Thankfully, there has been a recent thaw on this front. It is now increasingly understood that, eventually, the leading answer engines will have consumed and trained on all of the data available on the web. When that happens, to continue being of use to consumers, the LLMs will need access to fresh data from publishers. This development should provide content creators, finally, with a modicum of leverage and bring AI providers to the bargaining table.
Seemingly in recognition of this eventuality, a number of hyper-scalers have begun rolling out these payment architectures, which they call content marketplaces. Microsoft has taken the lead, introducing a pilot program a few weeks ago, Amazon is reportedly at work on its own, and Google has even begun playing its usual game of footsie with publishers.
Similarly, a handful of other companies have sought to build out these marketplaces, including content delivery networks like Cloudflare and Fastly, as well as startups and private firms like Tollbit and ProRata. I have written about a few of them before.
But on Wednesday, a new entrant joined the fray, whose approach to the matter is unlike any other so far.
A bot and human web
Called Monetization OS, the new startup operates on the assumption that an ideal system would use a single infrastructure for content creators to monetize both their human and machine traffic.
This layer would effectively take the form of a very sophisticated paywall, which makes a lot of sense, given the background of its founder James Henderson. Henderson, whom I spoke with last week, was the founder of Zephyr, an intelligent paywall technology that was acquired by Zuora in August 2022 for $44 million.
Unlike standard paywalls, Zephyr uses machine learning to present visitors to a website with a paywall experience tailored to their individual behavior.
Rather than a binary or metered gate, these paywalls make determinations based on a variety of factors, such as the referring website—someone sent from LinkedIn has a higher probability of paying than one from Instagram—what content they are consuming, how often they have visited, how long they linger, and a million other elements.
With Monetization OS, Henderson wants to apply an even more complex version of this technology to websites, but this time to enable it to personalize paywalls for both humans and AI agents.
For humans, this means not just tailoring when the paywall arrives, but also the product that it sells. A returning reader that engages exclusively with sports content might receive a subscription offer that offers unlimited access only to sports content for a fraction of the price of a standard subscription—same with someone who only reads a certain author or during a certain period of time. For every specific visitor, a specific experience.



