43: Mario Gabriele - Reality is Story-Shaped

26:01But 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. Um, and maybe the lessons I took were in some sense more important, certainly more important. Um, but it was a big failure. And as, as I, as I reflect on it, like that one still feels a bit sore.

26:43Mario Gabriele:Hmm. 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 a narrativizing reverse, but they tend to land in the way that we need. Yes. Not the way we intend. Yes. Especially things like that. I think that's right. Yeah. I'm grateful for it in some sense and, uh, and still, yeah, it's 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 teal's kind of core ideas 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 um mike's a lot in that piece he says the way to escape competition is through authenticity and you talk a lot about this kind of finding your own specific game.

27:50Mario Gabriele: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. 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. Um, 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. That's so good. Yes. I think you either like rise to that or you don't.

28:39And so actually, you know, Nepal was a good example because that, you know, stripped away actually a lot of the artists. It's like a exactly. So maybe that's a good example, but the generalist founding, the generalist was like, in many senses, the most authentic, authentic thing I had 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, cause it like makes you predisposed to take on more of those risks.

29:20But I think there is truth to it.

29:21Mario Gabriele:At least my experience. And I think other people 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 was actually like a lot of friction and crossing into that. Yes. Is, have you found that to be the case? Like, Has it gotten easier when you're adding things now that feel more authentic? Or is it always like almost this jujitsu or something? I think birth is always painful. I think this is a universal constant. And starting a newsletter is much less painful than real birth, I imagine. But for as much as I can, 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.

30:07You 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.

30:22Mario Gabriele:Uh, it 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. Um, there's a, another kind of related thread around maybe like not being well-rounded. Um, two quotes I liked first, um, how you do anything is how you do everything is a, is a perfect encapsulation of what is not true. Brilliance is context dependent. Energy is context dependent. Insight is context dependent. See, uh, Steve Jobs, pathetic job application. And then in your conversation with Paki, uh, 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 advantage at the expense of everything else.

31:10Mario Gabriele:And that's another way of saying that in a sense. And so if I was to take one lesson from the piece as a fund manager, it would be to find that comparative advantage and then design the game so that you can just do that. Maybe with the previous question in mind and 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, how you do anything is how you do everything. It really like, even hearing you say it, I find it so, so stupid.

31:48Like it's so incorrect, obviously, but it sounds like something that has the rough shape of wisdom. And so people

31:55Mario Gabriele: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, 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.

32:32Um, and there was a period in my life where I would hear someone say that, especially as an authority figure, perhaps like, you know, when I was just getting into the tech world, there were probably 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

32:48Mario Gabriele: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 sort of interrogate ourselves. But the person 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. I want to push slightly, which is my sense is, I tend to agree with you.

33:24Although 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.

33:35Mario Gabriele:It's about personal standards and integrity. 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. Look, I look forward to someone coming out with a good defense. Yeah, yeah, yeah, we welcome it. 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 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.

34:10I don't know what your question was because my rage clouded me.

34:14Mario Gabriele: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 five years is going to be different. Like the direction of travel on that, like the comparative advantage and particularly like how you've started to dial it in, like see a little bit higher resolution. I'm a pretty good writer. And I think that's actually rare. I think there are not that many people who take writing seriously in the world as a as an activity. and then there are fewer people who really put in a ton of hours to get good at it and I definitely did that throughout my life and so I think I have the ability to distill information into a story that is at its best moments elegant and true and then I think particularly with the generalist.

35:06I have the benefit of having a decent grasp of technology and venture. Both of these things are infinitely deep, so I don't want to pretend like I'm, you know, 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, that's enough. 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 where that helps you reveal something that's maybe true or to make a connection more deeply. So something in that zone. I agree.

35:54Oh, 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

36:10Mario Gabriele: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 BC 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 in 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.

36:48Like if someone is writing and doing more of that in jokey stuff, it doesn't fit the way my brain really parses this information.

36:58Mario Gabriele: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. 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 pejoratively here, but sort of, you know, literally in a more provincial sense, you kind of miss 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.

37:41We actually understand what this might mean or what this might do. And so, yeah, and then there's probably some degree of like ego and bombast where I'm like, just I like thinking in these grander settings. And that's also can be a weakness where, you know, you imagine every new feature is like, you know, uh, some part of the Roman empire or the Mongol horde. And it's like, you know, well, let's, let's dial it back.

38:09Mario Gabriele:Hmm. Is what you do journalism? Uh, no, I don't think so. Uh, I think I've never perceived myself as a, as a journalist. I think of myself as an analyst. Um, what is the difference between those? I don't know. I think you could, a journalist would probably say, yes, this is journalism. Um, 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.

38:50Like I always want to be honest and, you know, conduct deep research and fact checking and all those sorts of things. But I am sure someone who's worked at The Guardian or The New York Times or one of these places would have a different way of processing information. But an analyst to me is still fundamentally doing some of that fact-based work, but is happier taking a bit more of an opinion, a bit more of a stance. and it's also, you know, in the connotations of the financial venture, equity analysis world, like more about the investment lens. Right. And I think that is...

39:30Mario Gabriele:But it's typically far less narrative or far less story, like which that's what's interesting to me about the... But I guess I don't find most journalism that narrative. Interesting. Like I find a lot of, I don't know, Would you call like the atavist journalism? Sort of, yeah. But 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. 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.

40:06They'd be like, I write for the New Yorker.

40:08Mario Gabriele:I'm partially asking people, I've met a few people over the last year that I've been doing the podcasts and people ask me or have asserted that I am a journalist. They've asked me if I'm a journalist. And one of the things that I feel that I think relates to you, one of the things that is rooted in the question that is both true for analysts and journalists is there's a tremendous amount of rigor, which is rare in this world, in the world that you do. But it's next to this thing that I relate to, which is you overwhelmingly are writing positively. Yeah, true. And that doesn't mean it's a puff piece.

40:41Mario Gabriele:I think people, if they wanted to be super cynical, could call it marketing. Some of that's about incentives, but it's this interesting combination of tremendous rigor, the rigor, quote unquote, of a newsroom, but framed in this like, I want to tell you about why this might be great. Yes, it's true. There is a filter that I'm running most of the time, which is, do I want to write about this thing that I really think is interesting? 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.

41:29Um, because I, I don't want it to be a puff piece or marketing, but it's undoubted that there is like that feeling. And almost that's axiomatic because part of the generalist was a response to the sense that all tech coverage was like hyper negative and actually missed much of the exciting stuff happening. I think that's right.

41:54Mario Gabriele: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 a 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 like oh there are a lot of returns to it being the mario podcast or the whatever like the the brands are dead personalities rule and yet there's something subtle and maybe in the way you've done it? Interesting. Well, it's an interesting linguistic observation.

42:32I mean, on the one hand, there's like a structural reason for that now, which is that there are three of us full time at the generalist. So I run it with my wife. And then we also have a third employee, Kian, who's great. So now that is a very real reality. But I think probably to begin with, I don't know, maybe I was trying to project a greater size than it really was, a greater seriousness.

42:58Mario Gabriele:Oh, I love that. I have a founder friend who has this old doc when he started his company, and he's writing the mission statement. It's always. Oh, yeah? It's just him? Yeah, there's something where you're trying to say, like, listen, maybe it is just me, but, like, you know, I'm staring, I'm swinging for the fences here. 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, I don't know why. 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.

43:42Mario Gabriele: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 um 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 a secret in some sense relates to what we talked about at the top around sort of like making reducing your own size a little bit yeah didn't have it yeah right yeah yeah so maybe it's that it's sort of that uh that willingness to sort of be a little smaller in that space um 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 The teacher emerges.

44:44And so a little naivety can go a really long way.

44:48Mario Gabriele:It'd 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. It's insane. elicitation and, you know, sort of, um, saying the wrong thing. So yeah, I, I don't, I don't mind that. I like feel natural in a position of a, a student. You have something about, uh, respecting your process.

45:23Mario Gabriele:Uh, if you do your best work at 4am with a bowl of candy 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 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 allowed, I'm sure we all have dysfunctional habits. I have lots, but I'm not very good at like, except like, Nope, this is just how it is.

45:56Mario Gabriele:I have to like, this is gonna be how it's going to be. Well, I mean, I suppose some of these things that I write are like things that I'm telling myself. You know, there was a period where I was writing The Generalist very early on and I was, you know, on a weekly cadence, sometimes a couple times a week. 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?

46:34Yeah. And they'll be like, you know, well, if you think about how to, you know, you could use this tool to, you know - Okay. Unplug this new shoot. New genre.

46:43Mario Gabriele:I've not come across this. That's hilarious. I almost don't have the stomach to 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 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's a that was my candied ginger for a period of time i like it um you've evolved the generalists 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 um i had an experience uh last year 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 mid-year.

47:55Mario Gabriele:The other was during 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. Um, 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 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 yeah to what extent i mean do you think about stuff like revenue and viewership and subscribers like do you are 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.

48:54Um, I would say I'd 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.

49:13Mario Gabriele:You're like number six on business sub stack. Like you've done pretty good on that front. Yeah, it's good. I mean, it could be many, many times better, but I'm not convinced that having more people is better in that sense. Like I do think there's sort of this trade-off between popularity and influence. And I'm okay sort of focusing on influence and that could even mean a smaller audience in some situations. 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 yeah I think so good luck beating Founders Fund I think I'll beat it this year I think I will confidently beat it but it was clear Founders Fund was definitely the best there are other pieces maybe I love more or I feel, you know, closer affinity towards, but like objectively that was the best one.

50:13Mario Gabriele:You talk about a debt to modernity. You say to make an impact on the world, you must pay a debt to modernity. It is romantic to imagine succeeding just as your heroes once did, but they lived in a different time in different circumstances. A concession to the present day is necessary. 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 been very good at building like a modern media company, maybe? I think 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.

50:56That was always super tempting to me. And it was why I wrote for 10 plus years before starting The Generalist, thinking that, you know, this will, once I do the work, it's just going to happen. But that's not how things work.

51:10Mario Gabriele:No. No, and it's a blessing and a curse. Yes. Blessing as well, though. Blessing, yeah. Many writers, like, find something that works, and then they, like, keep hitting the ball. I love Ben Thompson. Like, he's added the pie cap, but, like, he is a thing that works. Yes. You have evolved a lot. You've explored so many different types of series, like, in formats, and even doing the podcast now, and it seems like you're shifting towards this much, kind of maybe slower, bigger, more, like why so much of that iteration, given that you've been successful kind of throughout? I think I have to keep it interesting for myself.

51:49I 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. It feels like in some ways it would be unambitious. And I don't mean to cast dispersions on anyone else. Like everyone else has their own versions of ambition. But for me, it would feel unambitious if I was like, okay, I've developed a lot as a writer and a researcher and a thinker, and I'm going to just do it again. Why wouldn't I try and do something like much, much bigger and much, much deeper. That's harder.

52:28That's more interesting. Like you need the friction. Without the friction.

52:32Mario Gabriele:Little meaning. Yeah. So, so I'm, I think it's a reflection of the fact that I am trying to learn a bunch of different things and hopefully the generalist is enough of a vessel to support that and enough of a vessel to support it as my ambition grows. And I want to try and go bigger and bigger. Have you kept anything constant? Is there anything you're kind of that's sacred? Yeah, the writing. Like, 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 or where I aggressively at this point used AI to write drafts and like, you know, it's close enough in some senses.

53:17I think the sacred part is just really caring about the sentences and the flow and all of that. in an obsessive way. And I think that was true at the beginning 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.

53:37Mario Gabriele:Yeah, it's the cliche, like find the thing you don't want to automate. I love David Sanero talks about this and he's like, people will be like, why don't you have someone read the books for you? And he's like, the whole point. That's why I'm doing this. That's why 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 uh 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 yeah um a lot of sponsorship as well.

54:18Mario Gabriele:Then generalist capital, obviously now humming, but 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 with 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 how I've thought about the business and where the advantages are.

54:58And 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. 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. And then, you know, it can make sense, I think more to have a subscription model when you maybe have like a really deep archive, like the value of what you're giving people just hopefully keeps compounding if the things are evergreen in some sense.

55:42So in some sense, they reflect the maturity of the business, but the things that really didn't work were the community and having that as a big part of the subscription. And not because, you know, there were really some amazing people I met through that and some really good sort of friendships that formed. So I'm glad I did it because I've heard of, you know, from some folks that they ended up meeting sort of a co-founder or really, you know, good connection. But from a business perspective, it's really hard to do that, I think, well.

56:15Mario Gabriele:It requires a lot of like gardening. Yeah. And it's just like not by strength. And also we have such a various audience that it's not clear what people are sort of joining for. So, yeah. What about investing? Like when did that first show up? I mean, And 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, uh, that mindset. And I sort of never properly stopped investing. There was maybe like a year where I didn't do much.

56:59Um, 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 then it was

57:11Mario Gabriele:exciting for me to be able to do that more seriously with with generalist capital and 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 i think i was just like i i want to do everything myself at this point i just that was the biggest lesson i had learned was right suddenly i'd made much more progress than I'd ever made in my professional life and felt much more myself. So I couldn't, I couldn't conceive of the idea. It goes back to your answer about the authenticity question, actually, which is like letting the, like, it's all up to me.

57:47Mario Gabriele:Yeah. Like there is. 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, uh, 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 uh 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.

58:37And I find that it is extremely powerful. If you can be the truest believer authentically, that's really attractive to people in any walk of life, but with founders certainly.

58:53Mario Gabriele:There's one reading of this is just like, be warmer and 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 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, when, when the races, when the starting pistol goes off, it doesn't really matter if you're.

59:40You have to show up.

59:40Mario Gabriele:Yeah, you have to show up. You have to, you have to just be ready to rise for that occasion. 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, talking about every second counts and he, he related to it that way, which is like this 8am zoom meeting I have, like might be the the most important meeting of somebody's month.

1:00:12Yes.

1:00:12Mario Gabriele: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 professional life. 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 my assumption would be that you've had at least some amount of, or at least being close to that.

1:00:42Mario Gabriele: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. But I really do think there's 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, 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, just raising the ceiling for someone.

1:01:30And 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.

1:01:40Mario Gabriele:Yeah. I've talked with people more in the kind of like grants side of things. Although I think there's actually some overlap with early estate investing, which is like, sometimes the, that conviction is maybe not more, but close to as valuable as the money. Yeah. A hundred percent. I think much more valuable. It's like, especially if it's a small dollar amount, right? Yeah. Like you're, you're, you're the sort of person who, 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 forward. Exactly. You say the best investors often need little more than a sentence to explain why they've invested in a company.

1:02:17Mario Gabriele:The longer and 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 yeah 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.

1:02:59Yeah. 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.

1:03:16Mario Gabriele:That's really, I know of very serious investors who are not VCs that have the same kind of mental framework. Yeah. And in interviewing so many of these people through the generalist over the years and asking them about their best investments, at first I was really frustrated that a lot of times they would be like, this founder is just insanely good. And you're like, insanely good. Like, but why? Like, you know, come on, help me out here. And I think what you've come to realize is one, the best practitioners are not always great at articulating their craft. And two is that like on some very deep level, they've actually parsed through a ton of information.

1:03:53And that's actually the decisive point still. It's just this person is special. And that's infuriating, I think, in some level.

1:04:00Mario Gabriele: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 of things on the, on the, on the maybe founders fund teal front. There's this thing where you say, I can't remember if it was in the piece or in a podcast, you frame it as sort of like Michael Moritz is like, orientation is like do right.

1:04:40Mario Gabriele:And teal is be right. Which I think is, there's, I mean, there's so much there, but like, I'm curious how you, like, where do you sit in that? Like, how do you relate to that idea? Oh, interesting. And I guess you could, obviously you could take that in this like very blown out kind of moralistic sense, but I'm also just curious about it in the investment sense. I think I'm probably not axiomatic about either case, but I would imagine I lean more Moritz. Like 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 philosophical sense, need to learn when you're breaking the rules cleverly.

1:05:27Well, and there's a tinge of it too around like see the world as it actually is. Yeah, that's right. That's right.

1:05:34Mario Gabriele:You also observe that Teal 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 teal or or otherwise well teal is so smart in the sense that he's built like the peter teal cinematic universe of of different entities um and so rube golder you're just falling through the labyrinth of yeah exactly of lord of the ring names um 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, um, and different, you know, scales of companies, et cetera, et cetera, that I think he has, yeah, a lot of cards at his disposal that he can sort of, uh, make it easy for someone to find their next big thing.

1:06:30Um, 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.

1:06:55Mario Gabriele:My sense is there's an element of, um, at least with Teal, but maybe in that second thing too, is one of the things that's really compounds and it's really hard to start in with is trust. 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 can think about any of us for any of our relationships. When you're in year eight 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, uh, such that I think if he says you should go do this thing, you're like, I don't know.

1:07:39I think I probably should.

1:07:42Mario Gabriele:Yeah. He tends to be right. Yes, exactly. Uh, 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 their personality inside.

1:08:21Mario Gabriele:I'd love to hear you talk more about the texture of someone's mind. 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 do that. People seem to have their own ways of making that happen. You know, Barand, 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 yeah jujitsu move or something right it's pretty remarkable um farat you know the other um that you know the managing partner hummingbird has his own way that again is like pretty magical to 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.

1:09:27So 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 do that. They're almost more information gatherers. Um, and I think that serves them well in lots of, uh, you know, in lots of environments and lots of places. Um, 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 just like speaks to me

1:10:03Mario Gabriele: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 that maybe partially, but it's also, there is this objective function running through it. And that both parties know this, which is really fascinating. Like, and there's a little bit of like, I'm sure performance, but also it goes maybe back to the story underneath the story.

1:10:39Yeah, there are, you know, there's always the game in the metagame.

1:10:43Mario Gabriele:Yeah. And yeah, I think personally, I think that's happening in every conversation. um i think uh 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 um so or or in some way it doesn't always have to be you know it sounds so cynical i don't think it has to be um so that is there but i think it's there all the time whether you you sort of see it or not yeah a related piece to kind of the texture of somebody's mind around motivations. It was less about let's go into the weeds and tell me why you invested in this company.

1:11:23Mario Gabriele: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 Kata 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 And I'm, they're like two different kinds of motivations maybe.

1:12:13Yeah. I think you have to have the second one.

1:12:20Mario Gabriele:I think you can also have the first one. That is not a given. I don't think that most people are taking that. Like I think many people might actually ensue in the inverse. Yeah. And that would not be my observation so far. Right. Right. I think the second one's actually at a much deeper level and is like much more essential to your personality and the way that you grew up and the way you're formed. Right. There's a idea that Barron talks about that reminds me of, I've heard other investors talk about, Chris Peck frames it as like, are they post-death? Barron says, or this is you writing about him, how did it change them?

1:12:59Mario Gabriele:What residue had it left on their selves, their souls, their lives? In particular, he, Barron, was interested in how many entrepreneurs had undergone something that affirmed their fragility, their mortality. He hoped to convince founders to share such experiences, creating a kind of compilation of hardship. It relates to the prior question too. How do you think, I assume you're familiar with the kind of 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, there's a remarkable number of really successful people who's like dad died when they were 14.

1:13:33Ah, yeah.

1:13:35Mario Gabriele: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. But it could also be like, I need maybe the idealistic thing we were talking about earlier. It sounds like maybe I'm answering my own question, but 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 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's an example of truly good fuel? I think the I would say someone like Rick Rubin 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 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, was like I don't love it it's like too intense she took two years off and she came back and was like we're doing it my way, like I have to do this for love I have to do this for art.

1:14:39Mario Gabriele:And she won the Olympic gold. And like, obviously, some aspect of that is somewhat romantic. I'm sure she also had to grind. 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 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 see that. To me, though, that's a story of you had this thing that made you who you were and that forced you to become great.

1:15:14And 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 there are founders you talk to who said oh I had a wonderful childhood and then you'll find out 10 things where you're like you had a wonderful childhood I mean this is actually um have you ever seen the documentary series 100 foot wave no okay it's about it's so good it's about these

1:15:54Mario Gabriele:guys who are trying to surf and a hundred Hamilton type guys yeah like the newer generation older generation. They're going to Nazarene, 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. 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 has a great relationship with his mom.

1:16:26Meanwhile, 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 came from a very, very, very well-adjusted background.

1:16:50Mario Gabriele:Yeah. Yeah. There's a, there's a, a kind of a tenor of tenacity throughout a lot of stuff you've written about, but especially the, 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, um, performance. and there is, again, it maybe comes back to like seeing things as they are, which is like, what does it take? It takes everything. Yeah. It takes everything.

1:17:24Uh, 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 it takes everything is the right way to put it.

1:17:47Mario Gabriele:There's a bit at the end of that Hummingbird piece where you're talking about messiness in the same theme. Hummingbird's greatest talent is that it sees the world as it is, not as we think it should be. It meets reality and invests in it as it is. It is a pragmatic act, but it is also a philosophical one. By successfully investing in the world it sees, Hummingbird affirms reality's integrity. Wanda Brand and Hilarie can generate a return by capitalizing the unreasonable because innovation is unreasonable. Because progress is messy, we scrabble with fingernails full of mud. We pound our bodies bloody against a barrier to see what lies beyond.

1:18:26Mario Gabriele: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. 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 Baran, he's like, doesn't want to tell stories about himself. 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.

1:19:08Mario Gabriele:Do you see what I'm getting at? It feels like in theory there would be some conflict between these two things, and yet it doesn't seem that there is for you. It's telling that you have just joined this firm that is so radically obsessed with this. I guess I think that stories are really true. or the best stories are, 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.

1:19:50And so that's maybe the place where those two things meet in some sense. I like that answer.

1:19:59Mario Gabriele:There's just a short bit where you had met with Gort and Nomads when you were raising for the generalist. Gort, maybe I have that name wrong? Yeah, no, I think that's right. You say, Gort and his colleagues asked questions I received from no other LP. It was reminiscent of conversing with a relentless, precocious child, each question begetting another. What type of founders did I look for? What did that mean? What did that mean? After three or more of these burrowing questions, you begin to realize what you really think and how deeply that thinking goes. 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-ish 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 how you even challenge each other.

1:20:49It definitely comes up, I think, in how we challenge each other. Like, you know, we'll talk a lot about a meeting we had with the founder and, okay, he said this thing.

1:21:01Mario Gabriele: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 that. So, you know, I think earlier in the piece, uh, Salar, the CEO of Monumental talks about Barand being like the most linguistic VC. I was going to bring that up. Um, uh, and 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 Barand's level from an investor perspective. Um, but yeah, there's an obsession with words, language down to like an insanely granular level.

1:21:41I can't, I can't overstate that, honestly.

1:21:45Mario Gabriele:Maybe it relates to your earlier point about stories and like how much context, how much is how, how much resolution is held within them. Um, one reading would be that like overly focusing on words is like missing the forest through the trees. But the other reading it's, it's telling that they also compare it, they're compare Barnd 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 uh consideration precision evaluation whatever yeah also i have to say it's not just the words like there's there's like a huge body language a tone thing like there's uh you know in as a if he was a therapist or a you know a psychological profiler he would be elite.

1:22:37And same for Farad. They're just hyper observant about everything. And words just happen to be a big part of that.

1:22:45Mario Gabriele:You, a couple months ago now, joined them full-time, maybe longer. And you wrote about this in that piece. You said, for six years, I had built the generalist on the conviction that I am only truly myself inside of a structure of my own design. You talked about this earlier. When I thought of prior versions of myself, they always seem ponderous and hazy by comparison. Because of that, similar approaches from funds to join forces over the years had been met with an automatic refusal. But in this instance, for the first time, a refusal did not instinctively arrive. Intuitively, I sense 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.

1:23:25Mario Gabriele: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, you're sure 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, uh, 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 that exactly happen?

1:24:10Or, 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 to 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.

1:25:01So, um, the, the experience with joining hummingbird was really, uh, 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.

1:25:23Mario Gabriele:You seem to have, it's maybe really, it's a little to the evolving, the generalists, like you do seem to have a healthy relationship with your own kind of structures. 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 things change. Yeah. I think, uh, someone shared 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 killy-minded towards that. I'm okay killing off things early.

1:25:58Yeah.

1:25:59Mario Gabriele: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 how much of an actual will-I-won't-I decision it was, where you really had to sit and weigh the rationale, or it was just something that quickly became, or maybe not quickly, but eventually became inevitable and so obvious? I definitely weighed the rationale when I sort of was first starting to work with them as a venture partner, just because of, I think, some of the lessons of the previous years.

1:26:37And 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 commit. And I think you have to be willing in some sense to change your mind up to the last moment of something. 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 want something to be true. And so there was certainly plenty of that. But I will say that from the very beginning, there was some intuitive sense that this is right. Um, and so it was really more about me, me checking that.

1:27:20Mario Gabriele:Hmm. Is there anything you think you've lost or maybe a better way of asking the question? It was 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, um, 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. I was like, there's no way these pieces are getting, no.

1:27:59Um, 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, 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. 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 either a single adult or, you know, someone without a child or without a dog or, you know, any of these things, there's just different levels of wrangling and and planning you have to do to accommodate other other people's needs.

1:28:38Yeah.

1:28:39Mario Gabriele: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 seven-year-old self would find exciting is a pretty good heuristic. You know yourself better at seven than at 22. how does your current work or your current life fit maybe what seven-year-old mario would have aspired to well i think seven-year-old mario uh loved writing and books and also then went through a sharp turn maybe around eight or nine into wanting to be a trader in the stock market no way so so there's uh some good there we go good uh 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 someone 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 consistency of like continuing to raise the bar or like widen the aperture?

1:30:05I think the secret is being a very dissatisfied person is having deep psychological issues. No, I mean, I'm sort of joking, but there is something where I'm just congenitally dissatisfied with the state of things. And that's, you know, the thing that, you know, most philosophy, certainly on the stoic front or something like dedicates you to, to be grateful for, for what you have and accept what you can't control. But, uh, as much as I admire those philosophies and read them, like something, it doesn't seep down to the bedrock.

1:30:40Mario Gabriele: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. And that almost immediately transmutes into anxiety and expectation. But yeah, sometimes that can last more or less time. There are sentences which I'll read sometimes and still think, hey, that was a good one. So some of the ones you've read, I think when I hear you read that, I think, oh, that was good. I haven't stumbled over them too poorly. but no no and then there's something you read and i think i gotta get back in there like i want to change that um can't do that can't do that honestly a a good string of words makes me proud at times yeah 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 like it's almost unexpected it's like a list productivity stack or something yeah yeah it is unexpected um you have this just amazing you talk about how you use cloud basically in all of these amazing ways um even for something as simple as like you say gm in the morning and it like prompts you on all these like it's really cool um as well as like using it as this really robust personal tutor and sort of building a personal curriculum i've talked with other people about this we were just talking about henrik's um 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.

1:32:28Mario Gabriele:But how do you, is that something you aim to, to, to develop or maintain? I mean, I hope I don't lose it. 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 was like a 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.

1:33:16Mario Gabriele:Yeah. I think the answer is, 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 gang, I know enough about Genghis Khan and I don't have really time to read about Genghis Khan, but like there is a, there are a lot of ways to learn. One maybe element of this actually is like you, you have, let me see. Uh, yeah. The 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.

1:33:51Mario Gabriele:I don't have to make myself that much more teachable. Most people aren't there's 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 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 versus like churn you know this isn't that good i'm gonna stop yeah yeah because it can get better.

1:34:31And 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. 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. And there's productive sort of conversation there. And then I think the things that you have to do to make yourself a good student are force yourself to articulate what you've learned. I mean, that's just the difference between consuming and learning.

1:35:04Mario Gabriele:Also a very strong case for writing. Yes, yes. I also really enjoyed your kind of notes summary on improv. And there were a couple of things that stood out. One is there's a huge section on status and like learning to play status. You say one bit stood out, a CEO who wants employees to brainstorm creatively will have much better luck if they lower their status rather than raise it. no one writes poetry in front of a firing squad. In what ways are you actively holding that model in your head or holding this kind of play status thing in your modes as a writer, as an investor? As a writer, that's really interesting.

1:35:41And I haven't thought about it too much.

1:35:43Mario Gabriele:Yeah. Maybe investors 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 in saying everyone should read this. but hopefully there are times where I can play low status in writing also I would imagine in the founders fund like you are or really any of the entrepreneurs you work with the inputs maybe are more low yeah 100 % yeah yeah definitely and then you are sort of hopefully emerging as at least some kind of authority yeah yeah otherwise why are you sharing it there are obviously styles of writing where you can play low status like comedy writing you could certainly play low status Um, investing, I think I'm definitely always interested in what the person is, is playing, uh, and how fast they can, can flip.

1:36:32Uh, you know, are they a status expert as Johnstone would say, um, where they can play low status if it suits the situation and high status, uh, at another moment.

1:36:42Mario Gabriele:He also talks about unlearning and I'm, I'm curious if anything immediately comes to mind as things you've had to unlearn. Yeah. I mean, I think so much we have to unlearn, right? Like our, I don't know if this resonates, but 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 parents gave me was really good, but teachers, things like that, like, you know, you learn 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?

1:37:24Hmm.

1:37:25Mario Gabriele: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. So that's something I'm still on learning. 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 being good at helping people, like allowing people to help you. Yeah. Which at least on the surface could be a little at odds with the halfway thing.

1:38:11Mario Gabriele:Definitely. How do you think about that? Because I think you seem to at least perceive yourself to be quite good at the asking thing. Yeah, I think you have to go above and beyond when you're asking. But when you're being asked, sometimes people will ask you for something, but they actually kind of want you to go 90 % of the way. Yes. Yes. And that's a place. Help me help you. Yeah. And I think that's a place where you can learn to maybe hold that ground a little bit more. Holding your ground is a good mental thing to hold on to. You also, So I love this. This is just kind of out of pocket, but you said most products people contend have taste, show no sign of true deep quality.

1:38:51Mario Gabriele: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. Yes. 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, sort of meeting the user where they are. And I think that's actually true of writing as well. There's a lot of writing that almost assumes a huge amount of knowledge. And you have to calibrate it, you know, for your audience. So it wouldn't make sense for me to start every piece talking about what technology is or what software means.

1:39:32But I do think by and large, there's not a lot of generosity in product and in writing. And so, you know, that could be as simple as having like a really beautiful empty state or onboarding or whatever that might be. But I, yeah, I think there's more to be done in that.

1:39:54Mario Gabriele: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. We want to build delightful products. Yeah, delightful. But delight often just means like there are really nice gradients or there's like a really great dark mode or something like that. I don't know. I do think there are people who care about this deeply and there are obviously many beautiful products. But we also set in place like a set of really strict heuristics at various moments of what we think good is or how certain things are supposed to work.

1:40:28Right. 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 it has some of these qualities that I'd want to tie myself to too much.

1:41:03Mario Gabriele:Yeah. You wrote that you spent nearly a year studying what may be one of the most important companies of our era. Curious if you can give us any kind of teaser for what that might be. It's okay if not. Yeah, I mean, I think it will be obvious what the most important companies are right now in the world, right? There's a certain set of companies that are changing the technology industry and playing major roles in the way that great power conflict is being waged. And so 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?

1:41:46Yeah. Yeah.

1:41:47Mario Gabriele:As if there were not enough things. How's that going? How is it going? It's going quite well compared to a year ago. Okay. I started working with a really incredible editor who is like one of the most acute readers I've ever met 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. And so I've really learned like a huge amount about that. Yeah, about like structuring things and why certain things work and certain things don't that I was missing before. So I actually feel I'm the closest I've ever been to getting a version that I'll be happy with, but I'm also very aware that my time is sparser than it's ever been.

1:42:50And so I'm kind of, that's the part where I feel a bit upset about or a bit stressed about where I'm like, I can now kind of see how to get there for the first time, but I need, it's not going to magically happen. So who knows how long it will take.

1:43:09Mario Gabriele: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 most obvious one is go to my best friend's or one of my best friend's birthday parties and meet my wife. That one's certainly 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 NYU while I was working at a law firm for fiction writing and begin as a 22-year-old to imagine that you are supposed to be writing every single day, not just being sort of a good writer in school and writing when you feel like it.

1:44:06That sort of forced a habit that 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.

1:44:18Mario Gabriele:Sort of becoming the person you imagine yourself to be. 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, that's a, that's a wildly opinionated and probably a banger. Um, how does your wife make you better? I almost disagree with the premise. Um, like I, 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, in every, in every way. And not because she does something that like changes my chemistry.

1:45:04Yeah, 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, yeah, so obvious and so effortless. So I'm very lucky in that sense. So she makes me better, but yeah, she's just miraculous in her own sense.

1:45:28Mario Gabriele:I have one last thing. A pair of quotes, I suppose. This is you first. 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 inminability. I would never have thought of running a newsletter, and yet once I'd begun, it was strange that it had taken me so long. So many of the best things that have happened to the publication, to my investing, my thinking, have arrived from directions I did not anticipate. And then a quote from Oscar Wilde, who I think Barrett brought up with you in that joining Hummingbird piece. Wild says, if you want to be a grocer or a general or a politician or a judge, you will invariably become it.

1:46:09Mario Gabriele: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 uh will always be true i'll always love writing and i'll always love stories.

1:46:54And 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 in the years ahead.

1:47:11Mario Gabriele: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.

1:47:46Mario Gabriele:And I'm excited to see all the ways that I can continue to collaborate with a team of agents to build out dialectic. Also, if you enjoyed the conversation, please give it a thumbs up or five stars wherever you're watching and also subscribe. It actually really truly helps. And if you do subscribe, it will ping you anytime there are new conversations. I've got lots in the hopper. I can't wait to share with you. Thanks again. And I'll see you next time.