Andrew Kortina of Venmo and Fin on Technological Determinism and Work's Relationship to Dignity

All right, Andrew Cortina, welcome to the podcast.

Thanks for having me.

How's it going, man?

Pretty good.

Cool! So, you are the founder or co-founder of both Venmo and Fin, but you're also a blogger, yeah? I wanted to talk to you about a couple of your essays, specifically around work and human dignity. There's one called "The Beautiful Struggle," a beautiful game, and you end it with, "As we give more and more work to software machines, I think it's worth asking why we've historically regarded work as fundamental to human dignity and whether or not it's still useful to do so."

So, I found this interesting because you wrote this after selling Venmo. Mmm-hmm. And then you went and started another company. I assume like you could have taken some time off and not worked. Why do you go back to work?

Yeah, I think it's very difficult to change your own idea of dignity, and I don't necessarily even think it's something that you come up with yourself. Like I've thought a lot about this, and when I was younger I kind of thought I had an idea of like, "Okay, look, what is the good?" You know, what does it mean to like be a good person? And just either that was some like objective truth or it was like something I had like come up with myself. And I think the older I've gotten and the more fortunate I've been in life, the more I kind of recognize that a lot of things that I have are not measure things like I have accomplished myself, but things I've received from like teachers or like reading great books from the past 2,000 years of Western civilization or the culture that I grew up in, the country that I grew up in.

There's like all these things that, you know, you think you can take credit for, like a work ethic, right? Like that seems like one of the most, you know, free will determined, yeah, a strong work ethic, but you probably learned that from some role model. And I know that. So anyway, to get back to that question, I think I've sort of come to think more and more about, "Okay, like where does my own conception of dignity come from? Why does that, why would that involve like working and like making things or doing things for other people?" And I feel like I have a little bit less ownership of it.

And I guess where I was going with that is I was like, "Okay, why would a culture connect dignity with the idea of work?" And I just think it's been a useful thing to do if you live in a very uncertain world where there's things like, you know, a horde of locusts can take out the crops for the year and then there's famine, right? Like you want to incentivize people to be productive and create a surplus so you can kind of like endure those natural catastrophes. And for me, I like growing up in the United States, I think there's a lot of connection between like work and entrepreneurship and dignity and like doing service for others in your country kind of gets back to this like Protestant work ethic stuff.

And even though I think I can recognize all these sort of cultural influences on my own conception of dignity, it's really hard to, I think, convince yourself of something otherwise because, you know, it's all a ruse. And like even I know on the one hand you could say it should make it easier to like just change your mind about something. Yeah, but like if it's been inside of you for so long, it can just feel like, I don't know. I got like, I just—I don't want to go like sit around and do heroin all day. Like, oh, that would be like really fun. And I don't think there's anything wrong with that. But if it would be very tough for me to like not feel bad about that, even though I don't think it's a bad thing for somebody to do. And I think it's like just as dignified as working on, you know, an important problem. But they don't know—this stuff gets ingrained pretty deeply, and I think it's hard to change for somebody, especially once they're older.

Like maybe it can change across generations. Mmm. I think it takes time.

Well, you did describe—I forget, I think it was in that—maybe it wasn't an essay—before these kind of like flow state moments you've had outside of work. You know, you were talking about moving this like bench to the house, and I thought that was great.

That was like a serious contraption. It was so fun, yeah!

And like that's a thing. I mean, I think that's actually maybe even more of a default mode in the Bay Area where you see people like entering in this state of like vaguely working, and then they just like do projects, right? And but yet did that compel you, like maybe working with your hands and like jumping from one of those one to the next? Because I, when I'm going through these essays, I'm like, "Are these just thought experiments? Or do you just take a month or two and like actually become a Buddhist and see what happens?"

No, I've never—like there's—I have a love-hate relationship. I've never like done it myself, but it's very much like my American point of view, where it's like I had this thought once, like, you know, Buddhists are not gonna get us off this planet when the sun burns out. Like it's a very—from my sort of, you know, 50,000-foot view of it, it seems like a very like internal-focused life, struggling. How do I cope with this and like pacify my, you know, struggle with the futility of existence and all the pain and suffering that exists in life.

But I don't see a lot in that sort of philosophy that would motivate a civilization to like do large projects that help lots of people. And I think that's one of the cool things about American culture is like I do see that, and like that's kind of what I like about the idea of like dignified work is that, you know, it is a motive to inspire the people who have been a little bit more fortunate to do things that might help people that are less fortunate.

I think that's cool, but it sort of presupposes this world where that was necessary. And as that becomes less necessary and there's more abundance, then we're less a sort of resource constraint. That connection between dignity and like doing useful work maybe becomes dangerous. And like if, you know, maybe not everyone has to be productive. Maybe not everyone has the opportunity to be productive. And then are those people sort of like locked out of ever having a dignified life just because we had this useful mechanism for motivating people in the past, which is a weird situation.

I might know something I think about a lot.

So then do you not buy the argument that humans are very, very good at creating jobs? When we were talking last week, I was talking to you about people playing truck driving simulator on Twitch and then making money by having fans donate to their truck driving simulator talents. You don't think that's realistic?

I think humans are very good at creating jobs. That is—I think that's like an attention economy thing, right? Like watching other people drive trucks. And my guess is they would follow a power-law or like a vast majority of people would watch a few people doing it.

I think most things follow a power-law. And so with respect to like, I don't know, like your arguments of people make or when we get to the point where nobody has to work anymore, everyone will just do art. I'm not sure. Like, there—it depends on why you're doing art. One of the things I like about like creating things is sharing them with other people.

Mmm-hmm.

And it's pretty depressing when you're like putting like months of work into something and you put it out there and then nobody enjoys it, right? So I'm not sure that's the answer to like what will people do when they don't have to like do manual labor anymore. But I don't know. I think we're probably a long way from the point where nobody has to work anymore.

Yeah, but we should be thinking about it.

We should be thinking about it that way. That was how you ended the other essay when you said like, "What would be the last human job?" Gratitude. And yet it still resonates with you.

Yeah, I liked—I still like that one. It's always good when you look back onto the—wrote a long time ago and you still like it.

Yes, it doesn't happen that often.

Yeah, all right. So I'm curious about this—the failure mode that you're talking about in "The Beautiful Struggle." What I'll read the post, and then you can look at—you can describe it.

You might argue that we're already in a sort of failure mode where our ability to assign dignity to arbitrary work and motivate people to work [ __ ] jobs is more efficient than our ability to allocate labor towards industry that would have greater social benefit, like education, health care, food, etc. If we're already in this failure mode, it's kind of the worst of all worlds because not only are we assigning meaning to work that doesn't need to be done, but also we could be redeploying the labor towards efforts that are actually important today. Do you think we're there?

Yeah, I mean, I think about this a lot when I go to a supermarket, and I guess I know when you—I got into the habit of like going just like, you know, like a bodega in New York for a long time if I needed to space or something. And I remember I had this experience where it was the first time in years I got into like a big supermarket to get toothpaste, and there was like a whole [ __ ] aisle of toothpaste, and I just was like—and I was like vividly remember I was like reading about this and like trying to like make this into a thing I haven't done yet, but I'll probably still use it.

It was like I walked into this supermarket, and like I had made several attempts to get—I needed a toothbrush, okay? And it made several attempts to like get toothbrushes. I saw some place on Valencia Street, but I saw some people like in there, and I was like I can't see them right now. Like I mean I was like brushing my teeth with my finger face for like a couple of days. And then there was like this Saturday, I was like, "All right, I'm gonna do it. I'm going to get my toothbrush today."

And I walked into this Safeway, and Bruce Springsteen's "Everybody Has a Hungry Heart" was on the radio. And I went and I had to ask him, I was like, "Where is the toothbrush aisle?" And this is like this massive store, and I had to like navigate there, and I get to the aisle. It's just like a wall of toothbrushes, and I wanted like just a regular, you know, yeah, cheap $1.00 toothbrush.

I know I was standing there for like five minutes like trying to find a cheap, shitty toothbrush, and then I just was like, "Have a—like I'm never gonna get this five minutes back. Like this is the worst possible thing ever."

And just like look at all the garbage in front of me, right? Like and think about all like the time and like the people that thought about, you know, this toothbrush versus that toothbrush and all the effort that went into like that and marketing that stuff. And you know, somebody then went and stocked all this stuff and like made a decision that this is what should be on the shelf from this store and this is how many toothbrushes they have.

And there was just like, "Okay, this is like so wasteful."

Yeah, like they just wasted like five minutes of my time, which I'm pissed off about, but like the entire sort of line of production and marketing and distribution that went into like making that moment happen, and it was just a total waste.

And it's just like if you think about the things that you actually need to survive and the things that you value kind of at the end of the day or like when you're reflecting on things, right, it's such a small piece of commerce that's happening right now, and there's just so much garbage put out there because it's like easy to sell.

I think, yeah, well, I think there's—it’s both easy to sell, and then people like games, right? So you're entering into this company and this market where you're like, "I can do better than that guy."

Yeah.

Without stepping back and thinking, "Do we really need a toothbrush with like a thousand bristles instead of nine hundred?"

Yeah, I mean, this is kind of my thought about the singularity is that it already happened, and money is the algorithm that is already controlling all the people and telling them what to do. The machines have already taken over, I think. Literally from the beginning of money, we're gonna think.

Yeah, I thought that's so interesting. I thought it was going—coming through our phones, and because we're getting used to intermediating between these like pretty bad devices, it's going to be so easy for us to just have the full integration happen.

As soon as you’re interacting with like AI podcast guests—aí, it uses the Chinese AI newscaster. You know, it was on Hacker News the other day. It was great. I mean, it's like a completely digital newscaster, but that's an interesting thought.

Yeah, does anyone—money and dopamine? Because that's the one that you're fun access to. Is that like an internal secret Venmo slogan?

No, actually, we wanted to kind of like humanize the money and make it less about the dollars and cents—more that's why the note is like such a focal point of it. I was like, "What is the thing that you're doing? What is the moment that you're sharing with somebody else?"

Yeah, I get you. Thinking about that and not about the money, and the money is just hopefully in the background.

Mmm-hmm.

So if this world like the commercial world is overwhelming to you or just wonder whatever too much, do you practice some kind of Stoicism? You have nothing in your apartment. What does it look like?

No, I mean I have—so my girlfriend has a bed, I would have it just a mattress on the floor—but then I'll have like stuff that I use. Like I have a couple of good knives for like cutting vegetables, right? And like cutting board or like good pots and pans, but then I don't have like tons of other [ __ ] and like I'll try—if I’m not wearing clothes, I’ll try to get rid of them.

So I know on the one hand I don't have tons of stuff, but then like for the stuff that I know I'm gonna use a lot, I like it to be something good.

Mmm-hmm.

I don't really have a—I remember this, I had this professor in college, this guy John Rick Eddie, and he was—I was studying Shakespeare in London, and he was like the professor from my school that was also like abroad and like I was studying abroad; he was teaching abroad, and so he would like do stuff with us, and he had this over for Thanksgiving dinner, and he would always be taking us to plays and stuff.

And I remember one time he told me that he was just—we were like, you know, drinking a glass of wine or something, and he was like, "You know, when I die, I want them to very—um—my gravestone, 'He always lived beyond his means.'" I just—I really respect that sentiment.

So like I don't know; I don't know having tons of stuff, but I also have no problem with that kind of like extravagance in like form of expression.

Yeah, I mean if that satisfies you and can keep you going year after year.

Yeah, I don't know. I don't see it happening very often.

But yeah, I don't think it—but I know for those people, I like it that was more like the kind of like host vibe him, you know?

Yeah.

He had—it wasn't like he was necessarily buying like tons of objects; it was like spending money to like entertain or something.

Right. Well, that more falls in lines like spend money on experiences, but which is again become contentious of like these color factory type things where we've like—oh my God—bent money on artificial manufactured experience for vanity.

Yeah, I mean it's also just depressingly commercial or just like travel. I don't know. Like I was in—I went to Cambodia I think a couple of years ago.

You think you're in Cambodia?

I think it was someplace late, but that's all Asia.

Yeah, the market—you know, the street market there looked exactly like the street market in Mexico City and was just like just the entire time here. There was like you in this relationship to everyone else there as the tourist, and everything was designed to like extract money from you either in the form of like goods or experiences and like tours and stuff.

And just to this point, I’d so much rather go like explore YouTube than like be subjected to that kind of like commercial tourism machine.

Well, average input, average output, you know. I'm sure—I've never been to Cambodia, but I'm sure if you go off the beaten path you can have that experience, and you can have that experience if you just, you know, talk to someone instead of trying to buy T-shirts, right?

But it’s a very thing that it's hard to actually talk to someone there and escape that, you know, you as tourists construct.

My— the thing that's changed for me in the past I don't know five years, I've gotten really into bike touring.

Oh, that's cool.

Bike touring is cool! First of all because anyone can do it. It's not hard. Like you can just start with like 10 miles a day, stay in hotels.

But second is that it makes you interesting to everyone around the world, which I found to be super cool.

Yeah, that's really cool.

And you're the least interesting in the places where you like in basically Europe, right? Like in like the most traditional touristy places?

So really I don't really like—the first of all there's infrastructure to explore all that stuff. But it's also like I don't even need to go there.

Now instead, I can go to Vietnam and ride bikes around there.

That's cool!

At which point people—people love you.

Yeah.

So I mean I could see a world—yeah, I spent like five months in road bike touring. I didn't want to do it forever.

Yeah.

But that was that point where I was like, "Oh, I am pulled back to work."

Whether that's like a constant work for this, you know, this company or this like long-term project I have no idea, but like I want to do something.

But yeah, why do something? You know, like why is that natural or is that just because you know of all the things that you've read?

Right, like why do we want to do something?

Yeah, I don't know. It's a—I was able to scratch the itch of like physical exertion day after day.

Well, bike touring, after a while, I stopped doing, you know, a new city every night because you spend so much time thinking about logistics, which is really boring and tiring.

But even so, I think I just came to the conclusion that like the person that I wanted to be was not an adventure blogger.

Yeah.

But if that's what you want to do, it's super cool.

Yeah, but yeah, I mean I couldn't come to an answer of why do something like I guess without infinite money, and it’s like, "Okay, I need to do something."

Yeah, yeah.

Well, in the future.

Yeah.

I mean it's definitely a question mark. Do you have visions of like, you know, assuming you don't work on Fin forever your post-Fin life probably won't be a corporation?

I mean, you know what's cool about what we're working on is it's really hard and interesting, which means because of the hard problem and there's like financial incentive, you get to work with a bunch of other really smart people, which is cool.

But you know, like have any wake up to an alarm every day and like, B, there's a huge cost like coordination with a bunch of other people.

Hmm.

Like everyone has to be awake every—they all have to be awake every at the same time.

It's just like, do I want to do that? I don't know.

It goes real well, but the thing is it's not like the alarm is like kind of it—I know a big thing.

Yeah.

But it's so hard to get into like a creative mode or you can like, you know, like I forget, it takes like hours to get to the point where you can like, hmm, be like productive creatively.

And so then any sort of like routine and scheduling can just really disrupt that like if the muse is speaking, you want to be able to like write down—yeah, he's sane and be like available to that, which when you're like coordinating like huge chunks of your day around other people's time, it can be difficult.

So, but then on the other hand, like the idea of like just, you know, solo, you know, writing all the time, that seems kind of lonely.

So I don't know, it's a tough—yeah, I think it cuts both ways— but I know so many people that are like, "Oh dude, if I just like quit this job, then I can do my thing," and then they're like, "Oh, the greater job," yeah, it's hard.

It's hard—really hard.

They're like, "Do something!"

Yeah! I mean, you've got to be super disciplined either way.

Yeah, that's it.

I'm sure there's someone who's like just randomly like, "Mom, there's a movie idea!" and it immediately becomes super successful, but most people not so much, so.

So this other essay where you talk about technological determinism, "The Emperor Has No Clothes," "There Is No Santa Claus," and "Nothing Is Rocket Science," this was a lecture at Cal.

Yeah, right. And I found it really interesting because it kind of ends up dovetailing with a lot of the ideas that you talk about in the context of like, okay, maybe in a future we will not have to work.

But as it currently stands, I’m working, you're working, you're looking for jobs, whatever. This is a lecture for college kids, right? In a class where like all the other lectures are by business people about what? Like starting companies and stuff, okay?

Yeah, and I thought you started it out in like in a very honest way where you say, "I wasn't there but I just read these transcripts, right?"

Yeah, yeah.

You say, "I want to preface this talk by warning you that it's quite possible your interpret—you will interpret much of this talk as cynicism. It's not my intention to be cynical; my goal is to treat you with respect by speaking to you honestly without any grand illusions."

And then you go off, write a paragraph that jumped out to me, is you said, "None of the companies trying to convince you to work for them will mention technological determinism. They will confirm what your parents and teachers told you; that your work and contribution will be totally unique and significant."

Yeah, that's a—that's mean. That's a—it's kind of a shitty thing to hear as a college student, I think. I remember like a similar thing I heard from my college professor. Like I was having coffee with him right after I graduated. She said to me like, "I remember I was like about your age when I realized that I didn't have time in life to do all the things I wanted to do."

And I was like—I like the idea of like, you know, telling somebody something honest like that when they're younger, but the— I don't know what the kind of thing I was getting at was a lot of this was I've had a ton of fun working on hard problems with smart people.

But I think I see a lot of companies, and like I'll go visit college campuses a lot to do recruiting and kind of look at—like I'll look at other companies like engineering blogs and just like—or like I'll hear advertisements on like a podcast by some engineering company. And when I graduated from college and I went to like Penn, where, you know, Wharton is a big part of the culture there, it's like a very—it's basically a vocational school.

Hmm.

And that infects the entire rest of, you know, every other program at Penn. It's like everybody's very focused on your, like, gen ed business class you have to take. You know what I mean? But it's just the vibe of Penn. It's like—my—you and it's like, "Yeah, it's like everybody's like, you know, what internship am I getting?" Or whatever.

And when I graduated from school, I don't know, 2005, pretty much everyone that did a good job in high school, get into a good school, the next like step then they were told to do was to go get a job on Wall Street at an investment bank or at a consulting company, like a top four consulting company, huh?

And that was just like the track. And then you kind of like get married and have kids and you have a stable life. Now I think that those type of people who followed the track that was put in front of them go to get jobs here in Silicon Valley technology corporations.

But—and I think that's fine. Like, if your goal is—like if what you value is providing sustenance or like, you know, a stable home environment for like kids or for other people that depend on you, it's probably a great way to do that.

But my problem with the way that Silicon Valley does it is they've always had this like Wall Street is the bad guys, they're all about making money. Silicon Valley is about, you know, building the future and, you know, like achieving like the American Dream and like just being the doing-no-evil, and it’s really like—I don't know.

Like maybe some people get that out of it, but I have a problem with you like selling that to other people and telling them that you're gonna be their source of meaning and you're gonna enable them to like be impactful in the world.

I kind of like, like there's a certain honesty to like the Wall Street. It's like, "Come here, work hard, make a lot of money!"

Yeah, like, okay, like that's the deal!

And these technology companies don't really—I meant like that.

And I just like there's a lot of great companies do and they're building things that like are making the world better in a lot of ways, but I just think they oversell this feel-good-about-yourself thing, right? When they probably don't even have to.

Yeah, yeah, I don't know. I like on one hand I do think that technology usually is a good thing, and like many of these companies are working on great stuff, and they're also giving jobs to people that are, you know, great solid income.

Yeah, and I have no beef with someone who's like, "Hey, I'm just gonna go work at whatever X company, make this money," you know, I'm like providing for our family your parents or, yeah, or just, you know, myself, which is fine.

And then like the thing that's been kind of working me lately is like financial independence being used as this like metagame that gets like kind of thrown into the mix with young people, many of whom don't really have to earn $300,000 a year.

Like they come—maybe they come from a family, whatever it looked like, they can support them. And it just makes me sad because I'm like, "Oh, you're kind of getting played with this game."

And because you're like by default, this game is like a multi-year game that will encompass like your 20s, you might not ever do anything.

Yeah, and that makes me sad.

But yeah, you know, there's a lot of time after your 20s.

You say, "No, totally," but I just like speaking obviously, people do things over the course of their entire lives, but I look around at my friends, and like, yeah, you have kids, and it's very easy—and I don't have kids, so it's hard for me to say—but like it's very easy, it seems to make that your whole thing.

Yeah, but you, I guess, are also fine.

Yeah, I mean, that's a—and I just—I think it's a fine decision if people kind of go into it with open eyes and like fully understand it.

I feel like I just feel like there's like a little bit too much marketing of it in a certain direction that makes me uncomfortable.

Yeah, hmm. You said at a point— I mean you're quoting some of the advertisements, so you like the words were "crafted built for everyone."

Do you think—I'm just laughing.

Do the most meaningful work of your career?

Like, maybe, but the line that jumped out afterwards that I really liked is when you said, "I recognize that the meditative aspect of craft is an excellent way to cope with meaninglessness."

Yeah, which—yeah, yeah, I mean that's a—it is a—it's very meditative to it. Like one of the things that's awesome about writing software is you can just like go into this, you know stage where you're just—you spend 10 hours and you're like, "Whoa, that was so fun."

It's like playing a video game, right?

Or I mean, I think—I'm not like a great drawer, but like I've done some drawing—like when you're like just, you know, drawing that cup of water right there and like looking at all the different like shadows and contours and just focused on that, you kind of throw out all this verbal, analytical—mmm, parts of your brain.

And that is probably the type of stuff that leads you to existential despair.

It can be nice to escape that for a while, and I think like craft has that sort of, you know, like cooking is like that or, you know, writing software is like that or working with your hands, I think is like that.

They're doing Excel, I think like there's a lot of things that are like that we can can like just focus in, go into that, you know, all this—all the everything else dims, and you're just like in the zone, yeah, and it's a good escape from a lot of other things.

I think it’s also a helpful way to—well, it's an easy way to critique other people without getting to the core of the thing.

It's—it’s I used to do it, I mean, I still do it, so one of my—by saying like I'm a craftsman?

Well, I mean you could critique one who's not a craftsman.

Well, that's one that I've definitely heard. Another one is just critiquing someone else's style without getting to the core of the thing.

Yeah, another one is saying like, "Oh, you didn't do this well," and I would have done it really well without recognizing that you didn't—you didn't do it at all!

And this person is accomplishing stuff.

Yeah, and I think that is not—it's not healthy.

But then on the other hand, some people—the like all these things are dichotomies, right?

Yeah, yeah, it's just tough.

There's a lot of garbage out there, but there's a lot of people trying their best.

I don't know.

Yeah, I mean at some point in one of the essays you mentioned like it's possible that like VR would be a suitable life for people.

Maybe not for you right now, but at some point, who knows?

Yeah, I mean my VR is pretty good right now.

I like to say so.

Yeah, why is the art better than the VR?

I don't know. That seems kind of random. It's all just by the time you're conscious of it, it's all information anyway.

So theoretically, you could have a VR that’s just as good as reality.

Oh, yeah.

I mean VR plus some kind of like chemical combination, I could absolutely see them better than real life, yeah.

For—almost everyone!

Yeah, it's not a rule. I could like be a professional basketball player in VR.

I'm never gonna happen.

You can be good!

Yeah, I mean it—so if you could somehow slip into that, like really feel like you're LeBron James.

Yeah, I've never dumped a basketball in my entire life.

I’d probably be pretty sick.

It would be awesome! Like I love in a stadium with 50,000 people cheering you on.

I could be down with that; that sounds awesome!

Yeah, but again you're left with this thing is like, "Okay, like after I've consumed every level of the VR game..."

Yeah.

Maybe it's just life.

There's this good Alan Watts thing I heard where he was talking about being omnipotent and living forever. He was like, "You know, you would—an omniscient." And he was like, "Yeah, you—you know you would be cool for a while, but then you probably get bored and you start doing these simulations where you're like, okay, like I'm gonna make this game where I like limit my omnipotence in some way, and you know just it'll make it a little bit more fun."

And then you kind of get bored of that game, and you realize like, "Well, like I always know that at the after the game is over I'm omnipotent and omniscient and I went forever." And so it’s like lowers the stakes a little bit.

And so you like then you start taking away the fact that you know it’s a game.

I think he like returned to this state of the struggle of limited finite life. It was just like he kind of like got there from, "Well, of course that's what you do if you live forever," and "Why I'm not doing that right." Exactly this, it traps you.

I mean, do you ever lucid dream?

Mmm, not really.

I have the thing where I become conscious but can't move when right before you wake up, which I don't like.

Yeah, no, I wish I lucid dreamed instead.

I haven't had your experience but I've definitely lucid dream quite a bit, and my problem is exactly what you're describing. Usually what happens is something's happening, and then I predict what will happen in the dream, and then it happens, and then it just happens over and over and over again until you realize you're in complete control of the dream, and then you wake up.

Yeah, and that's—yeah, you—I rapidly ruined the entire thing.

Yes!

And you could—just so people understand, we did a podcast with Tim Urban.

Wait, but why?

Hmm, well he's cool.

Yeah, and he talks about this technological determinism as the human Colossus. It's basically the same concept.

Yeah, there's like this ball is rolling; this product will be made. You even say if Venmo—if not Venmo, something else?

Yeah, it would have happened for sure in that same space.

Yes!

How do you define technological determinism?

Yeah, I mean the way I talk about it in that talk was like a little bit—I was talking more about corollary.

Like technological determinism I think is just the society is a product of technology or something, but the kind of thing I think about a lot as a corollary of that is that kind of—I think like evolution is like this and like technology is like this, where things that are efficient and productive will eventually be created out of necessity because, you know, they make life more successful.

But if you kind of like follow that to a tent, you get into this place where it's like, "Okay, well like if everything useful will necessarily be invented by somebody out of need, like why should I work on anything?"

Right.

Like if any possible useful thing I could come up with, somebody else is gonna come up with because it's useful. So like why do it? It's not that unique or interesting.

Like so maybe I just do like all the crazy useless stuff in order to try to rescue my free will, basically.

No, the problem with that is if everybody thought that, nothing useful, right, would ever get done.

So it's kind of like presupposes that it's a, like, you know, only a few people realize that, I guess.

But I don't know, that's kind of how I think about technological determinism, is the idea like, yeah useful stuff will be built; technology is moving forward at this pace.

It's kind of like an unstoppable force.

Yeah.

And as much as like people, you know, yearn for the good old days or the, you know, Portland life of, you know, making your own cottage cheese or whatever, you're not gonna—somebody's gonna keep technology moving forward, so it's tough to ya against it.

And you use a JFK's moral argument.

Yeah, that—that JFK's speech from—he gave this talk at Rice talking about the space program, and he was talking about why—quiet! Like why are we going to space? It costs a ton of money!

Yeah.

He says some awesome stuff in there. One, he's like, "Why does Rice play Texas?"

And he was like comparing the space race to a football game, which I think is hilarious.

Like I had to step back because that was the one that I was like, "I don't know college football rankings well enough," and I was like, "Oh, it's because Texas is amazing and Rice…"

It's like, "Okay, right? That's the argument."

Well, I just think it's why do I need—is it say one college play? Another college at all? Like why does that even—like why is there a football game?

Right, because it's fun, and like competition is interesting.

Until like that's kind of like one angle of it, which is like I think really probably the better argument or like maybe the more sorry that maybe like the more truthful argument he then gives is other argument, which is, "If we don't do this space exploration thing, somebody else will."

And right now that somebody else is Russia, and we don't know their motives, and you know, space technology like all other technology has no morals of its own.

And so it's sort of like up to the good people or the more moral people who like if you're in the US, that's you presumably if you're JFK's audience.

It's up to the good people to like build the powerful technology first so that they can fight back against the bad people who also will eventually build that technology.

I think that was like just a really interesting argument. You can justify like a lot of things without argument, and like who's to say that once you build the technology what you'll use it for?

But that was a pretty compelling argument I thought.

I mean, it's the same one that OpenAI is using right now.

Yeah!

And most AI researchers.

Yeah!

So—which is, I mean, at some point we should talk about where you're currently working on.

Yeah.

Right. So yeah, so what's Fin is...?

Within AI sphere?

Yeah, weird!

So we'd like to call AAA AI—artificial artificial intelligence.

When we started the company, there was like all this—so Fin, it's a personal assistant service.

And so you can like email us, text us, tell us whatever, send this work like you would send an executive assistant.

And when we started, there was like all this excitement about like Alexa and Google Home and all these pure software AI, natural language processing things, which have very good speech-to-text and kind of natural language processing and are pretty good at understanding like most sentences that you would say to them.

But they're not really capable of being your full-time assistant.

And so our thought was, "Well, you know, these people are saying like this is gonna be, you know, like the AI from 2001: A Space Odyssey or like Jarvis from Iron Man, like it's no— we're even close to that.

But we want those things, so why don't we like try to build that today and hack it by having a system where you interact with it just like that?"

Mmm-hmm.

But instead of trying to build it with pure software—what if Google can't do? Obviously, like it's not possible.

We'll just have a team of people on the backend but do it a little bit more like Uber where it's a network of people providing the service.

They're enabled by technology—like Uber is not gonna be possible without GPS.

So there are certain like technological improvements you can take advantage of to like enable this distributed workforce to provide a new kind of service it wasn't really possible in the—and we thought it'd be cool to do that for personal assistance type stuff and just take all these sort of mundane digital chores that you don't want to do yourself but that you're probably doing right now because there's like okay tools to do them.

And because there's like okay tools to do them, not many people have assistants anymore, and so they're doing them themselves, but it's really like not an efficient use of your time.

For instance, you're some—good Julia or whatever, to be like scheduling five hours of meetings every week, right?

And like, you know, I guess like venture capitalists, they, you know, would typically have somebody scheduling their meetings, but there's a lot of other people where they don't have an assistant, and they're doing stuff like that at work or maybe they're just doing stuff at home like, you know, dealing with service providers and Comcast and like a plumber.

And if you're spending three hours doing that a week, which is like for a lot of people they probably are, and you have kids, that's like three hours that you're not spending with your kids.

And if you ask somebody like, "Which one would you rather do? Go help your kid with their homework or like play with them for three hours or be figuring out something with your health insurance?"

Like clearly, people are gonna choose spend time with their kids.

The sort of historical problem is you can't really get an assistant for three hours per week.

It's pretty tricky to figure out how.

Yeah, I mean there are people that tell you you can do that; it's pretty hard to do that to get somebody good.

You typically have to buy in chunks of 40 hours per week, or just do like tons of work to figure out like vet somebody, find people on Upwork or whatever it is like some remote VA.

And then if that person disappears, you have to do the whole thing again.

There’s just like huge amount of cost involved in like trying to piecemeal it together.

So we thought like, "Okay, like why don't we kind of like do all that work to like find good people, train them, build it so it's like a kind of like consistent, reliable experience, remember all the sort of like nuances and preferences about you, so that when turnover and nutrition does happen, you're shielded from that and like the entity like remembers your preferences around dentist appointments or whatever?"

Right? You don't want to have to tell—you know if you're hiring a new assistant every year because they're turning over, it's not really useful to have that person do your dentist thing because you only do that once a year, and you have to like retrain them on the entire thing every time.

So we've kind of taken some—a group of people that we have trained them, given them tools for collaboration, knowledge sharing, workflow management, process management, and built this system where like everything that anyone learns about you or about the world, like how to book Hamilton tickets or like how to do One Medical, write like encode that in our system, and we can actually be a lot more efficient than a single person on their own could be.

And we can give it to you in a much more incremental way.

We don't have to buy in blocks of 40 hours.

Got it!

And so there are many questions around Wolfen. So Ryan Hoover from Product Hunt asks, "When, if ever, will Wolfen task completion be 100%?"

A high-driven—yeah, I mean what if the day that happens nobody has to work anymore, right?

Because if Fin is a black box open-ended system, yeah, like we will do any work that you send us, right?

So the day that Fin can do all work, no human has to work again, and then we're all go to the beach and drink piña coladas.

And we’re at the beginning of the podcast.

Yeah, yeah, that'll be great.

So our sort of bet is while there is any human work to be done, let's build the system that is the best at doing human work.

And we'll use software to give our humans leverage and hopefully make them far more productive than somebody who's not part of our network or doesn't have access to it like our tools and knowledge base.

And, you know, for the decades to come while humans still have to work, we want to be the best place to do all that work.

Are all these people in the Bay?

Are they all—no, no.

There most of our people over at now are in Phoenix.

Okay, yeah.

What's been the hardest part and the biggest difference between starting Fin versus Venmo?

Well, Venmo though, it was always really difficult to raise money because it was a very expensive business to run and it had to be like a huge—like Venmo's just now starting to like start to monetize, yeah, with—and the method for that is to enable all these consumers to pay businesses because Venmo doesn't make money when you pay your friends back.

And so that was like a very, very long-term bet on a certain way to make money, and because we were never making any money and had to deal with all these like SEC laws and things like that, it was always like very difficult to raise money.

And we had to like use money for all these things that were not really like making the product better, so that was like a kind of thing that made Venmo hard.

I know—so it was like the first kind of like company of any size that I worked on, so first time managing people, so we had lots of challenges like that.

With Fin, on the other hand, I like have a little bit more experience managing people, so that part like is somewhat easier or, you know, at least I have like some experience and knowledge of doing it in the past, and we have a business model where both like kind of like previous entrepreneurs and have like social capital, so that made it a little bit easier to raise money.

And then the hard—the hardest thing about Fin is just complexity.

It's like the exact opposite of any of like the perfect YC company where it's like the YC company you pick one or like any, you know, like a Silicon Valley company, you pick like one small thing, you get really good at doing that thing, you get by doing tons and tons of reps on it.

And then if you get a bunch of people using that, then maybe you kind of like expand outward and like add on like another little thing and then get really good at that with Fin— we're competing with a full-time human assistant.

And a full-time human assistant will just do whatever you ask them.

It's like you hire a human assistant and he's like, "Hey, can you help me find the time to meet with Sam next week and book me flights to Phoenix?"

Yeah, and then the person says like, "Well, I don't book flights, so you're gonna have to do that yourself, but I'll schedule the meeting."

Like that—and if we'd built that, we just wouldn't be competitive with a human assistant. So we kind of took in to this—we have to be able to do anything, which is really hard.

One, it's just hard to like kind of market and like explain to people what we do because it's like—it's not like we do one thing. We just see whatever the other thing is.

It's really hard to understand.

The second thing, it’s really hard to just build tools that do anything that are like both very general and also like pretty productive and easy for people who learn.

So this—it's hard to build the tools for our team that's doing all work, and then probably one of the most challenging things is measurement.

And we spend a huge amount of time on measurement trying to understand things like, okay who’s doing a good job on our team and who's not?

Who needs help? Where do they need help? Who's good at which specific type of tasks?

Where is all the time going? Why is this thing, you know, this one type of task greater variance and a larger type of task in terms of like how long it typically takes somebody on our team to do it?

How do we categorize like different groups of customers and understand like what they would want, like what they would demand?

We have to also predict for any given week of the year for any given day of the week for any given hour of the day, how much customer demand is there going to be?

Because we're like stocking labor basically.

And if we're under supply, then people have to wait too long for work to get done. If we’re oversupply, then we're just like burning money.

Yep.

And then the other thing that's really hard too, the measurement is just hard because it's a black box system.

And so we have a heterogeneous set of people doing the work who have very different tenures, which is a lot—a big thing that like affects how well they do their work, different innate skill sets, and then a very heterogeneous set of customers and a very heterogeneous set of types of tasks that we do.

And so it can be really hard to like say we released a new thing last week, is it making the system better or worse?

To try to find an apples-to-apples trend line where you can say like, "Okay, like here is the impact of that thing," you have to slice on so many dimensions to try to get to a dataset they can tell you if any of the work that you did was actually good or bad.

So it's just really complicated.

It feels like I'm like trying to lean to do measurement in like macroeconomics or there's just like a billion different dimensions, and you're like constantly like, "Oh, well we have like a normalised for this and normalised for that."

How much is usage correlated with what you market that Fin can do?

I think today your demand for Fin is much more function of you than of our marketing.

So to get you to realize that it's more a matter of just kind of making sure you know the basics of the system.

It's helpful like talk to you about it because it's like very difficult to put in friendly and like it's really helpful like ask questions about like what your needs are.

And then basically, we just tell you like we can do all this thing.

Yeah.

But we can't like know a priori what your needs are and then like put those on the page for you, right?

So there's a certain sense we're like talking to you for a little bit helps us like realize your full potential as a customer.

But say you're the type of person that needs five hours of help per week. We're not gonna invent another like five hours of work that we can do for you.

Like, so it's a little bit different than like a media business in that sense where we could probably come up with another five hours of like TV that you would be entertained by—even if you were only currently spending five hours already.

Yeah.

But it's not like as soon as you say Fin will book flights for you, everyone uses Fin to book flights.

Well, the people that need a flight booked, but we're not gonna convince somebody that doesn't need a flight to book a flight, right?

Of course not!

So it's very much a function of like each individual customer like what they'll find.

Gosh!

So, do you ever have a moment when you talked about your Lucca's Venmo ads?

Do you ever have a moment where you're like, "I want to do this again, undo the same thing? I want to do it for fun and like get these ads everywhere?"

I don't like to do like the—you know do a read? You like that?

I mean had the Lucca's that—those were the really Subs had that we did for Venmo in New York. That was really fun to be.

I don't think we would do something like that because that was a—the market for that was a little bit different where it's like every person could use Venmo.

You know when those ads went up in New York with Fin, it's like it's not a product for every person right now.

The thing I liked about Lucca's was that it was not really—it was like in the place where you would see an ad but it wasn't actually really an ad.

It was more of like a non sequitur; it's like confusing stickers all over the stuff.

Way, yeah!

So I like the idea, and I've done this like with stuff on my website where like, you know, like my about me is like not really in about me; it's like partly fictional and like really long and like just not—it's you looking like a place where you're expecting to see one thing, and then you see something that doesn't really belong there.

But your conversion rates....

Yeah, but I like that.

And so there's something about that and thinking about, "Okay, what would that be for Fin?"

You know, could be like, you know, being showing up at some conference and like doing some crazy [ __ ] that was like not what we were supposed to be there to do.

I think that would be fun, but I'm sure would be different than like what we—what worked for Venmo!

Oh, we do for fun.

Mmm-hmm.

So Spencer Clark asked, "How did you and your co-founder decide to sell Venmo, or why?"

Well, the one, it was the options were shut down Venmo forever or sell it, so that was like a pretty easy decision.

The reasons why—I mean what's probably more interesting is to talk about like why was Braintree a good match for Venmo.

So one, obviously, like Bill Reddy who was the CEO of Braintree, only person that kind of like got it and was willing to like fund the vision of Venmo and like build up this consumer base for the sake of having a bunch of people who were wired up and comfortable using payments on their phone.

So that he was particularly I think amenable to Venmo because Braintree had—Braintree's in our company similar to Stripe where they have—they do credit card processing for all these different businesses, and the margins on credit card processing are really thin.

Mmm-hmm.

For some of Braintree, you're like Stripe, but for PayPal, they're actually awesome because PayPal was basically doing a ton of transactions that come from bank accounts and then charging a credit card processing ace instead of making like five basis points.

PayPal was making like 2% or something.

So it really like gives you many, many more multiples on your margins if you're in that payment processing business.

And so what Bill saw was like, okay, like Venmo could help Braintree go from this like very, very, very thin margin to like what's still pretty thin margins but like any standard but like still many multiples on what they had.

So that was kind of why he thought it was a good fit, and the teams kind of meshed well and they were well capitalized and had like a source of revenue and could kind of like balance out all this Venmo that was basically just dumping into user acquisition and wiring up people's bank accounts, with the hopes that one day we could somehow convince merchants to accept Rosa for Mana.

So it just made a lot of sense; one for Venmo to be part of Braintree because it was like this sort of like matching halves.

And then the same thing when PayPal acquired Braintree, I think PayPal was one of the few people that could like understand the value of Venmo because it’s like basically the same exact playbook as PayPal understand like the long-term investment it takes.

I mean, I'm sure it's probably been over like a billion dollar investment now to like wire up all these bank accounts and subsidize all the period for your transactions with the hopes of someday turning on payments to the merchant network which is now finally happening.

And my guess is will probably work out pretty well for PayPal, but like it would be very difficult, I think, for a private financier to kind of accept the billion dollar dream question.

Yeah!

So it just made sense.

Yeah, how long ago was that?

I think 2013 as well.

Yeah.

The last thing I want to talk about was that Charlie Kaufman speech, man, that's so dared everyone.

Anybody was like those things should go—you should link to that speech.

Charlie Kaufman—cool!

I'd never heard him speak before. I think that's like one of the only times he did that.

Oh, okay!

Yeah, yeah, that was great.

Did you transcribe that on your own?

Just like—no, I think I found either the YouTube transcription and cleaned up or it might have been on BAFTAs website somewhere, okay?

But I kind of pasted the transcripts on my side because I want to like add emphasis in certain areas because it's long.

I thought it might be helpful to have like some highlights in there, but yeah, I love them!

If you want like sleazoid speeches or like give people some context, but it's so—Charlie Kaufman's a screenwriter—Being John Malkovich, many other movies.

Yeah.

And that basically the set up is talking about—I mean, I can just—I can pull it out right here.

So he talks for a while, and then he goes into this moment of self-reflection on the talk to the audience about his own talk where he says, "What I'm trying to express, what I'd like to express is the notion that by being honest, thoughtful, and aware of the existence of other living beings, a change can begin to happen and how we think of ourselves in the world and ourselves in the world."

So it was awesome.

Yeah!

I mean, there's so much in there that's okay, it's really one of the best things I've come across in many years.

It's really inspiring!

He talks a lot about sort of his motives, what he's trying to do in film and just making things.

And I think he kind of—in that he gives context for a lot of stuff he's seen in his films, where he's reacting to this mechanization of human relations that kind of alienated us from each other and prevent authentic communication.

And he points to that in a lot of problems that he sees in film with people just like mechanizing and putting out more of the same [ __ ] that's just copying something else in that DNA they knew.

But I think in a lot of the work he does, you can see he sees that also in our, like daily interactions with other people or like in our relationships with even like family and friends and stuff.

It's very easy to just fall into a routine and like just saying the thing that is automatic.

And he gives this part—there's this part in that speech where he talks about he's running in his neighborhood, and he passes this guy running, and he's—and he's running down the hill on this guy who's running up a hill.

And the guy's like, "Well sure, it's all downhill that way."

And he laughs, and he's like, "Ah, that was a good."

And then he passes the guy again, same spot, and got it, same exact thing says, "Hey," he's like, "Oh, that's kind of interesting. I guess maybe like he'd forgot he said to me," and then happens in another time, same spot.

He's like, "I guess he just says that every time he sees somebody here."

He like wasn't really even paying attention to me, and then he passes him like—and he like Charlie Kaufman's going up hill and the other guy's going down hill, but he still says, "Sure, it's all down to that way."

It's like it has no context, there's like recognition or acknowledgment of like the state of the actual world; it's just this automatic thing to say.

And I think—I don't know. He points it out, and it can happen to our work and can’t happen to our relationships with other people.

And I know I found that really poignant—it was so great!

And it especially in the context of a type of work that I think most people regard as very creative.

Yeah, he's like he goes into craft in the same way that you talk about it.

He's like, "Oh, I don't think he says the name of the movie, but he's like I saw the trailer for this movie that's gonna come out is beautiful; I'm sure it's gonna be perfectly done, but it's just gonna be totally mediocre, not really accomplish anything."

Yeah!

And so, yeah, I think like first of all, thanks for posting, and I had—I had not seen it before, but also I was just curious about like how you're trying to personally apply this idea because it's obvious based on all your highlights that you cared about it a lot.

Yeah!

I really—I really feel like there's a lot of important stuff in there, but I just—I don't like the idea—this is a little bit—gifts, I think I was saying that Berkeley was there's a track that, you know, has been laid out for everybody and just like the certain way of doing things.

Like you can—it's very easy to just like do the automatic next thing without thinking about it and then wake up 50 years later and realize you haven't thought for yourself at all.

Not to say that it's necessarily bad too—I’m probably like a little bit more generous on—listen, Charlie Kaufman would be—I don't think it's just really bad to like do something that other people are doing or like that have been done before if you decide that that is like the thing that you want to spend time doing.

Or that's gonna like facilitate some other thing that you want to do.

What's tragic to me is that there's a lot of people who don't even like understand that they're in this automatic mode and just like following the next thing and like copying the thing that somebody else did or somebody doing nothing that somebody told them to do.

And the idea of like someone that like that, you know, waking up 50 years later at me like, "Well, I didn't want to do any of that," or just never realizing having that thought at all, I was just sad.

So I try to spend a lot of time thinking about like, "Okay, like how do I be intentional? Like am I doing the thing that I want to do? Is it gonna be like different in some way and something up?"

Because I do like the idea of trying to do something differently than the way other people would do it.

So I think about that a lot, but it's kind of a radical, and like you can—you can spend a lot of time thinking about that and realize that it's pretty hard to do and maybe not possible.

Yeah!

And you can fall into a new kind of trap, which is competitive mindfulness.

Yes!

I find so funny.

Yes!

So I can meditate longer than you can!

Yeah!

All right, dude! So if someone wants to talk to you online or try out Fin, what should they do?

So try out Fin; we have a code for E, and somebody asks like when—if ever, will Fin be free?

'Cause it could be free, but you get $100 credit if you sign up at Fin.com/yc, so you could just try that out there.

And then if you want to find me online Cortina with a K on Twitter or Kourt em I see is where I post on my reading.

Awesome! Thanks, man!

Thank you!