38: Molly Mielke McCarthy - The Art of Peopling

The thinking behind 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 DeepMind, 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 before they've built and shipped something successful when if you met that person, I think you could still see in their eyes that there's something very deeply special about them if you got to know them.

Might take 3 months.

It might take 3 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 from a purely financial perspective, they are underpriced. My core belief is that magnetism 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 because it's not very 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 Milkey McCarthy. Molly is an early-stage investor at her fund Moth Fund, where she focuses on finding special, illegible, commercial, and mission-driven individuals, or people she likes to call moths. She calls them moths because they're a little less obvious than the proverbial butterfly, and yet 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, 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 in her work, and we start the conversation by talking extensively about what makes the special Mothy-type people that Molly works with is 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. 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, whether a grand change or even to settle in more deeply to the thing you know you're meant to do. Before we get into the episode, I'd like to thank Notion, Dialectic's presenting partner. Notion is a creative workspace for your life's work, and it's used by all kinds of teams from small startups to large organizations to collaborate, work with, and get leverage from AI, and ultimately turn their ideas into action. 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 the product even more powerful thanks to AI. And what I love about Notion's approach to AI is that they're focused 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, 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 that I cover on this show. If you haven't tried Notion, you can check it out at notion.com/dialectic, and whether it's your first time or you've been using Notion for years, I hope you're inspired to make something. 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. As always, you can find more information, a full transcript, and all those links at dialectic.fm, and this episode is slash Mmm for Molly Milkey McCarthy. With that said, here is my conversation with Molly. I hope you enjoy it. Molly Milkey McCarthy, we are here. Thank you for doing this.

I'm delighted to be here.

We are going to start with something I know you know a lot about, which is people and particularly exceptional people. I'm going to start with a quote from you. But what I do know is an exceptional person when I meet one. 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. How do you know an exceptional person when you see one or meet one?

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. And then I think there's something about them pursuing excellence and actually attaining it that I like to look for, some kind of flywheel around competency that I think is hard to find. I think one of the underlying premises to Moth Fund and my approach to people is that I think competence is hard to find and storytelling could 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.

How long does it take you to— like, is there a minimum viable threshold of time with someone or question things you need to know about their background to be able to kind of like get to that feeling?

3 months.

Really?

Yeah. It's very, very clear.

That's like a— that's like a— you've done— you've done a lot of this.

I've done a lot. Yeah. I think anything less than 3 months doesn't give me an accurate representation of their slope of growth. And I care a lot about that. I think 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. 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 3 months is, is a pretty accurate representation of, you know, if they've made no progress in 3 months, then they're probably not going to in the next 3 months either. And I think it's, 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. And typically though, like, I know people that I invest in for minimum a year, but 3 months is like what I look for to really get an accurate barometer before I can really say like, oh yeah, they're exceptional, or I don't know as much. It's hard to say, but does it have to be like first-party data?

Like, let's say someone you trusted, 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 2 weeks. Like, can you substitute that?

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 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— it tells me a lot about the person that I'm trying to get to know and the person that spoke highly of them. 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 a very core product 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 care a lot about people talk about. 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. Yeah, I think that's like a common trope and it's certainly poetic and broadly feels right to me. I'm curious how it like, how it sort of actually shows up and how you learn to see that maybe especially in this 3-month period where you're getting to know someone.

I think it's trying to understand what their core competency, like what is almost like their dominant leg that they lead with. And how does that make their other leg weaker? Basically is what I'm trying to see. And people usually show you by the 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 end up investing, you meet when they're very young.

Definitely.

And so they're not well-rounded by default, like they're probably not doing their laundry or whatever. Like, yeah. So it's, it's versus maybe analyzing on a 35-year-old, it would be different.

Yes. Well, I think that it's for the young people that you're right, I spend most of my time evaluating. I think that it's trying to understand their growth trajectory over those 3 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, um, you'd expect. I think you just have to listen to them a little bit closer. Like, what are they— what are they telling you? What are they not telling you? And how honest are they with themselves? I think I've never set out to look for people who are like the most fluent in therapy speak or whatever it is, but I am looking for a certain kind of person that I think fits my archetype of how I could help them. And I think it is, like I said, the one that 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, you have to also, when evaluating young people, have a lot of humility, because I've been wrong just as many times as everybody else. And I think it's, it's realizing how often our own 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 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.

Yeah, what have I even putting into the observation? One of the things I love in, um, in that classic Graham Duncan, like, what's going on here with a human is just like the ways that you as an interviewer or as an investor might be like totally warping the context a person is Absolutely.

Yeah.

Unless you're actually getting like a wildly unreliable perspective on them. You have, on the spikiness note, you have a few 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. Precocious spikiness is what gets you noticed in the world of startups. So it's no surprise how many competitive people become razor sharp, functionally turning themselves into tools tailor designed to solve specific problems. 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. Beautiful writing. I'm curious how you square this because— 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, maybe even like a burden that 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?

No, I think that pretty accurately slices down. I think that a lot of the people that I bet on have a very specific reason that they want to do the thing, and it's very close to their heart and their brain, and they care a lot about it, and they feel the need to almost exercise this vision in their head. But I think that the, the people that, um, I find myself most gravitating towards are the ones that are actually more focused on living well. And I think for better or worse, like, I both really deeply enjoy serving the people that have a mission to embark on, but they're not necessarily the ones that I want to spend all my time with, to be completely honest.

They probably don't have the time to hang out with you anyway, or hang out with us.

Exactly, they're busy.

I do think it's interesting to wonder about, like, there are probably people who at the beginning of their career start off as very spiky. Maybe even like to take an extreme, like a Mark Zuckerberg or whatever.

Yeah.

And who have gradually figured out how to like add color or resolution to that picture.

Yeah.

As it's needed.

Totally. Um, and then it's also a question of like, I wonder if you got close to him, has his— have his spikes dulled a bit?

Yeah.

Or have they remained razor sharp and he's just filled in everything else with having money and help?

Right. It's funny, I— my— the way I've used spikiness to describe people is I'm almost— I find my— because 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.

Um, I like people who have several spikes, but I like those people much more than I like people who are like very well-rounded everywhere.

Yeah.

Um, but I don't like people with one spike.

That is a very good— not that I don't like them, but like I actually think in practice, like, people that I spend the most time with are T-shaped. Like, 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 or whatever polygon shape.

Yeah, Bri has this metaphor of the fork shape.

Yeah, that's good too.

That's kind of what I'm—

yeah, totally.

You mentioned moths and the sort of the notion that you're— and we'll talk more about this later, but like you're kind of working with people who aren't totally legible. You also describe magnetism as a really valuable trait or something that you're looking for. What makes people magnetic? And, and particularly, maybe how do you think about that in the context of people who might not be the most legible yet?

Yeah, yeah, I mean, my core belief is that like magnetism 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, like, pure concept of vocation, meaning that, like, there is a right thing for people to be working on. Um, and I just think that magnetism is something that, like, there's the version of magnetism that is large-scale and something that you would, 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.

Right.

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 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.

You could totally imagine how a fairly introverted— someone who's kind of interested in the world and who's like very nerdy could be very magnetic in a specific way.

Exactly.

Right.

Yeah. Because get them going talking about their favorite part of the nerd world and then they— 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, It's huge.

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've learned a lot about how to evaluate smart people by how they've evaluated me. 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. And then you say, "Discernment can be glimpsed in their reflections. They should have to exchange their innocence for wisdom, not just experience." I think it's really, really powerful. How do you start to see the potentiality of that, particularly that last bit, which is like being able to trade innocence for wisdom?

Hmm.

Everyone trades innocence for experience.

Totally.

If they stay on the track.

Yeah, I mean, I think that it usually just comes down to actually mining the wreckage of your experiences and the winds of your experience and, and learning things from it. It's usually just self-reflection, um, 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 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, is the kind of help and support that I like to provide to founders, is this kind of quasi-coaching relationship where we're doing just that, basically. Like, how can you grow faster in the direction that you want to grow? I find that to be an endlessly interesting question. It's much less constrained to like, how can you build this startup? Well, maybe you shouldn't be building this startup, but like, that's, that's the thing we should be talking about, not like, what is the next product to build?

Yeah. Getting you closer to the vocation thing too. Or you also talk a lot about discernment, which I think is really close to this.

Yes. Yeah.

Which is, as you say, not just seeing yourself clearly, but seeing the context in the world and the other people in the situation and all of it clearly. And like also knowing 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, in really everything I do, but especially in 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 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. 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? Yeah, like that, that's just as interesting as the picking, I think.

Yeah.

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 like 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 that, yeah, in many cases it won't matter that much. But in the world where it actually very— like, you are in a position where you could significantly inflect somebody's situation, life, whatever, direction.

Yeah.

And it's, um, it's like almost carrying that weight, like, um, understanding the weight of what you're carrying, maybe, and trying to wear it lightly too.

I think I definitely gone through phases of being like, this is way too much responsibility, and then I'm like I'm overthinking. It's not that deep. But I do think that there is something about just 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— it is deep. It can be very deep.

Another quote, you say discerning founders do everything they can to stay rooted in the present, forgiving themselves a thousand times so they can continue to see the bigger picture and act. How do presence and agency relate to each other?

Hmm. 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, and you're not present to yourself and what you're feeling and what you want and what you need, um, you can have 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, 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 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. I guess maybe I have two questions, which is like one, piggybacking on the last thing, like the presence thing's 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 or it's like it has more of a future orientation. I guess the other part of that is just like, how do you think that distinction between ambition and agency affects how people should maybe interpret the classic phrase, you can just do things.

I think that so much of like agentic people, so many of them are 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 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've just been— 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. I actually, it's funny because like that was my, um, 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 people that were acting from agency because I thought that they were undervalued. I think that over time I've realized that it's, it's muddy. It's not that clean. It's nice to make a neat distinction on the page, but I think in practice, ambition is often deeply interwrapped with agency. I think that we're status-minded creatures, and it's not always clear what is a game that someone else set 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 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. And I, I really care about 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. 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. Right. 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 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 unique or original or off the beaten path is moving. Like, 10 years ago, Y Combinator was pretty, like, 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. And it— I think that that was a lot of the, um, the thinking behind Moth at the beginning was like, I saw that there was just an abundance of capital for people that were credentialed and legible and, you know, went to Stanford, ex-DeepMind, 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 before they've built and shipped something successful when if you met that person, I think you could still see in their eyes that there's something very deeply special about them if you got to know them.

Might take 3 months.

It might take 3 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 from a purely financial perspective, they are underpriced until they have shipped something. Like real.

One last thing on agency, and maybe this point is a little bit overdiscussed, but you, you— first off, Paul, 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, I thought was quite interesting, and I think it's fairly old, so I'm curious for you to reflect on it, is like the inputs to agency along this notion what I was 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, then the sustainer as these like frames of inputs for increasing it. I'm curious, like, one, do you, do you think that holds? Would you amend it or amend it? Excuse me. And then more broadly, like, as you've continued to do this, have you— do you have any updated sense of like what types Like, particularly in the sense where somebody can go from not that agentic to somewhat agentic, which to me seems like the big one, because once you get into the agentic loop, it starts to compound.

Yeah, I think I was very idealistic when I wrote that. It was like 2022 or something like that. I think that there's some truth to it, but I think it is pretty capped. I think that like people can be inspired by someone else's story, try something out, and then be in a more like agentic-filled other people environment and get to a slightly different baseline. But I do think it's hard. I mean, I think my counterargument is just seeing how, um, 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. Um, And I think it's definitely possible if you are open-minded enough, but I think very rarely are people. I think I, again, a piece of like self-reflection from writing that piece a while ago is like, I 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 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 actually— it has the same tenor of like, let's just do things, except one of them is very California.

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 that— it made me think that all people have a higher level of agency than I think that they do. Um, and I think I've also just chased environments where the people are agentic and interesting and unafraid and original. And I 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. 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.

Right.

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, 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 learning has just been being in other countries and being, you know, with visiting friends' home environments and just learning that it's, it's not at all like what I thought the rest of the world was.

I'm reminded of one other thing on this note, maybe somewhere where you're, uh, citing David Brooks describes this as adhering to the theory of maximal taste. And then 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, the best that it habitually consumes and is capable of consuming. Which, again, I think still your main point stands, which is like on a relative basis, but like it—

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 eugenic environments. And then the ones that choose to like fill their mind with things things that push the bounds are going to grow.

And yeah, it's interesting. I think I was thinking— I maybe I talked with Bri about this as well because 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 was not in an environment where like there were 15-year-olds doing great like startups and stuff.

And like, me neither.

Yeah, right. And so I have to actually like, I went from a And again, I don't know where the baseline was, but like I went from a world where like you really don't know what great looks like until you see it.

Yeah.

And so that would be my one bit of like hope on this note is like environments are really powerful.

Yeah.

And perhaps the real answer to 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, 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 environment, in their zone of genius, like, I think that that would be also like, wow, you can be like that. But I just think that—

but see, you'd have to see the process.

You have to see in person, you have to be around it, you have to absorb it, and you have to see how they spend their time, just who they are, how they relate to their work.

Yes.

And I think so much of my career was a story of like, once I got into tech, I was very lucky to be around excellent people.

Yeah.

And having my bar raised so much in this field where I was seeing that I was suddenly given so much more autonomy and, and agency than I had been in any other environments. 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.

Yeah, my sense is the process, like the garage door up part of it is really important. I was— 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, meaning it's like, oh, it's sort of like the magic trick.

Yeah, yeah, yeah.

And I actually think to your earlier point, like people are exposed to great things, but it looks easy. Hmm. And so maybe the thing is actually getting to see, 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 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, 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? Like, 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. Well, and also, like, I don't know, I just read East of Eden by John Steinbeck, and I'm reading these letters he was writing while he was writing East of Eden.

Yeah.

And it's so like, honestly, the main emotion I had is like, oh, he's, 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— 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.

One of the more important 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. 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. Like, yeah, I think 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 6 selling lollipops. Like it does feel like it's more of one of these innate things. And yet you're saying, or at least you were saying at the time, that it was largely a product of exposure.

Yeah.

So yeah, maybe, maybe first I love your perspective on commerciality and why it's so important.

And then to that thread 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 highly commercial people typically see the world in terms of money and like where it flows, how it can be captured. They just understand the world that way. It's, it's almost like their version of math in their head. And I do think that that is something that some people are just born with and do have that, like, the quintessential cliché entrepreneurial lemonade stand streak. And I think that that's really special. I think also though, 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 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.

Like you're seeing the Matrix almost.

Exactly. Yeah. And then I think that they just start to see those opportunities 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 hippie background and then came into tech and now working in venture capital. And I think like, A, you can definitely like just feel it when you're around people who are commercial. Like there's a hunger and desire there that like 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 are the kinds of opportunities I'd 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, that commercial opportunity. But it's one of the, I actually think it's a lot easier to train than agency or anything like that. Because it's less risky. It doesn't necessarily mean that you're going to start the business. You're just seeing that a business could be started.

Right. Maybe another piece that 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 timescale. 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 positive-sum bent on the commerciality that makes such great entrepreneurs?

Hmm. Oh, I think it's just they are not looking to extract value right now. That's the main difference. People feel it.

Just patience.

It's just patience. They're seeing that there's something interesting. They are drawn to you like there's some kind of kismet to the relationship.

Yeah.

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. I think that most successful founders, entrepreneurs, they collect special people and then they figure out how to slot them in. And I think that that's the same for investing too. We— I collect special people and then I see if it makes sense to invest in them. Right. 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 it seems like the 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 in making this business grow and flourish, and that requires talent. And I think that that was really interesting because I was interested in thinking in a similar way of like, how can I find special people and support them in their growth, really? But I wasn't interested in having them build my thing. So it was very clear that I shouldn't be a founder.

It's, it's interesting. It makes me think of, um, you have this thing about idea people and people people, and I know it's almost like 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.

Yeah.

In terms of where your leverage comes from.

I totally agree.

And certain investors can, can, 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, okay, sure. But your business is capped if you are thinking that way because you're not actually thinking on—

Yeah, I mean, maybe that world's gonna— maybe we're heading into a world where people 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, I— that was a while ago. Do you still believe in that? I'm curious for you to one, just like 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 just, it's more like a general thing that I'm constantly asking when I'm getting to know a person is like, do they lean more in one direction or the other? Are they going to 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 see a truth, they feel compelled to say it?

Hmm.

If they 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. And I think typically most founders skew more truth-seeking.

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-seeking and also you should only invest in truth-seeking. I think in the thing you were talking about this, you actually describe Jeff Bezos as being a little bit more on the social cohesion.

Yes.

On the note of being a customer obsessed. So I'm really curious about that.

Well, I think social cohesion can look like just being an amazing salesperson. Like, I think that the detractor, the not so good side of someone who's very truth-seeking is that they can actually, they can be very brash and very hard to build a relationship with. They're very hard to be the level of smoothness that they need to do like some kind of sales that is actually in one given industry. I think that 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 Dylan Field of Figma is a good example. They're not necessarily like 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. It's 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 Did he have to name it and like lose the deal or did he— was he able to put on the salesman face and say, okay, I'm actually— it's fine, like we'll make it work, da da da da da.

Yeah, that's it. That is a much more interesting and useful orientation of it, I think, than the like, obviously you just want to be the truth seeker.

Yeah, yeah, yeah.

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 that an investor is ideally a finance bro with a dash of Engelbart and even compared or observed that Neil Mehta feels like a very, like, 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 mods you look for? Like, what is your kind of relationship to commerciality? Been over time?

I think that a framing that I've been using a lot recently has been, I think it was Will Manitas's, his like in the flow versus out of the flow investors. I am most definitely an out of the flow investor. 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, but I don't really experience FOMO. Like 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.

Right.

And so I think that the commerciality for me is like, has always been something along the lines of I want to be my weirdest, most original, unique self, attract people who see 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 rise up and win that way and prove to everyone that investing in Moss and like what I'm doing is—

you're on the back door or whatever.

Right. Exactly. It's good business. And like that was, that was the goal of my fund one was just like, 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 YC legitimized young technical talent, the Thiel Fellowship legitimized dropouts. I think MOSS, which I define as this kind of quirky, quiet, mission-driven founder, is consistently underpriced, um, in, in part maybe because they don't seem that commercial but still are. Exactly. 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. Yeah. And I think that is— it's very rare. Yeah. 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, they of course need to have the flywheel of making a lot of money.

Basically, 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, given the context of everything we talked about earlier and the fact that these people aren't that legible, like maybe in the 3-month period or whatever, like what It's not going to show up in the way that somebody more 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 do you talk about? Like looking for the sign of growth or trajectory or like becoming resourceful or competent. But this feels like a slightly different thread.

I think it's often looking at actual proof from the past that I can do it if it's so early. But then if it— if they're like in the process of building the thing and in the early days of potentially getting money for it, it's like, how much do they care about that? Are they actually good at sales? Are 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 in the same. But I do think it's—

but sales comes in different flavors to the early.

It totally does.

Right, right, right.

I think obviously like the flavor that I'm more interested in is the one where it's like almost mission-driven sales, if that's even a thing. Mm-hmm. Um, where it's like the person clearly cares so much about the thing and is so authentic in doing the thing that they were meant to do that of course you wanna work with them or give them money or whatever it might be. Um, but I do think that commerciality is actually something that you at the end of the day need to see proof of.

Most people who are verge on the mission-driven or authentic side even if they're commercial, I find 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, what is that process like? Like, what have you observed either in yourself or in watching the founders you work with? Like, yeah, what is it like to sort of improve at the sales muscle in a way that like, does it mean becoming inauthentic or can you do it in an authentic way? Like, can you, can you improve at sales in an authentic way if this isn't your lean?

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 backed doing it and then being like, okay, it was cope. I should be doing the same. But I do think that this is one of the main things that I like help my founders with is like, it's so easy for me 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, 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 they create. And that's very important. But I do think that that is— it's something that it's very easy to be an outside observer and be like, clearly you should do you should sell it.

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.

On a note of like something I've, 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 of venture 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. And then separately, you have a line where you said Jeff Lewis has this funny clip where he says something to the effect of, 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. Great.

I think about that a lot.

Yeah, I'd love to hear you reflect on those two things, like that, like need to self-actualize. And like, really, I guess what I'm wondering about is like, how you and how one gets to this point of like total ease in the ambiguity.

Yeah.

And maybe it's very different doing that at a big firm versus on your own.

I think at 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 make, that look kind of like a feedback loop.

Totally. Yeah. But they're not. And you shouldn't confuse yourself with 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 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 long 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 3 years or so. And then I think I got 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, what is the part 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. And 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, 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, being known in the right circles. But I don't really care about that. And like I said, I don't— 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 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.

Right. Which at some point actually becomes very legibly evident, which is like—

Absolutely.

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 VC are quite similar in 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. The reason professional writers complain about writing so much is that it's really difficult to wrangle your brain into producing uniquely interesting thoughts all the time and highly frustrating when you consider it your job to do so. Making good investment decisions is similar, just with the added element of also being highly social. Taking the quality of your self-talk seriously seems superfluous, but it is an investment that will result in better decisions.

Yeah.

And so obviously a lot of that is very similar to what we were just talking about, but I'm curious specifically about that last bit, which is the self-talk piece inside of all of this ambiguity and your ability. And granted, part of it for you maybe is it's less about coming up with unique ideas and more about finding amazing unique people. If like, what is that connector between self-talk and like decision conviction and ambiguity?

Well, I think it's like not letting the FOMO get to you and also not letting the, the self-doubt around, was I right if when I followed my hunch on that investment, was I, you know, this person isn't taking off as fast as I thought they would. Was I wrong about that? Like, I think it's just, it's almost thinking less. It's actually just thinking less. Yeah. I think that like the best purest way of doing investing is like not even doing investing as your full-time thing because you think too much about it.

Right, right, right.

It's almost smarter if you like, I don't know, you, you have some other—

you're writing a book, whatever, especially the people-oriented investing, right?

Exactly. If you want to go deep on ideas and make bets like that, completely different story. But for people-oriented investing, where you actually kind of know whether you want to back them after like a 30-minute, an hour-long meeting, which is in my case typically how I do it, um, it just takes me longer to get there. But like, I have a sense, I have an inkling that I'm trying to validate. I think that it's, it's much more productive for me to just continually show up as a blank slate basically, and serve the people that I've backed in their growth and not think about really much of anything else.

That's what it's all— it's almost like plant the seed and then like check back.

Get out of here. Yeah, yeah. And keep watering it. But that's about it.

You interviewed Daniel Gross for your podcast a while ago, and there's this really amazing part where he is expressing that, like, one of the number one things that people in most parts of investing and like most traders totally understand and that venture investors underrate is counterparty risk. And like, why is this deal coming to me?

Yeah.

Which I think points broadly at like a thing that I think you think a lot about, which is what is the signal, what is the bat signal I'm sending out there? What is the brand I've created, whatever it might be, that is going to route things to me? I think in early stage investing, that's like the only way to have any leverage or scale. And one of the things Daniel observed is like actually like staying too top of mind in a broad sense might actually be bad signal. I agree with that. And you've talked about this. It's like actually like you want your brand or whatever you're putting out there to generate as many nos as it does yeses.

Totally.

I think you've internalized this and clearly you're like, you're very deliberate about it. I see. I might, from what I can tell, it seems to be working for you. Maybe first, like what is that bad signal? You've talked a bit about it somewhat today and like, Yeah. How, like, what is, what is the maneuvering on that as you like A/B test? Like, how do I, how do you even know when it's working?

I think about it a lot. I mean, it's like, I think that is like maybe the one thing that is worth stressing out about as an investor is like, am I the product of adverse selection? Yes, that is, that is a real existential fear that is actually worth thinking about.

It's like, who said no for this to come to me?

Exactly. Yeah. And I think for me, like, my strategy was kind of distilled after seeing what worked in my Fund 1 and realizing that, like, in most cases, the best deals came from— well, 50% of them were direct relationships with founders. The other 50% were from people in my network who were eyes on the ground, deeply embedded in the domain, usually an operator or a founder who, who got me. Like, we just understood each other, and they got what I was trying to do with Moth, and they could accurately describe what a moth is. Like they, they understood.

Yeah, they were taking your language on you.

Exactly. Yeah. And the premise that I would give them is like, if there's anyone maathi that you meet, I would love to meet them. Like, they don't— ideally they're not raising, ideally they're just a guy that's like interesting and thinking about ideas, whatever it might be. And I have different mechanisms in which to meet people. One of them is grants. And so that could be like under the premise of what is the project that you're doing that you're excited about? Let's talk about that. Another is the kind of coaching help I do around like, what do you want to do next? Whether you're deciding whether you should raise venture, deciding what your next move is, deciding whatever it might be. I like working through those problems. I think they're very high signal. Um, and then another one is just like, just general, like, how, how can I help and serve this person? It's like non-prescriptive, but you seem like a moth. I think we should get to know each other. There's not a lot of people like us, whatever it is. And so I think that that Those all spin the flywheel too. Those all spin the flywheel. And they're all like, basically the ideal experience is like, I just want someone who gets me and I've transmitted the memetic moth thing into their head for some kind of bell to ding when they're meeting a person. They're like, you should meet Molly. That's what I want.

That is the thing. You're prompting minds.

Exactly.

Right.

And I'm just trying to give them like, what is the minimum viable definition of a moth that they get, that they can like hold on to and feel something about. And it usually means they are one. It's like it spreads between people who get it. And so I think that the definition, the working definition of the moth is like, it's typically people who feel kind of misunderstood. It's like they are more the mission-driven, the quirky, the quiet, the illegible, whatever, however you want to say it. But they could be summed up as being weirder. And I think that that is something that I try to meet all of those people. And then like I said, I'm trying to see which ones take off. But I think another filter mechanism that I have in place is like, My writing is something that I wouldn't say is usually, you know, how founders find me, but it is very, very, very frequently cited as a reason why they wanted to work with me after they're getting to know me, because it shows who I am. Like, I think I try to be very authentic and honest in my writing, and it shows what I believe, how I'm going to help them, how I see the world. And if I'm not the right fit, like, they'll know that even when the referrer is like, you should meet Molly, here's her writing. They look at it and they're like, right, saving you already time. That's fine. Saving me time. Great. I do not take a high volume approach. I tend to meet only kind of qualified candidates that I think actually have something quite interesting. And I think that that is just my preferred style of working. It's what's sustainable for me. Like, I'm, I'm not a person that would thrive on the, you know, in the flow, go, go, go kind of way of doing investing.

You mentioned coaching a couple of times. Specifically, you talked about understanding people's motivations, failure modes. You reference Enneagram somewhere, that being one of the ways to get much better at this. I guess I'm curious how else you've learned to get better at that. And beyond that, is the coaching— and granted, it's a little different as an investor, but is that what is the art-science gradient on that? And I think maybe a lot of people listening, if they've had positive experience with coaching, might view it as somewhat scientific and very valuable and obvious. And other people might view it as, I don't know, like all art. Is there even any substance here or whatever?

I mean, I think there's a huge variety and some of it's terrible and some of it's great. I think I've been very lucky to have a very good coach for most of my time, uh, working on Moth, and she is trained in Enneagram and IFS and all kinds of other things. And I think that that has been very helpful for me in just having, um, someone who I've learned a lot from her viewpoint and how she's helped me make sense of myself and the world. And I think I've just— my bar has again been set very high. Like, this is what good coaching looks like. It's incisive, it's truth-seeking, but it's also deeply empathetic.

Right.

And that's what I strive to be, I think, for my founders. I'm not anywhere near as good as her, but I do think that there is a deep lack of that approach in venture capital. And I think that there's a deep need for it too, is like just being there with people and, and actually really helping them understand themselves and what's going on in their head and in, in their company, whatever it might be. And so I think that that is typically how I think about it. I think that honestly though, like, I came from a very weird background with very strange people that I then spent a lot of time trying to understand, and I've just always been interested in people. I think my career can roughly be divided into a bucket of peopling, and that's understanding people, being discerning about people, supporting people, whatever it might be, and then making things, and that's the film, you know, trajectory, photography, art, just all the things that I did that were much more about tech. Yeah, design, tactile or digital creation. And I think that the peopling is what I am focused on the most now. And I think that the inputs are honestly more than anything just data points from the world. Like, I really— I do strive to see every interaction that I have with a person as an opportunity to learn from them and about them. And I think you you get a lot further with people faster when you try to go that way. Even when we don't end up working together, I think I do learn something new from each person. But then also, I'm a geek about, like, Enneagram and, yeah, a lot of other systems like that.

My last thing on this, I think, is you certainly express a lot of optimism about, uh, and, and you're good at finding, like, weird kids. Like, you are— you, you your work and your writing and a lot of it conveys a sense of like the kids are going to be all right. Maybe even.

What?

You have this amazing essay called How to Be a Kid That Goes Places. I really loved. And you're articulating sort of like maybe the ways that the archetype of the founder has evolved.

Yeah.

One little excerpt, you say, I believe that good founders have been and always will be ends of ones. But what constitutes an outlier is dependent on where they stand in relation to all that came before them, which in many ways is kind of like a summary of what the piece is about. I guess two thoughts or two questions. One, I think you wrote that in 2023. I'm curious if there are any update— major, major archetypical updates to like that type of person, what you're seeing. And then two, I guess as an investor, like why? What's your plea for people that the kids indeed are going to be all right based on what you're seeing on the ground?

I think I'm just so, um, buoyed up by meeting people who are doing it their own way. Um, and I think that I do attract and work with a lot of them, and I think that they, they work on ideas that are controversial, strange, hard— definitely not B2B SaaS, definitely not usually an AI company. Um, and I think that that gives me a lot of optimism just because I see that they're doing it in the face of so many other easier options.

Yeah.

And I think it also— it makes me optimistic to see that so much of the rat races that so many people are— get caught up in these days of like collecting credentials or fame or whatever it might be, um, there's a whole other class of people that completely avoid that entirely and see it for the hoax— or not hoax necessarily, but like the hoax for them it is. Ah, and I think that that is inspiring to me because I think that like, I definitely was not like confused by that at the beginning and had to figure it out and wasn't as clear-sighted. And I think that there's a clear-sightedness to so many of the, the young people that I meet today that I think comes as a result of, um, coming out the other end of nihilism and being like, I'm not going to think that way. I'm just going to build whatever I want. And figure it out from there. And no one, you know, can drag me into some stupid, I don't know, rat race or whatever it might be. And so I think that that gives me a lot of optimism. And I think that the archetype, it has evolved a bit. I think it's just become more high variance. Like the people that— the young people that are uber successful at a young age, they're getting even younger. Okay, great. Like, I just think that it's almost like everything gets pushed to greater and greater extremes. And it's always a question of like, how far will it get pushed? Like, well, the next founder will be— will he be 9 years old? Like, whatever it might be. I just, I find that to be like, you're still playing by and measuring yourself on the same rule sticks. And it's age, it's like how much money you made in a, you know, short span of time. It's like I don't know, measuring yourself by which powerful people's ears you have, whatever. But they're all like, okay, that's, that's all exciting, but I'm more interested in like, how are you a person that is paving a path that is getting you to a place that you actually really care about?

Getting you closer to vocation.

Exactly, right, to like the thing you were meant to do. Because I, I just, I think that all of those credential collecting, like whatever it might be, looking impressive, is like, it's interesting, but it's And it definitely does benefit you in ways, but I'm just so much more interested in people that are more focused on doing something than being someone. I think that that's the main thing that I look for these days more and more because I think it's, um, it's a, a very large green flag to see that they're doing that at a young age. It's hard to find.

You write a lot about understanding yourself, at least you have in the past. I think maybe if there's definitely a pattern more towards, as you were, we comment a bit about earlier, like doing rather than thinking and ruminating. Um, but I think like many people, I, I enjoy reading and talking to you. There's this like introspection-agency thing where like they're, they're, they're feeding each other.

Yeah.

And so I'd love to talk about kind of like the inward view in the self a little bit.

Yeah.

Maybe to start, like uncertainty is definitely a common theme, um, as you're navigating. A few, a few kind of excerpts Emotional ambiguity does not need to make you anxious. Great. Then I used to find inherent instability beyond frustrating. I'd claw to grasp any sense of steadiness, accepting bad deals as long as they had a lower bound I could see. Just really, oh, I think we've all felt that. And then finally, instead of a conclusion, I have an observation. People are perplexing mysteries who can never be fully aware of their own plots. Why is there such a beautiful quality to seeing that in another while a tragic feeling when we find it in ourselves? How have you learned to embrace more uncertainty?

Oh, that's a great question. How have I learned? I think I have just built out a stronger baseline of the things that I can control, which are like a stable group of people that love me. And, you know, I, I'm very lucky to have a wonderful husband, and like, the life that we're creating together is, um, something that brings me a lot of joy and stability. And I think that that has really raised my uncertainty tolerance a lot. Like, having that baseline be so strong— yes, it's been incredible for just watching how something can go wrong in my work or my life or whatever it might be. And it just doesn't feel that bad anymore. It's not crushing because it's not a sign of like everything is coming crashing down anymore.

Yeah, not every incremental thing is causing everything to crash down.

Exactly right. And so I think I'm more than anything just lucky in that sense of like, but I do think that there, there was a concerted effort made by me over the last couple of years to be like, Okay, I've been chasing career success and whatever it might be for a while now. I've been working ever since I was like 14, multiple jobs. And I was very focused on like getting to a place of stability. But I think that even once I got there, I realized that it wasn't actually going to grant me the kind of stability that I wanted. And so I wanted to focus more on the other areas. And turned out that's what it was. That's what I needed.

You have an amazing line from— and I think it's at the very end of an interview with Spencer Kier back in June of 2023, uh, which I think I find a little bit paradoxical, which is, uh, you say, asking yourself what you're trying to convince yourself is true and acknowledging that freedom and something quite possibly better might be being open to the opposite. Do you have any advice on like seeing the water on that on the what you're trying to convince yourself, the thing you have the really firm grip on that you're not loose on?

I love this phrase that my mom used to tell me, which is like, stop shoulding yourself, which is like, what is the thing that you just keep being like, I should be that, I should be this. And then I think that the clearest sign that you're onto what that thing is, is you're just beating yourself up all the time. You're procrastinating, you're avoiding shame. Basically. And that's typically how I think about procrastination, is like avoiding shame or guilt or whatever it is. And I just think that that is so often, um, a sign that, okay, what, what is that statement, that should— I should be this, I should be that, whatever it is— and why is it so important to you? Why are you clinging to it? Like, what is it? What does it mean if you were to release that and say, I actually just don't need to be that anymore? Yeah, what happens? Like, do you get really scared? Like, what is the reaction? And then getting okay with that reaction. I think, like, this is all very, very hard and takes a very long time, but I do think that that is something that, um, I learned a lot about just through the process of my career, of like, I should be, you know, still the shining golden child or whatever it might be in my career. And then just realizing, I'm like, why should I be that? Do I actually care about that at all? And it was like, no, I don't.

Also, often it's like, to the point of your original quote, like it's often that like you're holding it so, that should so firmly that you don't even acknowledge that it's an option.

Exactly.

Like that it could be.

It's like you think it's just, this is how the world is. I have to be this.

Yes.

And that level of like clinging is like such a sign.

I think this relates to the uncertainty thing, but I have two quotes on other people's love. The first, you say Jenny Slate has a great tweet about the feeling at the beginning of this process. As the image of myself becomes sharper in my brain and more precious, I feel less afraid someone else will erase me by denying me love. You're talking about obviously like authenticity and getting close to yourself. And then separately, it surprised me how many of the shameful parts of myself I've unearthed from walking above such ravines have turned out to be exactly what the right people love. In a sort of like being able to sort of like open yourself. And also on the note of authenticity, And I guess I pulled those two together because it feels like other people's love is doing a lot of work on both fronts. And so I guess my question is, how have you learned to accept other people's love and also not require it?

I think it was only after learning to accept it and live with it that then I was like, oh, actually, this is great, but I don't need it. I don't need to chase it.

Yeah, that's a painful realization. It's like, do you need to get— do you have to get the thing to realize you don't want it? You need—

yeah, exactly. It would be amazing if you could shortcut that. Um, but yeah, I mean, I think that I, I have been very lucky to be loved so wholly by both my friends and, and Tom, my husband. But I do think that it's It just taught me a lot about, like, all of my reactions to that were like the same reactions that I would have in like a work context or whatever it might be. I think that there is something like deeply true about the statement of like, the way you do one thing is the way you do everything. Of like, you know, if I would start to— things would start to go so well in work, then I would be like, oh no, it's so bad, I don't even want this, that kind of self-sabotaging. Would be like the same reaction if someone was like too nice to me. And so that's the kind of thing that like, you're like, this is a me problem, right?

Like, this is dumb, what am I doing?

And I'm very lucky to have like a good coach and people that could help me sort that out.

Uh, another pair of quotes about, I think, like getting closer to your motivations. Maybe it ties to the coaching stuff too that you're doing for other people. Um, this is you. I've long believed that my purpose is to make beautiful things and love my people dearly. But it took a sizable life chapter shift to help me actually reorient my days around that belief. I notice now how my motivation slumps immediately when I ever feel disconnected from either goal.

Yeah.

And then separately, I suppose what I'm saying is that my ambition is no longer an ambient mystery to me. Instead, it lives closer to my heart, directly tied to core beliefs I hold about the world. It's just a beautiful way of articulating, I think, what true authenticity can do to allow for agency, as we talked about. But I'm specifically, in that first paragraph, I'm specifically curious, like, how did you reorient your days to get closer to that?

Less meetings. It looked like spending more time with the people that I actually wanted to win. Like, I think in a work context, it looked like, uh, instead of just taking all the meetings to make yourself feel like you're being productive and being a good VC, like, actually just spend time with the ones that you're the most excited about and carve away time for, like, serendipity and, like, scouting in the places where you, you want to find people. And then also just, like, save that time for going deep with the ones that really surprise you and that you, you really like. And so I think it was It was something like that where it was like, okay, actually, like the right for— right kind of balance for me is a lot less meetings than your average VC per week. And it's a lot more time for me to, to think, develop my theory of a person, to spend time with them, and to develop my own kind of like, I don't know, ideas about the world and how I see things and have time to write, really. And so it was basically carving out time for that in a work context, and then also carving out more time for my friends.

It's almost like dropping shoulds.

Yeah, exactly.

Dropping a lot of shoulds about the shape of how this— my conception of how this is supposed to be.

Totally. Yeah. And even like in the context of friends, it would be like instead of, you know, shooting myself into spending time with lots of different people and having lots of different looser friendships, actually I'm just like, I'm perfectly happy with like 5 close friends. Like that's ideal for me. And, and actually just accepting and embracing and designing my weeks around that I think has been huge.

We've talked about around it, at least I should say, and one of the sort of like dominant themes that continues to come up so much in my conversations is this like dance between legibility and illegibility.

Yeah.

And it's something that I think you write so eloquently about and think about in the context of your firm. I have a bunch of quotes that I think tie together, but I wanted to read them as a group. First, describing one of your blogs: I'm particularly interested in topics that I describe as milky, opaque, and difficult to define, often with no clear answer. Moths focus more on doing something than being someone, which is a beautiful articulation. Despite spending a lot of time helping others develop the skill, I felt strongly that making my story easily digestible to others would diminish my authenticity in a way that felt self-serving and wrong. And then finally, watching influencers and applying to college seems to have programmed everyone my age with the belief that everything we do needs to be narratable as we're doing it. What I found, though, is that making myself understandable all the time diluted the joy that lies instead in specificity and concisely crafting a life that only needs to make sense to me. Being neither understood nor wanted is pure freedom. Which is a great case for illegibility. What's the difference between uncertainty and illegibility?

I think illegibility is choosing not to make yourself understandable to the world. I think uncertainty is not even understanding yourself, yourself, you know, like being uncertain about where you stand and what— why you are doing what you're doing. I think illegibility, you can have certainty about those things. You're just choosing not to—

a lot of confidence publicly.

Yeah, exactly. Put the microphone to your mouth. Um, and I think that there's a lot more power that lies in that, especially today than ever before, because it's like become more and more of the norm that you should publicize anything you do. And I think that there is a—

right now, by the way, like yesterday, 2 minutes ago.

Exactly. Yeah, precisely. You should have started, you know, 5 years ago. But I just think that there is a lot that you can learn from actually just spending more of your time doing the thing than talking about the thing. And that's why part of my theory of like Moss and like focus more on the people that are, are spending more time already doing things than being someone is that I think that they get further faster. And I think that, um, they also get to more interesting places because they are thinking more of themselves and they have a deeper sense of who they are because they're not trying to package themselves to perform well on social media. Usually it's what it is. And I think I'm— I mean, I've definitely like spent a lot of time on social media. I grew up on Instagram and like, um, spent a lot of time on Twitter during COVID And I just think that it was— it like taught me a lot in self-presentation and like I think got me in a lot of rooms that I wouldn't have been in otherwise. But I also think that it was something that I very quickly started to feel like it was controlling me versus me controlling it. And I have always been very sensitive to when it feels like a job or a platform or whatever it is, is like changing me. I'm like, no, there's no way. I even feel that way about venture too. I'm like this— I'm here to deepen relationships with people who I think are going to really win, and that's what I'm here to do. Venture is not— I'm not going to let it change who I am. And I think that— does that mean that I'm less competitive? Sure. But like, I'm playing a different game again. And I think that it's, it's similar with eligibility. It's just more about like, how can you continue playing your own game and finding your own voice?

The implication there, at least especially for your founders, and I think also for you, is that like at some point, even going back to where you said like they're going to get farther, is that like there will be a time for legibility.

Absolutely. Yeah.

You have a— I think it's like an advice column recently where you were— somebody was asking about this kind of dilemma and you say growing up is realizing that we're all special snowflakes, especially in Silicon Valley, and you can't expect others to know why you're special unless you tell them. If you feel rejected or like you did something wrong when your specialness isn't immediately recognized, you should probably address that belief head on. At a bare minimum, I hope you stop self-deprecating. That's not humility. That's critiquing yourself before others can in order to feel a sense of control. How are you?

Ask me how I learned that.

How are you becoming more legible? Or to what extent is that something you're thinking about? Like, how are you, maybe especially how are you doing that without letting it subsume you?

I think it's just very instrumental at this point. It's funny because I think I was always not the biggest fan of instrumentality before. I was like, oh, it's, you know, much better to have long time horizons and like be less attached to the outcomes. But I think in practice now I see, you know, being legible as a chore. It's a chore to get on the stage and perform myself and make myself clear to other people, and it needs to serve me in some way. And so I'm only going to do it if it's going to serve me. And that doesn't mean that it's like you know, here's my story, click here and give me money, whatever it is. But there is something about like, okay, I'm writing this piece and it is to say this thing that needs to be said for it to be clear what I stand for to these people.

Yes.

Cool. Great. I'll write the thing. It's very clear. It's actually makes writing a lot faster now too. I actually know what I'm there to do as opposed to just being like coming to the page and be like, oh, what should I spend my time on now? But I do think that there is some core tension that I still have and probably will always have between legibility and illegibility. And I don't, I mean, to be clear, I don't spend, I wouldn't say I'm the most legible person and that's like by, by choice, I would say.

Yeah. It reminds me of, um, well, I guess two things. One is like the Beyoncé, like Sasha Fierce persona.

Yeah.

And you even have it. I don't think it's quite the point you're making, but it's related, which is you have something where you talk about like, adopting this persona of Dolly when you're writing.

Yep.

Like, there's almost like a role-playing that makes it easier.

It's way easier.

It makes it more instrumental, maybe.

Totally. And especially as someone who, like, if you hold your identity, if you care about something feeling like you, it's hard to loosen that grip and be like, you know, what if— but a person like me wouldn't, you know, write something bad. But it's like, if you put on an alter ego, they can write something bad. It's not you. It's fine. It's a funny mind, like, loophole.

You, I, so much of this is also about like the fact that I think you are in many ways a, an outsider who has been able to be an insider in the ways you need to, or at least you're dancing on that line. One thread of this that I'm curious for your perspective on is like, particularly given that your job is to be around these like really amazing people. And granted, maybe with the people you're investing in, they're early enough and they're so mothy that there isn't quite this. But even earlier in your career, you worked in a number of amazing companies, and I suspect you still spend time around really charismatic, compelling people. Like, how do you— how do you not, like, get sucked into the gravity well? Like, how do you maintain that sort of sense of distance? Because— because also you're not like, I'm not going to participate in this world at all. Like, you are dancing in and out.

I think it all comes down to like, I just want to be myself, like, and I think that I— if you know anything about the Enneagram, like, I'm a 4, and so I just really want to pave my own path and be really good at the things that I have skills in. And so I think that I show up differently in meetings with people. So like, if I'm meeting someone that— like, all the founders that I invest in are smarter than And that's great. Like, that's how it should be. But I'm not striving to be on their level. I'm not even pretending. Like, I am here to help you grow, and I want to deeply understand you and show you what I see. And you need that. Like, I just— I know that I can help. I think I have a confidence in that. And I think that—

that there's an ease in not needing to also feel like you need to compete or something.

Exactly. Like, I let go of that probably like I don't know, 3, 4 years ago. And I was just like, this is not like, I'm never gonna, even when I do win, it's empty. Like, 'cause I don't even care. It's like I was measuring myself by somebody else's like rule stick. And so I think that that is something I remind myself of a lot, but I also think I've kind of put myself in a corner where I'm not really comparing myself to other people very often. And, and again, it's like if I'm comparing myself to other investors, like We're both being evaluated by do our investments in like, you know, 5 years from now make money, make a lot of money. So it's not clear. It's hard to be competitive in that way. But I do think that like the insider and outsider point is, is something I still think about a lot. I think that I, I was able to like kind of become a bit of an insider at a point in my life when I was more open to changing myself. And I think I've benefited a lot from that. And I think now I'm more— it's a constant kind of like dance and tension between like, how much do I still care about the things that the insiders care about and how much— what's the compromise? How can I still be myself and still be an insider?

Right, right.

Because I benefit a lot from being in Silicon Valley, in startups, and like connected in a way that could, you know, help me raise a fund and invest a fund well. And I think that that's something that like I can't get too fringe, if that makes sense.

Well, that's why I think it's such an interesting dance.

It is, yeah.

You're actually like, it's like a balance.

Totally, yeah.

You wrote a, or I don't know when you wrote it, but you published a list of personal principles back in April of 2023. There's 5 of them. You say, play games of my own design, feel deeply and without remorse, hyper benevolence, not writing is worse, and preciousness is worth protecting. I've asked you a few similar questions, but any amendments, any observations, anything you would add? Have those held?

I think they've mostly held. I think I'm less precious about preciousness. I think I've become more truth-seeking over time, which is interesting. I think I've just become kind of fed up with not saying the thing. I think I've realized that there's I'm, I'm much more punchy on the page. Like, I just kind of say what I think, and I find— I've always found that very easy. I've, I've been writing for my whole life, but I think— and I've always found it very easy to be very direct in conversations with people where we're talking about them and we're talking about— we're seeking truth on, like, what is true about them. And I feel like I'm, like, in my zone of genius when I'm doing that. But I think I, I used to be a lot more precious about, like, tiptoeing around emotions and making sure that people were, like, feeling okay and taking care of their feelings. And I just don't care as much anymore. Like, I care about I care about your long-term growth, like, as the person I'm talking to. And I care about you and me having, like, honest, deep, authentic rapport. And I think the tone of that is set now more by me. Like, it doesn't need to be set by other people. I will set that tone with my founders, and if they don't like it, then that's another great filter mechanism. Like, this is not the place for you. But I do think that at the end of the day, like, yeah, I— preciousness is great, but it's not everything. Everything else holds true, though. Yeah, thank you.

Pretty good.

Yeah.

Pretty good hit rate.

Thanks.

A quote from you. "Remember that fear of failure fades into the background if you focus on leaving everyone you encounter along the way better than you found them." Is the antidote to all of the self-torment and ruminating we do just service, just turning outward?

Partly, but I think it's like, what is your version of that? Because like, there's a version that is, how do I show up and serve this person? And that feels slightly different and not as resonant for me as how do I show up and connect with and help this person? That's the version that hits for me. Like, what is your version that like plays to your actual skill set?

Yeah. Yeah. Authentic service.

Authentic service. Exactly. Because I think that like the idea of how do I show up and serve them, to me, the insinuation is like, okay, now I, you know, it's my job to give them a lot of intros and like do a lot of things for them. That's not how I help. Like, my help is a very much more personal, much more like relational, deep help. Um, and so I think that, that— but yeah, I think that rings true.

I want to talk a little about friends and friendships. Two quotes: I'm in an industry where the term friend has no meaning at all, and it took me a long time to learn the difference between a few good chats with someone, excitable, often unearned intimacy, and true friendship. Requires effort, not without friction. I've consistently shied away from testing the depths of my relationships for fear of judgment or rejection. And then I realize now that asking for big things was exactly what I needed to do to gain a great deal more confidence in the community of wonderful people who love me. How have you gotten better at asking?

Mm, forcing myself off the ledge. Push. It is though.

I think it's the hesitance.

The hesitance is like fear of rejection, fear of humiliation, or something of that sort.

Um, is your willingness to ask proportional to the connection?

I think it is. I think it's partly— it was always like an insecurity about like, is my perception of the depth that we have the same as your perception?

Right.

That's always the— right. And so it's like asking for something large is a test of that. Was I right in my calibration of how close we are? And I think I, I wasn't sure about that for a while because I was so scared of asking. I would just always like kind of run away instead of testing the depth of the relationships.

Well, again, this is where like it's like, um, you're sort of underrating all of them. Exactly. Like the lean, right?

Right.

You won't ask anyone of anything, right?

By your actions. Yeah. But I think I've also now realized there— someone said something along the lines of like, it's actually, you know, you're denying them the satisfaction of being able to fulfill your request and do something for you. Like they would actually find that deeply meaningful. Why are you not asking them and giving that opportunity?

Yes.

And it's almost the same for like a framing that I like for selling is something along the lines of like, if you're so scared of asking someone, why are you not reframing it almost in terms of like they might be offended if you didn't ask them because it's a good opportunity and you should be bringing it to them.

It's generous.

It's generous. Exactly. It's like these mind tricks, they do go far.

You just got to judo yourself.

Yeah, exactly. Judo yourself into doing the thing you know you need to do. Yeah.

I think it's honestly, again, a theme that comes up multiple times in different concepts for you is like, the way to— like, inspiration comes after acting, and as does forgiveness, or anything. Like, all these feelings come after the act of doing the thing.

Absolutely. Yeah.

And a little thing about, um, something I've thought a lot about, which is like intimacy and intention and proximity and idleness and how those wrap into friendships. You say, sure, you can feel superficially close to someone by asking and answering the intense questions but that isn't a relationship. It's just an experience. Hang out on a billboard somewhere. Um, intimacy runoff is what I call it when a usually young person craves closeness slash feeling seen but isn't looking for it in the right places. So they do things like ask weirdly deep questions of strangers or confuse their ambition for attraction. The bedrock of relationships is consistency and time. How do you practice maintenance in your friendships? And how do you like— how do you like— how do you get better at defaulting to kind of maintenance versus like falling for what you're starting to point out, which is the illusion that like, oh, we don't need proximity and maintenance. We just need like one really deep conversation ever so often.

Yeah, yeah, yeah. I think that the main thing that's helped with this is just becoming less avoidant. Like, I think so much of running away from the friendships you already have usually comes from a place of like there's some kind of shame or guilt or something there that you're like, 'Oh, I haven't followed up to schedule with them for like a month,' or whatever it is. Like, 'I should just talk to somebody else because they obviously don't want to see me either.' And it's like, you're just avoiding something. You're just like inventing something to avoid and like grasping for something else. And I think that that is the kind of thing that like just asking for more things, being more annoying, being more yourself— like, I think over the just like the last year or something, I think I've been more, much more comfortable showing myself to my friends and the people around me in this way that has shown me that I, I should. And they will rise up to support me in really beautiful ways. And that, like, the depth of friendship was really— like, I was the limiter. That was the big thing. And I remind myself of that often now. I'm like, is this— am I acting from a place of avoidance? I guess it's like a constant question that I'm asking in the context of friendships and relationships.

Painfully true, I think. Another essay of yours I loved is, I think it's called "Women See in the Third Person," and you quote John Berger to start. He says, a woman must continually watch herself. She is almost continually accompanied by her own image of herself while she is walking across a room or while she is weeping at the death of her father. She can scarcely avoid envisaging her self walking or weeping. Her own sense of being in herself is supplanted by a sense of being appreciated as herself by another. And then this is you. Women are simply much more inclined to strategies that guarantee safety than men, which is all great and good until you realize how far these strategies distance you from your desires. See, that's the catch about living life in the third person. It makes it very hard to know, much less act on, what you want. And then you go on to say, living life in the third person means the possibility space of things I allow myself to say and feel are constrained to the aesthetics of how I want to be perceived. At risk here is ownership of the little thing I call my life. Just powerful stuff, um, and obviously not something I can relate to. I think my question is, to what extent have you gotten better at living in the first person? And to what extent have you embraced seeing or living in the third person?

I think it's very helpful in the context of being good at brand and marketing.

Yeah.

Living in the third person in that way, like, yeah, you need to be able to think, how are other people going to perceive all the things that I do and like how I present myself? I think it's great in the context of storytelling.

Yeah.

Because you're like, you, you're basically You're like one of those startups that's able to like create virtual humans, but you're doing it in your mind. And you're thinking like, what would this person think? What would that person think? And I think like, I was always pretty good at that. And I think it was very useful in the context of like all of the mediums that I made things in. But I do think that it was massively limiting as soon as I got into investing because it was like very clear that I was thinking so much about what other people were thinking.

It's consensus-driven.

And it was, it was, it was leading me in directions where I was like constantly pushed and pulled between like, I want to be myself and do my own strategy, but then I also care a lot about what other people think— my LPs, other investors, founders, whatever it is. And then there was a distinct turning point of just kind of like realizing that I'm like, which part do I actually care about? Okay, yeah, I actually just don't care about any of that. I'm just like, it's something I can grasp onto to feel like I'm in control. In a job where there isn't a lot of things to do that feel that way. And so I think that that has— that helped. It's like kind of just like dividing the two. I think I live much more in first person now than I really ever have, and I think it's mainly from just like getting the confidence of taking a lot of leaps and making a lot of big decisions and being like, I made that and it was for me and it was not for anybody else. And I think that really compounds those decisions. They grant a sense of confidence and like knowing who you are by pointing at decisions and being like, I did that.

It's related. I don't think it's certainly not the exact same, um, but it might be somewhat related. How do you lean in to and out of femininity in at least the professional part of your life, which is obviously a very both literally and also energetically, like a very male world?

Yeah, yeah, yeah. Oh man, I, um, I think I've gone back and forth on this a lot. Like, I think in the beginning I was, I was much more, um, attached to preserving the way that I treated people, um, and like the nurturingness. I think I have become more truth-seeking over time and just more direct, less precious. I think it wasn't as core to who I am as I thought it was at the beginning. So much of this job has pressured me to change in various ways. And fundraising is like the main example. And I think that it's like probably the one area where I actually do have to be more something that is like not what I would call myself. It's a part of me. And I've made my peace with that, but it's definitely a much more male—

Putting on a role to be legible.

Exactly. Yeah. And it's worth it because I'm getting something out of it.

Yeah, it's totally instrumental.

Totally worth it. It's completely instrumental. Like, I'm using them, but I have to remind myself of that because otherwise I feel like I'm, like, selling out. And that's, like, the worst possible feeling for someone like me.

Enneagram 4.

Yeah, we really don't like selling out.

That's good. I actually— this is quite related. I want to talk briefly about love, but to start, I think it's connected. He Tom, your husband, showed me that he didn't want to own me by helping me see all the ways I was the one trapping myself. How has Tom's love been freeing and empowering for you, maybe particularly in that regard, and maybe allowing you to see more in the first person?

Mm-hmm. It's made me a lot more safe and, like, able to embrace myself. And I think it was from, like, showing him all of me and having him accept it with open arms. And I think also just growing together, like, yeah, seeing that I'm able to help him in ways that have revealed to me what my strengths are, and he's able to help me in unique ways that show me what he's good at. And like, that kind of symbiosis and like relationship has just really, really special and made me much more confident in myself.

Um, relates to the uncertainty point earlier.

Exactly.

Like, there's, there's really stable thing that allows the other stuff to be—

Exactly. Yeah. And also deeply getting to know a person and like seeing how I am different and the same from him. I think we are in Enneagram types, we are like the opposite. He's a 7, I'm a 4, which is great because we, we have very clear lanes of what each person is good at. But it's really informative to see another person live in a completely different way that fits in well, like we have the same values and all that, but like they're— it's constantly reminding me of my choices and why they're important to me. It's like there is something about that contrast that's really powerful. Yeah.

A quote on love, uh, I was raised in rural California and resonate strongly with Stewart Brand's vow of conservation, which says that signatories should aspire to, quote, leave everything better than they found it, end quote. This applies to people too. Any love I made you feel is yours to keep.

I stole that from a tweet.

Beautiful.

Good.

How does— maybe it's all this, maybe it's this thing we've been tracing over and over again, but yeah, how do you get closer to that just kind of like total abundance when it comes to love?

Letting yourself feel it, I think.

You realize it's multiplicative.

And I think just like surrounding yourself with it in a way that maybe, like, I definitely felt like might have been selfish many years ago, but I think it's actually— I've just realized, like, it's just like, it's wonderful in the way to live. And reprogramming yourself kind of to expect that, but not, I don't know, act like you deserve it. Something along those lines.

I jotted down a note of you quoting Tim Keller that maybe is a clue here, which is the feeling of love follows the action of love.

It does. It's very good. It's a banger. Yeah, isn't it?

I have a few kind of miscellaneous things before we wrap up.

Yeah.

This might be nothing, but you referenced somewhere this book, this art school book called The Decisive Moment by Henri Cartier-Bresson. I'm not butchering that name. And you said it's on how everything is about timing. What does that mean?

I love that book. It— first off, it has a beautiful cover. Okay. Um, second off, it's all about, uh, basically his approach to watching the world and waiting for the exact moment to capture the shot. And there's something about—

we were pointing out earlier.

Exactly. Yeah. And photography, I think of as like, usually it's taught as there's framing, there's lighting, there's composition, there's all of these different things. But the decisive moment, the actual timing is one of the hardest to nail. And he's a master at it. Like you look at every shot and it's caught midair, just ecstatic expression, whatever it might be.

A medium of timing in many ways, photography.

Exactly, yeah. And I think it's a patience and it's a presence that enables him to get that shot. And I always am reminded of that, of like, wow, he must live, if I think I'm living in first person-ish now, he must live in like, I don't know what, like first person times a million because he's so—

It's like zero person.

He's just there. Exactly. Yeah, he's just like pure presence, which I think is so special.

Ah, that's amazing. You often reference him, so I figured I'd ask, what do you love about C.S. Lewis?

I think he just taught me a lot about love and Christianity. And I think him being so open with his journey and his path, is something that I found deeply valuable in his level of honesty with the world. And I think it's inspired me in some ways to do the same.

What do you love about the film Magnolia?

Oh, it's so weird. It's so weird. It's so weird.

Paul Thomas Anderson for—

He's one of my favorite ever directors. I watched it when I was very small, and I think it just taught me how expressive and strange the film medium can be and how masterful it can be to intertwine a bunch of stories. It's basically, for context, like, it's a bunch of different storylines that then could join into one very strange moment. And I just, I felt deeply moved by it. And I was also like, this is someone's really weird mind that they just inflicted on me, and they're not even trying to really tell a story that makes sense or have a message. No, not at all. And I loved that. I was like, to me, it was the epitome of like, you could just do something at the like peak of your craft with excellent actors and like beautiful cinematography that kind of makes no sense.

By the way, after Boogie Nights, like, you're supposed to kind of— like, this is supposed to be like, you're— you made Boogie Nights, you're ready to rock. Now he got weird.

Yeah, he's just like— it was— it— the embodiment to me of like, um, the saying in the film industry where they're like, make one for money and then make one for art, and then one for money and then one for art. This is like very clearly he's one for art, and I loved it.

You had another quote about films that I found And I was wondering why it stood out to me. Uh, it's Patrick Cavanaugh. He says, the second grade films, where are they? No more are they made. And yet they were by far the best films for holding hands at. And wasn't this always the main purpose of the cinema? Where this got me thinking was like, in modernity— well, that's at least how I started thinking. And then I was like, well, actually, maybe it's not modernity, maybe it's just me, or it's my modernity. Art and media are like the object.

Yeah.

Like they must be the source of interestingness and they must be experienced rather than like a backdrop for my experience.

Yeah.

And yeah, I'm curious what your relationship, like people like us who are like, want to deeply study the things we care about, like the temptation is like everything has to be Magnolia.

Totally.

I'm curious what, to the extent, Is that resonant? Like, to what extent of any of you? Also, I should note, like, reading through so much of your writing, like, you are— it's kind of frustrating because there's my read-it-later list has like 20,000 things on it, but you are an amazing curator. And so as someone who consumes so much great art, like, do you have like— it's maybe related to like the slot, like not slot, but like basic content or content that isn't intellectual.

Like, yeah.

You see where I'm getting at? I don't know.

I don't really know. I totally do. I think I, um, I love normiecore stuff.

Yeah. Yeah.

And that's what that was getting at. It's like that quote. I was like, yeah, he got it. Like, I love weird arthouse films, but I also love, like, I don't know, trashy superhero TV shows. And like, it also just like the most popular TV shows are mostly popular for a reason. Like, I just don't, I've learned to not overthink a lot of areas of my life. And I think media and films and blog posts are one where like I do like to have both the— it's almost like a balanced diet is like a bit of the avant-garde and then also like a whole bunch of just like what everyone else is talking about because it's probably pretty good actually.

High and low together.

Yeah, and it's cool because you'll see that sometimes they're just talking about the same thing but in different terms. Mm-hmm. Indeed.

This is you on meaning. The blessing and curse of modern life is that an unprecedented number of us are now able to assemble our life signifiers, satisfaction sources, and meaning makers à la carte. Do you think this is a blessing in reality at all? Is it a blessing at all?

It's funny. I feel like I, I think I wrote that many years ago and I have since converted to Catholicism, which is like an interesting kind of counterexample to that. I think it's, it's much harder actually. Yeah. I think it's, it's beautiful in the sense that like my upbringing probably couldn't have been anywhere near as, as free and open as it was if it had been like 50 years ago or something. Like growing up in a small town and by two hippie parents, it was very like, you can kind of just live however you choose. And that was— that felt like a great weight, but it also inspired me to be much more interested in all the different options, I think. And so I think that that, that was quite special for me. And also feeling like I wasn't tied down. There wasn't anything that I wasn't going to have to choose myself. So everything that I chose had great meaning. It wasn't handed to me. Um, and so I think that that, that's special. And I hope to give some parts of that to like my children someday. But I do think that it was on the whole hard to figure out like what are morals and what does it mean to be a good person. Exactly. It's a lot. Yeah.

Leads right into my next prompt, which is— this is also you— where I work in a small subset of Silicon Valley, it's common for belief to be turned inward. Founders are taught to possess enough faith to will whatever they're working on into existence, but are rarely reminded to worship anything but themselves. This creates a pressure cooker of responsibility that distorts reality to the point that they often find it hard not to confuse themselves for God. And we all know how that ends. So far, my main learning is simple: the best belief system is probably the one that makes you more of the person you want to be. How has your faith in Catholicism changed you?

Um, it's made me much more external-focused. I think it like gave me the lens of—

It like fills that hole.

Yeah, exactly. It gave me the lens of like seeing like how, you know, their framing of it is how can I serve other people, but mine is more like how can I connect with and like help other people. It's the same thing. And I think it also just, it gave me a sense of not being aloneness that comes from being part of community that is global and a belief system that actually has like pretty clear morals around what it means to live a good life. And I found that I, I agreed with those. I loosely agreed with those. And so I think it was, it was very resonant for me from the beginning, and I think it's just made me much more confident in those beliefs of like, this is how I want to live and who I want to be.

You've called— or maybe this is— I think maybe got from somebody else, but like, life is a series of projects, this framing of life.

Yeah.

Are there any Molly projects that are bubbling up? Are there any creative side projects? Anything that has been— is it all Moth Fund?

I've been really into making jewelry recently, so I was learning how to, like, set stones and stuff like that and starting in on a project of, like, making different pieces for different friends and then naming it after them. Wow. Which is really fun. To like collaborate with someone that you love and then you get to make them this thing. I, what have I also been doing? I have been making a lot of cyanotype prints, which is like a certain type of photographic exposure paper where you put objects and you expose it to light and it's this beautiful cobalt color.

Oh yeah, it's the blue print.

Yeah.

Very similar to Dialectic Blue if I don't say so myself.

It is actually.

Yeah.

They're gorgeous and I love making them as like prints to give as gifts. And I think I just always have to have like a craft that I'm playing with, because otherwise I just feel like I'm floating into the abyss. Just helping people is not enough. I need to be occupying my hands.

Intangibility.

Yeah.

Can you make the case for calling people over texting?

Mainly just that you will hear so much more context on what their life is like than what they'll just share over text. Like you'll hear all kinds of weird noises and then they'll drop their phone and they'll be like, oh sorry, I dropped you. Yes, yes. There's something just really beautiful about that.

Higher resolution, higher resolution, even if like, yeah.

And I say this as like a Gen Z that like hated calling for my entire life.

Avoidance again.

Exactly, it's totally avoidance. And then you actually start doing it and you're like, they were right, they were always right, I should have called.

They both. What, as a self-proclaimed 10,000-hour expert, what do most of us need to know more about when it comes to apples?

Pink Ladies are the best. Envy's are the second best. Pink Ladies are the most dependable anywhere you go in the world. They're like a trademarked type and they will be very good. Envy's are more variable. There's a whole bunch of other types that I'm still trying to find, but those are the two that will like always be good. Always avoid Gala apples, um, the yellow ones. Any yellow ones I don't believe in. Uh, the really small ones are really tasty and really— they taste kind of like berries. And I just think apples are a— they're a perfect food, that's all.

For any reason other— it might— it's perfectly valid— for any reason other than narcissism and the coincidence of you and your name and your life and the person you married. Um, to what degree is there anything special or symbolic about the letter M?

I just think it's a very cool letter. Like, it can be turned upside down, it's a W, and it becomes a zigzag if you put them all next to each other, which is very cool. And you can use it as— Mmm means affirmative or thinking.

Oh yeah, I like that.

Yeah. I've just always, I don't know, I've liked making worlds around myself and the things that I make.

Pretty amazing you married a person with an M. Like it feels pretty deterministic. Yeah.

Yeah. Yeah.

If you guys, if you haven't looked at Molly's blog or her fun name or her initials, there are a lot of M's.

A lot. I really like alliteration.

I have a few final quotes that we can take one at a time. First, Annie Dillard. We can live any way we want. People take vows of poverty, chastity, and obedience, even of silence, by choice. The thing is to stalk your calling in a certain skilled and supple way, to locate the most tender and live spot and plug into that pulse. This is yielding, not fighting. A weasel doesn't attack anything. A weasel lives as he's meant to, yielding at every moment to of perfect freedom, of single necessity. There's a, maybe I have this wrong, but there's a contrast between stalking your calling and yielding.

Yeah.

How do you relate to that?

Well, first, I think that's like one of the best articulations of vocation that I've ever found.

Stunning.

I think stalking is like you have ideas and you're letting your ideas kind of guide you to places.

You're like sniffing.

Exactly. You're like, it's probably more intellectual. And then yielding is more like actually just accepting what is true from your heart and dropping the shoulds. Dropping the shoulds, exactly. And realizing like, this is probably the thing that I've always been kind of good at my entire life, and maybe I reject it or whatever it is, and now it's back. And I'm like, is this really the thing? I wish it were something cooler. But you're like, damn, it is a weasel. Exactly. I'm just a weasel. And it's the yielding, I think, that's often the most powerful. The stalking is like, it's useful to get out of your system because you often have all these ideas of like, I might want to be this or be that. For me, it was like being a director, being a designer, being a whatever it is. But then I think yielding was more about like realizing that like, I do really like the, the peopling and getting better at understanding people and serving them. And that has always been true.

Yeah.

And I do also really like making things, and they can be roughly divided, but I do think that the the peopling is more gratifying for me at this point in my life. But I think accepting that, I was like, is this really the thing? Like, isn't there something cooler?

Right, right, right. Yeah, it's a looking and then like the— there's still an openness. Like, I think that the front end of that is important, which is like you have to actually be aware, like looking and open and blah blah blah. But then I think a lot of people have the disposition of being open, but they're like looking at the thing in the field of view and they're like, well, it's not that.

Exactly. Yeah, yeah, yeah. They're like seeing it come again and again and again. They're like, no, couldn't possibly we'd be dead.

I think Simone Weil was right when she said that the, quote, love of God is pure when joy and suffering inspire an equal degree of gratitude. How do you practice gratitude, especially maybe for the non-joyful things?

Well, I think I enjoy feeling things deeply, and I always have. And I think it's one of the characteristics of being a 4. And I think that suffering feels meaningful to me in a way that, like, I don't try to escape it. Um, I think joy I've been more skeptical of until more recently— of recently. But I do think that finding that balance is something that I'm still striving to, to do, because I think suffering has historically felt more real to me than joy. And I think now it's getting to a point where the joy is around more often. So I kind of have to accept that it is real. And when the suffering does come, it's like, well, this is real too, but it's not— trying to get to a place where I don't see it as coming and being like, oh, finally it has come and this is the real thing. I'm relieved that it's like, it's back. Do you know what I mean?

Yeah.

So I think that that for me is like a funny, weird tension that I think is like some people might share, others might be more used to the joy, but it's like whichever one you lean more towards, you feel more comfortable.

That's how I framed the question.

Exactly. Exactly. Like, how do you get more comfortable with the other one and like believe it to be real too? Because I think that's the thing for me is like constantly kind of questioning of like, which one is like the truth?

I have one more thing. And it's funny because we talked a little bit about maybe the lowering this, the pressure, lowering the preciousness earlier. But two quotes, one from you. Basically, I believe that some things in life are strongly resonant yet utterly indefensible. Such things are a big part of what makes life feel special. Unfortunately, these same things often decay given too much scrutiny or optimization. And I think you were writing that in this context of preciousness being worth protecting. And then a quote from Goethe: Encourage the beautiful, for the useful encourages itself. Why is beauty virtuous as an end?

Because it makes us feel. Makes us all feel. And I think that that in itself is worth a lot. And I think for me, beauty has been like a core theme that I— to all of the things that I've done, I've just always been very drawn to it. And I think it's true of many other people too, if they kind of just let themselves feel it more. I don't think I'm the only one.

Molly, that's all I got. Thank you.

Thank you. It's a pleasure.

Thank you for listening to my conversation with Molly. Before I leave you, I'd once again like to thank Notion. For being such an instrumental part of making Dialectic possible. Uh, I partnered with them at the end of last year and it's just been amazing to have more resources and leverage, but also get to bounce ideas off them. And more than anything, use Notion to make the show better, whether that be research, uh, before the episodes or going in afterwards, pulling out ideas, lessons, patterns that stand out to me. And again, you can check out Notion at dialectic.com/notion. If you missed it, I also did a little fun Q&A with them on Instagram. Talking about how I'm thinking about the year to come and what I'm hoping to build with Dialectic. I'll link to that in the description. And once again, at dialectic.fm/mmm, you can find all the links, transcripts, Notion info, and more. Thank you again. If you enjoyed the show, please give it 5 stars on Spotify or Apple, or like and subscribe on YouTube, all the places. Thank you for listening and watching.