Cory Doctorow’s theory of “enshittification” explains how tech platforms rot from within. As AI grows more profitable—and powerful—it risks the same fate.

I recently vacationed in Italy. As one does these days, I ran my itinerary past GPT-5 for sightseeing suggestions and restaurant recommendations. The bot reported that the top choice for dinner near our hotel in Rome was a short walk down Via Margutta. It turned out to be one of the best meals I can remember. When I got home, I asked the model how it chose that restaurant, which I hesitate to reveal here in case I want a table sometime in the future (Hell, who knows if I’ll even return: It is called Babette. Call ahead for reservations.) The answer was complex and impressive. Among the factors were rave reviews from locals, notices in food blogs and the Italian press, and the restaurant’s celebrated combination of Roman and contemporary cooking. Oh, and the short walk.

Something was required from my end as well: trust. I had to buy into the idea that GPT-5 was an honest broker, picking my restaurant without bias; that the restaurant wasn’t shown to me as sponsored content and wasn’t getting a cut of my check. I could have done deep research on my own to double-check the recommendation (I did look up the website), but the point of using AI is to bypass that friction.

The experience bolstered my confidence in AI results but also made me wonder: As companies like OpenAI get more powerful, and as they try to pay back their investors, will AI be prone to the erosion of value that seems endemic to the tech apps we use today?

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