The Guy Who Took ChatGPT to Market is now Warning Us About It.: Zack Kass

August 20, 2026

AI Summary

5 min read

Zack Kass spent more than a decade at OpenAI, leading the go-to-market strategy that brought ChatGPT to hundreds of millions of users. He had every reason to stay and keep cheering. Instead, he left at the peak of his career, convinced that the technology industry had broken its promise to society. The problem, as he tells it, is not AI itself. It is the context in which AI is arriving — a world where screens have already done immense damage, where the cost of housing, healthcare, and education has tripled, and where young people have been fed the worst news on earth from the moment they got a smartphone. Kass argues that we are asking the wrong question. The debate should not be about the future of work. It should be about the future of living.

The broken promise of the last 30 years

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What you'll learn

1 (00:06) **Introduction: Zack Kass, the Go-to-Market Mind Behind ChatGPT** - Host introduces Zack Kass, who led OpenAI's go-to-market strategy and now warns about AI's broken promise to society.
2 (04:25) **Why People Don't Hate AI—They Hate Its Corrupted Context** - Kass explains that most people don't hate the technology itself, but the story being told about its costs and harms.
3 (09:49) **The Faustian Bargain: Cheap Vice, Expensive Pillars of Life** - Kass describes the absurd economy where dopamine and spiritual dereliction are dirt cheap, but the essentials of a good life are prohibitively expensive.
4 (11:28) **The Real Problem: The Screen as a Demon** - Kass argues that the corrupted relationship with technology is principally about the screen, and policymakers are still ignoring it.
5 (13:32) **Technology Can Drive Down Costs—But Policy Must Allow It** - Kass explains that AI will eventually make things cheaper, but only if we put pressure on policymakers to let it.
6 (16:36) **The China Contrast: Why 80% of Chinese People Are Excited About AI** - Kass shares his observations from visiting China three times a year, where the public views AI as a means to make life better.
7 (19:55) **The Availability Heuristic and Algorithmic Negativity** - The host connects Kass's argument to the psychological concept of the availability heuristic, where constant exposure to the worst news makes people assume new technology will be negative.

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Guests on this episode

Zack Kass

Show Notes

Everybody knows ChatGPT. Almost no one knows the person who took it to market. In this episode of Big Swings Only, Kwame Christian sits down with Zack Kass, who spent over a decade at the center of the AI industry and led go-to-market strategy at OpenAI — bringing the technology to hundreds of millions of professionals worldwide.

Zack walked away from that career at its peak, driven by a hard truth: technology promised to make life more affordable and instead made housing, healthcare, and education far more expensive, while making distraction and dopamine dirt cheap. In this conversation, he makes the case that people don't actually hate AI — they hate what the last 30 years of screens have done to them — and argues that AI, paired with the right policy choices, could finally deliver on technology's oldest promise: driving down the cost of a good life for everyone, not just the wealthy.