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Chatbots Behaving Badly™

Wooing Machine Learning Models in the Age of Chatbots

By Markus Brinsa  |  March 16, 2025

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In recent years, the intersection between advertising and artificial intelligence has become a highly contested topic, with the digital space shifting away from search engines towards AI-based chatbots. Whereas classic search advertising relies upon sponsored results and auction-based positioning, AI chatbots generate answers through vast training sets and dynamic retrieval mechanisms. This shift has made advertisers and developers alike ponder new monetization strategies while also dealing with the inherent complexity of inserting advertising content into AI.

One of the most controversial strategies is the idea of seamlessly weaving advertisements into the AI experience, so-called AI-native sponsored content.

Under this model, the goal would not be inserting ads into the dialogue but rather bringing brands and advertisers into alliance with the AI developers to produce content that can be referenced organically during interaction. Rather than inserting ads directly into the training data, which is a large and diverse corpus aggregated from many sources, advertisers could join with AI platforms to make their high-quality, authoritative content a core element within the information environment. The idea is to create a space where the sponsored content is indistinguishable from the editorial content and, thus, not undermine the trust users place in the ability of the AI to provide unbiased, relevant answers.

Meanwhile, there is also interest in leveraging real-time data integrations to introduce commercial content without altering the original training data. For instance, advertisers can build robust APIs that feed current data such as prices, inventory quantities, or special offers. When a user searches for a product or service, the AI platform can invoke these APIs to make timely suggestions or sponsored insights. This approach does not require modifying the original training data - typically fixed after the model goes live - and instead leverages live feeds that make the AI more attuned to the most recent marketplace dynamics. The technical demands for this model are the design of secure, scalable, and efficient API endpoints, the implementation of robust authentication mechanisms such as OAuth, and systems with the ability to handle high query loads without compromising the response time.

The direct injection of ad content into the training data is problematic. Training data for the large language model is drawn from an extensive range of sources across the internet, and altering the process to include curated ad content is problematic technically and ethically. Technically, the quantity and diversity of the corpus are such that no single advertiser's content could register as a measurable effect. There is also the risk that the intentional inclusion of ad data could inject biases, compromise the neutrality of the AI's responses, and undermine user trust. Ethically, users have come to trust AI for neutral and objective assistance, and the impression that the system is manipulated for commercial interests could have far-reaching implications for the technology's reputation.

Despite these challenges, experimental solutions are underway. Some industry players are wading into what might be termed a hybrid monetization model - blending elements of sponsored content, API-based data fetching, and even affiliate marketing. For example, an artificial intelligence assistant might make a restaurant recommendation based on real-time data from a partner API with clear disclaimers noting the suggestion is sponsored. This model allows advertisers to utilize the AI platform without directly compromising the training process, and developers enjoy some degree of separation between advertising and editorial content.

In summary, directly incorporating ad content into data to train AIs is not yet a widely adopted practice.

Still, advertisers and developers are currently exploring a variety of potential avenues. Solutions such as AI-native sponsored content and real-time API integrations can monetize AI services without undermining the neutrality and trust users require. As the industry continues to evolve, continuous testing and collaboration between developers and commercial partners will be needed when developing models that reconcile profitability with the preservation of unbiased, trustworthy content.

How do retraining cycles impact incorporating ad content into training data?

The AI model's reinforcement learning process and retraining cycles are a fine balance between the requirement for current data and the requirement for long-term performance. Huge language models are typically trained with gigantic data sets via the initial pre-training process, which imparts a broad sense of language and knowledge. The process, taking weeks or even months with high-performance hardware, establishes the core capabilities of the model. Once pre-training is finished, the model is put through reinforcement training - more informally called reinforcement learning from human feedback (RLHF) - to fine-tune its outputs according to quality and safety standards. The follow-up process aligns the model's responses with the likes and dislikes of humans but does not update the underlying fact data with high frequency.

These retraining cycles are not usually continuous. Most commonly, instead, businesses resort to periodic refreshes - between quarterly and even yearly cycles - since the actual training process is computationally intensive and requires a lot of investment concerning computational resources and human attention. This leads to the possibility that while the AI might get better at producing answers with better conversational strategies and enhanced safety protocols, its core knowledge might remain the same for a while. For advertisers, this is a real challenge. If the campaign is time-sensitive, employing just a model's periodically refreshed dataset might leave one vulnerable to the risk that the campaign specifics or advertising message are no longer current by the time the model is retrained.

In addressing these issues, developers have explored hybrid solutions combining the robustness of a pre-trained model with dynamic elements updated in real-time. One such avenue is the use of external data sources via APIs. Rather than sitting through a complete retraining process, an AI platform can invoke real-time databases or ad feeds to draw upon the latest data. This provides the potential for a user inquiring about a product, service, or promotion for the chatbot to insert live data into its pre-trained data with the resulting response reflecting the most current campaign details. The core model isn't modified within this hybrid model but is supplemented with new data directly related to the advertiser's immediate objectives.

Another method under consideration is incorporating retrieval-augmented generation (RAG) techniques, where the model is trained to fetch contextually relevant documents from a dynamic index during the generation process. Using RAG, the AI can tap into recent articles, deals, or product listings not present within the original model's training data. This eliminates the danger of stale content without compromising the model's language creation quality. For advertisers, the technical demand is making their data sources available and structured so that the retrieval mechanism can quickly process them. This typically involves using standard data schemas and robust API endpoints strong enough to handle frequent queries.

This reliance on regular retraining results from the demand for creating systems that can bridge the gap between model longevity and the timeliness with which data are delivered. It also speaks to advertisers' difficulty in synchronizing their campaign timelines with the update cycles of the base AI models. As the space continues to evolve, we anticipate solutions with the capability for incremental learning or fine-tuning within real-time, which would allow the AI systems to refresh with the most recent data without undergoing the process of full retraining.

In essence, while the internal retraining loops and reinforcement mechanisms are the foundations for robust and reliable AI, they also impose a latency in updating factual information. Advertisers must overcome this challenge by using external data integrations, real-time APIs, and retrieval-based systems to make their content live and impactful. One of the most critical frontiers in the ongoing evolution of monetization strategies for AI is the balance between the static nature of a pre-trained model and the dynamic demands of real-time advertising.

AI-native advertising - are there any AI chatbot providers who currently supply it?

No major provider of chatbots has yet implemented what may be called "AI-native advertising" as a mainstream feature. Most major-scale AI chat platforms - such as ChatGPT, Perplexity, or Claude - don't have advertising embedded within their outputs. Instead, they try to present content drawn from their training data or live retrieval functions with no obvious commercial bias.

Some details are noteworthy nonetheless. For example, Microsoft's Bing Chat, which uses the same tech, can also fold sponsored search results into its overall search environment. But there, too, the sponsored content is closer to a vestige of the old monetization model than a truly AI-native model. Simply put, the ads are not woven into the fabric of the AI's conversation the way the term "AI-native advertising" might imply.

A few startups and testbed platforms have tested the subtle placement of branded content or commerce links within AI-based interaction. Some experiments involve API integrations with real-time deals or curated suggestions, which constitute the first steps toward ad formats natively enabled by AI. However, these solutions are not mainstream, scaled, or ubiquitous like conventional ad formats.

The challenge is how to balance monetization with trust. Consumers will trust AI outputs, assuming that they are free from bias and untainted by commercial pressures. Providers are thus cautious about introducing advertising that would compromise this trust. Up to now, the concept of AI-native advertising is generating a lot of interest and testing, but there are no solid mainstream products from leading AI chatbot providers.

AI-native Advertising Solutions

While no major player yet provides a fully packaged "AI-native advertising" solution, many businesses and startups operating within conversational AI and commerce are experimenting with ideas that may eventually lead to such a model.

For instance, companies like Drift, Intercom, and ManyChat have historically focused on conversational marketing. Although these companies have traditionally focused on customer support and interaction, now they are exploring how to build commerce functionality and sponsored suggestions natively into the chat experience. Their interest lies in using the interface of the conversation as a means for selling and promoting content based on the user, laying some of the groundwork for what would later be known as AI-native advertising.

Meanwhile, the recent emergence of plugin ecosystems for generative AI - like the ones enabled by ChatGPT - has triggered a series of early-stage experiments and test integrations. Those experiments aim to facilitate real-time data retrieval from third-party sources like e-commerce websites, trip planners, and local listings. Although the integrations aren't labeled as ads themselves, they enable brands to place dynamic context-aware offers into AI-conversational streams. Startups involved with the experiments are testing the possibility of piping real-time product or service data via APIs so the AI can place current sponsored content into its responses. Moreover, customer service bot businesses like Ada and Inbenta are now looking into how to make data-driven offers a part of their dialogue. While their primary purpose remains to answer questions for the customer, the ancillary tech is evolving towards richer commercial integrations, which might ultimately lead to a broader ad platform natively powered by AI.

Ultimately, while the concept is still in its nascent stages and no company has yet defined a transparent, industry-standard model for AI-native advertising, these early experiments indicate the confluence of conversational AI and commerce is actively being explored. The challenge is how to do it without eroding the trust users place in the results of AI - upholding the perceived neutrality and credibility of the content provided.

About the Author

Markus Brinsa is the Founder and CEO of SEIKOURI Inc., an international strategy consulting firm specializing in early-stage innovation discovery and AI Matchmaking. He is also the creator of Chatbots Behaving Badly, a platform and podcast that investigates the real-world failures, risks, and ethical challenges of artificial intelligence. With over 15 years of experience bridging technology, business strategy, and market expansion in the U.S. and Europe, Markus works with executives, investors, and developers to turn AI’s potential into sustainable, real-world impact.

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