How to Build a Builder
Our episode with Dr. Gena Gorlin
Our episode with Dr. Gena Gorlin is live! Scroll down for episode links & a transcript.
If you’re anything like me, the idea of aiming for "psychological perfection” will give you heart palpitations.
We’ve been brought up to think that fierce ambition — let alone the quest for something as hubristic as perfection —should be carefully managed at best, feared at worst.
Surely, psychological perfection is the stuff of fantasy (or delusion). You may as well aim for laser vision, superspeed, or telepathic powers.
disagrees.Unlike many of her colleagues in clinical psychology, Gena doesn’t aim to lift the floor of her clients’ ambitions — she wants to raise the ceiling.
Rather than focusing on resolving underlying issues or deficits, Gena has spent the last few years dedicated to equipping clients “with the psychological wherewithal to conceive and execute on big, ambitious ideas.”
Her conclusion?
Psychological perfection isn’t just an abstract ideal. It’s a tangible, practical, achievable state of being — a mindset that can lead us to healthier, happier, and more fulfilled lives.
So, what is psychological perfection? And why do we fear it?
Gena describes the psychologically perfect people she’s met as being “on a constant trajectory of building and growing: of envisioning and vigorously pursuing ever-new heights of perfection in their work, their relationships, and, yes, their own psychology.”
Notice something? These people aren’t perfect because of what they’ve achieved. Perfection isn’t something they suddenly have, like a tattoo or a slick new haircut. It is a state of being. Psychological perfection, in other words, is a process — a way of life born out of action:
“We do not “build to live” or “live to build”; rather we live by building, which is the only way to live as a human being.”
Gena identifies two common mindsets that hinder our pursuit of psychological perfection: the Drill Sergeant and the Zen Master.
The Drill Sergeant: Why Perfectionism Isn’t Perfection
The perfectionist lives in a constant state of dissatisfaction — ever disappointed with their own work, constantly at war with their own perceived inadequacy.
You see, perfectionists harbor a second voice, one that has infiltrated and occupied their brains like a Navy SEAL. This is the unyielding, dictatorial, and cruel voice of the Drill Sergeant.
The Drill Sergeant, entrenched behind the enemy lines of our psyche, governs our every action with the rigidity of an authoritarian. He clings to an arbitrary standard—one inherited from parents, peers, school, or society—and enforces it with an iron fist.
“I must attend an Ivy League university.”
“Working 80-hour weeks is the only path to success.”
“I must spend five hours re-formatting this slide deck before sending it to investors.”
Life dictated by the Drill Sergeant becomes one long struggle — a series of sacrifices (long hours, damaged relationships, abandoned health) in service of an arbitrary ideal we never truly chose in the first place.
The Zen Master: Why Ambition Isn’t the Enemy
In The Odyssey, Odysseus’ journey home to Ithica saw him encounter many Drill Sergeant-like antagonists, not least the mighty Cyclops, Polyphemus, a hulking force of blood, bone, and muscle.
It took immense strength and even greater cunning to overcome Polyphemus. But Odysseus was not prepared for what came next: the shimmering allure of Circe, whose luxurious home promised refuge from his tiring quest. Odysseus indulged himself in comfort, and a full year passed before his men finally persuaded him to refocus on what truly mattered: returning to his wife in Ithaca.
Like Odysseus’ entrapment by Circe, we too can be lured into complacency. Having struck down or silenced our Drill Sergeant, it can be tempting, like Odysseus, to slip into the warm embrace of stagnation—to reject the pursuit of excellence and convince ourselves that we don’t care about the outcome.
This mindset, Gena argues, is equally pernicious. It results in a deadening of ambition, a quickening of defeat, a precipitous decline in self-belief.
“In muting the abusive voice of the “drill sergeant," Gena writes, “they [Ed: those who embrace the Zen Master] also mute their desire, their passion, their will to find a way. They settle for “ok” jobs and “ok” relationships, foregoing the stressful turbulence and risk of failure that more ambitious moonshots would bring.”
The Zen Master fears the climb, pre-emptively preventing us from experiencing the joys of the summit.
The Builder
The Builder mindset is not a bridge between these two extremes but an alternative, one born from within, not without. Says Gena:
“A builder chooses what she wants to build, and she holds herself accountable for the work of building it. She is not beholden to any inner or outer drill sergeant; only to her own independent, carefully formed judgment of what is worth building and how best to go about it.”
The building blocks of this mindset form the foundation of Jim and Gena’s conversation today. They discuss why positive agency, not fear, is the norm for healthy human functioning, how persistence is a superpower, and much more.
We hope you enjoy the conversation. As always, if you like what you hear, please leave us a review or comment below.
Links & Transcript
Jim O’Shaughnessy:
Well, hello everyone, it's Jim O'Shaughnessy with another Infinite Loops. Today, my guest, Gena Gorlin, who is a clinical associate professor at the University of Texas at Austin, and the proprietor of Building the Builder's Substack, also widely published in many of my favorite publications like Every and others. Gena, as I was getting ready to chat with you, I was like, I think I pretty much agree with everything she says.
Gena Gorlin:
Clearly I haven't been controversial enough because there's got to be some fault line. We'll find something.
Jim O’Shaughnessy:
There's just got to be. But first, welcome.
Gena Gorlin:
Thank you.
Jim O’Shaughnessy:
And I guess let's set the stage with, you say that ambitious people are an underserved tribe. Why?
Gena Gorlin:
Tribe, that's an interesting paraphrase. Yeah. So in the field we talk about underserved populations in the mental health field and serving professions generally. And typically what we mean is that this demographic group, because of disadvantages, whether that are financial or physiological or economic, social, this group is an underserved population in the sense that they're struggling and need more support than they're currently getting.
Gena Gorlin:
But what I've come to understand and believe about entrepreneurs and really ambitious builders, ambitious innovators generally is that they have distinct psychological needs, not because of a particular problem that they come built in with, not necessarily because they're anxious or depressed or poor. Although plenty of them struggle with all of those things. But because of the nature of what they're trying to do. Because of what they're choosing to undertake. They're choosing to build a company, they're choosing to carve out their own path as an artist and really try to figure out a way to make a living and develop a business model without selling out their creative vision.
Gena Gorlin:
They're trying to bring people on board to a new initiative of which they're the only and final boss, and the buck stops with them and there are no guardrails. There's nobody who's going to call them out if they've gone down some BS garden path for weeks and weeks. And it's really hard. And it raises all kinds of psychological challenges, hurdles that become limiters and bottlenecks on what they can achieve.
Gena Gorlin:
And my field as a whole just isn't that interested in their problems. Because the way that the field identifies underserved populations typically is through the lens of what I call floor raising. Who's struggling the most, who is the most severely impaired? Which is incredibly important in its own right. And I want those problems solved as much as anyone. But it's only half the picture.
Gena Gorlin:
And I think in some ways it's the less fundamental half because ultimately what will better serve the millions of people who can't afford therapy, who are struggling to make ends meet, who don't have the kind of access we wish they would have to the currently still scarce set of resources that mental health can provide. The ultimate solution will be, it'll be technological, it will be creative, it will be top down and systemic. And who is going to drive those solutions? It's going to be the people who are out there doing the really hard stuff. It'll be the builders.
Gena Gorlin:
And so in a way I think that we've got to address the challenges that face the builders if we want to help anyone at all long term.
Jim O’Shaughnessy:
Yeah. I love the author, Robert Heinlein, who says throughout history poverty is the norm. And he says unless there's an extremely small minority, which I would in parentheses say, builders here, and then he goes on to say who are frequently despised and often driven out of society. The whole whenever some genius appears on the scene a confederacy of dunces aligns against him or her. Why do you think that is? Why do you think ... Because I think we see it in societies throughout history, it's not unique. We live in the United States, which some could argue is most arguably the most pro-builder society in human history almost. And still even with all of the-
Gena Gorlin:
Still for now.
Jim O’Shaughnessy:
Yeah, for now.
Gena Gorlin:
And here's hoping.
Jim O’Shaughnessy:
Yeah. But why do you think that is? Why do you think that there is this pernicious attitude that whether consciously or unconsciously opposes builders and creatives?
Gena Gorlin:
That's a great question. And a big question. So I think there are two elements in there, intimately interrelated. One element is that, and I write about this, I have a piece called Death is the Default, that I keep coming back to, and will probably write a part two at some point because it just looms so large in everything else I think about.
Gena Gorlin:
It's not the default to build and create and achieve and develop the virtues, the creativity, the tenacity, the discipline, the independent judgment to be able to conceive of new solutions and see them through. It's hard. It's chosen. And it's not just chosen once, it's a choice they make over and over every single day. And gradually you habituate to the traits of character that make that the more natural choice. But all of that needs to be built, and it doesn't happen by default.
Gena Gorlin:
And I would say for most human beings through most of history dating to the present day, it hasn't happened, or at least it hasn't consistently happened. And that brings me to the second element, which is ideology and culture. Ideology manifested and operationalized through culture and through systems of government and education and so on.
Gena Gorlin:
Given that it's not the default, it requires nurturance, it requires cultivation. And I don't think we've ever ... I think we came as close as we've ever come with the United States, the Constitution and the enlightenment culture that got codified for the most part by the founders of the United States of America, which is why I think what you said is true. That by and large America is still the friendliest to builders.
Gena Gorlin:
But I don't even think they quite went far enough or were consistent enough or fully understood what are the ideological, intellectual concomitants, what are the nutriments, what are the foundational principles that are both true and necessary in order to nurture and guide and liberate and empower human beings to build?
Gena Gorlin:
And we could spend the rest of this time just talking about what are those nutriments and what do I think was missing and what's needed today. But I think that's a huge part of it. I think that there's a whole moral foundation and an epistemological foundation that's needed.
Jim O’Shaughnessy:
Well, let's do that then. You say that the builder mindset needs to be applied across your life as a whole. Something I agree with implicitly. But explain for our listeners and viewers that ultimate yardstick. And why it's hard that the nutriments aren't readily available for people to take that kind of view. You talk about both the drill sergeant in your head and the Zen master in your head. But if you wouldn't mind, maybe enumerate some of what you see as missing.
Gena Gorlin:
Sure. Thank you. Yeah. So I think there are defaults that we see pop up across cultures, across eras of history that have attempted to provide guidance, attempted to answer some of the questions. That because we are agents, because we are conceptual beings, because we don't come with built-in instincts telling us here's how to survive as a human being, but we have to think and figure it out and learn how to do all of that. And so we need some form of guidance.
Gena Gorlin:
We have historically seen philosophical currents attempting to answer those questions, but I think in ways that have importantly fallen short of the total picture and the total human need. And one of those defaults really broadly is what I've summarized under this deliberately stereotype heading of the drill sergeant. And what I mean by that is the whole class of ideologies, perspectives, mindsets on which there's some authority, maybe it's God, maybe it's society, maybe it's your parents, depending on the kind of culture, upbringing, system that you're growing up in. But there's some external authority. Maybe it's just like the intrinsic good as defined by Immanuel Kant, a philosopher who tried to quote secularize moral philosophy, but still ended up with these categorical imperatives that just need to accept because of some really abstract, deductive logic that doesn't ultimately apply to you or your life in any personal way.
Gena Gorlin:
So whatever they are, there are these dictates, these authoritative standards that a human must uphold in order to something, in order to be good, in order to get permission and validation to then do what you want, to pursue happiness, to go about your life, to go about your day. Except that that day never comes because there's always more to do to appease that inner drill sergeant.
Gena Gorlin:
So if you think about Catholicism or if you think about socialism, the way that I grew up with in the former Soviet Union, in which there were also a whole bunch of shoulds and dictates of good behavior, don't be selfish, honor your parents and honor your community and be a good pioneer. There were two pictures in my first grade textbook of a good pioneer and a bad pioneer. That's a whole separate tangential story. But I distinctly recall being the bad pioneer very early on. And the pioneers were like the Soviet equivalent of Boy Scouts, Girl Scouts in the US, but less benevolent. Anyway.
Gena Gorlin:
So whatever that model that you're meant to live up to, to appease to, get permission from, it's like the test that you must pass in order to prove yourself a good person. That's what stands in for the guidance that we need in order to figure out who to be and what to do. Because again, something has to fill that void. We need that guidance. And we get it from somewhere, whether we figure it out for ourselves, which is so excruciatingly hard that maybe a few geniuses all through human history have managed that.
Gena Gorlin:
I think Frederick Douglass, born a slave, and somehow figured out how to teach himself how to read and sneak books and friendships into his extremely constrained life, and become an incredible builder and spokesperson for great ideas. But most of us are not going to be a Frederick Douglass. That's a very rare degree of human intellect and aptitude.
Gena Gorlin:
For most of us, we need guidance. And so we end up exposed to whatever drill sergeants are out in the ambient atmosphere. Be that from religion, be that from the ... it could even be like the entrepreneurial ethos, except that we drink it in the way that we learned to drink in whatever initial set of authoritarian standards we started with. And so we still end up treating it like a dogma. It's like thou shalt raise this amount by this point in the company's growth or else you're a failure.
Gena Gorlin:
It's like, well, who ... but is that actually ... do you need the money right now? And how is that going to serve your specific goals and your specific values and needs? Well, no, but Steve Jobs was already this far along by the time he was my age. Like, well, are you trying to live Steve Jobs's life or your own.
Gena Gorlin:
Right. Okay. So you've got the drill sergeant on the one side, and then the Zen master is I think the culture's answer to the drill sergeant, given that the drill sergeant has many clear disadvantages and costs. It sucks to be under the rule of a drill sergeant. We all know this. It sucks to be constantly yelled at and guilted and shamed and pushed along by fear and guilt and intimidation and this joyless existence where we're always trying to climb to the next hurdle just to then be looking ahead to the next one for the sake of what? So that we can feel a moment's relief that we're not a failure? It's terrible, it leads to burnout and anxiety and depression and just every form of misery.
Gena Gorlin:
And so then to try to cope with the tyranny of the drill sergeant, we're offered solutions like, look, you can't really control your outcomes past a certain point. Reality is it's a constant flux, it's messy. You can't control whether people will actually want your product. You can't control whether ... You can't control the weather. You can't predict whether you'll succeed or fail or hit any given milestone on schedule. Ultimately, you can't control what happens. But you can control your attitude. You can control your internal atmosphere. So focus on that. So this is stoicism and modern ... I call it Zen, but it's an umbrella term for a lot of different self-care and self-improvement culture approaches that ... And for most of my field, as I know it, where the focus really is on let's be kind to ourselves, let's lower the bar, let's not be so type A, so perfectionistic, so obsessed with achievement. That's just a recipe for disaster. Let's not define ourselves by our work. Let's really just focus on the moment, focus on what we can control, which is so little in the end.
Gena Gorlin:
And what my issue with that answer, with that cope is ultimately that it is a cope. And that what it doesn't do is radically rethink the whole perspective of the drill sergeant. Why is this even the standard? Why should I even be trying to get straight A's at Stanford or whatever it is that I'm ... What is that going to do for me? How will that serve me? What's the ultimate benchmark, the yardstick? As you mentioned. For what and for whom am I even trying to achieve this aim in the first place?
Gena Gorlin:
And that's where the drill sergeant ultimately just has no answer. It's like, for God, for the greater good versus ... It gets hand wavy the farther you go. Whereas I think what we need, and I have to tribute Rand, Ayn Rand, with a lot of the perspective background here on that, so maybe we can get spicy at least on that front because I know she raises a lot of eyebrows and a lot of questions. But she's got this unique perspective, at least from all the philosophy, psychology that I've encountered in the world, which is it's your life. Your life is the standard. Your life as a human being, your life fully lived, not just being comatose and on an IV drip, that's not a human life. That's not what we mean.
Gena Gorlin:
But the fully active and engaged and joyful and flourishing human life that you've got a shot at building during this one ticket that you've been given to existence. And where there's an alternative of this or nothing. You've been given this chance at something, and it's up to you what to make of it. So what do you want to make of it? That's the standard from my perspective. And again, I have to credit her work and the work of a lot of other scholars in that recent tradition for…
Jim O’Shaughnessy:
It also is very similar to William James's pragmatism for example, the greatest discovery of my era, I think he said, was that our thoughts can control outcomes and we can change them. And yet also I'm a fan of Taoism and some of the offshoots of Buddhism. And as I was reading Death as a Default, I came across Steve Hagen's Buddhism Plain and Simple, in which he takes a very different attitude. He says you are the final authority, not the Buddha, not the Bible, not the government, not mom and dad. You cannot ask others to bear responsibility for your life.
Gena Gorlin:
Wow.
Jim O’Shaughnessy:
He says the authority is yours and yours alone, and there is nothing you can do to get rid of it or shirk it or escape it.
Gena Gorlin:
Wow. Amen. Preach, preach, brother, preach. I love that.
Jim O’Shaughnessy:
So I mean, that's like when discussions get political, I basically say to people, the only thing that I really am is fiercely anti-authoritarian. And I think that one of the things that comes out of your work, at least that I took from it, is that it's not some grand conspiracy that societies have been run this way throughout history. It actually when you think about it makes a lot of sense. It makes a lot of sense that the people who are the elites running everything don't want a lot of high agency people mucking up their wonderful little society, their wonderful rule over all of the people. And they'll throw a bunch of ... everything with them is ought not is. It ought to be this way. It ought to be this. Not rather it is this way. And guess what? No one is coming to save you. And so I think it definitely comes down to high agency, as you yourself point out, but that can be really, really difficult. Early in my career, I basically found myself blaming somebody who worked for me about something. And then I had this Satori which was, no, no, it's not his fault. Ultimately everything is my fault. Now people said, "Well, that's crazy, what if somebody over here that is a colleague of yours really fucked something up?"
Gena Gorlin:
Yeah. Then don't be so hard on yourself. You'll be too stressed out if you just try to control everything. Exactly that mantra. And you're saying, "No, I'm responsible and I want to be responsible, I own this thing. And so it's on me to figure it out." Exactly. That's the high agency I'm talking about.
Gena Gorlin:
If I can just go back to your point that it makes sense that the ruling elite doesn't want too many high agency disruptors coming up and challenging their elite status. I think that speaks to a default that has existed in most places on Earth for most of human history. Which is the rule of men over men, or that's an outdated ... arguably, whatever, sexist way of putting it. Of humans over humans, the dog eat dog, someone is in power and someone is not, and it's a zero-sum game of who's going to get to hoard all the little bit of wealth that's been accumulated through the centuries, and then everybody else misses out on that little pie.
Gena Gorlin:
And the fundamental shift that happened I think with the Enlightenment, with the Industrial Revolution, with constitutional government, with the protection of individual rights, with liberation from slavery, the huge radical shift that's happened is that by and large people have been both constrained and liberated from ruling over each other. And instead have been set free to rule over nature, to actually grow the pie, to figure out how to build skyscrapers and develop medical technologies that extend our lifespan by decades and put artificial pacemakers into people, and grow and develop new forms of agriculture and new forms of distribution and division of labor. And let's not even get into the internet age and then the AI age that we're in now, and all of the new forms of creation, efficiency. Just the quality of life that it makes possible for everyone.
Gena Gorlin:
So that it's no longer, okay, well, rule or be ruled. It's what do you want to build? And how do you want to collaborate with all the other builders where everyone wins from everyone's work and contribution in a fully consistent realization of that vision.
Jim O’Shaughnessy:
And you make the point very persuasively that it does start with the Enlightenment, which was essentially, accept no one else's authority, find out for yourself. When they formed the Royal Society and the Enlightenment in the arts was happening in Florence under the Medicis, et cetera.
Jim O’Shaughnessy:
And yet those periods burned brightly, but they burn out. And is that just a fundamental flaw in human OS, human operating system, in that I'm a huge believer-
Gena Gorlin:
I hope not.
Jim O’Shaughnessy:
I do too. I'm a ... Again, back to Heinlein. He says most neuroses or psychoses are generally because of the unnecessary daily unhealthy habit of worrying about all of the troubles and sins of billions of people. In other words, I always say I try to find things to root for not against. It's very easy to root against things. It doesn't require a lot of imagination or skill, to poo-poo something is probably one of the easiest intellectual exercises out there. And yet ... And, I guess, I can't remember who's quote it is, but it's, most people think they're thinking when actually they're just rearranging their prejudices.
Gena Gorlin:
So good. Yeah. Or yeah, sometimes they call it emoting with words. What passes for thought, for a lot of us a lot of the time, rumination is a really ... My dissertation research, my PhD in clinical psychology was on rumination and how to combat unhelpful, unconstructive, depressive rumination. But rumination takes many forms, not just depressive, it can be anxious, it can be angry, it can even be quote positive rumination, where you're indulging in some fantasy that's detached from the world and from action. And it feels like thinking. It feels like I'm getting closer to some sort of insight.
Gena Gorlin:
And I think you're absolutely right that more often than not, it ends up being about tearing down and not building up. Because building is much, much harder as we've been...
Jim O’Shaughnessy:
I agree, I agree. And yet I also find it fascinating that ... This is best encapsulated in a Louis C.K. bit about the first time he was able to use Wi-Fi on an airplane, and he says-
Gena Gorlin:
I love this bit.
Jim O’Shaughnessy:
He said, " Yeah, I opened my computer, I'm on the internet, and I turned to my friend and I go, 'Can you believe this, we're 30,000 feet off the air and I'm surfing the internet?' And then it goes off, and I go, 'What the fuck.'"
Gena Gorlin:
"God damn it." Yeah. I love that bit. That bit sums up so much of the battle that I am embroiled in as it were. Yeah. And it's such a default. I mean, I think we all know it. We've all felt it. Now suddenly it's just part of the furniture of the universe. We now expect it. It's now our new default, our new normal. God dammit, why is the wifi network, it's like it's so easy to get entitled and just to forget that this all needed to be built. The default is forget wifi. There's no airplanes, there's no automobiles, there's no ways to, nevermind. There are no phones, there are no computers, there are no air conditioning. I mean, the things that we take for granted today, and we could go on a whole big, I could easily go in a long tear about this.
Gena Gorlin:
But yeah, the way that I raise my children who just are growing up with these robots you can talk to and ask any question, it'll answer the question. And it's just so wild that they're just going to drink that in as just part of the nature of reality, right? It's just like the world comes equipped with these machines that just are always listening to you ready to answer all your questions. Hey Siri, play Moana. Somebody had to build that and it could go away, and it's a lot of work. But that's represented in these parts of reality.
Jim O’Shaughnessy:
And I think that one of the challenges is both a lack of context like you're just bringing up, but also a deep ignorance about human history, right?
Gena Gorlin:
Yes. Crucially.
Jim O’Shaughnessy:
Essentially the vast majority of human history has been to quote Hobbes, "Nasty, brutal and short." In other words, human history, if you get a time machine, you do not want to go backwards, that's for sure. Because you can get a sliver in your hand from, I don't know, playing tennis on the White House lawn like Coolidge's son, and then die of sepsis because there are no antibiotics.
Gena Gorlin:
There are no antibiotics yet. Yeah, I mean just, yeah, or just basic sanitation practices. Soap, just the invention of soap and what a game changer that was, right? Yeah. Just so many things and people, the lack of knowledge of history I think is one of the major bottlenecks on our resilience and growth as a civilization for all the reasons that you're saying. And it's such a default when you don't have that context to just pine for the good old day. I mean, you see this everywhere in the media, you see on both sides of the political aisle, whatever the current scapegoat for all of our problems, be it social media, technology in general, or these profligate wokes who just, they don't appreciate when we used to have strict rules and morays and when you couldn't just get somebody pregnant. It's like on both. Do you know what it was like back then?
Gena Gorlin:
Do you know what you're pining for? Are you pining for, on the one hand, for an era in which if you happen to be born a slave, if you happen to be born a woman, if you happen to just you name it, then game over. And even if you're a member of the ruling elite of the, still no air conditioning, no cars, none of the things that would actually allow you to build upon that pot of gold you're sitting on. Do you know what I mean? Yeah. Just same thing on both sides. So much of what I hear, so much of the commentary and the doomerism and the catastrophizing about the future, I think partly it would be very quickly at least checked in a big way and the narrative would just change really quickly if people knew history.
Jim O’Shaughnessy:
Could not agree more. Because it is very illuminating that we really live, at least from my lights in the most wondrous age in human history. And you're talking about the accident of birth and sort of the Rawlsian theory of justice where you don't know what you're going to be born as, but you got to come up with the rules ahead of time. What rules are you going to promulgate that at least gets you thinking about, well, wait a minute, I could be born a slave. I could be born a member of a disadvantaged caste or whatever. But the other aspect of the idea is when you look at societies like the United States that are based on the rule of law, that are based on property rights, that are based on intellectual property as well, one of the things that you see is those societies advance much more quickly, not just in technology, but in societal norms.
Jim O’Shaughnessy:
So for example, I was born in 1960, I'm 64 years old. In 1971, when I was 11, my sister got married and had to go to court to keep her maiden name because the rules of society back then were that the woman took the husband's name. In the same year in 1971, women, married women could not get a credit card without their husband's permission. The list goes on and on and on. Gay marriage, all of the advances that have happened so rapidly, and I think mostly for the good.
Jim O’Shaughnessy:
In our society, I think one of the reasons for that is we are oriented toward the idea of stasis is bad. Change is good. Not all change is good, but guess what? You can fix the change if you screw it up the first time around. And one of the things that, again, it's just as a psychologist, this must fascinate you. Why is the default setting to focus on problems to hand ring, to look at the very things that are making our life easier? Things like antibiotics, iPhone, Zoom, all of those things, and not only dismiss them, but also say, and they're responsible for all of the problems we have today. I don't get that. I'm a huge fan of Julian Simon who looks at human ingenuity as being the ultimate resource. What do you think?
Gena Gorlin:
I mean, I resonate very strongly with that sentiment. So just to go back a little, I mean, I have so many thoughts on everything that you're raising. I'll try to insert some spice. Let's see if we can find those fault lines and then have fun duking it out. So to your point about Rawls, for example, since you mentioned, there's this common observation that I probably share with Rawls that, look, that the accident of birth should not dictate your fate, your future, this kind of idea of which gives rise to his veil of ignorance and to this idea that we should try to blindly re-conceive of the ideal society not knowing who will end up being within that society. But here too, you can see, okay, so what's the standard of the good? Remember we talked about there have been all these different drill sergeants through history, and we're trying to find the alternative to all these authoritarian standards.
Gena Gorlin:
Well, so when you try to conceive of the ideal society, say on Rawlsian picture of society in the world, you're thinking about this society as a whole. You're thinking about it's good for people to all have equal access to something, to resources. Where are those resources coming from? Let's bracket that. But they should all have access to resources. They should all have the same sort of general, they should have similar fates or similar opportunities. Okay, well what's good about that? And good for the sake of what and for whom and what are actually the preconditions of human flourishing such that we design a society where everybody has the maximum opportunity for flourishing. And I think where Rawls kind of ends up is actually with a pretty collectivistic picture of somehow it'll all sort itself out as long as we're all equal, as long as we're all held to, and ultimately we're all regulated, managed according in effect. I mean, he didn't explicitly say this, but I think it was part of the foundation from everyone according to their ability and to everyone according to their needs. And then-
Jim O’Shaughnessy:
That's Marx. That's Marxism, right?
Gena Gorlin:
It is Marx. That is absolutely Marx. Right. But I think that there are these common currents of thought where if you don't have an idea of it's the individual human being who's an agent who needs the freedom to build things, and then humans are going to build very different things. And some humans will go much farther than other humans according to their aptitude, their courage, their creativity, their potential, and a lot of accidents that will serendipitously allow some people to encounter investors who really love their vision and then they end up building something much earlier and scaling it faster than their peer over here who takes longer to sort things out or has to go through a period of fighting off depression first or whatever the case is. People are going to go at different paces, they're going to grow to very different points in life.
Gena Gorlin:
But if they're free to do that kind of growth, everyone is better off. Just my picture of the world versus no, we need to level the playing field, which is a kind of more Rawlsian perspective. And I think that that perspective has actually done a lot of the harm that has brought us to today where I think in wanting change, A, I don't think that we consistently within our culture value constructive change over stasis in the way that you were describing. I wish that were true. I do think it's still truer, relatively speaking in the US and in certain pockets of Europe and other parts of the world at various points in time as the cultural tides change. But I don't think it's consistently or kind of dominantly true.
Gena Gorlin:
I think there's a whole lot of desire for stasis that I see in the culture and a lot of, I think part of the problem is that there's still a kind of vacuum when it comes to for the sake of whom and what are we enacting the change, and who are the drivers? What is the mechanism of change? Is it society as a whole? Is it political innovation on the regulatory? What is the fundamental causal driver of good change, of constructive change? Because destruction is also a kind of change, superficially speaking, which will get me in a moment to your actual question about fear and destruction as a psychological default. But to have a positive vision, like a consistent, explicit, inspiring, positive vision that we can then teach and pass on and articulate to our children and our coworkers and our readers, I think we need a more explicit picture of the individual human being as both the causal agent of positive change, of progress and civilization and as the beneficiary of that change.
Gena Gorlin:
There's no such thing as a collective good. Society doesn't have a brain, society doesn't face the kinds of moral alternatives that individuals within that society face. Society is a collection of people, and there are mimetic cultural ideological processes, and there are systematic transmission mechanisms that make things much more likely to occur to each individual person and that make each individual person more likely to develop certain skills or not to have certain attitudes or not, but the people, the individual people are still the units of action and ultimately the units of either benefit or, anyway. And we could talk, it's tangential to my main expertise, which is within psychology, which we'll now get back to. But I just wanted to put that on our shared radar screen as like a background controversy that we could double click on.
Jim O’Shaughnessy:
Sure. And I actually think that you can take the premise of Rawls' veil of ignorance and still come up with a much better society than he did. And by that I mean if you make as one of your base rules that everyone has equality of opportunity as opposed to equality of outcome, that slight little shift changes things rather dramatically.
Gena Gorlin:
It really does.
Jim O’Shaughnessy:
And if one inculcates the almost hatred of taking a victim mentality and collapsing into learned helplessness as another guideline for that society, that society is looking pretty cool if you have those kind of as your base rules. But it also just strikes me as why do humans throughout history, invariably, I'm sure you're familiar with pessimist archives, right? Where they show whenever any innovation comes, there's always the people saying-
Gena Gorlin:
All the doomerism.
Jim O’Shaughnessy:
This is going bring the end of the world. This is going to-
Gena Gorlin:
Every time.
Jim O’Shaughnessy:
So I call it the cult of Malthus. And Malthus basically said that we're all going to die.
Gena Gorlin:
We're going to overpopulate.
Jim O’Shaughnessy:
Yeah, we're going to overpopulate. And again, that gets us back to Julian Simon, not if we have a bunch of humans who are very ingenious at coming up with solutions. And it puzzles me to no end why this is a dominant ideology even in countries like the United States. What do you think, psychologically speaking?
Gena Gorlin:
Good, thank you. So getting back to the kind individual psychological unit of analysis, which is where I'm best, where I'm most familiar, our fight or flight system, our flinching avoidance or escape of threat is the part of our psychological mechanism that we share with all the other mammals and animal kingdoms for which we evolve. And it doesn't take much understanding, vision, creative, context, historical perspective of the sort we were just talking about to flinch in fear from a stimulus that is vaguely unfamiliar from a stimulus that we aren't quite sure what intentions it has for us or what to do with, right? It's the most basic. Babies have it already, right? It's like babies will cry at loud noises and will flinch from certain kinds of sudden threatening movements.
Gena Gorlin:
And what we can build on top of that is thanks to this incredible cognitive apparatus, this higher order reasoning apparatus that we come equipped with is a conception of future, a conception of higher order goals toward which we can strive and build, where we can imagine causal relationships among events and actions that haven't yet occurred and we can then act upon what Aristotle called final cause, the conception of an end. And we can choose those ends, we can make them up and then we can rearrange reality in order to enact them.
Gena Gorlin:
But all of that has to be figured out. It has to be built. It's conscious, voluntary thought that depends on the thinking we've done to date and depends on to be able to see into the future more than as I watch my kids grow up, I have a one-year-old and a four-year-old, and seeing my four-year old's sense of time gradually stretch from a minute from now to an hour to a day to a week now, she can even look forward to something that's going to happen in a month. For over a month, we were looking forward to the day we would go to Disneyland. And I could actually reason with her about, look, we're going to get a chance to try this type of candy when we get to Disneyland. And so if you do all the things now that will help us get packed and ready to go, this will be part of the reward. We will get to have this experience.
Gena Gorlin:
But to get there, she already needs to have formed a whole bunch of pretty sophisticated concepts of places that people have designed for children to enjoy, to even be able to have that kind, to be able to imagine something. She's seen pictures of the castle and of the characters, but to understand there are imaginary characters who are different from real people and about whom we have these shared stories that we tell. And at this magical place called Disneyland, there are people dressed up in costumes who are pretending to be those characters. There's so much knowledge and every time she thinks about it, she's got to be able to marshal all that knowledge and call upon the conceptual framework, the schema that she's built to date. But it's so easy to lose sight of all that, especially if she's tired, if she's cranky, if she's upset about something and just get so unconsolably distraught over the fact that she thought she'd get two bananas and she can only have one, whatever it is in the moment, or wait, what mommy's not going to do bedtime tonight? The thing right in front of her that gets her upset. And then I see that conceptual system kind of shut off and she goes into default mode, she goes into autopilot and okay, all bets are off. There's no context, there's no putting things in perspective, there's no delayed gratification. It's just bad, bad, bad. I want this and I can't have it now.
Gena Gorlin:
And I feel like that's such a useful model for then thinking about as adults, when we get on about the latest social media development that somehow induces panic in us and we just latch onto the latest, the latest threat, the latest new unfamiliar thing, and we just let our fight or flight response run away with itself. It's a default and it's easy and it will kick in to the extent that we're not really taking ownership of our thought processes, which gets harder and harder the more sophisticated they get.
Gena Gorlin:
So as adults, and sometimes it's not just hard from an effortful standpoint, but also it might be really painful, scary to the extent that part of what we would need to grapple was like, so wait, my whole political worldview might be wrong? Or so wait, but does this mean I have to disagree with all my friends about, does this mean I don't even understand this issue? Am I going to get ostracized by all my colleagues because now suddenly I'm asking the wrong question about climate change, or I'm daring to raise a flag that like, wait, but maybe we could use this technology in some way that actually students could benefit. What if it could aid their learning? Am I going to just be a pariah who gets laughed at? It gets so much easier just to go along with the crowd and just to be mad about everything.
Gena Gorlin:
And so I think that same fight or flight response, it's always there as a default and it kicks in the moment that we forget to or sort of semi intentionally renege on that conscious control of our thinking.
Jim O’Shaughnessy:
So we increasingly see larger and larger groups of people having to stay in the theme of your daughter, continual toddler tantrums about much of what they see in the world. To the fight or flight, I would add another F, and that is freeze. I think that human operating system, human OS is basically driven by emotions. And I think that the king of the emotions that drive it is fear, specifically fear of new things, novel fears. And what-
Gena Gorlin:
Yeah. So can I add my own small detail that I would say all of that is true by default. I would say that by default we are driven by fear, but I don't think that it's our only option. But yes, please go...
Jim O’Shaughnessy:
And you have nicely seguewayed to the question that I was going to ask, which is you say that builders are not born, they're made. So walk me through that. If we assume that we're right, and of course we could be wrong, I could be totally full of shit here. But if we assume that we're right and that human nature is governed by emotions, the governing emotion, the one that will rule all of them is fear, how do you work with people and create builders as opposed to another school of thought is that they're born not made?
Gena Gorlin:
Yeah. So I think it's really, really important to differentiate my perspective here a little bit because I think it's actually a really dominant and very reasonable default perspective to see human behavior through the lens of fear and avoidance. And much of it in fact is fear motivated, and we see it everywhere. And what I think then happens is that we generalize from this default. And I think much of my field, much of psychological research, it describes how humans behave by default. Because you collect a bunch of college students from Psych 101 typically, and you run the same study on them where you get them to lie to themselves or lie to the researcher, or you put them in a state of dissonance or conflict and then they make up some BS story to relieve their conflict and not have to feel bad anymore. And then you say, see, here's human nature. We're fear driven. We're just constantly trying to feel good about ourselves and feel safe.
Gena Gorlin:
And I think the problem with that inference is that we're inferring from a default to norm and to an optimal state of affairs versus realizing that we aren't constrained by our defaults. The unique thing about human beings, about human nature in my view is that we have agency. And part of what that means is we have the agency to build motivations for ourselves and actually feel and be excited for and understand in a really visceral way and pursue positive visions for what we want to build, for who we want to be, for what experiences we want to have. And actually that's an alternative to being driven by fear. We can be driven by love, and that's fundamentally different and not just different. It's actually more the distinctly human way to live.
Gena Gorlin:
It's the ideal, but also I would say it's the norm in the sense of healthy human functioning is to be moving toward things, is to be anticipating and excitedly awaiting, but also acting to bring about things. And coming back to my example of the four-year-old when thinking about Disneyland and when anticipating all the exciting things she's going to do, she's not fear-driven in all those moments. She's very much, she's like building a conception of what that day will be like. And then when we were there, it was really interesting to see how fear and curiosity, fear and love, excitement valuing played together within her soul.
Gena Gorlin:
Because for example, she got really scared of the first ride we went on, the Snow White ride because this really creepy robot queen who makes the poison apple. And then you see the apple squirming around with deadly worms inside and you see all these ghouls. And she didn't expect it to be that scary and I didn't prep her for it. I didn't remember what the ride would like. And afterwards she said, "Okay, no more bad guys. I don't want to go on rides with bad guys." And then we ended up going on It's a Small World three times, partly because sure, no bad guys, but out of all the rides without bad guys, she specifically preferred that ride because she really liked the song and she really liked the dolls and the colors and the variety of different animals that she could name and recognize, which is nothing to do with fear. It's very much about her interests, which are developing in pretty distinctive ways and the things that she resonates with.
Gena Gorlin:
And then she worked through her fear toward the end of the day by putting into perspective, wait, these are dolls. So they're not, she asked me questions like, "Mommy, can the dolls see us?" No, sweetie, the dolls are not alive. They can't see anything, they can't hear anything. "Oh, okay, are the bad guys real?" She asked me a whole bunch of questions to put it into perspective, and then she chose to go on the pirates ride, which I'd been selling to her the whole day because come on, this one really cool ride we've got to go on. And then she went on it and she loved it. And she said, "Mommy, that wasn't actually scary. The bad guys they're actually mostly good guys."
Gena Gorlin:
And she had so many things to say about, that's not fear-based motivation. Love won out over fear for her that day. And my hope for her in her life is that that continues to be her norm. That she works through the fears and ultimately she forms and moves toward interests and curiosities that drive her forward, and that's the real motivational thrust of her life. Does this answer your original question? I feel like I…
Jim O’Shaughnessy:
No, that's okay because I am still perplexed. By the way, I agree 100% with you. As I said earlier, everything that I try to work on or create is something I'm rooting for, not something I'm rooting against. And I kind of think that the opposite of courage is cowardice, it's conformity. Essentially, Anaïs Nin's great quote, "Life shrinks or expands in proportion to one's courage." And again, another favorite of mine, Terence McKenna, "Nature loves courage. Dream the impossible dream and the world will not grind you under."
Jim O’Shaughnessy:
So I subscribe to all of those maxims, but I'm wondering around the question of are builders born or are they made? And I know that you have a specific way that you address helping make builders, and I'd like you to go through that with me.
Gena Gorlin:
Thank you. Yes, thank you for bringing me back to the main target. So I think that they're made in a few different senses, but the most important one being you've got to learn how to be courageous. The thing that you were just describing. Courage is not just like you flip on a switch. Courage requires there's a reason to be courageous and to be able to conceive of a reason and to be able to hold on to that reason against all the resistance of your own fears, all the resistance of people's disagreement and opposition to you. You actually, you've got to have developed virtues and also knowledge that allows you to see into the future, allows you to imagine real plausible, credible, credible to your own mind, and actually credible in reality possibilities. And that you distinguish from fantasies, because it's also easy to courageously jump off a ledge that actually will just kill you.
Gena Gorlin:
And plenty of people have done plenty of quote, unquote, "courageous", but actually just impulsive self-destructive things, and to be able to tell the difference, like, no, I have a scientific basis for believing that actually what looks like a 50-foot drop, because I have this thing I've created that is a parachute, and I've tested it out and I've done simulations on it, and I understand the physical mechanics of the, I am not going to be able to describe it competently, like the way that the air will push back on gravity. Because I understand all that, I am jumping. I'm making an informed choice based on independent judgment that I can trust in that actually I'm not going to fall, I'm going to float, or I'm going to be able to get places faster because I've invented this new form of travel.
Gena Gorlin:
And boy has there been a lot of work, a lot of disciplined iteration through mistakes and failures and a lot of building of mental models, all of which for which I've needed to be able to do things like wait, do things like make causal connections and form complex first principles, judgments that I couldn't check my work against somebody else's answer key, because I'm the first one who's figuring this out, or because people disagree with me. So at the end of the day, I've got to make the call whether this is at least a plausible hypothesis, a risk worth taking, and I've done the due diligence to check it against reality. I've done customer development, I've talked to people, I know this is a real problem, so I'm willing to put my money where my mouth is.
Gena Gorlin:
There's so much skill and so much what I think is virtue because it's skill combined with the kind of characterological motivations and commitments that we build over time by doing disciplined, goal-directed work where you've built up courage, you've built up grit, you've built up what I call self-honesty, which is I think one of the fundamental virtues that we need in order to build anything ambitious and great. We've built up epistemic skills and toolkits for checking our biases, for having the kind of self-awareness to realize that there are things we know and things we don't know, and that we know things at different levels of certainty, and there's probabilistic knowledge and then there's first principles knowledge, and that those are different.
Gena Gorlin:
And there's what we can see, and then there's what we infer. And none of that comes built in. So a lot of the work should be done through education, and I don't think today really is being done well through kind of standard education. And that's where my husband kind of picks up the mantle. He's the educator in our family and is writing a book on, I think I'm allowed to say this publicly, on what he calls the new normal. Kind of how to educate healthy, competent, virtuous adults in effect. And then my work, since I mainly work with adult builders and founders, is in some cases, build the foundations that didn't get built the first time around because I don't think we have great educational systems and tools in place to help children develop those skill sets in the first place. And then also to strengthen and provide more scaffolding on just how courageous are you able to be?
Gena Gorlin:
Just how big a risk can you take without going off the rails and becoming impulsive? Just kind of how well are you able to keep a long-range, complex, uncertain vision clear enough in your mind that it can continue to motivate you instead of just defaulting into fear mode, at which point you're just going to burn out. And not only can you make it clear to yourself, but you can communicate it to your team, to your investors, to other stakeholders, to all the other people that you need to have on the journey with you. And can you have the hard conversations and can you hold people to high standards? So there's so much knowledge and skill that's needed in order to achieve great things as a builder. And that scales all the way up and down. Whether what you want to build is you want to be a really good waitress or waiter, which requires a whole lot of discipline, skill, honesty, respect for your customers, multitasking, just so much that goes into doing that work well and just love of work, respect for work all the way up through building a globally impactful company.
Jim O’Shaughnessy:
So I'm still intrigued by the idea of being able to build a builder. So you're working with builders, obviously, you're working with entrepreneurs, you're working with people who are what I would call a self-selected sample, i.e., you're already working with people who took the plunge, so to speak.
Gena Gorlin:
Yeah, that's right.
Jim O’Shaughnessy:
And there's actually a theory about America that is in an otherwise forgettable book called The Hypomanic Edge, and the author makes, the author makes the argument that the reason that America has different DNA almost than other countries is because think about the people who came here. These are people who left everything they knew. They left their family, their homeland, everything, all the support structures, et cetera that were in place and said, "You know what? Fuck it. I'm going to America and I'm going to build things and I'm going to do my own thing." And that, in my opinion, defined America right up until maybe post World War Two. I mean, for example, the guy who did Mount Rushmore, he didn't ask for anybody's permission. In fact, Coolidge-
Gena Gorlin:
This is [inaudible 01:07:26].
Jim O’Shaughnessy:
Yeah, when Coolidge was president, they're like, "Hey, there's this guy doing this incredible, you should check it out and cool." Coolidge is like, "Cool." So he walks up, looks at it, and he goes, "Wow, cool. What gave you the idea?" Without any sense of, "You can't do that. You need 10 years of approval-"
Gena Gorlin:
Permits and you need... Seriously.
Jim O’Shaughnessy:
"You need permit and all that." And I bring that point up, because we built the Empire State Building in, what? 18 months. And then-
Gena Gorlin:
The Golden Gate Bridge, which engineers thought literally was impossible, physically impossible, and then there it stands.
Jim O’Shaughnessy:
Same with the Brooklyn Bridge and physically impossible-
Gena Gorlin:
So many.
Jim O’Shaughnessy:
All of those things. And this was kind of a playground, if you will, for misfits as I call them. In other words, people-
Gena Gorlin:
I'm one of them.
Jim O’Shaughnessy:
Me too, me too.
Gena Gorlin:
As an immigrant. And immigrants, we know statistically, immigrants are overrepresented among entrepreneurs.
Jim O’Shaughnessy:
Absolutely. To be clear, I'm not an immigrant. Our family has been in America since 1830, whatever. But yes-
Gena Gorlin:
But in spirit.
Jim O’Shaughnessy:
Yeah, I used to joke that what we ought to do is just take all of the people in the former Soviet Republics and move them to America, because oh my God, it would be-
Gena Gorlin:
So I'm one of those imports, and yes-
Jim O’Shaughnessy:
I know you are. I know you are.
Gena Gorlin:
We'd be so much better off, and we can go on a whole tangent about that. But, yeah.
Jim O’Shaughnessy:
I have never met a person who lived under authoritarian or totalitarian rule who was in any way favorably disposed towards tons of rules and regulations trying to inhibit people's ability to create and do things. But so-
Gena Gorlin:
Yeah, although-
Jim O’Shaughnessy:
Please.
Gena Gorlin:
Sorry, important caveat, you're looking at the people who chose to leave and to come here, which is a very important caveat because in fact, as I think about if we just imported the whole population, which I think anyone who wants to come here should in fact just be allowed to come here. And I think it should be a very simple, minimal, it's like, let's make sure you're not a convicted criminal, and that's it. Come, please be one of us. Build, join the smelting pot that it once was. If we were to make people come here who have contented themselves with living under authoritarian rule, we would find a very different kind of mindset, unfortunately, and it's quite-
Jim O’Shaughnessy:
That is an excellent qualification. Yes, let them come, not force them. I'm not a fan, I don't want power over any other individual in terms of compelling them. You can compel anyone at the point of a gun to do something. That is not true power-
Gena Gorlin:
It's not the American spirit anyway, indeed.
Jim O’Shaughnessy:
Definitely not in the American spirit. But the challenge that I'm still kind of facing on this, is it nature or nurture? It's probably a combination of both.
Gena Gorlin:
Yeah, happy to-
Jim O’Shaughnessy:
So you're working with a self-selected sample. In other words, people who pop their heads up and are like, you know what? I've only got one life, and rather than worry about it and how broken I am and how bad I am and how horrible I am, I'm going to focus on making my life fucking awesome, which I love that part of what you write about, because so few people actually do that. But you also talk about the perfect personality for people attempting to build. Obviously, the ingredients would seem obvious, but I run into so many people where they just don't get it at all. So high agency, it's like George Mack, who's a friend of mine I've had on the podcast a few times, basically says, if you want to know who has high agency, do this thought experiment, you are imprisoned in a third world nation's jail system. You get one call, who are you going to call to get you out of there?
Gena Gorlin:
Ooh, that's awesome. Yeah, and I like what I've seen of his work, and I follow him on Twitter, but that's a fantastic heuristic. Yeah, who are you going to call? Who do you know is going to figure out a way, they're going to figure it out?
Jim O’Shaughnessy:
Yeah.
Gena Gorlin:
Who can you count on?
Jim O’Shaughnessy:
And so high agency, courage, imagination, positive sum attitude. I mean, these are all, for example, O'Shaughnessy Ventures, we built it with one north star, and that is positive sum outcomes, no matter what vertical we're looking at, be it our film division, our book division, our venture division, any of that, we only will play positive sum games. And people say, "Well, yeah. Oh, okay, but have you ever turned down a sure thing?" Well, first off, there are no sure things.
Gena Gorlin:
Yes. And also what sure thing? And yeah, indeed. That is not a sure thing.
Jim O’Shaughnessy:
But the answer is, having that as a north star really does change your behavior in many ways. So for example, in our venture division, we've seen decks where we know, oh man, they're going to make a lot of money. Things like payday lenders, we will not put a dime in a payday lender because they're predatory and they're negative sum games. And so we resist the urge to say, oh, wow, this is going to just rain the dollars and keep the powder dry for positive sum things. But again, my question is for you, let's talk a little bit about your idea of zenion, the misunderstanding, you have a very nuanced understanding of the perfectionist verse, as most people take it, versus what your version is. So if you wouldn't mind.
Gena Gorlin:
Yeah. So this is where that drill sergeant/zen master dichotomy comes in handy for me again in my thinking where I think we have these default understandings of what it means to be ambitious, what it means to strive for excellence. And a lot of it has gotten packaged together with those authoritarian drill sergeant standards that take the agency actually out of our hands where we don't have agency over what outcomes we even choose to pursue, what matters to us on those kind of drill sergeant mindsets. And so perfectionism becomes inherently pathological because it's like trying to appease your inner drill sergeant by dotting every I and crossing every T when actually what's important is just to send out the damn email now before the ship and the investor goes with somebody else or whatever. Actually do the thing or ship the product, get some feedback from customers on this first iteration.
Gena Gorlin:
They don't care if it's shiny, they want to see if it works, you want to know if it works. And so quit procrastinating by futzing over the design of your title slide and actually ship the thing. And the issue there is that the standards we're pursuing, the quote, "excellence" that we're trying to, the bar to which we're holding ourselves is ultimately arbitrary. It's whether it's based on the expectations of others, whether it's based on just our fear driven avoidance of risks, uncertainty, judgment, or even just action. Often that we're avoiding putting ourselves out there.
Gena Gorlin:
And because we have all these inertial kind of templates available to us in the culture to substitute for the real pursuit of excellence on our own terms, it's really easy to like, well, I need to make my pitch deck look as pretty as this template, that literal template I've received from this really prestigious serial founder or whatever. Or my VCs said they needed these three things, so I'm going to try to check those exact three things off the list instead of explaining to them why the third thing actually isn't relevant to us or why there's a better way to frame the information they're seeking.
Gena Gorlin:
And so what I see so often what happens when we push back on that kind of quote, "perfectionism" is we throw out the baby with the bathwater and that we just generally lower the bar. We say like, "Oh, we can't really control who's going to invest in us, so we'll just send this shoddy, half-assed deck and we won't work too hard to actually clarify our business model." Where you're kind of missing the point. Focus on the important things and actually really do the important things well and actually really aim for the highest heights and be ambitious and strive for excellence. Get the stuff right that matters, and use your own judgment, your own standards for what matters, which is not just arbitrary feeling based judgment, it's based on reality and your really disciplined, rigorous mental model building as you engage with reality and learn about your customer, learn about the market, learn about the technology.
Gena Gorlin:
And so one of the things that I think differentiates those self-selected founders, builders who come to me for coaching is that what they've chosen to do, it's such that it's sort of easier to peel back the scaffolding of whatever BS standards are in their heads of like, well, “this is the right way to pitch a VC,” or “this is the right number of people to hire at this stage in my...” To kind of peel it back and say, "Why? Why are you doing that?" And ultimately, either they have their own reasons in terms of their mission and the solution that they have proposed to their problem and their thesis about how is this actually, what are you building that people want? How do you know people want it? And what's your go-to market? Either they have actually thought it through and have their own fresh original answers since they're trying to do something new, so the answers aren't going to come from a book. They're not going to come from any other story.
Gena Gorlin:
Either they have answers or it's very apparent when they don't. It's very apparent when it's like, because how other founders do it or because it's really scary to fire people. When it comes down to just, yeah, “no, I'm just scared and I don't know the better way.” Or “I don't want to take the plunge or the risk.” Why? Have you thought through the upside relative to what is the cost and what is it... “Yeah, the upside is a little bit hazy to me, actually. I kind of get in principle that there's infinite upside if this can actually scale. But I don't know how to make that real to myself. I don't really believe in... I've never done it before, so how can I know that I'll do it?” Okay, well, let's actually look at the qualities you bring. Let's look at other examples of founders who have succeeded at bringing a similar product market, and let's actually extract principles that you can understand for yourself.
Gena Gorlin:
Here's the kind of course of action that leads to this kind of success. And also, it's stochastic, it's iterative. I'm probably going to have to try a few times and yeah, I might fail, but here's the nature of the upside if I succeed. Now I see it for myself. Now I can sell it to VCs, to future team members, to a co-founder, to whatever the stakeholders. So it's sort of like it brings us face to face with the reality that I think every human being actually faces, but most human beings are more insulated from it, because they're going to work for some institution where everything's already been codified and they're just told to do it this way.
Gena Gorlin:
And so it's really easy to just default to, I guess this is how it's done, this is how it's always been done. It's easy to be low agency in most contexts where people find themselves, whereas it just doesn't work. If you've chosen to be a founder. It's like you have to have agency. You're not going to get anywhere. It's not going to build itself, it will just die. That is the actual default. The thing dies if you step away and stop building it.
Jim O’Shaughnessy:
The other trend that I am baffled by, which is confusing activity with effectiveness and this onslaught of busyness, busy work. Which seems to me to be like, I don't know whether you've ever seen the movie Office Space. I think it's really funny. I think one of the lines there is, " I'm pretending to work just because pretending to pay me." And the cynicism and default assumption of like, yeah, because that's the way it's always been done, or my boss said that. So I am fascinated by this smaller group that do exhibit high agency, that do focus on creating things that make the world a better place, that are agile enough to recognize their mistakes and pivot and or say, "Ooh, really fucked that one up."
Jim O’Shaughnessy:
I look at mistakes as portals of opportunity to learn. And I just think that's the other thing. Tell me how, so I'm going to be your client now. I'm an entrepreneur and I come to you and I've got great ideas. I've got all of this, but you interviewed the other members on my team. This is not true. For all of my teammates at O'Shaughnessy Ventures, this is not true. I'm using this as a hypothetical, but you find that I have a bunch of actually B and C players working for me.
Gena Gorlin:
How did you know that this has been every founder conversation that I've... So most of the founder conversations I've had, so don't assume any given client listening to this that I'm talking about you, unless we've already discussed it, which probably we have, in which case it's a known quantity, but an overwhelming majority of founders I've been working with, this is the issue. It's one of the issues, if not the issue. It's just like this slip toward mediocrity. Anyway, please go on back into the role play.
Jim O’Shaughnessy:
So my question for you is, why? Why did I do this? Because I want to know why, but then I also want to know how do I correct it?
Gena Gorlin:
Yes, yes. So founder that I've gotten to know a little bit, it sounds like you've gotten to this place because of whatever mental models you've brought to the hiring process in the first place that I'd like to understand better with you. Because I imagine that when you made each of these individual, you thought you were making a good call, and I wonder if we can shed light on some of the maybe less than fully explicit background assumptions that made these hires seem like either the right call or the only call. So we would maybe zoom in like, give me your worst performer right now, or based on my conversations, this person seems like he's a C. Tell me the story. A, how'd you hire him? Why'd you hire him? Why is he still here?
Gena Gorlin:
And if we fast-forward a little bit in the conversation, okay, so it kind of sounds like in the first place you kind of rushed the hire, maybe partly because you felt like you couldn't get anybody better. You felt like the 10X engineers wouldn't talk to you because you'd already hired a bunch of more middling engineers, which you had done. You felt like, well, you don't really have a network and who would want... And also it's like you can't have such crazy high standards for... Not everyone... If they're not going to be a founder themselves, it's probably because they need a little more holding. And so you probably made a bunch of excuses for these kind of more middling performers.
Gena Gorlin:
And if we really peel away the onions, you kind of have a mental model of people that's pretty cynical. You have a pretty low expectation. You really aren't holding out much hope that A, these people could level up if you actually held them to higher standards. You're scared of them. You're scared that they'll leave. You're scared. There'll be some sort of mass protest. You're scared that now they'll poison the well and nobody will ever want to work for you. And then as a result, you go easy on them, you baby them. You kind of just let slip each missed OKR and you can just keep moving the goalposts lower and later. And next thing you know, there's resentment on both sides. Next thing you know, it is actually really hard to hire great people because great people don't want to work with mediocre people.
Gena Gorlin:
And then if you've got the middle management layer, like they're hiring as we know, B players. And so you are really in a pickle here. And the first thing we're going to have to check, the first thing we're going to have to challenge is this assumption that there's no one better out there for you. We're going to have to figure out where did this come from? This scarcity mindset about people, because I just keep seeing this everywhere, this idea. And if we look back far enough, yeah, you probably, in whatever random neighborhood and school you got thrown into as a kid, you probably were exceptional. Most people probably did kind of suck. And/or the few that were also really bright, ambitious, agential were all probably sitting in their parents' basements on their computers and not knowing how to socialize or talk to the couple of other peers who might turn out to actually be really interesting.
Gena Gorlin:
And so all of you were sitting there in the isolation of your rooms thinking you're alone in the world, and you grew up still kind of believing that deep down. And also, you have this whole mental narrative about how, oh, well, it's just I am so antisocial and I'm so obsessive, and I'm this, to come back to the hypomanic thing. I am the weirdo. Something's wrong with me. So I just have to accept most people aren't like me. I live in a world of normies who like, yeah, they're just not going to work that hard. And I just have to be okay with that because normal people don't work that hard. Normal people don't drive themselves like I do. And you've thrown yourself under the bus to kind of feel like at least maybe you can take some ownership then of that. But the result is that you have cut yourself off from the community of people who actually would see you and the community of people who would actually level you up.
Jim O’Shaughnessy:
How do you help that founder to figure out, oh, I'm selling myself short here, and then what course of action do you recommend he or she take to correct that?
Gena Gorlin:
Yeah, so to the first question, we often start from a place of “I'm not managing people well,” or “we are not hitting our targets, and we're not going as fast as I would like us to go, as we could be going. Competitors are starting to catch up, or we're going to run out of money.” Whatever the case may be, there are objective metrics that are not getting hit that could spell the doom of the company, and we start to diagnose, like where are the bottlenecks? What's going wrong? And it very quickly ends up, we zero in on, okay, so your engineers are not moving as fast as you'd like them to be moving, and why aren't they? And well, they're not actually, they're heading home at 5:00, even though I've always modeled working until the job was done for the day. Are they really showing up and taking ownership? They're not really taking that much ownership. They're not really hitting their individual and team OKRs and well, why is that? What's going on? How do you manage those performance issues?
Gena Gorlin:
Well, I've got this, my CTO, whom I hired, he's not a co-founder, he's got a softer, gentler approach, and he tries to keep people motivated and to keep up the morale and, okay, so what's the conversation when they don't hit their performance targets and when the team is missing deadlines? Well, you know what? Yeah, I don't really think he's that clear on the deadlines. Or, oh, yeah, they just moved the deadlines out a little bit. Well, what's up with that? And why is that allowed to happen? What's your conversation with... What are your one-on-ones with this manager or this team lead, whatever?
Gena Gorlin:
And usually that's where I hear a lot of pent-up frustration. Yeah, there's a whole history there of, we've had a few different blowouts where I tried to ratchet things up. I tried to give tough feedback, have the tough conversations, and then he felt attacked, or there was resentment or, okay, so let's go back to, was he better at one time and then somehow slipped into this more low-agency, mediocre performance? Well, no, actually, there were probably red flags at the point where we made this hire.
Gena Gorlin:
Or there's some story, and then the story repeats across a few different key personnel where I thought this was the best I could get, or I was scared, or assumed that it would be fruitless to approach the 10x engineer whom I had been following online, but of course, he's going to get snatched up by Google. Or of course they'll get snatched up by one of these sexier startups, and I'm just a first-time founder, and why wouldn't he even give me time? Like, well, but did you talk to him? Or, well, I talked to him, but I was a little bit hedging about it. Okay, well, what was your sell? What was your pitch? Is this going to be the best place in the world for this guy to work where you're going to hold the high bar and you'll all be doing the best work of your lives, like at Apple at the height of its glory?
Gena Gorlin:
But yeah, I already have these other three engineers, of whom two probably need to be fired, but haven't been yet. And okay, we're seeing a pattern here. So usually that's how the diagnostic conversation goes, and sometimes it's a short thirty-minute assessment, sometimes it comes out over a couple sessions, and if we're working on something else as a primary focus. Okay, now what are we going to do about it? And that's where it's a two pronged approach. Leveling up, raising the bar internally, and raising the bar on how aggressively you network and source and recruit extra. And both of these campaigns really have to stem from a common underlying shift, from that scarcity mindset about people, to an abundance mindset about people.
Gena Gorlin:
And sometimes before founders are even willing to start taking baby steps, first we really have to do some reflecting together on, what is the evidence? What informed this mental model for you of everyone sucks but me, or I can't get anyone better, and so I have to settle, I just have to somehow make it work with mediocrities? Where's it coming from? What's our data? And what contrary evidence have you in fact encountered as an adult that could really shake up this model for you if you consciously assimilate it? Like, okay, yeah, I've been through YC where I had really interesting conversations with Garry Tan and Paul Graham and Jim O'Shaughnessy, and I've had people actually seem interested in what I have to say, and I have these incredible interactions with, and sometimes they'll come to me for advice, but no way that any of them would actually want to work for me.
Gena Gorlin:
Why are we assuming that? And there's so many other areas in which you're not willing to just make unchecked assumptions like that, and you're really rigorous about the hypothesis testing, so can we bring that same mentality to this notion, to this implicit cynicism, implicit pessimism that you formed about people? At least don't knock it until you try it. Go, send a cold DM to Garry Tan, see what happens. Half the time, you'll be surprised, or to whatever 10x engineer impresses you the most, and make a hard sell. Offer them a higher salary and more equity than whatever you've been assuming to be the standard package because you need to shake things up. This is the absolute number one priority right now if you don't want to die. So where else are you going to put that capital that could possibly matter more than really turning the tide on the quality of your team?
Gena Gorlin:
And then be willing to start setting standards and shake things up. Sometimes I'll really work with a founder to do a shake up as soon as they're willing to do it. We're going to have an all hands where, okay, guys, I've been working with my executive coach and I've realized that I've let things slip a little bit. We're going to be doing things differently from now on. So here's the deal. And some of you, you're not going to like it, that's okay. I know not everybody's going to want to be on this ship. If it's not for you, if you need work-life balance, whatever, we're going to make you a generous severance package, I'm going to help you find your next gig, you just let me know.
Gena Gorlin:
But if you're on the ship, here's going to be the deal. We're not missing deadlines anymore. We're going to have daily stand-ups where you're going to tell me what you got done and how you're owning your outcomes for the end of the week, for the end of the quarter. This is how we're going to be doing things. This is going to become the toughest place and the best place we've ever worked. Are you in or you're out? And just really holding that bar, but from a place of inspiration, from a place of, do you want this to be the most memorable experience of people's lives, who got to work with you on this company? Or is it just going to be another job? So those are some of the-
Jim O’Shaughnessy:
Yeah, I love it because I've always operated under the assumption that you can't tell until you ask. And it baffles me that I've had conversations with people who I view as incredibly gifted, incredibly smart, incredibly, all of the above. And then I'm just waiting. So ask me, ask me, "Jim, will you invest in my company? Jim, will you make this movie? Jim, will you publish my book?" And we don't just do it.
Gena Gorlin:
I hope that everyone I've coached is listening right now to this portion of the episode. Really just ask. You might be surprised.
Jim O’Shaughnessy:
It's like you can't tell until you ask. And if you think probabilistically, it's like, hey, one of the things that I often say is we are deterministic thinkers living in a probabilistic world. Hilarity or tragedy often ensue, right? Who's going to be the home run king? The guy who gets the most times at bat and is a good hitter, and just doesn't quit. "Oh, I got up three times and I struck out all three times. That's it. I'm never playing that game again." And it's just, that's so whingy and whiny.
Gena Gorlin:
Yeah. And do you know how probability works? A sample of three tells you nothing, nothing at all, about any predictive trends that you could say anything meaningful about. Yeah, we see this in dating and we see it in certainly every aspect of the VC founder relationship, just people making strong inferences based on really small sample sizes.
Jim O’Shaughnessy:
Which is crazy.
Gena Gorlin:
Crazy.
Jim O’Shaughnessy:
And the idea that you just, to not understand that persistence is a requirement. It's like when you look at podcasts, right? Most people quit after recording three.
Gena Gorlin:
Yes. And that's the difference. That's a big lion's share of the difference. I am sure you're familiar with David Senra and his Founders podcast.
Jim O’Shaughnessy:
I know David very, very well.
Gena Gorlin:
No doubt. Yeah. You seem like you'd be friends, seemed like fellow travelers, so just would be simpatico, and I love so much about his podcast, and in this genre of podcasts like yours, like your son’s, and part of what I love in particular about his story is he just kept at it. It's just so clear, in his case, how true. He just outlasted everybody else who didn't love it like he did, and who wasn't just going to keep on recording episodes come hell or high water. And he talks about that in really inspiring ways, it's just like you're going to have to pry the microphone from my cold dead hands to stop recording this podcast.
Jim O’Shaughnessy:
I love David. When David first came to where I am in Connecticut, I have a library over here, and David is so funny because he's oblivious. I love him dearly, but he walks in, what does David do for the first 20 minutes? Just go through all the books. And he's pulling them out and going, "Oh, this one's really good. Oh my God," and then you can see the actual excitement on his face, "I don't have this one. Where did you find this one? Why didn't you tell me about this one?"
Gena Gorlin:
Seriously, what I love, his existence and popularity is one of these beacons of hope in my mind for the civilization that we're trying to build and to rescue and to grow, because I love that so much about him. And what gives me hope is that it's what everybody loves about him. It's what people respond to. It's how he became such a phenomenon within Silicon Valley and just within the tech world, is just precisely by being that guy that you just described, completely, genuinely, unapologetically, unassumingly. That's just who he is, and he's just wearing it on his sleeve all the time, he's not putting on a show, and he's doing a show, but he's not putting on a show, because the show just is him. And people love it. They respond to it.
Gena Gorlin:
And for me, to our earlier point about how do you combat this inner cynicism about other people? It's like, look at the phenomenon of David Senra, the people, the 10x engineers that you want to hire, they're listening to his show, and the fact that they're listening to the show, they're not enamored with his fancy production value. He doesn't interview people. There's no music. It's just him talking about a book for an hour, that's all it's ever been. And all the founders love it, they absolutely love it, and that's why they love it. And you can tell, it's like he ignites that within them and connects to that part of them. And so just hire for that, and know that it's out there. Look how popular he is. All those people are people who love and resonate with excellence and passion. They're the people you want at your company.
Jim O’Shaughnessy:
Totally agree. And he really is, in many ways, a great both example and beacon because one of the things that he really gets, we've talked about it at length, is he is quite distinctive, and David doesn't give a shit if he is not everyone's cup of tea. In fact, David would be horrified if somebody said to him, "Everyone, every single person, loves your podcast."
Gena Gorlin:
No.
Jim O’Shaughnessy:
He'd be like-
Gena Gorlin:
"Done something so wrong."
Jim O’Shaughnessy:
... "What have I done wrong?”
Gena Gorlin:
[inaudible]. That's actually better because it's a good differentiator. It's like, don't hire the people who hate it, because I'm sure people are like, "Oh, it's so good, he just talks for an hour. What's the big deal?" Great. Now you know who to filter out.
Jim O’Shaughnessy:
Exactly.
Gena Gorlin:
Anyway, sorry, go on.
Jim O’Shaughnessy:
Exactly. Well, I teased him in the past. I'm a big fan of Rick and Morty, and when they're trying to get Rick to go to therapy, one of his lines is, "I refuse to submit myself to these agents of averageness."
Gena Gorlin:
Oh, beautiful. I love it. I love it, even despite the fact that it's an argument against going to therapy, which I also can sympathize with because there's a lot of crappy therapy, and a lot of bad reasons to tell someone to go to therapy, so I love it.
Jim O’Shaughnessy:
Yeah.
Gena Gorlin:
Yes.
Jim O’Shaughnessy:
And I think too, that sometimes we get into trouble because many people are label thinkers, and therapy has all sorts of connotations that, maybe reframe and maybe say a coach or whatever, which is smart, which is super smart, I think. Because, well, it's like I really admire people who understand that if some idea or label has either really positively or really negatively colonized our cognitive functions, you would be very wise to avoid the one that has negatively colonized and move over to the one that has positively colonized because it's free real estate.
Jim O’Shaughnessy:
Like my son, Patrick, one of the things that I thought that he did that was brilliant, I have for much of my career been, just I love technology. I started a company called NetFolio in 1999, which was the first online investment advisor, but the tech wasn't quite there, but we kept building towards it, and then I lost thought about the, oh, yeah, the personal portfolio where everything is customized for you is great. And then Patrick walked into my office one day and goes, " Dad, we built the Death Star to kill a mouse here."
Gena Gorlin:
Wow.
Jim O’Shaughnessy:
And he says, "Let's do an AWS and take this incredible tech that we've built for ourselves and give it to our clients and let them use it." But what really impressed me was he understands this concept really well, because everyone was trying to think of a name for it. The ultimate name of it ended up being Canvas, but essentially he called it-
Gena Gorlin:
Wait, like the Canvas? Is this the Canvas?
Jim O’Shaughnessy:
Canvas. Yeah, it's different. Yeah, it's called, it's a portfolio customization software that O'Shaughnessy Asset Management offers to clients, and it's called Canvas. But what I loved, he created a new category that he dubbed custom indexing, and at first when I heard it, I'm like, "Indexing? But we're not necessarily indexing," and he goes, "No, but indexing has such great mind share in investors," because over the last 15 years, it went from being, when Bogle came out with the first index fund, everyone set their hair on fire and was like, "It's unamerican to try to be average," and blah, blah, blah. Then we had a 15-year period where people who simply invested in index funds did really, really well, and so it changed the investors' ideas. But I love the way he hooked custom in front of a very well-known term that, when you put them together, it's like-
Gena Gorlin:
It's like, huh? [inaudible 01:50:47]?
Jim O’Shaughnessy:
Ooh, what's that?
Gena Gorlin:
Interesting.
Jim O’Shaughnessy:
That seems really cool. Well, Gena, I can talk to-
Gena Gorlin:
That's awesome, I think.
Jim O’Shaughnessy:
Thank you. I could talk to you all day. If you've listened to the podcast, you'd know that at the end, one of the things that we ask you is we're going to make you the empress of the world. You can't kill anybody, and you can't put anyone in a reeducation camp, but we're going to hand you a magic microphone and you get to say two things into it, and the two things that you say are going to incept the entire population of the world, and they're all going to wake up, whenever their next morning is, and think to themselves, "You know what? I've just had two of the greatest ideas, and unlike all those other times, I'm going to act on these two ideas right now." What two things are you going to incept into the world's population?
Gena Gorlin:
Oh, man. Oh, man. Oh, man. I get two ideas. It would be, death is the default, and you don't need permission.
Jim O’Shaughnessy:
Oh, I love. Memento mori, and I especially like you don't need permission. That's been one of my things that has done very... It's helped me in my career endlessly. I always ask for forgiveness as opposed to permission.
Gena Gorlin:
Yeah. Truly.
Jim O’Shaughnessy:
Where can our listeners and viewers find all of your stuff?
Gena Gorlin:
Yeah, so main place would be my Substack, builders.genagorlin.com, and then I've done various podcast appearances like this one. If you search for me on YouTube, also the Founders Mindset podcast, which I co-hosted with Alice Bentinck of Entrepreneur First, there are three seasons worth of interviews with inspiring founders from across stages where the focus really is on extracting from them the parts of their story that speak to the mindset, that speak to those nutrients that we talked about at the beginning. How do you build your mind alongside your venture? And what can you learn from the war stories of existing founders?
Gena Gorlin:
And yeah, stay tuned for my book, which working title is The Builder's Mindset: A New Psychology of Ambition in Life and Work. And then anybody who wants to explore, if you're a founder and you want to explore coaching, you can find me at genagorlin.com/coaching.php, or just genagorlin.com would be easy to find from there.
Jim O’Shaughnessy:
Perfect. We will put all of those links in the show notes. O'Shaughnessy Ventures is an investor in Entrepreneur First, so we think very highly of them. Gena, this has been terrific. Thank you so much for giving me so much of your time-
Gena Gorlin:
Such a pleasure.
Jim O’Shaughnessy:
... and really loved chatting with you. All right. Bye.
Gena Gorlin:
It was a joy.