How to be Agentic in the Age of AI (Cate Hall, CEO of Astera)

In 2016, you were the world's best female poker player. I played exclusively live poker. I was really focused on the aspects of the game that are about body language, demeanor. You have a lot of time at the table where you're just observing what people are doing in hands. And it was kind of this fertile ground for evidence collection and study. Can you really be ambitious without being agentic? Is that really possible? Ambition and agency can be almost totally decoupled. Like you can have somebody who's highly ambitious, but not agentic. You can have somebody who's highly agentic, but not ambitious, which you get conflated a lot. How did AI risk start to become something that you were concerned enough about that you really wanted to devote your time on? A lot of the things that provide meaning to human lives are slowly coming apart at the seams because of the way that humans interact with recommendation algorithms. all of the frictions of life still they get eroded away in a way that just leaves us with this heavily dopamine-steered kind of smooth tunnel of an existence. What are useful questions for us to ask ourselves? How do we start to surface useful information? It is the most challenging problem that humanity is currently facing, and it feels actually overwhelming to me, and I don't understand how we are going to make it through. Hey, I'm Mario, and this is The Generalist Podcast. As the saying goes, the future is already here. It's just not evenly distributed. Each week, I sit down with the founders, investors, and visionaries who are living in the future to help you see what's coming next and understand it more clearly. Today, I'm speaking with Kate Hall, the CEO of Astera, an institute focused on AI risk and frontier technology. In the years before Astera, Kate was a successful lawyer, biotech executive, and a professional poker player, eventually becoming the world's top-ranked female player in 2016. In our conversation, we explore how Kate's contrarian focus on live reading allowed her to succeed at the card table, how people play at being high or low status in conversation, and what that tells you about them, why the biggest AI risk might not be alignment, but rather a soft takeover where humans gradually lose independence,

and why Kate believes agency is a learnable skill rather than an innate trait. I walked away from this conversation with greater appreciation for the authorship we all have over our own lives and the practical techniques anyone can incorporate to increase their sense of agency in an increasingly automated world. If you liked today's discussion, I hope you'll consider subscribing and joining us for some of the incredible episodes we have coming up. Now, here's my conversation with Kate Hall. This episode is brought to you by Auth0. Auth0 is an easy to implement, adaptable authentication and authorization platform. Think easy user logins, social sign-on, MFA, and robust role-based access control. With over 30 SDKs and quick starts, Auth0 scales with your product at every stage. Auth0 lets you implement secure authentication and authorization for your preferred development environment. You can use all your favorite tools and frameworks to manage user logins, roles, and permissions. Auth0's new offering, Auth4GenAI, is currently available for developer preview. Secure your AI agents and integrate with the GenAI ecosystem using features like user authentication, token vault, which calls third-party APIs on a user's behalf, async authorization, and fine-grain authorization for RAG. What typically takes 50-plus lines of code is reduced to just a few. Kate, I think you might have one of the most interesting backgrounds of anyone I've had on the show so far. And that is a... a tough standard to beat because there have been some really fascinating people, but a really eclectic background that has led you to your current role as CEO of Astera. And maybe we can almost work backwards. Can you tell us a little bit about what Astera does and what your role is? Yeah, Astera is a private foundation. It was started a few years ago by Jed McCaleb. And we are focused on providing

a model for philanthropic support of emerging technologies. So we are very focused on deep tech, very early stage technology, and focused on a more investing heavy approach to philanthropy than most foundations. Those are some of the sort of differentiating factors. Amazing. I'm sure we'll get into more of that. But I've been super interested in what you guys seem to be building and feels like a really ambitious approach in sort of like the nexus of philanthropy and frontier technology, which is not something you tend to see mashed up that often. So, yeah, excited to get into that. But I'd love to go back in time a little bit to the fact that in 2016, you were the world's best female poker player. Is that am I remembering the dates right there? Top ranked, yes. The reason I have a persistent internal conflict about whether it is fair to characterize myself as the actual best when poker is such a high variance endeavor. But I was the top ranked female poker player in the world. Got you. So by whatever measure people could do that, that made sense. One of the things that I think I saw you talk about this maybe on another podcast or. you've written about it, I believe also, is that the approach you had to poker was so, so interesting to me, which is that you like really focused on social reads for the folks who maybe do not play poker. Like, what does that mean? I played exclusively live poker, which is somewhat unusual for pros, less unusual for pros who live in the US. But I was really focused on the aspects of the game that are about like body language, demeanor, the things that aren't just the size of your bets and perhaps the timing of your bets. So there's a large part of modern poker is having a really deep, detailed understanding of game theory and the math of the game. And that's sort of like table stakes, so to speak. And then there's this other part of poker, which was actually really popular, I think.

20 years ago, still sort of popular in the popular imagination, which is live reads, like the kind of thing that you see when you watch Rounders and you see Teddy KGB with the Oreo, you know, that kind of stuff. It's the idea of there are these sort of tells that you could figure out. Had you always been someone that you were like very good at reading people and you had sort of an intuitive sense for this? So I think that this actually comes from. like compensation for a bit of autism that I have so I think that that when I was growing up I was actually miserable at reading people and was never able to figure out what people were thinking and so I you know I was quite smart at the same time and so like applied my intelligence to this sort of like systematic attempt to understand what people meant by the things that they weren't necessarily saying outright and so I got really obsessive about understanding people's body language and it became an object of fascination for me. This really took off when I started playing poker full time. And I, you know, you sit there a lot in poker. You have a lot of time at the table where you're just observing what people are doing in hands. And it was kind of this fertile ground for evidence collection and study. And I became really obsessive about it. The autism element doesn't surprise me at all. It's funny, the person who I know who is sort of the best reader of people would say the exact same thing, that it was because of sort of needing to compensate growing up with maybe a sense of a deficit in that, that they became so immaculate at it. And now they're an extremely good investor, which is something I wonder to what extent you sort of use these skills in your day-to-day life, you know, your spotting talent. philanthropically, research wise, you know, with this investing side, do you end up like trying to read people in that way? It's a really interesting question. It's something that I've never really thought about before. So I have this sense and perhaps lots of people have this sense that it's just not true that I have a good eye for talent. And I have a hard time breaking down exactly what I attribute that to in terms of like, what are the things that I'm seeing in people? I do think that there's like a certain quality of

switched on-ness that is hard to fake and that correlates highly with being capable of doing extraordinary work. And so I found it to be the case that I can tell within 10 minutes of meeting somebody whether they would be a good addition to a team. I'll then go and do a bunch of other stuff to verify that. But I found my... My instincts, at least, often correspond to my final determination for Balor Wars. I'm curious, like, so when you say this about your friend, do you have a good sense of what it is that they are looking for in their interactions that's giving them that signal? They're still never. perfectly precise ways to talk about this, but the firm I'm talking about that really is, I think, quite masterful at this is Hummingbird Ventures. They're now a firm that I work at as a venture partner also, but the founders of that firm, I became obsessed with their approach to VC because it's super psychological. And they, I think, had some of the most precision around the traits they look for. And so they have different terminology internally, but things like clock speed of someone like really seeing just you know almost what you're talking about like seeing that level of of quick processing ability to talk through these things um you know this is maybe a bit of a cliche phrase but i i think the way that they analyze it is very uh interesting is like signal to noise like how much of someone's conversation you can really almost sense like the weight of someone's individual words in a conversation if someone seems to almost every three words or four words say something extremely interesting or extremely surprising uh that tends to be something that's really unusual um and then you know they've talked a lot before and and peter teal has written about this obviously in zero to one about sort of certain types of neurodivergence including autism occasionally correlating really nicely with like these very unreasonable style of people who don't care about what others think of of certain parts of their behavior that can you know maybe is not a good profile for a team player but can be a really good profile for a founder totally I think there's

There's multiple components of that. That makes sense to me. So there's a part of the switched onness characterization that is just like raw G. It's just like the person is very smart. They're able to adapt really quickly in conversation. That's like one sort of baseline criterion. I think there's then... You could call it like first principles thinking. You call it disagreeableness, like different different ways of describing it. But there's like a way in which the person is deliberately not trying to figure out exactly what you want them to say. And then saying that like a refusal to play guess the password is also a really important thing. And then I think there's also a third thing, which is like psychological health, which can be tricky to assess. But I think. One thing that you often see is people who are willing to be sort of fluid with status in conversation. So people who are comfortable, who have like the kind of confidence that allows them to be self-deprecating, to like sort of like play with the structure of conversation, even as they're having it. I feel like that is generally a sign of psychological health that bodes well for how I will interact with that person and also like whether they will be a good cultural fit. for working with me because I care so much about candor and communication and directness and people who these are like overlapping sets of abilities, basically. Really interesting. I wasn't expecting to go in this direction, but what you said there about sort of playing with status in a conversation made me wonder if you've ever read the book Impro. Yeah. Yeah. Yes. Oh, wow. OK, great. That was that was a that really hit the target. Yeah. So for folks who haven't read it, I was I was introduced to this book because it was on Palantir's like internal reading list. I saw that. Yeah. Which is so I was like, how on earth does this book that's theoretically about sort of acting and improvisation end up on. at this defense company's reading list. So I was like, I have to find a copy of this and read it. And I found it so interesting. I don't know what you thought of it. Yeah, it's totally fascinating. For people who haven't read it, it's sort of like an improv teacher's breakdown of the ways that people communicate status in scenes, basically, which involves also a diagnosis of what are the indicia of...

comfort or discomfort, high status and low status and conversation. And once you've read this book, I feel like it just has it's one of those books where it colors your interpretation of so many interactions because you see what people are doing without even necessarily intending to in order to like elevate or lower their status and conversation in order to like get what they want out of conversation. And it's really, really interesting. And I found that like. People who are always trying to play a high status in conversations, who are concerned about maintaining sort of the appearance of being the high status person in a conversation, that to me is a sign of psychological like poor health. That means that they will generally not be like an enjoyable person to work with. It can be like. a good marker for dark triad traits. It's like people who have an unhealthy level of concern about the way that they are viewed. Yeah. Yeah. Yeah. Yeah. That's interesting. Yeah. There's sort of a brittleness around the ego there that like you could imagine picking up on. That's that's really intriguing. Yeah. The the high status, low status thing and being able to play with that is something is maybe the thing I took most from improv as well, which is like the teacher talks about how when he has students in his classroom, he's sort of always playing with that boundary where he tries to to start very, very low status and, you know, doing things like sitting on the ground and, you know, explaining that if if anyone doesn't. know what to do. It's really his fault and they should blame him. And there's all these little ways of really changing the energy in a room with someone that makes sense why, you know, a company like Palantir might actually find that useful. Yeah. Yeah, totally. And I think it can also be when you get better at thinking in those terms, it can also be a great mechanism for increasing psychological safety in an organization. It's like a little bit in the weeds, but I think that

Having leaders who are not interested in maintaining the illusion of high status is one of the things that allows an organization to be sort of like healthy at an organization level, allows people to grow quickly in their knowledge and their roles. There's just like less obsession with how people compare to other people within the organization. It's like a little bit of a subtle point. But I think that like this kind of. Fluidity with status is probably a signal of healthy workplace cultures as well. Here's a quirk that I can't figure out as we talk about this. It strikes me that many of the best tech-style founders that we can think of don't seem to play low status often, and yet they're very effective. I wonder why that is. Is it not necessary in some context? When I think about examples, like perhaps this is not actually an important quality in founders. It is more of an important quality in executives. And so like the professional executives that come in and take over Microsoft or Google, maybe this is like an important thing for them to have. Whereas being like the charismatic solo or like. core founder of a tech company, this is less important. I think there are interesting parallels between poker and startup world in general. And one of them is the fact that maybe starting 20 years ago, in both cases, there was this new wave of charismatic driven people who are very young, who came in and had like a new way of doing things. It's like the Y Combinator. you know, crew in the startup world. It's like the, the German new wave people in poker. And these people, I think in both cases had such a compelling new way of doing things that they didn't need to like optimize in other dimensions the way that you need to once a like niche has already been explored and the low hanging fruit has been picked. So it's like,

When a whole domain shifts into a new paradigm, you can get away with being really lopsided and being like actually weaker in certain ways than you can once a field matures and you have to be sort of balanced and good in a wide variety of domains. It's just a matter of there being such large gains available from changes in strategy early on that it like dominates over the effect of being. weaker in other areas so i think it's really interesting because you can get like people will draw from that conclusions about the characteristics of a good poker player or the characteristics of a good founder where i think those can be misleading and it can actually be a case of people succeeding despite their limitations or despite their flaws rather than there being like a correlation between them this is maybe i'll just cope because my theory doesn't work actually but it feels it feels like this could be true um where like the the characteristics of a good early founder are just different i think that's really interesting i think i definitely agree with the idea that uh some of that sort of comfort on the ego side maybe actually goes against the type of founder that we've seen. But I also totally buy that, you know, the meta can change across different environments. And maybe, you know, the sort of Zuck style leader works for another 10 years or, you know, maybe it changes and towards something different. I know nothing about this, but I just want to flesh the analogy out more. And also I'm curious, what was like the German wave in poker? Like what was the sort of meta that emerged there that, you know, you had these young wunderkinds emerging? I think that like early poker, by which I mean everything up until 2006 to 2010, was really a lot of vibes based play. Like live reads were a part of that, but also just like people were. were able to go on intuition a lot because there was so much money in the game relative to the average skill level of players. And poker had this explosive growth in the back half of the aughts following Chris Moneymaker.

This accountant from North Carolina or something won the World Series of Poker, won 10 millions of dollars. And so there's this huge influx of money and players into poker. And this kind of like brought in the sharks who might have otherwise been doing financial analysis or something. I don't know what they would have been doing. But there was enough money in it to bring in a whole new category of really smart, driven people who are just trying to figure out, who are basically like trying to solve the game. Poker is essentially an unsolvable game, but what you see is over the course of the last 20 years, people working out to a greater and greater level of granularity what game theory optimal play looks like and sort of converging on something that looks like game theory optimal play. And the tools over time have improved for that. So simulation tools are a really big part of poker now and have been for the last 10 years. But there's this deep... mathematical game theoretic rigor in poker starting around um like 2010 to 2015 that really wasn't there before that wow really interesting um and so in that respect your sort of return to live reading was was quite contrarian i imagine it was yeah yeah um and it was it was kind of like a bet um on something like what i was just describing which is like it's a bet that people, because they have grasped this new way of doing things that has huge returns, this like math-based way of doing things, that they are going to overexploit that and then like forget to develop other skills, basically, that are also quite valuable, but that they've learned to disregard as less important. I was reasonably good at the math side of the game. I was not... exceptional by any means. But by focusing really hard on this one aspect of the game that other people were just not thinking about at all, I think I was able to have much better results from like the combination of those things. Did you find you were particularly good at reading like, I don't know, a certain type of person or a certain type of movement? I don't know. It could be hands being really illustrating her eyes or whatever it might be. I think.

Anything where people are choosing to give information. So there's like a lot of people will simply not try to draw a lot of attention to themselves and will try to sort of act the same way in no matter the situation. And. There's a lot of stuff that works on those types of players. And there's kind of level two players who know a little bit about live reads and are maybe trying to give you false information or something like that. And I loved playing against those players because not only were they pretty easy to figure out if you had a little bit of data, they're also incredibly easy to manipulate into doing really stupid things. People who don't know anything about live reads. are much less likely to do something that is wildly, like, kind of laughable from the perspective of other people as compared to somebody who you have convinced has a live read on you that they don't actually have. And so the most fun moments, I think, in poker were sort of tricking somebody into doing something that was really ridiculous. I love that. Yeah. The person who thinks they're a decent player is willing to try and sort of like enter this gambit with you and start signaling things more visibly or aggressively that then you can sort of, you know, easily detect versus total amateur. You know, they don't they don't really know what they're doing at all. So they're not really giving off that many clues. That's me. I'm the total amateur. And as a result, I lose all the time. But every once in a while, something goes my way because I think I'm just maybe unpredictable enough. harder to play against total amateurs than it is against people who are like, OK, OK. That's good because I don't seem to get any better ever. So I remain at that level. I do want to talk about some of these tech things, but we're actually sort of ending up, I think, talking about them in really interesting ways. I want to take another step back in your history, though, because it's another fascinating chapter, which is that you were a very successful lawyer for a period of time. You know, went to Yale Law School, argued in front of the Supreme Court.

Didn't argue. No, OK. No, no. I wrote the briefs in the Supreme Court. There's like the way Supreme Court argument works is there are like [redacted address] cases. And you have somebody who is like comes in specially to do that for the oral argument. So I've never argued in front of the Supreme Court. I have appeared in the Supreme Court. I have written the briefs in the Supreme Court. I should know that. Important distinction. I should understand that distinction. Yes. How did you sort of wind up in that world? Because it sounds like you have a very unusual brain. Obviously, there are lots of interesting and intelligent and creative lawyers. But I would say that by and large, from my first experience out of college working at a law firm, and thus a lot of my post-college friends becoming lawyers, they don't tend to be the most generative people. I think I found a lot of the exceptions, but still, it's slim often. I think that's fair. Law is attractive to people who are like ambitious without being agentic is one way of framing it. Where it is a really clear career path where if you are smart and have like the right aptitudes, you can rest assured that you will make a bunch of money doing it. Super low risk. I think that it just for a variety of like biographical reasons. Until I was already a lawyer in my late 20s, I had a very low degree of introspection about my life choices. So I just kind of like got on this path because I was good at it and because people kept giving me more and more money to do it. And until I was like... 29, I didn't start thinking, why am I doing this? I don't enjoy it. I don't know anybody who enjoys it. Wouldn't it be better to do something else with my life? Even if that means I'll make less money, I'll be less successful. And it's really weird to look back on and realize how little introspection I did about those questions. But it just, for whatever reason, that was the case. I really like that distinction between ambition.

And being agentic. And we should talk more about being high agency in a moment. But can you really be ambitious without being agentic? Like, is that really possible? I think it's totally possible. So I think it's interesting. People seem to conflate these ideas a lot. And I understand it. I understand it, especially in like tech world, because the two often look so similar. There is an aspect of being an outlier. a success outlier in tech that requires a level of differentiation from your background and like iconoclasm maybe, which is just not the case for success in a wide variety of other fields. Like to be a successful lawyer or investment banker, I think I've never been an investment banker, maybe an accountant, things like this. You can be... highly ambitious. You can be really driven to be the best in the thing that you are doing. At the same time, it is a career path that requires very little creativity, very little like questioning. And you can almost do it on autopilot. And I think that that is the case for a lot of lawyers. It's funny, like Yale has this reputation of producing a lot of people who don't actually want. like don't remain lawyers for a long time. And I think that some of it at least is attributable to this phenomenon where people go to law school. They go to law school maybe because they get into the best law school and they're like, well, why wouldn't I? And then they go, they make some money and then they realize, oh, I don't actually enjoy doing this. Why am I doing it? Yes. And so. I think ambition and agency can be almost totally decoupled. You can have somebody who's highly ambitious, but not agentic. You can have somebody who's highly agentic, but not ambitious, who just directs their agency at wanting to have a great home life, a great fulfilling personal life. And so the two get conflated a lot, but I think that's almost just like an accident of the tech industry in which we tend to talk about them.

Yeah, you've totally convinced me, actually. I really didn't see the total decoupling there, but I think that exactly makes sense. That's totally right. How did you just suddenly discover all of this agency you had to leave law and play poker? Because that, I imagine, was on no one's bingo card. Yeah, so I think LSD had a lot to do with it for me. I think that there are different... there are different triggers that people can have for these kinds of like agentic awakenings. And I've, I've gotten really interested in thinking about all the different ways that this can happen. But for me, the first thing was definitely experiencing LSD for the first couple of times. And I think that just let me step back and view my life more objectively and realize this isn't necessarily a good way to be living. Like the trade-offs that I'm making here don't make sense. And I'm not. actually directly thinking about them because I know that doing that might cause me to have to do things that are like painful or uncomfortable. So I've been avoiding it. And that was, that was. Very disruptive, also great for me. The fact that I ended up playing poker was, I think it was more me running away from law than running toward poker necessarily. I was just like, I developed this really strong aversion to what I was doing once I saw the real state of my life. And I just felt like I needed to escape it as soon as possible. Poker was something that I'd recently gotten interested in. I'd been playing casually for maybe a year or so before this. And I was like, I could probably do this for a little bit. Worst thing, I burned through some of my savings. I find something else to do. It's not the end of the world. And I just kind of ended up actually falling in love with poker for several years. But it was more of a get me out of here. I have to get away from law kind of thing. It's interesting because it's both sort of like.

totally the opposite direction of law, but also it has some of these characteristics, right, which is like so highly competitive. It is very zero sum. I imagine, you know, the benefits of studying, I'm sure, helped you in some respect and having like a rigorous mind. Did you fall out of love with poker at some point? Like, do you play now for pleasure ever? Or is it sort of like, ah, you know, that that actually doesn't interest me at all. That's an interesting question. So I stopped playing poker because I had a very. serious mental health issue that came on pretty suddenly and that tied into drug addiction, which was a problem for me for several years. So I have like a pretty abrupt end to poker where I was just like it. doesn't make sense for me to play anymore, given everything else that's going on in my life. And then since that has resolved, which was like five years ago now, I have occasionally flirted the idea of playing poker more. But it's a little bit, it's one of those things where... when you used to be really good at something and then you go back to it. It's like picking up an instrument again after a long time, you know, where you're like, oh man, I sound so much worse than I used to. I think it is possible to enjoy poker and I'll play games with friends sometimes, but actually playing in a serious tournament or playing in a serious game, it feels a little bit... unsatisfying to me because I'm just so aware of the fact that I'm not as good as I used to be in an absolute sense I'm definitely not as good as I used to be in a relative sense because the average skill level of players has continued to rise in the like eight years that I've been gone now so it's not it's not that fun I do miss it a little bit but I also really like my life now. And poker is really time consuming. Yes. It's like to get to the stage where you'd be kind of happy with how you're performing would take would take quite a lot. Has live reading like had any sort of renaissance? Like now would you have to compete against people who, you know, are picking up on every eye twitch and, you know, little shibboleth here and there? I'm not sure of the extent to which this is true. So one of the I had like a couple people that I.

studied a lot with who were as into this subject as I was when I was playing. And one of them was Charlie Carroll, who was a well-known British poker player. I saw this TV show that Charlie was on. He was on a poker competition show a couple of years ago called Game of Gold. And I saw people analyzing his play in that game where they were like, oh, he's got... the live reads and it was sort of like like people could really tell that it was a thing and they were like scared of it um but at the same time i didn't get the sense that there were a bunch of other people who were dedicating themselves to figuring out rigorously like how he was doing what he was doing so it seems to be a little bit less like People accept that there is a there there more, perhaps, but I don't have a window on how common it is for people to then actually devote time to getting good at it. Maybe it's really common now. It'd be interesting to know, actually. It would be really interesting. Yeah. OK. And so, you know, to fill the gap, you have your poker career, you have this sort of unfortunate ending to it and this sort of maybe. you know, seismic moment personally, how does that then lead you into the world of today? And, you know, I know there's a five-year span, so I'm sure there are a number of chapters, but how did you sort of bridge to the world of tech and Estera? It took me the better part of a year after I got out of rehab to get back on track in the sense of like having a career that I was really interested in. I was mostly just doing ad hoc work here and there. Like I was doing work for friends. I did some one-off legal research projects. I got really interested in biosecurity and existential risk in general around that time. It had been an interest of mine going back to like 2016, but just something that I hadn't pursued at all while I was in my period of insanity.

I started meeting people in the biosecurity community while the pandemic was going on and got connected with a group of people who were interested in founding a company that would work on shelf-stable COVID vaccines. I think I was a fit for them because I was baseline really interested in... biosecurity. I had some experience with setting up companies from being a lawyer. I had some operational capacities that they didn't have because they were younger people. And so it just so happened that founding a company together made sense for us. So that was Alvia. That was founded in December 2021. And we created a DNA plasmid-based shelf-stable COVID vaccine that we took to phase one clinical trials. And then a bunch of scientific and market things changed, made it such that that wasn't going to be an attractive business line or product to pursue. Some other stuff happened. And then we decided to wind down the company about two years ago now. This episode is brought to you by Brex. Fred Adler, the influential venture capitalist of the 1970s, was known for displaying decorative pillows in his office that featured a signature business philosophy. Corporate happiness is positive cash flow. In today's post-SERP environment, Adler's wisdom feels particularly relevant as founders need to make every dollar work harder. That's exactly what Brex delivers. Their modern finance platform was built specifically for startups like yours. and designed to help extend your runway when capital efficiency matters most. With Brex, you get global corporate cards with up to 20x higher credit limits and no personal guarantee required. Their banking solution has no minimums and no transaction fees, while letting you earn high yield from day one with same-day liquidity. Best of all, Brex knows you were born to build, not juggle spreadsheets and finance tools. Their AI-powered platform brings cards, banking,

Expense management and travel all in one place. It's simple, scalable, and designed to get you back to what you do best, building. More than 30,000 companies, including one in three U.S. venture-backed startups, trust Brex to help make every dollar count toward their mission. Join them at brex.com slash Mario. I mean, for anyone that has been keeping track, this is sort of why I said you might have one of the most interesting backstories ever, I think. It's law, poker, a bit of insanity, return from insanity to COVID, vaccines, build that company, and then on to Estera. What is the founding story? Because Jeb McCaleb seems like he's a really fascinating character himself and has built some really fascinating businesses. Yeah. How did how did you two start collaborating? Astera existed before I joined. Astera was actually it was created in late 2021 initially. And it was kind of like Jed had a bunch of assets that he knew he wanted to donate. He created a foundation to do that. And then he got. kind of focused on other projects. His partner and co-founder CMA did the same. They were both kind of running other companies. And so nothing much happened at the foundation for the first like three years of its existence. And then they kind of like looped back around and were like, oh, we should actually do something. So when I joined in mid 2024, Astero was basically like, Jed had an engineering team that was working on neuro-inspired approaches to AGI. There was nothing much else that was happening in the foundation. And so I came in and started building out the team, building out our programming. How did you even sort of hear about it or, you know, yeah, sort of connect with this set of priorities that it was working on at the time? Jed was sort of like a fringe character in...

the world that I existed in before that. So when we were doing Althea, we considered, I think maybe did approach him as an investor because he's kind of in the existential risk curious investor circle, sort of like on the fringes of effective altruism. He and CMA are definitely not... part of the effective altruist world, but they are philosophically aligned in terms of wanting to make sure that philanthropy is actually useful and effective. And so I sort of like knew of him. I spent a bunch of time after Alvia trying to figure out if there was something specifically in AI risk mitigation that I could do that would be useful. Spent like six to nine months trying to figure out something that I could at a start or help run that would actually move the needle on AI risk and was just kind of running into wall after wall. And during the course of that, happened to get introduced to CMA, Jen's partner, because she wanted to meet people that she could play poker with. Oh, wow. No way. Yeah. So it was actually poker that was the first intro to the two of them. Did you wipe the floor with them? No, actually. We do have a home game that we play sometimes, and I am down lifetime in that game. Very tactically, I'm sure. Right. That's what I would like to believe. But no, I just like frustratingly lose every time we play. Yeah. So I think that we just met socially initially and really hit it off so strongly from the get go about like a desire to run mission oriented organizations in a way that actually prioritizes execution ability and effectiveness in the way that. usually only for-profit companies do. And so when I got tired of trying to figure out something in AI risk specifically, I shot Cime among other people a message saying like, are you hiring for anything? Are you looking for anything? And she was like, yeah, we're looking for a CEO for Astera. Do you want to talk about it? And I was very excited to talk about it.

Wow, that's awesome. Yeah, it seems like, I mean, you've assembled such an incredible group. You know, one of our completionists of this podcast, of which maybe there are one or two, will know that, you know, Eli Dorado was a guest. And, you know, he seems like just a brilliant person to have on the team as well. And so, yeah, it seems like just such an impressive group of talent that you guys have sort of begun. pulling together over these past few years. On your side, how did AI risk start to become something that you were concerned enough about that you really wanted to devote your time on and also felt like you could hopefully move the needle on? AI risk is much more popular as a topic now than it was even a few years ago, but especially compared to when I first started thinking about it, which was like 2015 was when I first like... bred superintelligence, started thinking about it. I think various risks from AI seem like the most important topics of our time to me. My assessment of which ones are particularly important has shifted over time, in part in response to what else is happening in the world. So at the time that I was really thinking about trying to start something or do something in the area, I was still mostly thinking about alignment risk and technical alignment risk. I think that is still something that is incredibly important and neglected relative to its importance. At the same time, it is a topic of discussion and study at all of the major labs. beyond the major labs like it is a well understood body of risks um and so i think that like the the risks that i'm now most concerned about are ones where the the way forward is really really unclear because they aren't technical risks so to give an example of what i'm saying um i think

Risks from like disintermediation of humans as like the primary entities of economic and social interest is a real concern. Like soft takeover by AI systems that just increasingly displace all of the activities that humans do in such a way that the world becomes like less and less comprehensible and less and less meaningful to humans. These seem like. the most important risks to me as of the last couple of years. And I am wholly unsure what to do about them. So I'm not sure that that is... actually responsive to whatever question you asked, but that is sort of like the trajectory of my interest in AI risk of various kinds. No, that makes sense. I think what you're saying is, you know, alignment remains this sort of massive threat, but there are now more eyeballs sort of on that as something that, you know, we really, really, really need to be extra careful about. And maybe these, you know, concepts around soft takeover are understudied. And, you know, to make sure I'm understanding something like a soft take would be. takeover would be, you know, we have so many effective AI agents that they're actually the one sort of accumulating salaries and money in exchange for the work that they're doing in the world. And it gets to a point where they're actually controlling the majority of the resources such that, you know, they can exert political power or cultural power or economic power. And we sort of reach a point where humans are actually not the wealthiest party, so to speak, among among the different species a lot of my concern is like um maybe there is a small group of people who are able to continue extracting wealth and and increasing sums of wealth they might get incredibly wealthy off of ai um while at the same time the scope of like

Human participation in labor, in the economy, gradually decreases. Humans feel less and less agency, less and less control, less and less meaning over their day-to-day lives. And I think that, like, there are a bunch of trends beyond, say, AIs taking human jobs that contribute to this. Social media, to some extent, is like the first wave of this process where it seems like a lot of the things that provide meaning to human lives are slowly coming apart at the seams because of the way that humans interact with recommendation algorithms, the way they interact with bots that are not even necessarily trying to optimize for things that are bad for human values, but that are just like designed to. increase engagement in ways that end up being harmful to humans. And so I wonder what happens when you have like application of similar pressures, like extractive pressures across a wide variety of human interactions and sort of how How hollowed out and disconnected the human experience might become. Hollowed out was exactly the phrase that I was thinking of as you were talking about this. It sort of feels like, you know, the way that maybe happens is that it feels like convenience in a lot of these cases or it feels like speed. And the tradeoff that you make is agency or is like the right amount of effort that you need cognitively to not. atrophy. And so, you know, you're having sort of systems saying like, here are all the decisions you might want to make today queued up, like good. And you're sort of giving the thumbs up. But the thumbs up is, you know, almost meaningless at that point, because the amount of work that's been abstracted, maybe it's not making the money on your behalf, but it is sort of functionally puppeteering you in some way. And you're the sort of doddering old fool that it's maneuvering around. Is that roughly right?

Yeah, I think so. And like all of the all of the frictions of life still they get eroded away in a way that just leaves us with this heavily dopamine steered kind of smooth tunnel of an existence. It's a really disturbing and very plausible future scenario from my perspective. Yep, I agree. How do you guys start to think about researching that? Like, you know, that's such a big intractable, you know, a million different possibilities you can imagine carving through there. How do you start to think about what are useful questions for us to ask ourselves? How do we start to surface useful information? I have no idea is the real answer. And it's not for lack of thinking about this. I think it is just the most challenging problem that humanity is currently facing. And it feels actually overwhelming to me. And I don't understand how we are going to make it through. I have this really intense baseline optimism as a person that makes me feel like we will figure out a path through. Humanity will like figure things out. But actually figuring out what the pathway is going to be is really challenging. I think I am increasingly moderately optimistic that. We will hit a slowdown in AI, which I think would be really good for allowing us to get our bearings as a species and figure out how we are going to respond to some of the technological and governance changes that are coming. But that could also not happen. And we could be in a situation where we have really strong. artificial intelligence in three years and we don't have the social technology necessary to address that. And I just don't I don't know what's going to happen. From Astero's perspective, is it, you know, the goal to find, you know, a new set of builders who are building technologies that help help the social technology piece or that are, you know, security minded or sort of how do you think about?

Yeah, the role of the institute or the organization in this world. I think about us as trying to help steer the development of novel technologies while we are passing through this period of intensely fast change. So I think that like. A core view of the world that animates a lot of the Foundation's activity is this view that the world may be changing really dramatically and very quickly, that very few publicly-minded institutions are going to be in a position to respond quickly simply because they don't have the appetite for or capacity to respond to change very quickly. government institutions, large foundations, academia. I think that the future will go very well for a small number of people and poorly for a larger number of people. And so we are kind of trying to do our best to make sure that technology benefits a large number of people. We are focused in particular on creation of the types of public goods that are not adequately incentivized by markets, but that we think will help ensure that the world is good and that people have high welfare in the future. An example of this would be like climate technologies that are not created by markets for various reasons. Maybe I'll leave that as an example. I know up front you sort of mentioned about some of the investing side of things. Have you guys started to make any investments publicly or companies, you know, startups that you're excited about from that vantage? We just led the Series C for Last Energy, which is doing small modular nuclear reactors. And that's... the kind of thing that i'm really excited for us to be focusing on um that's an example of a a round that might not have come together if we weren't participating in it um but it is a technology that i think is like very good for the world likely to be immediately useful within the next like five years in a way that very few nuclear technologies are um so that that's like

an exciting thing that we're working on. Eli is amazing because Eli has this deep understanding of energy technologies and he just like got to benefit from onboarding him in that way. And so he has been a font of knowledge for us. That's awesome. How do you think about like the balancing the sort of philanthropic stuff with the investment stuff? Like how do you think those two things fit together and how do you hope they work together? I think of them as Intimately related, like the same thing, basically. In our investing, we do have some investing that we do for just the perspective of endowment management and trying to make investments in a way that will increase profits and grow the size of the endowment. A lot of the investing that we do, though, is as an alternative to grant making. Most foundations have a very clear distinction between these two types of activities. They do endowment management. They often have investment managers that specifically do that. And then they do grant making. Yes. And grant making is their sole form of charitable activity. And then we're... fairly unique, not the only ones that do it, but possibly the only foundation in the world that does it as the primary philanthropic activity. So we are focused on basically trying to figure out how to make philanthropic money go further. One way to think about grant making, which I think I watched some of Eli's conversation with you and I heard him use this way of describing it, is like grant making is a form of philanthropy where you lose 100% of your money 100% of the time. And a lot of times that actually isn't what makes sense. So there are often ways to stretch philanthropic money further and ways that allow you to recycle philanthropic money and use it repeatedly for additional efforts to like get organizations or projects off the ground.

Investing is one way of doing this. We are experimenting with loans and loan guarantees. There are also activities to sort of provide a multiplier for philanthropic capital. So something that we are. we are increasingly thinking about is like how to use philanthropic capital to recruit other forms of capital to philanthropic investments. Basically, like how to use philanthropic capital as first loss capital to make things that would not otherwise be attractive, marginally attractive to more traditional forms of capital. And I think that this is something that you should expect to find and do find often with emerging technology is there's a variety of things that would be socially beneficial to have exist in the world that are barely uninvestable by traditional investors because the risks can't be underwritten. And if you have a philanthropist that is willing to make that investment less risky to other forms of capital, you can really leverage the philanthropic capital to recruit other money. And so we're focused on finding ways to basically stretch philanthropic capital as far as we can. Really interesting. Before we sort of get into the wrap up questions, I feel like I must at least ask a little bit about agency because I think it's become, must be one of the most read articles on Substack, at least in the tech world. And I think it really resonated with a lot of people, including me. And I'm sort of, I'm managing to bungle this introduction, but. You wrote a wonderful piece about what it means to have agency that really resonated so broadly. Maybe you can tell us why you felt the need to write that piece, sort of what inspired it and what it means to really have agency. Yeah. So the first thing that I wrote about agency was this piece, How to Be More Agentic, which was just kind of dashed off. I really didn't think about it. I didn't think that it would be a topic of significant interest to people.

First thing I ever wrote on Substack. Oh, wow. Right out of the gate. That is not a typical experience, let me tell you. There is obviously real hunger for it because I got my book deal off of that first Substack. People just really responded to it. So I think agency is something that is sort of a hot topic now in tech world. And people have different things that they mean by it. When I talk about it, I am talking about a capacity to both notice and respond to in action all of the degrees of freedom that one has in their life. And I think that this is of interest to people now for a variety of reasons, one of which is this crisis of meaning that we see. Starting with social media, but probably expanding as AI, as the role of AI spreads in society, where people are feeling uncertain about the way that they extract meaning from their lives in the face of this gradual loss of the things that traditionally more us to our lives. I think that the thing that... is different about the way that I talk about agency. And the reason that people tend to respond to my writing on the topic is I think about agency as not an inherent trait. So it's not like raw intelligence or something like that or height. I think about it as a really learnable, transmissible discipline or way of approaching the world. And so I'm very focused on what are the concrete things that you can do. to display higher agency and make your life more like you want it to be. So I think that that practical emphasis and also the perspective of somebody who started life high ambition, low agency, went through a period of incredibly low agency with the drug addiction. So somebody who's like had highs and lows and is able to sort of share some of what

accounts for the physicians. I think that is really what people are responding to. Really interesting. If someone wanted to try to make themselves a higher agency, for those who didn't read the piece, like what would be, I don't know, a couple things to try out? I, for example, I really like your suggestion. You have an open suggestion box, which is one of them that I think is very clever and also seems painful. I really advocate for having an anonymous feedback box. I think the degree of pain that it involves is actually quite a bit lower than people imagine it will be. The balance of nice versus not nice feedback is better than people think. I also think, though, that there is enormous value in being willing to take that step and get... real information about who you are that is not visible to you. So I think that like basically we all have things that are not visible to us, but that are visible to most other people that we might benefit from knowing, but that are like socially awkward to tell us. And I think that if people can sort of get over the aversion to the pain of seeing themselves clearly, it can be an incredibly potent tool for self-improvement to just have a better understanding of what other people see. So I highly recommend it. Sounds tough. But I'm going to think about it. Yeah. I know many people who have done this and found it to be really beneficial. I know a couple people have done it and just found it to be... not worth the psychological pain. So I'm not going to say that it's for absolutely everybody. But on balance, I think most people end up liking it. In some respects, I have an open suggestion box every time I send out an email from the generalist, but not everyone's response is anonymous. So it is different. I think that anything that you can do to see yourself more clearly and to engage more directly with the world tends to be agency increasing. A lot of

what I what I think about I talk about is just like getting more real with yourself and with other people and breaking through some of the layers of unreality that filter all of our social interactions and then there's there are other aspects of agency that are just about sort of less about seeing yourself clearly and more about learning to see optionality in the world that you become blind to through habituation um so one of my one of the actually most potent things that i think you can do to increase your agency which sounds incredibly boring and so i don't write about it as much as some other things is just um training yourself to ask over and over over the course of a day like 10 times a day whether there's a better thing what whether there's a better way to do whatever thing it is that you are doing. Because so much of our time is spent doing things habitually in ways that are actually not optimized for the results that we want. And if you can learn to break out of that sort of habitual way of approaching the world, I think it opens up a lot more degrees of freedom. Okay, super interesting. I have two questions about that. On the last point, is it more useful to think about how to do the thing that you're currently doing differently or whether you should be doing a different thing? I think both are useful. So, which is a very unsatisfying answer. I think that. There are ways of engaging with the world that are more curiosity driven and more creativity driven than the ones that we habitually approach the world with. And I think that asking yourself this question repeatedly is a way of starting to train that muscle once it has after feed. I think there's like a separate set of questions that are all about like. Am I even doing the right thing? Do I have the right goals? Like I think about this as like a discrete practice. Ben Kuhn calls this staring into the abyss, which is like trying to think critically about the things that you'd rather avoid thinking about. And so this is all about like examining the big questions in life that we instinctively shy away from.

Like, am I doing this only because of its social benefits as opposed to actually caring about it? Does this relationship that I've put a lot of effort into actually serve me? Is it something that I would stand by on reflection? So I think that there's like a separate skill set that is about learning to be deliberate and reflective about those types of questions. But you kind of need both. Yes, that makes sense. My other sort of question related to some of these agency ideas was, if you're comfortable sharing, what has been like a few of the most useful pieces of feedback you've had pop into your suggestion box? So I've gotten a lot of feedback on the way that I engage with people, especially when I am stressed. I was not well socialized as a young person, in part because of this autism that I mentioned. I think that I have learned how to be warm and engaging toward people through deliberate practice over the course of the last 10 years in particular. But it is not something that comes naturally to me. And there are a bunch of social dimensions of interaction that don't come naturally to me. periods of greater stress. Those are kind of like the first things to go because they are a more deliberate layer of social engagement. And so I can become withdrawn, cold, seeming like I don't care when I do. And this is the category of feedback that I have gotten that has been most helpful and necessary for me to hear, I think, because it is something that held me back as a manager for a long time and that I've been able to not not completely correct, but make progress on because it was called out to me and because I understood better how I was being seen and couldn't be in denial about that. Really interesting. Well, with that in mind, maybe we can move on to sort of a couple of our wrap up questions. I always like to ask folks these these couple questions.

One is, if you had unlimited resources and no operational constraints, what is an experiment that you would like to run? One that I've thought about recently, which just isn't really a fit for Estera. But have you seen this heat map thing that is always on Twitter? People use it to justify whatever their political beliefs are. It's like liberals versus conservatives, how far their moral sphere of compassion extends. No, I haven't seen this. OK. OK. It's a really interesting Rorschach test of what people want to believe. To some extent, it shows how liberals versus conservatives think about their sphere of compassion and basically like how far out that extends. Like, do you care about distant people? Do you care about animals? Do you care about like more theoretical things? And I have. gone and tried to understand this study based on actually reading the study because it gets leveraged by both sides of the political spectrum as ammunition. It gets leveraged by liberals to say that conservatives only care about themselves. It gets leveraged by conservatives to say that liberals care more about rocks than they do about their own families. And I've found that the... The actual study is extremely unclear in its methodology. And so I would like to repeat that in order to have clarity about what people actually believe. Like, I would be surprised, actually, if you haven't seen it at some point. Maybe you don't like remember seeing it, but it comes up over and over again in political discourse. And I think it's actually just very unclear what the study shows. So I would love to read you that one. All right. I'm going to have to look it up and reacquaint myself with it. Have you ever read The Righteous Mind? Is that height? Yes, it is. OK. Yeah, Jonathan Haidt. I think I did. Yeah. OK, because that reminds me a lot of that idea, which is that, you know, testing sort of asking different cultures and different groups to rank their their moral priorities and how, you know, everyone is sort of it's not about good or bad or sociopathic or anything else. It's just sort of like, yeah, people are prioritizing slightly different things. And, you know, there's all these different places on the spectrum you can sit from.

you know, really caring about tradition to, you know, being more high openness and stuff like that. So, yeah. Anyway, it's been a few years since I've read it, but that came to mind. I think I read it back maybe like five years ago or something. Yeah. On the topic of books, my ending question is always if you could assign a book to everyone on Earth to read and understand, what would you want to assign to people? I think it's got to be Impro, especially based on the conversation. I mean, that would be really high on my list anyway. It's one of my favorite books to recommend to people. And I think that, like I said, it is one of those books where you read it and it just kind of colors so many of your interactions from that point forward because it's like you see this additional language that people are communicating in and it's just super fascinating. Well, it's always satisfying. to end back at the origin. So we managed to take it full circle. Thank you so much, Kate. I really enjoyed this conversation and enjoyed learning from you. Thank you so much. That's it. Thank you for listening to this episode of The Generalist Podcast. Please subscribe on Apple Podcasts, Spotify, or your preferred podcast app. Ratings and reviews help others discover these discussions. So if you enjoyed the conversation, I'd be grateful if you could take a moment to leave one. For all past episodes and more, visit us at thegeneralist.substack.com See you next time as we continue to explore the future.