AI developer Benjamin De Kraker was asking ChatGPT about using encryption features in Windows when he noticed something odd at the bottom of his screen. Next to an icon for a shopping bag, a clickable message urged him to shop for “home and groceries” at Target.
De Kraker, who pays $20 per month for ChatGPT’s “plus” plan, was outraged about the seeming advertisement. “It’s F-ing showing me ADS TO SHOP AT TARGET,” he tweeted last week. “Yeah, screw this. Lose all your users.”
As De Kraker’s tweet went viral, several officials from OpenAI, the company that makes ChatGPT, quickly apologized and tried to explain that the messages were not exactly ads.
“Anything that feels like an ad needs to be handled with care, and we fell short,” responded Mark Chen, chief research officer at OpenAI. Another exec explained that the message was not technically an advertisement, because Target did not pay OpenAI. Rather, it was a promotion by OpenAI for a shopping app Target had created using ChatGPT. The promotions have been halted, Chen added.
But analysts expect that sooner or later, advertising will infiltrate AI apps, just as it seeped into other ad-free realms that attracted large audiences, like movie theaters, taxi cabs, social media, and streaming TV services. OpenAI, in particular, has said it needs to raise $1 trillion to build data centers, adding pressure to raise revenue. Chief executive Sam Altman has said he’d consider the move only “with great caution.”
Advertising could help make AI tools more accessible to people who can’t afford subscriptions. But in social media, for instance, ads have included intrusive personal data tracking and created incentives for apps to add addictive features to keep users hooked.
So far, the leading chatbot company has kept its revenue-enhancing efforts focused on users who are already shopping for something, where it can collect commissions instead of running actual ads.
For example, on Monday, OpenAI announced a deal with Instacart to let users shop for groceries at the same time they are chatting with AI about recipes. And the company has previously struck deals to link to the e-commerce sites of Walmart, Booking.com, and Target, among others, when users are searching for a product.
A few days after De Kraker and others posted about the ad-like links, Nick Turley, who is head of ChatGPT at OpenAI and used to work at Instacart, tried to clear the air.
“There are no live tests for ads – any screenshots you’ve seen are either not real or not ads,” he tweeted. “If we do pursue ads, we’ll take a thoughtful approach.”
Still, OpenAI needs to bring in many more billions of dollars to support its plans. “Advertising or commission revenue is likely the inevitable endgame,” analyst Michael Morton at MoffettNathanson wrote in a report last month, noting the vast sums the company needs to fund its infrastructure.
And ads may be the only way ChatGPT can pull in enough money while also offering a free version to maintain its early lead with consumers, according to analyst Ben Thompson. “ChatGPT really needs to get going on that ad-supported model” in order to ensure “the best possible product is ‘free’ to use,” he wrote recently.
Google, the leading purveyor of digital ads on the internet, has also been rumored to be adding commercial messages to its chatbot, known as Gemini. The latest version of Google’s chatbot has already been pulling ahead of ChatGPT on some tests, and the search giant has said it is rapidly gaining users. On Monday, a story in Ad Week claimed that the Google was already talking with major advertisers about rolling out Gemini ads in 2026.
But the company was quick to quash the rumor.
“This story is based on uninformed, anonymous sources who are making inaccurate claims,” Dan Taylor, Google’s vice president of global ads, tweeted after the story ran. “There are no ads in the Gemini app and there are no current plans to change that.”
The reason AI companies are moving slowly with advertising is likely to avoid angering customers like De Kraker — and even free users may get so turned off that they jump to a competing product.
Consumer trust, once lost, is hard to regain. As ChatGPT product manager Turley noted: “People trust ChatGPT and anything we do will be designed to respect that.”
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👋 Design software firm PTC in Boston hired Jennifer DiRico as executive vice president and chief financial officer, starting Jan. 1. DiRico currently serves as CFO of Commvault.
👩💻 Coding software company OutSystems in Boston hired Kim Seabrook as chief revenue officer. Seabrook previously led North American enterprise revenue at Shopify.
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✈️ Electric aircraft maker Beta Technologies in Burlington, Vt., struck a deal that could bring in up to $1 billion from Eve Air Mobility for supplying and servicing motors, the company said.
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What We’re Reading
One Year With ChatGPT Pro as a First Hire (Michael Wall blog post)
As Key Talent Abandons Apple, Meet the New Generation of Leaders Taking On the Old Guard (Wired)
Kicking Robots: Humanoids and the tech-industry hype machine (Harper’s Magazine)
👋 Thanks for reading. We’ll be back next Tuesday.
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Aaron Pressman can be reached at aaron.pressman@globe.com. Follow him @ampressman.