Will ChatGPT Ads Change OpenAI? + Amanda Askell Explains Claude's New Constitution

with Kevin Roose and Casey Newton

23 Jan 2026 24 min read 1h 28m

TL;DR

OpenAI is testing ads in ChatGPT for free and low-cost users, marking a shift toward ad-supported models despite Sam Altman's past claims that ads would be a "last resort." Kevin and Casey predict this will eventually degrade the free user experience similar to YouTube and Facebook. Anthropic's Amanda Askell reveals the new "constitution" guiding Claude's behavior—a philosophical framework designed to help the AI generalize better to unforeseen situations rather than just follow rigid rules.

Key Moments

Casey Newton

“Well, Kevin, on one hand, I think this is inevitable. There's a an analyst I follow, Eric Seufert, who often says that everything is an ad network. And if you have hundreds of millions of people coming and paying attention to a service every single week, inevitably there's going to just be overwhelming pressure to put ads on it.”

Discussing why OpenAI's move to ads is unsurprising given scale and revenue pressures

▶ 2:02

Kevin Roose

“I think that's the fear here is that while ChatGPT may start out with these very clearly labeled ad modules, over time, as the commercial pressures get more intense, they are just going to have a lot of incentives to blend that advertising content in with the organic responses and make it less noticeable.”

Comparing OpenAI's trajectory to Google's gradual de-emphasis of ad labels over years

▶ 7:52

Casey Newton

“I think you're right. I think that you know, all these companies are realizing that they're going to need you know, billions of dollars some of them hundreds of billions of dollars to fulfill their ambitions and it's just not easy to do that when you're charging people 20 bucks a month for a subscription.”

Explaining the massive capital requirements driving OpenAI's ad strategy

▶ 16:21

Amanda Askell

“The constitution is basically trying to give Claude as much as possible just like full context. So instead of just like having individual principles, it's basically just here is like what Anthropic is. Here is like how it what what you are in terms of like an AI um and who and who you're interacting with, how you're how you're deployed in the world.”

Describing the new philosophy behind Claude's constitution versus previous rule-based approaches

▶ 28:53

Amanda Askell

“Um so if you understand like the reason you're doing this is because you like actually are trying to like care about people's well-being and you come to a new situation where there's like, you know, hard conflicts between someone's well-being and like what their stated preferences are, you're a little bit better equipped to navigate it than if you just know like a set of like like rules that don't even necessarily apply”

Explaining how principle-based training helps Claude handle novel ethical dilemmas

▶ 29:33

About the show

›

Hard Fork is the New York Times podcast where tech columnist Kevin Roose and Platformer's Casey Newton break down the week's biggest developments in AI, tech, and the internet. This episode covers OpenAI's new ad strategy for ChatGPT and features an in-depth conversation with Anthropic philosopher Amanda Askell about Claude's constitutional AI framework.

Takeaways

Ad-supported AI follows predictable degradation arc OpenAI's ads follow the same pattern as Google Search and Facebook: starting clearly labeled but gradually blending into organic content as commercial pressures intensify. History suggests free users will face significantly worse experiences within 1-2 years, creating a two-tier system where only paid subscribers get clean, ad-free access to AI tools.

Scale economics make subscriptions insufficient OpenAI needs hundreds of billions of dollars to build the infrastructure for AGI-scale ambitions. At $20/month per subscriber, the math doesn't work—ad revenue is mathematically necessary to fund the company's stated goals, making this shift inevitable regardless of past rhetoric about ads being a "last resort."

Constitutional AI prioritizes principles over rigid rules Anthropic's new Claude constitution frames AI behavior as values-based rather than rule-based, teaching the model to understand *why* it should behave certain ways. This approach is designed to generalize better to unforeseen situations where rigid rules don't apply, treating AI alignment as a philosophical problem rather than a technical compliance issue.