AI commerce is here

Why ChatGPT’s confident recommendations can be misleading, and how Meta’s “ultimate business results machine” works

ChatGPT

That moment when you're scrolling through Instagram, heartbroken after a breakup, and you suddenly see ads for solo travel packages? Not a coincidence. A Facebook ad suggesting the perfect gift for your best friend's birthday next week? There's something bigger happening behind those ads. (And, no, it’s not that your phone is listening to you, that’s a story for another time.)

AI is transforming our world in ways we're still wrapping our heads around. It's easily the most powerful technological shift our generation will witness, and in our capitalist reality it's no surprise this technology has attracted billions in investor dollars. Now, these tech giants are making their inevitable next move: turning all that investment into profit through your shopping habits.

Recently, OpenAI quietly slipped shopping features into ChatGPT, while Meta unveiled an AI ad engine that can automatically generate thousands of ad variations without human input. Beyond the surface-level convenience, these developments represent a major shift in who controls what you buy and why. It’s all happening behind algorithmic curtains most of us can't peek behind.

When AI makes stuff up to get you shopping

OpenAI is positioning its shopping assistant as your "trusted advisor," offering seemingly straightforward product recommendations with buy buttons. It could be a refreshing change from ad-cluttered e-commerce sites.

But, in testing, ChatGPT made up product details across electronics, home goods, and fashion categories. (And The New York Times reported last week that AI hallucinations are getting worse, not better, contrary to what we all hoped for a year ago.)

Meanwhile, Meta isn't trying to be subtle. If Facebook has been collecting your data for years, it can now pinpoint your most vulnerable moments (like when you've just changed your relationship status or when you're feeling bad about the way you look) and capitalize on them with eerily specific ads.

Think about it: the platform where you've documented your life for the past decade knows more about your shopping triggers than your closest friends. It knows when you typically shop (late night stress-scrolling), what aesthetic you respond to, and even which emotional appeals make you click "buy now."

Follow the money (it leads straight to your wallet)

In a recent interview, OpenAI's CEO Sam Altman floated a modest affiliate model where they'd take a small percentage of purchases made through their recommendations. OpenAI insists its shopping suggestions aren’t ads. But with a target of $125 billion in revenue by 2029, I wonder if ChatGPT's shopping recommendations could soon be monetized in a really powerful way.

We gave Meta our lives — every like, share, and scroll — and it repurposed that data into laser-targeted ads. OpenAI faces a similar crossroads: maintain its helpful, ad-lite persona or embrace the commerce machine it's built. What we do know right now is that ChatGPT has a function that can remember your conversations, and that OpenAI is looking into rolling out a lifetime subscription.

Behind the scenes, ChatGPT's shopping feature connects with major e-commerce platforms like Shopify, with systems that have the potential to prioritize certain products over others. Meta's system goes even further, analyzing your behaviour to identify exactly which messaging will get you to buy.

The hidden trade-off

The deal seems simple: convenience and personalization in exchange for letting algorithms show you products you’ll probably like. But that trade isn't always clear. As I mentioned above, we handed our data to Facebook for "free" social connection, and now it's used to influence our buying decisions at our most vulnerable moments.

Regulation is still playing catch-up. While Europe debates rules requiring disclosure for AI-generated commerce content, the US and Canada remain largely hands-off. Meta will label AI-created ads in its internal library, but you won't necessarily know when you're seeing one in your feed.

The most profound shift may be psychological. As these systems mediate more of our buying decisions, they're fundamentally altering how we discover products and perceive value. The traditional consumer journey—awareness, consideration, purchase—is collapsing into a single AI-guided interaction, with the considerations happening inside black-box algorithms rather than consumer consciousness.

And every purchase you make through these AI systems trains them to get even better at selling to you.

Your anti-algorithm shopping survival guide

Know your triggers: Notice when you're emotionally vulnerable (stressed, tired, celebrating, sad) and pause before making purchases at these times.

Use privacy tools: Clear cookies regularly, use browser extensions that block trackers, and consider a VPN for more anonymous browsing.

Budget before browsing: Decide what you need and set a spending limit before opening shopping apps or talking to AI assistants.

Ask "Why this, why now?": When an AI recommends something, question why it's showing you this particular item at this particular moment.

Implement a waiting period: Create a 24-hour rule for purchases over a certain amount to avoid impulse buys.

Comparison shop manually: Don't rely solely on an AI's recommendations — check multiple sources and read independent reviews.

Opt out where possible: Review privacy settings on all platforms and opt out of personalized shopping recommendations where you can.

Taking back control

The future of shopping isn't going back to the pre-AI days, but that doesn't mean you have to surrender your agency to algorithms. Being aware of how these systems work is your first step toward making choices that actually serve you.

Try this: If ChatGPT or Instagram serves you a seemingly perfect product recommendation, pause and ask yourself what signals you might have given to trigger that suggestion. Was it your recent search history? A conversation you had near your phone? A life event you posted about?

Understanding the patterns helps you recognize when you're being sold to versus when you're actively seeking a product. The most powerful shopping tool isn't AI, it's your awareness of how these systems are designed to influence you. Shop with your eyes wide open, and your wallet will thank you.

Help train this newsletter's neural networks with caffeine! ⚡️ Buy me a coffee to keep the AI insights coming. ☕️

What to read next >