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

by Y Combinator11/20/2018

Andrew Kortina is the cofounder of Venmo and Fin.

Andrew blogs at and is on Twitter @kortina.


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.

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.

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?

1:01:30Charlie 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.

1:08:30 – Get $100 credit to Fin at


Google Play


Craig Cannon [00:00:00] – Hey, how’s it going? This is Craig Cannon, and you’re listening to Y Combinator’s podcast. Today’s episode is with Andrew Kortina. Andrew’s the co-founder of Venmo and Fin. Fin is a high-quality on-demand personal assistant and executive assistant service. You can get $100 credit to try Fin at I’ll also link that up in the show notes. If you want to find Andrew on Twitter, he’s @kortina, and he’s blogging at All right, here we go. All right, Andrew Kortina, welcome to the podcast.

Andrew Kortina [00:00:34] – Thanks for having me.

Craig Cannon [00:00:35] – How’s it going, man?

Andrew Kortina [00:00:35] – Pretty good.

Craig Cannon [00:00:36] – You are the founder or co-founder of both Venmo and Fin, but you’re also a blogger. I wanted to talk to you about a couple of your essays.

Andrew Kortina [00:00:47] – Cool.

Craig Cannon [00:00:48] – Specifically around work, human dignity. There is one 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. I found this interesting because you wrote this after selling Venmo. Then you went and started another company. I assume you could have taken some time off and not worked. Why did you go back to work?

Andrew Kortina [00:01:25] – I think it’s very difficult to change your own idea of dignity. I don’t necessarily even think it’s something that you come up with yourself. I’ve thought a lot about this. When I was younger I kind of thought I had an idea of, “Okay, what is the good, you know, what does it mean to be a good person?” Either that was some objective truth or it was something I had come up with myself. 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 I have accomplished myself, but things I’ve received from teachers or 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 all these things that you think you can take credit for, like a work ethic, right, that seems like one of the most free-will-determined things, a strong work ethic, but you probably learned that from some role model. 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, where does my own conception of dignity come from?” Why does that, why would that involve working and making things or doing things for other people? I feel a little bit less ownership of it. And I guess where I was going with that essay was, “Okay, why would a culture connect dignity with the idea of work?” I just think it’s been a useful thing to do. If you live in a very uncertain world

Andrew Kortina [00:03:31] – where there’s things like 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 endure those natural catastrophes. For me, growing up in the United States, there’s a lot of connection between work and entrepreneurship and dignity and doing service for others and your country, kind of gets back to this Protestant work ethic stuff. 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. On the one hand you could say it should make it easier to just change your mind about something, but if it’s been inside of you for so long it can just feel like, I don’t know, I just, I don’t want to go like sit around and do heroin all day. 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 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 just as dignified as working on an important problem. This stuff gets ingrained pretty deeply, and I think it’s hard to change for somebody, especially once they’re older. Maybe it can change across generations, but I think it takes time.

Craig Cannon [00:05:12] – 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 bench to the roof of a house. I thought that was great, by the way. That was a serious contraption you guys made.

Andrew Kortina [00:05:29] – That was so fun, yeah.

Craig Cannon [00:05:31] – 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 vaguely working, and then they just do projects, right. But yet did that compel you, like maybe working with your hands and jumping from one of those, one to the next? 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 actually become a Buddhist and see what happens to you?

Andrew Kortina [00:06:05] – I have a love-hate relationship with Buddhism. I’ve never done it myself. But it’s very much like my American point of view where it’s like, I had this thought once, you know, Buddhists are not going to get us off this planet when the sun burns out. It’s a very, from my sort of 50,000-foot view of it, it seems like a very internal focused, life is struggling, how do I cope with this and pacify my 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 do large projects that help lots of people. That’s one of the cool things about American culture, is I do see that. That’s kind of what I like about the idea of dignified work, is that 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. 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 doing useful work maybe becomes dangerous. Maybe not everyone has to be productive, maybe not everyone has the opportunity to be productive, and then are those people sort of 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 and something I think about a lot.

Craig Cannon [00:08:07] – 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 making money by having fans donate to their Truck Driving Simulator talents. You don’t think that’s realistic for the future?

Andrew Kortina [00:08:33] – I think humans are very good at creating jobs. That is, I think that’s an attention economy thing, right, like watching other people drive trucks. My guess is they would follow a power law where a vast majority of people would watch a few people doing it. I think most things follow a power law. 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. I’m not sure. It depends on why you’re doing art. One of the things I like about creating things is sharing them with other people, and it’s pretty depressing when you’re putting months of work into something and you put it out there and then nobody enjoys it. I’m not sure that’s the answer to what will people do when they don’t have to 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. But we should be thinking about it.

Craig Cannon [00:09:43] – 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.”

Andrew Kortina [00:09:50] – That’s it, yeah.

Craig Cannon [00:09:51] – It still resonates with you.

Andrew Kortina [00:09:52] – Yeah, I saw that on the prep material, I was like, oh, that, yeah, I still like that one. It’s always good when you look back on something you wrote a long time ago and you still like it because it doesn’t happen that often.

Craig Cannon [00:10:05] – All right, so I’m curious about this failure mode that you’re talking about in The Beautiful Struggle. 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, healthcare, food, et cetera. 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?

Andrew Kortina [00:10:50] – Yeah. I think about this a lot when I go to a supermarket. I got into the habit of going to just like, you know, like a bodega in New York for a long time if I needed toothpaste or something. I remember I had this experience where it was the first time in years I had gone to a big supermarket to get toothpaste, and there was a whole fucking aisle of toothpaste. I vividly remember that I was writing about this and trying to make this into a thing, and I haven’t done it 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. I’d made several attempts to get toothbrushes where I saw some place on Valencia Street but then I saw some people in there, I was like, “I can’t be near them right now.” Then I was brushing my teeth with my finger and toothpaste for a couple of days. Then there was this Saturday, I was like, all right, I’m going to do it, I’m going to get my toothbrush today. I walked into this Safeway, and Bruce Springsteen’s “Everybody Has A Hungry Heart” was on the radio. I went and I asked somebody,

Andrew Kortina [00:12:12] – “Where is the toothbrush aisle?” It’s just this massive store, and I had to navigate there and I get to the aisle and it’s just a wall of toothbrushes. I wanted just a regular, you know, cheap $1 toothbrush. I was standing there for like five minutes trying to find a cheap shitty toothbrush, and then I just was like, how have I, I’m never going to get this five minutes back. This was the worst possible thing ever, and just look at all the garbage in front of me. Think about all the time and the people that thought about this toothbrush versus that toothbrush, and all the effort that went into that and marketing that stuff and 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. I was just like, “Oh my god, this is so wasteful.” They’ve just wasted five minutes of my time, which I’m pissed off about, but the entire sort of line of production and marketing and distribution that went into making that moment happen, then just a total waste. 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 easy to sell, I think.

Craig Cannon [00:13:53] – Yeah, well, I think there’s, it’s both easy to sell and then people like games, right. You’re entering into this company and this market where you’re like, “Ah, I can do better than that guy,” without stepping back and thinking, do we really need this toothbrush with like 1,000 bristles instead of 900?

Andrew Kortina [00:14:13] – 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.

Craig Cannon [00:14:31] – Literally from the beginning of money, when you think when money…

Andrew Kortina [00:14:36] – Yeah, money is the API

Craig Cannon [00:14:36] – was digitized.

Andrew Kortina [00:14:37] – for people. That’s when we cede the control to the machines.

Craig Cannon [00:14:41] – Dang, yeah, I thought, that’s so interesting. 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 like AI podcast guest, AI, did you see the Chinese AI newscaster?

Andrew Kortina [00:15:05] – No.

Craig Cannon [00:15:05] – It was on Hacker News the other day.

Andrew Kortina [00:15:06] – Oh, cool.

Craig Cannon [00:15:07] – It was great, I mean, it’s like completely digital newscaster.

Andrew Kortina [00:15:08] – Oh.

Craig Cannon [00:15:11] – But that’s an interesting thought.

Andrew Kortina [00:15:13] – Yeah, just dopamine and anyone. Money and dopamine, because that’s the one that your phone has access to.

Craig Cannon [00:15:19] – Yeah. Is that like an internal secret Venmo slogan?

Andrew Kortina [00:15:23] – Money and dopamine?

Craig Cannon [00:15:24] – No. Money is the API for humans.

Andrew Kortina [00:15:27] – Oh, no, no, that wasn’t, no. Actually, we wanted to kind of humanize the money, and make it less about the dollars and cents and more, that’s why the note is like sort of the focal point of Venmo. It’s like, what is the thing that you’re doing? What is the moment that you’re sharing with somebody else? Het you thinking about that and not about the money, and the money’s just hopefully in the background.

Craig Cannon [00:15:53] – If this world, the commercial world, is overwhelming to you, or just whatever, too much, do you practice some kind of stoicism? You have nothing in your apartment? What does it look like?

Andrew Kortina [00:16:10] – No. My girlfriend has a bed. I would have just a mattress on the floor. But then I’ll have stuff that I use. I have a couple of good knives for cutting vegetables, right, and a cutting board, or good pots and pans. But then I don’t have tons of other shit. I’ll try to, if I’m not wearing clothes I’ll try to get rid of them. I don’t know, on the one hand I don’t have tons of stuff, but then for the stuff that I know I’m going to use a lot I like it to be something good. But I don’t really have, I don’t know. I remember I had this professor in college, this guy John Racette, and I was studying Shakespeare in London and he was, the professor from my school that was also abroad and I was studying abroad, he was teaching abroad, and so he would do stuff with us. He had this little bit oF a 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 drinking a glass of wine or something, and he was like, “You know, when I die I want them to write on my gravestone, ‘He always lived beyond his means.'” I really respect that sentiment. I don’t love having tons of stuff, but I also have no problem with that kind of extravagance and that form of expression.

Craig Cannon [00:17:48] – Yeah, I mean, if that satisfies you and can keep you going year after year. I don’t know, I don’t see it happen very often, but– It sounds sad.

Andrew Kortina [00:17:59] – Some of those people, that was more the kind of host vibe, you know, I think, that he had. It wasn’t like he was necessarily buying tons of objects. It was spending money to entertain or something.

Craig Cannon [00:18:14] – Right, well that more falls in line with spend money on experiences. But which has again become contentious. These Color Factory type things where we’re like, oh my– Spend money on artificial manufactured experience for vanity.

Andrew Kortina [00:18:32] – It’s also just depressingly commercial. Or just like travel, I don’t know. I was in, I went to Cambodia, I think, a couple of years ago.

Craig Cannon [00:18:48] – You think you were in Cambodia?

Andrew Kortina [00:18:50] – I think it was, it was some place like that. But the point is–

Craig Cannon [00:18:52] – Southeast Asia.

Andrew Kortina [00:18:53] – The market, you know, the street market there looked exactly like the street market in Mexico City, and it was just like the entire time we were there it 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. Just to this point, I would so much rather go explore YouTube than be subjected to that kind of commercial tourism machine.

Craig Cannon [00:19:25] – Well, average input, average output. 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. You can have that experience if you just talk to someone instead of trying buy T-shirts, right.

Andrew Kortina [00:19:41] – Yeah, but the thing, it’s hard to actually talk to someone there and escape that, you know, you as tourist construct.

Craig Cannon [00:19:53] – The thing that’s changed for me in the past, I don’t know, five years, is I’ve got really into bike touring.

Andrew Kortina [00:20:00] – Oh, that’s cool.

Craig Cannon [00:20:01] – Bike touring’s cool, first of all, because anyone can do it, it’s not hard. You can just start with 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.

Andrew Kortina [00:20:16] – Yeah, that’s really cool.

Craig Cannon [00:20:18] – You’re the least interesting in the places where you’re like, in basically Europe, right, in like the most traditional touristy places. 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 round there.

Andrew Kortina [00:20:36] – That’s cool.

Craig Cannon [00:20:37] – At which point people love you.

Andrew Kortina [00:20:39] – Yeah, I like that, I love biking, it’s really fun.

Craig Cannon [00:20:43] – I spent five months on the road bike touring. I didn’t want to do it forever, but that was a point where I was like, “Oh, I am pulled back to work,” whether that’s like constant work for this, you know, this company or this long-term project, I have no idea, but I want to do something–

Andrew Kortina [00:21:04] – But yeah, why do something? Why, is that natural or is that just because of all the things that you’ve read, right? Why do we want to do something?

Craig Cannon [00:21:16] – I don’t know. I was able to scratch the itch of physical exertion day after day, world bike touring. After a while I stopped doing a new city every night, because you spend so much time thinking about logistics, which is really boring and tiring. But even so, I just came to the conclusion that the person that I wanted to be was not an adventure blogger. If that’s what you want do, it’s super cool. I couldn’t come to an answer of why do something? I guess without infinite money I was like, okay, I need to do something.

Andrew Kortina [00:21:56] – Yeah, I mean, that’s a good motive, for now. But maybe it won’t be in the future.

Craig Cannon [00:22:01] – Yeah, yeah, I mean it’s definitely a question mark. Do you have visions of assuming you don’t work on Fin forever, your post-Fin life?

Andrew Kortina [00:22:14] – Probably won’t be a corporation. What’s cool about what we’re working on is it’s really hard and interesting, which means because there’s a hard problem and there’s 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. Everybody has to be awake at the same time. It’s just like, “Ddo I want to do that?” I don’t know, I kind of want to–

Craig Cannon [00:22:59] – The struggle is real.

Andrew Kortina [00:23:00] – Well, but the thing, it’s not, the alarm is kind of a tongue-in-cheek thing.

Craig Cannon [00:23:05] – I know what you mean.

Andrew Kortina [00:23:06] – But it’s so hard to get into a creative mode where you can… I think it takes 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. If the muse is speaking you want to be able to write down what the muse is saying, and be available to that. But when you’re coordinating huge chunks of your day around other people’s time it can be difficult. But then, on the other hand, the idea of just solo writing all the time, that seems kind of lonely, so I don’t know, it’s a tough–

Craig Cannon [00:24:01] – 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 then–

Andrew Kortina [00:24:12] – Yeah, and then it’s hard, it’s hard, really hard to do something.

Craig Cannon [00:24:16] – You’ve got to be super disciplined either way. I’m sure there’s someone who’s just randomly like, “Wah, there’s a movie idea,” and it immediate becomes super successful. But most people, not so much. 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, 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 the 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?

Andrew Kortina [00:25:06] – In a class where all the other lectures are by business people.

Craig Cannon [00:25:11] – About what, like starting companies and stuff?

Andrew Kortina [00:25:15] – The Silicon Valley shtick.

Craig Cannon [00:25:19] – Okay, got you. I thought you started it out in a very honest way where you, I wasn’t there but I just read this 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. 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. 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.

Andrew Kortina [00:26:02] – It’s kind of a shitty thing to hear as a college student. A similar thing I heard from my college professor I was having coffee with right after I graduated. She said to me, “I remember I was 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, ah. I like the idea of telling somebody something honest like that when they’re younger. But the, I don’t know, 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 I’ll go visit college campuses a lot to do recruiting and kind of look at, I’ll look at other companies like engineering blogs and just, or I’ll hear, you know, advertisements on a podcast by some engineering company. When I graduated from college, and I went to Penn, where Wharton is a big part of the culture there, and so it’s a very, it’s basically a vocational school, and that infects the entire rest of, every other program at Penn. It’s like everybody’s very focused on–

Craig Cannon [00:27:36] – Did you have like gen-ed business class you have to take?

Andrew Kortina [00:27:39] – No, I mean, but–

Craig Cannon [00:27:41] – But it’s just the vibe.

Andrew Kortina [00:27:41] – It’s just the vibe of Penn. It’s like I really envy you–

Craig Cannon [00:27:42] – Yeah, identify this–

Andrew Kortina [00:27:44] – And it’s like that, yeah. 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-four consulting company. That was just the track. Then you kind of 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. I think that’s fine. If your goal is, if what you value is providing sustenance or a stable home environment for 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, Wall Street is the bad guys, they’re all about making money, Silicon Valley is about building the future

Andrew Kortina [00:29:10] – and achieving the American dream, and just doing no evil, and it’s really, I don’t know, maybe some people get that out of it, but I have a problem with you selling that to other people and telling them that you’re going to be their source of meaning and you’re going to enable them to be impactful in the world. There’s a certain honesty to the Wall Street’s come here, work hard, make a lot of money. Okay, that’s the deal. These technology companies don’t really frame it like that. There’s a lot of great companies, and they’re building things that are making the world better in a lot of ways, but I just think they oversell this feel-good-about-yourself thing.

Craig Cannon [00:30:06] – Right, when they probably don’t even have to. On the one hand I do think that technology usually is a good thing, and many of these companies are working on great stuff, and they’re also giving jobs to people that are, you know, great, solid income. have no beef with someone that’s like, “Hey, I’m just going to go work at whatever, X company, make this money. I’m providing for a family or parents or just, myself,” which is fine. The thing that’s been kind of irking me lately is financial independence being used as this metagame that gets kind of thrown into the mix with young people, many of whom don’t really have to earn $300,000 a year. Maybe they come from a family, whatever, that 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 getting, by default this game is a multiyear game that will encompass your 20s, you might not ever do anything.” And that makes me sad.

Andrew Kortina [00:31:20] – There’s a lot of time after your 20s to do stuff.

Craig Cannon [00:31:25] – Totally, but I just like speaking, obviously people do things over the course of their entire lives, but I look around at my friends, I’m like– You have kids and it’s very easy, and I don’t have kids so it’s hard from me to say, but it’s very easy, it seems to make that your whole thing. Which is, I guess, also fine.

Andrew Kortina [00:31:45] – It’s a fine decision if people kind of go into it with open eyes and fully understand it. I just feel like there’s a little bit too much marketing of it in a certain direction that makes me uncomfortable.

Craig Cannon [00:32:01] – You said at a point, you were quoting some of the advertisements, so the words were craft, built for everyone, do the, I’m just laughing, do the most meaningful work of your career. Yhe 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.”

Andrew Kortina [00:32:31] – It’s very meditative to, one of the things that’s awesome about writing software is you can just go into this state where you’re just, you spend 10 hours and you’re like, whoa, that was so, it’s like playing a video game, right. I’m not a great drawer but I’ve done some drawing, and when you’re just, you know, drawing that cup of water right there and looking at all the different shadows and contours and just focused on that, you kind of throw out all this verbal analytical 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. I think craft has that sort of cooking is like that, or writing software is like that, working with your handsis like that, doing Excel is like that. There’s a lot of things that are like that, where you can kind of just focus in, go into that, you know, all the, everything else dims and you’re just in the zone. It’s a good escape from a lot of other things.

Craig Cannon [00:33:57] – 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, I used to do it, I mean, I still do it, so one of my buddies–

Andrew Kortina [00:34:08] – Oh, by saying like, I’m a craftsman,

Craig Cannon [00:34:10] – Well–

Andrew Kortina [00:34:10] – and you critique everyone who’s not a craftsman?

Craig Cannon [00:34:13] – 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.

Andrew Kortina [00:34:19] – Oh yeah.

Craig Cannon [00:34:20] – 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 do it at all, and this person is accomplishing stuff. That is not healthy. Then on the other hand, some people, all of these things are dichotomies, right?

Andrew Kortina [00:34:39] – Yeah, yeah, it is, I don’t know, it is tough. There’s a lot of garbage out there, but there’s a lot of people trying their best, I don’t know.

Craig Cannon [00:34:49] – At some point in one of the essays you mentioned it’s possible that VR would be a suitable life for people, maybe not for you right now, but at some point, who knows.

Andrew Kortina [00:35:00] – Yeah, I mean, my R is pretty good right now, as I like to say. Why is the R 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 is just as good as reality.

Craig Cannon [00:35:21] – VR plus some kind of chemical combination I could absolutely see being better than real life, for almost everyone, if not everyone.

Andrew Kortina [00:35:34] – I could be a professional basketball player in VR, never going to happen

Craig Cannon [00:35:37] – Totally.

Andrew Kortina [00:35:39] – in reality, right.

Craig Cannon [00:35:42] – If you could somehow slip into the, really feel like you’re LeBron James, I’ve never dunked a basketball in my entire life.

Andrew Kortina [00:35:50] – Yeah, that’d probably be pretty sick.

Craig Cannon [00:35:51] – It would be awesome.

Andrew Kortina [00:35:52] – I don’t know, in a stadium with 50,000 people cheering you on, I could be down with that, that sounds awesome.

Craig Cannon [00:35:59] – Yeah, but again, you’re left with this thing… After I’ve consumed every level of the VR game, maybe, or maybe it’s just life.

Andrew Kortina [00:36:08] – There’s this good Alan Watts thing I heard where he was talking about being omnipotent, and living forever, and he was… And omniscient, and he was like, yeah, you would, you know, that would be cool for a while, but then you’d probably get bored and you’d start doing these simulations where you’re like, “Okay, I’m going to make this game where I limit my omnipotence in some way and it’ll make it a little bit more fun.” And then you kind of get bored with that game, you realize, well, I always know that after the game is over I’m omnipotent and omniscient and I live forever. It lowers the stakes a little bit, and so you, then you start taking away the fact that you know it’s a game and you return to this state of the struggle of limited, finite life. It was just, he kind of got there from, of course that’s what you would do if you lived forever and were omnipotent.

Craig Cannon [00:37:27] – Right.

Andrew Kortina [00:37:27] – Exactly this.

Craig Cannon [00:37:29] – It traps you, I mean, do you ever lucid dream?

Andrew Kortina [00:37:32] – Not really, I have the thing where I become conscious but can’t move, right before you wake up.

Craig Cannon [00:37:39] – Oh, wow.

Andrew Kortina [00:37:39] – Which I don’t like.

Craig Cannon [00:37:40] – Yeah, no, I can’t .

Andrew Kortina [00:37:42] – I wish I lucid dreamed instead.

Craig Cannon [00:37:45] – I haven’t had your experience, but I’ve definitely lucid dreamed 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. 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. And that’s it. It’s just like I rapidly ruin the entire thing. Could you, just so that people understand, we did a podcast with Tim Urban of Wait But Why.

Craig Cannon [00:38:18] – He talks about this technological determinism as the human colossus. It’s basically the same concept. He was like, “This ball is rolling, this product will be made.” You even say, if not Venmo, something else would have happened

Andrew Kortina [00:38:36] – For sure.

Craig Cannon [00:38:36] – in that same space. How do you define technological determinism?

Andrew Kortina [00:38:43] – The way I talked about it in that talk was a little bit, I was talking more about a corollary. Technological determinism is just society as a product of technology or something. But the kind of thing that I think about a lot as a corollary of that is that, I think evolution is like this and 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. If you kind of follow that to its end you get to this place where it’s like, “Okay, well, if everything useful will necessarily be invented by somebody out of need, why should I work on anything, right?” If any possible useful thing I could come up with, somebody else is going to come up with because it’s useful, so like…

Craig Cannon [00:39:45] – Why do I–

Andrew Kortina [00:39:47] – It’s not that unique or interesting, so maybe I should just do all of the crazy useless stuff and learn to try to rescue my free will, basically. Now, the problem with that is if everybody thought that, nothing useful would ever get done. It kind of presupposes that it’s a, you know, only a few people realize that, I guess. That’s kind of how I think about technological determinism, there’s this idea that, yeah, useful stuff will be built, technology is moving forward at this pace, it’s kind of an unstoppable force, and as much as people, you know, yearn for the good old days of the, you know, Portland life of making your own cottage cheese or whatever, you’re not going to, somebody’s going to keep technology moving forward, so it’s tough to fight against it.

Craig Cannon [00:40:44] – And you use JFK’s moral argument.

Andrew Kortina [00:40:49] – That, JFK’s speech from, it was a, he gave this talk at Rice, talking about the space program, and he was talking about, why are we going to space? Costs a ton of money. And he says some awesome stuff in there. One is, why does Rice play Texas? And he was comparing the space race to a football game, which I think is hilarious.

Craig Cannon [00:41:17] – I had to step back, because I 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 is like okay, right,” that’s the argument?

Andrew Kortina [00:41:26] – Yes. Well, I just think it’s–

Craig Cannon [00:41:27] – Why do they need to?

Andrew Kortina [00:41:30] – Why does one college play another college at all?

Craig Cannon [00:41:32] – Oh, okay.

Andrew Kortina [00:41:32] – Why is there a football game, right? Because it’s fun and competition is interesting. That’s kind of one angle, which is, I think really, probably the better argument, or maybe the more, sorry, let me be, like the more truthful argument. He then gives his 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. Space technology, like all other technology, it has no morals of its own, and so it’s really up to the good people, the more moral people, who, if you’re in the US that’s you, presumably, if you’re JFK’s audience. It’s up to the good people to build the powerful technology first so that they can fight back against the bad people who also will eventually build that technology. That was just a really interesting argument. You can justify a lot of things with that argument. 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.

Craig Cannon [00:42:58] – It’s the same one that OpenAI’s using right now, and most AI researchers. At some point where you should talk about what you’re currently working on.

Andrew Kortina [00:43:09] – Right, yeah.

Craig Cannon [00:43:09] – Right, so–

Andrew Kortina [00:43:10] – Let’s do it.

Craig Cannon [00:43:10] – Let’s do it. Fin is within the AI sphere.

Andrew Kortina [00:43:16] – We like to call it AAI, artificial artificial intelligence. When we started the company there was all this, so Fin, it’s a personal assistant service, and so you can email us, text us, call us, whatever, send us work like you would send an executive assistant. When we started there was all this excitement about Alexa and Google Home and all these pure software AI natural language processing things which had very good speech-to-text kind of natural language processing, and they were pretty good at understanding most sentences that you would say to them, but are not really capable of being your full-time assistant. These people are saying this is going to be, you know, like the AI from 2001: Space Odyssey or like Jarvis from Iron Man, and it’s nowhere even close to that. But we want those things, so why don’t we try to build that today and hack it by having a system where you interact with it just like that, but instead of trying to build it with pure software, which if Google can’t do, obviously 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 a service. They are enabled by technology, like Uber, not going to be possible without GPS. There’re certain technological improvements that you can take advantage of to enable this distributed workforce to provide a new kind of service that wasn’t really possible in the past. We thought it’s be cool to do that for personal assistance-type stuff,

Andrew Kortina [00:45:02] – 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 okay tools to do them, and because there’s okay tools to do them, not many people have assistants anymore, and so they’re doing them themselves. But it’s really not an efficient use of your time,

Craig Cannon [00:45:21] – For instance–

Andrew Kortina [00:45:21] – if you’re some executive or whatever,

Craig Cannon [00:45:24] – Scheduling stuff?

Andrew Kortina [00:45:25] – to be scheduling five hours of meetings every week, right. I guess like venture capitalists, they 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 dealing with service providers and Comcast and like a plumber. If you’re spending three hours of doing that a week, which is, 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. If you ask somebody, which one would you rather do, go help your kid with their homework or play with them for three hours or be figuring out something with your health insurance? Clearly people are going to 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 to do that. 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 tons of work to figure out, 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 huge amount of costs involved in trying to piecemeal it together. We thought, “Okay, why don’t we kind of do all of that work to find good people, train them, build it so it’s a kind of consistent, reliable experience,

Andrew Kortina [00:47:00] – remember all the sort of nuances and preferences about you so that when turnover and attrition does happen you’re shielded from that, and the entity remembers your preferences around dentist appointments or whatever, right.” You don’t want to have to tell… 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 retrain them on the entire thing every time. We’ve kind of taken some, a group of people that we have, train them, give them tools for collaboration, knowledge sharing, workflow management, process management, and built this system where everything that any one of them learns about you or about the world, like how to book Hamilton tickets or how to do one medical, right, and encode that in our system. 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.

Craig Cannon [00:48:09] – Got it. There are many questions around will Fin ever, so Ryan Hoover from Product Hunt asks, “When, if ever, will Fin task completion be 100% AI-driven?”

Andrew Kortina [00:48:21] – The day that happens nobody has to work anymore, right, because Fin is a black box open-ended system, right. We will do any work that you send us, right. The day that Fin can do all work, no human has to work again, and then we’ll all go to the beach and drink pina coladas, and we’re at the–

Craig Cannon [00:48:39] – We’re back at the beginning of the podcast.

Andrew Kortina [00:48:42] – Yes. That’ll be great. 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 is not part of our network or doesn’t have access to 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.

Craig Cannon [00:49:20] – Are all these people in the Bay, or are they all over the world?

Andrew Kortina [00:49:22] – No, no, they’re, most of our people over it now are in Phoenix.

Craig Cannon [00:49:26] – Oh, okay. What’s been the hardest part and the biggest difference between starting Fin versus Venmo?

Andrew Kortina [00:49:36] – With Venmo it was always really difficult to raise money, because it was a very expensive business to run, and it had to be at a huge, Venmo’s just now starting to start to monetize. 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. That was a very, very longterm bet on a certain way to make money, and because we were never making any money and had to deal with all these SEC laws and things like that. It was always very difficult to raise money. We had to use money for all these things that were not really making the product better. That was the kind of thing that made Venmo hard. Also it was the first kind of company of any size that I worked on, so first time managing people. Lots of challenges like that. With Fin, on the other hand, I have a little bit more experience managing people, so that part is somewhat easier or at least I have some experience and knowledge of doing it in the past. We have a business model. We’re both kind of previous entrepreneurs and have social capital, so that made it a little bit easier to raise money. Then the hardest thing about Fin is just complexity. It’s the exact opposite of any, of the perfect YC company, where the YC company you pick one, or like any, like a Silicon Valley company, you pick one small thing, you get really good at doing that thing by doing tons and tons of reps on it. Then if you get a bunch of people,

Andrew Kortina [00:51:28] – using that then maybe you kind of expand outward and add on 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 not like you hire a human assistant and you say, hey, can you help me find the time to meet with Sam next week, and book me flights to Phoenix. Then the person says, “Well, I don’t book flights so you’re going to have to do that yourself, but I’ll schedule the meeting.” If we built that we just wouldn’t be competitive with a human assistant. We kind of took into this, we have to be able to do anything, which is really hard. One, it’s just hard to kind of market and explain to people what we do, because it’s not like we do one thing, we just do whatever. The other thing is it’s really hard to, well, second thing, it’s really hard to just build tools that do anything, that are both very general and also pretty productive and easy for people to learn. It’s hard to build the tools for our team that’s doing all this 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 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 task? Where is all the time going? Why is this thing, you know, this one type of task, greater variance then another type of task in terms of how long it typically takes somebody in our team to do it?

Andrew Kortina [00:53:12] – How do we categorize different groups of customers and understand what they would want, 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 stocking labor, basically, and if we’re undersupplied then people have to wait too long for work to get done. If we’re oversupplied then we’re just burning money. And then the other thing that’s really hard, the measurement is just hard because it’s a black box system. We have a heterogeneous set of people doing the work who have very different tenures, which is another big thing that affects how well they do their work, different innate skillsets, and then a very heterogeneous set of customers and a very heterogeneous set of types of tasks that we do. 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 trendline where you can say, okay, here is the impact of that thing, you have to slice on so many dimensions to try to get to a dataset that can tell you if any of the work that you did was actually good or bad. It’s just really complicated. It feels like, I don’t know, like trying, you know, to do measurement in macroeconomics, where there’re just like a billion different dimensions and you’re constantly like, oh well, we have to normalize for this and normalize for that.

Craig Cannon [00:54:55] – How much is usage correlated with what you market that Fin can do?

Andrew Kortina [00:55:03] – Today your demand for Fin is much more a function of you than of our marketing. 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 to talk to you about it, because it’s very difficult to print something. It’s really helpful to ask questions about what your needs are, and then basically we just tell you we can do all those things. But we can’t know a priori what your needs are and then put those on the page for you. There’s a certain sense where talking to you for a little bit helps us 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 going to invent another five hours of work that we can do for you. 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 TV that you would be entertained by, even if you were only currently spending five hours already a week.

Craig Cannon [00:56:14] – But it’s not like as soon as you say, Fin will book flights for you, everyone uses Fin to book flights.

Andrew Kortina [00:56:21] – Well, the people that need a flight booked, but we’re not going to convince somebody that doesn’t need a flight to book a flight.

Craig Cannon [00:56:26] – Right, of course.

Andrew Kortina [00:56:27] – It’s very much a function of each individual customer what they’ll find useful or not.

Craig Cannon [00:56:34] – Got you. Do you ever have a moment when you talk about your Lucas Venmo ads? Do ever have a moment where you’re like, I want to do this again, I want to do the same thing? How to do it for Fin and get these ads everywhere?

Andrew Kortina [00:56:46] – I don’t like to do, you know, do a redo like that. I mean, the Lucas ads were these subways ads that we did for Venmo in New York. That was really fun. I don’t think we would do something like that, because that was, the market for that was a little bit different, where it was like every person could use Venmo, when those ads went up in New York. With Fin, it’s not a product for every person right now. The thing I liked about Lucas was that it was not really, it was 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.

Craig Cannon [00:57:29] – Yeah, it’s like confusing stickers all over the subway.

Andrew Kortina [00:57:33] – Yeah, and so I liked the idea, and I’ve done this with stuff on my website where, like my About Me is not really an About Me, it’s partly fictional and really long and just not, you look in a place where you’re expecting to see one thing and then you see something that doesn’t really belong there.

Craig Cannon [00:57:54] – But your conversion rates, bro.

Andrew Kortina [00:57:55] – But I liked that, and so there’s something about that and thinking about, okay, what would that be for Fin? You know, it could be like showing up at some conference and doing some crazy shit that was not what we were supposed to be there to do. I think that would be fun. But I’m sure it would be different than what worked for Venmo, what we do for Fin.

Craig Cannon [00:58:24] – Spencer Clark asks, “How did you and your co-founder decide to sell Venmo or why?”

Andrew Kortina [00:58:33] – Well, 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 why was Braintree a good match for Venmo. One, obviously, Bill Ready, who was the CEO of Braintree, only person that kind of got it and was willing to fund the vision of Venmo and 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 they could eventually pay businesses. He was particularly, amenable to Venmo because Braintree is another company, similar to Stripe, where they have, they do credit card processing for all these different businesses. The margins on credit card processing are really thin for somebody like Braintree or like Stripe, but for PayPal they’re actually awesome, because PayPal is basically doing a ton of transactions that come from bank accounts and then charging a credit card processing fee. Instead of making like five basis points, PayPal’s making like 2% or something. It really gives you many, many more multiples on your margins if you’re in that payment processing business. What Bill saw was Venmo could help Braintree go from this very, very, very, thin margin to what’s still pretty thin margins by any standard but still many multiples on what they had. That was kind of why he thought it was a good fit, and the teams kind of matched well. They were well capitalized and had a source of revenue,

Andrew Kortina [01:00:22] – and could kind of balance out all of this Venmo that was basically just dumping into user acquisition, wiring up people’s bank accounts with the hopes that one day we could somehow convince merchants to accept Venmo as a form of payment. It just made a lot of sense, one, for Venmo to be part of Braintree, because it was these 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 understand the value of Venmo, because it was basically the same exact playbook as PayPal, understand the longterm investment it takes. I’m sure it’s probably been over a billion-dollar investment now to wire up all these bank accounts and subsidize all these peer-to-peer transactions, with the hope 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 it would be very difficult, I think, for a private financier to kind of accept the billion-dollar dream question mark.

Andrew Kortina [01:01:35] – So it just made sense

Craig Cannon [01:01:35] – Cool.

Andrew Kortina [01:01:39] – to pass this on, yeah.

Craig Cannon [01:01:40] – How long ago was that?

Andrew Kortina [01:01:43] – I think 2013.

Craig Cannon [01:01:43] – Yeah, it was a while ago. Yeah. The last thing I want to talk about was that Charlie Kaufman speech.

Andrew Kortina [01:01:49] – Oh man, it’s so good.

Craig Cannon [01:01:49] – Dude.

Andrew Kortina [01:01:51] – Everyone, anybody who’s listening to this should go, you should link to that speech. Charlie Kaufman’s incredible.

Craig Cannon [01:01:57] – I’d never heard him speak before.

Andrew Kortina [01:01:59] – I think that’s one of the only times he did that.

Craig Cannon [01:02:01] – Oh, okay. Yeah, that was great. Did you transcribe that on your own, just like–

Andrew Kortina [01:02:07] – No, I think I found either the YouTube transcription and cleaned it up, or it might have been on BAFTA’s website somewhere. But I kind of pasted the transcript on my site because I wanted to add emphasis in certain areas, because it’s long and I thought it might be helpful to have some highlights in there. I don’t know if you want to say something about what the speech is, give people some context. But it’s really amazing.

Craig Cannon [01:02:34] – It’s awesome, man. Charlie Kaufman’s a screenwriter of Being John Malkovich and many other movies. Basically the setup is talking about… I can pull it out right here. 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 in how we think of ourselves and the world, and ourselves in the world.” It was awesome.

Andrew Kortina [01:03:16] – There’s so much in there that’s so good. 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. He kind of, in that it gives context for a lot of the stuff you’ve 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. He points to that in a lot of problems that he sees in film, with people just mechanizing and putting out more of the same shit that’s just copying something else and not doing anything new. But I think in a lot of the work that he does you can see he sees that also in our daily interactions with other people, or in our relationships with even family and friends and stuff. It’s very easy to just fall into a routine and just saying the thing that is automatic. 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 the guy, and he’s running down the hill and this guy’s running up the hill, and the guy’s like, well, sure, it’s all downhill that way. And he laughs, and he’s, yeah, that was a good one, I like that. And then he passes the guy again, same spot, and the guy, same exact thing, says that. He’s like, huh, that’s kind of interesting, I guess, maybe like he forgot he said it to me. It happens another time, same spot, and he’s like, I guess he just says that every time he sees somebody here,

Andrew Kortina [01:05:24] – and he wasn’t really even pay any attention to me. And then he passes him, and he, Charlie Kaufman’s going uphill and the other guy’s going downhill, but he still says, oh sure, it’s all downhill that way. It has no context or recognition or acknowledgment of the state of the actual world, it’s just this automatic thing to say. And I think, he points it out in, it can happen to our work and it can happen to our relationships with other people. I found that really poignant.

Craig Cannon [01:06:00] – Especially in the context of a type of work that I think most people regard as very creative. 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 this trailer for this movie that’s going to come out. It’s beautiful, I’m sure it’s going to be perfectly done. But it’s just going to be totally mediocre, not really accomplish anything. Yeah, and so yeah, I think the, first of all, thanks for posting it, I had not seen it before, but also, I was just curious about 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.

Andrew Kortina [01:06:38] – I really feel deeply about… There’s a lot of important and stuff in there. But I just, I don’t like the idea, this is a little bit, again, something I was saying at Berkeley, was, there’s a track that has been laid out for everybody, and just there’s a certain way of doing things. You can, it’s very easy to just 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 to, I’m probably a little bit more generous on this than Charlie Kaufman would be, I don’t think it’s necessarily bad to do something that other people are doing or that has been done before, if you decide that that is the thing that you want to spend time doing, or that’s going to 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 understand that they’re in this automatic mode, and just following the next thing and copying the thing that somebody else did or doing the thing that somebody told them to do. In the end you have someone like that, you know, waking up 50 years later and being like, wow, I didn’t want to do any of that, or just never realizing and having that thought at all. It’s just, it’s sad. Anyway, I try to spend a lot of time thinking about, okay, how do I be intentional? Am I doing the thing that I want to do? Is it going to be different in some way? Because I do like the idea of trying to do something differently than the way other people would do it.

Andrew Kortina [01:08:29] – I think about that a lot, but it’s kind of a rabbit hole. You can spend a lot of time thinking about that and realize that it’s pretty hard to do and maybe not possible.

Craig Cannon [01:08:44] – You can fall into a new kind of trap which is competitive mindfulness, which I find so funny. I can meditate longer then you can. All right, dude, so if someone wants to talk to you online or try out Fin, what should they do?

Andrew Kortina [01:08:59] – To try out Fin we have a code for… Somebody asked, when’s Fin going to be free? It’s not going to be free, but you get $100 credit if you sign up at You could just try it out there. If you want to find me online, @kortina with a K on Twitter, or is where I post all my writing.

Craig Cannon [01:09:22] – Awesome, thanks man.

Andrew Kortina [01:09:24] – Thank you.

Craig Cannon [01:09:25] – All right, thanks for listening. As always you can find the transcript and video at If you have a second it would be awesome to give us a rating and review wherever you find your podcasts. See you next time.


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    Y Combinator created a new model for funding early stage startups. Twice a year we invest a small amount of money ($150k) in a large number of startups (recently 200). The startups move to Silicon