38: Molly Mielke McCarthy - The Art of Peopling

[00:00] The thinking beyond Moth at the beginning was like, I saw that there was just an abundance of capital for people that were credentialed and legible and went to Stanford, ex-keep mind, whatever it is. But there was another type of person that wasn't following a linear path and wasn't legible, and they were just consistently underpriced. There is a long period of time. [00:17] before they've built and shipped something successful. When, if you met that person, you're, [00:22] I think you could still see in their eyes that there's something very deeply special about them, if you got to know them.

It might take three months. It might take three months. It might take a year. But it is deeply worth it, I think, because they're the ones who you really can change the trajectory of. And... [00:37] from a purely financial perspective. They are underpriced. My core belief is that magnetism [00:43] is a byproduct of authenticity and just like living as you were intended to on the thing that you were meant to. I think I'm a really strong believer in the pure concept of vocation, meaning that like there is a right thing for people to be working on.

I think it's really hard to be agentic if you're not present. If you're not present to the reality of the world around you and you're not present to yourself and what you're feeling and what you want and what you need, you can have something that some people might call agency, but I don't know if I would [01:13] authentic to you. It's like it's making moves in the world that are moving you in a direction, but is it even the right direction? I guess part of my definition personally of agency is I would hope that it would be something that is true to you and true to where you should be going and feel is destined for you to go.

Welcome to Dialectic episode 38 with Molly Mielke McCarthy. Molly is an early stage investor at her fund, Moff Fund, where she focuses on finding special, illegible, commercial, [01:41] and mission-driven individuals, or people she likes to call moths. [01:46] She calls them moths because they're a little less obvious than the proverbial butterfly, and yet... [01:53] She is so drawn to them and she thinks that in many ways they tend to be undervalued early on. Molly describes her professional and creative lives as a mix between peopling and making, and she spent her career doing just that.

She studied film at NYU Tisch and computers and creativity at UCLA, and during school and afterwards spent time at a number of technology companies, including Figma. [02:15] Notion, The Browser Company, Stripe Press, and others, and was a Sequoia Scout before deciding to go out on her own and focus on full-time investing. Molly brings a creative and intuitive, and yet pragmatic approach to all of her work. And I think her creative background clearly influences both the people and the types of companies she tends to work with. That said, at this stage, she's almost entirely focused on the people side of investing and her work.

[02:45] what makes the special mothy type people that Molly works with so enamoring to her and so compelling from an investment standpoint. We also talk at length about the way she's been able to tailor the job of early stage investing specifically to her so she doesn't experience FOMO or distraction or try and compete on somebody else's game. [03:03] Molly's also an incredible writer, and one of the things I love about her writing is she's constantly rotating between introspection and action, a theme that's covered often on this podcast, and we talk about the way she's evolved her relationship with self-knowledge.

I hope this conversation inspires you to draw closer to the people who you find special, to know yourself more deeply, and to, as Molly has done, yield to your vocational and creative calling, whatever that might be, and however unexpected that might be. [03:31] whether a grand change or even to settle in more deeply to the thing you know you're meant to do. [03:36] Before we get into the episode, I'd like to thank Notion Dialectics presenting partner. [03:41] Notion is a creative workspace for your life's work. [03:44] And it's used by...

[03:46] all kinds of teams from small startups to large organizations to collaborate, work with, and get leverage from AI. [03:54] and ultimately turn their ideas into action. [03:57] Notion spent years creating a robust and yet remarkably simple tool for anyone collaborating on words, ideas, databases, and more. And now they continue to make the product even more powerful thanks to AI. And what I love about Notion's approach to AI is that it's a very powerful tool for anyone who's collaborating on words, ideas, databases, and more. [04:12] is that they're focused. [04:13] not on delegating all of the work, but instead on giving you more leverage to focus on the important stuff, the creative stuff, the collaborative stuff, [04:21] and automate the rest, whether that be with their agents that can run inside Notion workspaces, or even just simple AI tools that can pull out patterns and ideas from what you're writing.

I use Notion to both prepare and to review dialectic conversations afterwards, and it gives me so much leverage for thinking high-level about the ideas that matter, [04:40] that I cover on the show. [04:41] If you haven't tried Notion, you can check it out at com slash dialectic. [04:45] And whether it's your first time or you've been using Notion for years, I hope you're inspired to make something. [04:51] I'll link to Notion in the description, as well as all of the links and references that might be helpful for this episode with Molly.

[04:58] As always, you can find more information, a full transcript, and all those links at fm. And this episode is slash MMM for Molly Mielke McCarthy. [05:10] With that said, here is my conversation with Molly. I hope you enjoy it. [05:14] Molly Mielke McCarthy, we are here. Thank you for doing this. I'm delighted to be here. We're going to start with something I know you know a lot about, which is people and particularly exceptional people. [05:25] I'm going to start with a quote from you. But what I do know is an exceptional person when I meet one.

[05:31] I like to say that Moth Fund is sector agnostic, but in no way person agnostic. I'm uninterested in investing in anyone but people who I'm positive will mold the future to their liking. [05:42] Mm-hmm. [05:43] How do you know an exceptional person when you see one? [05:46] Or meet one. Mm-hmm. [05:48] I think it's more feeling-led than anything else. Something about them that creates this feeling of, like, I've never met anyone that has this combination of qualities and experiences and characteristics before. Yeah. [06:01] And then I think there's something about [06:03] them pursuing excellence and actually attaining it.

[06:07] that I like to look for, some kind of flywheel around competency that I think is hard to find. [06:13] I think one of the underlying [06:14] Premises to... [06:16] Moth Fund and my approach to people is that I think competence is hard to find and storytelling can be taught. And I think that that is something that guides a lot of where I spend my time as someone who can help with storytelling. [06:28] How long does it take you to... [06:30] Like, is there a minimum viable threshold of time with someone or questions, things you need to know about their background to be able to kind of like get to that feeling?

Yeah. [06:40] Three months. [06:41] Really? Yeah. It's very clear. That's like you've done a lot of this. I've done a lot, yeah. I think anything less than three months doesn't give me an accurate representation of their slope of growth. [06:54] And I... [06:55] care a lot about that. I think... [06:57] So much of my job as an investor with the strategy that I have is to find the strangest, most spiky people and then see which ones start to like gain momentum and take off. [07:07] And what I like to see is they're getting better at all of these things that they were previously not good at.

And they're tackling things that were previously holding them back. And I think three months is a... [07:16] pretty accurate representation of, you know, if they've made no progress in three months, and they're probably not going to in the next three months either. And, you know, [07:23] I think it's being open to all the different ways they could change, too. It's not necessarily just company progress, but it might be a personal, you know, milestone in how they're thinking about things or whatever it is. [07:34] Typically, though, I know people that I invest in for minimum a year.

But three months is what I look for to really get an accurate barometer before I can really say, oh, yeah, they're exceptional. I don't know as much. It's hard to say. Does it have to be... [07:50] like first-party data. Like, let's say it's someone you trusted... [07:54] you know well, and you trust. Yeah. And they have a history with this person. They've known them for a year. Yeah. And you've only known this person for two weeks. Like, can you substitute that? [08:04] You can, but I think it's at only like half as...

No, 0.5x my own experience. That's what I'm going to say. No one knows like me. Yeah. It's not even necessarily that. It's no one knows what I'm looking for like me. Totally. Right. I think I just... I want to see that... [08:18] The people that I really respect in my network are impressed by them, but I also want my own evaluation because I think that it actually tells me a lot about the person that I'm trying to get to know and the person that spoke highly of them. [08:31] I think that there's a lot to be gleaned there.

And if you just take it verbatim that I'm not actually developing my own taste. One thing that has continued to come up in the taste stuff, both in conversations I've done for this and in general, is like... [08:43] a very core product product. [08:45] or input to taste is eating lots of food. It's like so easy to like get lost in the sauce of ideating about it. It's like, no, you taste like, let's not let's not forget what that literally means. You mentioned spiky spikiness. That's something that has come up a lot in your writing.

And I certainly resonate with and other people I know who [09:05] care a lot about people talk about you, you describe it spike as I want to understand what a person's greatest strength is and how that functions doubly as their greatest weakness. Um, [09:14] Yeah. [09:15] I think that's like a common trope and... [09:17] It's certainly poetic and Bradley feels right to me. [09:21] I'm curious how it like... [09:23] how it sort of actually shows up and how you learn to see that maybe, especially in this three month period where, um, [09:29] you're getting to know someone.

[09:31] I think it's... [09:33] Trying to understand what their core competency, like what is almost like their dominant leg that they lead with. [09:42] how does that make their other leg weaker basically is what I'm trying to see. And people usually show you by the [09:49] place, basically just how they allocate their time. I think that most people are much more comfortable spending time on the things that they're good at. And if you look at the stuff that they're neglecting, it gives you a lot of signal on what's really going on here.

But I should insert like a lot of these people, maybe not all of them, but many of the people you spend time with and eventually invest in, you meet when they're very young. [10:12] Definitely. And so they're, [10:14] not well-rounded by default. Like they're probably not doing their laundry or whatever. Yeah, absolutely. Versus maybe analyzing on a 35-year-old, it would be different? Yes. Well, I think that it's... [10:25] For the young people that, you're right, I spend most of my time evaluating, I think that it's trying to [10:32] Okay. [10:33] Understand their growth trajectory over those three months and that I can accurately predict what it'll look like in 10 years, whatever it might be.

And I think that that is something that people actually give you a lot more signal on than people. [10:44] you'd expect. I think you just have to [10:47] listen to them a little bit closer. Like, what are they telling you? What are they not telling you? And how honest are they with themselves? I think... [10:54] I've never set out to look for people who are like the most... [10:59] in therapy speak or whatever it is, but I am looking for a certain kind of person that I think... [11:04] fits my [11:05] Archetype of how I could help them and I think it is like I said the one that I [11:09] Spikes in competency, but maybe storytelling is more weak.

And I think that's harder to find. And I call it a moth. It's a quirky, quiet missionary. But I do think that you have to also, when evaluating young people, have a lot of humility, because I've been wronged as many times as everybody else. And I think it's it's realizing how often our own. [11:32] judgments of ourselves and how we see the world cloud our vision on a person in front of us and i think that that's [11:37] That's a really interesting pursuit to me that keeps me motivated to keep showing up.

It's like figuring out the person that I'm evaluating, but also figuring out what am I learning about myself in this process. [11:48] Yeah, what am I even putting into the observation? One of the things I love in... [11:52] in that classic Graham Duncan, like what's going on here with the human is just like the ways that [11:58] you as an interviewer or as an investor might be like totally warping the context a person is in. Absolutely, yeah. And thus you're actually getting like a wildly unreliable perspective on them. [12:17] paragraphs that I thought were interesting in this context that I'll read quickly.

First, you say the main commonality tying all my friends together is how incredibly individual we are. The idea that each of us was designed to work on specific things in the world that we must first do the work to reveal to ourselves. And in many ways, this is the opposite of the Silicon Valley thinking that surrounds us, which sees humans as interchangeable workers regarded most highly for extremely uneven development. [12:44] Precocious spikiness is what gets you noticed in the world of startups. So it's no surprise how many competitive people become razor sharp.

[12:51] functionally turning themselves into tools tailored design to solve specific problems. [12:57] But obviously that's no way to live, or at least it's definitely no way to live long-term. All of my favorite people contain all manner of superfluous, silly, and soft parts that make them so much more than a tool. [13:10] Beautiful writing. I'm curious how you square this because... [13:14] and maybe this is not quite the point you're making, but it does seem sort of like you're saying spikiness is a trait. [13:20] maybe even like a bourbon, [13:22] Yeah.

That... [13:22] is best reserved maybe for founders and like while the rest of us aim for generality or something, or am I being too prescriptive there? [13:29] No, I think that pretty accurately slides me down. I think that a lot of the people that I bet on... [13:36] have a very specific reason that they want to do the thing and it's very close to their heart. [13:40] And their brain, and they care a lot about it, and they feel the need to... [13:45] Almost. [13:46] exercise this vision in their head but i think that the the people that um [13:52] I find myself most gravitating towards are the ones that are actually more focused on living well.

And... [13:58] I think for better or worse, like I both really deeply enjoy serving the people that have a mission to work. [14:06] embark on, but they're not necessarily the ones that I want to spend all my time with. They probably don't have the time to hang out with you anyway. [14:19] there are probably people who at the beginning of their career started off as very spiky, maybe even to take an extreme like a Mark Zuckerberg or whatever, and who have gradually figured out how to add... [14:29] color or resolution to that picture as it's needed.

Totally. Um, [14:34] And then it's also a question of, like, I wonder if you got close to him. [14:39] have his spikes dobbled a bit. Yeah. Yeah. [14:42] Or have they remained razor sharp and he's just filled in everything else with having money and help. Right. It's funny. The way I've used spikiness to describe people... [14:52] is I'm almost, I find, 'cause I always say I'm kind of, I like to spend time with spiky people, but it's not quite in the way you're describing it, which is this like very one, almost like one dimensionality.

- Yeah. - I like people who have several spikes. [15:06] But I like those people much more than I like people who are, like, very well-rounded everywhere. Yeah. But I don't like people with one spike. Yeah. [15:13] That is a very good point. I actually think in practice, people that I spend the most time with are T-shaped. I think that the ultra-spiky, one-dimensional spike are typically just very young. The ones that are a little bit older, they turn more T-shaped. [15:30] whatever polygon shape it is. Yeah, Brie has this metaphor of the fork shape.

Yeah, that's good too. That's kind of what I'm... Yeah. Totally. [15:39] You mentioned moths and the notion that you're... [15:43] and we'll talk more about this later, but you're kind of working with people who... [15:46] aren't totally legible. You also described... [15:49] Magnetism is a really valuable trait or something that you're looking for. What makes people magnetic? [15:55] And particularly maybe how do you think about that in the context of people who might not be the most legible yet? Yeah, yeah, yeah. [16:01] My core belief is that [16:03] like magnetism [16:05] is a byproduct of authenticity and just like living as...

[16:09] you were intended to on the thing that you were meant to. I think I'm a really strong believer in... [16:14] the like pure concept of vocation, meaning that like there is a right thing for people to be working on. Um, and, um, [16:22] I just think that magnetism is something that, like, there's the version of magnetism that is large scale and something that you would... [16:29] you know, ascribe to the hottest startup or whatever it might be. That's less interesting. That's like a commercial magnetism that is produced by a team.

Then there's like a smaller scale magnetism that like one person has. And that can either be charisma or it can be them actually just being deeply, deeply authentic. And I think charisma is usually the version that is actually a bit more. It's a skill. It's also a bit more performed. Right. Authenticity in that form of magnetism, I think, is much more durable. And it doesn't drain a person in the same way a performance does. And I think it's also just... [16:59] innately and quietly and deeply attractive to the right people and not to the wrong ones.

And so I think that that's the kind of magnetism that I'm looking for at the earliest stages. [17:08] You could totally imagine how a fairly introverted person [17:13] Someone who's kind of understood in the world and who's very nerdy could be very magnetic in a specific way. Exactly. Yeah. Because get them going talking about their favorite part of the nerd world, and then they... [17:24] people just like them are like swarming and they're like, you are one of me, one of us. Yeah. So it kind of goes back to your competence thing too, which is like radical competence or knowledge or curiosity or whatever is, it's like you can catch the thing that makes somebody's eyes light up and they can go really deep on it.

It's quite, [17:38] It's huge. [17:39] It's very compelling. And it's also like to the wrong people, they just they don't even pay attention. They're like, what are you going on about? But that they were never the people that you should spend time with anyways. You mentioned trajectory. A couple of the quotes. I learned a lot about how to evaluate smart people by how they've evaluated me. [17:57] Many of the investors that bet on me made it extremely explicit that they aren't betting on who I am now, but instead betting on the future version of me that sees success from sticking to this.

[18:06] And then you say discernment can be glimpsed in their reflections. They should have to exchange their innocence for wisdom, not just experience. [18:13] I think it's really, really powerful. [18:16] How do you start to see the... [18:19] the potentiality of that, particularly that last bit, which is like, [18:22] being able to trade... [18:24] Innocence for Wisdom. [18:26] Hmm. [18:28] Everyone trades innocence for experience. Totally. Stay on the track. Yeah. I mean... [18:36] I think that it usually just comes down to actually... [18:40] mining the wreckage of your experiences and the winds of your experience and learning things from it.

It's usually just self-reflection is what turns it into wisdom. But it's self-reflection that extends beyond just yourself. It's not just about, like, what is it about me? It's also what is it about myself? [18:55] the world and what is it about the other people that I can learn from these experiences. And I think that that is something that, um, [19:02] is the kind of help and support that I like to provide to founders. Is this kind of quasi-cognitive? [19:09] coaching relationship where we're doing just that basically. Like how can you grow faster in the direction that you want to grow?

[19:15] I find that to be an endlessly interesting question. It's much less constrained to like, how can you build this startup? Well, [19:21] Maybe you shouldn't be building this startup. But that's the thing we should be talking about, not what is the next product to build. Yeah, getting you closer to the vocation thing, too. You also talk a lot about discernment, which I think is really close to this. Yes, yeah. [19:36] Um, [19:37] Which is, as you say, not just seeing yourself clearly, but seeing... [19:41] the context and the world and the other people and the situation and all of it clearly.

And like also knowing... [19:47] It's some line somewhere that I can't remember, but it was along the lines of like being able to like drop the thing and not just like stay in the inertia of it. I feel like that's part of this. I discernment is like the the ultimate goal that I hold up in my mind in. [20:03] in really everything I do, but especially in [20:06] my investing and in what I call the peopling part of my career, which is like, how can I pick people, support people, help them grow.

But like in doing so, it's about [20:16] Being discerning about which ones I pick. Yes, that's the obvious, like, what is the investor relationship? But I think it's also, to me, it's really about, like, being discerning about, like, how I help them. [20:25] Like, am I really helping them in the direction that they are meant to be helped? Am I being very responsive to this person and discerning about the things that they're saying? Like that, that's... [20:35] just as interesting as the picking, I think. And I'm not saying it's going to change the outcome of the startup, but I am saying that I think it's a deeply different relationship that can change people's worldview a bit and how they feel about their work.

And I think that that's very impactful at the beginning stages. Yeah, there's a stewardship of that position that acknowledges – [20:56] Yeah, in many cases, it won't matter that much, but in the world where it actually very... You are in a position where you could significantly inflect somebody's... [21:05] situation, life, whatever, direction. And it's like almost carrying that weight. [21:11] Like, um... [21:12] Thank you. [21:13] understanding the weight of what you're carrying, maybe. And trying to wear it lightly, too. I think I've definitely gone through phases of being like, this is way too much responsibility.

And I'm like, I'm overthinking it. It's not that deep. But I do think that there is something about just... [21:27] accurately reflecting back a person at the beginning stages of them working on something that could be their magnum opus that is like very, very, uh, it is deep. It can be very deep. Another quote you say, discerning founders do everything they can to stay rooted in the present. [21:42] forgiving themselves a thousand times so they can continue to see the bigger picture and act. [21:48] How do presence and agency [21:50] relate to each other.

[21:52] Hmm. [21:54] I think it's really hard to be agentic if you're not present. Like, if you're not present to the reality of the world around you, [22:02] And you're not present to yourself and what you're feeling and what you want and what you need. [22:09] You can have... [22:11] Something that some people might call agency, but I don't know if I would, because it's not very authentic to you. It's like it's making moves in the world that are. [22:18] you know, moving you in a direction, but is it even the right direction?

I guess part of my definition personally of agency is I would hope that it would be something that is true to you and true to where you are. [22:30] should be going and feel is destined for you to go. You have another quote that is along these lines. You say from the outside, agency is often misinterpreted as ambition. But I learned through observing these two types of people that they're actually quite different. Ambition means you're motivated to play games that others have already created in the world. Agency means you're driven to play a game of your own.

[22:52] I guess maybe I have two questions, which is like one – [22:54] piggybacking on the last thing, like, [22:57] The presence thing is so interesting to me because in part, I think there's some intuition that like agency is kind of about knowing what to do in the future. It has more of a future orientation. I guess the other part of that is just like. [23:07] How do you think that works? [23:09] that distinction between ambition and agency is, [23:12] affects how people should maybe interpret the classic phrase, you can just do things.

[23:21] Yeah. [23:22] I think that so much of like agentic people, so many of them are [23:27] actually just deeply experienced just doing things and they know that the possibility is there and then they become more in alignment with like what [23:36] do I want to do? Like, what is the game I want to play? Because they have a high feedback loop. They have a high feedback loop. They have been just doing things for a while. I think ambition is usually more like, you can just do things, but do things that are on a tracked path that will get me status, prestige, whatever it might be.

Actually, it's funny, because that was my... [23:57] kind of core thesis to Moth at the beginning was kind of this idea of the difference between agency and ambition and wanting to target more the... [24:04] people that were acting from agency because I thought that they were undervalued. I think that over time I've realized that it's, [24:11] It's muddy. It's not that clean. It's nice to make a neat distinction on the page. But I think in practice, like ambition is often deeply interwrapped with ambition. [24:23] agency. I think that we're, you know, status-minded creatures and like there's, it's not always clear what is a game that someone else said that is actually the right game for you versus one that do you have to make it all from scratch.

I think part of realizing that I was a little bit, um, [24:40] Black and white in that thinking is realizing that like the way that I see the world is as someone who is much more of an individualist. [24:48] I really care about [24:49] doing everything my own way. Right. And like, I would never want to play someone else's game. But that's not true of everybody. [24:56] In fact, most people do not feel the same way. And there are bonus points for being purely original, like being the most special snowflake.

Absolutely. Yes. And I think it's a beacon for other people. They like to see it, but I don't think it's necessary at all. I think there are good... [25:11] stock games that you can play that are actually the right fit for what you want to do. Totally. And by the way, there's a huge gradient. Like I suspect the other part of this that's interesting, even in the time you haven't been investing for that long, but the time you have, like the Overton window on... [25:27] unique or original or off the beaten path is moving.

10 years ago Y Combinator was pretty, [25:35] not ambitious. It was like weird. And now it's obviously like it's closer to Harvard. Right. Absolutely. Yeah. And so like that, I guess is always gradually shifting too. Yeah. Yeah. [25:44] And it [25:45] I think that that was a lot of the... [25:47] The Thinking Beyond Moth at the beginning was like, I saw that there was just an abundance of capital for people that were credentialed and rentable and, you know, [25:56] went to Stanford, ex-keep mind, whatever it is, but there was another type of person that wasn't following a linear path and wasn't legible, and they were just consistently underpriced until they had actually built something that proved how good they were.

But I was like, there is a long period – [26:09] before they've built and shipped something successful, when if you met that person... [26:14] I think you could still see in their eyes that there's something very deeply special about them, if you got to know them. It might take three months. It might take three months. It might take a year. But it is deeply worth it, I think, because... [26:25] they're the ones who you really can change the trajectory of and, and, [26:30] from a purely financial perspective, they are underpriced.

Until they have shipped something, like real. One last thing on agency... [26:39] and maybe this point is a little bit... [26:43] over discussed, but you first of all, you have a line. You say, I want all of us to know just how much ownership we have over the future, which is a really beautiful way of kind of framing the positive side of agency. You also have this articulation that I thought was quite interesting, and I think it's fairly old. So I'm curious for you to reflect on it is. [26:58] like the inputs to agency along this notion where I was...

[27:01] referring to when I started the question, which is like, can agency be improved, particularly in adults? Yeah. Or is it sort of fixed? And you describe it as the hook, the catalyst and the sustainer as these like frames of [27:12] inputs for increasing it. I'm curious, like, one... [27:17] Do you think it holds? Would you amend it? And then more broadly, as you've continued to do this, have you... [27:24] Do you have any updated sense of what types, particularly in the sense where somebody can go from... [27:30] not that agentic to somewhat agentic, which to me seems like the big one.

Cause once you get into the agentic loop, it starts to compound. Yeah. I think I was very idealistic when I read that. [27:41] 2022 or something like that. Um, [27:44] I think that there's some truth to it, but I think it is... [27:47] pretty capped. I think that like people can be inspired by someone else's story. [27:52] try something out, and then be in a more... [27:55] like agentic filled [27:57] other people environment and get to a slightly different baseline. But I do think it's hard. I mean, I think it's, [28:05] My counter argument is just seeing how people from other environments, if they're not young and they, you know, say, decide to move to the Bay Area and get into startups like it is quite hard if you're in your 30s or something to to change your attitudes about the world.

[28:22] And [28:23] I think it's definitely possible if you are open-minded enough, but I think... [28:27] very rarely are people. I think I, again, a piece of like self-reflection from writing that piece a while ago is like [28:37] I... [28:38] grew up in a very open-minded environment, and it was, like, full of hippies that were constantly thinking about how can we change the world, and it was more about constantly... [28:49] Figuring out what was wrong and figuring out the solution. And while that is completely different, really, than the approach that startup people think about things.

It has the same tenor of, like, let's just do things. Except one of them is going to protest. Very California, in a way. Exactly. No coincidence. Yeah. You didn't grow up in Silicon Valley, but you grew up in a... Very hippie, small town. Yeah. But I think that it made me think that all people have a higher level of agency than... [29:15] I think that they do. And I think I've also just chased environments where the people are agentic and interesting and... [29:24] unafraid and original. And I... [29:28] have found myself constantly trying to find those.

I mean, I think I was drawn to film first because I was around people like directors who were building a world. [29:37] And in the same way, once I got into tech, I was like, oh, these founders, they are also building a world. Very entrepreneurial, both of them are. Exactly. Yeah. And there was something deeply interesting about both of those and compelling, and I wanted to help and be a part of it and help them refine and calcify and grow it. But I do think that. [29:54] Like I said, I think that I've just been lucky.

Like, I've been in environments where it has been encouraged to be ambitious and to do things and to take risks. And I think a lot of this... [30:06] Learning has just been... [30:07] being in other countries and being, you know, with visiting friends, home environments, and just learning that it's not at all like what I thought the rest of the world was. [30:21] thing on this note, maybe somewhere where you're, uh, citing David Brooks describes this as adhering to the theory of maximal taste. And you have this little excerpt, which is this theory is based on the idea that exposure to genius has the power to expand your consciousness.

If you spend a lot of time with genius, your mind will end up bigger and broader than if you spend your time only with run of the mill stuff. The theory of maximum taste says that each person's mind is defined by its upper limit. [30:47] the best that it habitually consumes and is capable of consuming. [30:52] which again, I think still your, your main point stands, which is like on a relative basis, but like it, [30:59] There's something to that, though. There is something to that. Yeah. It's just probably only in the people that have already self-selected for agentic environments.

And then the ones that choose to, like, fill their mind with things that push the bounds are going to... [31:11] grow and [31:13] Yeah, it's interesting. I think I was thinking, maybe I talked with Bree about this as well, because... [31:21] We were reflecting on like these really impressive people when they're really young. And usually it's very clear when you're 20 or like, yeah, I don't know. I, I was not in an environment where like, [31:29] there were 15 year olds doing great startups and stuff. I mean, me neither. Yeah.

Right. And so I, I have to actually, like I went from a, I went from a, [31:37] And again, I don't know where the baseline was, but I learned from a world where you really don't know what gray looks like until you see it. Yeah. [31:44] And so that would be my one bit of hope on this note is like... [31:48] environments are really powerful. Yeah. And perhaps the real answer, the thing that you're pointing at is that most people are just, have never even gotten close to an environment that would allow them to like see how high the bar can be.

I think that's exactly it. Yeah. Yeah. And like the bar doesn't need to be, you know, just startups or just whatever your chosen profession. It could be in a completely unrelated field. Like I think competence is impressive and magnetic no matter what it is. You can just kind of feel it. Right. And I think even being around like an amazing lawyer or something in their business [32:18] environment in their zone of genius. I think that that would be also like, wow, you can be like that. But I just think that- But you'd have to see the process.

You have to see it in person. You have to be around it. You have to absorb it. And you have to see how they spend their time. [32:30] just who they are, how they relate to their work. And I think so much of... [32:35] My career was a story of like, once I got into tech, I was very lucky to be around excellent people. And having my bar raised so much in this field where I was seeing that, [32:47] I was suddenly given so much more autonomy and, and agency, um, [32:52] Than I had been in any other environment.

And so it was just, I was like, I'm never going to leave. But it is a story of this happening to me. And then me staying around because of it. Yes. Yeah. [33:00] Yeah, my sense is the process, like the garage door part of it is really important. It makes me think I was chatting with a friend this morning. There's a Jerry Seinfeld line where he says something along the lines of, all art is disguising work. [33:15] Meaning it's like, it's sort of like the magic trick. Yeah, yeah, yeah. And I actually think to your earlier point, like people...

[33:24] are exposed to great things, but it looks easy. [33:29] And so maybe the thing is actually getting to see... [33:34] Like the process. I think it's a process. Yeah, because, I mean, everyone can look up a Mona Lisa or, like, any given... Or even a great film or a great song. Exactly. But you don't see the slugging. Totally. You don't know what went into it. And you don't know, like... [33:47] how the person making it was feeling about their work through the whole process. What were they doing? Were they micromanaging?

Were they going crazy? That's the stuff that makes me like, this is the level of sacrifice that a person who really cares about what they're doing puts in. Yes. Yes. Yes. And also, I don't know. I just wrote East of Eden by John Steinbeck, and I'm reading these letters he was writing while he was writing East of Eden. And it's [34:13] So, like, honestly, the main emotion I had is like, oh, he's just like me. Like, he's basically just like, some days he's like, I'm a genius. I'm so good at writing.

And other days he's like, this sucks. I suck. And so I think there's a bit of that. There's almost an accessibility of it, too. Absolutely. Seeing that they're human, seeing that they, like... [34:32] Yeah, the peaks and the troughs, really. I do think that that's actually a huge part of it. Right. It humanizes it for people of like, wow, excellence can look like not always having a good day, but still just showing up every day. Right. Right. Exactly. Yeah. [34:45] One of the more important things [34:47] traits in my view, and I think you express a similar view when it comes to early stage in any kind of investing, but maybe especially early stage because less obvious is commerciality.

[34:57] You have an essay called The Lost Charisma of Capitalism, which I thought was really great. Kind of like describes the essence of this. A couple of quotes. First, I became obsessed with understanding the defining aspect of the successful entrepreneur, their commercial aptitude. And then commercial instincts are the result of exposure, perhaps even more than inherent talent. The latter I'm particularly interested in. Maybe it's kind of like the agency thing. Yeah. [35:21] I think... [35:23] Like when people talk about commerciality and maybe it's also worth being more specific about what we mean by that.

I'd be curious for your definition. But people talk about like, oh, it's like they've been they started their first business when they were sick selling lollipops. Like it does feel like it's more of one of these innate things. And yet you're saying. [35:37] or at least you were saying at the time that it was, um, largely a product of exposure. Yeah. So yeah, maybe, maybe first I, I love your perspective on commerciality and why it's so important and to that threat on exposure. I think I define it as like knowing how to capture the value you create and having a hunger for it.

I think, um, [35:55] Highly commercial people typically see the world in terms of money and like where they [36:00] it flows, how it can be captured, [36:03] They just... [36:05] understand the world that way. It's almost like their version of math in their head. And I do think that that is... [36:12] Something that some people are just... [36:14] born with and do have that like [36:17] the quintessential cliche entrepreneurial lemonade stand streak. And I think that that's really special. I think also though, [36:24] There's many tales of people growing up in families where somebody else in their family was more commercial and they learned it from them.

And I do think it can definitely be. [36:33] the kind of thing that, you know, you join an early stage startup, you're around a highly commercial CEO and you pick it up from them. You're like, oh, this is how it works. This is how they made money. Right. Like I saw the hunger in their eyes. You've seen the matrix almost. Exactly. Yeah. And then I think that they just start to see those opportunities again. [36:50] as well out in the world for themselves. And so I think that it really is just like a lens that you can acquire.

Some people are born with it. Other people learn it from other people. But I do think that it's, it's not as complicated as people think it is. I guess I say that as someone who was like, very not commercial, and grew up with like a very anti money background. And then, [37:13] came into tech and now working in venture capital. And I think like, uh, [37:17] A, you can definitely just feel it when you're around people who are commercial. There's a hunger and desire there that... [37:24] is not just ambition it's also just like their view of the world but also then you just you start to like even myself i would just start to look around and be like i can kind of see like these people have it these people don't these these are the kinds of opportunities they look at and then i would see something out in the world i'd be like if i were that person i'd be interested in that commercial opportunity but it it's

[37:44] I actually think it's a lot easier to train than agency or anything like that because it's less risky. [37:50] It doesn't necessarily mean that you're going to... [37:52] start the business. You're just seeing that a business could be started. [37:56] Right. Maybe another piece that... [37:59] the less commercial people might react to, or anyone would be like a little bit of a, in the negative, like a griftiness or something, or transactional nature. I love this from you. You said, most people do want something from you. It's just on what time scale.

Their urgency is what dictates whether the experience will feel good or bad on the receiving end. After all, being transactional on the scale of a human lifetime is how most productive partnerships are structured. Can you talk about like the specific process [38:27] positive sum [38:29] bent on the commerciality that makes such great entrepreneurs? Oh, I think it's just they... [38:35] are not looking to extract value right now. That's the main difference. People feel it. It's just patience. It's just patience. They're seeing that there's something interesting. They are drawn to... [38:47] you, like there's some kind of kismet to the relationship, you, the commercial person and somebody else, and they understand that there's something special here and they're willing to wait around until it's obvious what it is.

[38:59] Hmm. [39:00] I think that most successful... [39:02] founders, entrepreneurs, they collect special people, and then they figure out how to slot them in. And I think that that's... [39:09] The same for investing, too. I collect special people, and then I see if it makes sense to invest in them. But I think it's a certain style of thinking that is very people-centric. And I think I was very surprised in my jobs how... [39:24] it seems like [39:26] the, [39:27] Style of thinking of like the leaders that I worked for was incredibly people centric in almost a way that was similar to being an investor, even though they were running an organization, it was completely different.

But they were still thinking in these terms of like I recruiting is basically the most important thing and making this business. Right. [39:44] grow and flourish and that requires talent and i think that that was really interesting because i [39:52] was interested in thinking in a similar way of like, how can I find special people and support them in their, [39:59] growth, really. [40:00] But I wasn't interested in having them build my thing. So it was very clear that I shouldn't be a founder. [40:08] It's interesting. It makes me think of you have this thing about idea people and people people.

[40:14] And it's almost like [40:17] entrepreneurs probably need to start as idea people, but at some point at enough scale, if you're trying to build something ambitious enough, you kind of need to graduate into being people-oriented in terms of where your leverage comes from. I totally agree. And certain investors can split both ways. And many founders hate it when you say that. They're like, no, you can be idea-centric forever. And you're like... [40:36] Okay, sure. But your business is capped if you're thinking that way, because you're not actually thinking. I mean, maybe that world's going to maybe we're heading into a world where people let matter less.

But I'm a little skeptical. Maybe. Yeah, I'm skeptical, too. You have this frame on truth seeking people versus social cohesion oriented people. Yeah. [40:57] That was a while ago. Do you still believe in that? I'm curious for you to one, just like, [41:02] If that's another thing you've evolved your perspective on or if it actually kind of holds as a... I think it holds. I mean, it's more like a general thing that I'm constantly asking when I'm getting to know a person. It's like, do they lean more in one direction or the other?

Are they going to... [41:18] stay quiet even when they have something to say, but they think it'll disrupt the crowd. That would be more social cohesion. Are they actually just going to if they. [41:25] see a truth, they feel compelled to say it. If they [41:29] detect that someone's lying, are they going to needle at it? That would be more truth-seeking. And that's actually very, very useful to know, I think, specifically. [41:38] And I think typically most founders skew more truth-seeking. [41:42] So I think in this... So with that description, I think most people listening would be like, oh, obviously you only invest in truth.

Well, yeah, I'm truth-thinking, and also you should only invest in truth-thinking. I think in the thing you were talking about this, you actually... [41:54] describe Jeff Bezos as being a little bit more on the social cohesion? Yes. On the note of being a customer assessed. So I'm really curious about that. Well, I think social cohesion can look like just being an amazing salesperson. I think that the detractor, the not so good side of someone who's [42:10] very truth-seeking, is that they can actually [42:12] They can be very brash and very hard to build a relationship with.

They're very hard to be... [42:18] the level of smoothness that they need to do, like some kind of [42:21] sales that is actually [42:23] in one given industry. I think that... [42:26] Jeff Bezos is a good example. I think also people that have built successful software in vertical specific industries where they were had to build a lot of trust with their customers. I actually think like Dillard Field of Figma is a good example. They're not necessarily like. [42:40] just social cohesion, but they definitely have that skill. They definitely could bring it out.

And they definitely know when it's important to have it and play that card. And I think that that is not possible for a lot of the people that are so truth seeking that they can't even put that on. And that's more the skill thing is like, I mean, I'm sure that Jeff Bezos was, you know, fed up and saw in many instances that like, this is not true. This is what we should be doing. But [43:04] Did he have to name it and lose the deal, or was he able to put on the salesman's face and say, okay, I'm actually...

[43:10] It's fine. Like, we'll make it work. [43:15] Yeah, that is a much more interesting and useful orientation of it, I think, than the like [43:21] Obviously, you just want to be the truth seeker. [43:26] I think a relevant transition to talk a little bit about investing. On the note of commerciality, you wrote that you got advice from someone who suggested an investor is ideally a finance bro with a dash of Engelbart. [43:37] and even compared or observed that Neil Mehta feels like a very quintessential version of that. And you also noted that you didn't change yourself to become this, but it inspired some amount of more commerciality in yourself.

Yeah. Do you think you've grown in that direction? Do you think you've just gotten better at spotting it in the people, in the moths you look for? Like, what is your kind of relationship to commerciality? [43:59] Been over time. [44:00] I think that a framing that I've been using a lot recently has been, I think it was Will Manitis' who's like in the flow versus out of the flow investors. [44:08] I am most definitely an out of the floor master. Like I'm doing a very strange long term strategy that like really only makes sense for me.

I think that that is something I find deeply intrinsically motivating and I love. [44:21] but [44:22] I don't really experience FOMO. I think that so many investors are trying to be the in-the-flow investor, which means just being very competitive, really, and playing the game that everyone else is playing, but ideally winning at that game. And I have no desire to do that, like none. And so I think that the commerciality for me is like, [44:42] has always been something along the lines of, I want to be my weirdest, most original character.

[44:48] unique self attract people who see what [44:52] like for like, they're not necessarily like me, but they, they also understand how I can help them. And maybe some really feel misunderstood or whatever it might be. Right. And, and, [45:02] rise up and win that way and prove to everyone. [45:05] that investing in Moss and like, or you're on the back door or whatever, right? Exactly. It's good business. And like, that was, [45:12] That was the goal of my fund one was just like, [45:14] This is a proof of concept to prove out my hypothesis of the type of person that I think is undervalued and that I think I can successfully attract early.

Yes. And then the long term vision has always been to legitimize that archetype in the same way that like. [45:29] YC legitimized young technical talent, the Teal Fellowship legitimized dropouts. I think [45:34] Moss, which I define as this kind of quirky, quiet, mission-driven founder, is... [45:38] consistently underpriced. [45:41] In part, maybe because they don't see that commercial, but still are. Exactly. [45:46] Because I think that they're not, they come to their commerciality in a very roundabout way. It's almost like they care more about the mission, but they want the mission to be rewarded and to exist and to grow.

[45:57] And I think that is, it's very rare. You want to find people that are not just mission-driven, artist-driven, but they actually care so much about the mission. They think the mission is so big that they, of course, need to have the flywheel of making a lot of money, basically. [46:12] When it comes to finding people who are more commercial than you, which feels kind of important as someone who doesn't default to being very commercial, [46:18] given the context of everything we talked about earlier, and the fact that these people aren't that legible, like maybe in the three month period or whatever, [46:26] It's not going to show up in the way that somebody more...

[46:29] uh, salesy, it might be much easier to clock into the commercial part of it. Yeah. Like, what do you look for? How do you notice that? Like what you talk about, like looking for the sign of growth or trajectory or like, um, becoming resourceful or competent, but this feels like a slightly different thread. [46:45] I think it's often looking at actual proof from the past that I can do it. If it's, [46:51] so early. But then if it if there are [46:53] like in the process of building the thing and in the early days of potentially getting money for it it's like [47:00] How much do they care about that?

Are they actually good at sales? Are... [47:05] other people kind of coming in to help them get this thing off the ground in this way that is magnetic and gives you a hint at their ability to like sell too. I think that the ability to sell and being magnetic are usually kind of one and the same. But I do think it's. But sales comes in different flavors to the early. It totally does. Right. I think obviously like the flavor that I'm. [47:26] more interested in is the one where it's like almost mission-driven sales, if that's even a thing, where it's like the person clearly cares so much about the thing and is so authentic and doing the thing that they were meant to do that...

[47:39] of course you want to work with them or give them money or whatever it might be. Um, [47:43] But I do think that commerciality is actually something that you, at the end of the day, need to see proof of. [47:48] Most people who are verge on the mission-driven or authentic side, [47:53] Even if they're commercial, I find... [47:55] don't they have a really negative relationship to sales yeah tell me about it maybe i mean candidly you've even expressed this with fundraising yeah right like um [48:08] What is that process like?

Like, what have you observed either in yourself or in watching the founders you work with? Like, what is it like to sort of improve at the sales muscle in a way that... [48:18] So, [48:19] Like, does it mean becoming an authentic or can you do it in an authentic way? Can you improve its sales in an authentic way if this isn't your lean? [48:26] I think I've like, I only came to believe that you can still be authentic and be a good salesperson from seeing the founders that I back doing it.

And then being like, okay, it was cope. I should be doing the same. But I do think that, um, [48:40] this is one of the main things that I like help my founders with is like, it's so easy for me. [48:45] and always has been to be like, of course, you should be getting paid for this, you should be getting paid way more for this, like you should be [48:51] you know, advocating, like there's a certain level of like often the mission driven founder is the one that is a little bit more scared to put their thing out there or whatever it might be.

But they still have this hunger and desire to capture the value. And that's very important. But I do think that that is important. [49:07] It's something that it's very easy to be an outside observer and be like, clearly you should do, you should sell. It's hard to do for yourself. Hard to take your own advice. Very, very hard. Yeah. It took a very long time for me to finally take my own advice and get better at selling. [49:19] On the note of something I've certainly experienced in investing, and I think people don't know coming in and eventually realize, is the lack of feedback loops.

You write about this. You say that's because the craft adventure is not for people who derive their satisfaction from external indicators of progress. It's for people who find the development of their relationships and refinement of their internal model of the world to be motivation enough to keep going. [49:49] You as a founder should always choose investors who aren't using their investment in your company as a means to self-actualize themselves, which is hilarious. I think about that a lot. [50:01] Yeah, I'd love to hear you reflect on those two things. [50:04] that like need to self-actualize and like really I guess what I'm wondering about is like [50:10] how you and how one gets to this point of like, [50:14] total ease in the ambiguity.

Yeah. And maybe it's very different doing that at a big firm versus – [50:22] on your own. [50:23] I think in a big firm you have more things to distract yourself with. But I think at the end of the day, you're still left with the same question of like, it's not clear that I'm good at this yet. Right. Meaning you're saying you have like more artificial games to play that look kind of like a feedback loop. Totally. Yeah. But they're not. And you shouldn't confuse them. Like the game of investing is always going to be like, did you pick companies that made a lot of money?

Yeah. Like that is the... [50:45] best and worst part of investing in my opinion because I love the fact that it's so open-ended because it means I can do whatever I could take whatever path that suits me and that plays to my strengths to get there correct but as long as it's about making money as I get there and you don't know if you get there and so it's more the existential anxiety that you have to learn to deal with and I think that there's a certain amount of like I felt it a lot more the first time.

[51:11] three years or so [51:13] And then I think I got... [51:15] A bunch more markups, not that they're indicative of anything, but like early proof that there was something to my taste and that proved out my theory of moss. And that's what I was looking for from the very beginning. And I think from there, I think I just realized that I'm like, [51:29] What is the part that [51:31] of investing that I actually care about. And like, if I'm actually very honest with myself, I don't care about really anything except for the relationships with the founders.

That is the part that keeps me going. That's why I do all of this. [51:42] And [51:43] As long as I'm doing a good job at that and finding interesting people and developing deep relationships with them and serving them in their growth. [51:51] That's that's how I'm measuring myself, because I can like I can tell myself that it's like the rat race of fundraising or the rat race of, you know, [51:59] being known in the right circles. But I don't really care about that. And... [52:04] Like I said, I think I'm lucky in the sense that I don't find myself very impacted by FOMO.

And so it's more like as long as I can evaluate myself... [52:15] with my own metric at the end of the day and be like, I think I'm tracking, I think as long as I keep the main thing, the main thing, it will backtrack into the long-term outcome that I want. [52:24] Right, which at some point actually becomes very... [52:28] It's legibly evident, which is like made money, didn't make money. Exactly. You're either, you know, you should stay or you should get out of here, basically. Right. You also had this, I think it's related, you had this bit where you're talking about writing and investing and the uncertainty inside of both, which I really liked.

You said, in many ways, the job of the writer and the job of the VC are quite similar, and that they both ask you to produce an original end product, in the writer's case, articulated ideas and stories, in the investor's case, differentiated portfolio with outsized financial returns, without much of a map for how you get there.