.

Blessing. Yeah.

Um, many writers, like, find something that works and then they, like, keep hitting the ball. Um, I love Ben Thompson. Like, he's added the podcast, 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 iteration? Given that you've been successful, kind of, throughout.

I think I have to keep it interesting for myself. Uh, I would not be excited to write the same style of piece for the next 20 years. I'm interested in many, many things, and I want to pull down the bigger pieces that I can do as my ability grows. Uh, it feels like in some ways it would be unambitious. I don't mean to cast aspersions on anyone else, like everyone else has their, you know, 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. Uh, why wouldn't I try and do something like much, much bigger, um, and much, much deeper? That's harder. That's more interesting. Like, you need the friction. Without the friction, ooh.

Little meaning.

Yeah. So, so I'm, I think it's a reflection of the fact that I, I'm trying to learn a bunch of different things and, and hopefully the, the Generalist is enough of a vessel to support that, um, and enough of a vessel to support it as my ambition grows and, um, I want to try and go bigger and bigger.

Have you kept anything constant? Is there anything you're kind of— that's sacred?

Yeah, the writing. Like, I, I think there would be a version of The Generalist that I haven't been able to get behind where I had like many more writers, um, or where I aggressively at this point used AI to write drafts and like, you know, it's close enough in some senses. Like, I think the sacred part is just really caring about 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 cliché, like, find the thing you don't want to automate. My, um, I love David Senra talks about this and he's like, why don't people be like, why don't you have someone read the books for you? Boundaries. And he's like, that's the whole point.

That's why I'm doing this. That's what I like doing.

You also have changed a bunch and explored a bunch of different business models and like variations of business models. 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 make it free. Sponsorship is a much better business model.

Yep.

Um, I think you also had like a core part, at least around then, like a core part of the subscription was actually about this community piece of it.

Yep.

Um, a lot of sponsorship as well. Then Generalist Capital, obviously now Hummingbird. Like, 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, why the paid subscription actually makes sense, especially for someone of your scale. And then more broadly, like, reflections on kind of navigating the business model side of, of all this and why you've kind of landed where you have, even including monetizing it via investing.

Yeah, I think there have been different 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 it's probably not an accident that every media company eventually sort of, like, tends to converge on doing both. Um, 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, like, on balance probably makes sense. Um, 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, uh, like the, the value of what you're giving people just hopefully keeps compounding if the things are evergreen in some, some sense. Um, so in some sense they reflect the maturity of the business, but, um, the things that really didn't work were, were the community, um, and having that as a big part of the subscription and not because, you know, there are 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, it's really hard to do that, I think.

Well, it requires a lot of like tending, like gardening. Yeah.

And it's just like not my strength.

Yeah.

And also we have such a various audience that it's not clear what people are sort of joining for. Um, so yeah.

What about investing? Why, like, when did that first show up? I mean, you, I'm trying to remember, did you, had you done any investing prior to The Generalist?

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 Generalist has the lens it does, um, was, was coming into it with that. That mindset. And I sort of never properly stopped investing. There was maybe like a year where I didn't 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, you know, past the stage of survival.

Yeah, yeah.

Then it was exciting for me to be able to do that more seriously with, with Generalist Capital.

And why? Why, we'll talk more about Hummingbird, but why was it Generalist Capital and not like plugging into a kind of bigger entity, at least back then?

Hmm. 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 much more progress than I'd ever made in my professional life and felt much more myself. So, uh, 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 the like it's all up to me.

Yeah, there is. Yeah. Yeah. So I, you know, I wanted to do it.

Yeah. 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. How is energy underrated? Maybe specifically in this context?

Well, I think a lot of people come into conversations more wishy-washy or maybe for good reasons, sort of more default skeptical. And you definitely need that as an investor. But there is a point at which, 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. And I find that it is extremely powerful. If you can be the truest believer authentically, that's like, that's really attractive to people in any walk of life. But, but with founders, certainly.

Like, there's one reading of this is just like, be warmer and like more excitable. The last bit you mentioned doing it authentically, like how even in terms of the energy you have to give, like some conversations are very energizing and it's easy to have energy run off and other conversations aren't. Like, like, do you have any relationship to— I don't know, I don't want to say faking it because that's— I think that's actually definitely wrong. But how that— like, how can you— how can you bring energy to the table consistently in a way that isn't contrived?

I guess I, I think of it, you know, you have to perform and not like an actor performs, but like an athlete performs, you know, like you. Yeah. When, 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, you have to just be ready for it. And that is a part of showing up. Absolutely. Yeah. If you're, if you're serious about wanting to be an investor and you see a great opportunity and you can't rise for that occasion because you're not feeling great or I don't know, the other person's not giving you much, like that's your responsibility.

Yes. 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 talked about every second counts. And he, he related to it that way, which is like, this 8 AM Zoom meeting I have, like, might be the most important meeting of somebody's month.

Yes.

And like, I have to show up for that.

And it might be the most important meeting of your life.

Yes.

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 the day— I talked to Andrew Reid 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, which I'm— my assumption would be that you've had at least some amount of, or at least being close to that. Like, what is so special about that relationship?

I'd always heard that from other VCs where they were like, you know, the reason I was able to double, triple down into this winning company 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. Uh, but I really do think there's something, something special there about being the first believer. And it's sort of the same thing as, you know, I think Tyler Cowen has written about, um, you know, 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, um, just raising the ceiling for someone. And so I think there's something to that of just being the first person to say like, I actually see your talent and believe in you and I think this can be massive, um, is very memorable.

Yeah, I've talked with people more on the kind of like grants side of things, although I think it, there's actually some overlap with early stage investing, which is like sometimes the— that conviction is 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, you're, you're the sort of 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.

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 the more convoluted your investment rationale is, the more skeptical you should be of it. I've heard this pattern across certainly not just venture capital as well from different very successful people. Can you either give an example or reflect on like the people you know who are very, very good at this or the ways you even become like, yeah, what is that? Like it's, it's a really cool like line to hear. And like, I think 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, it's not the same exact idea, but it's like if a rationale can't be distilled onto a note card, then like you probably haven't, don't have enough clarity.

Yeah. I think for investing, there's often, you know, so much skepticism around venture, which part of it is earned, where, you know, people will be like, oh, the average VC, you know, their, their rationale for something would be on a napkin or, you know, that's actually good. That's really good.

By the way, I know of very serious investors who are not VCs that have the same kind of mental framework around 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. You're like, insanely good? Like, what? But why? Like, you know, come on, help me out here. And I think what you've come to, come to realize is, one, the best practitioners are not always great great at articulating their craft. 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. It's just, this person is special. Um, and that's infuriating, I think, in some level.

It's 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 means something very actually quite specific. Yeah. And so yeah, to me, those are many of the best articulations of why great people invest in a company, even if it doesn't, you know, give you exactly what you want.

A couple things on the, on the, on the maybe Founders Fund, Thiel front. Um, there's this thing where you say, I can't remember if it was in the piece or in a podcast, you frame it sort of like Michael Moritz is like, orientation is like do right. And Thiel 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?

Oh, interesting.

Yeah, 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'm probably not axiomatic about either case, but I would imagine I lean more moritz, like I, 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, not in a legal sense, but in a sort of, uh, philosophical sense, need to learn when you're breaking the rules, um, cleverly.

Well, and there's a tinge of it too around like, see the world as it actually is.

Yeah, that's right. That's right.

You also observe that Thiel is, I think you frame it as unusually creative at hanging on to talent. Maybe in a broader sense, do you have a, why do you think great talent hangs around? Whether it be with Thiel or otherwise.

Well, Thiel is so smart in the sense that he's built like the Peter Thiel cinematic universe of different entities. Um, and so, Rube Goldberg, you're just falling through the labyrinth —of— yeah, exactly, of Lord of the Rings names. 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, right? And different, you know, scales of companies, etc., etc., that I think he has, yeah, a lot of cards at his disposal that he can sort of make it easy for someone to find their next big thing. Um, you know, in terms of retaining talent more generally, in some sense I'm like very much just learning that from other people, but it feels, uh, like people are always sort of maximizing some version of a few things of, you know, 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, at least with teal, but maybe in that the second thing too, is one of the things that really compounds and is really hard to start anew with is trust. Yeah. And so if you can manage those other things you said, you get to stay in the field of trust, especially for teal, that really compounds. You think about any of us for any of our relationships, I think when you're in year 8 with somebody, 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, such that I think if he says, you should go do this thing, you're like, I don't know, I think I probably should.

You see, yeah, you see something I don't see. Yeah. He tends to be right about these things.

Yes, exactly.

I know you are generally —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. Uh, 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 raw edges of 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, people seem to have their own ways of, of making that happen. And, you know, Barend, I think, has a very unique genius of, like, creating that environment for people, sometimes almost out of nothing, instantaneously. You know, there's a, there's a, yeah, a sort of divine genesis that he can just—

Yeah, a jiu-jitsu move or something. It's pretty remarkable.

Farhad, you know, the other, um, you know, the managing partner at Humblebird has his own way that again is like 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. Uh, you know, you're, 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 think, um, most investors that I've seen at least, or I don't want to say most, certainly many, uh, almost haven't oriented themselves to to do that. They're almost more information gatherers. Yes. Yes. And I think that serves them well in lots of, you know, in lots of environments, in lots of places. But Hummingbird does something very different. 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. And so that, that just like speaks to me and makes sense to me in some way.

Yeah, what's interesting about that is I have some challenge in what I do, but I also have no quote unquote ulterior motive. Like, in theory, my job is just to make— maybe if you wanted to be more cynical, just make the best content. And really what I think my goal is, is like make the person shine in a way that I see them or whatever. Whereas what they're doing or what you're doing now is, 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 like, I'm sure performance, but also it goes maybe back to the story underneath the story.

Yeah, there are, you know, there's always the game and the metagame. Yeah. And yeah, I think personally, I think that's happening 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, or in some way, it doesn't always have to be, you know, it sounds so cynical. I don't it has to be. 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, 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? How important is Maybe I'll backdrop it. We both know Anjan Khata well, who runs Daylight, and Anjan is like a remarkably idealistic founder, like deeply mission-driven. And there are personal motivations inside of that mission. But like, it's— yeah, it's idealistic. So my question is like, how important is the like why in the like almost external sense of the mission versus the like quality of ambition and like the fuel around like the person's, I don't know, um, I need, I have something to prove or something. Like, does that delineation make sense? Maybe I'm forcing it, but I'm, they're like two different kinds of motivations maybe?

Yeah, I think you have to have the second one. Um, I 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, 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 an idea that Baron talks about that reminds me of— I've heard other investors talk about— Chris Peck frames it as like, are they post-death? Barnes says, or this is you writing about him, how had it changed them? What residue had it left on their selves, their souls, their lives? In particular, he, Barnes, 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. Like, how do you think— I assume you're familiar with the kind of like good fuel versus bad fuel frame? No. What is that? Sort of like, Bad fuel would be like, there's like a remarkable— Patrick O'Shaughnessy will talk about like, there's a remarkable number of really successful people whose like dad died when they were 14. Ah, yeah. Um, uh, or just like some kind of self-punishing. And good fuel, I think, can be very internal. It can be this artistic kind of authentic. Um, but it could also be like, I need maybe the idealistic thing we were talking about earlier. It sounds like maybe, maybe I'm answering my own question, but like, it sounds like you're kind of saying The importance is that there's fuel at all, like some kind of rich fuel.

But like, I, I guess I need to read more about it, but I'm sort of skeptical about the idea of good fuel. Ah, like I, maybe that's too cynical, but what, what's an example of truly good fuel?

I think the, um, tip, like I would say someone like Rick Rubin, uh-huh, is presents as somebody who's just like doing it for the love of the game. There was this whole thing recently about Alyssa Liu, the, um, 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 2 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. I'm sure she also had to grind. Yeah. But like, 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 singers, people become more successful over time, in theory, at the very least, people tend to like shift from bad fuel to good fuel. I see. Something that like allows you to go farther, longer, so on.

Okay, I could, 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 and then maybe to, you know, create some, some different level. Yeah, you find new sources of energy and things like that, but I don't think you become the person who is able to manifest this good fuel without the overbearing dad story. Like, 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 are founders you talk to who say, 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— have you ever seen the documentary series 100 100-foot wave? No. Okay, it's about— it's so good. It's about these guys who are trying to surf.

And I've heard Hamilton-type guys.

Yeah, like the newer generation, older generation. They're going to Nazaré in Portugal trying to surf these monster waves that, you know, if you fall, you're like falling, 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, who's this old sort of grizzled surfer And, you know, his wife's like, yeah, he always says he had this great childhood and that he had 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. 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, came from a very, very, very well-adjusted background. Yeah. Yeah.

There's a, 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, um, that's, 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, again, maybe it comes back to like seeing things as they are, which is like, what does it take? It takes everything.

Yeah, it takes everything. And, you know, even when you look at these stories, sometimes maybe they look like they, you know, they had a lovely childhood, but because of the way this person's mind works, it was torture. You know, there are different, different ways that people perceive the same set of circumstances. Um, so anyway, uh, yeah, I think, I think it takes everything is the right way to put it.

There's a bit at the end of that hummingbird piece where you're talking about messiness and in the same theme. Um, 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 as it is. 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. Wanderbrand and Ilary can generate a return by capitalizing the unreasonable, because innovation is unreasonable, because progress is messy. We scrabble with fingernails and fingernails full of mud. We pound our bodies bloody against a barrier to see what lies beyond. We lurch forward strangely and without logic. We rely on those we do not like, and still we should feel grateful for them. This is the world as it is. Beautiful writing. Thank you. I think my question would be, this almost feels a little bit at odds with your, like, obsession with stories. And I don't— clearly it isn't, but this, like, radical obsession with what is, like, truly, grittily real without any of the— even when you're talking to Bahrendt, he's like, doesn't want to tell stories about himself because he's like, so, like— and yet you're someone who is without losing any rigor or even necessarily what is true, a lot of your writing has a poetic nature to it. Like, do you see what I'm getting at? Like, there is— 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 were— you have just joined this firm that is so radically obsessed with this.

Mm-hmm. I guess I think that stories are really true, or the best stories are the, you know, the one that is sort of truest in some sense, and not in the purely rigorous factual way, but in the Herzogian way. Yeah, yeah, yeah. And yeah, I think the same is true of poetry, right? Poetry is sometimes just so acute that it says something much more truly than dispassionate facts could. And so that's maybe the the place where those two things meet in some sense.

I like that answer. There's a, just a short bit where you were, you had met with Gort at 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 What did that mean? After 3 or more of these burrowing questions, you begin to realize what you really think and how deeply that thinking goes. I'm probably projecting a little, or I'm expanding it out to maybe the broader Hummingbird kind of world, but I'm curious how you and now your new— newish team, how like that vibe or that tenor or that maybe even specific way of doing things comes up in the daily work, in the work with the founders, in, in how you even challenge each other.

It definitely comes up, I think, in how we challenge each other. Like, you know, uh, we'll talk a lot about a meeting we had with the founder and, okay, he said this thing, like, 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 I actually totally parsed that in a very different way than, than that. So, you know, I think earlier in the piece, uh, Salar, the CEO of Monumental, talks about Barend being like the most linguistic VC. I was going to bring it up.

Um, uh, and obviously I think I would compare you in some way.

Yeah, I mean, uh, hopefully I'm, I'm linguistic. I have to prove that I'm, you know, I have a long way to be at Barend's level from an investor perspective. Um, but yeah, there's an obsession with words, language down to like an insanely granular level. I can't, I can't overstate that honestly.

Maybe it relates to your earlier point about stories and like how much context, how much is held, how much resolution is held within them. Yes. Um, one reading would be that like overly focusing on words is like missing the forest through the trees. But the other reading, it's telling that they also compare it, they compare Barndt 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, like, far more 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, you know, in, as a, if he was a therapist or a, you know, a psychological profiler, he would be elite. And same for, for Farhad. Like, there They're, they're just hyper observant about everything and words just happen to be like a big part of that.

You, a couple months ago now, joined them full time, maybe longer. Um, and you wrote about this at the end in that piece. You said, for 6 years I had built The Generalist on the conviction that I am only truly myself inside of a 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 were had been met with an automatic refusal. But in this instance, for the first time, a refusal did not instinctively arrive. Intuitively, I sensed that 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. Like, what were the I'd love to hear you talk about like the emotions going into that decision. Maybe the things, I mean, time will tell, but the things lost, the things gained, maybe the ways you noticing yourself sharpening even already.

My ability to observe and ask questions has definitely like, I think, uh, 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, you know, look back on a conversation and think, how did they, how did that actually happen? Or, you know, all these sorts of things. So that to me has been, yeah, like a real gift and something I've loved so much about that period. You know, I think the feeling I have so far, and it's, you know, 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 really sensed I fit in. And we had sort of like the same ability to connect at this, like, very high fidelity beyond maybe your very old friends or your spouse or your partner. 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, you know, keeps it sharp and, you know, allows you to spar well. So Um, the experience with joining Hummingbird was really almost, uh, this massive intuitive pull, even as like some set of rules I had almost set for myself, uh, held me back at first of like, no, no, no, but don't forget, you're only good if you do your own thing. Um, and at some point I think I learned to, to let go of that.

You seem to have, this maybe relates a little to the evolving the generalist, like you do seem to have a healthy relationship with your own kind of structure. And maybe this was a pretty rigid one, but like you seem to be pretty good at allowing them to serve you and then like being able to drop them or evolve them as, as things change.

Yeah, I think, uh, someone shared the, the saying, uh, sometimes you have to know when to kill something before it kills you. And I think there's something really true about that. Um, and I'm, I may be particularly minded towards that. I, I'm okay killing off things early.

Yeah. 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. Maybe it wasn't quite like that for this decision, but I am curious about like how much of an actual, like, will I, won't I decision it was, um, where you really had to sit and weigh the rationale, or it was sort of just something that quickly became kind of, or maybe not quickly, but eventually became 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 commit. Um, and I think you have to be willing in some sense to 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 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. Right? And so it was really more about me, me checking that. Hmm.

Is there anything you think you've lost? Or maybe a better way of asking the question is like, is there anything you feel like you really had to give up?

Yeah, of course. I mean, you, you give up total control of your schedule, right? Like, there, there's a, a level of control that I get to have just when the generalist is, you know, my thing where If I don't want to do any meetings for a week, uh, that's totally fine.

By the way, this firm, apparently people are meeting 30 companies a week.

Yeah, sometimes. Insane. Yeah. Um, not me, but people on the team are.

Um, I was like, there's no way these pieces are getting written.

No. Um, I mean, frankly, Hummingbird is like insanely anti-structure. So I think if I was sort of like, hey, you know, I, I need time to work on something, there would would, 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, you know, not be the bottleneck in anything. Or, uh, and so there's just a different level of consideration that you have to have in the same way that, you know, when you're, uh, 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, uh, wrangling and, and planning you have to do to accommodate other, other people's needs. Yeah. Yeah.

We match, we, we, um, we meet the intensity required.

Yeah, exactly. Uh, and for the most part, I feel like that's been not something lost, but like something that has been actually really good for me.

Yeah. Yeah. Uh, one other maxim. You say picking a career your 7-year-old self would find exciting is a pretty good heuristic. You know yourself better at 7 than at 22. How does your current work or your current life fit maybe what 7-year-old Mario would have aspired to?

Well, I think 7-year-old Mario loved writing and books and also then went through a sharp turn maybe around 8 or 9 into wanting to be a trader in the stock market. No way. So, so there's some good—

there we go. Good threads there. Easy plug. Um, you also talked about, um, you're talking to somebody and you're saying like one of the most generous things you can do for somebody is to push them like well beyond what they're expecting of themselves. You alluded to this earlier too. You've talked about scaling your own kind of expectation of yourself. Um, this relates to like maybe the conversation about like being able to drop things or so on. Like, how do you, how do you almost like build rhythm or systematize or something like build, um, consistency of like continuing to raise the bar or like widen the aperture?

I think the secret is being a very, uh, dissatisfied person. Is having deep psychological issues. Uh, no, I mean, I'm sort of joking, but there is something where I'm just congenitally dissatisfied with the state of things. Um, and that's, you know, the, the thing that that, you know, 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, like something doesn't seep down to the bedrock. I'll invert it then.

What are you most, or what have you been maybe at different stages, like other things that you have been most proud of?

There are a few minutes after a piece I've written goes out that I feel sincerely proud, um, and that almost immediately transmutes into anxiety and, uh, expectation. But yeah, sometimes that can like last more or less time. Um, there are sentences which I'll read sometimes and still think, hey, that was a good one. Um, so some of the ones you've read, I think when I hear you read that, I think, oh, that was good.

I like that. I hope I haven't stumbled over them too poorly, but— No, no.

And then there's some you read and I think, I got to get back in there. Like, I want to change that. Um, so— Can't do that. Can't do that. Honestly, a good string of words makes me proud at times.

Yeah. As it should. Um, I have a handful of kind of miscellaneous things before we wrap up. Um, first of all, you, and I would encourage people to read, I think it was in your 2026, it's almost unexpected. It's like your list productivity stack or something. Yeah, it is unexpected. You have this just amazing— you talk about how you use Claude basically in all of these amazing ways. 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. As well as like using it as this really robust 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. Um, I think my question is a little higher level, which is just like, you have maybe, it's actually what we were just talking about, but you have this seeming level of like a deep level of intellectual humility, um, in the way you show up, in the way you, and I'm sure part of that is what makes a good writer and a good investor and so on, but how do you, is that something you aim to, to, to develop or maintain?

I mean, I hope I don't lose it. A little bit. Um, I think it's mostly true. I think there are probably things where, uh, I'm sure someone, uh, in my life would be like, actually Mario is like an egomaniac about this. Uh, you know, we all have our flights of fancy, but, um, no, I mean, one of the things that I think you learn studying great founders, uh, reading great books is like, wow, I'm, I'm barely scratching the surface here, right? Uh, of what ambition means, uh, of what greatness means, of what doing great work means. So, um, yeah, I wouldn't, I wouldn't want to foreclose my ability 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 about Genghis Khan, I don't know enough about Genghis Khan, and I don't have really time to read about Genghis Khan, but like, there is, uh, there are a lot of ways to learn. One maybe element of this actually is like, You, you have, let me see. Uh, oh yeah. Claude created a pedagogical approach to teaching Mario. Yeah. Like Markdown Dog. Yeah. How do you make yourself more teachable?

Hmm. Well, the great thing about these AI systems is it has to figure out how to teach me. I don't have to make myself that much more teachable.

Most people aren't. There's some, like, again, part of this is just like, 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.

Hmm. Maybe. I guess I'm, 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, um, you know, why are you in, you know, sometimes it will index on a set of questions where I'm like, these are actually not deep questions what you're asking. Um, and so you can sort of take on the role of the precocious student who is questioning the teacher a bit.

Versus like Churn, ah, this isn't that good, I'm going to Yeah, yeah, because it can get better.

Uh, and also, 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 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, and there's productive sort of conversation there. Uh, 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 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 things that stood out. One is your, uh, there's this huge section on status and playing, like learning to play status. You say one, one bit stood out. A CEO who wants employees to brainstorm creatively will have much better luck if they lower their status rather than raising that 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?

Hmm. As a writer, that's really interesting and I haven't thought about it too much.

Uh, yeah, maybe investor is a little more intuitive.

Yeah. As a writer, probably I'm playing high status a lot of the time. Well, there's sort of something almost default high status. Status in saying everyone should read this. Um, but hopefully there are times where I can play low status and write.

Also, I would imagine in the, something like Founders Fund, like you are, or really any of the entrepreneurs you work with, the inputs maybe are more low status.

Yeah, 100%. Yeah, yeah, definitely. Uh, and then you are sort of hopefully emerging as at least some kind of authority. Yeah, yeah. Uh, otherwise, why are you, why are you sharing it? Um, there are obviously styles of writing where you can play low status, like comedy writing. You could, you could certainly play low status. Investing, I think I'm definitely always interested in what the person is, is playing, uh, and how fast they can, can flip. Uh, you know, are they a status expert, as Johnstone would say, where they can play low status if it suits the situation and high status, uh, at another moment.

He also talks about unlearning, and I'm curious if anything immediately comes to mind as things you've had to unlearn.

Learn. Yeah, I mean, I think, oh, so much we have to unlearn, right? Like our— I don't know if you— this resonates, but I don't know, most advice you're given growing up as a kid from like authority figures is mostly not good. Like, I actually think the advice my, my parents gave me was really good, but teachers, things like that, like, you know, uh, you learn to, to set in your mind like a very specific set of options that are, the reality is there's much more available to you.

Certainly. Maybe, maybe, um, have there been any things that have been particularly hard to unlearn? Hmm. Hard to let go of almost?

I think there's something about learning to let people meet you halfway on things. Um, 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. Um, pragmatically, but more sort of spiritually, philosophically. Um, so that's something I, I, I'm still unlearning.

I don't know that these are at odds, but you also write about, like, you have lots of great advice about, like, being good at asking or getting, being good at helping people, like, allowing people to help you. Yeah. Which which 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, 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 you can learn to maybe hold that ground a little bit more.

Holding your ground is a good, is a good mental thing to hold on to. Um, you also, I love this, this is just kind of out of pocket, but you said, uh, most products people contend have taste show no sign of true deep quality. Yes. 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. Yeah. What, and I think you, if people want examples, you do a, you list all the things you use, but what, what is a sign of true deep quality in a product?

Generosity, uh, sort of meeting the user where they are. And I think that's actually true of writing as well. Uh, uh, there's a lot of writing that almost assumes a huge amount of knowledge. Uh, and you have to calibrate it, you know, for your audience. So, you know, 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, uh, 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. But, um, I, I. Yeah, I think there's, there's more to be done in that.

Even those last two things you said Silicon Valley like claims to be obsessed with.

Perhaps this is your point, but like, yeah, I don't, I don't, uh, 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, I do think there are, you know, 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 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 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, I'd want to tie myself to too much. Yeah.

You wrote that you are— spent nearly a year studying what may be one of the most important companies of our era. Hmm. Curious if you can give us any kind of teaser for what that might be. Oh, it's okay if, 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, are changing the technology industry, uh, and playing major roles in the way that great power conflict is, is being waged. And so, uh, hopefully I can write a piece that captures one of those companies at a really deep level of fidelity.

Are you still working on the novel? Yeah. Yeah. As if there were not enough things.

How's that going? Uh, how is it going? It's going quite well compared to a year ago. Okay. Um, I started working with, um, a really incredible editor, uh, who is like one of the most acute readers I've ever met, um, and who has been able to diagnose some of the things that I've felt were wrong with it but couldn't put my finger on enough. Um, and so I've really learned like a huge amount about that. Uh, yeah, about like structuring things, um, and why certain things work and certain things don't that, um, I was missing before. Right. So I actually feel I'm the closest I've ever been to getting a version that, that I'll be happy with. But I'm also very aware that my time is sparser than it's ever been. Yeah. And so I'm kind of— that's the part where I, I feel a bit upset about or a bit stressed about where I'm like, I, I can now kind of see how to get there for the first time. Time, but I need, it's, you know, it's not going to magically happen. So, uh, who knows how long it will take.

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 maybe to flip that for you, which is if there's anything that comes to mind that you're most glad you did.

I mean, the, the most obvious one is go to my best friend's, uh, or one of my best friend's birthday parties and meet my wife. That one's certainly the best thing I ever did. 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, at NYU while I was working at a law firm for fiction writing and begin as a 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, uh, 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, um, becoming the person you imagine yourself to be.

Yeah. Yeah, exactly.

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. That's a wildly opinionated and probably a banger. How does your wife make you better?

I almost disagree with the premise. Like, I don't I don't, she makes me better in many ways, but like, why? That's too focused on me. You know, she's just incredible in every way and not because she does something that like changes my chemistry. Um, 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 just, yeah, so, so obvious and so effortless. Um, so I'm very lucky in that sense. So she makes me better, but, uh, but yeah, she's just miraculous in her own sense.

I have one, one last thing, um, a pair of quotes, I suppose. This is you first. Uh, over the course of my career, I've 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, once I'd begun, it was strange that it had taken me so 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 from Oscar Wilde, who I think Bharat, um, brought up with you in that, um, 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. And that is your reward. How is this reward of not knowing, of being maybe a generalist, we could say, how's that going?

No complaints so far. Uh, I think, 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. But I try not to get too attached to the certain form factor. So, you know, I hope I surprise myself in a few ways. Yeah, in the years ahead onwards.

Well, thank you very much. That's all I got. Thank you. As a reminder, you can find all notes, transcripts, and links at dialectic.fm, and in this case, slash Mario-Gabriele. 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 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 5 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.