The Oracle vs. The Salesman: Will ads be ChatGPT’s “Yahoo moment”?

There was a fleeting moment in the late 1990s when the internet felt purely utilitarian. You went to a search engine, typed a query, and received the best possible answer the algorithm could find. It felt like magic. Then came the banners, the pop-ups, and the “sponsored” links that looked suspiciously like organic results.

We are currently living through a similar Golden Age with Generative AI. For the last two years, ChatGPT has been a clean, white interface dedicated to one thing: intelligence. But with the official introduction of advertising into OpenAI’s ecosystem on 9 February 2026, we are dangerously close to repeating the history of the early web. This is a history where the product stops being the tool and starts being the audience.

The lesson of Yahoo Mail: From utility to billboard

Before Google dominated, Yahoo was the king of the internet. But as Yahoo leaned heavily into display advertising, particularly within Yahoo Mail, its design philosophy shifted. The goal was no longer to get the user to their destination as fast as possible; the goal became to keep the user on the page to view more ads.

The inbox became a crowded bazaar of distractions. This left a massive opening for Google, which launched with a stark, white page and zero distractions. Google won because its incentives were aligned with the user: Best answer wins. OpenAI is currently the “Google” of this analogy, but by introducing ads, they risk becoming the “Yahoo” of the AI era.

The Altman pivot: “Democratic necessity” or financial reality?

For years, Sam Altman called advertising a “last resort.” He even critiqued Google’s model, arguing that ads are “dependent on Google doing badly” because if a search engine gave the perfect answer, there would be no reason to click an ad.

However, the reality of running a “money furnace”  with projected losses set to triple to $14 billion in 2026 has forced a spectacular reverse. On 9 February 2026, OpenAI officially began testing ads for free and “Go” tier users in the US. Altman now defends the move as a way to keep AI accessible for those who cannot afford monthly subscriptions, dismissively referring to Claude users as “rich people” during his recent public spat with Anthropic.

The “conflict of interest”: Why AI ads are different

The introduction of advertising into a Large Language Model is far more dangerous than it is in search. In a traditional search engine, there is a visual wall between the organic results and the ads. You see the “Sponsored” tags, and you can mentally filter them out. In a conversational interface, that wall crumbles.

• In Search: Ads are a distraction.
• In AI: Ads are a distortion.

If you ask for the best marathon running shoe and the AI has a partnership with a specific brand, the distortion begins. Will it prioritise the sponsor? Will it adopt a more favourable tone? Trust evaporates the moment a user suspects the advice is bought.

The opportunity for the next “pure” player

By pivoting to an ad-model, OpenAI leaves a massive gap for a competitor to do exactly what Google did to Yahoo: offer a premium, private, ad-free alternative. In a world of “sponsored intelligence,” objective truth becomes a luxury product.

Competitors like Anthropic are already pouncing on this. Their Super Bowl LX commercial mocked the idea of intrusive AI ads with the tagline: “Ads are coming to AI. But not to Claude.” They are betting that power users will treat “ad-free” as a proxy for “trustworthy.”

The future is a choice

OpenAI is officially entering the “Enshittification” cycle. This is the process, coined by Cory Doctorow, where a platform first becomes good to its users, then abuses those users to make things better for advertisers, and finally abuses the advertisers to claw back all the value for itself.

OpenAI is betting that its AI is so entrenched in our professional lives that we will not leave, even as the quality begins to slide. They are betting they can adjust the parameters just enough to make a profit without users noticing the “crapification” of the truth.

The danger to us lies in them being right, that we slowly accept that access to knowledge should occur through the lens of a salesman and that every query, no matter how personal, is just a touch point in a sales cycle.