43. Mario Gabriele - Reality is Story-Shaped

·Writer, Investor, Creator
Mario Gabriele - Reality is Story-Shaped

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Description

Mario Gabriele (X) is a writer, investor, and analyst. He is founder of The Generalist and Partner Hummingbird.

He aims to bring the rigor of investment analysis with writing quality and style that is closer to the New Yorker. His profiles, deep dives, and briefings are amongst the highest quality writing in the technology business, and he interviews practitioners weekly on his podcast. Recently, he wrote the definitive (and nearly book-length) piece on Peter Thiel’s legendary investment outfit, Founders Fund, and profiled Microsoft’s Satya Nadella.

I spoke to Mario about stories and the truths they hold or reveal. He is a writer first, and it shows in his prose, style, and depth. We also discussed the evolution of The Generalist’s content and business model, both of which he has experimented with ruthlessly. The subscription counts 160,000+ readers / listeners and is currently ranked as the #7 bestseller in Substack’s business rankings. He is also an investor focused on the technology world’s heroes: founders. Hummingbird, which he joined earlier this year, is known for its obsessive approach to understanding the minds, motivations, and worlds of the entrepreneurs it backs. We dive into the under-discussed elements that shape world-beaters, including the notion that ambition almost always comes from some level of pain.

Across the conversation, we talk about how authenticity and evolution run across his career, and how he is at peace as someone who doesn’t know exactly who he is becoming. That generalist orientation continues to produce unlikely paths that surprise him. I hope this conversation inspires you to take stories seriously, to look for what's true beneath the polished surface, and to trust paths you didn't plan for.

**Dialectic is presented by **Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. Notion recently launched custom agents: helpful AI teammates that handle recurring work across your entire suite of tools. Automate you and your team’s repetitive tasks so you can focus on the deep work. You can learn more at notion.com/dialectic.

Timestamps

  • (0:00) Opening Highlights
  • (1:13) Intro to Mario
  • (2:49) Thanks to Notion
  • (3:58) Start: Stories, Truth, Writing, and the Story Beneath the Story
  • (23:39) Failure, Authenticity, Comparative Advantage, and The Most Annoying Aphorism in the World
  • (35:55) The Generalist's Style
  • (45:20) Process, Goals, Vision, Experimentation, and Business Models
  • (57:52) Investing: Energy, First Checks, Notecard-level Clarity, and Peter Thiel
  • (1:07:46) Understanding Founders, Motivation, Good and Bad Fuel, and True Ambition
  • (1:17:47) Hummingbird: Seeing the World as it Actually Is and How Stories Reveal Truth, Linguistics, Observation, Deciding to Join, and Evolution
  • (1:29:32) Motivation, Raising the Bar, Ongoing Learning and Teachability, Status, Unlearning, Generous Products, and The Reward of Not Knowing
  • (1:47:15) Thanks Again to Notion

Links & References

Transcript

(0:00) Opening Highlights

(1:13) Intro to Mario

(2:49) Thanks to Notion

(3:58) Start: Stories, Truth, Writing, and the Story Beneath the Story

Jackson: Here we are. Mario, thank you for being here with me. I'm sorry I didn't nail the Italian pronunciation. Alas, I did my best.

Mario: (4:08) I think it was a very good one. It's great to be here.

Jackson: (4:12) The turntables have turned. You're in your normal spot, so it's fun to be here in London with you.

Mario: (4:19) I'm going to have to pull myself back from getting into interviewer mode and let you take us where we should go.

Jackson: (4:28) I want to start with stories. Unsurprisingly, you wrote a list of observations about how you think and things that feel true to you. There are a bunch of them that resonated, but one was that you become the stories you tell about yourself. I'd like to ask you to reflect on the essential or dominant stories that have felt true for you over time. To the extent those have persisted, compounded, or completely evolved, I'm curious if there are dominant themes that come to mind as you look back.

Mario: (5:11) We might not get to a second question. This is infinitely deep as a place to explore. It's interesting that I make that observation, yet I don't have obvious things that I would definitively point to. Maybe that's a story in itself, that I'm a little hesitant to define myself. Probably the stories I would tell about myself are that a lot of my early life was hyper-focused, achievement-oriented, and outwardly very linear. I was a very serious student and a perfectionist, but with an inner life that didn't get reflected in that sense. It was much more about stories and different explorations. Adulthood is, in some sense, rediscovering the most childlike version of yourself. I feel closer to that than I was ten years ago.

Jackson: (6:15) Certainly, to the point you were making, when you were younger it was more consumption. It was more inputs than outputs, perhaps. You were living in other stories rather than your own story.

Mario: (6:27) When I was very young, the most natural and innate part of myself—from the mythologies you hear from your family—was being obsessed with books, writing, and stories. That was very authentic to who I was from almost birth. Then you try on different identities as you become an adolescent. There was a period where I was going to be a very serious trial lawyer and a politician. That was a very striving, thrusting phase of early adulthood. You integrate lessons from all of it, but hopefully, you come back to yourself.

Jackson: (7:09) I think that's right. You've talked about this before, and I might be slightly paraphrasing, but the most efficient and enjoyable way to learn is through stories.

Mario: (7:20) I do believe that.

Jackson: (7:22) Some people might totally resonate with that. Other people might say stories aren't true. Why are stories so useful?

Mario: (7:37) On some level, you could complain that stories aren't true in the same way you could say language isn't true. It's a distillation of some platonically perfect piece of information. This is the best we have, and stories are just the hyper-effective version of language in my view, because that's how our minds are wired. If I tell you something in a parable or a story, there's a reason that's the foundation of all our religions and political systems. You need founding myths, and those just happen to be so much more durable and magnetic than anything else we can come up with. I think it's just a construct of the way our brains work. It's not an objective reality, it's just a species-subjective reality.

Jackson: (8:34) It's almost like we have to resort to this.

Mario: (8:40) Exactly. This is what our minds want, and this is the story we have to tell ourselves. It's true.

Jackson: (8:47) I'm curious if you find yourself noticing any patterns in the types of stories you tend to gravitate to.

Mario: (8:57) I did a funny exercise where I had Claude look across everything I've written and all of my Readwise highlights. I had it look at the pieces I've saved and try to think about what I'm actually interested in and what I gravitate toward. It reasonably resonated with me. There's some axis between madness and greatness that I'm really drawn to. I'm drawn to what it takes to be great, the level of sacrifice, and the uncomfortable parts of these great personalities. At some level, I'm really interested in the psychological piece because usually that gets collapsed one way or another. It gets collapsed into a hero or it gets collapsed into a villain. The interplay there is deeply intriguing to me. I'm drawn to ambition and what that takes.

Jackson: (10:04) Everyone relates to themselves as the hero of their own story. With that comment in mind, do you ever find yourself monitoring your tendency to place yourself as the hero?

Mario: (10:23) That's a deep, interesting question, and the answer would be yes. For better or worse, I find it very easy to slip into other people's perspective on things. The good part about that is I can almost intuitively understand an argument from another perspective and almost begin to believe it in some sense. I can see the jumps you're making to get there. It's not the jump I would make, but there's a logic to it. The downside is that you can think about those things so much that it takes me an extra beat to listen to myself. I have to hold firm in the idea that this is also a valid way of parsing it.

Jackson: (11:12) I think it involves pulling yourself back or making yourself a little bit smaller for some period of time in a way that you have to reinflate.

Mario: (11:22) Yes. Frankly, the work you do as a podcaster, and that I'm trying to do, requires putting yourself a little bit into the other person's mind. That's part of the fun, but also part of the challenge once the episode ends.

Jackson: (11:40) I wonder if that is a common theme amongst storytellers or especially writers. We have some counterexamples, but writers throughout history aren't often the grand or heroic figures. I was thinking a lot about Proust this week because of a couple of other people I interviewed. Certainly not to compare you to him, but there is the hero and then there is the storyteller talking about the hero.

Mario: (12:15) I'm more comfortable as the storyteller in that sense. There are a lot of fearful writers. Kafka was a terrified person. You don't get that many Hemingways.

Jackson: (12:27) That's exactly who I was thinking of. On that note, what else do you think makes for really great storytellers, or at least the storytellers that you tend to admire?

Mario: (12:41) A level of obsessive observation. I think great writing is often just some version of very precise writing. It's not in the sense that you're going into everything in very granular detail, but you're observing a feeling, an experience, or an occurrence with such fidelity that you're able to make a comparison someone else can't. That's the basis of a good simile or metaphor. It's having that element of surprise. It's almost like a joke in that way. You need there to be some surprise for it to feel fresh. For me personally, I hugely care about the quality of the words. That's hard to be too prescriptive about because I more or less disagree with a lot of writing advice. I don't know if you can really put a set of dictums on what is likely to be good writing. The way good writing forms is insanely diverse. What one person can pull off, another person can't.

Jackson: (13:54) You wrote somewhere in that list of maxims that almost all writing advice is actually copywriting advice.

Mario: (14:00) Yes.

Jackson: (14:02) Why do you think writing advice tends not to be good? What types of things are typically missing?

Mario: (14:09) I think most people who give writing advice are not very good writers.

Jackson: (14:14) The good ones are keeping the secrets.

Mario: (14:15) It's not worth their time. They understand that mastery is not easily...

Jackson: (14:20) Tacit, distilled.

Mario: (14:22) Distilled into a set of rules. Frankly, the people who gain attention in the modern attention economy are not literary novelists. They don't want to play that game in most cases, and are probably not very good at it. There's a level of bluntness that is almost directly opposed to most good literary writing. It tends to be the case that the dominant writing advice for people in our rough milieu is about how to write a really good blog post. That is just copywriting advice, more or less. It's a version of LinkedIn writing advice where you start with this.

Jackson: (15:08) A really good list.

Mario: (15:09) Here's a really stupid hook, and then here are 10 things that you should say. I don't like that because I think it destroys the information landscape that we all have to occupy. It's like a pollutant. I try and avoid it. I don't know if I'm always successful, but I don't recommend people think about it too much unless they're purely pragmatically minded. If you're running a business and you need LinkedIn views, do what you have to do. There are worse crimes to commit, but it certainly wouldn't be my preference.

Jackson: (15:50) I heard you saying that a lot of good storytelling is seeing what's there. It's not the specific phrasing you use, but there's something to that. I was reading about Werner Herzog this week, and there are all these examples of him doing what he calls ecstatic truth. He's not that interested in facts. There's a story of a guy who had some kind of military trauma. He has this part where he closes and opens the door several times as this almost OCD tick to signal he wants to be sure he can get in and out. Herzog added it in. The guy doesn't actually do that.

Mario: (16:28) Oh wow, really?

Jackson: (16:28) Obviously that's a very specific example, but 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 fiction is the shape we give to reality. I'm curious how you think about that tension. You do work that is really interested in what's true and relies on robust analysis. Yet to tell a great story, let alone the truest story, doesn't always align with the exact facts. What is the tension between the precise, evidence-based reality and the elements that actually allow you to point at what you feel you have observed is true?

Mario: (17:29) I love that Herzog anecdote. I fundamentally agree that there are deeper truths in fiction than in non-fiction a lot of the time. Sometimes to explain something with really high fidelity, you almost have to resort to imagination or fiction. For something like The Generalist, the only way I feel comfortable doing that is if I'm explicit that a specific part is imagination. There are pieces I've written where there is a flight of fancy like that. I'm recalling a piece on Rocket Internet where they're at St. Peter's gates. I'm okay trying to make some kind of larger claim, but I wouldn't ever want someone to confuse those things and think it actually happened. You lose trust in the whole enterprise somehow.

Jackson: (18:35) Right. There's a central conceit or premise in the container you've created that promises some baseline.

Mario: (18:48) At some point in my life, I hope I'll write a novel about VC and tech, and then I can talk about truths through that lens. But still, you have a lot of latitude when you write these pieces. You can bring in influences or tell other stories.

Jackson: (19:08) This is what's interesting about Herzog. He's a documentarian in some sense, so there's a fuzziness. But I also hear you on the stakes of getting it right.

Mario: (19:18) But I guess he tells you that it's not real, right?

Jackson: (19:20) I don't think he does.

Mario: (19:21) He doesn't?

Jackson: (19:22) Not in that example, at least. He's doing a project that has a different tenor than yours does. He's studying humanity. But I do think every writer is doing a little bit of this in some way or another.

Mario: (19:39) Definitely. I'm reminded of a documentary by someone who studied the Indonesian genocide. Do you know what I'm talking about?

Jackson: (19:49) No, I don't.

Mario: (19:50) The second one is called The Look of Silence. In the first one, the documentarian goes and meets a bunch of the people who perpetrated the genocide, who are now heroes in Indonesia because they won in some sense. He goes in portraying what he's about to do as a heroic retelling of their story. In doing so, he makes them reenact these specific scenes. It's fantastical and not true in some incidents, but in some cases, it's deeply true and is the first time they're really confronting what they've done. I really admire people who manage to play with that boundary and say something insanely deep because of it. I certainly haven't approached anything on that level yet, but what you're pointing at is very profound.

Jackson: (20:47) I'll find it and link to it. One other note on this. In your Hummingbird piece on Barend, you talk about this story underneath the story. You say it is the job of the venture capitalist to listen to such stories and to poke at them, to find the holes yet to be darned and stick a finger through the fabric, to find the story beneath the one being told, hiding to hear what is being said and what is not. It is interesting that in one part of your professional and creative life, you are the one observing and creating these stories. Then in your investing life, you're the one divining, listening to, and interrogating them. I'm curious how that influences you. Are those two totally different modes? Do you almost have a skeleton key as the listener because you are a storyteller yourself?

Mario: (21:47) That's a really interesting observation. I hadn't put that together. I think the unifying principle is just that I'm a collector of stories. I just want to hear as many as I can. My wife makes fun of me for this because if I have five spare minutes, I'm trying to consume some kind of story, whether that's reading a book, listening to a podcast, or watching a YouTube video. My mind is hyper-oriented to greedily eating as many stories as I possibly can. Founders just happen to have some of the most interesting possible stories. I think it gives me some sort of rough advantage in understanding these narratives. You can see the moves people are making. If someone is too clean a narrator of their own story, there's always something a bit disconcerting about that. It means it has been polished through use, which makes you think a ton about what's being elided.

Jackson: (23:01) There's a good meta reminder that all stories have layers, implicitly or explicitly. When you're writing about Founders Fund, you're seeing the surface-level stuff and the things working underneath. Every story we hear and every story we tell has these inner workings.

Mario: (23:27) There's the photographic negative of every story in some sense. You have the story being told, and then you have the story not being told.

(23:39) Failure, Authenticity, Comparative Advantage, and The Most Annoying Aphorism in the World

Jackson: (23:39) I want to talk about the different modes of the way you work, but before we do that, let's spend a few minutes navigating the path to your current set of things. Another maxim from you is that it should concern you if you have never failed at something. You should fail badly relatively often, otherwise you are playing it too safe. It's cliche, but probably cliche for a reason. I like the way you frame it specifically, which is not necessarily to just fail often. Are there any times you failed badly that you would be willing to share?

Mario: (24:19) I have a bunch.

Jackson: (24:21) At least very memorable or formative ones.

Mario: (24:25) One of the biggest failures for me, which was instructive, was studying abroad in Nepal during my junior year of undergrad. It's not a super legible failure in some ways, but it was a very formative experience because I was hyper-isolated. There were a few other people on the program, but Nepal during that period had lots of load shedding. You had very limited periods of electricity, which meant you had even more limited periods of internet. When you did connect, it wasn't the best connection anyway. It was very hard to leave everyone I knew and be in an environment where the people around me spoke English, but one degree out, there was no English. It was a very different environment. I call it a failure because I struggled so much. I went into it thinking I could put on the costume of the person who can do anything and be put in any environment.

Jackson: (25:39) Comfortable in any environment.

Mario: (25:40) Yes. You have a conqueror's mindset. You think this is a new place, and I shall make it just as magical as anywhere else. I found it productive because it forced me to tear down all of those stories about myself, but I was deeply tormented mentally. I still feel a bunch of sadness about it because I failed to experience so much of what that place had to offer. I missed out on a bunch of the things I wanted to do going into it. I had visions of devoting myself to more serious Buddhist study and meditation, and doing Everest Base Camp. They are bucket-list things, and it sounds silly. Maybe the lessons I took were more important, but it was a big failure. As I reflect on it, that one still feels a bit sore.

Jackson: (26:44) Perhaps it will come back around in some strange way. These things tend to land in the way that we need, not the way we intend, especially things like that.

Mario: (26:59) I think that's right. I'm grateful for it in some sense, and it still bugs you in some sense too.

Jackson: (27:09) One of the cool things about the amazing book you published on Founders Fund is this overwhelming theme of returning to originality, resisting the mimetic flow of the world. You have already done a lot of different things over the course of your life, whether it be law, international relations, fiction, startups, or working at the restaurant. Mike Solana says the way to escape competition is through authenticity, and you talk a lot about finding your own specific game. Authenticity is something I'm really drawn to and care a lot about, but it's also blurry. It's almost like staring at the sun because you can't really look right at it. I'm curious how you have approached trying to get closer to authenticity, not as a threshold to cross, but as a continuous gradient.

Mario: (28:13) 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.

Jackson: (28:31) That's so good.

Mario: (28:34) You either rise to that or you don't. Nepal was a good example because it stripped away a lot of things.

Jackson: (28:43) It's like a distillation.

Mario: (28:44) Exactly. Founding The Generalist was in many senses the most authentic thing I had done professionally precisely because it had that structure of having to do something purely yourself, being purely reliant on yourself. What I've come to believe about myself is that I work best in those environments. That's a nice story to believe because it makes you predisposed to take on more of those risks, but I think there is truth to it.

Jackson: (29:21) In my experience, and I think other people would relate, these things are very obviously authentic in reverse. Looking back, maybe for you starting The Generalist, there is actually a lot of friction in crossing into that. Have you found that to be the case? Has it gotten easier when you're adding things now that feel more authentic, or is it always almost this jiu-jitsu?

Mario: (29:43) Birth is always painful. I think this is a universal constant. Starting a newsletter is much less painful than real birth, I imagine. From my own perspective, the amount I thought it was a risk made me vex over it and ask for advice. Action produces so much information. You could just try and it would be fine. If it didn't work, that would also be okay. It was helped by the fact that I had tried on so many different costumes at various points that I didn't tie my identity too much to it.

Jackson: (30:22) It was looser.

Mario: (30:24) I felt that this feels really true, but if it's not, I'll survive. That's fine. I'll keep figuring it out.

Jackson: (30:34) There's another related thread around 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's pathetic job application. In your conversation with Packy, you were talking about Founders Fund. You said when you 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. That's another way of saying that, in a sense. If I were to take one lesson from the piece as a fund manager, it would be to find that comparative advantage and design the game so you can just do that. With the previous question in mind, and acknowledging that it's a directional gradient and not a threshold, what is your comparative advantage? How have you dialed in the resolution of that over time?

Mario: (31:37) I have to first say how much I truly hate the expression "how you do anything is how you do everything." Even hearing you say it, I find it so stupid. It's obviously incorrect, but it sounds like something that has the rough shape of wisdom, so people have attached themselves to this idea.

Jackson: (31:57) Yes. I'm not prosecuting it.

Mario: (31:59) It sounds like it has the rhythm of wisdom. It's phonically wise, but it is semantically so unwise and untrue. I guess why I hate it so much is because there are a thousand things like that. Maybe I'm just really cued into that one.

Jackson: (32:19) There's something where that's bouncing off of you.

Mario: (32:21) There's probably a bunch of others that I'm taking in, thinking someone paused in just the right way, so now I think that's true. But there's nothing true that has no calories in it. There was a period in my life where I would hear someone say that, especially an authority figure. When I was just getting into the tech world, there were probably founders or venture capitalists who would say something like this. I would think I'm not like that. I know I have differences in how I do different intensities, so I must not be up to it.

Jackson: (32:54) I don't have the juice.

Mario: (32:56) I don't have the grit. I don't have the juice. Look, I'm so much better at writing than I am at something else, or I don't care about this or that. These are all nonsensical things that we use to interrogate ourselves. The person who gave you that horrible piece of wisdom, who put that little software bug in your head, didn't even think about it for one second, in my opinion.

Jackson: (33:19) I want to push slightly. I tend to agree with you, although my sense of the root, at least if I think back to when I'm hearing that, is that the good part of it in theory is about personal standards and integrity to the person who doesn't quite have the job they want yet. It means you should show up at the level you want to be showing up, even if it were your dream job. But again, I'm doing a lot of work.

Mario: (33:46) You're doing a lot of work that's not in there. I look forward to someone coming out with a good defense.

Jackson: (33:54) We welcome it.

Mario: (33:56) I can hear it and see if there's anything to it. I don't believe it, but this is why people have different interesting opinions on things. Maybe that's deeply meaningful to someone, in which case I'm glad it works for them. I don't know what your question was because my rage clouded me.

Jackson: (34:14) Comparative advantage. I'm sure part of it is the story thing, but acknowledging that your answer in five years is going to be different, what is the direction of travel on your comparative advantage? How have you started to dial it in and see it in a bit higher resolution?

Mario: (34:31) I'm a pretty good writer, and I think that's actually rare. There are not that many people who take writing seriously as an activity. There are even fewer people who put in a ton of hours to get good at it, and I definitely did that throughout my life. I have the ability to distill information into a story that is, at its best moments, elegant and true. Particularly with The Generalist, I 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 it's a comparative spectacular.

Jackson: (35:20) It's a comparative advantage.

Mario: (35:21) Put those two things together, and I'm good enough at both that that's enough. Then I think the more fundamental piece is I have a pretty good ability to connect disparate threads and see patterns across different things. That helps you reveal something that's maybe true or make a connection more deeply. Something in that zone.

Jackson: (35:53) I agree.

Mario: (35:54) Thanks.

(35:55) The Generalist's Style

Jackson: (35:55) To talk about writing a bit, you write about things that are relevant, but it's very grounded. Not just in narrative, but very grounded in historical context or the bigger picture. You've talked about how you're not very interested in news. The technology and VC world you operate in is very hyper-present. It's complex, but also very self-referential and insular. I'm curious why that historical grounding is so important to the work you do. Maybe it's just your background in writing, fiction, and literature.

Mario: (36:38) I find that a lot of the more insular references don't really land for me. I'm struggling to think of a good example, but if someone is writing and doing more of that in-joke stuff, it doesn't fit the way my brain parses information.

Jackson: (36:58) That's another good point. The way you do it gives your writing depth, and it probably makes it more accessible.

Mario: (37:06) I think that's probably true, hopefully. The other piece of it is that sometimes when you tell a story in a more provincial sense—and I'm using provincial literally here, not pejoratively—you miss the big shape of it, the big architectural thing that's happening. Sometimes the best way to show people that this actually isn't so different, or that this is extremely profound, is to say we've seen some version of this before and we understand what this might mean or do. There's probably some degree of ego and bombast, where I just like thinking in these grander settings. That can also be a weakness, where you imagine every new feature is some part of the Roman Empire or the Mongol horde.

Jackson: (38:08) Let's dial it back. Is what you do journalism?

Mario: (38:13) I don't think so. I've never perceived myself as a journalist. I think of myself as an analyst.

Jackson: (38:22) What is the difference between those?

Mario: (38:24) A journalist would probably say this is journalism. The argument would be that by not taking on that mantle, you're giving yourself too much of an out or too much latitude. I try and adhere to journalistic standards, but it's true that I've never worked in a newsroom. I'm intuiting that along the way. I always want to be honest and conduct deep research and fact-checking. I am sure someone who's worked at The Guardian or The New York Times would have a different way of processing information. An analyst to me is still fundamentally doing some of that fact-based work, but is happier taking a bit more of an opinion and a bit more of a stance. In the connotations of the financial venture equity analysis world, it's more about the investment lens.

Jackson: (39:30) But it's typically far less narrative. That's what's interesting to me about it.

Mario: (39:35) I don't find most journalism that narrative interesting. Would you call The Atavist journalism? Sort of, but it's much more like long-form magazine writing.

Jackson: (39:50) You make this comparison where you say you're trying to do Wall Street analysis in the shape of The New Yorker, which is a form of journalism, but I hear your point.

Mario: (39:59) The New Yorker writers wouldn't say they are journalists. They'd say they write for The New Yorker.

Jackson: (40:08) I'm partially asking because I've met a few people over the last year doing the podcast who have asserted that I am a journalist, or they ask me if I am one. One of the things rooted in that question, which relates to you and is true for both analysts and journalists, is that there's a tremendous amount of rigor. That rigor is rare in your world. But it sits next to this thing I relate to, which is that you overwhelmingly write positively. That doesn't mean it's a puff piece. If people wanted to be super cynical, they could call it marketing. Some of that's about incentives, but it's an interesting combination of the tremendous rigor of a newsroom, framed as wanting to tell you why this might be great.

Mario: (40:55) It's true. There is a filter that I run most of the time, asking if I want to write about this thing that I think is interesting, good, or important. There is a positive valence on the topics I pick. There are plenty of things where I end up talking about something with a positive valence and actually poke a lot of holes in it. I talk a lot about risks that other people have missed because I don't want it to be a puff piece or marketing. It's undoubted that there is that feeling. That's almost axiomatic because part of The Generalist was a response to the sense that all tech coverage was hyper-negative and missed much of the exciting stuff happening.

Jackson: (41:53) I think that's right. There's this interesting thing where you always refer to The Generalist, not Mario. You use the pronoun "we" more than "I." Maybe that's just a habit, but I'm curious if there was a conscious decision inside of that. I wonder if it relates to any of this other stuff around what the thing is. There are a lot of returns to it being the Mario podcast. People say brands are dead and personalities rule. Yet there's something subtle in the way you've done it.

Mario: (42:27) That's an interesting linguistic observation. On the one hand, there is a structural reason for that now. There are three of us full-time at The Generalist. I run it with my wife, and we also have a third employee, Kian, who's great. So now that is a very real reality. To begin with, I was probably trying to project a greater size and seriousness than it really was.

Jackson: (42:58) I love that. I have a founder friend who has this old doc from when he started his company. He was writing the mission statement, and it was always "we."

Mario: (43:07) There's something where you're trying to say that maybe it is just you, but you're swinging for the fences. I'm really allergic to calling it the Mario show. Attaching identity to work that directly feels wrong to me, and I don't know why.

Jackson: (43:32) I have a quote on observation from you. You say the finest practitioners of a given discipline are often the worst at articulating their craft. Too much of their skill comes from inherent qualities or abilities illegible even to themselves. It's better to watch these people rather than ask them to explain. It's a case against podcasting.

Jackson: (43:54) What makes you good at watching people?

Mario: (43:56) I think I have a pretty good beginner's mind. I will enter something with as much childlike openness as I possibly can, especially if I think this person might have a secret.

Jackson: (44:14) This relates to what we talked about at the top around reducing your own size a little bit to inhabit that space.

Mario: (44:20) It's that willingness to be a little smaller in that space and not come to too many judgments in advance. I find that many people are hidden teachers. If you present as the student, the teacher emerges. A little naivety can go a really long way.

Jackson: (44:48) Be the dumbest one in the room and ask the question.

Mario: (44:50) Exactly. People mostly take pity on that person, such that they will explain it to you.

Jackson: (44:59) It's kind of like saying the wrong thing on the internet. It's an obviously obtuse version of it, but there's an element of that.

Mario: (45:04) That's one of the greatest intelligence gathering techniques of all time. Elicitation and saying the wrong thing. I don't mind that. I feel natural in the position of a student.

(45:20) Process, Goals, Vision, Experimentation, and Business Models

Jackson: (45:20) You wrote something about respecting your process. If you do your best work at 4:00 AM with a bowl of candied ginger, do that. Give yourself the latitude to be a difficult artist when necessary. I felt a little bit of peace reading that. I'm curious if there are any dysfunctional habits that you've allowed yourself to just accept.

Mario: (45:39) Yes, of course. I think there are many, and I cycle through them.

Jackson: (45:47) Just to clarify, I'm sure we all have dysfunctional habits. I have lots, but I'm not very good at accepting that this is just how it is and how it's going to be.

Mario: (45:58) I suppose some of the things that I write are things that I'm telling myself. There was a period very early on where I was writing the Generalist on a weekly cadence, sometimes a couple of times a week. I was going as hard as possible, super fast. 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. It would be explaining how to beat Saw.

Jackson: (46:33) Like how to not die.

Mario: (46:34) Exactly. They'll explain how you could use a specific tool to...

Jackson: (46:41) Unplug this new genre? I've not come across this. That's hilarious.

Mario: (46:45) I almost don't have the stomach to actually watch scary films, but this was somehow compelling to me in ten to twenty-minute increments. This goes against the ideal version I would have of myself. I like to think I'm a more literary person and wonder who would pollute their brain with this nonsense. But I needed it high and low.

Jackson: (47:05) You have to have high and low.

Mario: (47:06) Exactly. That was my candied ginger for a period of time.

Jackson: (47:12) I like it. You've evolved the Generalist a lot over time. One of the things I really appreciate about anybody doing something creative is the mix of conviction and a lightness to rotate through things at a super high level. Somewhere you talked about the goal or the mission being to build the most thoughtful tech publication in the world. I'm more specifically interested in 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. One was to get to 21 episodes of the podcast before mid-year. The other was to run the marathon. There was no input goal. It was just that these are hills I have to climb, and I can climb them by any means necessary. It was an experience of learning the value of very specific, ambitious goals. You talk about the equity analysis meets New Yorker vision. To what extent do you think about metrics like revenue, viewership, and subscribers? Is it much more about putting one foot in front of the other? How do you relate to ambition and raising your bar with specific points on the horizon?

Mario: (48:36) There have definitely been points in the journey where I've set a goal for a certain number of subscribers or a specific revenue target. Other times, the goal was launching the podcast or giving a new project a good effort. I think about that a lot less now. On some level, I don't mind too much if we grow a lot in terms of top-line subscribers. We have 160,000 people. I would love more people to come in, which is great.

Jackson: (49:12) You're number six on the business Substack. You've done pretty well on that front.

Mario: (49:18) It's good. It could be many times better, but I'm not convinced that having more people is better. I think there's a trade-off between popularity and influence. I'm okay focusing on influence, and that could even mean a smaller audience in some situations. I don't really think about that anymore. I more think about whether I can write a piece this year that footnotes the last best piece I wrote.

Jackson: (49:48) Is that purely a vibes thing? Will you just know when you've done it?

Mario: (49:52) I think so.

Jackson: (49:55) Because I think Founders Fund is going to be...

Mario: (49:57) I think I'll confidently beat it this year. It was clear Founders Fund was definitely the best. There are other pieces maybe I love more or feel closer affinities towards, but objectively, that was the best one.

Jackson: (50:13) 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, that has been most tempting for you to be romantic about or wish was still the case, as someone who's been very good at building a modern media company?

Mario: (50:45) I think just trusting that your work will eventually find a home and its quality will speak for itself without caring about distribution through the internet. That was always super tempting to me, and it was why I wrote for over ten years before starting the Generalist. I thought that once I did the work, it was just going to happen. But that's not how things work.

Jackson: (51:10) It's a blessing and a curse. Many writers find something that works and then they keep hitting the ball. I love Ben Thompson. He's added the podcast, but he sticks to the thing that works. You have evolved a lot. You've explored so many different types of series, formats, and you're even doing the podcast now. It seems like you're shifting towards slower, bigger pieces. Why is there so much iteration, given that you've been successful throughout?

Mario: (51:45) I have to keep it interesting for myself. I would not be excited to write the same style of piece for the next twenty years. I'm interested in 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. I don't mean to cast aspersions on anyone else, as everyone has their own versions of ambition. But for me, it would feel unambitious if I decided I've developed a lot as a writer, researcher, and thinker, and I'm just going to do the same thing again. Why wouldn't I try and do something much bigger and deeper? That's harder and more interesting. You need the friction. Without the friction...

Jackson: (52:33) There is little meaning.

Mario: (52:33) Exactly. It's a reflection of the fact that I'm trying to learn a bunch of different things. Hopefully, the Generalist is enough of a vessel to support that as my ambition grows and I want to try and go bigger and bigger.

Jackson: (52:53) Have you kept anything constant? Is there anything that's sacred?

Mario: (52:57) The writing. There would be a version of the Generalist that I haven't been able to get behind where I had many more writers or aggressively used AI to write drafts. It's close enough in some senses. The sacred part is just really caring about the sentences and the flow in an obsessive way. That was true at the beginning when I had less skill. Hopefully, it's true now and will be true in the future when I'll think I was doing a terrible job today.

Jackson: (53:37) It's the cliche, find the thing you don't want to automate. I love when David Senra talks about this. People will ask why he doesn't have someone read the books for him for Founders. He says that's the whole point.

Mario: (53:49) That's why I'm doing this. That's what I like doing.

Jackson: (53:52) You have changed a bunch and explored different business models. I found something from November 2022 where you said the paywall doesn't make as much sense. You thought it makes more sense to make content free and that sponsorship is a much better business model. A core part of the subscription around then was actually about the community piece. You had a lot of sponsorship as well, then Generalist Capital, and now Hummingbird. I'm mainly curious for your reflection on one precise question: putting the entire Founders Fund thing behind the paywall. Why does the paid subscription actually make sense, especially for someone at your scale? More broadly, I'd love your reflections on navigating the business model side of all this. Why have you landed where you have, including monetizing via investing?

Mario: (54:49) There have been different seasons of how I've thought about the business and where the advantages are. What I've come to realize is I probably thought about sponsorships versus subscriptions much too much as a binary. It's probably not an accident that every media company eventually tends to converge on doing both. I do think there are reasons why it made sense to be sponsorship-heavy at the beginning, because you're trying to build the audience as much as possible. Having more work open on balance probably makes sense. It can make more sense to have a subscription model when you have a really deep archive. The value of what you're giving people hopefully keeps compounding if the things are evergreen. In some sense, they reflect the maturity of the business. The thing that really didn't work was having the community as a big part of the subscription. There are some amazing people I met through that and some really good friendships that formed. I'm glad I did it because I've heard from some folks that they ended up meeting a co-founder or a really good connection. But from a business perspective, it's really hard to do that well.

Jackson: (56:15) It requires a lot of tending and gardening.

Mario: (56:19) That's just not my strength. We also have such a varied audience that it's not clear what people are joining for.

Jackson: (56:31) What about investing? When did that first show up? Had you done any investing prior to the Generalist?

Mario: (56:40) I'd worked as a VC for a few years. That was part of the reason the Generalist has the lens it does, coming into it with that mindset. I never properly stopped investing. There was maybe a year where I didn't do much, but pretty quickly I was doing some scouting and angel investing. Once the Generalist felt like it was past the stage of survival, it was exciting to be able to do that more seriously with Generalist Capital.

Jackson: (57:15) We'll talk more about Hummingbird, but why was it Generalist Capital and not plugging into a bigger entity?

Mario: (57:24) At least back then, I just wanted to do everything myself. That was the biggest lesson I had learned. Suddenly I'd made much more progress than I'd ever made in my professional life and felt much more myself. I couldn't conceive of the idea of plugging into something else.

(57:52) Investing: Energy, First Checks, Notecard-level Clarity, and Peter Thiel

Jackson: (57:41) It goes back to your answer about the authenticity question. It's all up to you. I want to talk a lot more about investing. One place to start is from your maxims, where 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 specifically in this context?

Mario: (58:07) A lot of people come into conversations more wishy-washy or, for good reasons, more default skeptical. You definitely need that as an investor. But there is a point at which the conversation flips from one person selling to the other. I don't know if people always understand that transition or are ready for it. 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.

Jackson: (58:54) There is one reading of this, which is to just be warmer and more excitable. But the last bit you mentioned is doing it authentically, even in terms of the energy you have to give. Some conversations are very energizing and it's easy to have energy run off, while other conversations aren't. How can you bring energy to the table consistently in a way that isn't contrived? I don't want to say faking it, because I think that's definitely wrong.

Mario: (59:26) I think of it like you have to perform. Not like an actor performs, but like an athlete performs. When the starting pistol goes off, it doesn't really matter how you're feeling.

Jackson: (59:40) You just have to show up.

Mario: (59:45) Absolutely. 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 the other person isn't giving you much, that's your responsibility.

Jackson: (59:56) That rhymes with something I discussed with Chris Paik as well. There's an episode of The Bear about how every second counts, and he related to it that way. This 8:00 AM Zoom meeting might be the most important meeting of somebody's month.

Mario: (1:00:12) Yes.

Jackson: (1:00:12) And I have to show up for that.

Mario: (1:00:14) It might be the most important meeting of your year. Maybe not your life, because that discounts too much family stuff.

Jackson: (1:00:21) I talked to Andrew Reid about this too. You don't know what day is going to be the thing. You get pulled into it.

Mario: (1:00:29) You don't know who's walking through the door.

Jackson: (1:00:31) I think this relates a little. You also talk about this very special relationship of being the first check. My assumption would be that you've had at least some amount of that, or been close to it. What is so special about that relationship?

Mario: (1:00:46) I'd always heard that from other VCs. The reason they were able to double and triple down into a winning company despite it becoming insanely competitive was because they were the first ones there. I was always a bit skeptical because I've had good relationships with founders, but I really do think there's something special about being the first believer. It's the same thing Tyler Cowen has written about. One of the best things you can do for a talented young person is to tell them they can do ten times more than they're doing. You're essentially dogmatically raising the ceiling for someone. There's something to that. Being the first person to say, "I actually see your talent and believe in you, and I think this can be massive," is very memorable.

Jackson: (1:01:40) I've talked with people more on the grants side of things, although I think there's some overlap with early-stage investing. Sometimes that conviction is close to as valuable as the money.

Mario: (1:01:54) 100%.

Jackson: (1:01:56) It's much more valuable, especially if it's a small dollar amount.

Mario: (1:01:59) You're the boatman taking them across the river. In some sense, they would have gotten across anyway.

Jackson: (1:02:08) Right. Maybe you pulled them forward.

Mario: (1:02:11) Exactly.

Jackson: (1:02:12) You say the best investors often need little more than a sentence to explain why they've invested in a company. The longer and more convoluted your investment rationale is, the more skeptical you should be of it. I've heard this pattern from very successful people across different fields, certainly not just venture capital. Can you give an example or reflect on the people you know who are very good at this? It's a really cool line to hear, but doing that in practice is insanely hard. I'm curious who is good at it or how you even become good at it. You also say somewhere else that if a rationale can't be distilled onto a note card, you probably don't have enough clarity.

Mario: (1:02:58) For investing, there's often so much skepticism around venture, and part of it is earned. People will say the average VC's rationale for something would fit on a napkin. That's actually good.

Jackson: (1:03:16) I know very serious investors who are not VCs that have the same mental framework for opportunities.

Mario: (1:03:23) In interviewing so many of these people through the Generalist over the years and asking them about their best investments, I was frustrated at first. A lot of the time they would say the founder is just insanely good. You want to ask why and have them help you out. I've come to realize two things. First, the best practitioners are not always great at articulating their craft. Second, on some very deep level, they've parsed through a ton of information, and that remains the decisive point. It's just that this person is special. That's infuriating. On some level, it's more—

Jackson: (1:04:00) Earned. That's the thing you don't see. They've earned the ability to let everything else fall away.

Mario: (1:04:06) Yes. For them, saying this person is extremely good or insanely good means something very specific. Those are many of the best articulations of why great people invest in a company, even if it doesn't give you exactly what you want.

Jackson: (1:04:27) A couple things on the Founders Fund and Thiel front. You framed it once that Michael Moritz's orientation is 'do right' and Thiel's is 'be right.' There's so much there. Where do you sit in that? How do you relate to that idea?

Mario: (1:04:50) Oh, interesting.

Jackson: (1:04:51) You could obviously take that in a very blown-out, moralistic sense, but I'm curious about it in the investment sense.

Mario: (1:05:00) I'm probably not axiomatic about either case, but I imagine I lean more toward Moritz. There's some part of me that wants to make sure we do everything the right way. I've come to appreciate more that you really need to learn when you're breaking the rules cleverly—not in an illegal sense, but in a philosophical sense.

Jackson: (1:05:27) There's a tinge of it, too, around seeing the world as it actually is.

Mario: (1:05:31) That's right.

Jackson: (1:05:33) You also observe that Thiel is unusually creative at hanging onto talent. Why do you think great talent hangs around, whether it be with Thiel or otherwise?

Mario: (1:05:50) Thiel is so smart in the sense that he's built the Peter Thiel cinematic universe of different entities.

Jackson: (1:05:59) Rube Goldberg. You're just falling through the labyrinth.

Mario: (1:06:01) Exactly. It's a labyrinth of Lord of the Rings names, and there's almost no incentive to leave. It's like Google having laundry on the premises. If you can give someone a great new mission, there are enough different kinds of roles and different scales of companies. He has a lot of cards at his disposal to make it easy for someone to find their next big thing. In terms of retaining talent more generally, I'm very much just learning that from other people. It feels like people are always maximizing some version of compensation, learning curve, and autonomy. Maybe there's one or two others in there, but you're just trying to optimize that configuration for different people.

Jackson: (1:06:55) My sense is there's an element of trust, at least with Thiel, but maybe in that second thing, too. Trust really compounds, and it's really hard to start anew with.

Mario: (1:07:08) Yeah.

Jackson: (1:07:08) If you can manage those other things you said, you get to stay in the field of trust. Especially for Teal, that really compounds. If you think about any of our relationships, when you're in year eight with somebody, it's a very different thing than rebuilding.

Mario: (1:07:25) That's very true. It's especially true with him because the people who stick around seem to hold him in insanely high regard. If he says you should go do this thing, you think you probably should.

Jackson: (1:07:40) He sees something I don't see. He tends to be right.

Mario: (1:07:43) Exactly.

(1:07:46) Understanding Founders, Motivation, Good and Bad Fuel, and True Ambition

Jackson: (1:07:46) 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. I'll share a couple of quotes. You say you cannot expect to underwrite founders well if you do not focus your attention on who they are. Too much time is spent on CAC, LTV, and product features, and too little on the texture of someone's mind. Hummingbird's chief virtue is its ability to ask questions that give these anomalous founders the comfort to open their metaphorical iceboxes and reveal the strange, raw edges of their personality inside. I'd love to hear you talk more about the texture of someone's mind. How do you ask questions or 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?

Mario: (1:08:37) It's really hard to do that. People seem to have their own ways of making that happen. Barend has a unique genius for creating that environment for people, sometimes almost out of nothing, instantaneously. There's a sort of divine...

Jackson: (1:09:01) Genesis, like he could just pull a jiu-jitsu move or something.

Mario: (1:09:03) It's pretty remarkable. Firat, the other managing partner at Hummingbird, has his own way that is pretty magical to see. Everyone has to find their own style. You have to do that in a podcast. You have people sit down, probably meeting them for the first time, and you ask them really deep questions, so you have a way to do it too. Many investors almost haven't oriented themselves to do that. They're more information gatherers. That serves them well in lots of environments, but Hummingbird does something very different. It's much more similar to what you would do in this sort of conversation and what I try to do in The Generalist. That speaks to me and makes sense to me in some way.

Jackson: (1:10:05) What's interesting about that is I have some challenge in what I do, but I also have no ulterior motive. In theory, my job is just to make the best content. My goal is to make the person shine in the way that I see them. What they're doing, or what you're doing now, might partially be that, but there is also this objective function running through it. Both parties know this, which is really fascinating. There's a little bit of performance, but it also goes back to the story underneath the story.

Mario: (1:10:39) There is always the game and the metagame. Personally, I think that's happening in every conversation. That's true even for a podcast, or maybe not with your dearest people.

Jackson: (1:10:58) Sure.

Mario: (1:10:59) But probably at some level or in some way. It sounds cynical, but I don't think it has to be. It is there all the time, whether you see it or not.

Jackson: (1:11:15) A related piece to the texture of somebody's mind is around motivations. It was less about going into the weeds and telling me why you invested in this company. It was more around why we are sitting here, why you are doing this, and why you are building the firm the way you're building it. We both know Anjan Katta well, who runs Daylight. Anjan is a remarkably idealistic founder, deeply mission-driven. There are personal motivations inside of that mission, but it is idealistic. My question is, how important is the "why" in the almost external sense of the mission versus the quality of ambition and the fuel around the person's need to prove something? Does that delineation make sense? They're two different kinds of motivations.

Mario: (1:12:13) I think you have to have the second one. You can also have the first one.

Jackson: (1:12:22) That is not a given. I don't think most people are taking that. Many people might actually assume the inverse.

Mario: (1:12:30) That would not be my observation so far. The second one is actually at a much deeper level and is much more essential to your personality, the way you grew up, and the way you're formed.

Jackson: (1:12:45) There's an idea that Barend talks about that reminds me of what I've heard other investors talk about. Chris Paik frames it as whether they are post-death. This is you writing about him: "How did it change them? What residue had it left on their selves, their souls, their lives? In particular, Barend 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. I assume you're familiar with the good fuel versus bad fuel frame.

Mario: (1:13:22) No. What is that?

Jackson: (1:13:23) Bad fuel would be like what Patrick O'Shaughnessy talks about. There's a remarkable number of really successful people whose dad died when they were fourteen.

Mario: (1:13:33) Ah, yeah.

Jackson: (1:13:35) Or just some kind of self-punishing. Good fuel can be very internal. It can be this artistic, authentic drive. But it could also be the idealistic thing we were talking about earlier. It sounds like you're saying the importance is that there's fuel at all, some kind of rich fuel.

Mario: (1:13:54) I guess I need to read more about it, but I'm skeptical about the idea of good fuel. Maybe that's too cynical, but what's an example of truly good fuel?

Jackson: (1:14:08) I would say someone like Rick Rubin presents as somebody who's just doing it for the love of the game. There was this whole thing recently about Alysa Liu, the American figure skater at the Olympics. She had quit. She literally competed in the last Olympics, had an overbearing dad, and quit because she didn't love it and it was too intense. She took two years off, came back, and said she wanted to do it her way. She had to do this for love and for art, and she won the Olympic gold. Obviously, some aspect of that is romantic, and I'm sure she also had to grind.

Mario: (1:14:45) Yeah.

Jackson: (1:14:46) It seems broadly that, and maybe it's just a narrativization thing, stories we tell ourselves. But as artists and people become more successful over time, in theory at the very least, they tend to shift from bad fuel to good fuel. It's something that allows you to go farther and longer.

Mario: (1:15:04) I could see that. To me, though, that's a story of having this thing that made you who you were and forced you to become great. Then, maybe to reach some different level, you find new sources of energy. I don't think you become the person who is able to manifest this good fuel without the overbearing dad story. I have not seen someone who's so well-adjusted and seems full of ambition. People might tell you that's the case. There are founders you talk to who say they had a wonderful childhood. Then you'll find out ten things where you question if they really had a wonderful childhood. Have you ever seen the documentary series 100 Foot Wave?

Jackson: (1:15:51) No.

Mario: (1:15:52) It's so good. It's about these guys who are trying to surf—

Jackson: (1:15:55) A hundred-foot wave. Laird Hamilton-type guys.

Mario: (1:15:57) The newer generation and the older generation are going to Nazaré in Portugal, trying to surf these monster waves. If you fall, it's like falling off a skyscraper that's moving underneath you. It's insane. No one should try to do this, but these people are doing it, and I hugely admire them. The protagonist is this guy, Garrett McNamara, who's this old, grizzled surfer. His wife always says he had a great childhood and a great relationship with his mom. Meanwhile, he got separated from his brother as a kid. He was raised in a cult for a period of time. He had no shoes and no money. You can't trust the narrative. I don't say this to be dogmatic. I would be sincerely interested if someone has a case where a person was hyper-ambitious and came from a very well-adjusted background.

Jackson: (1:16:50) There's a tenor of tenacity throughout a lot of the stuff you've written about, especially the Hummingbird pieces. There's almost a ferociousness that runs through it. An important backdrop for this is that we're not just talking about some level of ambition. We're talking about true world-beater, elite performance. It comes back to seeing things as they are. What does it take? It takes everything.

Mario: (1:17:23) It takes everything. Even when you look at these stories, sometimes they look like they had a lovely childhood, but because of the way this person's mind works, it was torture. There are different ways that people perceive the same set of circumstances. I think saying it takes everything is the right way to put it.

(1:17:47) Hummingbird: Seeing the World as it Actually Is and How Stories Reveal Truth, Linguistics, Observation, Deciding to Join, and Evolution

Jackson: (1:17:47) There's a bit at the end of that Hummingbird piece where you're talking about messiness in the same theme. "Hummingbird's greatest talent is that it sees the world as it is, not as we think it should be. It meets reality and invests in it 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. Vonderbrand and Ileri can generate a return by capitalizing on 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." "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.

Mario: (1:18:37) Thank you.

Jackson: (1:18:38) This almost feels a little bit at odds with your obsession with stories. Clearly, it isn't, but there is this radical obsession with what is truly, grittily real. Even when you're talking to Barnes, he doesn't want to tell stories about himself. Yet, without losing any rigor or truth, a lot of your writing has a poetic nature to it. Do you see what I'm getting at? It feels like, in theory, there would be some conflict between these two things, and yet it doesn't seem that there is for you. It's telling that you have just joined a firm that is so radically obsessed with this.

Mario: (1:19:23) I think that stories are really true, or the best stories are truest in some sense. Not in the purely rigorous, factual way, but in the Herzogian way.

Jackson: (1:19:37) Yeah.

Mario: (1:19:38) I think the same is true of poetry.

Jackson: (1:19:41) Right.

Mario: (1:19:41) Poetry is sometimes just so acute that it says something much more truly than dispassionate facts could. That's the place where those two things meet in some sense.

Jackson: (1:19:57) I like that answer. There's a short bit where you had met with Gort and Nomads when you were raising for The Generalist. Maybe I have that name wrong.

Mario: (1:20:08) No, I think that's right.

Jackson: (1:20:09) 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? 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 expanding it out to the broader Hummingbird world. I'm curious how you and your newish team bring that vibe or specific way of doing things into the daily work with founders and how you even challenge each other.

Mario: (1:20:49) It definitely comes up in how we challenge each other. We'll talk a lot about a meeting we had with a founder, and someone will say, "He said this thing. This is what I thought it meant," or, "This is how it made me feel," or, "This is what I observed." Someone else will say they didn't notice that or they parsed it in a very different way. Earlier in the piece, Salar, the CEO of Monumental, talks about Bahrand being the most linguistic VC.

Jackson: (1:21:21) I was going to bring that up, and I would compare you in some way.

Mario: (1:21:27) Hopefully, I'm linguistic. I have a long way to go to be at Barnes's level from an investor perspective. There is an obsession with words and language down to an insanely granular level. I can't overstate that.

Jackson: (1:21:45) Maybe it relates to your earlier point about stories and how much context and resolution is held within them. One reading would be that overly focusing on words is missing the forest for the trees. It's telling that they compare Bahrand in the linguistic sense to Michael Moritz, who is known as legendary but also very intuitive. It's almost like taking words so seriously because you know how much is possibly contained in them, and thus they require far more consideration, precision, and evaluation.

Mario: (1:22:19) I have to say it's not just the words. There's a huge body language and tone thing. If he was a therapist or a psychological profiler, he would be elite. And the same goes for Farat. They're just hyper-observant about everything. Words just happen to be a big part of that.

Jackson: (1:22:45) A couple of months ago, you joined them full-time, and you wrote about this in your piece. You said, "For six years I had built The Generalist on the conviction that I am only truly myself inside of the structure of my own design." You talked about this earlier. "When I thought of prior versions of myself, they always seemed ponderous and hazy by comparison. Because of that, similar approaches from funds to join forces over the years had been met with an automatic refusal. But in this instance, for the first time, a refusal did not instinctively arrive." "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, playing your own game, and leaning into your strengths. I'd love to hear you talk about the emotions going into that decision. What were the things lost and the things gained? In what ways are you noticing yourself sharpening?

Mario: (1:23:45) Already, my ability to observe and ask questions has definitely sharpened. I think you can discover some things for yourself, but somehow seeing two people who are sincerely world-class at this, you can't help but observe and look back on a conversation and think, "How did that happen?" That has been a real gift and something I've loved so much about that period. The feeling I have so far, and it's been proven very true over the past year plus, has just been how intuitive it has felt. I never thought I would find a place where I really sensed I fit in, and where we had the same ability to connect at this very high fidelity, beyond maybe your oldest friends, your spouse, or your partner. This was a case where, in a very small number of meetings, it was a real mind meld. But there's also enough diversity that keeps it sharp and allows you to spar well. The experience of joining Hummingbird was almost this massive intuitive pull, even as some set of rules I had set for myself held me back at first. I told myself, "Don't forget you're only good if you do your own thing." At some point, I learned to let go of that.

Jackson: (1:25:23) This relates a little to evolving The Generalist. You seem to have a healthy relationship with your own structures. Maybe this was a pretty rigid one, but you seem to be pretty good at allowing them to serve you and then being able to drop or evolve them as things change.

Mario: (1:25:41) Someone shared the saying, "Sometimes you have to know when to kill something before it kills you." There's something really true about that, and I may be particularly minded towards it. I'm okay killing off things early.

Jackson: (1:25:58) You say, "Learn to respect the process of the unconscious mind, especially in creative matters. 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. Did you really have to sit and weigh the rationale, or was it something that eventually became inevitable and obvious?

Mario: (1:26:26) I definitely weighed the rationale when I was first starting to work with them as a venture partner, just because of some of the lessons of the previous years. It's also just the way I'm wired. I want to analyze something from every possible angle before I commit. I think you have to be willing to change your mind up to the last moment of something. You never know what information or signals you're going to get. Sometimes we can overcommit to something too fast because we want it to be true. There was certainly plenty of that, but from the very beginning, there was an intuitive sense that this was right. It was really more about me checking that.

Jackson: (1:27:20) Is there anything you feel like you really had to give up?

Mario: (1:27:28) Of course. You give up total control of your schedule. There's a level of control that I get to have when The Generalist is my only thing. If I don't want to do any meetings for a week, that's totally fine.

Jackson: (1:27:46) By the way, at this firm, apparently people are meeting thirty companies a week.

Mario: (1:27:50) Sometimes it's insane. Not me, but people on the team are.

Jackson: (1:27:56) I was thinking there's no way these pieces are getting written.

Mario: (1:27:58) Frankly, Hummingbird is insanely anti-structure. If I said I needed time to work on something, there would be no problem with that. But ultimately, you don't want to disappoint the people you're working with. You don't want to be the bottleneck in anything. There's just a different level of consideration that you have to have. In the same way that when you transition from being a single adult to someone with a child or a dog, there are just different levels of wrangling and planning you have to do to accommodate other people's needs.

Jackson: (1:28:38) We meet the intensity required.

Mario: (1:28:43) Exactly. For the most part, I feel like that's not something lost, but something that has actually been really good for me.

Jackson: (1:28:51) You also have a maxim where 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 twenty-two." How does your current work or your current life fit what seven-year-old Mario would have aspired to?

Mario: (1:29:12) Seven-year-old Mario loved writing and books, and then went through a sharp turn around eight or nine into wanting to be a trader in the stock market.

Jackson: (1:29:24) No way.

Mario: (1:29:25) So there are some good threads there.

(1:29:32) Motivation, Raising the Bar, Ongoing Learning and Teachability, Status, Unlearning, Generous Products, and The Reward of Not Knowing

Jackson: (1:29:29) You were talking to somebody once and said that one of the most generous things you can do for someone is to push them well beyond what they're expecting of themselves. You alluded to this earlier when you talked about scaling your own expectations of yourself. This relates to the conversation about being able to drop things. How do you build rhythm or systematize the consistency of continuing to raise the bar or widen the aperture?

Mario: (1:30:05) I think the secret is being a very dissatisfied person, having deep psychological issues. I'm sort of joking, but I'm congenitally dissatisfied with the state of things. Most philosophy, certainly on the stoic front, dedicates you to be grateful for what you have and accept what you can't control. As much as I admire those philosophies and read them, something doesn't seep down to the bedrock.

Jackson: (1:30:40) I'll invert it then. What have you been most proud of at different stages?

Mario: (1:30:48) There are a few minutes after a piece I've written goes out that I feel sincerely proud. That almost immediately transmutes into anxiety and expectation, but sometimes that can last more or less time. There are sentences I'll read sometimes and still think that was a good one. When I hear you read some of the ones you've read, I think that was good.

Jackson: (1:31:16) I haven't stumbled over them too poorly.

Mario: (1:31:18) Then there are some you read, and I think I've got to get back in there. I want to change that. Honestly, a good string of words makes me proud at times.

Jackson: (1:31:30) As it should. I have a handful of miscellaneous things before we wrap up. I would encourage people to read your 2026 list. It's almost unexpected, like your productivity stack.

Mario: (1:31:45) It is unexpected.

Jackson: (1:31:46) You talk about how you use Claude in all of these amazing ways. Even something as simple as saying GM in the morning and it prompts you, it's really cool. You also use it as a robust personal tutor to build a personal curriculum. I've talked with other people about this. We were just talking about Henrik's early lives geniuses and this tutoring thing. My question is a little higher level. You have a deep level of intellectual humility in the way you show up. I'm sure part of that is what makes a good writer and investor, but is that something you aim to develop or maintain?

Mario: (1:32:34) I hope I don't lose it. I think it's mostly true. I'm sure someone in my life would say I'm an egomaniac about certain things. We all have our flights of fancy. One of the things you learn studying great founders and reading great books is that you are barely scratching the surface of what ambition, greatness, and doing great work means. I wouldn't want to foreclose my ability to create great work by imagining I've arrived.

Jackson: (1:33:16) I respect that a lot. I would encourage people to read it. You say you know enough about Genghis Khan and don't have time to read about him, but there are a lot of ways to learn. One element of this is that Claude created a pedagogical approach to teaching you, like Markdown Dog. How do you make yourself more teachable?

Mario: (1:33:46) 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.

Jackson: (1:33:53) Most people aren't. Part of this is you have an intensity and desire. People are trying to learn with these things a lot of the time, and they're not as effective as you.

Mario: (1:34:06) How do I make myself more teachable? I give it a lot of feedback. I'll tell it when a method was a terrible way to teach me. Sometimes it will index on a set of questions that actually aren't deep. You can take on the role of the precocious student who is questioning the teacher a bit. If you tell it to, it will also push back on you and say it thinks a question is deep. I have learned to trust that pushback. Sometimes I'll push back and it will say I might be letting myself off the hook and that I should understand the concept. There is a productive conversation there. To make yourself a good student, you have to force yourself to articulate what you've learned. That's the difference between consuming and learning.

Jackson: (1:35:04) That's also a very strong case for writing. I really enjoyed your summary notes on improv, and a couple of things stood out. There's a huge section on learning to play status. You highlighted that 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 playing status in your modes as a writer or an investor?

Mario: (1:35:39) As a writer, that's really interesting, and I haven't thought about it too much.

Jackson: (1:35:43) Maybe being an investor is a little more intuitive.

Mario: (1:35:45) As a writer, I'm probably playing high status a lot of the time. There is something almost default high status in saying everyone should read a piece, but hopefully there are times where I can play low status in writing.

Jackson: (1:35:59) I would imagine with Founders Fund or any of the entrepreneurs you work with, the inputs are maybe more low status.

Mario: (1:36:08) Definitely. Then you are hopefully emerging as at least some kind of authority, otherwise, why are you sharing it? There are obviously styles of writing where you can play low status, like comedy writing. You could certainly play low status investing. I'm always interested in what status a person is playing and how fast they can flip. Are they a status expert, as Johnstone would say, who can play low status if it suits the situation and high status at another moment?

Jackson: (1:36:42) He also talks about unlearning. I'm curious if anything immediately comes to mind that you've had to unlearn.

Mario: (1:36:48) There is so much we have to unlearn. Most advice you're given growing up as a kid from authority figures is mostly not good. The advice my parents gave me was really good, but from teachers and others, you learn to set a very specific set of options in your mind. The reality is there's much more available to you.

Jackson: (1:37:20) Have there been any things that have been particularly hard to unlearn, or hard to let go of?

Mario: (1:37:28) I think there's something about learning to let people meet you halfway on things. I've had to unlearn some aspect of going the extra mile. In some situations, that's actually not the right thing to do—not just pragmatically, but spiritually and philosophically. That's something I'm still unlearning.

Jackson: (1:37:56) I don't know that these are at odds, but you have lots of great advice about being good at asking or allowing people to help you. At least on the surface, that could be a little at odds with the halfway thing. How do you think about that? You seem to perceive yourself to be quite good at asking.

Mario: (1:38:16) I think you have to go above and beyond when you're asking. But when you're being asked for something, people sometimes want you to go 90% of the way. I think that's a place where you can learn to hold your ground a little bit more.

Jackson: (1:38:37) Holding your ground is a good mental thing to hold on to. You also said, "Most products people contend have taste show no sign of true deep quality. They simply encapsulate the aesthetic preferences of a high signal group. When someone says this, better to think of it as someone telling you, I am this kind of person." If people want examples, you list all the things you use. But what is a sign of true deep quality in a product?

Mario: (1:39:09) Generosity, meeting the user where they are. 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 for your audience. It wouldn't make sense for me to start every piece talking about what technology is or what software means, but I do think by and large there's not a lot of generosity in product and in writing. That could be as simple as having a really beautiful empty state or onboarding. I think there's more to be done in that.

Jackson: (1:39:54) Even those last two things you said, Silicon Valley claims to be obsessed with. We want to build delightful products. Perhaps this is your point.

Mario: (1:40:04) Delight often just means there are really nice gradients or a really great dark mode. I do think there are people who care about this deeply, and there are obviously many beautiful products. But we also set in place a set of really strict heuristics at various moments of what we think good is, or how certain things are supposed to work. It seems to take a long time for us to interrogate those anew. Even just now, we're finally seeing some different form factors around consumer electronics and hardware emerging. We've been really fixed on a certain form factor for a really long period of time. 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 that it has some of these qualities that I'd want to tie myself to too much.

Jackson: (1:41:03) You wrote that you spent nearly a year studying what may be one of the most important companies of our era. I'm curious if you can give us any kind of teaser what that might be. It's okay if not.

Mario: (1:41:17) I think it will be obvious what the most important companies are right now in the world. 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. Hopefully, I can write a piece that captures one of those companies at a really deep level of fidelity.

Jackson: (1:41:45) Are you still working on the novel? As if there were not enough things, how's that going?

Mario: (1:41:51) It's going quite well compared to a year ago. I started working with an incredible editor who is one of the most acute readers I've ever met. They have been able to diagnose some of the things that I felt were wrong with it but couldn't put my finger on. I've learned a huge amount about structuring things, and why certain things work and certain things don't that I was missing before. 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. That's the part I feel a bit stressed about. I can now see how to get there for the first time, but it's not going to magically happen. Who knows how long it will take.

Jackson: (1:43:09) A great editor can be generous in the way you're talking about. The same with products. People often talk about things they most regret. I'm curious to flip that for you. Is there anything that comes to mind that you're most glad you did?

Mario: (1:43:24) The most obvious one is going to one of my best friend's birthday parties and meeting my wife. That is certainly the best thing I ever did. The best professional one is undoubtedly starting The Generalist. If I have to go back a little further, I would say taking a night school class at NYU for fiction writing while I was working at a law firm. I began as a 22-year-old to imagine that you are supposed to be writing every single day, not just being a good writer in school and writing when you feel like it. That forced a habit. I would not have been able to do The Generalist as well if I hadn't started taking it super seriously at that point.

Jackson: (1:44:18) Sort of becoming the person you imagine yourself to be. You mention your wife, and 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 wildly opinionated and probably a banger. How does your wife make you better?

Mario: (1:44:44) I almost disagree with the premise. She makes me better in many ways, but that's too focused on me. She's just incredible in every way, and not because she does something that changes my chemistry. Kate Hall had a really good post saying she liked a lot of my observations, but totally disagreed with this one. People feel differently, but for me, it was just so obvious and effortless. I'm very lucky in that sense. She makes me better, but she's just miraculous in her own sense.

Jackson: (1:45:28) I have one last thing, a pair of quotes. 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 inevitability. I would never have thought of running a newsletter, and yet, once I'd begun, it was strange that it had taken me so long. So many of the best things that have happened to the publication, to my investing, to my thinking, have arrived from directions I did not anticipate." Then a quote from Oscar Wilde, who I think Byron brought up with you in that joining Hummingbird piece. Wilde says: "If you want to be a grocer, or a general, or a politician, or a judge, you will invariably become it; that is your punishment. If you never know what you want to be, if you live what some might call the dynamic life, but what I will call the artistic life, if each day you are unsure of who you are and what you know, you will never become anything, and that is your reward." How is this reward of not knowing, of being a generalist, going?

Mario: (1:46:35) No complaints so far. I think that remains one of the truest things I believe about myself: 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, I'll always love stories, and I'll always love studying these fascinating, incredible people that tech has an abundance of. But I try not to get too attached to a certain form factor. I hope I surprise myself in a few ways in the years ahead.

Jackson: (1:47:12) Onwards. Thank you very much. That's all I got.

Mario: (1:47:14) Thank you.

(1:47:15) Thanks Again to Notion

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