Nov 20, 2018 · 1h 9m · y-combinator
Andrew Kortina of Venmo and Fin on Technological Determinism and Work's Relationship to Dignity · Y Combinator
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In this podcast episode, Venmo and Fin co-founder Andrew Kortina explores how technological progress and automation challenge traditional views linking work to human dignity, while offering insights into technological determinism, personal authenticity, and building AI-driven startups.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. How this is scored →
The partners as informed peer 3.3 Guest teaching 3.9 Guest disagreement 1.7 The partners pushing back 1.9
speaking balance: gold is the partners, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 8:01 Kortina dismisses the Twitch job creation argument
Kortina counters Craig's premise that humans will easily invent new jobs in a post-scarcity era by explaining that attention economies concentrate rewards in extreme power laws rather than supporting the masses.
Hardest push from the partners ▶ 18:53 Craig counters Kortina's cynicism about travelCraig directly pushes back against Kortina's dismissive take on global tourism, arguing that off-the-beaten-path travel and bike touring yield authentic human connection rather than mere commercial extraction.
Biggest teaching moment ▶ 13:40 Kortina reframes the technological singularityKortina surprises the host by asserting that the technological singularity is not an impending AI event but something that already occurred when money became the primary algorithmic optimizer for human behavior.
The partners hold their own ▶ 19:28 Craig demonstrates expertise on authentic travel and bike touringCraig draws from his personal multi-month international bike touring experience to explain how alternative travel modalities overcome commercial tourism barriers.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | The partners as informed peer | Guest teaching | Guest disagreement | The partners pushing back | Why |
|---|---|---|---|---|---|---|
| The Origins of Human Dignity and Work Ethics | 3 | 4 | 1 | 1 | Craig introduces Kortina's essay on human dignity and work, asking why he returned to building startups after selling Venmo. Kortina deconstructs the concept of dignity as an inherited cultural artifact rather than an innate truth, setting a collaborative, philosophical tone. | |
| Flow States, Buddhism, and Purpose in an Abundant Future | 3 | 4 | 2 | 2 | Craig asks whether Kortina's philosophical writing is merely a thought experiment or something he actively practices like Buddhism. Kortina explains why he rejects Buddhist philosophy for large-scale societal ambition, noting it lacks the drive to solve existential species-level threats. | |
| Job Creation, the Attention Economy, and Gratitude | 4 | 5 | 3 | 3 | Craig challenges Kortina with the idea that humans easily invent new jobs, citing Twitch truck driving simulators. Kortina dismisses this as an attention economy power-law trap and shares a detailed anecdote about grocery store toothbrushes to illustrate economic waste and the thesis that money is already an algorithmic singularity. | |
| Minimalist Living, Commercial Tourism, and Seeking Purpose | 4 | 3 | 2 | 4 | Craig inquires about Kortina's personal minimalism and pushes back on his cynical view of travel when Kortina dismisses tourism as a commercial extraction machine. Craig offers his own bike touring methodology as a way to engage authentically with locals. | |
| Post-Fin Ambitions, Creative Flow, and the Friction of Routines | 3 | 2 | 1 | 2 | The conversation covers post-Fin life, creative flow states, and the friction that corporate coordination and alarms impose on deep creative work. Both share mutual reflections on the discipline required when leaving structured jobs. | |
| Critique of Silicon Valley Culture and Craft as Existential Coping | 4 | 4 | 3 | 2 | Craig references Kortina's UC Berkeley lecture critiquing Silicon Valley's moral messaging. Kortina argues Wall Street is more honest than tech companies that oversell meaning, while both discuss craft and coding as meditative coping mechanisms against existential despair. | |
| Virtual Reality Simulations, Omnipotence, and Lucid Dreaming | 3 | 3 | 1 | 1 | Craig and Kortina explore VR, Alan Watts' thought experiment regarding omnipotence leading back to simulated struggle, and personal lucid dreaming experiences. The exchange is highly collaborative and conversational. | |
| Defining Technological Determinism and Moral Arguments in Tech | 3 | 4 | 2 | 2 | Craig asks Kortina to define technological determinism. Kortina explains how evolutionary necessity drives innovation regardless of individual contributions, connecting it to JFK's moral defense of the space race against Russian advances. | |
| Fin: Building Artificial Artificial Intelligence and Operational Scale | 3 | 5 | 2 | 2 | Craig prompts Kortina on Fin's AI approach. Kortina gives an in-depth explanation of 'Artificial Artificial Intelligence,' contrasting human-in-the-loop operational networks with pure software bots and detailing the complex macroeconomic-style measurement challenges they face. | |
| Guerrilla Marketing and Non-Sequitur Branding | 3 | 5 | 1 | 1 | Craig asks about Venmo's non-sequitur subway advertising and the decision to sell to Braintree. Kortina explains the unit economics of payment processing, showing why thin-margin processors benefit enormously from bank account transaction rails. | |
| Charlie Kaufman's Speech, Authenticity, and Living Intentionally | 3 | 4 | 1 | 1 | Craig brings up Charlie Kaufman's BAFTA speech on authenticity and avoiding automatic living. Kortina reflects on intentionality, the tragedy of unexamined career tracks, and resisting mechanization in interpersonal relationships. |
Statements from this episode (13)
Kortina: Cultures linked dignity to work to build survival surpluses
“Why would a culture connect dignity with the idea of work? And it's, 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…”
Kortina: There is nothing morally wrong with doing heroin all day
“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 …”
Kortina: Buddhism does not motivate civilizations to attempt massive projects
“I had this thought once, like, you know, Buddhists are not gonna get us off this planet when the sun burns out. Like, it's a very From my sort of, you know, 50,000 foot view of it seems like a very like internal focused life is struggling. How do I cope with t…”
Kortina: Linking dignity to productive work is dangerous in post-scarcity
“As that becomes less necessary and there's more abundance, then 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, may…”
Kortina: The singularity already happened, and money is the algorithm
“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.”
Kortina: Venmo prioritized transaction notes to humanize peer-to-peer payments
“Actually we wanted to kind of like humanize the money and make it less about the dollars and cents and more. That's why the note is like such a focal point of them. I was like, what is the thing that you're doing? What does the moment that you're sharing with …”
Kortina: Tech companies oversell moral meaning compared to Wall Street
“My problem with the way that Silicon Valley does it is they, they've always had this, like, Wall Street is the bad guys. They're all about making money. Silicon Valley is about, you know, building the future and, you know, like, achieving, like, the American d…”
Kortina: Immersing in craft silences overthinking and existential despair
“It's very meditative to like, one of the things that's awesome about writing software is you can just like go into this, you know, state where you're just, you spend 10 hours and you're like, whoa, that was so fun. It's like playing a video game, right? Or, I …”
Cannon: VR combined with chemicals could surpass physical reality
“I mean, VR plus some kind of, like, chemical combination, I could absolutely see being better than real life. For almost everyone. If not everyone.”
Cannon: OpenAI uses the Cold War race-to-build moral justification
“I mean, it's the same one that OpenAI is using right now. Yeah. And most AI researchers.”
Kortina: Virtual assistants must be generalists to compete with humans
“With Finn, we're competing with a full-time human assistant and a full-time human assistant will just do whatever you ask them... If we built that, we just wouldn't be competitive with a human assistant. So we kind of took into this, we have to be able to do a…”
Kortina: Venmo's only options before selling to Braintree were shutting down
“Well, one, it was, the options were shut down Venmo forever or sell it.”
Kortina: Investors burned over $1B to subsidize Venmo peer-to-peer transactions
“I'm sure it's probably been over, like, a billion-dollar investment now to, like, wire up all these bank handles and subsidize all the peer-to-peer transactions with the hopes of someday turning on Payments to the merchant network”