- Andrew Cortina, co-founder of Venmo and Finn, discusses the concept of work and human dignity in his essays.
- He reflects on his own ideas of dignity and how they have been influenced by external factors such as teachers, books, and cultural upbringing.
- Cortina explores the connection between work and dignity, and how it has been historically useful in incentivizing productivity and creating surplus in uncertain times.
- He also discusses the difficulty of changing one's conception of dignity, especially as one gets older.
- Cortina shares his love-hate relationship with Buddhism and its focus on internal struggles, contrasting it with the motivation for large projects that help others in American culture.
- He questions the connection between dignity and work in a world of abundance, where not everyone may have the opportunity to be productive.
- Cortina expresses skepticism about the future where nobody has to work anymore, and discusses the power law dynamics in the attention economy.
- He emphasizes the need to think about the future of work and the allocation of labor towards industries with greater social benefit.

- The author argues that our society assigns meaning and value to work that is unnecessary, while neglecting important industries like education and healthcare.
- The author reflects on a frustrating experience at a supermarket, where the abundance of choices and wastefulness of consumer goods made them question the efficiency of our commercial world.
- The conversation touches on the idea that money and technology have already taken control over our lives, and the role of dopamine in our interactions with money.
- The author discusses their minimalist lifestyle and preference for experiences over material possessions.
- The conversation concludes with a discussion on the commercialization of tourism and the author's interest in bike touring as a way to have more genuine interactions with people around the world.

- The speaker finds traditional touristy places in Europe uninteresting and prefers exploring places like Vietnam.
- They have a desire to do something meaningful and are unsure if it is natural or influenced by what they have read.
- The speaker enjoys bike touring but realizes they do not want to be an adventure blogger.
- They question the need for routine and coordination with others in a traditional job.
- They discuss the challenges of balancing creativity and routine in their work.
- The speaker highlights the unrealistic expectations set by companies in Silicon Valley and the overselling of the feel-good aspect of working for them.
- They believe that technology can be a positive force but question the messaging and motivations of technology companies.

The speaker believes that technology can be beneficial and provide jobs, but is concerned about the emphasis on financial independence and the marketing of certain careers. They discuss the meditative aspect of craft and how it can be an escape from existential despair. They also touch on the tendency to critique others and the potential of VR to provide a better life experience. The concept of technological determinism is mentioned, suggesting that useful inventions will inevitably be created, leading to a discussion on the value of pursuing unique and useless endeavors.

- The speaker discusses the concept of technological determinism and the inevitability of technological progress.
- They mention JFK's speech about the space program and the argument that if the US doesn't advance in technology, someone else will (like Russia).
- The speaker then talks about their company, Fin, which is an artificial, artificial intelligence (AAI) personal assistant service.
- They explain that their goal is to provide a service that can handle mundane digital tasks and free up people's time.
- The speaker mentions the challenges of finding part-time assistants and explains how Fin solves this problem by utilizing a network of trained individuals.
- They state that Fin's ultimate goal is to be the best place to do human work until the day when AI can fully replace human work.
- Most of the company's team is located in Phoenix.
- The speaker compares starting Fin to starting Venmo and highlights the difficulties they faced in raising money for Venmo due to its long-term monetization strategy.

- The founder discusses the challenges faced by Venmo, including difficulty raising money and managing people.
- Finn, the founder's current company, has a more experienced team and a clear business model, making it easier to raise funds.
- Finn's main challenge is its complexity, as it aims to compete with a human assistant and must be able to do anything.
- Measurement is a significant challenge for Finn, as it involves understanding team performance, customer demand, and the impact of new features.
- Finn's marketing strategy focuses on understanding individual customer needs and communicating the system's capabilities.
- The founder reflects on the success of Venmo's Lucas ads and discusses the potential for unconventional marketing strategies for Finn.
- The decision to sell Venmo was driven by the options of shutting it down or finding a suitable buyer.
- The founder explains that Braintree was a good match for Venmo due to their shared vision and the potential for increased margins through PayPal's payment processing business.

- The acquisition of Venmo by Braintree was seen as a good fit due to their complementary strengths and potential for increased margins.
- PayPal's acquisition of Braintree was also seen as a good fit due to their understanding of the value of Venmo and their long-term investment strategy.
- The speaker recommends watching a speech by Charlie Kaufman, a screenwriter, that discusses the importance of being honest, thoughtful, and aware of others in order to bring about change in how we think of ourselves and the world.
- The speaker reflects on the mechanization of human relations and the lack of authentic communication in daily interactions and relationships.
- The speaker emphasizes the importance of being intentional and doing things differently than others, but acknowledges the challenges and potential traps of trying to do so.
- The speaker promotes the use of Finn and offers a $100 credit for signing up, and provides contact information for further communication.

- Andrew Cortina, co-founder of Venmo and Finn, explores the concept of work and human dignity in his essays.
- He discusses the historical connection between work and dignity, as well as the difficulty of changing one's conception of dignity.
- Cortina shares his love-hate relationship with Buddhism and questions the connection between dignity and work in a world of abundance.
- He emphasizes the need to think about the future of work and the allocation of labor towards industries with greater social benefit.
- The author reflects on the inefficiencies of our commercial world and the role of money and technology in our lives.
- The conversation also touches on the commercialization of tourism and the speaker's interest in bike touring.
- The speaker discusses their preference for experiences over material possessions and their desire to do something meaningful.
- They question the need for routine and coordination in a traditional job and highlight the challenges of balancing creativity and routine.
- The speaker critiques the messaging and motivations of technology companies, while acknowledging the potential benefits of technology.
- They discuss their company, Fin, which aims to provide a personal assistant service to handle mundane digital tasks.
- The founder reflects on the challenges faced by Venmo and the acquisition of Venmo by Braintree.
- They recommend watching a speech by Charlie Kaufman and emphasize the importance of being intentional and doing things differently.

Andrew Kortina - https://twitter.com/kortina - is the cofounder of Venmo and Fin. Fin is a high quality, on-demand, personal assistant and executive assistant service. 

You can get a $100 credit to try Fin at https://fin.com/yc

Andrew blogs at https://kortina.nyc/

The YC podcast is hosted by Craig Cannon - https://twitter.com/craigcannon

***

Topics 

00:00 - Human dignity and work

7:35 - Creating jobs

9:35 - From The Beautiful Struggle // The Beautiful Game - 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 bullshit jobs is more efficient than our ability to allocate labor towards industry that would have greater social benefit, like education, healthcare, 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 that labor towards efforts that are actually important today. 

https://kortina.nyc/essays/the-beautiful-struggle-the-beautiful-game/

18:00 - Travel

20:30 - Why do we want to do anything?

21:35 - Life after Fin

24:45 - From The Emperor Has No Clothes, There is No Santa Claus, and Nothing is Rocket Science - I want to preface this talk by warning you that it’s quite possible you’ll interpret much of this talk as cynicism. It is not my intention to be cynical. My goal is to treat you with respect by speaking to you honestly, without any grand illusions.

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.

https://kortina.nyc/essays/the-emperor-has-no-clothes-there-is-no-santa-claus-and-nothing-is-rocket-science/

31:30 - From The Emperor Has No Clothes, There is No Santa Claus, and Nothing is Rocket Science - I recognize that the meditative aspect of craft is an excellent way to cope with meaninglessness

38:00 - Technological determinism

42:30 - Andrew's company Fin

47:45 - Ryan Hoover asks - When (if ever) will Fin task completion be 100% AI-driven?

49:00 - Differences between running Fin and Venmo

56:15 - Venmo's Lucas ads

58:00 - Spencer Clark asks - How did you and your co-founders decide to sell Venmo?

1:01:30 - Charlie Kaufman on Screenwriting - 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 in how we think of ourselves and the world, and ourselves in the world.

https://kortina.nyc/essays/charlie-kaufman-bafta-speech/

1:08:30 - Get $100 credit to Fin at https://fin.com/yc

All right, Andrew Cortina, welcome to the podcast.

So you are the founder or co-founder of both Venmo and Finn, but you're also a blogger.

And I wanted to talk to you about a couple of your essays, specifically around work, human dignity.

There's 1 called The Beautiful Struggle, The 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.

And then you went and started another company.

I assume you could have taken some time off and not worked.

Yeah, I think it's, 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, 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 necessarily things like I have accomplished myself, but things I've received from like teachers or like reading great books from the past 2000 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 1 of the most, you know, free will determined things, like a strong work ethic, but you probably learn that from some role model.

And I don't know, 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 would that involve working and making things or doing things for other people?

And I feel like a little bit less ownership of it.

And I guess where I was going with that essay 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?

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, growing up in the United States, I think there's a lot of connection between like work and entrepreneurship and dignity and kind of 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 like all these sort of like 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 don't know on the 1 hand you could say it should make it easier to like just change your mind about something Yeah, but like if it's if it's been inside of you for so long it can just feel like I Don't know like I'm like I just I don't want to go like sit around and do heroin all day.

Like I'm sure that would be like really fun and I don't think there's anything wrong with that but 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.

I think it's just as dignified as working on an important problem.

But I don't know, this stuff gets ingrained pretty deeply.

I think it's hard to change for somebody, especially once they're older.

Like maybe it can change across generations,

Well you did describe, I forget, I think it was in that, maybe it was in the essay before, these kind of like flow state moments you've had outside of work.

You were talking about moving this like bench to

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?

Like maybe working with your hands and like jumping from 1 of those 1 to the next?

Because when I'm going through these essays, I'm like, are these just thought experiments or do you just take a month or 2 and like actually become a Buddhist and see what happens to you?

No, I've never like, there's, I have a love-hate relationship with Buddhism.

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 going to 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 is 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 1 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.

But it sort of presupposes this world where that was necessary, and as that becomes less necessary and there's more abundance and we're less sort of resource constrained, 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 have this useful mechanism for motivating people in the past?

And like, I don't know, something I think about a lot.

So then do you do you not buy the argument that humans are very, very good at creating jobs?

When we 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 where like a vast majority of people would watch a few people doing it.

And so, with respect to like, I don't know, like a lot of the arguments that people make are when we get to the point where nobody has to work anymore, everyone will just do art.

Like, it depends on why you're doing art.

1 of the things I like about like creating things is sharing them with other people.

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.

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.

I think we're probably a long way from the point where nobody has to work anymore.

Harness, Ph.D.: We should be thinking about it.

That was how you ended the other essay when you said like, What will be the last human job gratitude and

Yeah, I'd like I saw that on the on the materials.

I was like, oh, yeah, I still like that 1 It's always good when you look back on something you wrote a long time ago and You still like it?

So I'm, I'm, I'm curious about this, this failure mode that you're talking about in the beautiful struggle.

What I'll read the post and then you can, 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 bullshit 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.

Yeah, I mean, I think about this a lot when I go to a supermarket.

And I guess, I don't know, when you, I got into the habit of like, going to just like, you know, like a bodega in New York for a long time, if I needed toothpaste or something.

And I remember I had this experience where, It was the first time in years I had gone to like a big supermarket to get toothpaste.

And there was like a whole fucking aisle of toothpaste.

And I just was like, and I was like vividly remember that I was like writing about this and like trying to like make this into a thing.

And I haven't done yet, but I'll probably still use it.

It was like I walked into this supermarket and I had made several attempts to get, oh I needed a toothbrush.

And I made several attempts to get toothbrushes where I saw some place on Valencia Street but I saw some people like in there, I was like, I can't be near them right now.

And I was like brushing my teeth with my finger and toothpaste for like a couple of days.

And then it was like this Saturday, I was like, all right, I'm going to do it.

And I walked into this Safeway and Bruce Springsteen's Everybody Has a Hungry Heart was on the radio.

And I went and I asked somebody like, where is the toothbrush aisle?

And there's like this massive store and I had to like navigate there.

And I get to the aisle and it's just like a wall of toothbrushes and I wanted like just a regular, you know, cheap $1 toothbrush.

And I was standing there for like 5 minutes like trying to find a cheap shitty toothbrush.

And then I just was like, how have I like, I'm never gonna get this 5 minutes back.

Like this is the worst possible thing ever and just like look at all the garbage in front of me.

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 made a decision that this is what should be on the shelf in the store and this is how many toothbrushes they have.

And I was just like, oh my God, this is so wasteful.

It just wasted 5 minutes of my time, which I'm pissed off about.

But the entire line of production and marketing and distribution that went into making that moment happen, 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 at the end of the day or when you're reflecting on things.

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.

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, oh I can do better than that guy.

Without stepping back and thinking, do we really need this toothbrush with like a thousand bristles instead of 900?

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.

Or do you think when money was digitized?

Money is the API for people, and that's when we see the control to the machines.

I thought It was coming through our phones, and because we're getting used to intermediating between these 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 AI podcast guests, AI, Did you see the Chinese AI newscaster?

I mean it's like completely digital newscaster.

Because that's the 1 that your phone has access to.

Is that like an internal secret Venmo slogan?

Actually We wanted to kind of like humanize the money and make it less about the dollars and sends it more.

That's why the note is like such a focal point of MMOs.

Like what is the thing that you're doing?

What is the moment that you're sharing with somebody else?

And get you thinking about that and not about the money.

And the money is just hopefully in the background.

So if this world, like the commercial world, is overwhelming to you, or just whatever, too much, Do you practice some kind of stoicism?

No, I mean, I have, so my girlfriend has a bed.

I would have just a mattress on the floor.

But then I'll have like, 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 shit.

And like, I'll try to, like, if I'm not wearing clothes, I'll try to get rid of them.

And on the 1 hand, I don't have tons of stuff, but then like for the stuff that I know I'm gonna use a lot, I'd like it to be something good.

I remember this, I had this professor in college, this guy John Ricchetti, and he would, 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 1 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, when I die, I want them to write on my gravestone.

And I was like, that's just, I just, I really respect that sentiment.

I don't love having tons of stuff, but I also have no problem with that kind of like extravagance and like form of expression.

Yeah, I mean, if that satisfies you and can keep you going year after year, I don't know.

Friedman Yeah, I don't think it, but I know for those people, that was more like the kind of like host vibe, you know, I think that he had.

It wasn't like he was necessarily buying like tons of objects.

It was like spending money to like entertain or something.

Well, that more falls in line with like spend money on experiences.

But which has again become contentious of like these color factory type things where people like, oh my God, spend money on artificial manufactured experience for vanity.

I mean, that's also just depressingly commercial or just like travel.

Like I was in, I went to Cambodia, I think a couple of years ago.

It was like the market, you know, the street market there looked exactly like the street market in Mexico City.

And it was just like this the entire time you're there was like you in this relationship to everyone else there as the tourist and everything was designed to extract money from you either in the form of goods or experiences and tours and stuff.

I'm just at this point now where I'd so much rather go explore YouTube than be subjected to that kind of like commercial tourism machine.

You know, you can, 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 very, the thing, it's hard to actually talk to someone there and escape that, you know, you as tourist construct.

My, the thing that's changed for me in the past, I don't know, 5 years is I've gotten really into bike touring.

Bike touring's cool, First of all, because anyone can do it.

Like you can just start with like 10 miles a day, stay in hotels.

But second is that it makes you interesting everyone around the world, which I found to be super 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 you're like, I don't really like the first of all, there's infrastructure to explore all that stuff.

But it's also like, oh, I don't even need to go there now.

Instead I can go to Vietnam and ride bikes around there.

I spent like 5 months in a row bike touring.

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

Whether that's constant work for this company or this long-term project, I have no idea.

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.

physical exertion day after day while 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 the person that I wanted to be was not an adventure blogger.

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

But yeah, I mean I couldn't come to an answer of why do something like I guess without infinite money I was like, okay I need to do something.

Yeah, I mean that's a good, but for now, but maybe it won't be in the future.

Yeah, 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?

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

But having to wake up to an alarm every day, there's a huge cost to coordination with a bunch of other people.

Like everybody has to be awake at roughly the same time.

Well, But the thing is, it's not like the alarm is like kind of a tiny cheek thing.

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

And so then any sort of routine and scheduling can just really disrupt that.

Like if the muse is speaking, you want to be able to like write down what the muse is saying 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.

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.

Yeah, I think it cuts both ways, but I know so many people that are like, oh dude, if I just quit this job, then I can do my thing.

And then they quit their job and they don't.

Yeah, and it's really hard to do something.

Yeah, I mean, you gotta be super disciplined either way.

I'm sure there's someone who's just randomly like, well, there's a movie idea, and it immediately becomes super successful.

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.

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 to undergrad college kids, right?

In a class where all the other lectures are by business people.

And I thought you started it out in like in a very honest way where you said I wasn't there but I just read the these this like transcript right

you say I want to preface this talk by warning you that it's quite possible you will interpret much of this talk as cynicism.

My goal is to treat you with respect by speaking to you honestly without any grand illusions." And then you go off, right?

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, I 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 a college professor, like I was having coffee with 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 just 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, the, the kind of thing I was getting at with 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 campus a lot to do recruiting and

of look at like, I'll look at other companies like engineering blogs or I'll hear advertisements on a podcast by some engineering company.

And When I graduated from college, and I went to Penn where Wharton is a big part of the culture there, and so it's basically a vocational school.

And that infects the entire rest of, every other program at Penn.

Paul A You have like Gen Ed business class you have to take?

Brian No, I mean, but it's just the vibe of Penn.

I went to NYU and it's like, can't be like that.

Brian Yeah, so everybody's like, 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 got into a good school.

The next step that 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 4 consulting company.

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 follow the track that was put in front of them go to get jobs here in Silicon Valley at technology corporations.

See all Y Combinator transcripts on Youtube

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