38. Molly Mielke McCarthy - The Art of Peopling

·Investor, Writer
Molly Mielke McCarthy - The Art of Peopling

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Description

Molly Mielke McCarthy (Website, X, Substack) is an investor, writer, and founder of Moth Fund, an early-stage fund focused on backing "moths": quirky, quiet, mission-driven founders who are often underpriced by traditional venture capital.

Molly's career has been a dance between "peopling" and making. She's held design, product, and editorial roles at Figma, Notion, Stripe Press, and The Browser Company, and explored film, photography, and the arts before finding her way to venture, where she started as a scout for Sequoia Capital. Today, she invests in people at the earliest stages. She also writes beautifully about agency, vocation, discernment, and what it means to live an authentic life.

We begin with how Molly identifies exceptional people—her "three-month rule," spikiness, and why competence is harder to find than storytelling. We discuss the bat signal she sends to attract founders who feel misunderstood, and one of her central distinctions: agency versus ambition, or why playing your own game matters more than playing games others have created. We go deep on commerciality and why it is so essential, and talk about how Molly's work as an investor often looks most like coaching. We also explore legibility versus illegibility: the freedom in not being easily understood, and when it's worth becoming legible. Molly's one of my favorite thinkers on self-knowing, and we talk about how she's navigated uncertainty toward authentically shaping her life and work into a form that fits her.

Molly embodies rare combinations: people-centric yet fiercely individual, intuitive yet pragmatic, truth-seeking yet full of care. I hope this conversation inspires you to yield to your own calling, and to be patient enough to see what's true about yourself and the people around you.

Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams build their best work. Notion is also where I compile research for episodes and the home of my new site where you can find all links and transcripts. My “What are You Building This Year feature with Notion on Instagram.

Timestamps

  • 0:00: Opening Highlights
  • 1:29: Intro to Molly
  • 3:36: Thanks to Notion
  • 5:14: Start: People, Spikeyness, and Discernment
  • 21:36: Agency and Ambition
  • 34:45: Commerciality
  • 49:19: Investing, Feedback Loops, and Creating a Bat Signal
  • 59:46: Coaching and Working with Young People
  • 1:06:54: Self-Knowledge, Uncertainty, "Should," Others' Acceptance, Motivations
  • 1:16:38: Illegibility & Legibility, Principles, Authentic Service
  • 1:29:28: Friends, Seeing in the Third Person, Femininity in a Masculine World, Love
  • 1:42:07: Grab Bag: Art, Catholicism, Gratitude, Beauty
  • 1:58:58: Thanks Again to Notion

Links & References

Transcript

0:00: Opening Highlights

1:29: Intro to Molly

3:36: Thanks to Notion

5:14: Start: People, Spikeyness, and Discernment

Jackson: Molly Mielke McCarthy, we are here. Thank you for doing this.

Molly: I’m delighted to be here.

Jackson: We're going to start with something I know you know a lot about: people, and particularly exceptional people. I’ll start with a quote from you: “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 meet one?

Molly: I think it’s more feeling-led than anything else. It is something about them that creates this feeling of never having met anyone with that combination of qualities, experiences, and characteristics before. I look for them pursuing excellence and actually attaining it. I look for some kind of flywheel around competency that is hard to find. One of the underlying premises of Moth Fund and my approach to people is that competence is hard to find, but storytelling can be taught. That guides where I spend my time as someone who can help with storytelling.

Jackson: Is there a minimum viable threshold of time with someone, or things you need to know about their background to be able to get to that feeling?

Molly: Three months.

Jackson: Really?

Molly: It’s very, very clear.

Jackson: You’ve done a lot of this.

Molly: I’ve done a lot. Anything less than three months doesn’t give me an accurate representation of their slope of growth, and I care a lot about that. My job as an investor with my strategy is to find the strangest, most spiky people and see which ones start to gain momentum and take off. I like to see them getting better at all of the things they were previously not good at and tackling things that were previously holding them back. Three months is a pretty accurate representation. If they’ve made no progress in three months, they’re probably not going to in the next three months either. I’m open to all the different ways they could change. It’s not necessarily just company progress; it might be a personal milestone in how they’re thinking about things. Typically, I know people that I invest in for a minimum of a year, but three months is what I look for to get an accurate barometer before I can say they’re exceptional. It’s just harder to say otherwise.

Jackson: Does it have to be first-party data? If someone you trust has known this person for a year and you’ve only known them for two weeks, can you substitute that?

Molly: You can, but the quality is only half. It should only be accounted for as 0.5x my own experience.

Jackson: No one knows what I’m looking for like me.

Molly: I want to see that the people I respect in my network are impressed by them, but I also want my own evaluation. It tells me a lot about the person I’m trying to get to know and the person who spoke highly of them. There’s a lot to be gleaned there, and if you just take it verbatim, I’m not developing my own taste.

Jackson: One thing that has continued to come up in these conversations about taste is that a very core input is eating lots of food. It’s easy to get lost in the sauce of ideating about it, but you have to taste. Let’s not forget what that literally means.

Molly: Absolutely.

Jackson: You mentioned spikiness. That has come up a lot in your writing, and I resonate with it. You describe it as wanting to understand what a person’s greatest strength is and how that functions doubly as their greatest weakness. That’s a common trope, and it’s poetic, but I’m curious how it actually shows up and how you learn to see that, especially in this three-month period where you’re getting to know someone.

Molly: I’m trying to understand their core competency, almost like the dominant leg they lead with, and how that makes their other leg weaker. People show you how they allocate their time. Most people are much more comfortable spending time on the things they’re good at. If you look at the stuff they’re neglecting, it gives you a lot of signal on what’s really going on.

Jackson: Many of the people you spend time with and eventually invest in, you meet when they’re very young.

Molly: Definitely.

Jackson: They’re not well-rounded by default. They’re probably not doing their laundry. Analyzing that in a thirty-five-year-old would be different.

Molly: For the young people I spend most of my time evaluating, I’m trying to understand their growth trajectory over those three months so that I can accurately predict what it’ll look like in ten years. People give you more signals on that than you’d expect. You have to listen a little bit closer to what they’re telling you, what they’re not telling you, and how honest they are with themselves. I’ve never set out to look for people who are fluent in therapy-speak, but I am looking for a person who fits my archetype of how I could help them. It is the one who spikes in competency, but maybe storytelling is weak. I call that a moth: a quirky, quiet missionary. You have to have humility when evaluating young people because I’ve been wrong as many times as everyone else. It’s realizing how often our own judgments and how we see the world cloud our vision of the person in front of us. That pursuit keeps me motivated to keep showing up: figuring out the person I’m evaluating while figuring out what I’m learning about myself in the process.

Jackson: What am I putting into the observation? One of the things I love in Graham Duncan's “What’s going on here with this human” approach is realizing the ways you, as an interviewer or investor, might be totally warping the context a person is in.

Molly: Absolutely.

Jackson: Thus, you’re getting a wildly unreliable perspective on them. On the spikiness note, you have a few paragraphs I thought were interesting that I’ll read quickly. First, you say: “The main commonality tying all my friends together is how incredibly individual we are. Each of us was designed to work on specific things in the world that we must first do the work to reveal to ourselves. 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. It seems like you’re saying spikiness is a trait, maybe even a burden, that is best reserved for founders, while the rest of us aim for generality. Or am I being too prescriptive there?

Molly: That pretty accurately sliced it down. 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. They care a lot about it and feel the need to almost exercise this vision in their head. The people that I find myself most gravitating towards are the ones who are actually more focused on living well. For better or worse, I deeply enjoy serving the people who have a mission to embark on, but they’re not necessarily the ones that I want to spend all my time with.

Jackson: They probably don’t have the time to hang out with you anyway, or hang out with anyone.

Jackson: It is interesting to wonder about. There are probably people who, at the beginning of their career, started off as very spiky. To take an extreme example like Mark Zuckerberg, they have gradually figured out how to add color or resolution to that picture as it’s needed.

Molly: I wonder if you got close to him, have his spikes dulled a bit? Or have they remained razor sharp, and he’s just filled in everything else with money and help?

Jackson: The way I’ve used spikiness to describe people is a bit different. I like to spend time with spiky people, but not quite in the way you’re describing it, which is this almost one-dimensional. I like people who have several spikes. I like those people much more than I like people who are very well-rounded everywhere. But I don’t like people with only one spike.

Molly: That is a very good point. In practice, the people that I spend the most time with are T-shaped. The ultra-spiky, one-dimensional people are typically just very young. As they get older, they turn more T-shaped or polygon-shaped.

Jackson: Brie has a metaphor of the fork shape.

Jackson: You mentioned moths and the notion that you're working with people who aren't totally legible. You also describe magnetism as a really valuable trait that you're looking for. What makes people magnetic? Particularly, how do you think about that in the context of people who might not be the most legible yet?

Molly: My core belief is that magnetism is a byproduct of authenticity and just living as you were intended to on the thing that you were meant for. I am a really strong believer in the pure concept of vocation, meaning that there is a right thing for people to be working on.

Molly: There’s a version that is large-scale, which you would ascribe to the hottest startup. That is less interesting; it’s a commercial magnetism that is produced by a team. Then there’s a smaller-scale magnetism that one person has. That can either be charisma, or it can be them actually just being deeply authentic. Charisma is usually a skill and a bit more performed. Authenticity in that form of magnetism is much more durable, and it doesn’t drain a person in the same way a performance does. It’s also innately, quietly, and deeply attractive to the right people and not to the wrong ones. That’s the kind of magnetism that I’m looking for at the earliest stages.

Jackson: You could imagine how a fairly introverted, nerdy person could be very magnetic in a specific way.

Molly: Exactly. If you get them talking about their favorite part of the nerd world, people just like them start swarming. They recognize them as one of their own.

Jackson: It goes back to your point about competence. Radical competence, knowledge, or curiosity is compelling. You can catch the thing that makes someone’s eyes light up when they go deep on a subject.

Molly: It’s very compelling. To the wrong people, they don’t even pay attention; they wonder what you are going on about. But those were never the people that you should spend time with anyway.

Jackson: You mentioned trajectory. You've written: "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 explicit that they aren’t betting on who I am now, but on the future version of me that sees success from sticking to this." You also say: "Discernment can be glimpsed in their reflections. They should have exchanged their innocence for wisdom, not just experience." That is really powerful. How do you start to see the potentiality of that, particularly the ability to trade innocence for wisdom? Everyone trades innocence for experience if they stay on the track.

Molly: It usually just comes down to mining the wreckage and the wins of your experiences and learning from them. Self-reflection is what turns experience into wisdom. That self-reflection should extend beyond just yourself. It’s not just about what is it about me; it’s also about what is it about the world and what is it about other people that I can learn from these experiences. That is the kind of help and support that I like to provide to founders in this quasi-coaching relationship. We look at how you can grow faster in the direction that you want to grow. I find that to be an endlessly interesting question. It is much less constrained to how you build a startup. Maybe you shouldn’t be building this startup, but that is the thing we should be talking about, not what the next product to build.

Jackson: This gets you closer to the vocation thing. You also talk a lot about discernment, which I think is really close to this.

Molly: Yes.

Jackson: Discernment is, as you say, not just seeing yourself clearly, but seeing the context, the world, other people in the situation, and all of it clearly. It is also about being able to drop a thing and not just stay in the inertia of it. I feel like that is part of this.

Molly: Discernment is the ultimate goal that I hold up in my mind in really everything I do, but especially in my investing and in what I call the peopling part of my career. How can I pick people, support people, and help them grow? In doing so, it’s about being discerning about which ones I pick. That’s the obvious part of the investor relationship. But to me, it’s really about being discerning about how I help them. 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? That’s just as interesting as the picking. 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 and how they feel about their work. I think that’s very impactful at the beginning stages.

Jackson: There’s a stewardship of that position that acknowledges that. In many cases, it won’t matter that much. But you are in a position where you could significantly affect somebody’s situation, life, or direction. It’s almost like carrying that weight—understanding the weight of what you’re carrying.

Molly: I try to wear it lightly, too. I have definitely gone through phases of thinking this is way too much responsibility, and then I feel like I’m overthinking it and it’s not that deep. But I do think there is something about accurately reflecting back a person at the beginning stages of them working on something that could be their magnum opus. It can be very deep.

21:36: Agency and Ambition

Jackson: 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?

Molly: 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 yourself—what you’re feeling, what you want, and what you need—you can have something that people might call agency, but it’s not very authentic to you. It’s making moves in the world that move you in a direction, but is it even the right direction? Part of my definition of agency is something that is true to you and true to where you should be going and feel destined to go.

Jackson: You have another quote that is along these lines: "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.” The presence thing is interesting to me because there’s an intuition that agency is about knowing what to do in the future; it has a future orientation. How do you think that distinction between ambition and agency affects how people should interpret the classic phrase, “you can just do things”?

Molly: So many agentic people are actually just deeply experienced in doing things, and they know that the possibility is there. They become more aligned with what they want to do and the game they want to play.

Jackson: Because they have a high feedback loop.

Molly: They have a high feedback loop. They have been doing things for a while. Ambition is usually more like doing things on a tracked path that will get status or prestige. That was my core thesis for Moth at the beginning: the difference between agency and ambition. I wanted to target people acting from agency because I thought they were undervalued. Over time, I’ve realized that it’s muddy. It’s nice to make a neat distinction on the page, but in practice, ambition is often deeply intertwined with agency. We are status-minded creatures. It’s not always clear what is a game that someone else set and what is actually the right game for you versus one you have to make from scratch. Part of realizing I was a bit black-and-white in that thinking is realizing that I see the world as an individualist. I really care about doing everything my own way and never wanting to play someone else’s game, but most people do not feel the same way.

Jackson: And there are bonus points for being purely original, like being the most special snowflake.

Molly: Absolutely. It’s a beacon for other people; they like to see it. But I don’t think it’s necessary at all. There are good stock games you can play that are the right fit for what you want to do.

Jackson: Totally. And there’s a huge gradient. The Overton window on what is unique or off the beaten path is moving. Ten years ago, Y Combinator was pretty weird; now it’s closer to Harvard. That is always gradually shifting.

Molly: That was a lot of the thinking behind Moth at the beginning. I saw an abundance of capital for people who were credentialed and legible—those who went to Stanford or held certain positions. But there was another type of person who wasn’t following a linear path and wasn’t legible. They were consistently underpriced until they built something that proved how good they were. There is a long period before they’ve built and shipped something successful where, if you met them and got to know them, you could still see in their eyes that there’s something very deeply special about them.

Jackson: It might take three months.

Molly: It might take three months, or it might take a year. But it is deeply worth it because they are the ones whose trajectory you can really change. From a purely financial perspective, they are underpriced until they have shipped something real.

Jackson: One last thing on agency. You have a line where you say, “I want all of us to know just how much ownership we have over the future.” It is a beautiful way of framing the positive side of agency. You also have an articulation about the inputs to agency. Can agency be improved, particularly in adults, or is it fixed? You describe the hook, the catalyst, and the sustainer as the frames of inputs for increasing it. Do you think that holds? Would you amend it? As you have continued to do this, do you have an updated sense of how someone can go from not that agentic to somewhat agentic? Once you get into the agentic loop, it starts to compound. I’m curious if anything stands out.

Molly: I was very idealistic when I wrote that in 2022. There is some truth to it, but I think it is pretty capped. People can be inspired by someone else’s story, try something out, and then be in an environment filled with other agentic people to get to a slightly different baseline. But it is hard. My counterargument comes from seeing people from other environments who are no longer young. If they decide to move to the Bay Area and get into startups in their 30s, it is quite hard to change their attitudes about the world. It is possible if you are open-minded enough, but very rarely are people that open. I grew up in an environment full of hippies who were constantly thinking about how to change the world. It was about constantly figuring out what was wrong and finding the solution.

Jackson: It has the same tenor of opening things up.

Molly: It has the same tenor of, “let’s just do things.”

Jackson: It is very California. It is no coincidence you didn’t grow up in Silicon Valley.

Molly: I grew up in a small hippie town. Growing up there made me think all people have a higher level of agency than they actually do. I have since chased environments where the people are agentic, interesting, unafraid, and original. I was drawn to film first because I was around directors who were building a world. In the same way, once I got into tech, I saw that these founders are also building a world.

Jackson: Both fields are very entrepreneurial.

Molly: There was something deeply interesting and compelling about both. I wanted to help, be a part of it, and help them refine, calcify, and grow. I have been lucky to be in environments where it was encouraged to be ambitious, to do things, and to take risks. A lot of this learning has come from being in other countries and visiting friends’ home environments. I learned that the rest of the world is not at all like what I thought it was.

Jackson: I’m reminded of one other thing. You cite David Brooks describing the theory of maximal taste. 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 maximal taste says that each person’s mind is defined by its upper limit: the best that it habitually consumes and is capable of consuming. Your main point still stands on a relative basis.

Molly: There is something to that. It is probably only true for people who have already self-selected for agentic environments. Those who choose to fill their minds with things that push the bounds are going to grow.

Jackson: It’s interesting. I talked with Brie about this as well. We were reflecting on these really impressive people when they’re really young. Usually, it’s very clear when you’re twenty. I was not in an environment where there were fifteen-year-olds doing startups. I went from a world where you really don’t know what great looks like until you see it. Environments are powerful. Perhaps the real answer is that most people have never even gotten close to an environment that would allow them to see how high the bar can be.

Molly: I think that’s exactly it. The bar doesn’t need to be just startups or your chosen profession; it could be in a completely unrelated field. Competence is impressive and magnetic, no matter what it is. You can just feel it. Even being around an amazing lawyer in their zone of genius allows you to see what is possible.

Jackson: But you would have to see the process in person.

Molly: You have to be around it, absorb it, and see how they spend their time, who they are, and how they relate to their work. So much of my career was a story of getting into tech and being lucky enough to be around excellent people. My bar was raised because I was suddenly given much more autonomy and agency than I had in any other environment. I decided I was never going to leave. It is a story of this happening to me and then me staying around because of it.

Jackson: The process—the “garage door up” part of it—is really important. I was chatting with a friend this morning about a Jerry Seinfeld line where he says all art is disguising work. It is like a magic trick. People are exposed to great things, but it looks easy. Maybe the key is actually getting to see the process.

Molly: I think it’s the process. Everyone can look up a Mona Lisa or any given masterpiece.

Jackson: Or even a great film or a great song, but you don’t see the slugging.

Molly: You don’t know what went into it, and you don’t know how the person making it was feeling about their work through the whole process. What were they doing? Were they micromanaging? Were they going crazy? That is the stuff that shows the level of sacrifice a person who really cares about what they’re doing puts in.

Jackson: I just read East of Eden by John Steinbeck, and I’m reading the letters he was writing while he was writing it. The main emotion I had was that he is just like me. Some days, he says he’s a genius and so good at writing. Other days, he says this suck,s and he sucks. There is an accessibility to it.

Molly: Absolutely. Seeing that they’re human and seeing the peaks and the troughs is a huge part of it. It humanizes it for people. Excellence can look like not always having a good day, but still just slugging and showing up every day.

34:45: Commerciality

Jackson: One of the more important traits, in my view, is commerciality. I think you express a similar view when it comes to early-stage investing, because it is less obvious. You have an essay called "The Lost Charisma of Capitalism," which describes the essence of this. You wrote, "I became obsessed with understanding the defining aspect of the successful entrepreneur, their commercial aptitude." You also wrote, "Commercial instincts are the result of exposure, perhaps even more than inherent talent." I'm particularly interested in that. Maybe it's like the agency thing. When people talk about commerciality, they talk about it as an innate thing, like someone who started their first business at six years old, selling lollipops. Yet you are saying it is largely a product of exposure. I'd love your perspective on commerciality, why it's so important, and that thread on exposure.

Molly: I define it as knowing how to capture the value you create and having a hunger for it. Highly commercial people typically see the world in terms of money, where it flows, and how it can be captured. They understand the world that way. It's their version of math in their head. I think that is something some people are born with, that quintessential entrepreneurial lemonade stand streak. That's really special. There are also many tales of people growing up in families where somebody else was more commercial, and they learned it from them. It can be the kind of thing where you join an early-stage startup, you are around a highly commercial CEO, and you pick it up from them. You see how it works, how they made money, and the hunger in their heart.

Jackson: I have seen the Matrix, almost exactly.

Molly: They start to see those opportunities out in the world for themselves. It really is a lens that you can acquire. Some people are born with it; others learn it from people. It's not as complicated as people think it is. I say that as someone who is not commercial and grew up with an anti-money hippie background. Now that I am working in venture capital, you can feel it when you're around people who are commercial. There's a hunger and desire there that is not just ambition; it's their view of the world. Even myself, I start to look around and see that these people have it and these people don't. I can see the kinds of opportunities they'd look at. If I were that person, I'd be interested in that commercial opportunity. I actually think it's a lot easier to train than agency 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.

Jackson: Maybe another piece that less commercial people might react to is a transactional nature or griftiness. You said most people do want something from you; it's just the timescale of their urgency that dictates whether the experience feels good or bad. After all, being transactional on the scale of a human lifetime is how most productive partnerships are structured. Can you talk about the specific positive sum bent on commerciality that makes such great entrepreneurs?

Molly: They are not looking to extract value right now. That is the main difference. People feel it.

Jackson: It's just patience.

Molly: It is just patience. They see that there is something interesting. They are drawn to you; there is some kind of kismet to the relationship. They understand there is something special here, and they're willing to wait around until it's obvious what it is. Most successful founders and entrepreneurs collect special people, and then they figure out how to slot them in. That is the same for investing, too. I collect special people, and then I see if it makes sense to invest in them. It is a certain style of thinking that is very people-centric. I was very surprised in my jobs how the style of thinking of the leaders that I worked for was incredibly people-centric, almost in a way that was similar to being an investor. Even though they were running an organization, it was completely different. They were still thinking in terms of recruiting as the most important thing and making this business grow and flourish. That requires talent. I was interested in thinking similarly: how can I find special people and support them in their growth. But I wasn't interested in having them build my thing. It was very clear that I shouldn't be a founder.

Jackson: It's interesting. You have this idea about "idea people" versus "people people." Entrepreneurs probably need to start as idea people. At some point, at enough scale, if you're trying to build something ambitious enough, you need to graduate into being people-oriented in terms of where your leverage comes from.

Molly: I totally agree.

Jackson: Certain investors can split both ways.

Molly: Many founders hate it when you say that. They believe you can be idea-centric forever. Your business is capped if you are thinking that way, because you're not actually thinking about it.

Jackson: Maybe we're heading into a world where people matter less, but I'm skeptical.

Molly: I'm skeptical too.

Jackson: You have this frame on truth-seeking people versus social-cohesion-oriented people. Do you still believe in that? I'm curious if that's another thing you've evolved your perspective on, or if it actually holds.

Molly: It holds. It’s a general thing I constantly ask when I'm getting to know a person: do they lean more in one direction or the other? Are they going to stay quiet even when they have something to say because they think it will disrupt the crowd? That would be social cohesion. Are they going to feel compelled to say it if they see the truth? If they detect that someone is lying, are they going to needle at it? That would be truth-seeking. That's very useful to know. Typically, most founders skew more truth-seeking.

Jackson: With that description, most people listening would assume you only invest in truth-seekers. But you actually describe Jeff Bezos as being a bit more on the social cohesion side in the context of being customer-obsessed. I'm really curious about that.

Molly: Social cohesion can look like being an amazing salesperson. The downside of someone who is very truth-seeking is that they can be very brash and hard to build a relationship with. They often lack the smoothness needed for sales in a given industry. Jeff Bezos is a good example. People who have built successful software in vertical-specific industries where they had to build a lot of trust with their customers often share this. Dylan Field of Figma is another good example. They aren't necessarily just social cohesion, but they definitely have that skill. They can bring it out and know when it's important to play that card. That is not possible for many people who are so truth-seeking that they can't even put that on. I'm sure Jeff Bezos saw many instances where things were not true, but he didn't have to name it and lose the deal. He was able to put on the salesman face and make it work.

Jackson: That is a much more interesting and useful orientation than simply wanting to be a truth-seeker. Transitioning to investing and the note of commerciality, you wrote about advice suggesting an investor is ideally a finance bro with a dash of Engelbart. You observed that Neil Mehta feels like a quintessential version of that. You also noted that you didn't change yourself to become this, but it inspired more commerciality in your career.

Molly: Exactly.

Jackson: Do you think you've grown in that direction? Do you think you've just gotten better at spotting it in the "moths" you look for? What has your relationship to commerciality been over time?

Molly: A framing I've been using recently is "in the flow" versus "out of the flow" investors. I am most definitely an out-of-the-flow investor. I'm doing a very strange, long-term strategy that really only makes sense for me. I find that deeply intrinsically motivating, but I don't really experience FOMO. So many investors are trying to be the in-the-flow investor, which means being very competitive and playing the game everyone else is playing. I have no desire to do that. Commerciality for me has always been about being my weirdest, most original, unique self. I want to attract people who see "like for like." They aren't necessarily like me, but they understand how I can help them. They might feel misunderstood, and we rise and win that way to prove that investing in moths is good business. My first fund was a proof of concept to prove my hypothesis of the type of person I think is undervalued and can be attracted early. The long-term vision has always been to legitimize that archetype, in the same way YC legitimized young technical talent and the Thiel Fellowship legitimized dropouts. Moths—quirky, quiet, mission-driven founders—are consistently underpriced. They come to their commerciality in a very roundabout way. They care more about the mission, but they want the mission to be rewarded, to exist, and to grow. You want to find people who are not just mission-driven artists, but who care so much about the mission that they realize they need the flywheel of making a lot of money.

Jackson: How do you find people who are more commercial than you? It feels important as someone who doesn't default to being very commercial. These people aren't always legible in a three-month period. It won't show up the way it would in someone more salesy, where the commercial part is easier to identify. What do you look for? You talked about looking for signs of growth, trajectory, and becoming resourceful, but this feels like a slightly different thread.

Molly: I think it's often looking at actual proof from the past that they can do it. If they are in the process of building the thing and in the early days of potentially getting money for it, how much do they care about that? Are they actually good at sales? Are other people coming in to help them get this thing off the ground in a way that is magnetic? That gives you a hint at their ability to sell. I think the ability to sell and being magnetic are usually one and the same.

Jackson: Sales comes in different flavors.

Molly: The flavor that I'm more interested in is mission-driven sales. This is where the person clearly cares so much about the thing and is so authentic in doing the thing they were meant to do. Of course, you want to work with them or give them money. But I do think that commerciality is actually something that you need to see proof of at the end of the day.

Jackson: Most people who verge on the mission-driven or authentic side, even if they're commercial, have a negative relationship to sales.

Molly: Tell me about it.

Jackson: Candidly, you've even expressed this with fundraising. What is that process like? What have you observed either in yourself or in watching the founders you work with? What is it like to improve the sales muscle? Does it mean becoming inauthentic, or can you authentically improve at sales if this isn't your lean?

Molly: I only came to believe that you can still be authentic and be a good salesperson from seeing the founders that I back doing it. I realized it was cope, and I should be doing the same. This is one of the main things that I help my founders with. It has always been easy for me to say that, of course, you should be getting paid for this. You should be getting paid way more. You should be advocating for yourself. Often, the mission-driven founder is the one who is a little bit more scared to put their thing out there. But they still have this hunger and desire to capture the value they create, and that's very important. It's very easy to be an outside observer and say you should sell.

Jackson: It's hard to do for yourself. It’s hard to take your own advice.

Molly: Very hard. It took a very long time for me to finally take my own advice and get better at selling.

49:19: Investing, Feedback Loops, and Creating a Bat Signal

Jackson: I have certainly experienced the lack of feedback loops in investing. People don't know it coming in and eventually realize it. You write that 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. Separately, you mentioned that Geoff Lewis has this funny clip where he says a founder should always choose investors who aren't using their investment in your company as a means to self-actualize.

Molly: I think about that a lot.

Jackson: I'd love to hear you reflect on that need to self-actualize. How does one get to this point of total ease in the ambiguity? Maybe it's very different doing that at a big firm versus on your own.

Molly: At a big firm, you have more things to distract yourself with, but at the end of the day, you're still left with the same question: it's not clear that I'm good at this yet.

Jackson: You're saying you have more artificial games to play that look like a feedback loop.

Molly: They are not. You shouldn't confuse yourself. The game of investing is always going to be whether you picked companies that made a lot of money. That is the best and worst part of investing because I love the fact that it's so open-ended. It means I can take whatever path suits me and plays to my strengths to get there.

Jackson: As long as it's about making money.

Molly: And you don't know if you'll get there. It's the existential anxiety that you have to learn to deal with. I felt it a lot more in the first three years or so. Then I got a bunch more markups. Not that they're indicative of anything, but they were early proof that there was something to my taste, and that proved out my theory of Moths. That's what I was looking for from the very beginning. If I'm very honest with myself, I don't care about anything except for the relationships with the founders. That is the part that keeps me going. That's why I do all of this. As long as I'm doing a good job at that, finding interesting people, developing deep relationships with them, and serving them in their growth, that's how I'm measuring myself. I can tell myself that it's the rat race of fundraising or being known in the right circles, but I don't really care about that. I don't find myself very impacted by FOMO. As long as I can evaluate myself with my own metric and see that I’m tracking, I think it will backtrack into the long-term outcome that I want. As long as I keep the main thing the main thing.

Jackson: At some point, it actually becomes legibly evident: you either made money or you didn't.

Molly: Exactly. You either know you should stay or you should get out.

Jackson: You had a bit about writing, investing, and the uncertainty inside both. You said the job of the writer and the job of a VC are quite similar in that they both ask you to produce an original end product. In the writer's case, it's articulated ideas and stories. In the investor's case, it's a differentiated portfolio with outsized financial returns without much of a map for how you get there. Professional writers complain about writing because it's really difficult to wrangle your brain into producing uniquely interesting thoughts all the time. It is highly frustrating when you consider it your job to do so. Making good investment decisions is similar, just with the added element of being highly social. Taking the quality of your self-talk seriously seems superfluous, but it is an investment that will result in better decisions.

Jackson: A lot of that is very similar to what we were just talking about. But I'm curious specifically about that last bit: the self-talk piece inside of all of this ambiguity and your ability. Granted, part of it for you may be less about coming up with unique ideas and more about finding amazing, unique people. What is that connector between self-talk, decision conviction, and ambiguity?

Molly: I think it's about not letting the FOMO get to you and not letting the self-doubt creep in. You wonder, "Was I right when I followed my hunch on that investment?" or "This person isn't taking off as fast as I thought they would; was I wrong about that?" It's actually about thinking less. The purest way of doing investing is not even doing it as your full-time thing, because you think too much about it. It's almost smarter if you have something else going on, like writing a book. If you want to go deep on ideas and make bets like that, it's a completely different story.

Jackson: Especially the people-oriented investing.

Molly: For people-oriented investing, you actually know whether you want to back someone after a 30-minute or hour-long meeting. In my case, it just takes me longer to get there. I have an inkling that I'm trying to validate. It’s much more productive for me to just continually show up as a blank slate and serve the people that I've backed in their growth, rather than thinking about much of anything else.

Jackson: It's almost like planting the seed and then getting out of here.

Molly: Yes, and keep watering it. But that's about it.

Jackson: Dialectic Clips - Pratikfor your podcast a while ago. There's an amazing part where he expresses that venture investors underrate counterparty risk. Traders understand it, but venture people don't always ask, "Why is this deal coming to me?" This points broadly at something you think a lot about: What is the "bat signal" I'm sending out there? What is the brand I've created that routes things to me? In early-stage investing, that's the only way to have any leverage or scale. Daniel observed that staying too top-of-mind in a broad sense might actually be a bad signal. You want your brand to generate as many nos as it does yeses. I think you've internalized this, and clearly you're very deliberate about it. It seems to be working for you. What is that bat signal, and how do you even know when it's working?

Molly: I think about it a lot. That is maybe the one thing worth stressing about as an investor: am I the product of adverse selection? That is a real existential fear worth thinking about.

Jackson: It's like, "Who said no for this to come to me?"

Molly: Exactly. My strategy was distilled after seeing what worked in my first fund. Fifty percent of the best deals came from direct relationships with founders. The other 50% were from people in my network who were eyes on the ground, deeply embedded in a domain. Usually, they were an operator or a founder who just understood what I was trying to do with Moth and could accurately describe it.

Jackson: They were taking your language on.

Molly: Exactly. The premise I give them is that if there's anyone "mothy" they meet, I would love to meet them. Ideally, they're not raising; they're just an interesting person thinking about ideas. I have different mechanisms to meet people. One is grants, under the premise of discussing a project they are excited about. Another is the coaching help I do around what they want to do next, whether they're deciding to raise venture or choosing their next move. I like working through those problems. I think they're very high signal. Another is just general helpfulness. You seem like a Moth, and there are not a lot of people like us, so I think we should get to know each other.

Jackson: Those all spin the flywheel.

Molly: They do. The ideal experience is finding someone who gets me. I want to transmit the mimetic "Moth" thing into their head so a bell rings when they meet someone, and they think, "You should meet Molly." I'm trying to give them a minimum viable definition of a Moth they can hold onto. Usually, that means they are one. It spreads between people who get it. The working definition of a Moth is typically people who feel misunderstood. They are mission-driven, quirky, quiet, or illegible. They could be summed up as being weirder. I try to meet all of those people and see which ones take off. Another filter mechanism I have in place is my writing. It isn't usually how founders find me, but it is frequently cited as a reason they wanted to work with me. It shows who I am. I try to be authentic and honest in my writing to show what I believe, how I'm going to help them, and how I see the world. If I'm not the right fit, they'll know that. Even when the referrer suggests they meet me and shares my writing, it saves everybody time. I do not take a high-volume approach. I tend to meet only qualified candidates I think have something interesting. That is just my preferred style of working. It's what's sustainable for me. I'm not a person who would thrive in the "go-go-go" style of investing.

59:46: Coaching and Working with Young People

Jackson: You mentioned coaching a couple of times, specifically about understanding people’s motivations and failure modes. You referenced the Enneagram as one of the ways to get better at this. I’m curious how else you’ve learned to improve in that area. Beyond that, what is the art-science gradient with coaching? It is a little different as an investor, but I think many people listening who have had positive experiences with coaching might view it as somewhat scientific, valuable, and obvious. Other people might view it as all art. Is there substance there?

Molly: There is a huge variety; some of it is terrible, and some of it is great. I have been very lucky to have a very good coach for most of my time working on Moth. She is trained in Enneagram, IFS, and all kinds of other things. That has been very helpful for me. I have learned a lot from her viewpoint and how she has helped me make sense of myself and the world. My bar has been set very high. This is what good coaching looks like: it is incisive and truth-seeking, but it is also deeply empathetic. That is what I strive to be for my founders. I am not anywhere near as good as her, but there is a deep lack of that approach in venture capital. There is a deep need for it, too. It is about being there with people and helping them understand themselves and what is going on in their heads and their companies. I came from a weird background with strange people whom I spent a lot of time trying to understand. I have always been interested in people. My career can roughly be divided into a bucket of "peopling"—understanding, discerning, and supporting people—and a bucket of making things. The making things bucket includes my film trajectory, photography, and art—everything I did that was about design and tactile or digital creation. Peopling is what I am focused on most now. The inputs are data points from the world. I strive to see every interaction as an opportunity to learn from and about a person. You get a lot further with people faster when you go that way. Even when we do not end up working together, I learn something new from each person. I am also a geek about the Enneagram and other systems like that.

Jackson: You express a lot of optimism, and you are good at finding "weird kids." Your work and writing convey a sense that the kids are going to be all right. You have an amazing essay called "How to Be a Kid That Goes Places" that I really love. You articulate how the archetype of the founder has evolved. One excerpt says, "I believe that good founders have been and always will be ns of ones. But what constitutes an outlier is dependent on where they stand in relation to all that came before them." That is a summary of what the piece is about. I have two questions. You wrote that in 2023. Are there any major archetypical updates to that type of person based on what you are seeing now? Also, as an investor, what is your plea for people that the kids are indeed going to be all right?

Molly: I am buoyed by meeting people who are doing it their own way. I attract and work with a lot of them. They work on ideas that are controversial, strange, and hard—definitely not B2B SaaS or usually an AI company. That gives me optimism because they are doing it in the face of so many easier options. It makes me optimistic to see that while many people get caught up in rat races—collecting credentials or fame—there is a whole other class of people that avoid it entirely and see it as a hoax. That is inspiring to me. I was confused at the beginning and had to figure it out; I was not as clear-sighted. There is a clear-sightedness to young people I meet today that comes from coming out the other end of nihilism. They decided not to think that way. They are going to build whatever they want and figure it out from there. No one can drag them into a stupid rat race. That gives me a lot of optimism. The archetype has evolved to become more high-variance. The young people who are successful at a young age are getting even younger. Everything gets pushed to greater extremes. Will the next founder be nine years old? You are still measuring yourself on the same rule sticks: age, how much money you made in a short span of time, or measuring yourself by which powerful people's ears you have. That is exciting, but I am more interested in how you are a person paving a path to a place you actually care about.

Jackson: Getting you closer to vocation.

Molly: Exactly right. Getting to the thing you were meant to do. All of that credential collecting and looking impressive is interesting, and it definitely benefits you in ways, but I am much more interested in people focused on doing something rather than being someone. That is the main thing I look for more and more. It is a very large green flag to see that they are doing that at a young age. It is hard to find.

1:06:54: Self-Knowledge, Uncertainty, "Should," Others' Acceptance, Motivations

Jackson: You write a lot about understanding yourself, at least you have in the past. There is definitely a pattern more toward doing rather than thinking and ruminating. Many people I enjoy reading and talking to have this introspection-agency connection, where they are feeding each other.

Molly: Yeah.

Jackson: I'd love to talk about the inward view and the self.

Jackson: Uncertainty is a common theme as you're navigating these excerpts. Emotional ambiguity does not need to make you anxious. You wrote, "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." I think we've all felt that. Finally, instead of a conclusion, you 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?

Molly: That's a great question. I think I have just built out a stronger baseline of the things that I can control, which are a stable group of people who love me. I'm very lucky to have a wonderful husband, and the life that we're creating together is something that brings me a lot of joy and stability. I think that has really raised my uncertainty tolerance a lot. Having that baseline be so strong has been incredible for watching how something can go wrong in my work or my life. It just doesn't feel that bad anymore. It's not crushing because it's no longer a sign that everything is coming crashing down.

Jackson: Not every incremental thing is causing everything to crash down.

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

Jackson: You have an amazing line from the end of an interview with Spencer Kier back in June of 2023, which I find a little bit paradoxical. 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 seeing the water on that? What is the thing you have the really firm grip on that you're not loose on?

Molly: I love this phrase that my mom used to tell me: stop shoulding yourself. What is the thing that you just keep thinking, "I should be this"? The clearest sign that you're onto what that thing is is that you're just beating yourself up all the time. You're procrastinating and avoiding shame. That's typically how I think about procrastination: avoiding shame or guilt. I think that is so often a sign. What is that "should" statement, and why is it so important to you? Why are you clinging to it? What does it mean if you were to release that and say, "I actually just don't need to be that anymore"? What happens? Do you get really scared? What is the reaction? Getting okay with that reaction is very hard and takes a very long time. I learned a lot about that through the process of my career. I thought I should still be the shining golden child in my career, and then I realized, "Why should I be that? Do I actually care about that at all?" And the answer was no, I don't.

Jackson: To the point of your original quote, it's often that you're holding that "should" so firmly that you don't even acknowledge that it's an option.

Molly: Exactly. You think it's just how the world is and that you have to be that way. That level of clinging is such a sign.

Jackson: This relates to the uncertainty thing. I have two quotes on other people's love. The first is from Jenny Slate: "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 authenticity and getting closer to yourself. Separately, you wrote, "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." I pulled those two together because it feels like other people's love is doing a lot of work on both fronts. How have you learned to accept other people's love and also not require it?

Molly: It was only after learning to accept it and live with it that I realized, "Actually, this is great, but I don't need it. I don't need to chase it."

Jackson: That's a painful realization. Do you have to get the thing to realize you don't want it?

Molly: Exactly. It would be amazing if you could shortcut that. I have been very lucky to be loved so wholly by both my friends and Tom, my husband. It taught me a lot. All of my reactions to that were the same reactions that I would have in a work context. There is something deeply true about the statement that the way you do one thing is the way you do everything. If things started to go so well at work, I would think, "Oh no, it's so bad. I don't even want this." That kind of self-sabotaging was the same reaction as when someone was too nice to me. You realize it's a "me" problem. This is dumb; what am I doing? I'm very lucky to have a good coach and people who could help me sort that out.

Jackson: I have another pair of quotes about getting closer to your motivations. Maybe it ties to the coaching work you're doing for other people. You said: "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."

Jackson: 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 is a beautiful way of articulating what true authenticity can do to allow for agency. In that first paragraph, I'm specifically curious how you reoriented your days to get closer to that.

Molly: Fewer meetings. It looks like spending more time with the people that I actually wanted to win. In a work context, instead of taking all the meetings to make yourself feel productive and like a good VC, spend time with the ones you are the most excited about. Carve away time for serendipity and scouting in the places where you want to find people. Save that time for going deep with the ones that really surprise you and that you really like. The right balance for me is far fewer meetings than your average VC per week. I need more time to think, to develop my theory of a person, to spend time with them, and to develop my own ideas about the world and how I see things. I need time to write. It was basically carving out time for that in a work context and carving out more time for my friends.

Jackson: It's almost like dropping "shoulds." You are dropping a lot of "shoulds" about your conception of how this is supposed to be.

Molly: Totally. Even in the context of friends, instead of forcing myself to spend time with lots of different people and having looser friendships, I am perfectly happy with five close friends. That is ideal for me. Accepting, embracing, and designing my weeks around that has been huge.

1:16:38: Illegibility & Legibility, Principles, Authentic Service

Jackson: One of the dominant themes that continues to come up in my conversations is the dance between legibility and illegibility. It is something you write about so eloquently in the context of your firm. I have a bunch of quotes that tie together. 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." Despite spending a lot of time helping others develop the skill, you felt strongly that making your story easily digestible to others would diminish your authenticity in a way that felt self-serving and wrong. Finally, you wrote: "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." That is a great case for illegibility. What's the difference between uncertainty and illegibility?

Molly: Illegibility is choosing not to make yourself understandable to the world. Uncertainty is not even understanding yourself, being uncertain about where you stand, and why you are doing what you're doing. With illegibility, you can have certainty about those things; you are just choosing not to share them publicly. There is a lot more power that lies in that today than ever before. It has become the norm that you should publicize anything you do right now, even what you did two minutes ago. You can learn a lot from actually spending more of your time doing the thing than talking about the thing. Part of my theory of Moss is to focus more on the people who are already spending time doing things rather than being someone. They get further faster and reach more interesting places. They have a deeper sense of who they are because they are not trying to package themselves to perform well on social media. I have definitely spent a lot of time on social media. I grew up on Instagram and spent a lot of time on Twitter during COVID. It taught me a lot about self-presentation and got me into rooms I wouldn't have been in otherwise. But I also very quickly started to feel like it was controlling me versus me controlling it. I have always been very sensitive to when it feels like a job or a platform is changing me. I feel that way about venture, too. I am here to deepen relationships with people who I think are going to really win. Venture is not going to change who I am. Does that mean that I'm less competitive? Sure, but I am playing a different game. It is similar to illegibility. It is about how you can continue playing your own game and finding your own voice.

Jackson: The implication for your founders and for you is that at some point, there will be a time for legibility. In a recent advice column, you addressed this dilemma. You wrote: "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 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." Ask me how I learned that. How are you becoming more legible? How are you doing that without letting it subsume you?

Molly: It is just very instrumental at this point. I was not the biggest fan of instrumentality before. I thought it was better to have long-term horizons and be less attached to the outcomes. In practice, I now see being legible as a chore. It is a chore to get on the stage, perform myself, and make myself clear to other people. It needs to serve me in some way. I am only going to do it if it is going to serve me. That doesn't mean it is just a story used to get money. But when I am writing a piece, it is to say this thing that needs to be said, for it to be clear what I stand for to these people.

Jackson: Yes.

Molly: I'll write the thing. It's very clear. It actually makes writing a lot faster now, too, because I know what I'm there to do as opposed to coming to the page and thinking, "What should I spend my time on now?" I do think there is some core tension that I still have, and probably will always have, between legibility and illegibility. To be clear, I wouldn't say I'm the most legible person. That is by choice.

Jackson: It reminds me of two things. One is the Beyoncé Sasha Fierce persona.

Molly: Yes.

Jackson: I don't think it's quite the point you're making, but it's related: you talk about adopting this persona of Dolly when you're writing.

Molly: Yes.

Jackson: There is almost a role-playing that makes it easier.

Molly: It's way easier.

Jackson: It makes it more instrumental, maybe.

Molly: Especially as someone who cares about something feeling like you, it's hard to loosen that grip. You think, "A person like me wouldn't write something bad." But if you put on an alter ego, they can write something bad. It's not you. It's fine. It's a funny mind loophole.

Jackson: So much of this is also about the fact that I think you are, in many ways, 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, particularly given that your job is to be around these really amazing people. Granted, maybe with the people you're investing in, they're early enough, and they're so mothy that there isn't quite this. Earlier in your career, you worked in several amazing companies, and I suspect you still spend time around really charismatic, compelling people. How do you not get sucked into the gravity well? How do you maintain that sense of distance? You are dancing in and out.

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

Jackson: There's an ease in not needing to feel like you need to compete.

Molly: Exactly. I let go of that probably three or four years ago. This is not—even when I do win, it's empty because I don't even care. I was measuring myself by somebody else's rule stick. That is something I remind myself of a lot. But I also think I've put myself in a corner where I'm not really comparing myself to other people very often. If I'm comparing myself to other investors, we're both being evaluated by whether our investments five years from now make a lot of money. So it's not clear. It's hard to be competitive in that way. The insider and outsider point is something I still think about a lot. I was able to become a bit of an insider at a point in my life when I was more open to changing myself. I've benefited a lot from that. Now it is a constant dance and tension between how much I still care about the things that the insiders care about and what the compromise is. How can I still be myself and still be an insider?

Jackson: Right.

Molly: I benefit a lot from being in Silicon Valley, in startups, and connected in a way that can help me raise a fund and invest a fund well. I can't get too fringe, if that makes sense.

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

Molly: It is.

Jackson: It's like a balance.

Molly: Totally.

Jackson: You published a list of personal principles back in April of 2023. There are five of them: 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 are there any amendments or observations you would add? Have those held?

Molly: I think they've mostly held. I think I'm less precious about preciousness. I've become more truth-seeking over time, which is interesting. I've just become fed up with not saying the thing. I've realized that I'm much more punchy on the page. I just say what I think. I've always found that very easy. I've been writing for my whole life. I've always found it very easy to be very direct in conversations with people where we're seeking truth on what is true about them. I feel like I'm in my zone of genius when I'm doing that. I used to be a lot more precious about tiptoeing around emotions and making sure that people were feeling okay and taking care of their feelings. I just don't care as much anymore. I care about your long-term growth as the person I'm talking to. I care about you and me having an honest, deep, authentic rapport. The tone of that is set now more by me; 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. This is not the place for you. At the end of the day, preciousness is great, but it's not everything. Everything else holds true, though.

Jackson: Pretty good hit rate.

Molly: Thanks.

Jackson: 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?

Molly: Partly. But what is your version of that? There is a version that is "How do I show up and serve this person?" 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. What is your version that plays to—

Jackson: Your actual skillset with your authentic service.

Molly: Authentic service, exactly. The idea of "How do I show up and serve them?" carries an insinuation that it's my job to give them a lot of intros and do a lot of things for them. That's not how I help. My help is much more personal, relational, and deep. I think that rings true.

1:29:28: Friends, Seeing in the Third Person, Femininity in a Masculine World, Love

Jackson: I want to talk a little about friends and friendships. I'll share two quotes. "I'm in an industry where the term friend has no meaning at all. It took me a long time to learn the difference between a few good chats with someone excitable—often unearned intimacy—and true friendship, which requires effort and is not without friction." "I've consistently shied away from testing the depths of my relationships for fear of judgment or rejection. 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?

Molly: Forcing myself off the ledge. The hesitance is a fear of rejection, fear of humiliation, or something of that sort.

Jackson: Is your willingness to ask proportional to the connection?

Molly: I think it is. It was always an insecurity about whether my perception of the depth we have is the same as yours. Asking for something large is a test of that. Was I right in my calibration of how close we are? I wasn't sure about that for a while because I was so scared of asking. I would always run away instead of testing the depth of the relationships.

Jackson: Again, this is where you're underrating all of them. By your actions, you won't ask anyone for anything.

Molly: I've also now realized that you're denying them the satisfaction of being able to fulfill your request and do something for you. They would actually find that deeply meaningful. Why are you not asking them and giving them that opportunity? It's almost the same framing I like for selling: if you're so scared of asking someone, why are you not reframing it in terms of the fact that they might be offended if you didn't ask them? It's a good opportunity, and you should be bringing it to them.

Jackson: It's generous.

Molly: It's generous, exactly. These mind tricks go far.

Jackson: You just gotta judo yourself.

Molly: Judo yourself into doing the things you know you need to do.

Jackson: A theme that comes up multiple times in different concepts for you is that inspiration comes after acting, as does forgiveness. All these feelings come after the act of doing the thing.

Molly: Absolutely.

Jackson: I’ve thought a lot about intimacy, intention, 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." "Intimacy runoff is what I call it when a person craves closeness and feeling seen, but isn't looking for it in the right places. 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? How do you get better at defaulting to maintenance versus falling for the illusion that we don't need proximity and just need one really deep conversation ever so often?

Molly: The main thing that's helped with this is becoming less avoidant. Running away from the friendships you already have usually comes from a place of shame or guilt. You think, "I haven't followed up to schedule with them for a month. I should just talk to somebody else because they obviously don't want to see me either." You're just inventing something to avoid and grasping for something else. Just asking for more things, being more annoying, and being more yourself helps. Over the last year, I’ve been much more comfortable showing myself to my friends in this way. It has shown me that they will rise up to support me in really beautiful ways. The depth of friendship was limited by me. I remind myself of that often now. I ask myself if I am acting from a place of avoidance in the context of friendships and relationships.

Jackson: Painfully true. Another essay of yours I loved is called "Women See in the Third Person." You quote John Berger to start: "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 herself walking or weeping. Her own sense of being in herself is supplanted by a sense of being appreciated as herself by another." Then you write: "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. 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." "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." To what extent have you gotten better at living in the first person, and to what extent have you embraced living in the third person?

Molly: It's very helpful in the context of being good at brand and marketing. Living in the third person allows you to think about how other people are going to perceive all the things you do and how you present yourself. It's great for storytelling because you're basically one of those startups that's able to create virtual humans, but you're doing it in your mind. You’re thinking about what each person would think. I was always pretty good at that, and it was useful in the context of the mediums I worked in. However, it was massively limiting as soon as I got into investing. It was very clear that I was thinking so much about what other people were thinking. It was consensus-driven and led me in directions where I was constantly pushed and pulled between wanting to be myself and caring about what my LPs, other investors, or founders thought. There was a distinct turning point when I realized I actually don't care about any of that. It was just something I could grasp onto to feel like I was in control in a job where there aren't many things that feel that way. Dividing the two helped. I live much more in the first person now than I ever have. It mainly comes from the confidence of taking leaps and making big decisions. I can say, "I made that, and it was for me, not for anybody else." Those decisions compound. They grant a sense of confidence in knowing who you are by pointing at decisions and saying, "I did that."

Jackson: It's certainly not the exact same, but it might be somewhat related. How do you lean in to and out of femininity in the professional part of your life, which is a very male world, both literally and energetically?

Molly: I've gone back and forth on this a lot. In the beginning, I was much more attached to preserving the way that I treated people and the nurturingness. I have become more truth-seeking over time and just more direct, less precious. 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 the main example. It's probably the one area where I actually do have to be something that is not what I would call myself. It's a part of me, and I've made my peace with that, but it's definitely much more male.

Jackson: Putting on a role to be legible.

Molly: Exactly. It's worth it because I'm getting something out of it.

Jackson: It's totally instrumental.

Molly: It's totally worth it. It's completely instrumental. I'm using them, but I have to remind myself of that because otherwise I feel like I'm selling out. That's the worst possible feeling for someone like me. As an Enneagram 4, we really don't like selling out.

Jackson: This is quite related. I want to talk briefly about love. You wrote, "Tom 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, particularly in that regard, and allowed you to see more in the first person?

Molly: It made me a lot safer and able to embrace myself. It was from showing him all of me and having him accept it with open arms. Growing together and seeing that I'm able to help him in ways that have revealed to me what my strengths are has been special. He's able to help me in unique ways that show me what he's good at. That kind of symbiosis and relationship has been really special and made me much more confident in myself.

Jackson: Relates to the uncertainty point earlier.

Molly: Exactly.

Jackson: There's this really stable thing that allows the other stuff to be.

Molly: Exactly. Deeply getting to know a person and seeing how I am different and the same as him is powerful. In Enneagram types, we are the opposite. He's a seven, and I'm a four, which is great because we have very clear lanes of what each person is good at. It's really informative to see another person live in a completely different way that fits in well. We have the same values, but it's constantly reminding me of my choices and why they're important to me. There is something about that contrast that is really powerful.

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

Molly: I stole that from a tweet.

Jackson: Beautiful.

Molly: Good.

Jackson: How do you get closer to that total abundance when it comes to love?

Molly: Letting yourself feel it makes you realize it's multiplicative. Surrounding yourself with it in a way that I definitely felt might have been selfish years ago is actually a wonderful way to live. I’ve realized it’s about reprogramming yourself to expect that, but not to act as if you deserve it.

Jackson: I jotted down a note of you quoting Tim Keller, which might be a clue here: "The feeling of love follows the action of love."

Molly: It does. Isn't it?

1:42:07: Grab Bag: Art, Catholicism, Gratitude, Beauty

Jackson: I have a few miscellaneous things before we wrap up. You referenced a book called The Decisive Moment by Henri Cartier-Bresson, and you said it is about how everything is about timing. What does that mean?

Molly: I love that book. It has a beautiful cover, and it's all about his approach to watching the world and waiting for the exact moment to capture the shot. Photography is usually taught as framing, lighting, and composition, but the decisive moment—the actual timing—is one of the hardest to nail. He's a master at it. You look at every shot, and it's caught midair, with an ecstatic expression.

Jackson: Photography might be a medium of timing in many ways.

Molly: Exactly. It's a patience and a presence that enables him to get that shot. I am always reminded that if I think I'm living in first person now, he must live in first person times a million.

Jackson: It's like zeroth person.

Molly: Exactly. He's just pure presence, which is so special.

Jackson: You often reference him, so I figured I’d ask: what do you love about C.S. Lewis?

Molly: He taught me a lot about love and Christianity. Him being so open with his journey and his path is something that I found deeply valuable. His level of honesty with the world has inspired me to do the same.

Jackson: What do you love about the film Magnolia?

Molly: It's so weird.

Jackson: Paul Thomas Anderson.

Molly: He's one of my favorite directors. I watched it when I was very small, and it 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 a bunch of different storylines that then conjoin into one very strange moment. I felt deeply moved by it. This is someone's really weird mind that they just inflicted on me. They're not even trying to tell a story that makes sense or has a message. I loved that. To me, it was the epitome of doing something at the peak of your craft, with excellent actors and beautiful cinematography, that kind of makes no sense.

Jackson: After Boogie Nights, you're supposed to be ready to rock. But he got weird.

Molly: It was the embodiment to me of the saying in the film industry: "Make one for money and then make one for art." This is very clearly his "one for art," and I loved it.

Jackson: You had another quote about films from Patrick Kavanaugh: "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?" This got me thinking about modernity. Art and media are the objects. They must be the source of interestingness, and they must be experienced rather than a backdrop for my experience. I'm curious about your relationship to this. For people who want to deeply study the things we care about, the temptation is that everything has to be Magnolia. To what extent is that resonant? Reading through your writing, my "read it later" list has 20,000 things on it. You are an amazing curator. As someone who consumes so much great art, do you have an interest in basic content that isn't intellectual?

Molly: I love normiecore stuff. That quote gets at it: I love weird arthouse films, but I also love trashy superhero TV shows. The most popular TV shows are mostly popular for a reason. I've learned not to overthink many areas of my life. Media, films, and blog posts are areas where I like to have a balanced diet: a bit of the avant-garde and a whole bunch of what everyone else is talking about. It's probably pretty good.

Jackson: High and low together.

Molly: You also see that sometimes they're talking about the same thing in different terms.

Jackson: 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 a la carte." Do you think this is a blessing in reality?

Molly: I wrote that many years ago and have since converted to Catholicism, which is an interesting counter-example. It's much harder, actually. My upbringing couldn't have been as free and open 50 years ago. Growing up in a small town with two hippie parents, I could live however I chose. That felt like a great weight, but it also inspired me to be interested in all the different options. That was special, and I hope to give parts of that to my children. On the whole, it was hard to figure out what morals are and what it means to be a good person. It is a burden to bear. [Related: Henrik Karlsson on being sentenced to freedom (33:10) - Dialectic]

Jackson: This leads into my next prompt, which 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?

Molly: It's much more externally focused. It gave me a lens of seeing how to connect with and help other people.

Jackson: It fills that hole.

Molly: It gave me a sense of belonging that comes from being part of a global community and a belief system with clear morals around living a good life. I agreed with those from the beginning. It has made me much more confident in my beliefs of how I want to live and who I want to be.

Jackson: You've used the framing that life is a series of projects. Are there any Molly projects bubbling up? Any creative side projects, or is it all Moth Fund?

Molly: I've been into making jewelry recently, learning how to set stones. I'm starting a project making pieces for friends and naming the pieces after them. It’s fun to collaborate with someone you love and make them something. I've also been making cyanotype prints. It is a type of photographic exposure paper where you place objects and expose them to light to create a beautiful cobalt color.

Jackson: It is very similar to dialectic blue.

Molly: They are gorgeous. I love making them as prints to give as gifts. I always have to have a craft to play with; otherwise, I feel like I'm floating into the abyss. Just helping people is not enough. I need to occupy my hands.

Jackson: Intangibility. Can you make the case for calling people over texting?

Molly: You hear so much more context about their life than they share over text. You hear weird noises, or they drop their phone and apologize. There is something beautiful about that.

Jackson: Higher resolution.

Molly: I say this as a member of Gen Z who hated calling my entire life.

Jackson: Avoidance again.

Molly: It is totally avoidance. Then you start doing it and realize they were always right. I should have called.

Jackson: As a self-proclaimed 10,000-hour expert, what do most of us need to know about apples?

Molly: Pink Ladies are the best. Envies are the second best. Pink Ladies are the most dependable anywhere you go in the world. They are a trademarked type, and they will be very good. Envies are more variable. There is a whole bunch of other types that I am still trying to find, but those are the two that will always be good. Always avoid Gala apples. I don't believe in the yellow ones. The really small ones are really tasty and taste kind of like berries. I think apples are a perfect food.

Jackson: For any reason other than narcissism and the coincidence of you, your name, your life, and the person you married, is there anything special or symbolic about the letter M?

Molly: I think it's a very cool letter. It can be turned upside down as a W, and it becomes a zigzag if you put them all next to each other, which is very cool. You can use it as "mmm" to mean affirmative or thinking.

Jackson: I like that.

Molly: I have always liked making worlds around myself and the things that I make.

Jackson: It is pretty amazing. You married a person with an M. It feels pretty deterministic. If you haven't looked at Molly's blog or her name or her initials, there are a lot of M's.

Molly: A lot. I really like alliteration.

Jackson: 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 the perfect freedom of single necessity." Maybe I have this wrong, but there is a contrast between stalking your calling and yielding. How do you relate to that?

Molly: I think that is one of the best articulations of vocation that I have ever found.

Jackson: Stunning.

Molly: Stalking is having ideas and letting your ideas guide you to places. It is probably more intellectual.

Jackson: Like sniffing.

Molly: Exactly. Yielding is more like actually just accepting what is true from your heart and dropping the shoulds. It is realizing this is probably the thing that I have always been good at my entire life. Maybe I reject it, and now it is back. I wonder, "Is this really the thing? I wish it were something cooler." But you're just a weasel. The yielding is often the most powerful. The stalking is useful to get out of your system because you have these ideas of wanting to be a director or a designer. Yielding was more about realizing that I really like the peopling. I like getting better at understanding people and serving them. That has always been true. I also really like making things, and they can be roughly divided. The peopling is more gratifying for me at this point in my life. I had to accept that. I wondered if there was something cooler.

Jackson: It is a looking, and there is still an openness. The front end of that is important. You have to be aware, looking, and open. A lot of people have the disposition of being open, but they are looking at the thing in the field of view and thinking it isn't exactly that.

Molly: They are seeing it come again and again and again. They think it couldn't possibly be that.

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

Molly: I enjoy feeling things deeply, and I always have. It is one of the characteristics of being a Four. Suffering feels meaningful to me in a way that I don't try to escape. I have been more skeptical of joy until recently. Finding that balance is something that I am still striving to do because suffering has historically felt more real to me than joy. Now I am getting to a point where the joy is around more often, so I have to accept that it is real. When the suffering does come, it is real too. I am not trying to get to a place where I don't see it as coming and feeling relieved that it is back. That is a funny tension some people might share. Others might be more used to the joy. How do you get more comfortable with the other one and believe it to be real, too? I am constantly questioning which one is the truth.

Jackson: Hence, how I frame the question.

Jackson: I have one more thing. We talked about lowering the pressure and the preciousness earlier. I have two quotes, including one from you: "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." You were writing that in the context of preciousness being worth protecting. Then there is a quote from Goethe: "Encourage the beautiful, for the useful encourages itself." Why is beauty virtuous as an end?

Molly: Because it makes us all feel. That in itself is worth a lot. Beauty has been a core theme in all of the things that I have done. I've just always been very drawn to it. I think it is true of many other people, too, if they just let themselves feel it more. I don't think I'm the only one.

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

Molly: Thank you. It's a pleasure.

1:58:58 Thanks Again to Notion

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