51. Nan Ransohoff - Power Laws for Philanthropy

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Nan Ransohoff - Power Laws for Philanthropy
![51-Nan_Ransohoff.jpg](/art/51-Nan_Ransohoff.jpg) # Description

Nan Ransohoff (X, Substack, Website) is Head of Public Goods and former Head of Climate at Stripe. This includes Frontier (which she co-founded): an advance market commitment that accelerates carbon removal by guaranteeing demand for it before it exists. They also recently launched Intercept Fund, a new effort to end respiratory infections, led by Nan and Charlie Petty.

Nan has written extensively about Stripe’s efforts and philanthropy broadly, including her call for general managers for the world’s pressing problems, and on what she calls the third wave of American philanthropy.

We talk about what a "Nan" is and why we need GM’s: ambitious founder-like people who obsess over an outcome and work backwards from it, wearing whatever hat the problem requires. We discuss taste in big problems, slicing them up and making them tractable, and why vision is in short supply. We also discuss the coming wave of new philanthropic dollars (est. ~$40B/year), primarily driven by The OpenAI Foundation, Anthropic Founders, and Anthropic employee matching, and how the ecosystem will need to mature to effectively deploy this much capital. Nan also reflects on her unlikely turn toward philanthropy and what it felt like to get off the ladder of a specific kind of ambition. We wrap up with a range of miscellanea and some fun debates. I hope you are inspired to notice problems you can’t ignore, be optimistic and specific about the world you hope for, and choose an (unlikely) path that you are proud of.

Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. Watch here for more on Notion's new developer platform and workers. You can learn more at notion.com/dialectic.

Timestamps

  • (0:00) Opening Highlights
  • (1:15) Intro to Nan
  • (3:18) Thanks to Notion
  • (4:53) Start: What is a Nan? Nerd-Sniped by Orphaned Problems
  • (12:39) GMs, Seeing the Chessboard, and Working Backwards from Outcomes
  • (18:55) Good Taste in Problems, Vision, and Good Finish Lines
  • (35:43) Advance Market Commitments Tactically Solving Carbon Removal
  • (41:35) Focus and Sketching Out or Slicing Up Messy Problems
  • (49:39) Legibility, Public Rallying, and Ambition in Philanthropy
  • (54:38) Third Wave Philanthropy and Hard to Quantify Problems
  • (1:06:50) Risk Tolerance in Philanthropy and Scarcity of Funders and Allocators
  • (1:15:22) The $40B Tidal Wave of New AI-Money and Why Start Now
  • (1:19:53) Amount of Capital, Government Philanthropy, and Making Philanthropic Founders Rich
  • (1:31:44) Nan's Mid-Career Inflection Point and Getting Off the Obvious Path
  • (1:39:47) Grab-bag: Why Stripe Funds Public Goods, Making Things with Friends, Creative Partnership, Iceland Drone, and Scone Heads
  • (1:49:39) Syllabi for the Squishy Topics & Study vs. Experience
  • (1:57:01) Inputs & Outputs and GLPs for Attention
  • (2:04:38) Closing: Interviewing Parents and Imagining an Obituary
  • (2:09:58) Thanks Again to Notion

Links & References

Transcript

(4:53) Start: What is a Nan? Nerd-Sniped by Orphaned Problems

Jackson: (4:54) Nan Ransohoff, thank you for joining me. This is so fun.

Nan: (4:56) Thanks for having me.

Jackson: (4:57) We're here at Stripe. My first time. There were some interns walking through and they were like, "This is where they make the videos." And we're doing it.

Nan: (5:00) We're here.

Jackson: (5:06) I want to start with a question that you might find slightly annoying, but I'm going to ask it anyway. When I first met you, we had a conversation about some of what you do. Less so the Frontier stuff and more the stuff you've been writing about a little bit lately—GMs and new philanthropy and so on. And one of the things I wrote down was we need to figure out how to have more Nans in the world. And in some sense, I think part of what you've been writing about, or at least thinking about, is a little bit of like GMing the GMs—how do we have more of these people? And so if you'll indulge the kind of silly frame: What is a Nan? What is it that you've found yourself doing? And why do you think this sort of shape is fairly unusual?

Nan: (5:53) What is it that I do? I think what I get excited about is sort of thinking about... I kind of get nerd-sniped by problems that are important for the world. I go down a rabbit hole because I'm just interested in the thing. When I get down the rabbit hole and I'm like, "Okay, who's working on this? Who feels that it's their job to see this problem through?" and I don't find anyone, I kind of panic. And that just seems to be a pattern for me. That is exactly what happened with carbon removal. I read the 2018 IPCC report in 2019 and was learning about—sort of relearning—the climate math and saw we need a lot of carbon removal. It took me like three weeks to talk to everyone in the field, which freaked me out, and I was like, "Okay, I'm going to quit my job and work on this." And that's again happened with this new thing on respiratory infections, which we can talk about. But I think I basically find a problem that seems important to the world and I can't get it out of my head. In basically all of the cases, I am not the best person to work on it. I was not an expert in carbon removal. I'm not an expert in respiratory infections. But it's kind of like you go to war with the army you have, and if no one else is going to take responsibility for it, I just find myself like, "I want to work on this." That's not to say there aren't lots of other people who also can take responsibility for it. But I think it's just this almost feeling of shock or outrage or awe that these big problems are going unmanned, and wishing I could work on all of them, but not being able to, so picking a couple of them. So maybe that is one way to think about what it is I'm trying to work on or my lens in. Then you realize, "Okay, well, geez, there are so many different problems to work on." I wish I could have a thousand lives and do all of them myself, and that obviously is not currently possible. So how can we get more people thinking about finding a really big problem and taking ownership over it? And not just working on the problem, but really obsessing about the outcome. How do I deliver the outcome for the world? That can exist at a lot of different altitudes. It can exist at really big ones and more micro ones, and all of those are fair game. Finding the right problem and defining it at the right altitude is the whole thing. When you say GMing the GMs, I think a thing that gets me really excited is how do we identify these big problems that should have people working on them, find awesome people, and match the problem and people together—and do that at increasingly larger and larger scales.

Jackson: (8:16) There's an element of this that's like, "Surely the adults in the room are working on this." Yeah, most people sort of bounce off these intractable problems. Most people, when they learn about whatever—you have some math somewhere, it's like a trillion dollars a year of spend to remove a teraton of carbon—most people don't go spend three weeks talking to everyone in the field. Maybe you're just super high-agency, and you clearly are super ambitious. Perhaps the problem is that most very ambitious people work on other types of problems. But do you have any sense of whether that was always the case for you? When you've seen it in other people, what trait-wise causes you to be attracted to these types of problems that normally go—you talk about it like they're orphaned or they're invisible, or they're just so large that there's not even a finish line in sight, so it seems really hard.

Nan: (9:19) I don't know. I feel like I've become progressively more that way over time, and I'm trying to think about why that might be the case. I think maybe some of it is just natural career progression. You start working on a project, and then you're working on a product, and you're trying to build a company. Now we're trying to build an ecosystem, and now we're trying to build an ecosystem on top of an ecosystem. In my head, that is a little bit how it ladders up. I don't think I've always been thinking at the scale that I am, and I hope that I'm thinking at a bigger scale and the future version of myself is thinking at a bigger scale. Maybe another piece is that I don't feel that I let myself follow my own interests and curiosities for a really long time, and I've increasingly let myself do that. That has led me in more interesting directions that feel more authentic to who I am and what I want to be thinking about and what lights me up. But that was a muscle that I had to build over time. I don't feel that for the first 25 to 30 years of my life I did a very good job building that. And now I've given that a little bit more space. It's a bit of a woo answer, but I think that is part of it.

Jackson: (10:39) You've always been ambitious. Was there an element of this where these problems were lower status? That doesn't seem quite right.

Nan: (10:49) I think it was maybe more historically chasing the things that one is supposed to do and was probably more a little bit more box-checky. I did the whole PM thing. I did consulting after undergrad and then I did the PM thing. Those are great, but I think I just got a little bit bored with that.

Jackson: (11:11) Which came first, by the way?

Nan: (11:12) Consulting.

Jackson: (11:12) Sorry, I mean getting bored and then finding the climate thing, or finding the climate thing and realizing you were bored with the other stuff?

Nan: (11:18) I did consulting for a few years after undergrad. It was interesting on a skill level, but then boring on a "why am I working till two in the morning on a random..."

Jackson: (11:30) But maybe Uber—you then went to Uber, which is less "boring," for sure.

Nan: (11:39) I guess I felt I got more confidence to diverge from a more traditional path. Genuinely, when people ask what I do now, I sometimes struggle to describe it. It is a little confusing even to me. The fact that I work in a version of philanthropy is not in line with where I ever expected I would be. I feel that I was actually a little dismissive of it historically—and am still in some capacity. It doesn't quite match my mental model of myself, but I think it's where important problems and interesting work are. If you can come up with creative mechanisms to do that work, then it's a really fertile space. There's something about just getting more comfortable with off-the-beaten-track stuff that has maybe come with age and other facts of life. It has let me pay more attention to what I'm actually interested in solving rather than what I should be working on.

(12:39) GMs, Seeing the Chessboard, and Working Backwards from Outcomes

Jackson: (12:38) There's an element of this that I think—and you have an amazing post on this GM idea—is part problem selection, but it's also part seeing the chessboard. Unlike a lot of tech startups, where the Y Combinator model is very much "find one loose thread and just pull that thread" without worrying too much about the chessboard, it doesn't seem that carbon removal is that type of problem. It is very much about seeing holes, understanding coordination problems, understanding market forces, and figuring out how to induce demand where there isn't demand. Is that skill set something that you developed aspects of in other jobs? Is it something you had to learn on the fly, or is it something that's intuitive? I'm curious about other types of people who would be good at this type of problem—where might they be coming from?

Nan: (13:37) I think the difference between a YC type of approach and a GM type of approach is that in a GM approach, you are obsessed with the outcome you want to deliver and you're working backwards from that outcome. Whereas oftentimes in startups, you're starting somewhere and pivoting your way to the outcome, but you're maybe less specific, or you care less exactly where you end up. It's more emergent, exactly. For GM type of outcomes, you're thinking, "This is the outcome that I want, and the thing that's going to have to flex is everything else." I actually think the traits that you need for both of those things are quite similar. When you're starting a company, you often have to play a lot of different roles and wear a lot of different hats. You're a policy person one day, an engineer another day, and a designer the next. In the case of a GM, it's very similar. You're pulling whatever lever you need to pull and you're obsessed with a thing, however you define that thing. In both worlds, you're having to respond dynamically to the environment and the world around you. You have to adapt quickly, you have to be really nimble, and you have to reason through things on the fly when you get new information. Those are traits that I think are quite similar in both cases. Which is all to say, I think there is a huge potential for the shapes of people that would otherwise be founders to make for really good GMs. That is a bit of a paradigm shift in how we think about people working in philanthropy and also ambition, broadly.

Jackson: (15:32) You started to allude to this when you were talking about the feeling you had toward philanthropy, which is basically that serious people work on companies.

Nan: (15:35) Totally, totally.

Jackson: (15:44) Which obviously isn't true in every part of the world, but it's probably broadly true in San Francisco, and especially in the high-tech startup ambition part of the world. There's an element of being able to take the force of ambition and all the other things associated with it—the opportunity, the status, the challenge, and maybe the opportunity to get rich—and applying them to things that often aren't connected to those rewards.

Nan: (16:10) Yes. Okay, two things. One, even now, I still bristle a little bit at the word "philanthropy" because I think the thing that we want to deliver is good outcomes for the world. We want to think about public goods—or they don't even have to be public goods, but things that benefit the public.

Jackson: (16:26) What are public goods?

Nan: (16:39) What would an economist say? I think that's part of it, but it doesn't have to benefit every single person. A canonical public good would be carbon removal, which does benefit everybody because we all share the air. Yeah, it's a big one. But I think that we should choose the most capital-efficient mechanism to solve the problem. So if you can deliver a great outcome for the world and make money from it and build a business around it, great—do that. We should only move into pure philanthropy if you can't figure that out. I think capitalism is great, and if we can build great companies to solve world problems, we should do that first. So philanthropy is a subset of building good things to improve the world. I think that's an important point because there are a lot of different kinds of companies in between pure philanthropy and maximizing profit. Those should all be on the table and considered—just move down the stack as needed, but start by trying to make money.

Jackson: (17:47) Yes. The tech world tends to barbell, which is either the most ambitious possible version of a company or a pure nonprofit philanthropy thing that's basically charity.

Nan: (17:56) Totally. And I think there's a really interesting space in the middle, but that needs creative funders and people who are going to consider allocating capital in this squishy middle. Anastasia Gamick has written a bunch about this—these companies that should exist but don't because the risk-reward doesn't fit into venture, private equity, or philanthropy, so they go unworked on. I think that's an important space to hunt.

Jackson: (18:23) Sort of like a philanthropic lifestyle business.

Nan: (18:28) Yeah, totally. Yeah, exactly. It's not venture-scale returns, but it's also not a grant.

Jackson: (18:32) The big idea here, I think for both the GM thing and the broader point, is all of these things. Whether it's a business or nonprofit, the approach, whatever it might be, is downstream of what is the best way to attack this problem. And the GM orientation is less about, "I'm going to start a company." If a founder is oriented around a company, the GM is oriented around the problem.

(18:55) Good Taste in Problems, Vision, and Good Finish Lines

Nan: (18:52) Yes. That's a really pithy and good way to describe it.

Jackson: (18:56) What makes for good taste in problems? One of the things you write about is an interesting spectrum of problems that tend to go unsolved. It ranges from things that we don't really see because they're kind of illegible, to climate, which is just impossibly big, to things that surely other people must be working on. You even have a point where you say some are perhaps better described as things we want to be true rather than problems.

Nan: (19:25) Right, right. Yeah, okay. Well, I think that I have some experiences, but not a ton of experience in this—I would like more. But I think like a good forcing function or a good prompt for people to think about is: in what way would I like the world to be different? What do I look at in the world and say to myself, "That is crazy that we're still dealing with that"? Or, "I cannot believe that the world is a certain way." That sort of shock and awe is a good place to start. And you can kind of feel it in yourself. I think part of important problem selection is: does it light me up? Does it get me fired up?

Jackson: (19:28) Yeah.

Nan: (20:06) And that's maybe an initial good filter, which requires, by the way, to even get to that point, dialing up our Larry David sort of annoyance with things.

Jackson: (20:19) Yeah. You have to see the water. To go back to climate, my presumption would be that you had some care or thought or interest in the climate stuff, and then there was some ignition point—either in reading that 2018 data or something else—that caused it to be a hair-on-fire problem. Whereas for me, I intellectually know the climate stuff matters, but nothing's burned.

Nan: (20:39) It doesn't do anything for you? Well, what are examples of problems that elicit that reaction for you?

Jackson: (20:44) Well, I think part of the interesting thing about this is that we grow to not see the water on some of these types of things. I think maybe this is too meta, but I probably tend to orient towards most of my interests through people. If I met someone who is fired up—I wasn't that interested in philanthropy, frankly, until I met you. There was an articulation of it that was partly your energy, partly your articulation, and partly that it's framed around GMs, which are the people who are going to solve these problems. It was a receptacle for me. So maybe there's two ways to ask the problem taste question. One is just: what are the types of problems that are really important? And maybe there's a separate thing which is: yeah, the problem matters, but also choose a problem that fits you.

Nan: (21:38) Yes. Right. There are different ways into the problem piece. Maybe to finish laying out some good proxies for this—the thing that gets you upset or riles you up is a good lens. The tractability piece is a really tough one to assess because there are lots of problems that are really important and make people frustrated, but figuring out the right altitude to define the problem and come up with solutions to move the ball forward is really tough. In that category, that's where either one is already an expert and can see the levers to pull, or you become an expert, or you talk to experts and try to ramp yourself up to see if there's a there-there. And then I think another bucket here is the neglected piece. Is there anybody else working on it? If there's already someone great working on it, get them to do it.

Jackson: (22:45) Or go help them or whatever.

Nan: (22:46) Yeah, go help them. Exactly. It's sort of like oneself is the last resort. So it's some combination of: is the problem big and important? Does it light you up? Is it tractable? And the neglectedness piece of it. But I kind of sneaky think that most people don't even get to the second two. I think we can all pay more attention to defining, in a more normative way, our vision for the world and what we want to see the world look like. We are very quick to be able to critique the world, and it is harder to establish a vision or to ask a question like: what is the way that you want the world to be? What do you want to be true?

Jackson: (23:41) Yes. I've talked about this with a few friends. There are a lot of people with very specific negative orientations of the world—specific and pessimistic. And there are a lot of people who are vague and optimistic. But the part of that matrix that's rare is optimistic and specific.

Nan: (23:54) Totally. I think that's a really important point. And I think that specificity is what makes it believable that something can be solved.

Jackson: (24:05) Yes. And it certainly makes it much easier for someone to join you, which is one of the things that the startup world has gotten really good at: how do we engineer the gravity and interest? Speaking of vision, you have a great older post on which moral virtue is in short supply, and you're talking about vision. You spoke about it briefly, but what makes for really compelling visions? Or if that's not the right question, who's good at this?

Nan: (24:34) I think we can all be better at it. That is my honest take.

Jackson: (24:38) How does one get better at this?

Nan: (24:38) How does one get better at it? I think that vision can exist at—it sounds like this big, bold thing, and it is—but it can exist at the level of the world, a family, or a self. It's imagining what oneself looks like in 10 years. Imagining what one wants their relationship with another person to look like in 10 years. Imagining what one wants carbon removal to look like in 10 years, or the city of San Francisco. There are a lot of ways to scope that, but you can practice at the level that you feel most comfortable with. I was thinking about this in the context of our lunch table on the climate team a couple months ago. We were asking ourselves: if you had a billion dollars to spend unrestricted on good things for the world, what would you do? That kind of prompt reveals a lot of not knowing in all of us. How would I spend that? What are the things that I care about and how would I allocate capital towards those things? Or practicing it on the level of the city that you live in. You think, "I love this city. What would I want it to look like in 10 years? What does good look like to me?" Those prompts for me are really expansive. They force a lot of questions around both the values that would drive the end vision and then also, tactically and specifically, what are the levers that you can pull and things you can do together? Does that resonate at all?

Jackson: (26:29) You had some prompt somewhere where it was like, what would you do if you were mayor of San Francisco?

Nan: (26:32) Yeah.

Jackson: (26:36) You also said somewhere else that most politicians actually don't have a vision. We don't really exercise this muscle.

Nan: (26:42) Yeah. Well, why is that? I'm kind of surprised that why aren't we as citizens demanding this? Not to say nobody has vision, but if somebody asked me to clearly articulate the vision for the last several presidents about where they wanted America to be at the end of their term, I couldn't do it. And this is not the area that I am most educated in, so maybe other people could do it. But don't we think that the average citizen should be able to repeat that back? Why is vision in short supply? I don't really know.

Jackson: (27:20) Of course. It reminds me of a conversation I had with a friend that I talked about on an earlier podcast this year. She had asked me, "What do you really want?" and I couldn't answer.

Nan: (27:34) Define that question.

Jackson: (27:34) Well, one of the mental images that we had in one of the conversations was that it's sort of like when a kid really wants ice cream.

Nan: (27:37) Yeah.

Jackson: (27:43) You can feel it in your body. You're bouncing, you're bounding down the street. I almost wonder if part of this is that in adulthood, society definitely trains you to critique, and it doesn't really train you to be like, "That thing is over there and I'm going to go get it."

Nan: (27:46) Yes.

Jackson: (27:58) Which is a sort of silly version of the agency thing. I almost wonder if there's some aspect of that here. To your point, being able to even say it—maybe it takes some silly prompt like, "Here's a billion dollars." It's funny, this makes me think. There's the classic question: "What would you do if you had a billion dollars?" I think it's Jeremy Giffon or David Senra who has this inversion of that: "What would you not stop doing for a billion dollars?" If I offered you a billion dollars to stop doing everything you do, what would you not stop doing? It's easier for people to answer that. I wonder, were you someone, either growing up or now, who does annual planning, or sets annual goals, or any of these types of things?

Nan: (28:44) I do a version of that now, but it's not like an OKR thing. It's squishier than that. I do try to force myself to think about what I want to be true by the end of the year for myself. Last year, I had a section on a few projects and specific things I wanted to do, and then some of them were kind of vibes or character development things. But I do think that just articulating that is helpful. That is some version of manifesting—being able to. Athletes do this all the time. They're picturing themselves in the winning state. Michael Phelps is picturing all the things that could go wrong—his goggles get water in them, he's still swimming; his suit rips, he's still swimming. He's going through all these scenarios so that he's never surprised. There's something to the visualizing of a future scenario that makes it more likely to happen.

Jackson: (29:57) Michael Phelps has the advantage, though. In your work life, you have very specific aspects that are complex, but there are aspects that can be a finish line. That's what Michael Phelps has. Whereas emotional goals for your life or your relationships are hazier. You mentioned Anastasia. One of the points she makes in at least one of the posts I read of hers is the importance of a finish line. It feels like that is also very critical to the GMing thing broadly. It's the outcome. I want to win. Last year I had two goals: one was to do 21 episodes of this podcast before I could quit, and the other was to run the New York Marathon.

Nan: (30:51) Those are very clear.

Jackson: (30:53) Clear finish lines were way better for me than "I want to run more" or any of these hazier things. When it comes to carbon removal, of all the things that can have an impossibly large finish line, that's among the biggest. Presumably, you have some big finish line in the future which is the teraton of carbon removed. Are you then breaking off little other finish lines? And if so, how does that work? What makes a good finish line?

Nan: (31:38) For Frontier, which we started in 2022, we have this end goal. In 150 years, we need to do a trillion tons of carbon removal, roughly. Then you say, "Okay, well, how much money is going to be needed to do that?" You kind of work backwards. I don't think one needs the specifics of the whole plan, but very tactically, we have the end goal, and then we have a vision for where we wanted the field to be in 2030. We wrote a set of statements of what do we want to be true.

Jackson: (32:10) That was almost the real finish line. A hundred years is...

Nan: (32:15) Yeah, maybe we'll be alive. But what do we want to be true in 2030? That was the vision. Then we have a strategy, which is our best guess at any given point in time of how we think we are going to get there or what we're going to do versus letting other people in the field do things. That breaks down into an annual plan. We do annual OKR planning, and when the world changes, we change the plan. That translates into what we call ships, and then that translates into a weekly plan. It's very concrete and tactical, reasoning backwards from the outcome. Then the world changes, it gives you new information, and your plan changes. That's okay; that should change. But if you don't have a plan, it's pretty unlikely you're going to do it.

Jackson: (32:58) How did you—very broad strokes—how did you arrive from joining Stripe in 2020 to that 2022 vision and plan? Because presumably, there's a mix of what is actually the right finish line and goal, and what is the right way to get there. We haven't even talked about advance market commitments and all the structural things. To go back to the original point: everything is downstream of problem-solving. I think part of the reason this is so hard is we have a lot of templates of what this looks like in company building, and this feels like something else. I mean, it's amazing you did it and you've published a lot of this so people can go back and look, but compressing that timeline, you could see how someone would bounce off it.

Nan: (33:47) I don't think it’s that different from the company planning piece. I think maybe it's different for a mature company or a growth-stage startup, but most well-run companies have a vision of where they want to be in X years. The OKR planning process, or whatever process one decides to use, is a way to take that end goal and work backwards from it.

Jackson: (34:23) Maybe this is where I'm getting hung up. In this case—and granted you were doing it from a very strong foundation, which was Stripe—so in that way, it wasn't like a startup. But in other ways, it's actually a lot more like going 0 to 1. You have to do both. The best comparison would be like Elon's Tesla master plan or the SpaceX master plan, where you have to go 0 to 1 a whole bunch of different times and do all the OKR-level strategic planning that a mature company would do. That's why it feels so big.

Nan: (34:55) That's fair. I think that's fair.

Jackson: (34:57) And you're just like, "Well, be more ambitious."

Nan: (35:04) Well, I just think that it’s not rocket science. I just don't think it is.

Jackson: (35:08) How hard was it to become an expert in this if you presumably talked to all the experts in three weeks? Because that's another part of this: "Oh, I'm learning about climate in 2018; it would take me five years to even get up to speed."

Nan: (35:21) You don't have to learn the whole thing. You're scoping the thing that you are learning. For me, a very motivating thing—and to be clear, there were other people working in the field, this was not just me by any stretch—but a really motivating thing is: who else is going to do it? This slice of it, yeah.

(35:43) Advance Market Commitments Tactically Solving Carbon Removal

Jackson: (35:43) How early was the—and maybe this is an opportunity to go a little more specific. Another frame of what you do is identifying areas where market forces or market demand would be really valuable, but there isn't any yet, or there isn't enough of it. In that sense, it was a specific cut on the climate problem: "I'm not going to solve all of climate, but there's a specific opportunity here, a specific wedge." What did it look like to arrive on that? And why did this orientation around an advance market commitment become this elegant blade or tool for this problem?

Nan: (36:25) The short answer is that I think it's just to the point of: what's the end goal that we're working on, and how do we reason our way back from it? That is the compressed version. The longer version is that with carbon removal, it is the canonical public good. You're sucking CO2 out of the air and you're storing it somewhere. Nobody wants to pay for that because the customer doesn't get a direct benefit from it. When you have no market of customers, you have very few companies that want to build anything because who are they going to sell their product to? You have very few investors because who are they going to invest in? The way that I framed the carbon removal problem back in 2019 for myself was: how do you build this? Then you say, "Well, who's responsible for solving public goods?" It should be governments. But I'm not a policymaker, so I felt I probably can't do anything there. In the end, it's going to be really important, but that's not where my skillset is. I was working in self-driving at the time.

Jackson: (37:20) I see. So there was enough similarity; it felt me-shaped enough.

Nan: (37:24) Well, the policy did not feel me-shaped. The piece I was trying to reason through was: you read the IPCC report and you're like, "Okay, we're going to need gigatons and eventually a teraton of carbon removal." Who's going to do that? Well, why doesn't it exist? Because there is nobody to pay for it. Can we get governments to pay for it? I can't, because I don't know how to do that. So who's the next best thing? Well, it's individuals or companies that have disposable income. Who has disposable income? SaaS businesses have pretty good margins. At the time, Stripe had published this blog post about buying carbon removal.

Jackson: (37:27) How much?

Nan: (38:07) A million dollars. Very small, but a thread. The theory of change around that was the right theory of change. Christian Anderson, who started Watershed, wrote this post. At the time, my friend Clay at Lowercarbon was watching me go down the rabbit hole and he said, "You should talk to these guys." The interesting thing about Stripe was that, yes, a million dollars is a good start, but Stripe has millions of businesses all over the world that are high-margin SaaS businesses. The distribution is there. If you can convince them to give a fraction of their revenue to carbon removal, you can potentially aggregate a lot more and use that to buy even more carbon removal down the cost curve. That was my logic as I was squinting and seeing the flywheel. It was through the lens of that problem that I thought, "Okay, this is the tip of the iceberg. There's a lot of interesting stuff here." When I joined Stripe, I did not know what an advance market commitment was. I could see the Stripe Climate piece of how we make this a product for Stripe businesses; that was the thing that got me really excited. We did that and it went really well. We got to tens of millions of dollars. Then we all sat in a room and were like, "Okay, well what do we do next? That's nice, but we’ve got to add another zero to this." AMCs, advance market commitments, were a concept that was developed in the context of global health. The general idea is there's a thing that you want to exist, and part of the reason it doesn't exist—in the original case, it was for the pneumococcal vaccine for low- and middle-income countries—is that we wanted pharma companies to work on this, but they didn't because who's going to pay for it? These are poor people in countries that won't have enough money to actually pay. The idea behind the AMC was to pull a bunch of money from, in this case, the Gates Foundation and a bunch of other countries, to say, "Hey, pharma companies, if you can make a vaccine to spec, there's a billion and a half dollars waiting for you." And it worked. So I cold-emailed the economists who worked on the original AMC: Michael Kremer, Rachel Glennerster, and Christopher Snyder.

Jackson: (40:12) There had just been one, basically there—

Nan: (40:15) Had been one and a half. So that was the first one. And then there was part of Operation Warp Speed that was also an AMC, and those same economists also—

Jackson: (40:23) And that was a different shape problem in that there was obviously lots of dollars for that vaccine. But there's this risk of: Pfizer develops it first.

Nan: (40:32) Yeah, that's exactly right.

Jackson: (40:34) But it's all about this playing with... it's like helping markets sort of collate on this equilibrium or something.

Nan: (40:41) No, exactly. It's fixing. It's saying, "Okay, we want this thing to exist." It doesn't because there is some incentive problem around the demand. And what is the intervention that will fix the incentive problem to get the suppliers or the developers to build the thing we want them to build? Everyone is exactly like you said; it's a little different. The original AMC was different. Operation Warp Speed was different. Frontier is a little different. And that just goes to show that you just have to study your problem and make a solution that works for your problem. Theory and practice are very messy, and that's okay because problems are messy. But that's sort of what we tried to really workshop with Frontier: in what ways does it differ and how do we modify the core model for the problem at hand?

(41:35) Focus and Sketching Out or Slicing Up Messy Problems

Jackson: (41:43) Speaking of messiness, to go back to the mature company versus early-stage company comparison: In a new company or a small company, the only thing that matters is focus on a single thing, get to product-market fit, and then grow it. Obviously, Patrick Collison has a lot of different areas of focus, and in some sense, your problem—especially in the early days of a new effort like this—is probably closer to the early startup founder, but the set of possible things to do is closer to mature Patrick Collison.

Nan: (41:46) Yeah, yeah.

Jackson: (42:14) And so I'm curious, even now, with Frontier and some of these other efforts, what does focus mean? Because you're hunting for somewhere else. You talked about making sure all of the most promising ideas are being worked on, which is like knowing the unknown unknowns, which just feels very broad. There are theoretically an unknown amount of important aspects of the climate stuff for you to be working on right now.

Nan: (42:41) Okay, well, when we say all the most important problems, I think in that context it's probably in the context of carbon removal.

Jackson: (42:44) Yeah.

Nan: (42:47) And—

Jackson: (42:49) Yeah, let's say carbon removal. Let's make it a little more narrow.

Nan: (42:51) Okay. I've been working on carbon removal since 2020, and we've been working on Frontier since 2022. So that is, in some sense, a lot of focus. It's been six years of figuring out what this thing is and getting it off the ground. We now have an incredible team. The team is cruising.

Jackson: (43:10) Maybe not a playbook, but there's a coherent strategy that needs to be updated, but it is moving. It has momentum.

Nan: (43:18) Totally. It has momentum. And there are still—not to discount—a ton of open existential questions, largely on the side of getting governments involved at the scale and speed that they are needed. But carbon removal is doing really well. And this woman on my team, Hannah, who basically founded Frontier—we founded Frontier together—she's amazing. She's been working on this for five years and she's basically running Frontier at this point. I think part of the reason that I can think about other things is because she's jamming it. She's really, really good, as is the rest of the team. Only when those things are true does one earn the ability to think about other things. I think that would be true for most leaders. Stripe is run amazingly well, and so that affords one the ability to poke around in other areas. But you've got to get the core thing humming first.

Jackson: (44:32) I think I was trying to ask a slightly different question, but that is actually very helpful. I was trying to say—and maybe it's worth jumping ahead—part of what it seems like you're good at, and you even talk about this in the context of philanthropy, is identifying the single highest leverage thing you can do with dollars. Ultimately, usually a relatively small amount of dollars gets the snowball rolling; it's the ignition piece of it. So I was actually asking a question about focus on the ignition piece. Maybe it's worth using some of the respiratory stuff as an example. It's a really big problem, and you're surveying the field, patrolling the waters, and looking for a place to go deeper on. With a company, it's sort of like finding some area of product-market fit and then just pulling on it for a long period of time. Whereas this, it feels like you have to have a constant awareness of other better strategies, especially in an area like—maybe showing my ignorance here—respiratory illness. Presumably the field is changing, biotech's evolving, and there are all these new developments. It was a question about focus in that sense: knowing where to best allocate resources in this continuous way. It's almost like you have to be way more paranoid.

Nan: (45:55) Yeah, but again, I don't know if that is that different from a company. The payments world is changing a lot right now, too, with AI and agents. There's a ton of paranoia. This is not at all my area of expertise, but everybody's having to adapt in every business. "How do I adapt my business to AI and the way the world's changing?" I don't know if that's so unique to this. I think the difference, maybe in some areas like carbon removal—and maybe this is more what you're getting at—is that carbon removal is a specific problem in that it was starting from zero. Nobody in the world realized that this was a thing that we were going to have to do at the scale we needed to until the 2018 IPCC report came out. So you're like, "Okay, sorry, we have to get from zero to what? And how?" You're trying to feel that out, and you're like, "Okay, we need to think about supply and we need to think about demand." We had to think about the markets to bring them together. The thing that maybe feels overwhelming is the ecosystem.

Jackson: (47:17) This is what I’m trying to get. It’s structurally overwhelming. Similarly, most of these problems that you’re giving examples of—respiratory illness, some of the stuff, some of the ideas Jacob has—it's just like, oh my gosh, how do I even have a chance of starting?

Nan: (47:31) Yeah, and I think it’s a great question. I think a lot of them, in some sense, it’s easier to start with a problem that has nothing because nobody’s entrenched in any worldview. carbon removal was a little easier in that sense. In some sense, the respiratory infections piece is a bit harder because you have different people who have different sort of fundamental beliefs, or "this has been tried," or—

Jackson: (47:48) —fundamental beliefs or "this has been tried," or...

Nan: (47:51) Exactly. And this is sort of like carte blanche. We’ll see what happens.

Jackson: (47:54) So—

Nan: (48:00) Yeah, and I think that’s actually a really fun creative exercise: how do you decompose the problem into its component pieces? There’s a supply piece, a demand piece, and an ecosystem piece. Each year we have OKRs in each of those buckets. But I think that one can...

Jackson: (48:14) That to me seems like the central GM skill, by the way: the decomposition of messy problems.

Nan: (48:18) The decomposition of messy problems. Yeah, I think that’s a good point—bringing structure to the messiness of these problems and making them feel tractable. I think a lot of big problems you see, and you’re like, "Okay, yeah, I’m gonna write this off because it’s impossible." But if you give somebody, even yourself, a sketch—just sketch it out.

Jackson: (48:43) This goes back to our vision conversation. It’s almost like if you could have a perfectly written 20-page memo on any problem in the world, it would be way more likely to be solved.

Nan: (49:00) Totally. I think that’s a great point. And there’s probably a role for more people—

Jackson: (49:02) Yeah.

Nan: (49:02) —who are doing the sketching.

Jackson: (49:05) Yes.

Nan: (49:07) And the sketchers and the GMs don’t have to always be the same people. People who know a field and are good at the decomposition piece are good at setting out what the world should look like and what’s a rough path to get there. Maybe it’s wrong, but it gives people something to react to.

Jackson: (49:26) Also, just frankly, even in companies, amazing tacticians and strategists are often not the people with grand visions.

Nan: (49:34) Yeah. It’s amazing if you can find them in the same people, but sometimes they’re not.

(49:39) Legibility, Public Rallying, and Ambition in Philanthropy

Jackson: (49:39) Is it important for people like this to be a mascot for it? Increasingly you have dialed up how public you are about some of this and, frankly, some of your other work recently on philanthropy and GMs. Maybe another way of asking the question: how important is the legibility aspect of it?

Nan: (50:05) The legibility of which part?

Jackson: (50:06) A problem? Having a flag bearer who’s doing part of this. Like the person—

Nan: (50:12) —who wrote the memo—Lewis Bollard—on ending factory farming or something like that.

Jackson: (50:18) Yes. "Are you going on enough podcasts?" is a silly way of asking this.

Nan: (50:22) I think that it depends. I don’t mean this to be a cop-out, but it’s just working backwards from what is the thing you’re trying to do. Is going on podcasts, the comms and marketing piece, a really important piece of it? I would argue in the case of factory farming, getting more broad individual support and political support for that cause is a part of the strategy. Does that matter as much in carbon removal? I don’t know. Does it matter in getting more people working on interesting problems? Yes. I think the writing about it... the thing that motivates me to write is usually when I think there's a thing I want to happen because of it. A thing I do feel really fired up about these days is finding really awesome people to work on more important problems for the world. There’s so much money coming into philanthropy in general, and I think we are really short on founder-shaped GM people to man those problems. So I feel more urgency to bring attention to that because I want more great people working on more great problems. But it's not from a... I guess the legibility, I think, is downstream of the problem.

Jackson: (51:52) For me, part of the thinking behind my question is Silicon Valley is quite good at... take someone like Marc Andreessen. One of Mark’s centrally, singularly great skills—maybe not singularly, but rare and important—is his ability to create a meme around a thing. Software is eating the world, American dynamism, whatever. You can make a pretty strong case that Mark’s often not first to these things—Founders Fund was investing in whatever—but he’s good at creating this gravity engine around it. Even something like the term GM, which obviously you didn’t make up, but in a little corner of the world has a little more buzz. My sense is one of the main reasons we don’t have more people working on these things is because they are less legible. Famous examples of people who are doing this in an awesome way. If you could point to... the average 25-year-old in Silicon Valley can name 10 founders who they want to be like.

Nan: (52:50) Right. But they’re not like, "Oh my gosh, Henderson eradicated smallpox and I want to be just like him."

Jackson: (52:55) And forgive me if this is rehashing, but do you feel like you had to lower your ambition to work on public goods?

Nan: (53:01) I think when I joined Stripe to work on climate initially, my friends were like, "Excuse me?" They were sort of like, "What is going on?"

Jackson: (53:04) Yeah.

Nan: (53:25) But mostly just because I was working in self-driving and doing product stuff. I personally think it's an increase in ambition because you are taking on more consequential problems, and they’re harder.

Jackson: (53:42) No, my implication was not that it's less ambitious, but paradoxically, there is something about it where, if it works, it's way more ambitious if you make a real dent on it.

Nan: (53:56) That's true in startups. Lots of people fail in startups.

Jackson: (53:59) It's true.

Nan: (54:03) I think we love a good power law applied to startups, but we don't do it for philanthropy, almost because we don't believe it.

Jackson: (54:10) Yeah. I think at the root of it is probably: what are you going to do, extract a teraton of carbon?

Nan: (54:15) Yeah, good luck to you. I think it's this odd discontinuity. We are very comfortable with a hits-based approach in VC in the private sector, but we don't take that approach in the philanthropic sector. And as a result, we probably don't get the kind of outcomes that we want to get.

(54:38) Third Wave Philanthropy and Hard to Quantify Problems

Jackson: (54:38) You wrote a great piece on modeling a third wave of philanthropy. And really, what I think is so compelling about it is you borrow from Silicon Valley. You have this triad of—in the startup sense—LPs, VCs, and founders; and in your sense, funders, allocators, and builders.

Nan: (54:57) Our conversation was really helpful, actually, in helping me piece that together. So I'm very appreciative of that.

Jackson: (55:00) I'm glad.

Nan: (55:03) Yeah.

Jackson: (55:09) In some sense, you're trying to pull all of those forward, and it's a little bit of a three-body problem or a three-part chicken-and-egg problem. Maybe the first question would be: does the GM frame apply to all three of those roles?

Nan: (55:24) I think probably.

Jackson: (55:26) You are kind of two of the three of them, if I understand correctly, which is you are both a capital allocator and a builder. Is that right? Or do you think you're closer to just an allocator?

Nan: (55:48) I think that the GM is a mindset. I think we kind of straddle. I think we are technically in the role of the capital allocator—if you had to put Frontier in one, that is where we would be. But I think we do wear lots of different hats. We are spending a lot of time trying to get more capital by working on the policy pieces to get more policy-driven demand. We're working a ton—if we find really promising carbon removal areas that we don't see worked on, we're trying to get them going ourselves. So I think our primary role is that of a customer in the form of a capital allocator. But we are—

Jackson: (56:31) It's a lot like the most ambitious VC firms, though. They're going to incubate companies. You have Mark Andreessen spending all of his time fundraising all across the world to figure out how you can have a $20 billion fund versus a $10 billion fund, whatever.

Nan: (56:34) Yeah.

Jackson: (56:46) What is the typical builder in the Frontier context?

Nan: (56:51) Companies working on carbon removal. So that's a direct air capture company, a surface mineralization company, an enhanced weathering company. There are lots of different pathways. It would be a company saying, "We have an approach that we think can be really big and really cheap. We sell carbon removal. Who's going to buy it?"

Jackson: (57:09) These are primarily companies, though, not nonprofits?

Nan: (57:11) They're companies, yeah.

Jackson: (57:17) And do you think most of these types of problems are more likely to shape that way? Is that due to the market shape of carbon removal? Is it because of the advance market commitment aspect of it? If you were to try to generalize to the broader new philanthropy orientation, presumably most of the things the OpenAI foundation is funding aren't going to be companies?

Nan: (57:38) Yeah, I feel it's so area-specific, so I don't know exactly what the generalization is here.

Jackson: (57:46) Or a better question would be: structurally, why are most of these people working on the climate stuff, carbon removal stuff, forming companies?

Nan: (57:55) Well, it's kind of like in sanitation. You need people to pick up the garbage for your city, but those are companies that you pay to do a service. And for carbon removal, we need a lot of sanitation companies, but for the air. But there is a supply and demand element in carbon removal that may or may not be the case for other EA problems.

Jackson: (58:20) So if it can be a company, it probably should be a company.

Nan: (58:22) Yeah, I think so. I think that's the right way to think about it. And the only way that there can be companies is if somebody is buying their product. So that was the market mechanism that we were fixated on. But every problem is not that generalizable. If you're working on biosecurity or AI safety, is it a supply and demand problem, or is it a policy or regulatory thing? Is it an evals thing? It's so specific to that problem that I don't think it's that useful to generalize.

Jackson: (58:55) And there's probably an element, too, of the thing you're trying to do being very clearly targetable and measurable. I think in carbon removal, we know exactly what we're talking about—or maybe not quite exactly—versus something more ambiguous, something more philanthropic, like "we want to increase the beauty of cities." I mean, that's an extreme example.

Nan: (59:26) Yeah, I think that this is one of the things that we're going to collectively struggle with with this round of the third wave of philanthropy. The way I was thinking about it was that the first wave of philanthropy was the Carnegies and the Rockefellers. The second round was the Gateses of the world and, to some extent, parts of EA, although that sort of bled into this third wave as well. The second wave of philanthropy is very measurement-oriented. It was DALYs and cost-benefit analysis and how do we do the thing with the highest ROI. That has generated a huge amount of good for the world, and we should be very grateful for that skill set that we got from that wave. In my opinion, a lot of the questions that we're going to be grappling with now from a public goods and moral perspective are harder to quantify. There is a lot around AI safety and how we navigate this transition through AGI, if we do get successfully through that.

Jackson: (1:00:42) things, what's our vision for the world?

Nan: (1:00:43) Vision for the world. What does meaning look like? What does good look like? What does beauty look like? I think these are maybe not the most urgent questions right now, at least for some of these funders, but they will become important questions. And they don't lend themselves very well to cost-benefit analysis. I think that's going to feel really uncomfortable for many of us who grew up very familiar and comfortable with those tools, but those tools are not quite the right fit. I think that the types of things in that bucket are going to take—we're a little anemic there. We don't have a lot, maybe, to—I think we're going to fumble around for a while to try to figure out how we even jumpstart answering those questions in a substantive way. A hope that I have is that we don't just do the AI safety stuff in the next one to 10 years. We also start to give this second bucket of stuff more attention, because I think it's going to take us some time to get our sea legs and figure out which way is up.

Jackson: (1:01:58) Do you think it's fair to slice that as sort of like the last round of philanthropy? Probably also stuff like carbon removal to some degree, or even AI safety, is more about floor raising or downside mitigation. And this other bucket you're describing is much more about raising the ceiling, right? And granted, there are probably a lot of people who would be like, "Upside problems—we'll deal with those later. People are dying."

Nan: (1:02:21) Yeah.

Jackson: (1:02:29) Or the Earth's—another thought I had is that in some sense, the carbon removal problem, despite the fact that a lot of progress wasn't made on it, is actually more of a wave two of philanthropy type problem that it would be good at solving.

Nan: (1:02:42) Yeah, I think that's right.

Jackson: (1:02:43) And for whatever reason—intractability or whatever—not a lot of progress was there. But we're going to increasingly have a new set of problems which are like, "What do we want life to look like?" And should philanthropic dollars even be the way we improve them?

Nan: (1:02:57) I think that's right. And how do we answer the question of whether philanthropic dollars are the right place to start? I think it comes back to the vision piece: what do we want the world to look like here? How might we imagine what "great" looks like for humanity, for ourselves, and for our city in some period of time? Working backwards from that and saying, "Okay, are these companies? Are these funding more writers? Are these funding more artists? Are these figuring out what the next moral framework is that is maybe not Christianity or Judaism or EA, but a third thing?" I think these are sort of big, squishy questions that are just going to take time for us to figure out. So I'm kind of eager to get cranking on some of them.

Jackson: (1:03:51) In some sense, will it just kind of come down to the moral hierarchy of the rich people and the OpenAI Foundation?

Nan: (1:03:54) I think—

Jackson: (1:04:03) And—sorry to interrupt you—Ross Douthat wrote an interesting response to your piece. I thought it was cool; he made a strong case for making more beautiful things in the world. And yet it's also like, well, that's great, but we still have crazy amounts of poverty in the world. Presumably—I don't know if some Anthropic employee is listening to this, trying to decide where to spend their new fortune—I suspect it's probably pretty hard to in earnest say, "I'm going to spend it on beautiful buildings," when... maybe this is too EA of a mindset or whatever.

Nan: (1:04:32) It is very EA mindset, and there's a lot to love about that.

Jackson: (1:04:35) Yeah, yeah.

Nan: (1:04:37) I don't know the answer to that question, but I wonder if there's a little bit more room for a portfolio of approaches here and if we have to so strictly adhere to a single one. I think it feels a little bit hubristic or naive to think that everything is captured in a cost-benefit analysis that we can put into a spreadsheet. A lot is, so I don't want to minimize that at all, but I think we can all feel that something isn't quite always captured in that lens. That's not to say we shouldn't fund all that stuff, but there's probably a bit more space for some of the squishier stuff. And whether that's 5% or 10% or 30% of the portfolio funding, I don't know—and it's not my decision to make. But should we be a little bit more experimental in thinking about that, especially and acknowledge that some of the questions are just different? I guess if somebody was really set on the cost-benefit piece, one way to reason through that with them would be: one might believe that in a post-AGI world, we're living in this age of abundance. In that world we have ticked through most of the things on the spreadsheet. But the squishier things are just going to take more time to figure out. So let's use the time we have now to our advantage and start to get some of that going. I'm not sure that those problems can absorb so much capital right now even if we wanted them to. I have not looked at it, but that is my intuition.

Jackson: (1:06:34) You need some kickstarting, some snowball rolling.

Nan: (1:06:37) Yeah, exactly. And that's probably not that expensive. So maybe we should just do those things, and then at least we have the option down the line to expand them. There's a time element.

(1:06:50) Risk Tolerance in Philanthropy and Scarcity of Funders and Allocators

Jackson: (1:06:49) Maybe this is slightly tangential, but I think it is quite related. Inside of this is actually—and you and I have talked about this—philanthropic dollar spend typically tends to be far more risk-averse than venture capital or other forms of investment. I think there are a million reasons for that: bureaucracy, all these other things. But one reason might actually be that people don't want to be criticized for spending their money on beautiful buildings when they could have spent it on malaria nets or whatever. So on some level it actually is going to require—

Nan: (1:07:21) Which is a shift, by the way, because philanthropy used to be funding the New York Public Library.

Jackson: (1:07:29) Yeah, yeah. So that's an interesting point. There is a resistance to being divergent, in the same way that I'm sure the average venture capitalist right now, in 2026—if you're not funding AI, you better have a pretty good reason. And by the way, I would probably argue that you're more likely to find something really interesting outside of AI now—maybe not more likely, whatever.

Nan: (1:07:49) Because everyone's looking at that.

Jackson: (1:07:51) Right?

Nan: (1:07:51) Yeah.

Jackson: (1:07:51) Right.

Nan: (1:07:51) So anyway, there's a — it's like the non-consensus.

Jackson: (1:07:54) There's a pressure to be super consensus in philanthropy. One question — and this may be silly — but one question I found myself thinking about and asking is your setup has two scarcities: you and Patrick, basically. And that's doing a lot of extra work, but basically the allocator or the funder and the ambitious person that could probably go be working in something else or starting a company or whatever. I think it's in the GM piece you had laid this out for part of why at least the funder dynamic is scarce. You say in practice this means funders who: one, back an ambitious problem and want to solve the whole thing versus a slice of it; two, resource it well; three, give their leaders genuine autonomy to do whatever is needed to solve the problem; four, compensate these leaders competitively; and five, commit to sticking with the problem for a very long time. Again, the pithy question is: which of those two roles do you think is actually more scarce in this ecosystem now? People like you or funders like Patrick? And then I think there's a lot of follow-up questions.

Nan: (1:08:56) I don't know the relative scarcity, but I think they are both really scarce. We have a really unique setup in the context of our public goods work at Stripe. All of the things there are true. The question I get most when we're hiring a new person on the team is just skepticism, coming in and being like, "Is this real? What is going on here?" Or, "Could Patrick just get bored or distracted?"

Jackson: (1:09:25) Tell them, yeah.

Nan: (1:09:26) "Are you going to shut it down? Go public?"

Jackson: (1:09:27) They're like, "Why are you doing this?"

Nan: (1:09:28) Totally. "Are you going to shut it down? Will priorities change? It's not the core business. Are you sure you're not spending all of your time jumping through bureaucratic hoops?" I get the skepticism because I think at most organizations that is true, and it is not the case at Stripe. So, Patrick and John have just created a really — I feel really lucky because we have sort of these perfect conditions to take on really long-term projects in really higher-than-usual risk appetite ways. We have — I think in part because we've executed well consistently over a long period of time — earned the trust to continue to do that. But the generalizable piece, in my opinion, is that this is replicable. More companies, I think, could house organizations like Frontier and this new respiratory infection initiative. When we were starting Frontier, my instinct was to spin it out of Stripe because I was like, "This is getting really big, bringing in money from other companies. We shouldn't do this in Stripe." And Patrick was like, "I think we should keep it in Stripe." One of the reasons was we want to shepherd this for the long run. And the other reason was that we can pay people tech salaries while working on this, and so we're going to be able to attract better people. I think that those are very non-consensus approaches to philanthropy, and they really make a difference. Those are sneaky advantages that we have, and I think those are replicable by other companies. In theory, those are things that leaders at other organizations could decide to do. They could decide to say, "We also want to take on really big problems. We're going to pay people who work on these public goods like other people at our company." And we are going to protect them from any processes that don't apply to them. They are different from the core companies. We're going to protect them, and we are going to pay them reasonably well. I think that's a sneaky huge arbitrage for companies.

Jackson: (1:11:51) Two thoughts. One is, I think it's telling that Patrick's done this in different forms. All of this is a part of Stripe, but Arc's a separate thing, he's doing this stuff with Tyler, whatever, which is another nice example of sort of downstream of the problem figure out whatever why. I don't want you to speak for him, but I understand the point you're making when you say it's replicable. On the other hand, it's like this happens because — out of the goodness of their heart, more or less. Is there a real business case for this stuff?

Nan: (1:12:26) No. I mean, I think in the really long run we are interested in economic growth, and climate change is a threat to that. People getting sick from common respiratory infections is also a threat to that — probably half a percent to 2% of GDP every single year. So that is not trivial. But over the really long term, that is true. In the short term, these are revenue-destructive. We spend a lot of money on carbon removal that we do not recoup. I've never been asked that. That has never come up in a conversation. But I think you're right that these hyper-smart, conscientious, souls-oriented-in-a-good-direction... those are hard-to-find people.

Jackson: (1:13:27) To go back to the scarcity question, do you think that there's any world where you could be doing something like this somewhere else?

Nan: (1:13:33) I think that the tectonic plates are shifting right now a lot in philanthropy. So I hope the answer to that question, whether it's for me specifically or just in general... Yeah, I think there are, and I think that there definitely could be. When we think about how philanthropy is changing, one of the reasons for the change is that there's a lot of money coming in from OpenAI by the OpenAI foundation, from Anthropic founders who pledged to give a huge amount of their money away, and Anthropic employees who have taken advantage of this really epic employee matching program that the founders put in place. There's also lots of other money from people who are second-order beneficiaries from that. Maybe SpaceX folks end up being philanthropically minded. But the point is that there's a lot of new philanthropic money coming into the space. The types of funders who are behind the money grew up in Silicon Valley. Their orientation is: "We want really smart, fast, nimble hustlers to own a problem and deliver results." That has the potential — the combination of the funding and their orientation around the talent and the fact that the problems that they're worried about are very time-consuming.

Jackson: (1:14:53) Their worldview, by the way—it's actually not software people as much; it's AI people, which is almost a different genealogy there.

Nan: (1:15:01) Yeah, exactly. And the worldview of that type of person is like, "Okay, we gotta move fast." So all of those things, I think, have the potential to come together to embolden and fund and catalyze this whole new wave of philanthropic founders.

(1:15:22) The $40B Tidal Wave of New AI-Money and Why Start Now

Jackson: (1:15:21) Make Patrick less scarce, on some level.

Nan: (1:15:24) Yeah, exactly.

Jackson: (1:15:24) In that piece, you basically—to put some numbers on it—you say, I think your conservative estimate's like almost $40 billion a year of new philanthropic dollars that are coming in. I think the total number now is about 600 a year.

Nan: (1:15:38) Yeah, 600 a year in the US.

Jackson: (1:15:42) You have all these great—it's like, whatever, 5,000 IFPs and however many Arc Institutes and so on. Realistically, there's just no way that we're going to have enough things to fund like that.

Nan: (1:15:45) Yes.

Jackson: (1:15:56) So what do you actually think is going to—I mean, part of this is the reason you wrote the post—but what do you actually think is going to happen over the next two years, let's say?

Nan: (1:16:07) Well, I think that without significant intervention, I don't know.

Jackson: (1:16:11) The money just won't get spent.

Nan: (1:16:12) Yeah, I think the default is that the funding materializes but doesn't actually go anywhere because funders are like, "I'm not finding these amazing projects that I want to put the money towards." But part of that is in our control to fix. So what I hope happens is that we can see this tidal wave of funding coming down the pike and we figure out how do we better characterize the problems that these funders want to fund and that the world, quote-unquote, "should solve." What is the pipeline of talent from, you know, people working as a tech PM that maybe they want to get into a different type of thing? Or they're attracted to these hyper-ambitious, kind of public-goods, good-for-the-world shape problems and now have a path to actually being able to work on them unencumbered.

Jackson: (1:17:07) But you're sort of speedrunning saying it's like the cultural aspects of this are like venture capital in the 1980s and we're about to have the funding level of the 2010s. It's gonna happen fast.

Nan: (1:17:16) Well, okay, I think it will happen fast, but also it's gonna take the funders time to build the muscle to spend the money. It's a lot of money to move, so it's not gonna ramp up immediately. That's gonna take time. And I think there need to be capital allocators to help facilitate the deployment of capital. That's a whole shape of—sorry, of founder that needs to exist in addition to the builders. But I think the thing to take away here is that there's a lot of money that is going to be pointed at really interesting and important problems for the world. And the thing that is gonna be needed is really talented, amazing people to GM the problem and to figure out the path forward. I think that what funders, I hope, do is give these founders the space and the breathing room and the non-administrative—

Jackson: (1:18:12) This is the quote I read about Patrick, right?

Nan: (1:18:18) Yeah. I think if the thing that I would be most anxious about in any of these cases is—I don't want to work in an environment where I'm going to be hamstrung by having to produce random reports all the time. That is the most... I would take a crazy pay cut to not have to deal with that. Yeah. And I think that that is on the funders to figure out, "How do I make sure?" Because the pull is always in that direction. So how, as funders, are we sort of self-aware of saying, "Okay, I'm going to push back against that"?

Jackson: (1:18:48) And also, "I'm going to fund the weird stuff."

Nan: (1:18:51) I think there's going to be natural interest in funding the weird stuff from this set of funders because they like the weird stuff. I think the main—like, Anthropic IPO, I don't know, in a year or something like that, or maybe later this year, and then there's a lockup period and so on. So maybe funding becomes available in a year. It's gonna take—if I decide today that I find a problem that I want to work on, I have to quit my job, I have to learn about that problem, I have to ramp up on that problem. I have to figure out what is my strategy, find funding for that, find a team for that, figure out how to work with my team. That's gonna take a year to build up some basic capacity. We gotta start that now. The time to get going on that is now so that in the next couple of years there is—

Jackson: (1:19:35) Well, and the exciting part maybe, if you're the entrepreneurial person, is the funding is, in a way that it hasn't really been before, going to be there. And it's very—not "low-hanging fruit," that's probably a silly way of putting it—but much more like the grants are out there.

Nan: (1:19:38) Yeah. Yep.

(1:19:53) Amount of Capital, Government Philanthropy, and Making Philanthropic Founders Rich

Jackson: (1:19:53) What is—maybe just a few miscellaneous questions on this stuff. One is, back to the snowball idea, usually actually the highest-leverage thing is to spend a small amount of money on getting something rolling. When does the size of the amount of funding really matter? Presumably, one other way this could be shaped is we're talking orders of magnitude—billions of dollars being given away, possibly to individuals, who knows? Or at least hundreds of millions. Maybe it's the Coefficient Giving thing, it's really small or whatever. When does a large amount of capital really, even for something like what you do, move the needle? Presumably, something like Frontier is a dramatically different orientation than the $10 million Stripe was giving away. But is it about a proof point? Is it about a repeatable kind of funding mechanism?

Nan: (1:20:42) I think it's too problem-specific to answer that. But I think the generalizable thing is, in most cases, a new problem isn't going to be able to absorb $10 billion right off the bat. You can't even.

Jackson: (1:20:56) It's another reason you have to get started sooner.

Nan: (1:20:59) Exactly, exactly.

Jackson: (1:21:01) Got it.

Nan: (1:21:01) Exactly.

Jackson: (1:21:01) Any sense on the types of problems that are better served funded by private philanthropy versus government?

Nan: (1:21:08) That's a question I feel that I need to have a better answer for myself. I don't know. In some sense, I do feel that carbon removal should never have been private sector driven. I think that is a little insane. But you go to war with the army you have. When should—what are the kinds of problems that are better for governments than philanthropy? I mean, I guess, in theory, not all philanthropy is in the general... there's a scalability, like how broadly might it serve the public's interest? Maybe philanthropy is sort of better positioned for more, I don't know, specific or hyperlocal things in a way that governments aren't. But I don't know. Do you have an answer to that question?

Jackson: (1:21:54) Well, I guess some political view response to this would be like, these people shouldn't even be this rich and should be taxed way more—more like the government's job is to do philanthropy. The private sector shouldn't even be doing it. I think a very strong counterexample would be something like Frontier, which is like, turns out the government doesn't always solve the problems we have. I'm sure there are people who think that the OpenAI Foundation should be deployed by the government.

Nan: (1:22:21) Yeah, I think that is not the case. Okay, that might be true. And I am not one to speak about what is the fate of these AI companies in the long run, but I—

Jackson: (1:22:45) Yeah, the more interesting question, to be clear, I think is about the types of things the government is good at funding. The government is good at funding certain types of things, and it's not as good at others. And part of it is just whatever the—maybe the answer is actually as simple as just, what are the areas that the government is not funding enough? Like, go nuts.

Nan: (1:23:03) But that's different. I feel like there's a difference in the question of what should the government be funding and what does the government fund? And I think that, in reality, a lot of the philanthropy that we're seeing is going to fund gaps that the government is not doing. Now, I think that, in theory, both philanthropy and governments are in the interest of the public. They're interested in sort of, "How do we better serve people and the world?" And I think that, in principle, they should maybe be interested in very similar things. Now maybe there are differences because individuals might have different worldviews of what does serve the public. And so the government has one worldview, and so a philanthropist might think, "Well, I don't agree with that. And so I want to do this other thing. And I value this a lot and the government doesn't." But they're both broadly aligned towards serving the public. Another way that they differ is that philanthropies are smaller than the government. There are probably things that the government can fund that individual philanthropists can never do. Now, the OpenAI Foundation has a lot of money, so it's more government-like.

Jackson: (1:24:14) Right. This is the tension, I think.

Nan: (1:24:16) Now you're kind of getting at—because some of these dollars, depending on where AI company valuations go, could get really, really big. I think that there is this question of, I don't know, maybe they could start funding things at that size.

Jackson: (1:24:32) If Anthropic gets to a certain size, should they be doing the UBI?

Nan: (1:24:36) Yeah, UBI is—yeah, I don't know how to think about that.

Jackson: (1:24:40) But it is that kind of like, at some point you get to a level of scale, or healthcare, or whatever it might be.

Nan: (1:24:47) And I think that really the sort of worldview and orientation, and the character and morality of these funders and organizations—because of the potential scale here and because of how concentrated it is—end up mattering quite a lot.

Jackson: (1:25:05) Do you think we'll ever get the level of ambition required if there isn't a clear path forward for "philanthropic founders" to get anywhere near as rich as non-philanthropic founders?

Nan: (1:25:19) I think that's a really good question. Conceptually, I think it is sort of silly and a little crazy that we're like, "Okay, if you solve this amazing thing for the world, we still expect you to take a huge pay cut." If one delivers a great outcome for the world, we should make them rich. That's great. And I don't really actually know where the whole "one has to self-sacrifice in so many areas to do philanthropy" came from.

Jackson: (1:25:53) I don't know if it's that. I think it's actually the inverse, which is just in companies—I mean, the reason Silicon Valley has created so much wealth in a way that's even distinct from finance or whatever is ownership. Larry Page made Google and, as a result of it, owned an ultimately fairly small part that's worth a ton of money. Maybe there's something like an advance market commitment as a bounty, somehow. But it's actually closer to the advance market commitment problem, which is there isn't enough demand. Who's paying?

Nan: (1:26:27) Well, you want to pay for outcomes is sort of what you're getting at, right? I think you talk to some folks in AI and they're sort of like, "Eventually an ASI will allocate rewards based on people's relative societal contributions." And I think that is maybe on one end of the extreme. I think another way to think about this is—you know, look at the typical company. How do companies compensate for performance? Well, there's a base salary, but there are oftentimes performance incentives. Like you're getting a cash bonus, or you're rated based on how well you've done in a given year. And some of that is outcome-based, but some of it's a little squishy, but it kind of works. It's a half-objective, half-subjective measure. It works for companies. I'm sort of like, why can't we do the same thing for philanthropies? If the funders determine that a founder is killing it, can we pay them more? I think another interesting dynamic, and a very unique dynamic about this wave of philanthropy, is that the money coming in is currently sitting as equity in some of the most valuable companies in the world. The most coveted equity in the world. And so can we use that to the advantage of these problems to say, "Okay, if a founder kills it, can we pay them a performance bonus in the form of Anthropic stock?"

Jackson: (1:26:30) Yes.

Nan: (1:28:08) I think that's like a sneaky, cool, unusual piece. This is not the first time people have had a version of the "we should change performance incentives in philanthropy" idea, so part of me thinks this is a dead end. And part of me wants to hire like a cracked-out lawyer to figure out how to do this.

Jackson: (1:28:28) It's done. I mean, you don't have to confirm or deny it, but presumably you have equity in Stripe.

Nan: (1:28:31) Yeah.

Jackson: (1:28:33) And that is a really good incentive for someone who would—yeah, right.

Nan: (1:28:39) And I think there's a generalizable version of that, now that we have the funding that's sitting in equity. And it's a lot of money, huh?

Jackson: (1:28:49) Yeah. Conversely, though, you still have the ownership problem. It probably looks closer to a highly competitive high-frequency trading bonus structure. Part of the challenge, too, is you just need more competition. Currently, these funders don't have to pay out that much in philanthropic outcomes because the most ambitious... yeah, it's— The reason the bonuses are so high in HFT is because there's a hell of a lot of competition. In this domain, there's a lot less competition. And so the best people are in less demand. As a result, you're like, "Oh, cool, you did a good job on your nice philanthropic thing. Here's an extra hundred K." Again, part of this is that you're never going to get a bonus at the level of startup equity. So there is the ownership thing that maybe you solve. It's a cool area to—I mean, the other way you solve this is you just have more. Bill Gates was quite innovative in terms of how he thought about philanthropy. And we're going to have some really rich people and they could be quite creative for how they think about, like, if somebody solves this problem, here's a hundred million dollars.

Nan: (1:29:55) Yeah. I mean, I think that—okay, so there's the bounty or the prize model. I think the challenge—

Jackson: (1:29:58) Yeah, yeah.

Nan: (1:30:01) With that is, if it takes you like 20 years, you have to self-fund during that time.

Jackson: (1:30:04) And also, who do you recruit? Yeah, yeah, yeah.

Nan: (1:30:11) But my instinct is that there's something here around the pay piece that we do have to look at. Right now, if we want the best people working on the most important problems for the world, we are going to have to get creative about how to compensate them. And I think that we don't have to let the perfect be the enemy of the good here where we can borrow a lot from the private sector. We can borrow a lot about performance incentives and bonuses, etc. I'm not convinced we have to totally reinvent the wheel.

Jackson: (1:30:39) Yes. And yet you're currently relying on someone like Nan Ransohoff being like, "I'm going to—" Ultimately, in the end, I think your decision to pivot to Stripe was a good one. That was probably not that obvious back then, especially when it came to having people take the gambit that, one, I'm going to maybe sacrifice my total earning potential and maybe this is going to evolve in a new way. These pieces are all going to have to be put together.

Nan: (1:31:13) It's kind of like a trust-fall kind of vibe. But I think that that is also a tractable problem in and of itself. Imagine, what does a sort of YC for philanthropic founders look like where there is some sort of—even if it's a small batch—you're saying, "Okay, for the best folks who come out of this, there's this much funding reserved for you in the format of equity in X company" or something like that? You give people a bit more, and you don't have to fund everybody. YC doesn't fund everybody. Totally.

(1:31:44) Nan's Mid-Career Inflection Point and Getting Off the Obvious Path

Jackson: (1:31:44) Yeah. I talked to a few people before this conversation, and speaking of the pivot and the transition, I think you're someone who very much inflected your life in a non-obvious way. Not that early—you weren't in your early 20s.

Nan: (1:31:47) Sure.

Jackson: (1:32:05) Maybe to set the tone, you were talking about the marriage question and why it was meaningful to you. And you said, "But if I had to summarize the net effect of this book on me, it was a massive infusion of courage not to snap to grid, to not snap to grid by default for big life choices." I think, in talking to other people about you, there's just an overwhelming sense of someone who was super ambitious along a static ladder and then somehow you got off the main highway. Maybe two questions. One, what did you have to sacrifice? Or did it feel like it was actually sacrificing something? And then two, for other people out there who probably have some semi-conscious or partly conscious feeling of, "Yeah, I'm doing pretty well. I've done the thing"—you talk about this in the context of millennials really well, which is chasing the gold stars—what advice would you give them? To the people who know that maybe there's some other path out there, but it feels like they're too far along?

Nan: (1:33:20) I would definitely have self-described as really good at playing the game. I was good at the gold stars. I was good at school. I kind of did life as I was supposed to do it. I got into good schools and got good jobs and got married and got a house. And then there was a series of things that happened in my life, including a sick parent and a 15-year relationship and marriage coming to an end, and then COVID. That all ended up coinciding around the same time. The combination of those things shook the foundation of everything, I think, in some sense for me. I think there was a lot going on during that time and it was very fear-inducing for somebody who was very much on the path. The fear around getting off the path was incredibly overwhelming for me for many years. Getting through to the other side of that and realizing that my life didn't fall apart, and some things that I was really scared of—the things I imagined were going to be the worst things ever—did not materialize. Our brains are very creative in that way. Then realizing that the space that was cleared from this new phase was an opportunity for all this new stuff to grow. Developing confidence to listen to my own instincts a bit more and listen to my own interests and curiosities a bit more happened through that process. The combination of those things, while deeply painful at the time, were very important for my growth as a person. If you step off the path, nobody really cares that much and nobody's really paying attention. It feels better because it feels more like you. I think I've upweighted how much I'm trying to understand and live in accordance with my own values and self and less what I'm "supposed" to be doing. But that was a real unlearning process. I have great parents and they're amazing, and I think I just kind of also "got got" by the system that many of us get got by. I look at people, especially in San Francisco, who have gone their own weird, zaggy ways really early in their lives, and I feel some envy of them. I wish that I had gotten there sooner, but I didn't. But you could still get there.

Jackson: (1:36:32) There's hope yet.

Nan: (1:36:34) There's hope yet. And some people never get there. I think for me, I probably needed to have some of—I think I was so fixed on the path that things needed to get a little bit messy before I could really kind of get there. But other people may not be as well.

Jackson: (1:36:45) I think the hard thing is it compounds.

Nan: (1:36:48) Yeah.

Jackson: (1:36:49) The reason most people don't ever get there is because after a certain age, you kind of just stop assuming that—inertia's a thing. Another maybe related part of this is just lots of people who describe you as super hardcore and fun.

Nan: (1:37:05) Oh, that's nice.

Jackson: (1:37:09) And just lots of dimensionality. I'm sure part of it is related to what you just said, but maybe a theme that has come up in lots of my conversations with people I admire is managing to hold both deep seriousness and intensity and lightness. I'm curious if there's anything that comes to mind for how you create that or foster that. Because, by the way, maybe there's some feeling of, "Oh, I wish I had found my weirdness sooner" or something. But I think part of what makes you you is also your seriousness and intensity. And maybe part of that came from— But...

Nan: (1:37:54) Yeah, it's so hard to know what my life would have looked like had I taken a different route. I think I've become less rigid and probably more fun over time—in part because... more fun, I don't know about that, but definitely less rigid over time. We all take Myers-Briggs; we're all forced to take Myers-Briggs at some point in our lives. I used to be a really strong J, and I've become like a soft P now. And, whatever, this is all kind of pseudoscience stuff.

Jackson: (1:38:23) One of your friends described you as the only person they know who is going from Kiki to bouba in their 30s.

Nan: (1:38:30) Yeah, for sure. I think that's true.

Jackson: (1:38:31) It's about as scientific as Myers-Briggs.

Nan: (1:38:33) I think that's a great summary. And part of that was, I think, just the exhaustion with the kickiness of it all. I think I just kind of was like, this isn't that fun for me. I've kind of been there, done that. There were people that I did encounter—Ryan Orbuch, who we worked together early days on Stripe Climate. He was one of—even though I lived in San Francisco for a long time, I interestingly was in a very different part of San Francisco. Ryan, I think, is one of those people who is just always following his curiosity, and he's sometimes a little disorganized, but in a really fun way. I think that that was very shocking to me at the time. It was a very helpful way to see. I now actually have many friends that are sort of versions of that, but it was very helpful to see what that looks like and permit myself to not be as—I just kind of loosen the grip on things.

(1:39:47) Grab-bag: Why Stripe Funds Public Goods, Making Things with Friends, Creative Partnership, Iceland Drone, and Scone Heads

Jackson: (1:39:47) Speaking of Ryan, he told me to ask about a lost drone exploring carbon removal projects in Iceland.

Nan: (1:39:55) Oh, yeah, we went to Iceland to look at some carbon removal projects in 2021, maybe. We were driving around, there was a film crew we were bringing with us at the time, and they wanted to fly a drone over the car as we were driving. But the guy who was controlling the drone lost service with the drone, and it ended up going down in this massive field of identical rock and moss. You just—it was the perfect camo conditions for a drone. So for two hours, we're parked on the side of the road and I was like, "Let's just get a new drone." But you're in Iceland, so can you get a new drone on time? I don't know. And so we were all walking around this field. We did end up finding it, but it was truly so random.

Jackson: (1:40:47) It's a normal day on the job.

Nan: (1:40:47) It's a normal day on the job.

Jackson: (1:40:51) Stripe Climate, exactly. We talked about this a little bit, but why do you think Patrick and Stripe care so much about funding things like this? Or Stripe Press or any—what about him? He's not unique, maybe, but he's certainly unusual for his peer set.

Nan: (1:41:08) Well, I'm not him, so I'm not in their brain and I can't actually speak to that. But my impression—I keep going back to how their souls are pointed in a good direction. They want the world to be better. And I think they have pretty expansive views of what that can mean. They're very long-termist and they have unusually high appetites for weird, riskier, off-the-beaten-path ideas. I think the combination of those traits is unusual. To the thing we were talking about earlier, I have not observed them to be ROI-obsessive in the works-in-progress, Stripe Press, Frontier side of the world. They're not asking questions like, "What's the brand benefit of this and can you quantify it?" They're a little bit more of this intuition and judgment and belief that ideas for progress—ideas are a way that we spread good things in the world. So, how do we distribute more great ideas?

Jackson: (1:42:28) Also probably a lot of trust in the people running these things.

Nan: (1:42:34) They also have that. I think that they care a lot about finding great people and then working with them for really long periods of time. That trust does compound over long periods of time.

Jackson: (1:42:44) Why do you love scones? Or maybe, do you love scones?

Nan: (1:42:48) The dirty little secret is that I don't actually love scones that much. Basically, I was on a trip maybe five years ago with a bunch of people, including my sister and my best friend Sarah—both of their names are Sarah. We were eating a really good scone and then we came up with the name Scone Heads. We were like, "We should start a scone rating account called Scone Heads." We just thought the pun was funny. And now five years later, we're still rocking. I would say that we need a bit of a brand refresh. I would say we've gotten a little lazy. But scone-heads.com—take a gander, see what you find on that website. I think it's a fun example of making stuff with friends. It has just been a silly side hustle with friends that has been a real treat.

Jackson: (1:43:46) You have a great little essay on relationship primitives. Speaking of making things with friends, have you updated your thinking or had any more creativity on the ways that sort of—one of the points you make there is that friendship is an especially underexplored category of ways that you can have unique relationships with people. And the things you can do with your friends, including the lack of commitments and all these other things. I think that was probably three or four years ago.

Nan: (1:44:17) Yeah, Bri and I wrote that together.

Jackson: (1:44:21) Oh, yeah. Right, right. Any updates? Any updated thinking?

Nan: (1:44:25) I mean, I still think that friendship kind of gets the dregs. We make things with coworkers, but we don't make them with our friends as much. Default together time. I feel like that actually crystallized for me when I did some work on my house a couple of years ago and I ended up moving in with some friends—with two friends and their three kids. They have three kids now; it was two at the time. We lived together for three months. I was friends with them before, but not super close with them, and it was just a really magical experience. How often do you get to live with friends as adults? We were always joking, like we’re meeting in the micro kitchen for a snack break or whatever, and it’s just real joy. The closeness that you get from that sort of spontaneous reaction is—you have that with a partner, you have that with family growing up, but it is hard to replicate with friends. This is why the Phil Levins of the world are like, "You should live near friends." That's the whole thing. It’s really amazing if you can do it, but it’s hard to execute in practice. We don’t go to therapy with friends. Not that one has to go to therapy at all, but it’s just interesting to me the things that we kind of maybe unconsciously bucket into certain types of relationships. We do this activity with this type of person, but not with this type of person. Why is that? I don’t think you have to do anything with anybody, but it’s more just... Yeah. Make a choice.

Jackson: (1:46:07) You were talking about the John and Paul book that Ian Leslie wrote, and you wrote that it's deeply romantic but not sexual. What does that mean? What do you mean by romantic specifically?

Nan: (1:46:17) This is a really...

Jackson: (1:46:18) What do you mean by romantic specifically?

Nan: (1:46:26) I think I mean by romantic that there is a romance to it. It’s like I can feel it, but I can’t put it into words. It’s like a soul conversation, or seeing each other deeply, or an appreciation for one’s being that feels more holy than just a friendship. But it’s not sexual. Reading that book made me feel like we are—I’m even struggling to find the words now—I think that’s because we’re impoverished for the language to describe these different kinds of friendship.

Jackson: (1:47:03) Do you think that’s specifically because it was a creative relationship?

Nan: (1:47:07) I suspect that had a lot to do with it. I think that melding of the minds and the melding of the artistic spirit... making something with anybody is an intimate act, right?

Jackson: (1:47:10) Yes, yes.

Nan: (1:47:22) And the most intimate version, I suppose, is the raising of children together. But creative projects, whether it’s art or music or getting a new thing off the ground with somebody like a co-founder—Sconeheads. I love this organic marketing for Sconeheads. That co-founder relationship is a marriage of sorts. I don’t think all of them trend into romantic territory, but creating something creates some conditions for that. Does that resonate?

Jackson: (1:48:05) It's funny, you were pointing to almost like a sacred element of it.

Nan: (1:48:08) Yeah.

Jackson: (1:48:10) I don’t know if it feels most resonant in the creative, because you hear Johnny Ive talk about Steve Jobs and it’s the same thing. You even somewhere reference all these creative duos. I do wonder if it’s possible without the creative part. It’s like, how many soulmates do you have? It’s like that.

Nan: (1:48:41) Yes. But if you specifically think about the creativity—if romance is conditioned on a creative endeavor—in what way is marriage a creative endeavor? Raising kids is. But I guess the creativity and the making things can take a lot of different forms.

Jackson: (1:49:04) I think part of it is obligation. One of the things about friendship that’s funny is there’s no technical obligations at all.

Nan: (1:49:07) Yeah.

Jackson: (1:49:13) You’re allowed to walk away at any time. That’s not quite the case with a creative partnership or with a marriage. But I ask about soulmates because I’ve had dinner party conversations about this. How many? I think some people would say, "Yeah, I have one soulmate and it's my wife," and then other people would be like, "I’ve had seven, and two of them were sexual." So there’s clearly—you’re pointing at something. A great old deep cut: the syllabi site. Do you have any requests for syllabi?

(1:49:39) Syllabi for the Squishy Topics & Study vs. Experience

Nan: (1:49:46) You know, I’ve kind of deprecated that project because I think that you can create great syllabi now for yourself with the LLMs.

Jackson: (1:49:55) I totally disagree.

Nan: (1:49:58) Okay. That was a good one.

Jackson: (1:50:03) Curation.

Nan: (1:50:06) Okay. What syllabi would you like if we revived the project?

Jackson: (1:50:30) I actually don’t think it’s the right answer based on what I was just saying. It’s like guides of cities and very specific cuts on somebody’s taste or the way that they experience a thing. But to the spirit of the original project, it’s about learning. This is a total cop-out, but if I had to learn anything, finding out that somebody I was friends with knew a ton about it and was going to...

Nan: (1:50:54) Guide you through it.

Jackson: (1:50:55) Not even if they were going to tutor me. Like, even if they were just like, "Here, I’ll put together..." It’s very similar to, "I’m going to Tokyo." I can go look up the average top takes, or I can get a specific friend’s list. And maybe if I’m lucky, they might even add in a few tweaks for me. I just think, what a beautiful way to learn.

Nan: (1:50:58) Yeah. Does it matter to you that you know the person or just that you respect their taste?

Jackson: (1:51:24) I think it’s more... especially if it’s about learning, I actually don’t think it matters quite as much that I know the person. That’s an extra nice thing. But I want—it’s the same reason having a great professor or a great reading list is much more...

Nan: (1:51:27) Yeah. Yeah.

Jackson: (1:51:38) A reading list is way more interesting than the list of the "best books."

Nan: (1:51:42) How much do you think, though, that... because one of the things if you're snapping to a person who's curating the syllabus is they might have slightly different interests than yours. So—

Jackson: (1:51:55) But it's a syllabus, to use your definition. It's like, "How should I spend the first five hours learning about this topic?"

Nan: (1:51:58) Yeah.

Jackson: (1:52:01) The goal would be that I get deeper into the pool and then I can swim for myself.

Nan: (1:52:05) Yeah, but the introduction to the topic.

Jackson: (1:52:07) Right. And it's like, I'm in good hands here.

Nan: (1:52:10) Yeah.

Jackson: (1:52:12) I know that Devon—or whoever's going to—is going to give me a... I know I'm... it actually hilariously goes back to what we were talking about earlier in the conversation, which is that when you don't know anything about something, you don't know where to start.

Nan: (1:52:21) Yeah, yeah, yeah.

Jackson: (1:52:22) And so it's like a helping hand that says—

Nan: (1:52:24) Okay, here's the map of the territory. Drop in. Drop in.

Jackson: (1:52:27) You want the AI version of that. And if it's AI, I want it to be a specific AI. I want it to be... maybe Claude's going to have a strong point of view. I don't know.

Nan: (1:52:36) Okay, so the original prompt for that—the original thing I wanted to do with syllabi before it became the current version of it—was the thinking that there's a category of topics that are really important and consequential to how we live our lives. Friendship, partnership, conversation—squishier things like that that we don't really study. If you think about how you learn a topic, you can study it or you can experience it. In academic topics, I think we probably tend to overstudy and underexperience. And in life topics, we probably overexperience and understudy. And so what I originally wanted to do was like, "Okay, I want the syllabus on friendship. I want the syllabus on XYZ." But finding a person to write that syllabus is really hard and I couldn't crack it. So I pivoted to something easier.

Jackson: (1:53:28) One of my favorite things I found in this prep is "Art is for Seeing Evil."

Nan: (1:53:35) So good. You read it?

Jackson: (1:53:37) I read it. I read it in bed last night. It blew my mind. It's really like... if I could recommend... oh my gosh. And ironically, the start of that piece, she's like, "I'm teaching a class on death and this is part of the syllabus."

Nan: (1:53:51) Yeah, I know. We should just reach out to her and get her a syllabi for that stuff.

Jackson: (1:53:55) That would be cool. Oh my gosh, that piece is incredible.

Nan: (1:53:58) It's such a good piece. She was actually going to—I read somewhere, maybe I'm making this up, but I think she was going to do a class on partnership or marriage or something like that.

Jackson: (1:54:09) She referenced that in this piece.

Nan: (1:54:10) Okay, that was in this piece. And I'm like, what a take! It would be so interested because I think another piece about the squishier life topics is that we look at friendship or marriage or raising kids from the lens of our geography and the time that we're growing up in. We're sort of space and time constrained. Whereas it might be helpful to sort of think about, how has marriage evolved over time? How has child-rearing evolved over time? Giving us ideas of like, "Oh, it wasn't always this way," or "That's not the only way to do it," or "In Japan they do it differently." And not to say that one... in my head, it's sort of a hack for how do you get out of the default snap-to-grid.

Jackson: (1:55:00) My sense is the biggest reason that's not really the case is there are a set of things where you don't want to trust general wisdom at all. I don't know, aspects of science, where things are changing. But on the list of things you just described, on a relative basis, you want to trust your grandma about marriage or whatever. It's not changing that much. But because of that, we sort of default to the, "You should never fully even inspect this thing."

Nan: (1:55:03) Yeah.

Jackson: (1:55:32) And you should just learn it passively—like, you shouldn't learn it actively.

Nan: (1:55:36) Right. I think it's the passive-active thing that feels odd to me. Whereas we're so open-minded and active in other parts, in the less emotional domains, and then in the emotional domains we don't study it in the same way. Is there something to... I read this anthology a couple of years ago called Wing to Wing, Oar to Oar, and it's basically a syllabus. It's an anthology that Leon Kass and his wife put together about marriage. It's excerpts from the Bible, it's excerpts from the Greeks, it's excerpts from Shakespeare and literature and Darwin and philosophers. It was sort of the closest thing that I found—it's fat, it's a tome. I didn't read the whole thing, but I poked around. But it was sort of the closest thing that I found to a course catalog on a big squishy topic like that. And I'm eager to read more of those.

Jackson: (1:56:49) Maybe we're afraid of, "How dare you claim to have some objective view on marriage?" So you're not allowed to write a syllabus on it. But this goes back to: I don't want the objective syllabus.

Nan: (1:56:52) Totally.

Jackson: (1:56:57) I want somebody's perspective.

(1:57:01) Inputs & Outputs and GLPs for Attention

Nan: (1:56:58) Totally, totally, totally.

Jackson: (1:57:01) It's 4:10.

Nan: (1:57:02) Okay.

Jackson: (1:57:02) I know, you're good at this. There was this "Words that Matter" recommendation thing you did. Pulling from that on a few points... I don't know how to pronounce his last name, but you were talking about Ted Gioia. And he was making a point about inputs creatively, primarily. My sense is you're someone who's fairly consistent. Are there any critical inputs that have been very consistent for you?

Nan: (1:57:28) I actually think this is not an area of consistency for me. And this is a muscle that I'm actively trying to build. I'm going to dodge the question, which is to say I am trying to make the input piece a better habit for myself. One of my problems is that when I get obsessed with something, my blinders are on. I'm just like, "Every incremental moment should go towards that thing." And I kind of starve other areas of my life. So I go through kind of spurts, where I do a lot of my reading, for example, on vacations and over breaks and in transit. I would like to change that. That is—

Jackson: (1:58:12) You think we can change these things about ourselves?

Nan: (1:58:15) Yeah.

Jackson: (1:58:15) You do?

Nan: (1:58:15) Yeah, I think I've gotten better at it for sure. I think it's a muscle.

Jackson: (1:58:19) I wonder if I'm ever going to be someone who can do things with incredible earnest long before they're due.

Nan: (1:58:26) I bet you could.

Jackson: (1:58:27) I've been trying for a while. I don't know.

Nan: (1:58:30) Okay, interesting.

Jackson: (1:58:30) And so sometimes I wonder, should I just accept it? Part of the point is, especially on inputs—it goes back to my marathon thing. Every year I’m like, "I’m going to try to run a little bit more." I guess there’s some aspect of running that’s autotelic. I like to run. And then I decided I was going to run in a marathon and my level of seriousness about running totally changed. Having a great output goal was really critical. So, I don't know. I would love to become this idealized version of myself that has all the best inputs, but—

Nan: (1:59:11) Well, I feel like in that example, your hack is just that the trick to getting you to do better input is just framing it as— So you need maybe more like mini-marathons or something.

Jackson: (1:59:24) Reading inputs is almost like a practice. Well, yeah, specifically, I don’t need to care about the output.

Nan: (1:59:37) I think that’s—yes. And I don’t know, maybe your output is like the good example you gave earlier. You were like, "I'm going to do 21 podcasts this year." Okay, or "I'm going to read for an hour a day for three weeks" or something like that. I think there’s maybe a way you can gamify the inputs or something, if one must.

Jackson: (1:59:51) Yeah, this romantic idea of the person who's just all inputs and trusting themselves and it's all intuition.

Nan: (1:59:58) And I think it’s the kind of thing though that, for me, once the muscle has atrophied, the startup costs are hard and you’re like, "Gosh, this is not fun." But then when you trust yourself, it feels more fun again. I feel like there are periods—and I hate to admit it—but there are periods where I’m not reading that much and reading feels like I want to check my phone, I want to do other things. I’m like, "Ugh, I’m never going to get this back." But then if you just force yourself...

Jackson: (2:00:27) Fake it till you make it.

Nan: (2:00:27) Fake it till you make it. Yeah, there’s real truth to that.

Jackson: (2:00:32) A great line from one of your blog posts: "We've all lost days to ennui. So did Mark Twain. What Mark Twain never lost was a day to YouTube shorts." "GLPs for Attention" is where that post comes from. Maybe it's kind of like the input thing. But reading that post, I talked with a bunch of people about this idea—like Ozempic for TikTok. Could it really work? And similarly, it’s like, is it cheating? Does it matter? This is the question. I really don’t know. There are certain things where I’m like, if I have to force it, am I—if you need Adderall to do your job, to really be focused on your job... and I don’t know, maybe the wrong example and too loaded of a question. But if you really need to—one of the things I always joke is I don’t really totally believe in willpower. If you really have to grit and bear it, you might be doing the wrong thing. And yet, I love the metaphor of dieting. If I really just was hedonistic, I would eat candy all day, and I don’t eat candy all day. Or I don’t drink alcohol all the time. But for some reason, with attention, I worry about this so much. I think about a thing that would be like, we solve all our problems and we live in this abundant world and we sit on algorithmic Vision Pros...

Nan: (2:02:04) What feels icky to you? Do you feel that way about GLPs themselves? Do you feel that there's a cheating thing there?

Jackson: (2:02:20) No, but I don't struggle with overeating, so it’s a little bit hard for me to know.

Nan: (2:02:23) But do you feel that way when other people take them?

Jackson: (2:02:31) Yeah, it sort of feels like I'm giving up the game to algo-capitalism and I’m not strong enough. Maybe that's just—I don't know. I don’t feel that way about caffeine, but I suspect if you ask people about this: "I’m going to give you a drug that just allows you to focus on whatever you want to focus on." Maybe this is a very silly thing I’ll look back on in 20 years and be like, "Oh my gosh, I was just playing on hard mode." It's kind of like playing on hard mode.

Nan: (2:02:34) Yeah.

Jackson: (2:02:37) Okay. Maybe I have a thing where there’s no free lunch in the universe and it’s just all trade-offs.

Nan: (2:03:03) Yeah.

Jackson: (2:03:06) There’s a downside of caffeine and I take it anyway.

Nan: (2:03:11) Okay, well, I think one would need to weigh the downsides of GLPs in their context. But in this case, for this hypothetical drug that does not exist—"GLPs for attention"—if it did exist, do the benefits outweigh the costs? If that lets you focus on the things that you want to, rather than scrolling Instagram or TikTok all day, and get good things done for the world and do things that are meaningful to you, and it makes that easier...

Jackson: (2:03:52) It’s like a Luddite-style "natural" thing. Like, it’s not natural.

Nan: (2:03:55) Yeah, no, I know. And I think we all have little glimpses of that. It’s a good thing to interrogate where that comes from. There is something in struggle generally. We get something out of struggle; it builds character. And when is struggle good and when is struggle bad? I think that that’s an important question. But I guess in this case, for many people, is this struggle of spending all of your time trying to not think about food really yielding that much benefit? I don't know.

(2:04:38) Closing: Interviewing Parents and Imagining an Obituary

Jackson: (2:04:39) Totally a different topic, but what did you learn from interviewing your dad?

Nan: (2:04:46) Okay, well, the context is that I was up with my dad in our cottage in Canada one year. It was just the two of us. We go there every summer and I basically decided to turn a bunch of our conversations into podcasts. I would just throw down the phone, pick a couple different topics, and ask him questions about a certain period of his life or music—big classical music guy—or relationships, et cetera. I think that one of the things—and this is going back to the relationship primitives thing—is if you approached your family member the way that you would approach a work interview, with the same intentionality of approaching a conversation that you would prepare for, there’s a lot of insight in those family members of ours. There are a lot of experiences that you don’t know about because you haven’t interrogated them intentionally in those ways. That is the thing that I walked away from, sort of being like, there are these treasure troves of cool stories and history all around us. I think borrowing a lens from the workplace and applying it to your family member or your spouse is a neat mix and match.

Jackson: (2:05:56) Yes. There's some implicit thing where you're not supposed to think about it that much.

Nan: (2:06:01) Yeah, right. Or it's just supposed to be free-flowing.

Jackson: (2:06:03) Right. This goes back to the point you were making about the syllabus for some of these softer topics, too. It's like these things, you're just—

Nan: (2:06:09) Right. These ones are supposed to just come naturally, and you're just supposed to feel them out. I think that that's fine also—that's great. People should shoot the shit with their friends, and that's awesome. Sometimes if you haven't seen a friend in a long time, you might throw together a quick little agenda in your head, like, "I really want to understand how they are doing on this thing" or "What's going on in this part of their lives?" Again, it doesn't have to be 100% of the time, but I think infusing 10% more of that intentionality into the relationship—yeah, that's what it is. It's quite interesting.

Jackson: (2:06:46) It's funny. It's very SF and—to use even stronger language—very autistic to say the quiet part out loud. It's delicate, and you can definitely go too far. But sometimes San Francisco culturally can be kind of charming in that people will say the quiet part out loud, see the water on the intentionality part, and play with it a little bit in ways that can be really great and lovely. I think there can be other times where you're like, "You don't need to say this part out loud." So it's challenging, but okay. Just a couple more things I like to ask people. That's a good one. My last thing: you referenced this amazing little obituary on your grandmother, Regine Weiss Ransohoff, the "Lives They Lived" piece. Your aunt had written it. You say you can feel how fierce, principled, irreverent, brilliant, and witty she was, even in just a few short paragraphs. It makes me wonder what my hypothetical daughter would write about me. What would you hope that hypothetical daughter would write?

Nan: (2:07:44) If I get an obituary that is similar to my grandmother's, I'll be a happy camper. I did an exercise like this about five years ago when I was trying to figure out which way was up: kind of sketch out an obituary of yourself and use that as a guide to see if you are roughly headed in the right direction. I don't know exactly, but a couple of things that I hope will be in there or that I aspire towards are doing good things for the world and trying to use what I have to make the world better in some capacity. Another big one is helping the people I care about in my life become the best versions of themselves. I think the people who have held up versions of me and helped me see those when I wasn't able to see them have been really—well, you know. There are all these studies that show kids who are told they're great at something early on end up being great at that. Whether or not they have that innate ability, it's easier to believe in that when someone else is helping you hold that for yourself. I don't always hit the mark on that, but that is something that I aspire towards for myself and for the people around me. Then there's the zag piece: that I made my own decisions. If you don't like them, "make your own art" kind of thing. I want to do things the way that feels right and aligned with myself. And then, have fun doing it. I think the fun piece is an important thing to lean into. We're not here for that long—maybe we will be in the future. Maybe we'll be here forever! But in the meantime, I want more fun.

Jackson: (2:09:45) If that's the case, the advance market commitment bounty for living forever will probably be pretty—

Nan: (2:09:48) Yeah, I know. I think somebody's working on that. People are on that. But something about just enjoying it as it happens. Thanks so much. It was a really fun conversation.

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