Marx & Nietzsche Are Better Than Any MBA | $16 Billion Guidewire Founder, Marcus Ryu

You said that Marx was one of the most brilliant thinkers I ever read.

>> There is something structural in capitalism that that just drives ever greater alienation. The deepest part of

greater alienation. The deepest part of his critique of alienation was that the capitalist is alienated. The person who owns the means of production is actually the most alienated. And why? Because he

no longer knows how to make anything.

He's useless. He's just an owner. What

does it mean to treat employees as ends and not means?

>> Well, it's to say you are as indispensable as any other one of us.

Right.

>> But they aren't. Right. the people here are bound in a deeper way than the alienated surfs that work for our competitors.

>> Suddenly you made a 180 degree pivot and you ended up building uh a decacorn a $10 billion company. Why do you still self-describe as a capitalist nonetheless? That's fantasy of course

nonetheless? That's fantasy of course and you have to just kind of stop reading at that point. This is not a workers collective. We're trying to

workers collective. We're trying to succeed in a in a capitalist world ultimately.

Marcus Rue was top of his class at Princeton and Oxford before abandoning his philosophical career and founding Guidewire, now worth $15 billion. Marcus

attributes a great deal of his entrepreneurial success with applying a simple philosophical technique to startups. But philosophy also prepared

startups. But philosophy also prepared Marcus in a much deeper and humanistic way. In this interview, you're going to

way. In this interview, you're going to learn how Nichza, Hegel, Marx, and Wickenstein became invaluable resources through the toughest moments of Marcus' journey, and how we may synthesize

action and contemplation in our own lives. My name is Jonathan B. I'm a

lives. My name is Jonathan B. I'm a

founding member of Cosmos. We fund

research, incubate, and invest in AI startups and believe that philosophy is critical to building technology. If you

want to join our ecosystem of philosopher builders, you can find roles we're hiring for, events we're hosting, and other ways to get involved on jonathanb.com/cosmos.

jonathanb.com/cosmos.

Without further ado, Marcus Rue, >> you said that Markx is one of the most brilliant thinkers read.

>> So, what do you think Markx got right and why do you still self-describe as a capitalist nonetheless?

>> Oh, yeah. Well, so so Markx um had an incredibly acute description of what capitalism was. Now, he was writing in

capitalism was. Now, he was writing in the 19th century, but so much of what he said, you know, feels feels salient today. Um, you know, he he characterized

today. Um, you know, he he characterized a tendency to monopoly capitalism and what happens in that. And I think there are clearly parts of our of our world today where we're seeing the the the corrosive effects of monopoly

capitalism. You talked about the way

capitalism. You talked about the way that, you know, that the cultural production is an expression of an underlying, you know, material world and the a relationship between the different factors of who owns the means of

production. And I think the thing that

production. And I think the thing that that Markx talked about that I I really identified at a personal level with was alienation.

>> He talked about alien and he has a very poetic description of alienation. So

what is alienation? Alienation is when you uh are we you are divorced from the produ from the results of your own efforts your own labor right you you

know we're endowed with these faculties to change and move the world and you are exerting yourself but the but the product of what you are creating is uh belongs to someone else right and this

is the characteristic experience of capitalism for the vast majority of people you're a barista you're sitting there like making coffees all day that other people are drinking and that you were completely you were just a you were

you're just a robot. You were in a way unplugging from your human faculties of creativity of expression and so forth in order to be a beast of burden to get something done. Right. And his

something done. Right. And his

description of that alienation was is and of course he was talking about people doing factory work and >> yeah doing the most brutal kinds of agricultural or or or industrial work.

But you know uh poetically I really relate who has not who has not related to that that feeling of alienation and the way that that that alienation kind of is intensified and is it seems to be accelerating.

>> Yeah. With g gig work for example where you even from your workforce >> itself and and the thing is it's not necessary. It's not like well that's

necessary. It's not like well that's just necessary. There's no other way

just necessary. There's no other way that work could get done. That's not

true. That's not true. You like work can be done in an artisal way. People can

have great pride in its creation right.

Um just the fact that the work itself is not glamorous doesn't mean that it has to be alienated. Right? And he says there is something structural in capitalism that that just drives ever greater alienation that turns people

just more and more in treats people more and more like instruments. And there is some truth to this. There is

unmistakably some truth to to this and our current crisis.

>> Did you feel less alienated when you were building your own company? Well,

that's the difference and that's another yet another motivation because when you start a company and I I of course I was poetic about this with people, but I said, "Look, I don't know if we're going to succeed. We're up against much bigger

to succeed. We're up against much bigger competitors and the work we're doing, let's be clear, it's very very difficult and it's very difficult to build our software. It's very difficult to sell

software. It's very difficult to sell it. It's very difficult to implement it.

it. It's very difficult to implement it.

There's lots of reasons that we may fail, right? But we're going to do it as

fail, right? But we're going to do it as a craft. You're going to be treated as

a craft. You're going to be treated as as ends, not means. And we're going to build something great together. or we're

going to fail together within the four walls of our shabby little office here.

The work is not alienated. We are all one and we we may have different roles.

We have different ownership even in this company. We're taking different levels

company. We're taking different levels of risk, but we are part of one larger project of which it treats each of us like a like a like an end.

>> Wow. So, in a strange labor that that is his essay where he mostly outlines the different forms of alienation, right?

Alienation from the end product, alienation from uh your co-workers, for example. Guidewire's sort of values is

example. Guidewire's sort of values is almost an attempt to to respond to marks within capital.

>> Well, I didn't frame it that way. It was

very but a very high-minded in a very high-minded sense. We said the one thing

high-minded sense. We said the one thing that we have under our power is that we get to it's not this is not a workers collective. We're trying to succeed in a

collective. We're trying to succeed in a in a capitalist world ultimately. But

the way that we are going to work here is is not going to be alienated.

>> And um and >> not just for you, but also for employees. No, no, for everyone. For

employees. No, no, for everyone. For

everyone. That's going to be our offer to you. And everything else here is

to you. And everything else here is humble. Like we cannot offer you any of

humble. Like we cannot offer you any of any glamour, any possibility of riches.

We're going to offer you below market wages because that's what we're paying ourselves. But you will at least not be

ourselves. But you will at least not be alienated here. You are going to be

alienated here. You are going to be afforded full transparency with a project. You will know your role within

project. You will know your role within it. And we were going to succeed and and

it. And we were going to succeed and and fail together. And the people who are

fail together. And the people who are calling the shots, the leadership of this company are going to be working harder than you. Okay? And that was incredibly high-minded idea. Um there

was nothing it had nothing to do with our market. The fact we were selling to

our market. The fact we were selling to insurance companies. It doesn't matter.

insurance companies. It doesn't matter.

I think it's but I believe that if I believe there was something magical about that early early stage companies talk about culture all the time, but I think they talk about the wrong aspects like we're going to move fast, you know, we're going to be honest with each

other. It's a lot of like superficial

other. It's a lot of like superficial I mean, not that it doesn't matter. Of course you should be honest

matter. Of course you should be honest with each other. Of course, whatever.

But the kind of deeper sense that this is a collective in which everyone is an end, not a means, is incredibly powerful if you can actually if you can actually instantiate that and live up to it.

>> What does that look like?

>> Well, I mean it's not true of the company today, for example, like things change. Um, and I have regrets about

change. Um, and I have regrets about that because I actually have a theory if I could replay the tape that I could have extended that much much longer.

>> Oh, so now it is alienated again.

>> That's a strong word. I'm saying it's it's lost that kind of crucible like collective sense of feeling that that it had during the really formative years.

>> What does it mean to treat employees as ends and not means?

>> Well, it's to say that you are an indispensable part of a colleable as any other one of us, right?

>> But they aren't, right?

>> Well, I mean, the founders of the company are not indispensable in this in that sense. You're indispensable in that

that sense. You're indispensable in that you are not you're not just you're not just a unit of labor, right? You are you have interests in the success of this collective and your interests will be

folded in and and your your health, your well-being, your sense of professional fulfillment, your advancement. All of

these things are part of the calculus of whether of what we're going to do because we're trying to create a success we're trying to create a successful company, but we're trying to create a successful collective. And those two

successful collective. And those two things are not incidentally related.

they we will be successful as a company precisely because the people here are bound in a deeper way than the alienated surfs that work for our competitors.

Right.

>> Right.

>> That was a very high-minded idea and you could say you could say it was naive. Um

but but the people who were part of those early years were intensely bound by it and came to believe it and and and it made all the difference. Mark's

critique in a strange labor is aimed not as not at specific manifestations of capitalism but as but but aimed at all kinds of capitalistic enterprises.

>> Um so so you would basically push back against that. You say there there is a

against that. You say there there is a way to do un unestanged labor within capitalism. Oh

capitalism. Oh >> well he has this brilliant critique of like of of the way that capitalism is is alienated. And of course the deepest

alienated. And of course the deepest part of his critique of alienation was that the capitalist is alienated.

>> Yeah. Yeah,

>> the person who owns the means of production is actually the most alienated. And why? Because he no longer

alienated. And why? Because he no longer knows how to make anything. He's

useless. He's just an owner. And this is the most beautiful argument. I mean, the guy who has all the power, seems to have all the power has lost his power because he no longer understands how anything is built, right? Or he can no longer do

built, right? Or he can no longer do anything. He's useless. And amazingly,

anything. He's useless. And amazingly,

the oppressed end up finding a new source of power that allows for that inversion. There is a deep psychological

inversion. There is a deep psychological truth, I think, to that estrangement.

And I see it here in the Silicon Valley.

I know not just in Silicon Valley, just in the world. I know some incredibly wealthy people that are deeply estranged and have lost found unhappiness in the

midst of astronomical abundance because >> precisely because of the abundance >> because of the abundance and because they've lost a mastery like their their only mastery is further accumulation.

They've lost a mastery, a creativity, an ability to deal with any to be anything constructive. they've just uh I have I

constructive. they've just uh I have I have witnessed that and there's there's other kinds of emotional and familial dysfunction that can then that can unfold from that. But where does Markx where is he incoherent obviously it's

like well where does this lead well first of all he's part of this kind of as you know he adopted the Hegelian framework which is all of these things have to happen all of these painful stages of feudalism and early brutal

capitalism like that all that has to happen because they all unfolds into something better what's that better thing well you know it's a socialist utopia where the wellspring of abundance just opens and suddenly you know there's

so much surplus that >> we'll go fishing in the morning we'll critique we'll pull a paint in the afternoons and we'll write philosophy in the evening, you know, >> and that's that's fantasy of course and

you have to just kind of stop reading at that point. It's just it's it's just

that point. It's just it's it's just it's wish it's wishful thinking. Um but

I think that diagnosis is or aspects of it are are profoundly relevant. I see.

>> Let me give you another quote from yourself.

>> Severe inequality in income and wealth are not in the long-term interests of any citizens, not even the very wealthy.

This is kind of like what what you're getting at >> with the uh wealthy being alienated through their wealth.

>> Extreme inequality is corroding our civil society, poisoning our politics and undermining our effectiveness as a nation. Is inequality today in America

nation. Is inequality today in America too much?

>> I think so. And I say this as a wealthy person. I mean very wealthy person.

person. I mean very wealthy person.

There's no question that there is that a certain level of inequality is very helpful. It's motivating. It's

helpful. It's motivating. It's

necessary. You can't have you can't have a meritocracy if people don't aren't allowed to, you know, to reap their differential the rewards of their different differentiated effort and

labor and talent. Of course, right? But

there's clearly a level at which it becomes corrosive. There's clearly a

becomes corrosive. There's clearly a level where you end up with political capture, cultural capture, informationational capture, and where you end up with profound estrangement of

of a of a huge number of of of people.

and and that where civil society itself just can't function anymore because it's dominated by just too few individuals whose whims are just carry too much

weight and that's just there's a there's a deep incompatibility with that and a healthy civil society right >> now are we there I don't know I'm not sure but there are things that are

really that are really worrying you know and I um I say that as a very patriotic American a person who's profoundly grateful to this country. You know, my parents came here. They they weren't impoverished, but they were they were

very limited means and I was able to live every aspect of the American dream to the hill. But I've I I I see the enablers of that happen. I see in in

full retreat everywhere. A kind of >> for example, >> the contempt for institutions, you know, I mean, I revered my my parents came here in reverence of those institutions.

You know, that the highest attainment in culture was to perform at Lincoln Center. You know the highest achievement

Center. You know the highest achievement in education was to go to Harvard University. The highest achievement in

University. The highest achievement in journalism was the New York Times. You

know, and that kind of reverence for maybe it was a little bit fetishized, but it was a beautiful thing. They

anchored our understanding of the world.

Now it's everyone's a citizen scientist.

everyone can, you know, you know, maybe injecting horse hormones is a way to, you know, to insulate ourselves against vaccines because there's a global conspiracy that that some kind of crazy

straw reasoning to lead to places of complete incoherence, distrust, and paranoia. This is terrifying, right? And

paranoia. This is terrifying, right? And

and many many people have spoken about this, but the kind of epistemic collapse where we can no longer agree on a shared set of facts is is deeply terrifying, right? And and this is happening. We're

right? And and this is happening. We're

see we're seeing it >> and you attribute the causality the root cause as inequality or or that's another manifestation that's unrelated.

>> Yeah.

>> Well, I think that there's a particularly demonic connection between the kind of the shattering of a of kind of collective epistemically coherent

universe and um and inequality precisely because some of the greatest engines of extreme inequality have been control of the control of information. Right? If I

had to pick a single enemy in all of it, it would be social media. What's

happened with with it? Because it has somehow shattered our understanding of of of a common reality, of a common of a common set of facts. A really tiny

number of individuals have extremely outsized influence on people's basic understanding of the facts, you know, basic basic information. And that is profoundly undemocratic. That's

profoundly undemocratic. That's profoundly dangerous. the natural

profoundly dangerous. the natural monopolies that are in the information ecosystem are are crushingly powerful.

They're more powerful than any monopoly that that existed in the, you know, in the physical world or the extractive industries in the past.

>> You're talking about like Instagram, Facebook X.

>> Indeed. Yeah. I mean, they're they are crushingly dominant and it's because of this completely unappreciated power of the adtech model until it was until it was too late, right? And we're living in

an era of monopoly capitalism now where you know a ludicrous portion of the total enterprise value of um you know even publicly traded companies is

concentrated in you know less than 10 companies right um and so and and that's that that deforms everything it deforms talent it deforms entrepreneurship it deforms innovation and everyone knows

this everyone in Silicon Valley understands this but nothing is changing it in fact it's you're just ending up with more regulatory capture more you know ever greater concentration of power

and it's it's actually um it's distressing when you are part of the Silicon Valley ideology of course is that no matter how mighty the incumbent no matter how powerful the the emperor it's always possible for

>> blow up the deaths are >> it's always possible right the rebels can get there and uh but one has to question one has to wonder now right um and that's that's disturbing to me as a

capitalist as a as a as an entrepreneur one of most obvious and pernicious aspects of monopoly is that the products just stagnate, things get worse. I mean

there was a time in let's say the early 2000s where Google was magical. I mean

and it was a year after year it would release new products that were completely mind-blowingly magical, right? Like you have geoloccation of

right? Like you have geoloccation of every single useful destination that you may that you may want to go to and it's free. you know, you have all the movie

free. you know, you have all the movie times that you may want. You oh, you have Google Docs. You can now collaborate in real time on on documents for free and just incredible sequence of

of innovations. It's been complete

of innovations. It's been complete stagnation. 20 years of a company that's

stagnation. 20 years of a company that's now just been in extractive mode.

Everything has gotten worse. Search has

gotten worse. Google Google Docs has gotten worse. The geoloccation has

gotten worse. The geoloccation has gotten worse. Everything has gotten

gotten worse. Everything has gotten worse. Right. Right. Um and argue the

worse. Right. Right. Um and argue the same for Microsoft. You could say the same for many other tech products. to

see and so that's the that's the clearest indicator >> right so for the first two and a half decades of your life you were on track to be a superstar uh philosophy academic

and then suddenly you made a 180 degree pivot and you ended up building uh a decacorn a $10 billion company what are the most important ways you think your training in philosophy if however subtly

>> um prepared you to build this decadillion dollar company >> well we had the strategy right and then we executed on that right sounds so straightforward Um well a philosophical training is very

helpful for defining what a strategy is.

For example, you know, one one of the things you that professional philosophers do at least in the analytic tradition is that they they they value simplicity and clarity in their communication and they tend to write things as propositions when when they

get to the real heart of their argument.

They will often like number their points and one one a >> and propositions and they say well you know 3 follows from point two you know intrinsically.5

intrinsically.5 is only true if either one or two must be correct and it's a kind of basic propositional logic that that you that

you learn as a basic language in in philosophical training and this is immensely helpful because and it's what I urge entrepreneurs to do a lot is to take your own beliefs about the market your own diagnosis of the market and

your own intentions and to write them as propositions in the simplest form unadorned with marketing or self-promotion and then you can interrogate cause out the actual logical

relationships between them and um I think a lot of businesses a lot of startups would enhance their chances of success if they do if they were to do that. I deeply relate to this because um

that. I deeply relate to this because um when I was on the founding team of a company with with Lndale it was also a very big founding team like you guys. I

was 21. I was a senior in college. The

average age was like 40.

>> And the biggest value ad I think I had during my, you know, three, four year tenure >> was simply during leadership meetings.

>> Mhm.

>> Doing the exact exercise, >> which is you say A. Yeah.

>> Which implies B.

>> Yeah.

>> You say C, which implies not B.

>> Yes.

>> And me as a as a again a 21-year-old, I have no idea whether A, B, or C about the market are true or false.

>> Yes. But I know that A and C like if we have both A and C in the company strategy, this thing's not going to work. And it's simply just this internal

work. And it's simply just this internal like coherency was enough to to actually help the teams kind of straighten out our our thinking.

>> That's exactly what I'm talking about.

It's exactly it. It's a kind of basic propositional logic and and and inferential coherence that that you learn in philosophy and even I I I've

been witness to it many times even very successful like multi-billion dollar companies that are incoherent at at this level that they are they're that if you were to yeah if you were to lay it out you would say this this argument is

invalid I don't even know that the market in question I just know that this the sequence of reasoning is invalid >> right and this is a superpower in some sense because you can add value as an

investor or as a team member without market knowledge, right? Because it's

completely in internal to the argument itself right?

>> That's it's the part of investing I like the most by far. Well, actually that's I like second most. The thing I like most is just the interaction at an emotional level with founders because there's a kind of deep universality to that

experience. The second thing I like

experience. The second thing I like though is this kind of very collaborative cross-examination. You

collaborative cross-examination. You could call it Socratic, you could call it um cross-examination where you're just asking. So if I've heard you

just asking. So if I've heard you correctly, you know, you've said proposition one. Is that did I get that

proposition one. Is that did I get that right? And then two and you're saying

right? And then two and you're saying that that we're we one is axiomatic, two is contingent, but you think you have good evidence for it. And if both of these are true, that's why you're hence this. What would be contrary evidence to

this. What would be contrary evidence to that? And you know, and this kind of

that? And you know, and this kind of questioning in done not so pat not patronizing, not like a professor, >> but just as as an investor trying to understand what they're doing, I find is deeply appreciated. It's done

deeply appreciated. It's done respectfully and often yields even in a first conversation even in that first half hour >> introduction insights for them. Right.

>> It did. And I for me it's a profound reward when at the end of that first meeting they say this conversation is different from the kinds I've had with other investors.

>> Right. Uh I'm glad you like cross-examination because I'll be cross-examining the things you've said over the past 10 years to see whether Marcus is coherent. Yeah,

>> I welcome it.

>> Let me give you a quote um to to highlight another aspect of of a strategy. Not just the internal logical

strategy. Not just the internal logical coherence but but something else that's quite incredible. Okay, this is this is

quite incredible. Okay, this is this is you speaking.

>> Before we built anything, we had already conceived a product. We called it the binder and it basically defined the company's product strategy for the next decade. It was a theory a theory of what

decade. It was a theory a theory of what needs to be built and the sequence thereof. What was the MVP? What were the

thereof. What was the MVP? What were the nice to haves? Where we would have to satisfy existing requirements where we could build something 10x better. And it

was extremely precisely and lucidly captured in a document that we then built and defined the company strategy for a long time.

>> There here right is another dimension of the strategic thinking >> in addition to the logic >> which is to almost have like a conception of the world or conception of

the thing the form the platonic form >> that you then actualize in the world which is also quite very unique in company building. Yeah, it's not quite

company building. Yeah, it's not quite that grand, but yes. So, that binder was it was written by my co-founder with the benefit of no knowledge whatsoever of the market that we were serving. Just

through patient cross-examination, very respectful from the people that would talk to us, he composed a theory of what would be the right product. And it was like any good theory. It was rigorously

tested. It was iterated many times and

tested. It was iterated many times and it was adapted and so forth in the realm of thought.

>> In the realm of thought, but also just kind of counterfactual reasoning. It

would say, well, should it be this? And

then they said why wouldn't that work and what would be deficient about this and like let me show you what that could look like you know this kind of iteration with people who were actual practitioners and these were all people by the way who as you know they were all

capable great professionals whatever but they would have been incapable of describing this product themselves. They

could not have it was his genius to extract from them their domain understanding to actually build and iterate that product >> and then to put it in a document and a document that was actually other

engineers who were also innocent of the domain could build the right product and to then come up with a concept of a product that was ended up being so resilient that it sustained a company to

market leadership over dozens of competitors over two decades is I think um a rarer achievement than um you know

than it should be. Um that design work that happened in the earliest days. We

were penniless. We had no funding. Um

and was done just through kind of humble respectful interviews with people in their domain who were doing it just out of joy of telling us of someone being interested in their opinion.

Incidentally, um we uh we gave some of them stock and they had no expectation of it being worth anything. And then

when they they found oh a4 million dollars that they hadn't didn't expect, it was such a joyful moment for me. I I

I I I I take such delight in the fact that there were people who gave their time not with nothing no expectation of return and then a decade later, you know, or more than a decade later, you

know, found a really a meaningful outcome for themselves. So, I I really enjoyed um reading and listening to all of your talks when you described this theory, this binder, uh because it

showed me that I'm not crazy >> because I at least on the founding team was that person who was like, >> "Okay, let let's try to progress in thought >> as much as we can."

>> Yes.

>> While recognizing the limitations of thought before we actually do things.

>> Yes. Because the speed, the velocity of of thinking and testing counterfactual and doing interviews is a lot greater than building a product and testing and finding out it doesn't work.

>> That's right.

>> Again, this is not the prevailing intuition I think today of building companies.

>> In fact, a kind of hyperactivity >> is kind of almost woripped if not deemed necessary. Yeah. Right. So tell us about

necessary. Yeah. Right. So tell us about that.

>> Well, the extremes are are disastrous.

Uh you cannot build a product you cannot build anything in in pure isolation in thought. Right? I mean, unless you're

thought. Right? I mean, unless you're writing a work of philosophy, you you need to engage the world. Um, but just frenzied activity, you know, um, that's that's not well-directed is al there's

the surface area is too large. The the

the set of possible products is too vast. There's too many parameters. So,

vast. There's too many parameters. So,

you have to you have to condition the search. You have to shape it in some

search. You have to shape it in some way.

>> So, the there there are the two potential answers one can give to the question I just asked.

>> The one you just gave seems to be there's a golden mean. Yes. There's a

golden mean between thinking and activity. And your point is most people

activity. And your point is most people think that the diminishing returns >> come a lot earlier than they actually do of thinking. There's a lot more to be

of thinking. There's a lot more to be done in thinking.

>> Well put. Yeah.

>> There's another way to answer my question that which is what the one I thought you were going to say, >> which is that for nerds like you and me, this is the right path, but for some

kind of hustler guy, you just, you know, and and there it's more about what approach suits you.

>> Yeah.

Well, one of the humbling things about about the journey for me is realizing there are different models of success.

There are different ways. Um, for

example, there are companies that are led by one charismatic messianic figure who takes the team to the promised land and uh and who just

who just knows the way and who makes all the decisions, has a concept of the product and through sheer force of will wins the early customers and and and and so it unfolds. That is a model of success. That was not our our model of

success. That was not our our model of success. Our model of success was

success. Our model of success was radically collegial, very rationalist and and a person who came from that former model who tried to come into the company would have been a disaster. It

would be like who is this clown?

>> And vice versa.

>> And vice versa. Because to be a a rationalist while, you know, while the Messiah was preaching would be like >> a heretic. Yeah.

>> Now you're a heretic. Exactly. Or like

you should be getting in line. What's

what's this what's this alternate exercise? Right. So there are different

exercise? Right. So there are different forms of organization, different different paradigms of and I I acknowledge that. Um but for us uh and I

acknowledge that. Um but for us uh and I believe and I believe many of the most the companies that I admire most and that I think have been the most durable, they had this kind of quality um this

kind of hyperrational extremely customer oriented but also deeply opinionated theory about like what the best product ought to be. You could pick HP, you could pick IBM or you know companies

that were so visionary and and compounded such value over such a long period of time in such a consistent and characteristic way, right? And then lost their way, right? And but during those

periods where they they they were that successful, they were animated by this kind of in my opinion this kind of product theory, this kind of this kind of care about the right the right the

right what what a product should be and then iterating on it with rigor so that it's the last decimal point it actually worked.

>> So your first response is to retreat a bit and to say that it is a personality dependent kind of thing.

>> Yes. But then you also want to gain back some ground by saying but >> even though you can build good companies in this messianic way this rational way is more sustainable more longlasting or

is perhaps the best thing to say is it's the only way that I understand and I mean I'm I'm personally mystified. So

let's let's say any company associated with Elon Musk is >> uh messianic >> is messianic by definition. He is it, you know, he embodies 95% of the enterprise value in his opinion and

that's I I don't and I don't understand it. So I rather than criticize it, I can

it. So I rather than criticize it, I can just say I can just report incomprehension. This is the

incomprehension. This is the Wicksteinian silence just >> right.

>> Uh it works in a fashion that I do not understand.

>> So I was going to cross-examine >> your desire to cross-examine.

>> Okay. Sure. But by pointing out the very thing you said which is there are multi-billion dollar companies that are not coherent at all.

>> That's right.

>> Right. And so so but this is just another uh u way to point out that there is another mode of success that is almost like indecipherable to you.

>> Yes.

>> It's right.

>> Let me give you another quote for you.

>> One of the many illusions that my entrepreneurial journey cured me of was thinking that I was such a great judge of character. We all think we're such

of character. We all think we're such good judges of character and then we find that we actually make terrible mistakes all the time.

>> I was surprised that this wasn't one of your strengths because when I talk to people like us who philosophy then it went into industry the most consistent

answer isn't this kind of logical analysis that we've been describing.

It's the ability to see in people's souls like to make really quick and and like very strong opinionated judgments on people. But you didn't get that from

on people. But you didn't get that from philosophy.

>> No, no, no. I Well, I've certainly made too many mistakes uh to possibly ascribe that kind of power to myself. Um but I don't ascribe it to almost anyone anyone else either, right?

>> Um because we are deception machines. I

mean, we are that's we're evolved to be very persuasive to each other about and very good at obscuring our actual motivations. And that's this enormously

motivations. And that's this enormously strong evolutionary pressures to be good at that. And um and I think it's it's

at that. And um and I think it's it's sheer hubris to think that one bit of evidence to my point of view here is if you ask you know you know serious entrepreneurs people serious executives

who've gone you've managed a lot of people have hired a lot of people gone through many years and said what's your actual success rate if we were actually to count the people that you hired to report to you how many fulfilled or

exceeded your expectations and a year later you were you were thrilled with them what what percentage you will very rarely hear something higher than 50%.

Half the time they hired people who tried that and that's my track record was probably I don't know 40 to 50%.

Something like that, >> right?

>> Um and that's it's just kind of anyone who says higher. I've been in groups where exact you know founders have talked about this and someone said I don't know about 70 or 80% and everyone said yeah right really and when they

actually thought about it no you're right it's more like more like 50%. So

your defense or excuse is something like >> I'm bad at it. So so is everyone else?

>> So is everyone else but did philosophy make you better at it? Actually it made me worse. And the reason and I and I'll

me worse. And the reason and I and I'll say it made me worse in this specific way because I it it preconditioned me to like a certain kind of persona, a certain kind of person. It exposed me to

being deceived, let's say, by people who were charming interlocutors, you know, for people who had, you know, scintillating intellects, people who had diverse interests and I, you know, I

would overindex on those kinds of people. I would say, "This guy's great.

people. I would say, "This guy's great.

He's he's an intellectual peer. He's

going to be he's going to be a thought partner. It's going to be great."

partner. It's going to be great."

>> And it turns out that that's a very small part. It may even be an antiattern

small part. It may even be an antiattern for being a good person, >> a good operator, >> a good operator, especially in an early

stage in a company. Um, and uh, I I I after making several serious mistakes on that count, I came to recognize there's a whole other set of traits that have that have mattered most. Look at the people. Now, let's look objectively,

people. Now, let's look objectively, empirically. Who has made the biggest

empirically. Who has made the biggest difference in my company in this company together? You know, there's my

together? You know, there's my co-founders of course, but who's made the biggest difference? And they were not the ones that had went to the best schools. They were not the ones that

schools. They were not the ones that were intellectual in the way that I would have defined it. They were the people who were the most loyal. They

were the people had the right strongest work ethic. They were the people who are

work ethic. They were the people who are most reliable and highest integrity and the ones that um had the deepest sense of personal accountability to to fulfilling their you know their role.

>> Well, those traits aren't in tension with intellectual intellectual >> it's orthogonal to right. So, so it's is it better to have the intellectual plus that

>> that's that's glorious if you but it's like it's like you're fishing for the wrong thing if right then your priorities wrong you got you got the ordering wrong >> right and then you're just lucky maybe you'll get lucky as indeed we did there

were people who had it all um but >> uh but it was we were searching for the wrong criteria or I was >> what were the other ways that your training in philosophy actively disadvantaged you that you had to unlearn when building the company

>> one of those was the communication of applying a contian principle of reciprocity let me let me treat others exactly as I would like to be treated. So let me communicate to people the way that I would like to be communicated to and

that would you know so I want to understand I want to understand the whole logic I want it inductively explain to me what are the premises and how how do the conclusions therefore follow and that's how I shall

communicate to people and but that it takes time though it takes a lot of words it takes you know diagrams a lot of slides a lot of connective logic in

order to explain things in this way and I was um fairly deep into my tenure you know during my time as CEO where I would give you know I would I would talk to

the company in meetings and you know I would have a kind of almost long like thesis statement about where we were and why we were deciding the things we were and I thought this is what people wanted to hear and it turned out not to be at

all there was a point kind of late in my tenure when I realized that people didn't want the long uh like like deeply inductive and explained elaborated explanation of what we were doing that I

was completely missing the mark on on what team wanted to hear. What they

wanted was the following. They wanted

clarity. They wanted concision. And they

wanted repetition. They wanted to know there's Marcus. He is saying the same

there's Marcus. He is saying the same thing he said last quarter and uh and the quarter before that and the quarter before that. And we he said we're going

before that. And we he said we're going to have these ambitions and we've met those ambitions and we're now have bigger ambitions. But it's in the same

bigger ambitions. But it's in the same framework and he is reiterating the same comforting truths that that define this company and our strategy. that's what

they wanted to hear. Um they didn't need they didn't need all the early elabor initial first principles elaboration of that. They already bought that. That's

that. They already bought that. That's

why they were there. They already

believed it. Still in that same vein, you know, I used to communicate in like far too cerebral a fashion. I had I had a weird tick which was kind of the more nervous I would get, the most the more socially awkward I would get sort of the

more uh the more elevated my addiction would get. And you know I was talking

would get. And you know I was talking like an Oxford dawn sometimes by the time in a sales meeting you know because I was so uncomfortable in the situation to to a degree that I I was conscious

was preposterous you know and I was using more I just couldn't stop I mean I did correct that habit later but um and it was yeah it was a kind of a character trait that you can learn in the academic

world sometimes that when you're insecure then you kind of retreat to you know >> start developing a posh British accent.

>> Yes. you or you retreat to obfiscation or something and that's that's not a good trait even in the academic world of course.

>> So tell us about that transition >> until my mid20ies I was absolutely certain that my destiny was in the academy that I would be a professional philosopher or maybe a literary critic.

I was a very serious student my entire life. I was better at school than I was

life. I was better at school than I was at anything else. That may still be true. Um but I uh I suffered a crisis of

true. Um but I uh I suffered a crisis of anxiety that um the academy might not have a home for me and >> because you weren't good enough or >> perhaps or perhaps the world would be

unfair. I don't know. I didn't know. But

unfair. I don't know. I didn't know. But

I I felt I was getting a very adverse signal from all these other young um young academics early in their career who uh who were racked with anxiety that

they wouldn't have a home themselves.

And I didn't have the hubris to say, "But I'm different than they." You know, I'm so much I'm vastly superior. And uh

actually the sentiment I had was I've been running the wrong race my whole life and the world operates according to a completely different schema than I had I had understood before and I have to

now change course very painfully. Uh but

time is short and I've got to get on to it. and uh was recruited by McKenzie at

it. and uh was recruited by McKenzie at a very vulnerable moment and uh before I knew it within a few years I decided I was put on this earth to be a software

entrepreneur. I started a company and

entrepreneur. I started a company and somehow 25 years passed. Many of the many of the people that were in my BIL program that were in the BIL at Oxford ended up now have distinguished philosophy careers. And so they would

philosophy careers. And so they would always say to me, you know, how did you go astray? Like you were you were more

go astray? Like you were you were more of this than we were at the time. And um

>> I I don't have a good answer, but I have no regrets about the way it unfolded.

It's a tragedy of our existence. We only

get to run the tape once. Um but I I was motivated by anxiety and by by fear.

That's that's that's truthful. And in

fact even on the entrepreneurial journey sometimes I'm asked you know what drove you you know to spend decades uh trying to do something difficult and improbable and against the odds you know was it uh

was it a quest for glory and I I I always say it was not a quest for glory there was no expectation of great success but there was a terror of failure and that was a very profound

motivator throughout um throughout and you know there were many joyful experiences there were many was it was filled with meaning and purpose But uh at the end of the day, the most

intense motivator, the kind of the sort of the life force, the will to power was much more one of uh of anxiety about not about not succeeding.

>> Interesting. But you picked a notoriously difficult industry to build in. So if you're that afraid of failure,

in. So if you're that afraid of failure, why why did you pick also choose the sort of an extremely difficult industry to build in?

>> In a word, ignorance. We were saved by ignorance. Had we had any sense of the

ignorance. Had we had any sense of the difficulty of the market that we had chosen or just the entrepreneurial journey itself especially at that time uh we would not have embarked on the journey. And so it was um you know it's

journey. And so it was um you know it's good sometimes that you have to lash yourself to the mast and and uh not be not allow yourself to give to temptations of ending things prematurely

that you have to just you have to commit and go. And that's the character of the

and go. And that's the character of the entrepreneurial journey and and perhaps of a of a well-lived life that you make these kinds of commitments far before you have all of the all of the criteria, you know, to make to make a wise judgment.

>> A leap of faith.

>> A leap of faith indeed. Yeah. And that's

that's the character of life. And it's

of of a well-lived one, but one that's not lived in terror and and in um you know, in in retreat. You have to you have to take those risks. Well, hold on there because you said that on one hand

a life lived in this way is one that is free from terror and yet the previous statement you made was one that is fear driven. Like how do you reconcile these?

driven. Like how do you reconcile these?

>> Yeah, I think both are true. Uh I

describe it as the subjective habitus of the entrepreneur. It's a kind of

the entrepreneur. It's a kind of combination of exhilaration, exaltation on the one hand and uh and terror and despondency on the other. uh and that is why is one of the reasons why it's such

a difficult place to inhabit for a sustained period of time. It's part of the loneliness of that journey because you have moments of very very high highs, very you know exhilarating senses

of something improbable that we are making happen and then also you know this crushing disappointment when you say even the next step even to take one

more one more step on this journey is is too much to ask is is too improbable and um to to be able to retain both of those at the same time is very taxing you know in the same vein I used to have there

were there were long stretches is where I had two thoughts simultaneously. One

was we must succeed. We must I've I've I've poured my my life, my career, my life force, my potential into the success of this company.

>> Sorry. Sorry. Is that a descriptive or normative statement that we are going to succeed or or we have to >> somewhere in between somewhere in between that we must we must because what else could happen and we must because there is no how terrible the

alternative would be and I would have that on the one hand and on the other hand I would say but we're not going to like the rational part of me would say if I underwrite the situation here it's very negative that as a dispassionate

one if I could exit this first person perspective I would say we are likely to fail in fact we're almost certainly going to fail and then I would flip to the other side the first person perspective ive to say but no but we must succeed there's no other

alternative and this kind of oscillation between we must succeed but we're going to fail but we must succeed but we're going to fail at the same time it's it it's enormously fatiguing it's very very difficult that's so interesting because

the way you described >> this fundamental tension between the third person objective and the first person subjective >> is almost like religious experience >> right because from religious experience

um I mean even the believers they themselves admit like if you r like like You can't rationally get to God at least and not not the Abrahamic God.

>> But from the first person perspective, something that might seem so mundane and innocuous can can just pull you in a way that you can't possibly describe. And so

so it's almost a religious tension you're wrestling with. I mean so the the the difference between the first and the third person perspective is kind of it's kind of the the tap routt at a whole host of philosophical questions

including most I think in my opinion the deepest the most unfathomable question of all which is how does our mind how does a mind and subjectivity exist in a material world it's it's the deepest of

all mysteries right but that is also a switch between the first and third person perspectives all the time I inhabit the world in a particular place I am situated at a particular locus and I have a set of experiences that are

distinctly and and maybe even privately mine but at the same time I am an observable embodied creature at the same time and in a way and I see much of the the kind of entrepreneur entrepreneurial

journey through this philosophical lens and that's the theme of our conversation um I you have that as well as an entrepreneur you have this first person drive which is I can but I can only

succeed and you have this third person reality which is that the world is indifferent and we could fail and we and we probably will. So here you were making an even more interesting claim that your condition is generalizable.

>> I think so >> because I was going to say you thought your disposition towards the terror and the fear was quite unusual.

>> Is is that right? As I've gotten to meet more entrepreneurs over the years um I recognize a kind of deep universality to it. Now there's a some there's a subset

it. Now there's a some there's a subset of entrepreneurs I don't know if they're sociopaths that sounds too judgmental but who somehow are kind of inoculated.

They're inured against this kind of >> they only have >> the first person. Yeah.

>> They they only have the first person.

They they're just not >> they don't suffer from self-doubt. We

all know these people, right?

>> And I don't know if it's a blessing or curse to be that way, but that's something fundamental in a person's character.

>> Well, empirically, do they work out or do they not work out?

>> I think we know some spectacular successes and for whom that was a critical ingredient. Just a complete

critical ingredient. Just a complete absence of self-doubt no matter how outrageous their claim >> and you believe them. And you believe them. You don't think they're kind of

them. You don't think they're kind of like putting on a show to others or >> I don't think so. I I know a few of these people and I think it becomes so maybe they get a powerful feedback signal that they're that people are just

swayed by their conviction and you know and we lionize some of these people this reality distortion field you know that that some of the most charismatic founders or leaders have. Um but there's it's a fine line between that and a kind

of sociopathy right like where you're just >> you're just kind of indifferent to the world. You're indifferent to the

world. You're indifferent to the presence of other minds and their needs.

And um and I don't want to be that kind of person. I will I am not that kind of

of person. I will I am not that kind of person and most people are not like that. Um and we have to be careful not

that. Um and we have to be careful not to be dazzled by some by people that way because it's very dangerous and they can lead to very bad places. Historians have

very ambivalent attitude towards these great great people. I mean like a Pericles or you know or a Napoleon or you know who just you know kind of they are the agents of history. They move

things forward. Um but at the same time they can be the agents of just tremendous suffering and and disaster.

One of the one of the beautiful comforts of of reading Hegel and or thinking about him and his his worldview was that you know that sometimes that you would have these agents of history that might

do terrible things but they were always in the service of a larger unfolding of something eventually becoming better a trajectory towards something that was more enlightened however dark the path might have been to get there and that's

a that's a very helpful comfort in in the darkest moments. I used to I used to philosophize aspects of the entrepreneurial journey a lot and um I would I thought back to those days of

reading Hegel and and our own journey and I would I would think about the moments of of devastating failure and but then also say well this is going to be metabolized it's going to be

reinvented into something that will be a source of strength in our in our future and uh that was a great comfort to me and where our product didn't work at first and we had to disappoint customers or we had uh a rupture with our

investors and they imposed a new CEO on us that was a disaster, you know, or we were sued by our primary competitor um and who nearly put us that nearly put us out of business. Um, so each of these

were devastating events that that really were they put the company on the knife edge of just being game over and each of them because we survived we survive

stronger and you know and I'm it's it's a truism you know the things that things that don't kill you you know um fortify you but they >> uh but I got to live that and you in a particularly intense form.

>> Well what's quite different between um Hegelian philosophy and what you just described is that there's a necessity in Hegel. That's right.

Hegel. That's right.

>> Which doesn't exist in these examples.

Like you could very easily see how like your competitor Accenture in this case could have just sued you out of business and there was no >> there was no sublation to >> but a key part of Hegel is that you

don't know it's like the participants in history first of all they're expendable but secondly they're not they're not aware of of what happens the most famous line of all is the owl of Manurva only

takes flight at at dusk. It's only at the end that you get to you get to piece together the narrative that you've been part of. But while you're in the middle,

part of. But while you're in the middle, you have no idea and maybe you'll you'll disappear without a trace.

>> It's like Dung was asked um what he thought of the French Revolution and he's like too early to tell.

>> Too early to tell. Still unfolding,

>> right? So tell us about what you most cherish about the entrepreneurial path that you wouldn't have gotten in the academic path. Um and vice versa. What

academic path. Um and vice versa. What

do you regret most or what do you miss most about the academic path that you didn't get on entrepreneurial path?

>> It tested me. It tested me in in an extreme way, a way that um you know to to really I realized I had taken a much greater risk than I realized not with my life but with my career with my

aspirations with my my sense my self-conception as a successful person or you know a person of >> leaving the academy you mean the academy and I hadn't I had put that all on the

table and was now gambling with it in a way that was was very frightening at at times and you know different people are not encumbered with that same sense of of needing to succeed. But you know,

when you're a first generation immigrant kid and you are the hope of your generation and your parents have labored and sacrificed to send you to give you the best education and you now realize

that you may come to nothing, it it weighs very very painfully, right? And

so to be tested in that state and and to not have just done the cautious thing that I could have done along the way and to have come out the other side of it is was you know let's let's call it the

defining experience of my my life. Um

the other great thing it gave me was um it compelled me to interact with people who are not like me. So, if you encountered me at 25 and you had read some of the same books and had the same

kind of intellectual disposition and the same kind of cerebral self-s seriousness that I did, well, I would talk with you all night, >> right? I'm sure we would have gotten

>> right? I'm sure we would have gotten along. We would have been fast friends

along. We would have been fast friends and we would have had we would have talked infinitely. But if you came from

talked infinitely. But if you came from a different part of the country, if you um had a different relationship to religion, if you enjoyed different activities, um then I would be out of I

would be at a loss, you know, in the first 30 seconds. I wouldn't know what to say because I would say we've exhausted our common ground. And um you don't you you can't afford that, you know, when you are an entrepreneur. You

must find a way to meet your you have to meet your market first of all on its own terms. You have to speak to it in ways that are not condescending. You have to be you have to bring a humility and you

have to you have to be prepared fundamentally to learn from the people that you're speaking to even if they look completely different than you. And

um compelling me to adapt to that over and over again in ways that were intensely uncomfortable and unnatural to me over a sustained time. No question

made me a better person. No question.

>> Better better in what dimension? more

empathetic, more self-aware, more compassionate of people who had different life experiences or and um and just more capable uh you know as opposed

to being paralyzed in situations where that were not perfectly crafted to my form of communication now to be fine in any setting. Um and you know especially

any setting. Um and you know especially growing up as a minority extremely cerebral and introverted that was a that was a profound gift um to be able to to do that.

>> Hegel's philosophy of right >> um he gives a defense of the market economy that >> it has an educational role and it has a formative role because precisely as he

says the market forces you >> to interface with the wider world. Yes.

>> Um and in your case this was a global world. Guidewire, your company

world. Guidewire, your company eventually became not not just with global uh uh customers but also global employees. Yeah,

employees. Yeah, >> that's right. With employees but but just different parts of the world and people in who had completely different life experiences. And it's one of the

life experiences. And it's one of the tragedies of our or one of the the great risks of our modern era right now that it's impossible to sequester yourself with only people who already agree with

you. And that's that's a profound that's

you. And that's that's a profound that's an this is a experiment that we don't know how it's it's we're unarted.

>> It's it's the reverse of the effect of the market that Hegel wanted, right? the

market forces you to interact with all kinds of different people. That's right.

Because you know they're paying money, they're customers.

>> That's right.

>> Now we're living in a for example social media environments where you're kind of in it. Exactly. And that's um it's

in it. Exactly. And that's um it's >> it's uncharted waters exactly where that leads. But so far the indications are

leads. But so far the indications are not good.

>> Right. So what about the reverse? What

do you perhaps regret or what would you have liked to experience in the academic path?

>> The thing I miss most was is a certain kind of depth of contemplation, right?

you know, you're always on the clock. Uh

when you are in the in the world of commerce, there's an understanding that that in in the academic world that serious thinking takes serious time and it takes and it's incremental that you

are a participant in a vast river of human thought and achievement and contemplation and your goal is maybe to add the tiniest bit of sediment, one pebble onto this vast edifice of human

understanding. And even that will take

understanding. And even that will take time. And that basic understanding

time. And that basic understanding you're not afforded in the in the entrepreneurial world. But I I miss I

entrepreneurial world. But I I miss I miss being able to read for very long stretches and the kind of deep immersive reading or deep immersive conversation and so forth. And actually I discovered

at during the COVID years that I had really lost the faculty. I just couldn't I I'd always thought of myself as a you know very as as a great reader. I love

to read and I realized I've read very little in this last 15 years. and let me let me rectify that now that I have time. And I found it uh disturbingly

time. And I found it uh disturbingly difficult. I found it very hard to read

difficult. I found it very hard to read serious works. And um fortunately it

serious works. And um fortunately it came back but not after I mean not before a good 3 or 4 months of like kind of struggle. It was like being very out

of struggle. It was like being very out of shape >> uh to learn just to read again properly.

>> So that was also kind of my big issue with the startup uh life which is why you know much earlier than you I decided to go back to contemplation. The way I describe it is that if you were to rank the the difficulty or profoundity of

decisions, right? Let's say, you know,

decisions, right? Let's say, you know, math is 99, philosophy is 97, physics is 98, >> and then uh I don't know, our history is like a 60.

>> For me, a lot of entrepreneurship is just like >> solving a lot of like level 40 questions like to a reasonable enough accuracy over and over and over and over again.

>> And that was just a kind of a mental tedium that I could not stand.

>> Well, a lot of life is tedious that way.

A lot of most most ordinary jobs have that quality. I mean the the the

that quality. I mean the the the redeeming aspect and the the exhilarating aspect of entrepreneurship is that you get to do it on your own terms as the owner, you know, on the vector of your own decision. Um but yes,

that's it's very that that's fundamentally different. On the other

fundamentally different. On the other hand, there's a kind of academic or an intellectual despair as well, which is how can I possibly contribute to this vast edifice? You know, I don't even I

vast edifice? You know, I don't even I can't even find a grain of sand to add to this this huge pyramid. And uh that and that's a different kind of you know kind of despair.

>> I see. Did you continue to engage with philosophy at all during after you left the academy?

>> Very little professional philosophy sort of like like serious academic journals.

I did not read um so much but I would read philosophical works and I still do.

Um they tend to be a little bit more written for the amateur than the kind of hardcore professional philosopher. But

even then I read some I've read some pretty heavyweight philosophical texts especially in the last few years where the the the workload has not been as demanding. I don't know if I would have

demanding. I don't know if I would have ever made it as a great professional philosopher. Um, I liked that tribe of

philosopher. Um, I liked that tribe of people. I liked I like people who were

people. I liked I like people who were capable who whose minds had that kind of facility that we could talk with great precision over long extended periods of time. And I've not had that since then

time. And I've not had that since then and I I I miss that. But it's very hard to replicate that now once you're outside of the academic world. And

there's a kind of there's a kind of loneliness to reading those texts because um a lot of the joy of it would be to engage with another person either the person who wrote it or the people who were talking about it and I don't

really have that today.

>> I see. What is the fact that you stopped engaging with uh philosophy after you left?

>> Tell us about your original motivation engaging with it. The difference between you and I was the reason I left the entrepreneurial world in in four years instead of 20 25 >> was because I couldn't stop reading

philosophy.

>> I I would find myself like you know 11:00 p.m. after after work when I was

11:00 p.m. after after work when I was done the day like just grabbing up Augustine or something like that. Mhm.

>> And I suspect the answer is because I came into philosophy as a practical thing. Like I wanted to figure out like

thing. Like I wanted to figure out like my my most like urgent questions are all around ethics and how I should live >> where perhaps and I'm speculating >> you treated philosophy as like a

competition as a glory as a and and there right you simply just turned your gladatorial ring into another arena.

>> I think that's very insightful. I think

that's actually largely true. Um, I was better at school than I was at anything else. And you know, especially when

else. And you know, especially when you're you're a minor minority kid, uh, you're socially awkward, you're introverted, you know, just like anyone,

you say, what can I attach to? What can

be my source of of confidence? What is

what is my source of power in this world? And for me, it was um a kind of

world? And for me, it was um a kind of intellectual facility that I had, ability to read far beyond my age level when I was a kid. just ability to get to be showered by praise you know by

teachers you know along the way uh to get into have a very prestigious education and these things were you know these things were a comfort that that showed in this difficult sometimes

unfriendly world there is a meritocratic path where I am excelling and it happened to be you know it happened to be humanities it happened to be including philosophy um so you're right

it was a kind of professional domain and I was able to then change with difficulty and with a lot stress was able to change that redirect

>> uh recct you might say uh that kind of life force ambition and energy towards something else. Um but it came at a

something else. Um but it came at a price and that attachment in the in the beginning was not totally arbitrary.

It's not like my father right >> you know cracked a whip and said I'm going to play the violin. Uh I I was naturally cerebral in that way. I liked

I like to read to inquire and I like to press points, you know, far beyond the kind of comfortable level that, you know, where kids eventually encounter so much resistance that they just, you

know, that they stop and um and and I I retain that today and I'm and I'm grateful for it.

>> In my own case at least, I found my journey a lot more brief into into into the active life so to speak >> quite help helpful for my philosophical

interests and endeavors. Now it it adds a sort of weight. I think Plato recommended um young men and women not to do philosophy before they're 30

because the young line to him does not have the kind of practical wisdom to to know which ideas are worth pursuing and which ideas aren't. Do you think you're a greater philosopher in in any sense of

the word after going through Guidewire?

Uh I've had occasion to reread things that I had read, you know, when I was younger and they have a deeper resonance to me. Um because, you know, having

to me. Um because, you know, having encountered the world or wrestled with the world, so to speak. Albert Hirchman,

he wrote this book called Reason, Voice, and Loyalty or >> Loyalty, Voice, and Reason. I can't

remember. Uh but it's it's it's it's actually more a work of like organizational psychology. I had read it

organizational psychology. I had read it when I was I don't know aun 18-year-old.

And what did I know? I'd never been part of any organization. I'd just been a student my whole life. And now many years decades later, you know, I had run an organization that had 3,500 employees and and it had a completely different

character to me. One of my favorite, it's not even philosophy. It's it's a preface to philosophy in philosophical explanations by Robert Nosik. Oh, so he he talks about his own journey as a philosopher and how there was a point

when he thought the purpose of philosophy was to make arguments so powerful just so irresistible that if you didn't accept them then you were not dead like there was something your your

brain would malfunction because you would have accepted you know a and not a at the same time right and like that was the goal like you know to make arguments that strong right and you know I read

that when I was in undergrad and I said that's you know he was talking about how he evolved from that perspective, but he that was such an exhilarating idea. Like

that's kind of how I thought about >> Right. It's a gladatorial combat. Knock

>> Right. It's a gladatorial combat. Knock

them dead. Yeah.

>> Exactly. With arguments and cross-examination was a big part of that. You highlight their inconsistency,

that. You highlight their inconsistency, their incoherence.

>> And you know, as you get older and you realize that you never really persuade anybody of anything. Not only do you knock knock them dead, you don't even change their minds. And I I try to think

like, have I ever in my in all my years of discussions with people, have I ever really changed someone's mind? And I

realized probably not. I don't know. I

can't think of any. Um

>> I'm not even sure that's how philosophers work.

>> I don't know. Um so anyway, I I think the beauty of of a relationship with a written one is that you get to re-encounter. You get to return to

re-encounter. You get to return to something and it it it casts an it has an echo. It it has a reverberation that

an echo. It it has a reverberation that kind of brings you back into a re-enccounter with your younger self, your younger mind. And it it brings a kind of self-nowledge. And if right, >> if you don't if you don't have a relationship with the written word, you

don't you don't get that. You don't have that chance to to experience that that reverberation, that inner voice, >> so to speak. And I again, what a what a profound gift to have had the education I had.

>> That's so interesting. It's almost

for you to have read certain important books when you were young.

>> That's right. is to have your own soul to be deposited there. That's right. And

then when you pick it up again when you're old, you're encountering not just the book, but yourself in some way.

>> In fact, we were talking about Hegel, you know, I I actually recently picked up The Phenomenology of Spirit again, which I read as an under I mean, it's a punishingly difficult book. I mean, if you don't I don't know if >> the writing doesn't help.

>> Oh my god, it's incredibly hard and obscure weird book to read. And I found it myself able to read it very fluently now.

>> Wow. I was like it actually things that had seemed so difficult and dense and I was I was so pleased by that but it showed that some it would have been kind of an unlock that somehow my life experiences had unlocked >> right

>> things that had been obscure before.

What I find most remarkable about your transition was not just the skills you you had to relearn, but the type of character like how different the hyperttracted academic is.

>> Yeah.

>> From the Silicon Valley entrepreneur, right? You have like thinking versus

right? You have like thinking versus action. You the bureaucratic versus the

action. You the bureaucratic versus the highly agential.

>> You kind of the absent-minded like slow thinking and the hyperquick and practical. You have the patient versus

practical. You have the patient versus the urgent. Mhm.

the urgent. Mhm.

>> So what enabled your character >> to succeed in both of these domains that requires polar opposite traits?

>> Yeah. Well, I think the universal, if I had one, and this sounds too flattering to myself, but you know, it was this ambition like I I I need to succeed.

>> That was the core. And so you were willing to transform all the other parts of yourself to fit.

>> That's right. It was the necessity. It

was the power of necessity. And again, I have such a gratitude for this. I think

a life spent >> that never encounters the edge of necessity, the edge of of potentially catastrophic failure. Um, a kind of a

catastrophic failure. Um, a kind of a sense that you've made serious promises to people that you've pledged your honor to something succeeding that you have you've you've you've invested you've injected it with your identity even to

say I am an entrepreneur. I am the founder of this company and if it fails then I have failed. I am a failure in some way. Like to have lived a life

some way. Like to have lived a life without having done that is somehow a little bit lesser in I don't mean morally lesser.

>> Yeah.

>> I just mean >> less full or something >> like less full a little like hasn't hasn't seen or done something that's very important >> when you gain the traits of entrepreneur. It sounds like for example

entrepreneur. It sounds like for example at least for deep thinking >> you kind of lose. It's not a Hegelian gain. It's not like you're able to

gain. It's not like you're able to subsume both under you. No. It's it was a switch.

>> It's a switch. It's a switch. Yes. And

you have to cut off your reasoning, you know, shorter. You don't get to write

know, shorter. You don't get to write long inductive argument for why we ought to go east instead of west.

>> No, you have to act. You have to have a predisposition to act. You have to get on the plane. You have to you have to sell that sell that customer.

>> Um, >> and I I'm I'm just grateful to had a life that had both of these. They had

both right?

>> You know, that had more time for contemplation than most people have had.

And then a life, you know, characterized by very intense action. And I hope in this chapter maybe maybe something that's a little bit >> okay so maybe there is a Hegelian conclusion to this right where you were

just philosopher you were just king and now maybe you're you're able to combine these aspects >> that's a that's a very flattering way to put what I aspire to do now I mean I am I am a venture capitalist but I and it's important to generate good returns and I

I'm just as ambitious so I have the same ambition to do this job well but the the mean the way in which I want to do it well I think is by unlocking for a

certain set of a certain set of founders um their best selves, their their their best capacities and that's by being their ally. That is by um asking the

their ally. That is by um asking the right kind of provocations but in a way that's that help that's helping their reasoning process to come to a conclusion and maybe that's too grandiose but that is that's my

aspiration and to live a bit vicariously through other people going through what I went through. So this is another quote from you to describe why you weren't content at McKenzie.

>> I was resistant to having a boss and had unreasonable confidence in my own ideas.

>> What this reminded me of was kind of the difference between the thinker and the scholar.

>> I think what the thinker is to the scholar, the founder is the employee.

>> In the sense that uh the former, the thinker and the founder, they're kind of >> mavericks. And if you judge them on the

>> mavericks. And if you judge them on the basis of an employee or a scholar, they're actually quite bad. Yes. Like

nature is a pretty terrible scholar at least in his later works. I mean, he was he had a great early scholarly careerist. Yes.

careerist. Yes.

>> But it was precisely because his willingness to ignore those scholarly conventions that made him a great thinker.

>> Yeah.

>> And so >> my question for you is clearly in this founder employee path, you chose the founder path. Do you think had you gone

founder path. Do you think had you gone down the academic path, >> would you have kept that kind of maverick tendency and become a thinker instead of a scholar? Yeah, I I think in

my own psychological self diagnosis I I had a unreasonable unwarranted expectation that I should be in charge

that I that my ideas were better that I couldn't bear to work. I think I inherited this from my father by the way you know he was a professor himself. uh

he was a sociologist not a not a philosopher but you know he he struggled with department chairs and and university administration and so forth

because he was always exasperated by that but yes I I chafed all the time uh at the idea that someone would would tell me not that I knew it knew the right answer I just couldn't I just didn't want to do it on someone else's

terms >> I didn't want to do it at their behest I didn't want my contribution to make that person more glorious >> and you know the best employees are ones I read this somewhere. You know, they're the ones that

>> internalize their superior, their boss's objectives and as their own.

>> Yeah.

>> But I couldn't do that. I was just incapable of it.

>> And that maybe more than anything else drove me to the entrepreneurial path.

>> Um and there that's why again the subtitle of the book that I have yet to write um is, >> you know, a founder is not an employee and a startup is not a company.

>> A thinker is not a scholar. A thinker is not a scholar. Yeah.

>> Exactly.

>> A startup is a company, but I'm saying it's not a company. Like none of the other conventions or characteristics of a company apply to a true startup, >> right?

>> Of course, a founder is an employee.

He's paid a salary, etc., right?

>> But they he is not an employee in in the constitutive sense.

>> Or even more strongly, the same things that would make one a good employee would make them a bad founder.

>> Same thing to think in the scholar.

Okay that's >> so you described your unreasonable confidence.

>> Yes.

>> And I'm going to cross-examine you because you also described your kind of perpetual insecurity. Here's another

perpetual insecurity. Here's another quote. I have a hole inside of me that

quote. I have a hole inside of me that can't be filled. The founders that I am personally drawn to as an investor are also perpetually insecure.

>> Yes.

>> Two questions. Number one, why are you perpetually insecure? And number two,

perpetually insecure? And number two, how do you reconcile that with your, you know, unreasonable confidence?

>> Well, I think anyone who has a kind of self-awareness, anyone who has a knowledge of what's preceded him, you know, should be should have an insecurity. when you consider the

insecurity. when you consider the vastness of this world, the vastness of human achievement and the accomplishments, you know, just forget just in the in the commercial world, you know, not to speak of the the academic

or the philosophical world, you know, it's it takes incredible sarity to say, I'm I'm going to move the earth here.

I'm going to add something that's genuinely novel. Philosophy is

genuinely novel. Philosophy is particularly humbling in this way. I

imagine that mathematics would be something similar like this where you know there's this again this vast edifice of of achievement that has been so polished by so many generations of of

contemplation the it takes what kind of audacity it takes to say I will observe something that no one else has noticed anyone who doesn't approach that with with with

insecurity is um is just ignorant right um on the other hand um there is a kind of confidence in and that comes from looking around and saying look at others

who were doing this and and look at the kind of the rashness the recklessness the inconsiderate the incoherent way in which they're approaching this problem surely we can do better

>> and I would say we had both of those attributes in you know us as a founding team >> on the one hand we said like it's we we we actually recited this almost like a mantra this company's never going public

right none of us are going to become billionaires out of this thing um we we'll never be a household old name, no one's going to know it. We're just going to try to build software like a craft and and make our customers successful and build something of value and how

that monetizes and how we're rewarded for it. That's that's a a subject for

for it. That's that's a a subject for another day, right? So, we brought that kind of humility to it. At the same time, we did bring a kind of swagger because we said, "Look at these clowns who have started the companies that we

used to work at. Look at all these other would-be entrepreneurs. Look how

would-be entrepreneurs. Look how wasteful they are. Look how shallow their reasoning is." Right? Um and

surely we're going to do better. So we

had both. I think there's actually a correlary in philosophy as well where on one hand you stand next to these giants you're like but on the other hand like even some of the greats have the most

simple like of errors of course >> in their argument and so so that on one hand is almost a generation of insecurity but also an invitation to to join their ranks. Yeah,

>> that's a good point. Yeah, I mean even the greatest philosophical works there are these moments >> ridiculous just absurd. I mean even in Kant there are parts that are like this is it's It's it's it's a joke. I mean,

you should not tell a lie even to prevent a murderer from coming and killing your friend because that would be somehow self-contradictory. And you

said, "How could anybody possibly who claims to be a moral philosopher come to that conclusion, let alone the greatest moral or one of the greatest moral philosophers of all time? It's just so idiotic." So, you're right. Uh you have

idiotic." So, you're right. Uh you have to actually treasure those moments because they suggest we're all fallible >> or it's an invitation.

>> Yes.

>> So, did your successes at Guidewire fill this hole?

>> It's a good question. um say yes and no.

So on the one hand yes uh it it it satisfied something that I it was so improbable that we would succeed and we had and in in the most un unmistakable

terms on the other hand I'm deeply unsatisfied. your company should be much

unsatisfied. your company should be much better than it is now because what happens your horizon opens you you achieve >> you see the next level >> you see the next summit the next summit comes into view and I recognize you know

the guyar today has a billion one or you know a billion two in revenue that's that puts it in a pretty elite company there very few ventureback companies that ever get to anything close to that

scale but it should be it should be 5 billion it can it it's it um it has that opportunity I no longer lead the company and that's that's a it's a source of

sometimes some sadness to me. But um I am not fully satisfied and and if you're an ambitious person and you work in a place as intensely competitive as as Silicon Valley and the venture

ecosystem, you're around people who are at all all levels of success and it's like a like a fractal there. There's

just there people who are orders of magnitude more successful and orders of magnitude more successful than that. And

so if you are comp if you are constituted as I am right and you spend time with people like that then you cannot resist a kind of comparative

kind of comparative tug and a sense I ought to have done more. I ought to I ought to be able to achieve more. I

ought to have achieved more. And I I guess we have to I have to I choose us to embrace that as a kind of life force as opposed to um you know just a way to make myself unhappy all the time.

>> Right. But when you talk about the you know if I don't do this it's over will I be a failure is that gone >> indeed it is indeed it is yes and so the one thing I am I'm most

>> success works apparently like external successes work contra the stoics >> you know there's a moment in marks uh I I guess it's like in the I think it's in the first or second volume of capital when you know he says the the whole of

human history is essentially the effort to rest freedom from necessity right and um you know even as our needs have expanded there is still you know our needs expand but they don't they've not expanded to

infinity and uh we have to find freedom and that requires a shortening of the working day right so he he ultimately did ground this idea of what it is to be free and like saying we need a certain amount of leisure a certain there's a

certain foundational um core that on top of which now we can start to be free creatures but we're not just beasts of burden and in a sense I I gotten to experience that I've gotten to

experience to kind of clear a certain threshold and call it financial freedom.

It's a place where um life does not have a quality of just continuous necessity and uh and that that transition that's just a binary moment. I mean it's not a specific moment in time but it's a

binary state of mind um is glorious and there is nothing I could possibly consume. There is no pleasure, no no

consume. There is no pleasure, no no food, no experience, no object I could possibly buy that would have anything like the reward as having crossed that threshold.

>> And sorry, just to be clear, do you mean having built a deck of corn or do you mean having the money in your bank account that it gives you freedom from necessity? It's the latter but it is

necessity? It's the latter but it is having said that there is a kind of floor to the accomplishment that is that that that unlocked that one unlocked the

other and as a result >> I no longer there is the kind of abyss of possible failure you know >> but if you had just won a lottery and had the money in bank account that

wouldn't do that >> so so it's both having but also if you lost all that money someone stole it all away that would also >> yeah but it's like it's to arrest wrestled the world and succeeded to some

measure that then you know allowed a kind of liberation from the you know basically you know the kind of material constraints that that I had grown up with and that you know that my family had grown up in there's no return from

that um but that said >> there is a return right if you lose the money >> yes right if I if I were to be reckless or extremely unlucky but um uh but outside of that I still ambition

continues it doesn't continue with quite the same I wouldn't say I would say the intensity is just as great. It doesn't

have the same kind of desperate character, fearful character.

>> I mean, this is how I would describe one of my changes, which is I went from trying to minimize the negative to pursuing the positive. And that's a much better way to live.

>> Indeed. Indeed. Uh it's or as some say like an austerity versus an abundance kind of mindset. It's very interesting because many philosophical approaches to this kind of gaping hole inside of us

>> is to want to sort of resolve the hole.

>> But from what you just said kind of filling the hole with like actual external achievements also work >> indeed. Yeah. Well, I mean well I mean

>> indeed. Yeah. Well, I mean well I mean nature called it a will to power. Um and

it meant it was never satisfied. The

will to power isn't there's not some moment where it's over.

>> But the character of it changes is >> Yeah. the character of it changes and

>> Yeah. the character of it changes and and it goes from being the fearfulness of it disappeared and for that I'm I'm profoundly grateful.

>> Yeah.

>> Yeah.

>> We talked about the relationship between contemplation and action in your own life.

>> Now I want to first just talk about contemplation and then talk fully about Guidewire. So give us an overview of

Guidewire. So give us an overview of your early life and how you got into philosophy and eventually went to Princeton and Austin.

>> So I was uh I was one of two kids. Uh I

I grew up in Maryland. My my parents were were they were first generation Korean immigrants. You know, I wasn't a

Korean immigrants. You know, I wasn't a social misfit, radical social misfit or anything, but I was I was much more inward-looking and I discover because my father was my parents were very well educated and he was a professor, you

know, discovered the world of ideas perhaps earlier than most. There was a moment when I um well I during this during the breaks I had at uh at

university, I said I chose those as like extra time where I got to study more, I got to read more outside of without the pressure of a class. Um that's how serious a student I was. And I had this feeling as an undergrad that as you get

exposed to the world of ideas and you see just how vast it is, just how much there is to read, right? I said, I need to catch up. I need to ingest this kind of this cannon. I have to I had to be

conversant in this corpus of And so, uh, there was this opportunity at this one Harvard bookstore that was going out of out of business that you had it was a certain um if you had under the right conditions, you could go and you could

basically buy $500 worth of books for for $200. And I, you know, I took a bus

for $200. And I, you know, I took a bus and I, you know, loaded up multiple duffel bags with all of these like canonical works and um and, you know, I

was, I think back to that time with such amusement because how earnest I was, how earnest I felt like this was the most important thing in the world was to read these books and to and to be to be a

serious scholar. It's what it was going

serious scholar. It's what it was going to take. And um you know I I I love that

to take. And um you know I I I love that young man that you know that that was so full of so full of drive and earnestness at that point even though you know he became someone else.

>> See so you described um the experience of growing up as a minority >> and for me >> I spent most of my formative years in China where I was not a minority and then when I moved over here I was I

became a minority. Um, and so for those first early years, um, if I'm being honest with myself, a lot of my motivation to do well both in school as

well as in my career was a kind of >> I wouldn't say frustrated romantic drive, but a desire to be better in that domain to get like female attention.

>> Yes.

>> How much of your own early career drive both in the academy as well as in in in tech was due to that? Well, you know, I think being an Asian-American male at in

that era was was a very fraught experience. um you know the the cultural

experience. um you know the the cultural exemplars of that time were you know when I say that time I mean the 80s let's say or the 80s and 90s were you

know were deeply emasculating um and were the Asian exemplars >> and you know many different Asian-American writers have have talked about this due to varying degrees of of

varying degrees of vulnerability but um that it is a kind of eraser the experience is a kind of that And you know one's romantic or sexual self is

it's it's constitutive of our charact you cannot you cannot forget it you cannot you cannot choose to to pretend it doesn't exist right and yet that was

kind of characteristic of the experience especially I speak as a male I I think there was a slightly different character to to being a female during that and I don't describe it as as oppressive it was just it just that was the particular

moment the particular cultural millio in which I lived um and So there was a sense for me and I think I think others like me to say these kinds of this this

whole domain is only one of kind of frustration. It's only one of

frustration. It's only one of frustration and pain. So therefore we we have toffect that that drive into into something that into a deferral that will

find its reward someplace else. So maybe

maybe far in the future. And that

ability to defer defer gratification um is uh a very very powerful cultural trait, a very powerful character trait if you can, you know, if you don't take it to extremes. And I think I would say

it's fair to say that I and my this is probably true of my brother as well who kind of like and true of many others of our generation really learned that and learned a kind of deep deferral that

that arguably turned out to be an asset later.

>> Yeah. because it it it forced you to direct through like you're like I can't compete in this domain now.

>> That's right.

>> So so I just have to I have to find another source of power and that power I'm not sure where where it will be and as we talked about through much of this conversation it was you know I'll excel in this institutional way. Ah but if

it's not that then I will excel then in the way that ultimately commands power which is you know which is wealth you know which is wealth and career success

right and um and you know it's we don't know ourselves we're mysteries to ourselves but when I say you know where did that where did the deepest drive come from the moments you know and I I

described it to you earlier as uh you know as a terror of failure but why was it so terrifying to fail >> because >> one of it was the romantic concerns >> that's right and that you could That was a kind of the second order question or

the the next question would be why where when's the terror, >> right? And it was that a sense that

>> right? And it was that a sense that everything was at stake, >> right?

>> Why was everything at stake? You could

have gotten another job. I you know >> I know but some I would have lost a certain quest for power. One of my professors had had I think one of the most interesting understandings of Rouso on Rouso on romance.

>> So Rouso believes that we uh have a desire to be the best. Mhm.

>> And obviously not everyone can satisfy this desire to be the best by definition uh for everyone. We can't all be LeBron.

>> Um however, Russo thinks one of the functions of marriage >> is to satisfy this desire by making you the best at least for someone if not a group.

>> Yeah.

>> Because when you marry someone or when you're in a monogous relationship, you say you are the best at least for me right now.

>> Yes. A correlary of this argument is that if you don't have the romantic intuition, you project that desire of being the best in another domain that that desire

remains unsatisfied. And so there's a

remains unsatisfied. And so there's a joke that I make which is um uh I I only like to invest in two types of founders, the the single and the unhappily married because those are the ones who who do

not have that desire to be the best fulfilled yet.

>> Um >> what what do you think about that?

There's there is some truth to that. The

desire for for that kind of recognition, for romantic recognition, it's incredibly powerful force. Um I would not say it was the animating force for me. Um

me. Um >> it was not >> well I wouldn't say it was consciously.

Marriage is one of the casualties of my entrepreneurial journey, you know, and uh I suffered that as a as a real failure. Um

failure. Um >> did you get married before you started?

at almost exactly at the same time as I started just by coincided at the same moment and um and then and then failed it failed later uh and I uh

however it has a very happy ending because I met ended up meeting the love of my life and she is now um a source of profound joy and a kind of love that I didn't know was possible and uh and

that's that's a gift that was completely unexpected at a at a at a stage in life when I not believe in such things. So

there's there's there's a possibility for wonder no matter how experienced and worldly you may feel that you are and I'm I'm testament to that. But um I think I think that starting a company is

is is such a demanding journey that it is very difficult it can't really compete with another kind of open-ended pursuit to like find to find one's life

partner. And I think if that's not

partner. And I think if that's not utterly stable, if that's not if if that I don't want to say anesthetized, I don't want to say because it's it's something that's much more constructive than that, then it's it's it's a it

makes it a very very arduous journey, maybe hard to the point of point of impossibility, >> right? I think.

>> right? I think.

>> Right. So in in your case, unhappily married, so I would have invested in you.

>> So okay. Well, tell us about finding love at an age where you you didn't believe in such things anymore.

>> Well, that's just serendipity. I mean,

it's just and there's no it's it's it's just a mystery. There's no explanation.

>> Ineffable. You can't That's right. I

mean, she and I often describe it as, you know, both of us are kind of atheist by nature and so forth, but I found a kind of religion and loving each other.

>> That's beautiful. Um

>> Princeton, >> yeah, >> you did a degree in philosophy and literature, the literature side. You

were exposed to postmodernism was the fad. Yes.

fad. Yes.

>> And you described to me how >> um today in our contemporary political environment you're seeing a emergence on of postmodernism but not on the left but on the right so tell us about that

>> well let's see so when when I was in an undergraduate in the let's say the early '9s um you know the the kind of the most there was a sort of radical wave intellectual wave uh that now seems like

ancient history of of kind of like postmodern thinking this is in this is in humanities departments across you know pretty much the whole country or you know and and it was you know a set of thinkers like Jacqu Derida Maurice

Blancho or most importantly like a Michelle Fuko that suggested things are not as they seem. Um that uh that the world is a text and this text can be

interpreted in ways that are radically different than the ways that our authors of those texts might have imagined them to be. that we can bring a kind of

to be. that we can bring a kind of interpretive lens to life, to text, to uh, you know, to the news, to history that um interprets it now on on

different dimensions of power, on dimensions of you know, of domination and hierarchy. The rest that are

and hierarchy. The rest that are radical, right? And um I found these

radical, right? And um I found these theories exhilarating when I was in in college >> because they're contrarian nature, their sort of ability to uncover things that are hidden.

>> That's right. a sense that you could rip a veil off of the the world to be steeped in postmodern theory, critical theory at that time. It felt like you had this weapon, this scalpel with which

you could interpret the world as a kind of kind of like radical ninja uh uh interpreter. No text, no idea, no

interpreter. No text, no idea, no narrative was safe from your ability to penetrate within it and see new ideas.

And it was a very exhilarating idea. Now

it led to some very crazy and incoherent places. The bizarre thing about this

places. The bizarre thing about this moment as I was as you alluded to our conversation about is that the people who are are saying the most who are taking saying the most outrageous things

who are the most distrustful conspiracy theory like um deconstruction of the world as we of the kind of coherent world that we know it are actually

tended are now found on the right.

Right. And they are ones that say that even things that kind of sacred texts like the constitution for example actually mean something different than

what we thought it meant and is uh and ideas that were kind of considered completely beyond the pale ought to be like reintroduced into the into the mainstream and are are worthy of you

know are worthy of serious consideration and that that there's a complete inversion of right like the the people that have been arguing on behalf of let's say greater diversity and equality

are actually the true oppressors. And

this kind of characteristic inversion of who we thought were the good guys and the bad guys. That kind of flip and making textual arguments for that is now seems to be in the province of the

right. And that to me is a a fascinating

right. And that to me is a a fascinating bewildering and completely unexpected development. My first foray into

development. My first foray into philosophy was a book called things hidden since the foundation of the world by Reneard Stanford professor. Um, and

as the title suggests, it's about uncovering things hidden since the foundation of the world. And there's

something so appealing to a young man, I suppose, of of like >> showing X to be not X or something.

Right. Exactly. Because it gives you as a as a young perhaps powerless man sense of power.

>> That's right.

>> That that I know I hold the keys.

Exactly.

>> To to the to.

>> So, for example, in like in in discipline and punish, you know, Fuko's most famous work, he says the school, what is a school? It looks like it's a it's an institution for edification and for elevation. No, a school is an

for elevation. No, a school is an institution for domination, right? For

oppression and for indoctrination, right? And you know, when you're a young

right? And you know, when you're a young person, that idea is exhilarating that as a as a rebellious teen makes somehow seems very true, >> right? And it gives you a kind of power

>> right? And it gives you a kind of power to say whatever you may tell me about the way the world really works, >> I know this, >> I can unlock it. I can unlock it and I have a set of tools to

>> expose its hypocrisy, etc. How did you grow out of that phase?

>> We realized the kind of pointlessness of that. So first of all um and this was

that. So first of all um and this was this was part of my um swerve away from the academic world I think was realizing the kind of the impetence and the kind

of ultimately the pointlessness of these readings these deconstructive readings right like you could >> I see you can you just do do them infinitely and nothing happens.

>> Exactly. And the greatest of the postmodern thinkers at the time Dered die himself said like what is the point of theory? And he one point he said it's

of theory? And he one point he said it's like play. It's endless play. You just

like play. It's endless play. You just

you just kind of dance from text to text and you have these, you know, observation, but there's no there's no point of resolution. There's no you don't arrive at any truth. You just, you know, you just dance and bounce. You

ricochet off of that to make the next pathy observation, right? Um, and you realize, wait a minute, does anyone actually care? Like you, you know, you

actually care? Like you, you know, you have these scintillating terms of expression and these kind of witty reposts and so forth, but ultimately it's it's it's imp right. Well, you

described your turn away from postmodernism as the same move of your turning away from academy to industry.

But before that, you went to Oxford, which was a heavily analytical department, and you wrote your your thesis, I believe, on Wickstein mostly.

So, there was already a turn away from that before you left.

>> That's right. When I went to Oxford, it was the first time I was really intellectually humbled, you know. Oh,

yeah. Absolutely. because um

>> so so much more competitive than Princeton or was it because of the graduate versus the bachelor degree or >> it's not that it was more competitive is that spec it's actually I wouldn't say Oxford is generally that way but the the particular BIL philosophy program is a

very serious one and it's done in a particular kind of analytic philosophical tradition and as we were as and in that that kind of philosophical tradition prioritizes

lucidity clarity and you know novelty of argument in areas that have been very thoroughly explored and so to I I found it difficult. Um I was there and the

it difficult. Um I was there and the kind of rigor of trying to write a good thoughtful term paper on subjects that were very very thoroughly explored by by many thinkers beforehand and under the

withering cross-examination of of a tutor there was like was hard. I found

it hard but I decided like this is this is serious philosophy like that was and I had read works in the analytic tradition before but like this was all that was done and it was it was it was serious and the other students in the

program they were all intended to be professional philosophers or at least at that moment and many of them went on to be and I I had to take it very seriously and it was it was very good for me.

>> So what did you end up writing your dissertation on? which specific part

dissertation on? which specific part about Wickenstein >> philosophy of mind and and the problem of free will uh as understood by Vickenstein and and he didn't Vickenstein didn't really talk much

about free free will >> um he but there's not much doubt that what he thought about it was very similar to what he thought about um most topics which were that there was a confusion of language that you know he

he talked about one of his most famous expressions is that you know philosophy is a bit of bewitchment of the intellect by language right and so that the goal philosophy is generally not to solve problems. It's to diagnose the way that

we've gotten entangled in the situation.

>> Dispose of the question itself.

>> Yeah. You say like you you thought that there was a problem. There actually

wasn't. Let me untangle you from this situation and you'll realize there was nothing to have worried about in the first place. That's essentially the

first place. That's essentially the objective of philosophy for the for later Vickingstein. And um and so I the

later Vickingstein. And um and so I the dissertation was an inquiry is like does that really work for the the most intractable problems that we intuitively feel about you know about the freedom of

our about our actual first person agency and about the existence of our mind you know and subjective experience does this kind of total pragmatic >> um attempt to dissolve the problem is it

is it persuasive in the two most important questions that we encounter right >> and I >> what was the conclusion I say no ultimately, you know, even though I think he's he's the philosopher that I

return the most to in thinking about, you know, about the the questions that puzzle me.

>> I mean, if the Wikinsteinian kind of dissolvement of the question itself doesn't work for these most important questions. Do you find it works for

questions. Do you find it works for slightly less important questions? Is

that why you return to >> Wenstein? a lot of questions in

>> Wenstein? a lot of questions in philosophy that that kind of arise when you when you push an intuition to a place where it gets to kind of like a skeptical boundary, right? So, you know, for example, you know, pain like he has

his famous discussion of pain, it's like, well, when I say that I'm in pain and you say that you're in pain, I cannot feel your pain and you cannot feel my pain. So, how do we know that we're talking about the same thing? And

he has a famous uh metaphor that says like like it's like we both had a little box and it was like a little beetle in it and when I say pain I I like look inside. It's like that's that's that's

inside. It's like that's that's that's mine and you have your own. He says is this the right characterization of what we mean when we say that pain is an internal experience and he says what do we really mean by the word pain? How do

we use the word pain? And you know he kind of dissolves that question essentially that that's not that's the pain is not that word and it's is not just a reference to a particular private

experience. it that word is a human

experience. it that word is a human artifact that exists in a a kind of communicative context and overall he was trying to dissolve this idea that language maps to and there's like a

mapping relationship between language and the world >> which was his early idea >> which was the earliest idea right and instead that the language is this it's a practice is a kind of pragmatic practice that's a very very shallow

characterization of it but that's the single idea if you were to put it in the sentence >> right >> um so so your claim is that It does work for lesser philosophical questions. Yes.

But not for the most important with philosophy of mind and free will.

>> Yes. Or at least it does not lead to the kind of tranquility that he seems to think is the objective where you're not bothered by this question anymore.

Right. Like I remain very bothered by these questions. And I think anyone who

these questions. And I think anyone who anyone who's really thinks about this question of the freedom of the will or what does it mean that my mind that I have a subjective

consciousness anchored in a physical physical body? If you really reflect on

physical body? If you really reflect on these questions for any duration of time with any seriousness, the deep weirdness of it, >> yeah, >> does not escape. You never leave it. I

mean, it's it it remains weird, at least for me.

>> Does Wilkinson help in any way? Like

what what's the best thing that he would say and like like does it I know you don't find it ultimately satisfying, but >> yeah. Um certain ways that we can kind

>> yeah. Um certain ways that we can kind of overly raify or like like uh say like well there's something called the will, right? And like do we have this thing

right? And like do we have this thing called the will and that that that usually leads to the wrong place because it's an ef the there's not like one thing there's

not one object that has a reference that is at the heart of a problem.

>> Right. It's

>> there's not a platonic will that we're trying to understand the characteristic of.

>> Yes. Exactly. or you know or there's and he says it's about many of the ideas that we can that we can easily raify like the good the right you know um you know the mind right

>> we should attend more to the practices of what's what do we mean by >> how do we use the word mind right >> right and like when when do we under what situations do we ascribe a mind to

other things what what do we really mean by that word it's not a mysterious thing that we are trying to explore and get to and your response is that helps with the

most exaggerated forms of raification.

But the question still stands like how does my subjective experience work in this in this in this >> in this materialist world. Yes. How can

it be? How can and that's >> that it does not dissolve that question.

>> I see.

>> Yeah.

>> One of Wukenstein's projects um to put it very simply is an end of philosophy.

>> Um kind of like the way that the ancient skeptics, you know, wanted to produce a kind of tranquility through suspension of judgment.

>> Yeah. Um,

>> can I read you your dissertation on Wickenstein >> as causal to your leave of philosophy in some way?

>> I don't think so. I think the reasons that I ultimately left the academic world were much more >> were much more ordinary. You know, they were a worry about what kind of life I would get to lead about what kind of

power I would have what kind of status and and my ability to to make good on a sense of expect a set of expectations that my family had of me. And um it was very surprising. My my parents were

very surprising. My my parents were shocked that I went to the business world. They were dismayed.

world. They were dismayed.

>> Why?

>> They were dismayed. They did not understand the world of commerce >> because they were academics themselves.

>> They just thought that I was best suited to be a student. I mean to be a a scholar to be in the academic world and I was and they wanted me to s to do what I would be good at. And they were horrified that I would now try to be a

salesman or something. And I am a salesman. I don't look much like a

salesman. I don't look much like a salesman. don't really speak like one

salesman. don't really speak like one but I I describe myself as a salesman with pride right but my my parents were dismayed by that uh they came around um

but uh they they were really they were shocked >> let me try to push you one more time here Wikinstein I believe for a lot of his uh students I think at Cambridge he

encouraged them to go to trade >> partially because of his um I I wouldn't say like looking down upon philosophy But thinking a lot of the philosophical questions are kind of you know the

philosophers tying themselves into into their own >> knots. Yeah that's right.

>> knots. Yeah that's right.

>> So I totally hear you that your concerns were a lot more practical instrumental >> but surely studying Wiganstein for 3 years must have also devalued your your

opinion of philosophy a lot lot more especially academic philosophy. Is there

is there something there?

>> That's right. And I came to admire other pursuits more like I found a kind of um admiration or you could even call it fetish of people who studied like the really pure technical fields like especially math and physics. Yeah.

>> You know and I recognized I had perhaps under different circumstances with more focus I could have ended up becoming studying those but I didn't >> and I had chosen the path of the humanities >> during the def during Wigenstein you had

a greater appreciation for math and physics.

>> That's right. or I mean that has it started earlier than that and said you know if I'm like like wow this is this is this is serious work and this is a little bit more I don't know >> wishy-washy

>> yeah a little bit a little more murvatory or whatever like and um and the bigger concern was can I really be great at this can I be good at this I I can spend I can imagine spending decades

in in pleasurable contemplation and writing this and dialogue with but can I be really great at this and I got to see great when I was at Oxford Thomas Nagel came and he led seminar Derek Parett and

you know a number of other very very luminary philosophers and I realized this is an elite group of incredibly brilliant people and it's not that it's a comp it's not that it's radically

improbable that I could ever be one of them uh but it's a long journey it's a long monastic journey >> where do you think you got this sort of need to win >> I had a happy childhood but one that

that had a sense that it was in preparation for something larger or something for something more there was still a struggle ahead had a kind of generational struggle ahead to make to make a good life in this country that was that wasn't there in the first

effort you know that there was that there had been a lot of sacrifice my mother would say to me you know not to make me feel guilty just just to confide in me she said you know I left everything that was familiar to me

everything everything that I knew and I I saw that she was kind of a stranger in a strange land in this she actually spoke very good English but she never understood American customs she never understood American practices and she

tried so hard you know, she would subscribe to Better Homes and Garden and try to make pineapple upside down cake and, you know, and liver casserole, watch my little league baseball games.

And she tried so hard to be American, but the gap was wide. It was very wide.

And I had a sense of accountability to her. Like, she came here because she

her. Like, she came here because she wanted something better for for me. And

I um and and it was not just her. It was

multiplied across a larger extended family that said, "You're the hope.

You're the hope." They didn't even say those words to me, but I thought >> it was it was implant. Yeah. I I

definitely definitely relate to that as well as a basically like a like a firstgen uh as well. We talked about your philosophical journey and your philosophical views. Now I want to dive

philosophical views. Now I want to dive deeper into your guidewire journey.

>> Sure.

>> And let's begin with uh this idea tunneling through granite. Tell us about that. It was a way of framing our the

that. It was a way of framing our the company's journey and its task as one without shortcuts and to say we there's difficulty ahead and you know when you're trying to get around the

mountains maybe you'll find a pass a secret passageway you know maybe you'll find a way not to have to cross it and we are for better or worse we are embracing the necessity of of going

straight through and that's our strategy it's a full frontal assault on the hardest pet problem and it will be very very hard But we our reward will be you know that it's harder for anyone else

who may follow and you know the the reward of its completion.

>> But when someone asked you what's on the other side of the granite, you said more granite.

>> Yeah. Well, that was the joke always because uh was like so what's on the other side of this granite? And I said there there's no other side. It's

infinite granite. It's all there is. So

therefore, in this kind of stoic sense, you must enjoy the tunneling.

>> Right? That's what I have.

>> Isn't that a form of masochism? Like

like to confuse the difficult with the good. Well, the massochist fetishizes

good. Well, the massochist fetishizes the difficulty. The fetish finds

the difficulty. The fetish finds pleasure in difficulty for its own sake.

Seeks out difficulty because it's pleasurable, >> right?

>> That's not that's different from an embrace of difficulty.

An embrace is not the same as a fetish.

An embrace is saying this is what's this is what is necessary. We're going to do what is necessary, >> you know? And I think it's different.

>> Have you heard of the the Chinese parableish?

>> No.

>> So, there's an exact Chinese parable about someone tunnling through granite to move a mountain. Is that right?

>> And and uh uh I mean the long short of it is he's like I'm going to move this mountain. And then he's like, "Well,

mountain. And then he's like, "Well, you're never going to move this mountain because you can only get a bucket of rocks like you know every day." And he's like, "Oh, I can't, but my my my my sons can and their sons can and their sons can eventually will be moved." And it's

a happy ending because eventually the gods are sort of so moved that they >> they do it on their behalf.

>> There is something else that was part of the message which was the incre like embrace that incrementalism. embrace is

that like today we can we will just take steps in the right direction and tomorrow we will take more steps in that direction and over time just like on a long journey you look back and you say look at the distance we've traversed

right that's the only thing you can do so many of the the traits that I uncovered about you I see in myself whether it's the sort of work ethic it's the sort of zero to one hyper commitment

or all or nothing the overachiever the desire to sort of work on hard problems that you tunnel a little bit on rather than, you know, try to come up with like a one brilliant insight that kind of changes everything.

>> How much of this do you think has to deal with, >> I guess, not your East Asian upbringing, but but your family sort of East Asian environment that you were brought up in?

Americans have certain notions about uh about Asians because uh that that sometimes are distorted because what they see is a particular demographic slice of of Asia that under because of

the immigration rules and other things that were happening in each of those countries at a certain time came over here. I don't associate the kind of this

here. I don't associate the kind of this kind of stver insecure overachiever intensity to being Asian as such as to being is the immigrant to being the outsider

>> and to coming coming to a place where to chart some other path to success because the conventional ones are not going to be given to you including romantically I think which is which is a factor um and

uh it was certainly true for me it was certainly true I wanted to succeed because I felt I had I had started at a disadvantage And um not I didn't bear any animist towards anyone for that. I didn't feel

like that was unfair.

>> I just felt like that was the truth of it. And um and therefore it was it was

it. And um and therefore it was it was it was going to take more.

>> You described company building as a niche enterprise.

>> Oh yeah.

>> That is at once both heroic and tragic.

So tell us about that.

>> Well, you know it's heroic uh because you are doing something very audacious.

you're proceeding with huge numbers of unknowns and you're bearing it a massive amount of that risk, you know, on yourself, right? And that ought to be

yourself, right? And that ought to be rewarded and it's a beautiful thing that it is rewarded, right? So that that part's heroic, but there's um, you know, there there are tragic aspects as well.

And the the most tragic thing is you have bound yourself to something that may go horribly wrong, you know, that is open-ended in its nature, that you are making promises to people that you may

disappoint, um, including to yourself, right? And that is that can that can

right? And that is that can that can have a tragic quality and I've seen that as well where entrepreneurs they feel that is their destiny that they're and

they become addicted even to the certain qualities that you that certain characteristic experiences of entrepreneurship right one of those is that you get to set the agenda. So in

any company, regardless of whether it's doing well or doing poorly, uh when you're the CEO, you are lord of the realm. And that is a certain feeling,

realm. And that is a certain feeling, right? Um and some people just always

right? Um and some people just always want to do that. They just want to do it relentlessly over and over again, even when they don't have the chops.

>> Yeah. When they're not they're not they're not actually cut out for it in the other ways. And that can be really tragic. Um

tragic. Um >> Right. Because it's their fatal

>> Right. Because it's their fatal character flaw that sort of That's right.

>> keeps them coming back to this. Right.

There's another aspect of tragedy that I can speak to personally, which is that you you you leave something of yourself in in this enterprise that you don't always control. In my case, I do not

always control. In my case, I do not control my my company. I I had I didn't have the assets. I was one of a large founding group. I was naive. Um the

founding group. I was naive. Um the

balance of power was very much in the favor of investors. And so, you know, I don't have I didn't have control of the company. Even when it went public, I

company. Even when it went public, I had, you know, I had very modest ownership of it. The thing that I had poured myself in that I think in many respects bears some of my personhood is

embedded in that company. It is now divorced for me. I cannot recover it. It

is >> it is in the world. It it I I made many promises on its behalf but I no longer control it.

>> It's both you and not you. And the

tension there is what creates the tragedy.

>> Sra talks about it as well. He talks

about your shadow that the other that there is yourself as you as you experience it in the first person but then there is as you are seen by by by the other that sees you and it's it kind of attaches to you as a as a shadow this

appendage that you don't get to control that's just like linked to you.

>> Yeah. And um

>> so this company forever I mean especially as I'm in the professional world I am associated with it. I am very powerfully associated with something that I is no longer being and I have a

sadness about that.

Um, do you enjoy the actual day-to-day of running a company? The reason I asked this is because >> when I was making the decision of to to leave the company that I that I you know helped start and return back into

contemplation, >> the calculus was this and it was a no-brainer once I frame it this way.

>> Building this company, even if I win, I lose.

>> Yeah.

>> Even if I spend all of my 20s, this becomes a deck of corn.

>> We all become fabulously rich. There's

something about not spending my most vivaceious years on something I know I love because the day-to-day I don't actually love that much.

>> Yep.

>> will be a failure. What I'm doing now and I genuinely feel this way. Even if I lose, I win. Even if after two years I run out of all my funding, you know, no one watches my stuff. The fact that we get to have this conversation, this is the reward.

>> It's beautiful.

>> And so, so I I've turned around what success has meant from this kind of deferral. this

um and again I would say it's a very East Asian kind of kind of trait this ability to defer sometimes multigenerationally to a much more perhaps western kind of like just want to live like I just want to like the the moments I'm living.

Yeah, >> that's a beautiful thing and I I I really commend and admire that you've you found that in life and you know there are pursuits in life that are like that. I'm a pianist and I get to play

that. I'm a pianist and I get to play works of exquisite beauty and whether or not I become great at it or become famous and get to perform at Carnegie Hall, I get to do that and that's that's its own intrinsic inner reward. A

company is not like that. A company the entrepreneurial journey is not like that. It does not

that. It does not >> is it like that for anyone or No, >> I don't think so. No, I mean it has it's it has characteristic rewards that are not just about commercial success. But

it it's not you cannot just say I'm doing this company because >> I like board meetings.

>> Exactly. A company is the reward is the company's success. It is its flourishing

company's success. It is its flourishing and it is its growth. Actually along the way you know sometimes employees would say why do we have to grow so much like like you know when we grow we have to bring in new people. they may not share

our values. It gets complicated like you

our values. It gets complicated like you know like why do we have to grow? And I would I my answer was always the same. There's only

two kinds of companies. Uh those that grow and the other kind there's no other choice. There's no there's no that's

choice. There's no there's no that's just stasis and stasis is death. So we

have to we have to and that and that just the imperative of that is is exhausting but is there's no escape from that otherwise find some other be a pianist or a philosopher. um that you I

think you were asking did I enjoy >> enjoy that did it dayto-day. Yeah,

>> a lot of it I did enjoy. There was a part that I detested and that I would do very differently and I it's one of my regrets and the part that I really detested was the travel you know selling

was such a important part of the job and the nature of what we built was that it was a very consequential decision for any of our customers to buy it. they had

to they were taking enormous career risk. Um it was enormous capital risk to

risk. Um it was enormous capital risk to buy and not just what they paid us but the the whole transformation project that it would take to implement the software and all the business change that would have to go along with it. And

so it was very personal. The sales were very personal. I I at a certain point I

very personal. I I at a certain point I as the principal in the company would have to tell the buyer or the other individuals that were that were influencing the decision to say I pledge

my my honor my company's honor to the success of this project. We will not let it fail. We will have it and and I will

it fail. We will have it and and I will underwrite that with not only my good faith but my my very body. I will be here in person to make sure that this thing succeeds. And I I had a ritual

thing succeeds. And I I had a ritual where I would write my phone number down on a business card. You call me at any hour. Don't worry about the time. I will

hour. Don't worry about the time. I will

always answer. And again 99% of the time no one would call. 1% of the time they did and then I would be on a plane. And

eventually that 1% you know they added up and to the point where I was flying a/4 million miles 300,000 mi a year and you know a lot of the times just within

the US and you know and the kind of the toll that that took on my on my health on my sleep my sanity my sense of >> you know just of equilibrium was was

actually was great. I just felt this is the only way that we can sell. I have to pledge my whole self to it and that requires me to be wherever I need to be.

And I don't I think that that was overblown. I think it was it was it was

overblown. I think it was it was it was not done out of megalomania, out of narcissism. It was done I felt out of

narcissism. It was done I felt out of necessity and I I know that I could have moderated that. I could have done better

moderated that. I could have done better and it diminished my um effectiveness ultimately. So that's probably my single

ultimately. So that's probably my single greatest regret.

>> What did you enjoy about day-to-day?

>> Um I enjoyed the sense of agency. You

know, like I one thing I always tell CEOs, your power is the power of agenda.

>> You get to decide what is being discussed, who is in the room, when is it over, what's what's in the frame of discussion, what is not in the frame of discussion. And once I understood that,

discussion. And once I understood that, it was very rewarding to me because I didn't have to be the one to make the correct answer, come to the correct decision all the time. This is who was accountable to that answer coming to the

right answer and then being definitive and saying this discussion is over or it's not over. And that's very rewarding. And I don't have that today.

rewarding. And I don't have that today.

I value that. And I I I valued being able to address the collective. I I I be to be the one that embodied the whole purpose, not not that not as the messiah, just as the spokesperson for

the thing that we are all collectively doing together. And to feel that

doing together. And to feel that appreciated, to feel a resonance from the people who work in the company sometimes for many years to say you are

giving voice to why this is a meaningful thing, why we are glad to be here. And

that was intoxicating actually.

>> See, um, now that you are an investor, >> a lot of those things no longer no longer hold.

>> But so if I were forced to like go reenter into industry, I would for sure be an investor instead of a founder >> because you're able to rescue a lot of the intellectual sort of activities that you were able and you have a lot more

control over your schedule and and >> there's less repetition. So one one part of this the CEO role is that don't underestimate how much repetition is part of your job. Yeah.

>> In fact >> like just going to the gym. Yeah. Yeah.

>> Yeah. You just have to do so many reps of just you have to repeat with almost you know with exasperating redundancy the same messages and that that is its

own purpose that everyone understands that what what you were doing because it's that hard to keep this many consciousnesses like moving in roughly the right direction together. So

investing does not have that rep repetitive. There's a lot of context

repetitive. There's a lot of context switching that's very that's very pleasurable. So like I can learn this

pleasurable. So like I can learn this domain, I can learn that domain and things that I would never have had the time to indulge and you get to meet someone who's extremely passionate and that that's that part is very rewarding.

The part that's not rewarding is that the vast majority of your interactions end up as a null. Like you have a long discussion, you do analysis, you exchange information, you build a relationship, and the answer is >> nothing,

>> right?

>> You don't do anything. Maybe you've

learned something. Maybe

>> whereas building most of it is not you're making granite, right?

>> Yeah. You're tapping away. Maybe you've

only scratched away, you know, a millimeter, but you have you have scratched away a millimeter. It's not

like we've had a lot of conversations and >> done our job today and nothing has happened. Um, and that is intrinsic to

happened. Um, and that is intrinsic to being an investor and I >> I have not fully adapted to it. It's a

little weird.

>> Um, let's go to the values of Guidewire.

They're integrity, rationality, and collegiality.

In my experience, the worst kind of company values are just kind of throwing uh nice sounding words. Yes. That that

is not only not embodied, but is hypocritically violated.

>> That's the worst.

>> The the best kind I I find is not just when the values are embodied, >> but when people clearly recognize what the trade-off of the value is, >> correct?

>> And they still take the good path. So,

for example, move fast and break things.

>> Yes.

>> We're going to value efficiency over stability. Both two good things. Yes.

stability. Both two good things. Yes.

>> But I'm telling you this relative trade-off.

>> That's right.

>> What is integrity, rationality, and collegiality? What are their trade-offs?

collegiality? What are their trade-offs?

>> Yeah, I think you put it exactly right.

Integrity is telling the truth most fundamentally. And you know, it's very

fundamentally. And you know, it's very easy to tell the truth when things are going great. So it's it's it only it's

going great. So it's it's it only it's only a value if there is a moment where it's extremely inconvenient. It's very

painful to tell the truth, right? And

what will that pain be? It will be in disappointing someone. It will making it

disappointing someone. It will making it harder to sell. It will be exposing your vulnerability or your weakness or your incompleteness or your immaturity to someone that you would prefer to convey an impression of competence of

perfection of completion etc. Right?

That is that is the trade-off. It will

be painful. Right? Um and uh or or rationality you know that what is the trade-off in trying to make the rational decision? There's a lot of trade-offs

decision? There's a lot of trade-offs actually. First of all, you have to

actually. First of all, you have to empower you are allowing people to second guessess authority because they can demand a rational explanation and you that for people in authority you

have seeded a lot of your power you instead of just saying well we will go north because I have decided north you are saying well I have a duty now to explain to you the rationale why north

and why not northeast and that's >> you have seated power and you have made you have you have imposed a new obligation on yourself >> a higher principle other than the hierarchy itself Exactly. Other than the

higher and that's a trade-off and that's it's it's timeconuming it's energy it may be exasperating right um and collegiality which expressed this idea that we are um

>> ends we are ends we are not means and the very cont the contian idea the conten idea um and what does it mean to do that well it means that uh you have

to you cannot decide hey this is the year of efficiency and you know we're going to slash a lot of people because you have to take deep accountability for the fact that you made that hiring those those incorrect decisions in the first place that you are going to make sure

that there's a kind of equality of treatment not just in the HR minimal procedural sense but in the way that everyone is addressed in the way that everyone is expected to comport and

behave with each other for example it's not acceptable to have a person take you know be very responsive to the CEO but be completely neglectful to their

subordinates so these are all expensive you know the values are expensive but if they're not expensive and they're >> vacuum. Yeah.

>> vacuum. Yeah.

>> Right. And um it's another it's it's on the short list of things I'm deeply proud of in the company that we abided by these values.

>> So the first question I want to ask you is we talked about how there's a rational way to build companies and then there's like a messianic >> um are are the rest of the two values

>> also just preferences that happen to work well for you and your team or do you think they're universal constants?

for example, collegiality. There are

companies that have done incredibly well that treat people >> completely dispensable. Yeah.

>> Completely disposable. People are

ruthless. You know, they're ruthless.

They're they're their means.

>> Um so yeah, that's the first philosophical question.

>> Yeah. And I I would say you could call it a preference, but you would say it's it's a different model. There are models of success that are emphatically not collegial, right? I mean, most

collegial, right? I mean, most classically and famously in Silicon Valley would be the Oracle culture, right? It's a place where yes, if you do

right? It's a place where yes, if you do well, you can be lavishly rewarded and if you don't, you get your face ripped off. And that and that model works,

off. And that and that model works, right? And it's insanely hierarchical.

right? And it's insanely hierarchical.

Uh it's completely transactional. Um and

that's but who could second guess its success? It has it has worked

success? It has it has worked spectacularly well over generations now, right? And it's just a model that you

right? And it's just a model that you have you can either embrace or you can reject. And and we emphatically rejected

reject. And and we emphatically rejected it, >> right?

>> Same with integrity. Now I think this is the most this is the most fraught one because when companies lie to when when a company lies externally um that's one thing that's already pernicious that's

already bad but when a company is in the habit of lying to other lying externally then it's lying to itself it knows if it gets good at lying to itself >> I see >> and when a company starts lying to it this is almost like a it's almost like a

hegelian point right but when you start getting good at lying to yourself then everything falls apart >> so these three different values they're different in nature where the latter two rationality and collegiality

seem to be preferences. Yes. Right. You

can build a nonrational messianic company. You can build a non-colgial

company. You can build a non-colgial competitive company.

>> Yes.

>> But integrity seems to be universal constant.

>> That's what I believe because when a company becomes corrupted to its core where it's it it just lies with with you know then it has the seeds of its own destruction.

>> And it's not I don't mean the moral destruction. I mean, it's not because

destruction. I mean, it's not because there's some karmic >> uh enforcer of the rights in the world.

I don't believe such a thing exists.

>> It just happens. It

>> causally causally >> because it's just a causality. You

engender a rot >> within within the body that that eventually causes it to collapse. That's

and there's different kinds of rot, but one of them is where an organization starts habitually lying to itself, right? and it just can't it can't

right? and it just can't it can't function cuz it's the the people who who start running the place become scoundrels and they and and they they stab each other in the back and they they pro they say things that about

their product that aren't true. How do

you reconcile the value of integrity with what you said about when communicating to the company? They want

to hear these things from the CEO like things are going well. I mean yeah there's not a direct tension there but you see how there's like a little bit of a >> Yeah. But but there is no tension to the

>> Yeah. But but there is no tension to the things that really matter which is what are our real prospects. Are we really doing well in a marine hot? Does our

product really work or does it not? You

know what what is our actual status?

What is our actual standing? Right?

These are the things that you have to be honest about. And it's very it's easy to

honest about. And it's very it's easy to say that you know you should just tell the simple truth. I I can tell you from my own experience the the kind of the intensity of the temptations not so much

to say that black is white uh and up is down >> but gray is white or something like that. That's right. And and to shade and

that. That's right. And and to shade and it takes a careful discernment to say how can I always convey confidence even in in the moment of greatest difficulty without ever distorting distorting the underlying truth.

>> Right. Right.

>> And and this is hard now because you have a duty to always be confident even if you don't feel it. That's the one thing that you are allowed to be dishonest about in my opinion as a CEO or the founder of a company. You must be

confident. You must say in this darkest

confident. You must say in this darkest hour we will find a way >> even if you don't believe it. Even if

you don't believe it, that is your duty.

And and the moment at which you're not willing to do that anymore is the moment you've got to resign or you've got to find a successor immediately.

>> It's a noble lie of sorts.

>> Yeah. And and that's the only one that's the only one I think you're allowed, you know, because that is because it's intrinsic to intrinsic to >> constitutive to the the role itself.

>> It's constitutive of the role itself.

That's right. And in fact, it's it's a noble lie in the same in in that sense as it comes up in philosophy as well, which is that is what people want.

people really they they they crave they require stability from their leaders.

It's a weird thing to say at this moment with with with who the body politic has elected president. But I think in

elected president. But I think in general it is certainly in every enterprise that I've seen people long for that that constancy. That's what I

meant by repetition. And so a leader who is manic is is deeply is very unsettling for followers, you know, for for the team, right? because they say, "Oh, you

team, right? because they say, "Oh, you know, John's ecstatic right now. He's

bouncing off the walls with with how exhilarated he is about how things are going, but now he's depressed." And like that's deeply disturbing. It's like it's like you don't want you to see it's like a child. You don't want to see your

a child. You don't want to see your parents, you know, exuberantly happy one moment and then distressed the next moment. That that's not encouraging.

moment. That that's not encouraging.

That's that's deeply unsettling. And I

think it's actually another duty. Maybe

it's a secondary duty to telling the truth or you know or projecting confidence but it's a secondary duty to present a kind of constancy to say just you know we may the water level may move

up or down but you know on the horizon it's level and um that was a that was a one of the developmental gifts for me in the journey was to learn at least to project that even if I didn't always

feel it >> cross-examination time I'm going to read another quote from you that seems to be again not in direct tension but philosophically seems to be in some tension.

>> But for the startup, the enemy stands in the way of all good things. They are

indolent and unworthy. They should

suffer defeat and disgrace. You want

their children to go hungry. Lest this

sound too bloodthirsty, I hasten to add, the enemy doesn't have to be a human.

The most effective slide I ever used was a picture of Guidewire's enemy, a green screen terminal. Why is it so important

screen terminal. Why is it so important to name the enemy? Because it activates the energies of your team, your tribal impulse to win as a group. Yeah.

>> The tension that I'm seeing here is >> what you just told me is that, you know, you want to calm the excitement of the group. You want to reason guides the

group. You want to reason guides the way. Yes.

way. Yes.

>> And here you want a little fan the flames a little bit. And so yeah, how do you >> But here's here's a distinction, right?

There's like what are our prospects and then who do we want to kill, right? You

can't be a peaceful insurgent. You're

trying to tear something down. There is

someone there's some zero someum aspect to what you want to do. Like we're going to succeed because others don't deserve don't deserve where they are right now.

we're going to tear some of that down.

We're going to eat their lunch. And

there's a kind of blood there's a there's a blood lust in that. There is a um there's a tribal intensity in uh of us versus them. And I think I think a

company has to harness that. That's one

of the assets that you have as a as a a big company cannot do this. I will tell you my company today is completely devoid of those feelings. It has no sense of who their enemies were. They

are tranquil, >> fad and fat and happy. Yeah, right.

>> Let's just say tranquil to a fault. And

like maybe you could say it's great. You

know, people some people should be tranquil, but that company has my company has no trace of that, you know, of of those life forces anymore. When you're a startup, you have

anymore. When you're a startup, you have to make the most of those. You have to you have to engender them. If and if you can't, then maybe you're in the wrong business because you can be you can be you can be ice cold. you be ice cold in

your own >> prosecution of an intensity >> that we are going to we're going to savage the enemy right now and that's the most lethal combination of all >> right and in fact that's trying to think

of the right character you know in popular culture >> well there's a Chinese saying here >> for the gentleman to gain his revenge even 10 years is not too long

>> right it's it's this ability to >> it's almost like the romantic thing to defer to defer the sort of satisfaction and to still have reason beh I think this is this is the corniest example but

like a like the John Wick character >> you know in the action movie so this is blood pressure pressure doesn't even rise but he is motivated by a burning hatred right he's it's it's a revenge movie a ridiculous cartoon revenge movie

but he's he's animated by uh almost genocidal rage but in his prosecution of that >> that effective >> he's he's lethal and cold right >> interesting so so that's another

interesting tension >> that the that startup and the founder needs to embody. Yes. A kind of >> Yes.

>> uncontrollable motivation that is somehow tamed by the most rational forces.

>> That's right. My Silicon Valley hero was Andy Grove. You know, he led Intel for

Andy Grove. You know, he led Intel for many many many years um before it became a lesser company. But um but Andy Grove was he was very famously like he was a

hyperrational super calm data driven guy. But he would say he he was he was

guy. But he would say he he was he was animated by a kind of genocidal intensity. He says, "We must crush every

intensity. He says, "We must crush every competitor. We have to bury them in

competitor. We have to bury them in >> Carthage must fall." Yeah.

>> Yeah. No, we must bury them, you know, in their in their crib in the crib, you know, like we have to drown every baby that that could grow up to be our enemy.

I mean, he had that kind of uh intensity at the same time that he was, you know, an engineer, hyperrational, just the facts.

>> I see. Um, you started with six more or less equal co-founders.

>> Yes.

>> In one of the early financing rounds, you sold half of the company away. Yes.

>> For what? the first

>> the first round $4 million.

>> Um, >> was your lack of ultimate ownership? You

you said by the time you IPOed, you had a very modest ownership.

>> That's right.

>> Was that ever a motivational issue?

>> It was, but again, there was no choice.

And this is this is again part of the tragedy. This is you can add this to the

tragedy. This is you can add this to the tragedy list. We had committed ourselves

tragedy list. We had committed ourselves and we had to make it succeed. And it's

very unfair. It's it was deeply deeply unfair. And you know there is no

unfair. And you know there is no platonic calculator to tell you what exactly is fair, right? Um but it clearly >> it's also obvious when it's not fair.

>> It's obvious when it's not when it's not and you know we bore all the risk and it was not right that you know just just how how that ultimate return came. Now

as it turns out the surplus was so great that it was very happy ending and it it became even greater still but nonetheless it was unfair and by today's lights you would say it was outrageous.

I mean any any found and when I describe it people can't really >> Yeah. I had to double take when

>> Yeah. I had to double take when >> you know founders can't really believe it like that like that. And you know and it puts me sometimes in a funny dilemma talking to founders you know today you know including investments that you know

that I've made you know where they say well in order for me to feel motivated you know this you know I I'm going to need more and you know and like they have you know 18 points in the company

and you said you understand like I like 2 years in to a 20-year journey you know I had a quarter of what you have right and so do you understand that it's very hard for me to relate to the your you

know to the sentiment hard, right? Because you did struggle

hard, right? Because you did struggle with with that.

>> I did struggle with it, but I walk the walk, right? And but I but you I have to

walk, right? And but I but you I have to accept that, you know, we're all it's we we measure ourselves comparatively, you know, um you know, my grandfather grew

up in a village where he was not allowed to to urinate at his school. He was he uh his his mother, my great-grandmother, compelled him to run back to his house, which was two miles two or three miles

away from the school because the nitrogen in his urine was too important for um >> the school to have it. Yeah.

>> For for the fertilizing of of the field.

>> So imagine that level of poverty, right?

And you know, I contrast that in absolute terms, you know, to the life I've gotten to lead even before my company's success.

And you know, you you need to have these kinds of correctives to right >> to a sense of blasting into infinity what you require to feel for things to feel fair.

>> So my intuition is that this was not a nagging thing for for you, right?

>> No, it it was it was but there were the the thing that was demoralizing at moments was a feeling that this journey is very very hard, you know, but we're doing it. We're succeeding. We're making

doing it. We're succeeding. We're making

progress. and then to be second-guessed by basic people who felt like interlopers. That's the time when I felt

interlopers. That's the time when I felt like alienated labor. I'm working this hard to enrich people who have no part in the creation of this value.

>> And that was a bitter feeling.

>> That was a bitter feeling.

>> Um and it was even more bitter when it was it's bad enough to work on behalf of people who are not contributing to it success. Now I'm working on who are

success. Now I'm working on who are actively impeding its success. you know,

I'm carrying, you know, a 50 kilogram load up a very steep hill and someone just came and put another 10 kilograms in. That feels that's embittering and

in. That feels that's embittering and was and those moments were very very very challenging.

>> How did you get over that?

>> There was no choice. There was no choice. Um

choice. Um >> necessity.

>> Well, there was was also looking to the future and to say there will be a day, you know, it's not today, but there will be a day when things will be on my terms. Um and um and that day came

>> right. it the the kind of romantic

>> right. it the the kind of romantic deferral again a kind of deferral.

>> It's a deferral.

>> Last question. Uh it wouldn't be a proper interview in 2025 without talking about AI to some degree.

>> You recently made a video about about AI where you were quite dismissive about its ability for deep reasoning as well as for creativity. Tell us about that.

>> Well, I'm a student here, an observer and you know um and my opinion doesn't have a lot of predictive value. All I

can say is the things that I observe directly, right? Um I don't see evidence

directly, right? Um I don't see evidence of what I would call reasoning anything like I see you know remarkable summarization uh but sometimes that summarization is

often some is incoherent or contradictory or >> it wouldn't come anywhere close to let's say the precision that comprises like a rigorous philosophical argument right

there's just you know it's at a level of kind of squishiness of kind of like vagueness that you get the gist of like what a certain person thought of what what the direction of something but that

would not comprise like a rigorous philosophical argument >> even for 01 pro and that the best model >> at least what I've seen now I have heard and I believe that these models are able to do things that are that are

incredible like with respect to solving you know math olympiad level problems and I I must credit that that that that's happening and that's a very sophisticated form of reasoning indeed but in terms of the kind of reasoning

that I understand and that was trained in I don't I don't see that ability right and >> it's the tight kind of logical structure that we just described.

>> That's right. Yeah. In like what what would be a satisfying philosophical argument, right? Like they're just kind

argument, right? Like they're just kind they're much more directional impressionist. Now, I also have some

impressionist. Now, I also have some quantitative interests and so I um took it upon myself one weekend to say let me just do the best prompt engineering I can with 01 and let's see if I can teach

it. It's a subject that I happen to know

it. It's a subject that I happen to know something about blackjack card counting and let me see how whether I can get a card counting strategy um under a certain set of conditions that I understand very well. And I spent a good

I don't know six, seven hours of like prompt engineering and trying to get it to work and I could not. That might have been my failure but it just made error mistake after mistake after mistake and places where I would say but this this is inconsistent with what you said

earlier. And the thing that was

earlier. And the thing that was disconcerting is that the whole time it was very confident. It was saying this will be better. Okay. Okay. I solved the problem that you identified. Here's a

new answer and it would be wrong.

So I'm talking to many many companies that are adding different kind of AI capabilities are things that are extremely impressive and yet so far short of what I would call real

reasoning let alone real creativity you know let alone you know ability to come up with completely novel solutions to

problems so that's just my very limited >> it's just your like anthropological report of >> yeah that's just my report of my of my observations a very interested uh and interested an engaged person. We're in a

weird moment where even some of the largest software companies in the world are saying like we could just euthanize the, you know, the engineer and AI can handle it. I find that hugely

handle it. I find that hugely implausible. I mean obviously there's

implausible. I mean obviously there's some categories of of of software development that are highly mechanical and you know that probably are within the purview of the state-of-the-art but

everything that I witnessed and I was not I did not build our products you know I uh but I was witness to their their development and involved in a lot of getting the requirements right and

obviously getting them implemented and everything that I saw in that uh it's inconceivable to me that AI could possibly build there was so much judgment so much so many

>> complexity that you had to fold in.

>> Yes. And so many nuanced decisions about like you know should we generalize here or should we not you know what should be configurable what shouldn't be where should we anticipate a need for something that could have to be extended

in the future. There was so much nuanced judgment there that it's it seems inconceivable to me that that that could be uh you know within the purview of an LLM today. Finally, I I also look at it

LLM today. Finally, I I also look at it through the optic of the lens through the lens of the company, the industry that I know best, which is insurance. I

mean, I spent 20ome years in the studying the insurance industry, serving the insurance industry and I see what AI's and in some ways AI is transformational. It's doing some

transformational. It's doing some amazing things like for example translating an enormous complex commercial policy submission and that's just written in PDFs and spreadsheets and converting it into structured form.

And that's awesome and that's incredibly impressive. But yet it still seems quite

impressive. But yet it still seems quite a distance away from doing the other kinds of deeper judgment that people in the insurance industry actually do.

>> Right. Even on a practical level like like >> even on a practical level I see a lot of it seems like there's still very substantial gaps before it can it can do thing. But that could be a completely

thing. But that could be a completely different story in >> That's really interesting. Marcus, thank

you for a fascinating interview. Yeah,

>> thank you. It's been a lot of fun.

um elaborate on uh your fascination with games because you're still a big fan of board games.

>> Yes, I love games. I would say I think that games are an art form. They're as

important an artifact in our culture as great architecture, as music, as film.

Um I think they're they're an extraordinary medium of human expression and and creativity. I I have this very simple theory about about what games comprise that they have three ingredients that a game is you have play

which you know that you you enact something that's unreal. You enter a magic circle where you say you're an orc and I'm an elf or you know I am shipwreckis and you're a Hannibal of Carthage and we're going to fight the

Punic War or the Pelpeneisian war whatever you know. So so you have an element of play but you do that under a set of rules you know it's not a free-for-all. There's there's a

free-for-all. There's there's a structure. There's something that

structure. There's something that comprises a turn. And then third, you have a sense of winning. Like what is the objective of this game? And then

when is a game over? And what what games comprises that these these three ingredients working together in a harmonious way. Play, rules, and

harmonious way. Play, rules, and winning. And if you think about other

winning. And if you think about other facets of life, you you rarely have these ingredients together. You have

sometimes you have a concept of winning under rules, like you're in a in a debate or you're trying to pass a law in Congress or win an election, right? Um,

sometimes you just have winning, but that's domination. You're just trying to

that's domination. You're just trying to dominate another person or a country is trying to dominate another. It's not

happening in a context that's both playful and structured, but also has a sense of contest. And that that's a very very beautiful allegory of like many

many facets of human life that that and games allegorize things like making decisions under uncertainty, understanding the inner subjective state of people, to negotiate with them, to persuade them, um to manage resources,

to balance short and long-term and long-term trade-offs. And so it's it's

long-term trade-offs. And so it's it's like a pallet for expressing a huge portion of the human experience, I think. And we're living in a renaissance

think. And we're living in a renaissance of games uh right now. Uh it's a very in some ways you could say our culture has become so coarse, so fragmented, so vulgar, so shallow. But I'll tell you in

the domain of games, in board games, we're living in like the peak era of the peak years of the Renaissance, right? Um

and uh yeah, it's like, you know, it's like 1565 right now, and it's it's a beautiful thing. So I love games. What

beautiful thing. So I love games. What

about the combination of the three like like why is the the existence of all three in games board games specifically what does that bring out? Is it simply like a good kaleidoscope of of human nature as a whole or like yeah what

specifically is brought out by three many many things. Um so first it's you know we are creatures of imagination right and when we we get to exercise our imagination that it it nourishes

something within us right um but in games you get to participate in that imagination in a in a kind of structured way. Um, and like the very best games

way. Um, and like the very best games can tell sometimes an allegory. I'll

give you an example. Um, there's a game designer today that I think is a genius.

His name is Cole Worley. Um, and he he he designs games of incredible intricacy and like historical sophistication. He

has this one game called John Company.

And it's about the East India Company, the British East India Company in the 17th to 19th century, right? And in this game you play members of a family of different families that have kind of

dynastic involvement and collaboration in the management of the of the East India British East India Company, right?

You have to govern the the company together. You have to generate profit

together. You have to generate profit out of it but you are so in that sense you were cooperating but you were also competing because you're not just trying to for the company to do well. you were

trying to succeed as an individual family. And the way you enact that is by

family. And the way you enact that is by buying luxury property and marrying well in um in back in England. And so all of these attributes are kind of enacted through rules. That's the thing. This

through rules. That's the thing. This

it's not it's not like a play acting.

It's not um >> it's not improv comedy or cosplay, right? It the game is very structured.

right? It the game is very structured.

There are rules. There are different phases, the things you can and cannot do, but it enacts that, right? And at

the end of this game which is is a magical experience but on the other you realize you are interior to the experience or at least one person's interpretation of the experience of what

it was to participate first in many different things. The subjugation of the

different things. The subjugation of the of the Indian subcontinent and the horrors of that but in a way that was commercially oriented in what it is to work with other people but at the same time that you were trying to compete and

beat them at the same time. the kind of the the tensions of co-opetitive dynamics that are actually a huge part of the business world and um and you are

interior to that experience to this historical moment in a way that you cannot get just from reading a book because you have actually played those roles and you have thought and inhabited and took on the motivations and the

goals and the optim the the maximizing intent that people at that moment had.

And it's only games that allow you to do this, right? um at their best.

this, right? um at their best.

>> Now it's like literature in >> it's a kind of literature that you get to embody something you wouldn't otherwise if you had access to.

>> That's right. So like if you read you know you read a great work of literature then you it it you can propel you into a moment in time and maybe you can inhabit that first person subjectivity of a certain character. Games in a way go a

certain character. Games in a way go a step further where you are actually making decisions. You are actually

making decisions. You are actually deciding as they you are not you not a witness to their decisions. You are the agent of those decisions. And in the in the best games, it leads to a kind of a

kind of revelatory uh understanding of something that before might have been behind the veil of behind the veil of history. Now,

that's only some games. There are other games that just purely exercise your mind like, you know, like like abstract games like chess or there other games that come in incredible variety. And um

>> anyway, as you can see, I could rapsidize >> indefinitely.

Thanks for watching my interview. If you

like these kinds of discussions, I think you fit in great with the ecosystem we're building at Cosmos. We fund

research, incubate, and invest in AI startups and believe that philosophy is critical to building technology. If you

want to join our ecosystem of philosopher builders, you can find roles we're hiring for, events we're hosting, and other ways to get involved on jonathanb.com/cosmos.

jonathanb.com/cosmos.

Thank you.