(2026-01-16) Stacking The Odds Cate Hall On Agency And Outlier Success

Patrick McKenzie: Stacking the odds: Cate Hall on agency and outlier success. This week, Patrick is joined by Cate Hall, CEO of Astera Institute and author of a forthcoming book on agency, to explore how individuals can systematically develop higher agency in their lives. They discuss the selection effects that draw agentic people to fields like poker and startups, the importance of being comfortable with ignorance and feedback, and practical strategies like asking "Is there a better way to do this?" ten times daily.

Patrick: Hi everybody. My name is Patrick McKenzie, better known as patio11 on the Internet. And I'm here with Cate Hall, who is the CEO of Astera Institute and has a forthcoming book on agency.

Patrick: Thanks very much. So I*'m obsessed—well, obsessed is not quite the right word, but quite interested in the topic of agency in the last few years. Both how it plays out in our personal lives and how there are some institutions which seem to be sort of hitting above their weight class in terms of empowering people to have it. And then there are very many other institutions which seem to do an excellent job of killing it as early and thoroughly as possible in people's lives.***

Patrick notes: Why is there such dynamism in Silicon Valley, including among young people, but our leading institutions of higher learning (schooling) almost aggressively clamp down on actual productivity by young people? Why did my professors model receiving a series of increasingly impressive grants, but not doing anything ex- staying on the happy path for grants, as success when I was in my early twenties?
YC doesn’t do that and that matters.

Why did it end up being VaccinateCA who got the covid vaccine on Google, and not e.g. the CDC? Why will I have to expend heroic efforts to get into the room again if there is a “next time”, while the current constituents of the room where it happens enjoy de facto tenure, irrespective of underperformance?

Cate: Yeah, so I think it's an interesting observation. My head immediately goes to selection effects. Because if you think about something like poker, it tends to attract agentic people. I don't think poker causes people to be agentic. But it does have that selection effect. On the other hand, you have something like law, which is where I was before poker, that definitely selects for low agency people. It probably also suppresses agency to some extent, but I think it's as much a question of what types of fields and institutions people gravitate toward as the effects that those institutions have on the people within them.

Patrick: I think that's certainly the case, at least in places like the tech industry, which for many years, and I think to a lesser degree these days, most people would say—you know, the famous Apple advertisement "we're the creative people, we're the thinkers, we're the rebels," et cetera, et cetera. And tech had much broader paths into it than most employers of large numbers of people in the professional managerial class.

But it's become more of a beaten path. And the entering classes at tech companies these days look more like the entering classes at Stanford or Harvard or an investment bank than they did even 10, 15 years ago, I think.

Cate: Yeah, absolutely. I think tech has gone through that cycle that all things do—you know, the geeks, mops and sociopaths cycle. [Patrick notes: I don’t necessarily endorse this essay, but one reason it resonated so hard with people is it points in the general direction of a real phenomenon] ((2015-05-29) Chapman: Geeks, MOPs, And Sociopaths In Subculture Evolution)

Y Combinator's changing demographics

In the very recent past, YC had more people who were college dropouts than people with postgraduate degrees. And as of a recent class they're at something like 65% postgraduate degrees.

Part of that is that they're wisely responding to a change—many of the companies they're funding are AI-first. And so they're getting an increasing number of people from university AI labs.

But part of it is definitely that Y Combinator was essentially pitched in the beginning... like "do this instead of doing grad school" for people who wanted a relatively institutionalized path up versus throwing themselves into the wide world of capitalism.

This appealed to people that the existing life scripts weren't quite right for.

And then YC itself became more institutionalized over the course of the last couple years

Parallels between poker and startups

Cate: I think it's a really interesting observation. So now that you're describing it, I see a really interesting parallel between poker world and startup world. Which is, so there's this old guard of poker players who were maybe the people who were already poker stars around the time that the poker boom started. And they had a particular way of playing that was maybe less mathematically rigorous on the whole.

When there was this huge wave of popularity for poker starting in the mid-2000s, this new crop of people sort of started gathering. And those people were extremely rigorous

I see a similar thing in startups where there was a period of time when everybody was like, "oh, all the best startup founders are in their twenties

seems like the conventional wisdom for both of those things has shifted as that cohort has aged and now you see the best poker players are in their late thirties. And the best startup founders and the ones that people really want to give money to, tend to be in that age cohort as well. Maybe in their forties

Patrick: If I can just have a very minor rant—similar in the way that there was an old guard in poker, which might have had great table reading skills.

table reading means you are live reading... You are picking up on some physical signal that a person is giving that can give you information as to the state of their hand

That explanation out of the way, the way we previously evaluated startups bordered on magic in VC land where it was very connection-based.

And so after Facebook was in the news, it was like, "oh, all the successful founders are in their twenties, obviously." When a slightly more rigorous analysis—well, wait a minute, if we look at who actually has the exits here. And granted there's some power law that goes into that too, but yeah.

My general theory, both with respect to poker and with respect to startups at various times in the lifecycle has been when there's some terra nova in society where there's a lot of economic value being created somewhere, the people who get most of that economic value in the first years are sort of pioneering spirits. And they're often pioneering spirits because they took a look at all the other ways that you could plug into society and decided, "eh, not quite for me." And so they tend to be a little bit weirder

then the rest of society gets the memo and the value doesn't all get extracted, but people start to bring other societal advantages to bear—like the capability to get investment, the capability to build rigorous organizations that scale whatever the initial advantage is, et cetera,

And then after a few years, it's not like the frontier disappears, but it becomes more integrated into the rest of society.

Cate: Yeah. I think there are some really interesting dynamics at play here. Again, I see this parallel where it's like, with internet poker, that internet poker coincided with this explosion of interest in poker

This created this massive opportunity for people who were these prospector types. Where there's a ton of money available, there is not a lot of systematization.

so at first you have just sort of brute force, almost systematization, where you start having people using tools

And those people take over, but then you do as it gets more and more competitive, it becomes an AND thing rather than an OR thing.

And I think what happened is the skill level in a quantitative sense sort of asymptoted to game theory optimal to a point where there aren't huge edges to be found in improving your game theoretic play a little bit more.

so you get competition increasingly in all of these different aspects of the game. And it's no longer sufficient to just be good at the math or good at the engineering or whatever is required to start a startup. You have to be good at the whole suite of things

Patrick notes: I had my first software company in 2006 and was anomalously good at SEO relative to some very big firms, partly because I was willing to read some forums where the witch kings of the Internet were discussing what was working back in the day.
And it's interesting how those informal sites of cultural diffusion sort of give way into more formal institutions. These days you don't get your advice on SEO from forums. You typically get it from either a consultant that you've paid or a partner at YC

It seems to me like one kind of under-appreciated lens with regards to agency is who is willing to go to places that are not on the approved list of places you can learn from?

So what are other sort of things that agentic people do that might give them an advantage in the early stages of whatever the new industrial wave is,

Cate: Yeah. So I think, even at a more basic level than specific tips, they're just sort of mental habits that agentic people have. And one of them is just simply asking sort of continuously whether there's a better way to do something.

I just left post-it notes for myself everywhere in my apartment asking "is there a better way to do this?" And then I would remind myself to ask that about whatever I was doing throughout the course of the day.
And I think if you can train yourself to earnestly ask that question 10 times a day, you're most of the way there on agency.

Other things that I think are part of the mindset—there is this desire to look in inconvenient places for real edges. So there are a lot of things that you can do in many situations to improve your odds of success that people just don't do because they're not part of the standard playbook. They're kind of aversive. And they don't seem necessary for success.

what's an example of this? Personally, anything that looked like excellence in networking, I would say was one of these for me, for most of my life where I just wasn't willing to really pursue relationships with people who I had professional overlap with and interests because I just didn't like it. And I think that that's a relatively common one. I think that if you sort of go out of your way to develop relationships with people in the hopes that it will lead to opportunities to do interesting things in the world, you can become a much more impactful person

some people get the memo early in life that reality is a team sport and being able to tap people in your network to take care of things is very helpful. And some people get a very corrupted version of this, which is like, "relying on another person is cheating somehow."

to make a very concrete example when I was originally publishing essays, I would be like, "okay, I will certainly never show this essay to anyone before I publish it, because that could influence them to decide to share it to their audience. And I wouldn't want an unfair advantage

Patrick: And these days it's like—granted, I still don't show most of my essays to anybody prior to publishing them. But I'm at least aware that if I was attempting to play this game to win, I would certainly show it to people both to get their feedback on it. And because, contingent on them giving feedback, they feel some bit of ownership about the essay and are much more likely to share it with their audience than they would if they were seeing it cold from Twitter on the day it is released.

just asking the question of "how can this be better?" generating surprising amounts of alpha or edge,

But I worked at Stripe for a number of years and there were very highly placed people in Stripe that essentially had a button that they would push in almost every meeting. Like, "all this sounds great. Do you think we could do it faster?"

Could I just choose to be better at the thing?"

Cate: I think that a lot of the things that increase agency look like just learning to have less ego about certain types of things

I think that figuring out how to be comfortable getting real feedback from the world is like the highest leverage thing you can do

giving people a way to tell you those things in a way that is not threatening for them is so high leverage for your own improvement on whatever dimension you want to improve on. I'm a huge fan of anonymous tip boxes because of this

I also think that just learning to be comfortable with not already knowing everything is huge

things like saying, "I don't understand what you just said." People love that. People love to explain it. They love the honesty

Patrick: Yeah. I think this is particularly common among people who are broadly high-competence. Particularly because they've been tracked in institutions that have socialized them to believe that you start at a hundred points and you can only go down from there.

And this instills in many people a sort of risk aversion and aversion to new things

institutions become even more tracked than the structural reality of the institution.

Exploring growth mindset

Because it's really apparent once you sit down and think about it, just how much personal improvement you are leaving on the table if you're inflexible in these ways mentally

AI and personal improvement

one can have conversations at a variety of points up the skill ladder with an AI, and often not feel like the AI is going to remember and judge you harshly for it

And so I've been trying to get better at painting the last couple of years

And just having a record of three years of photos of finished pieces and, oh, I think I'm actually descriptively getting better at this has been a bit invigorating.
I get fun things to decorate my room with... one of my favorite, least recommended ways to use an LLM. When I'm halfway through painting a piece, I will—and I'm a very, I would say probably low intermediate painter at this point relative to skill levels in the community—I will take a photo and say, "okay, here's a half painted piece. And my reactions to this are, I think this troll is a little too dark. I want him to be green, but not cartoonishly green. What could I physically do right now to achieve that effect?" And LLMs are surprisingly good at giving you action feedback about what things to do in the physical world in a totally non-judgmental fashion.

Learning with AI: strategies and cautions

Cate: Yeah, I think I have—so I am a huge fan of LLMs and incorporating them into learning processes. Just because they're so efficient for that, you know, I have, as I'm sure most people do, a few different ways of using them.

One of my favorite ones for learning a new subject matter area is start with "explain this to me like I'm five." Then like 10, 15, like, you know, you just escalate

I think it's easy for people to become really insular because of reliance on LLMs in this way.

The value of human interaction

there's a couple of obvious icebreaker level questions that I could ask. Maybe I'll get those out the way with the LLM and in place where it's relatively unlikely to hallucinate. And then catch more of the lingo the first time around. And like I had my first question be a decent question, like, 'okay, what I got out of that was you just said the EBITDA goes up. My understanding of that is X. Can you check me on that?'" And then again, people love being asked confirmatory questions.

Professional gamblers and their unique insights

We had an episode recently with Zvi Mowshowitz, another professional (well, former professional) gambler—about his tips and tricks for prompting successfully. And that caused me to reflect on: there are a few populations which punch way above their statistical weight in terms of the people who are involved there tend to lead interesting lives. ((2024-08-08) McKenzie, Bet On It; Zvi Mowshowitz On Professional Gambling, Trading, And AI Futures)

I interview a grossly disproportionate number of professional gamblers

why is it that people who decided at one point, "yeah, I'm going to gamble for money as the way I put food on the table," end up doing very interesting things in the world?

Cate: It's a great question. I think there's probably multiple factors. So one is just the types of personalities that poker selects for. So these are not always the most organized people. They are, I would say, first principles thinkers. A lot of the time it's people who are maybe slightly hostile to social scripts in a way that makes them rebellious. Not deferential to the way things are currently done. I think it just selects for people who have a lot of degrees of mental freedom.

I also think it obviously attracts people who have a certain orientation to the world that is like thinking in bets. And I think that way of approaching the world is just inherently adaptive in modern society. Sort of thinking systematically about, given the whole range of possible ways I could spend my life, how do I want to decide where to allocate my time and resources?

And I think that that tends to serve people well once they get out of poker too. Because it tends to cause people to think deeply about the things that they can do that might be most profitable, most impactful

Understanding agency and its development

so you have a book coming out? Yes. What is the angle you take in the book?

Cate: It is intended to be a practical guide to agency. So the essential framing is I've experienced sort of intense highs and lows in terms of agency in my life

So I have done some really impressive things

At the same time, I've also had periods of severe addiction, including a three year period of addiction in my thirties that basically completely crashed my life.

so the frame of the book is like, how can you—how does one go from very low agency, a very low agency state, to a high agency state

I think people have not put that much thought into how to systematically develop agency, but there are ways of doing it. And so it's meant to be a practical guide

Patrick: I would absolutely endorse the "agency is not a fixed quantity over the course of your life." There's—I can't remember in my personal experience of life a feeling like I'm 20% smarter than I was yesterday, or 20% more capable.
But I've definitely had several hundred percent swings in agency on a yearly basis. [Patrick notes: And in the relatively recent past, too!]

And partly it's just deciding to do it

I think we spend a lot more effort on a societal level on constraining agency than we do on inculcating it. Particularly the school system. I loved schools when I was going through them, but oh my, do they want to chop off both ends of the distribution and they are brutally effective at it.

if your parents object to it, you are now—like, the objection is itself a problem to be managed by the school.

And it's interesting to see people with sort of alternative schooling modalities and similar that are trying to avoid that. It is an open question on whether any of them wins out. It may be that something of what we want to get out of school, and the economies of scale that we want to get out of it, might be almost inherently inimical to having kids just doing what they want to do.

Triggers for increased agency

what are some of those concrete things that people can do to inculcate agency in themselves?

Cate: So I think even before that, I'm curious. Because one of the things that is most interesting to me is I think that, as you said, there are these step changes in agency that people experience. And I'm really interested in the question of what triggers those changes.

Patrick: Something of it is learning from the environment or peers or similar where there's a person socially close to you for whatever reason that is far above the mean and where you can recast agency as something that you actually want. I feel like I grew up in a culture in which "that person is ambitious" is inherently a negative moral judgment with respect to them

Being able to see up close to the example of these people are clearly ambitious in a good way.

And like just having the notion of you don't have to simply walk the default trajectory given the educational attainment and career position, et cetera that you have in life

There's been a few times where it's been response to an emergency situation for good or bad. The VaccinateCA experience—people were dying. What do you have to do? There was a private emergency in my life many years prior to that, that triggered a fundamental reassessment of what I wanted out of life. And I stopped playing World of Warcraft and started getting serious about making a software company after many years of saying I would like to have a software company one day, but there is World of Warcraft and the guild is meeting at eight o'clock.

Cate: Okay. That's very interesting that those line up fairly well with I think the things that were triggers for me too. Definitely having the experience of having peers that are higher agency is undefeated as far as I'm concerned in developing people's personal agency.

my experience co-founding Alvea, which was a pandemic era vaccine company with three other people. And those people were significantly higher agency than me. And I think there was some sort of shock to the system that happened from seeing how radically they moved through the world.

We—so one of the things that we did early on in the company was we set a goal of submitting a clinical trial application for our new shelf stable vaccine within three months of when the company was founded. This is a truly insane thing to do, but we did it, and that was—and it was accepted later. This was driven entirely by the agency and personalities of the two co-CEOs at the time

I think of a lot of what we try to do at Astera as being about trying to increase the agency of scientists and technologists who come work with us. Because we're often bringing people in for a limited period of time, helping them launch things and then spin out.

misery can be an adequate nudge.

Patrick: That was definitely part of what was going on. Yeah. A few times in my career, after—sometimes people ask me what I was thinking when I wrote a thing about a particular thing, and I'm like, "well, there's the surface level of what I was thinking about the topic I was writing about, but the meta level was I have no way in the day job out of the present circumstance I find myself in." And so if there's gonna be any advancement in life that's going to come from the thing I'm doing outside of the day job, if that is writing right now, then I'm gonna write the hell out of it.

Cate: So I'm @CateHall on Twitter.
I think Substack is my preferred platform these days. I'm very pro-Substack.

Patrick: I am extremely pro-Substack as well, even though I don't use them. It's nice to see more long form writing in the world and knock on wood, hope that continues. Be agentic, write more stuff for the Internet, please. Alright, thanks Cate for coming on the program today.